CA2527499A1 - Foamable pharmaceutical compositions and methods for treating a disorder - Google Patents
Foamable pharmaceutical compositions and methods for treating a disorder Download PDFInfo
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- CA2527499A1 CA2527499A1 CA002527499A CA2527499A CA2527499A1 CA 2527499 A1 CA2527499 A1 CA 2527499A1 CA 002527499 A CA002527499 A CA 002527499A CA 2527499 A CA2527499 A CA 2527499A CA 2527499 A1 CA2527499 A1 CA 2527499A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A61K9/122—Foams; Dry foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Abstract
Novel compositions of matter comprising a foamable delivery system are provided. Novel methods for treating a disease, disorder, or condition using the novel compositions, are further provided. Novel methods for making and delivering a foamable pharmaceutical composition are also provided. While the novel compositions and foamable drug delivery system may be utilized for administration of a wide variety of drugs to epithelialtissues, to treat a wide variety of diseases, disorders, or conditions, the inventive compositions and foamable drug delivery systems are particularly useful for the dermatological administration of corticosteroids and antifungal agents.
Claims (53)
1. A foamable delivery system which comprises:
(i) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof;
(ii) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(iii) a propellant; and (iv) an acid in an amount to affect the delivery system's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a) (R b)C(OH)COOH I
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, Cl, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH
group;
(c) an alpha ketoacid of formula II:
(R a) COCOO (R b) II
or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, Cl, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
(i) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof;
(ii) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(iii) a propellant; and (iv) an acid in an amount to affect the delivery system's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a) (R b)C(OH)COOH I
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, Cl, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH
group;
(c) an alpha ketoacid of formula II:
(R a) COCOO (R b) II
or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, Cl, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
2. A pharmaceutical composition comprising:
(A) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof; and (B) a pharmaceutically acceptable carrier, comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(ii) a propellant; and (iii) an acid in an amount to affect the composition's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COOH
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, C1, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH group;
(c) an alpha ketoacid of formula II:
(R a)COCOO(R b) or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, C1, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
(A) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof; and (B) a pharmaceutically acceptable carrier, comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(ii) a propellant; and (iii) an acid in an amount to affect the composition's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COOH
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, C1, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH group;
(c) an alpha ketoacid of formula II:
(R a)COCOO(R b) or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, C1, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
3. The pharmaceutical composition of claim 2, which is effective for treating a disease, disorder, or condition in a mammal in need thereof when applied to epithelial cell tissues of said mammal.
4. The pharmaceutical composition of claim 2, wherein said one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof are selected from the group consisting of steroids, antifungal agents, antimicrobials, ureas and salts and derivatives thereof, cancer treating agents, treatment agents for inflammatory bowel disorders, agents intended to protect the skin, modify its appearance, or improve its rate of healing, and mixtures thereof.
5. The pharmaceutical composition of claim 4, wherein said steroid is a corticosteroid which is selected from the group consisting of alclometasone dipropionate, amcinonide, beclamethasone dipropionate, betamethasone benzoate, betamethasone dipropionate, betamethasone valerate, budesonide, clobetasol propionate, clobetasone butyrate, cortisone acetate;
desonide, desoximetasone, diflorasone diacetate, diflucortolone valerate, fluclorolone acetonide, flumethasone pivalate, fluocinolone acetonide, fluocinonide, fluocortin butyl, fluocortolone preparations, fluprednidene acetate, flurandrenolide, flurandrenolone, fluticosone propionate, halcinonide, halobetasol propionate, hydrocortisone, hydrocortisone acetate, hydrocortisone butyrate, hydrocortisone propionate, hydrocortisone valerate, methylprednisolone acetate, mometasone furoate, pramoxine hydrochloride, prednisone acetate, prednisone valerate, triamcinolone acetonide, and mixtures thereof.
desonide, desoximetasone, diflorasone diacetate, diflucortolone valerate, fluclorolone acetonide, flumethasone pivalate, fluocinolone acetonide, fluocinonide, fluocortin butyl, fluocortolone preparations, fluprednidene acetate, flurandrenolide, flurandrenolone, fluticosone propionate, halcinonide, halobetasol propionate, hydrocortisone, hydrocortisone acetate, hydrocortisone butyrate, hydrocortisone propionate, hydrocortisone valerate, methylprednisolone acetate, mometasone furoate, pramoxine hydrochloride, prednisone acetate, prednisone valerate, triamcinolone acetonide, and mixtures thereof.
6. The pharmaceutical composition of claim 4, wherein said antifungal agent is selected from the group consisting of imidazoles, hydroxy pyridones, triazoles, allyl amines, undecylenic acid derivatives, tolnaftate, haloprogin, pyridinethiones, cloquinol, and mixtures thereof.
7. The pharmaceutical composition of claim 4, wherein said antifungal agent is selected from the group consisting of amphotericin B, butoconazole nitrate, ciclopirox olamine, clindamycin, clioquinol, clotrimazole, econazole, econazole nitrate, fluconazole, flucytosine, griseofulvin, itraconazole, ketoconazole, miconazole, micronazole, naftifine, nystatin, omadine disulfide, sulconazole, terbinafine, terconazole, tioconazole, tolnaftate, triacetin, unecylenic acid, zinc pyrithione, and mixtures thereof.
8. The pharmaceutical composition of claim 2, wherein said one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof comprise a urea or a salt or derivative thereof optionally in combination with an additional active therapeutic agent.
9. The pharmaceutical composition of claim 2, wherein said composition has a concentration of degradation product(s) less than about 5% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
10. The pharmaceutical composition of claim 9, wherein said composition has a concentration of degradation product(s) less than about 2% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
11. The pharmaceutical composition of claim 2, wherein said solvent composition is selected from the group consisting of water, ethanol, isopropyl alcohol, benzyl alcohol, dimethyl isosorbide, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof.
12. The pharmaceutical composition of claim 2, wherein said surfactant composition is selected from the group consisting of:
(a) a compound of the formula:
CH3(CH2)xCH2(OCH2CH2)nOH, wherein n is 4-8 and x is 6-20;
(b) a compound of the formula:
H3C(CH2)xC(O)(OCH2CH2)nOC(O)(CH2)yCH3, wherein n is 2-90, x is 6-20, and y is 6-20;
(c) a compound of the formula:
H3C(CH2)nCH2OSO3X, wherein n is 10-22 and X is H, Li, Na, or K;
(d) a compound of the formula:
H3C(CH2)nCH2OPO3X, wherein n is 10-22 and X is Be, Mg, or Ca;
(e) a compound of the formula:
wherein R1 and R2 is each independently a C1-C9 straight or branched chain alkyl, a C2-C9 straight or branched chain alkenyl, or a C2-C9 straight or branched chain alkynyl; and X is H, Li, Na, or K;
(f) a compound of the formula:
wherein R1 is a fatty acid;
R2 is a C1-C9 straight or branched chain alkyl alcohol, a C2-C9 straight or branched chain alkenyl alcohol, or a C2-C9 straight or branched chain alkynyl alcohol; and X is H, Li, Na, or K;
(g) a compound of the formula:
wherein x is 8-75;
y is 30-35; and z is 8-75;
(h) a compound of the formula:
wherein x is 18-21;
y is 7-163; and z is 18-21;
(i) mineral oil, microcrystalline wax, and distillates;
(j) a compound of the formula;
wherein R1, R2, and R3 are each independently a C1-C9 straight or branched chain alkyl;
(k) a compound of the formula:
wherein x is 2-500; and R1, R2, R3, R4, R5, R6, R7, and R8 are each independently H, C1-C22 straight or branched chain alkyl, C2-C22 straight or branched chain alkenyl, C2-C22 straight or branched chain alkynyl, C1-C22 straight or branched chain alkoxy, C6-C14 aryl, C6-C22 alkyl-substituted aryl, or C6-C22 aryl substituted aryl;
(1) polysorbate 60 and sorbitan monostearate;
(m) pharmaceutically acceptable salts thereof; and (n) mixtures thereof.
(a) a compound of the formula:
CH3(CH2)xCH2(OCH2CH2)nOH, wherein n is 4-8 and x is 6-20;
(b) a compound of the formula:
H3C(CH2)xC(O)(OCH2CH2)nOC(O)(CH2)yCH3, wherein n is 2-90, x is 6-20, and y is 6-20;
(c) a compound of the formula:
H3C(CH2)nCH2OSO3X, wherein n is 10-22 and X is H, Li, Na, or K;
(d) a compound of the formula:
H3C(CH2)nCH2OPO3X, wherein n is 10-22 and X is Be, Mg, or Ca;
(e) a compound of the formula:
wherein R1 and R2 is each independently a C1-C9 straight or branched chain alkyl, a C2-C9 straight or branched chain alkenyl, or a C2-C9 straight or branched chain alkynyl; and X is H, Li, Na, or K;
(f) a compound of the formula:
wherein R1 is a fatty acid;
R2 is a C1-C9 straight or branched chain alkyl alcohol, a C2-C9 straight or branched chain alkenyl alcohol, or a C2-C9 straight or branched chain alkynyl alcohol; and X is H, Li, Na, or K;
(g) a compound of the formula:
wherein x is 8-75;
y is 30-35; and z is 8-75;
(h) a compound of the formula:
wherein x is 18-21;
y is 7-163; and z is 18-21;
(i) mineral oil, microcrystalline wax, and distillates;
(j) a compound of the formula;
wherein R1, R2, and R3 are each independently a C1-C9 straight or branched chain alkyl;
(k) a compound of the formula:
wherein x is 2-500; and R1, R2, R3, R4, R5, R6, R7, and R8 are each independently H, C1-C22 straight or branched chain alkyl, C2-C22 straight or branched chain alkenyl, C2-C22 straight or branched chain alkynyl, C1-C22 straight or branched chain alkoxy, C6-C14 aryl, C6-C22 alkyl-substituted aryl, or C6-C22 aryl substituted aryl;
(1) polysorbate 60 and sorbitan monostearate;
(m) pharmaceutically acceptable salts thereof; and (n) mixtures thereof.
13. The pharmaceutical composition of claim 12, wherein said surfactant composition is selected from the group consisting of laureth-4, PEG-2 dilaurate, stearic acid, sodium lauryl sulfate, dioctyl sodium sulfosuccinate, cocoamphopropionate, poloxamex 188, meroxapol 258, triethanolamine, dimethicone, polysorbate 60;
sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof.
sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof.
14. The pharmaceutical composition of claim 2, wherein said acid is selected from the group consisting of acetic acid, acetylsalicylic acid, adipic acid, ascorbic acid, aspartic acid, benzoic acid, boric acid, carbonic acid, citric acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, gluconic acid, glutaric acid, glycine, glyceric acid, glycolic acid, glutamic acid, hippuric acid, hydrochloric acid, lactic acid, malefic acid, malic acid, malonic acid, mandelic acid, methanesulfonic acid, music acid, nitrous acid, oxalic acid, pelargonic acid, phosphoric acid, propionic acid, saccharin, salicylic acid, sorbic acid, succinic acid, sulfuric acid, tartaric acid, thioglycolic acid, thiosulfuric acid, undecylenic acid, ethanolamine, derivatives thereof, and mixtures thereof.
15. The pharmaceutical composition of claim 2, wherein said composition additionally comprises a foam inhibitor.
16. The pharmaceutical composition of claim 2, wherein said composition is packaged in a container suitable for storage and delivery of said composition.
17. The pharmaceutical composition of claim 16, wherein said container is composed of steel, aluminum, glass, plastic, or mixtures thereof.
18. The pharmaceutical composition of claim 16, wherein said container further comprises one or more protective coatings.
19. The pharmaceutical composition of claim 16, wherein said container comprises two or more compartments permitting the composition to be physically separated into two separate portions until dispensed from the container through a valve assembly.
20. A pharmaceutical composition comprising:
(A) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof; and (B) a pharmaceutically acceptable carrier, comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, ethanol, isopropyl alcohol, benzyl alcohol, dimethyl isosorbide, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of laureth-4, PEG-2 dilaurate, stearic acid, sodium lauryl sulfate, dioctyl sodium sulfosuccinate, cocoamphopropionate, poloxamer 188, meroxapol 258, triethanolamine, dimethicone, polysorbate 60, sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof;
(ii) a propellant; and (iii) an acid in an amount to affect the composition's pH selected from the group consisting of acetic acid, acetylsalicylic acid, adipic acid, ascorbic acid, aspartic acid, benzoic acid, boric acid, carbonic acid, citric acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, gluconic acid, glutaric acid, glycine, glyceric acid, glycolic acid, glutamic acid, hippuric acid, hydrochloric acid, lactic acid, maleic acid, malic acid, malonic acid, mandelic acid, methanesulfonic acid, mucic acid, nitrous acid, oxalic acid, pelargonic acid, phosphoric acid, propionic acid, saccharin, salicylic acid, sorbic acid, succinic acid, sulfuric acid, tartaric acid, thioglycolic acid, thiosulfuric acid, undecylenic acid, ethanolamine, naturally and synthetically derived amino acids, derivatives thereof, and mixtures thereof.
(A) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof; and (B) a pharmaceutically acceptable carrier, comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, ethanol, isopropyl alcohol, benzyl alcohol, dimethyl isosorbide, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of laureth-4, PEG-2 dilaurate, stearic acid, sodium lauryl sulfate, dioctyl sodium sulfosuccinate, cocoamphopropionate, poloxamer 188, meroxapol 258, triethanolamine, dimethicone, polysorbate 60, sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof;
(ii) a propellant; and (iii) an acid in an amount to affect the composition's pH selected from the group consisting of acetic acid, acetylsalicylic acid, adipic acid, ascorbic acid, aspartic acid, benzoic acid, boric acid, carbonic acid, citric acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, gluconic acid, glutaric acid, glycine, glyceric acid, glycolic acid, glutamic acid, hippuric acid, hydrochloric acid, lactic acid, maleic acid, malic acid, malonic acid, mandelic acid, methanesulfonic acid, mucic acid, nitrous acid, oxalic acid, pelargonic acid, phosphoric acid, propionic acid, saccharin, salicylic acid, sorbic acid, succinic acid, sulfuric acid, tartaric acid, thioglycolic acid, thiosulfuric acid, undecylenic acid, ethanolamine, naturally and synthetically derived amino acids, derivatives thereof, and mixtures thereof.
21. A pharmaceutical composition having a starting concentration of an active therapeutic agent comprising:
(A) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof; and (B) a pharmaceutically acceptable carrier, comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(ii) a propellant; and (iii) an acid in an amount to affect the composition's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COON
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b, are independently selected from the group consisting of H, F, C1, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b, may be optionally substituted with an OH, SH, CHO, COOH group;
(c) an alpha ketoacid of formula II:
(R a)COCOO(R b) or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, C1, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof, wherein said composition maintains a concentration of degradation product(s) less than about 5% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
(A) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof; and (B) a pharmaceutically acceptable carrier, comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(ii) a propellant; and (iii) an acid in an amount to affect the composition's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COON
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b, are independently selected from the group consisting of H, F, C1, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b, may be optionally substituted with an OH, SH, CHO, COOH group;
(c) an alpha ketoacid of formula II:
(R a)COCOO(R b) or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, C1, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof, wherein said composition maintains a concentration of degradation product(s) less than about 5% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
22. The pharmaceutical composition of claim 21, wherein said composition has a concentration of degradation product(s) less than about 2% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
23. A method for treating a disease, disorder, or condition in a mammal in need thereof, comprising administering to said mammal an effective amount of a foamable pharmaceutical composition, said composition comprising:
(i) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof;
(ii) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(iii) a propellant; and ( iv) an acid in an amount to affect the composition's pH
selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COOH
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, C1, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH
group;
(c) an alpha ketoacid of formula II:
(R a)COCOO(R b) or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, C1, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COON, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
(i) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof;
(ii) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof;
(iii) a propellant; and ( iv) an acid in an amount to affect the composition's pH
selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COOH
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, C1, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH
group;
(c) an alpha ketoacid of formula II:
(R a)COCOO(R b) or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, C1, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COON, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
24. The pharmaceutical composition of claim 23, wherein said composition has a concentration of degradation product(s) less than about 5% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
25. The pharmaceutical composition of claim 23, wherein said composition has a concentration of degradation product(s) less than about 2% of the starting concentration of said active therapeutic agent or its pharmaceutically acceptable salt, ester, or solvate.
26. The method of claim 23, wherein said solvent composition is selected from the group consisting of water, ethanol, isopropyl alcohol, benzyl alcohol, dimethyl isosorbide, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof.
27. The method of claim 23, wherein said surfactant composition is selected from the group consisting of:
(a) a compound of the formula:
CH3(CH2)xCH2(OCH2CH2)nOH, wherein n is 4-8 and x is 6-20;
(b) a compound of the formula:
H3C(CH2)XC(O)(OCH2CH2)nOC(O)(CH2)yCH3, wherein n is 2-90, x is 6-20, and y is 6-20;
(c) a compound of the formula:
H3C(CH2)nCH2OSO3X, wherein n is 10-22 and X is H, Li, Na, or K;
(d) a compound of the formula:
H3C(CH2)nCH2OPO3X, wherein n is 10-22 and X is Be, Mg, or Ca;
(e) a compound of the formula:
wherein R1 and R2 is each independently a C1-C9 straight or branched chain alkyl, a C2-C9 straight or branched chain alkenyl, or a C2-C9 straight or branched chain alkynyl; and X is H, Li, Na, or K;
(f) a compound of the formula:
wherein R1 is a fatty acid;
R2 is a C1-C9 straight or branched chain alkyl alcohol, a C2-C9 straight or branched chain alkenyl alcohol, or a C2-C9 straight or branched chain alkynyl alcohol; and X is H, Li, Na, or K;
(g) a compound of the formula:
wherein x is 8-75;
y is 30-35; and z is 8-75;
(h) a compound of the formula:
wherein x is 18-21;
y is 7-163; and z is 18-21;
(i) mineral oil, microcrystalline wax, and distillates;
(j) a compound of the formula:
wherein R1, R2, and R3 are each independently a C1-C9 straight or branched chain alkyl;
(k) a compound of the formula:
wherein x is 2-500; and R1, R2, R3, R4, R5, R6, R7, and R8 are each independently H, C1-C22 straight or branched chain alkyl, C2-C22 straight or branched chain alkenyl, C2-C22 straight or branched chain alkynyl, C1-C22 straight or branched chain, alkoxy, C6-C14 aryl, C6-C22 alkyl-substituted aryl, or C6-C22 aryl substituted aryl;
(1) polysorbate 60 and sorbitan monostearate;
(m) pharmaceutically acceptable salts thereof; and (n) mixtures thereof.
(a) a compound of the formula:
CH3(CH2)xCH2(OCH2CH2)nOH, wherein n is 4-8 and x is 6-20;
(b) a compound of the formula:
H3C(CH2)XC(O)(OCH2CH2)nOC(O)(CH2)yCH3, wherein n is 2-90, x is 6-20, and y is 6-20;
(c) a compound of the formula:
H3C(CH2)nCH2OSO3X, wherein n is 10-22 and X is H, Li, Na, or K;
(d) a compound of the formula:
H3C(CH2)nCH2OPO3X, wherein n is 10-22 and X is Be, Mg, or Ca;
(e) a compound of the formula:
wherein R1 and R2 is each independently a C1-C9 straight or branched chain alkyl, a C2-C9 straight or branched chain alkenyl, or a C2-C9 straight or branched chain alkynyl; and X is H, Li, Na, or K;
(f) a compound of the formula:
wherein R1 is a fatty acid;
R2 is a C1-C9 straight or branched chain alkyl alcohol, a C2-C9 straight or branched chain alkenyl alcohol, or a C2-C9 straight or branched chain alkynyl alcohol; and X is H, Li, Na, or K;
(g) a compound of the formula:
wherein x is 8-75;
y is 30-35; and z is 8-75;
(h) a compound of the formula:
wherein x is 18-21;
y is 7-163; and z is 18-21;
(i) mineral oil, microcrystalline wax, and distillates;
(j) a compound of the formula:
wherein R1, R2, and R3 are each independently a C1-C9 straight or branched chain alkyl;
(k) a compound of the formula:
wherein x is 2-500; and R1, R2, R3, R4, R5, R6, R7, and R8 are each independently H, C1-C22 straight or branched chain alkyl, C2-C22 straight or branched chain alkenyl, C2-C22 straight or branched chain alkynyl, C1-C22 straight or branched chain, alkoxy, C6-C14 aryl, C6-C22 alkyl-substituted aryl, or C6-C22 aryl substituted aryl;
(1) polysorbate 60 and sorbitan monostearate;
(m) pharmaceutically acceptable salts thereof; and (n) mixtures thereof.
28. The method of claim 27, wherein said surfactant composition is selected from the group consisting of laureth-4, PEG-2 dilaurate, stearic acid, sodium lauryl sulfate, dioctyl sodium sulfosuccinate, cocoamphopropionate, poloxamer 188, meroxapol 258, triethanolamine, dimethicone, polysorbate 60, sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof.
29. The method of claim 23, wherein said acid is selected from the group consisting of acetic acid, acetylsalicylic acid, adipic acid, ascorbic acid, aspartic acid, benzoic acid, boric acid, carbonic acid, citric acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, gluconic acid, glutaric acid, glycine, glyceric acid, glycolic acid, glutamic acid, hippuric acid, hydrochloric acid, lactic acid, malefic acid, malic acid, malonic acid, mandelic acid, methanesulfonic acid, mucic acid, nitrous acid, oxalic acid, pelargonic acid, phosphoric acid, propionic acid, saccharin, salicylic acid, sorbic acid, succinic acid, sulfuric acid, tartaric acid, thioglycolic acid, thiosulfuric acid, undecylenic acid, ethanolamine, derivatives thereof, and mixtures thereof.
30. The method of claim 23, wherein said foamable pharmaceutical composition is administered topically to the skin.
31. The method of claim 23, wherein said foamable pharmaceutical composition is administered topically to mucosal epithelial cell tissue of the mammal's mouth, ear, nasal passages, vagina, urethra, or rectum.
32. The method of claim 23, wherein said disease, disorder, or condition is selected from the group consisting of eczema, infantile eczema, psoriasis, scalp psoriasis, atopic dermatitis, dermatitis herpetiformis, contact dermatitis, seborrheic dermatitis, neurodermatitis, pruritis, fungal diseases, and intertrigo.
33. The method of claim 32, wherein said fungal diseases are selected from the group consisting of tinea corporis, tinea pedis, tinea unguium, tinea capitis, tinea cruris, tinea barbae, candidiasis and tinea versicolor.
34. The method of claim 32, wherein said disease is eczema.
35. A method for treating a skin condition in a mammal in need thereof, comprising administering to the skin of said mammal an effective amount of a foamable pharmaceutical composition, said composition comprising:
(i) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof;
(ii) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, ethanol, isopropyl alcohol, benzyl alcohol, dimethyl isosorbide, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of laureth-4, PEG-2 dilaurate, stearic acid, sodium lauryl sulfate, dioctyl sodium sulfosuccinate, cocoamphopropionate, poloxamer 188, meroxapol 258, triethanolamine, dimethicone, polysorbate 60, sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof;
(iii) a propellant; and (iv) an acid in an amount to affect the composition's pH
selected from the group consisting of acetic acid, acetylsalicylic acid, adipic acid, ascorbic acid, aspartic acid, benzoic acid, boric acid, carbonic acid, citric acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, gluconic acid, glutaric acid, glycine, glyceric acid, glycolic acid, glutamic acid, hippuric acid, hydrochloric acid, lactic acid, malefic acid, malic acid, malonic acid, mandelic acid, methanesulfonic acid, mucic acid, nitrous acid, oxalic acid, pelargonic acid, phosphoric acid, propionic acid, saccharin, salicylic acid, sorbic acid, succinic acid, sulfuric acid, tartaric acid, thioglycolic acid, thiosulfuric acid, undecylenic acid, ethanolamine, naturally and synthetically derived amino acids, derivatives thereof, and mixtures thereof.
(i) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof;
(ii) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, ethanol, isopropyl alcohol, benzyl alcohol, dimethyl isosorbide, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of laureth-4, PEG-2 dilaurate, stearic acid, sodium lauryl sulfate, dioctyl sodium sulfosuccinate, cocoamphopropionate, poloxamer 188, meroxapol 258, triethanolamine, dimethicone, polysorbate 60, sorbitan monostearate, pharmaceutically acceptable salts thereof, and mixtures thereof;
(iii) a propellant; and (iv) an acid in an amount to affect the composition's pH
selected from the group consisting of acetic acid, acetylsalicylic acid, adipic acid, ascorbic acid, aspartic acid, benzoic acid, boric acid, carbonic acid, citric acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, gluconic acid, glutaric acid, glycine, glyceric acid, glycolic acid, glutamic acid, hippuric acid, hydrochloric acid, lactic acid, malefic acid, malic acid, malonic acid, mandelic acid, methanesulfonic acid, mucic acid, nitrous acid, oxalic acid, pelargonic acid, phosphoric acid, propionic acid, saccharin, salicylic acid, sorbic acid, succinic acid, sulfuric acid, tartaric acid, thioglycolic acid, thiosulfuric acid, undecylenic acid, ethanolamine, naturally and synthetically derived amino acids, derivatives thereof, and mixtures thereof.
36. A method of making a foamable pharmaceutical composition, comprising the steps of:
(A) admixing an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof and a pharmaceutically acceptable carrier comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant.
a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof; and (ii) an acid in an amount to affect the composition's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid; glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a) (R b) C (OH) COOH I
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, Cl, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH group;
(c) an alpha ketoacid of formula II:
(R a) COCOO (R b) II
or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, Cl, Br, I, OH, CHO, COON, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof; and (B) packaging said mixture in a container suitable for storage and delivery of said composition.
(A) admixing an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof and a pharmaceutically acceptable carrier comprising:
(i) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant.
a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtures thereof; and (ii) an acid in an amount to affect the composition's pH selected from the group consisting of:
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid; glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof;
(b) an alpha hydroxyacid of formula I:
(R a) (R b) C (OH) COOH I
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, Cl, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH group;
(c) an alpha ketoacid of formula II:
(R a) COCOO (R b) II
or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, Cl, Br, I, OH, CHO, COON, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof; and (B) packaging said mixture in a container suitable for storage and delivery of said composition.
37. The method of claim 36, additionally comprising the step of charging said container with a propellant.
38. The method of claim 37, wherein said propellant is selected from the group consisting of hydrocarbons, petroleum gases, chlorofluorocarbons (CFC's), hydrofluoroalkanes (HFA's), dimethyl ether, propane-isobutane, non-soluble compressed gases, soluble compressed gasses, and mixtures thereof.
39. The method of claim 36, wherein said container is composed of steel, aluminum, glass, plastic, or mixtures thereof.
40. The method of claim 36, wherein said container further employs one or more protective coatings.
41. The method of claim 36, wherein said container comprises two or more compartments permitting the composition to be physically separated into two separate portions until dispensed from the container through a valve assembly.
42. The method of claim 36, wherein said container comprises a valve assembly.
43. The method of claim 42, wherein said valve assembly permits said foamable pharmaceutical composition to be released from said container either via continuous delivery or as a metered dose.
44. The method of claim 42, wherein said valve assembly accommodates an attachment to facilitate delivery. of said foamable pharmaceutical composition.
45. The method of claim 36, wherein said packaging step B) is performed using a single-step. filling process.
46. The method of claim 36, wherein said packaging step B) is performed using a multiple-step filling process.
47. The method of claim 36, wherein said packaging step B) is performed using an under-the-cup process, a through-the-valve process, or a cold fill process.
48. A method of delivering a foamable pharmaceutical composition from a container comprising providing an expelling force generated by mechanical means to said foamable pharmaceutical composition, said foamable pharmaceutical composition comprising:
(i) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof;
(ii) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtuxes thereof; and (iii) an acid in an amount to affect the composition's pH
selected from the group consisting of;
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof,;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COOH I
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, Cl, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH
group;
(c) an alpha ketoacid of formula II:
(R a) COCOO (R b) II
or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, Cl, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
(i) an effective amount of one or more active therapeutic agents or pharmaceutically acceptable free bases, salts, esters, or solvates thereof;
(ii) a foamable delivery system which comprises:
(a) a solvent composition selected from the group consisting of water, a volatile propellant, a C1-C6 fluid alkyl or branched alkyl alcohol, an aromatic alcohol, an ether of a sorbitol derivative, propylene carbonate, xylene, methylene chloride, ethylhexanediol, polysiloxanes, dimethyl ether, and mixtures thereof; and (b) a surfactant composition selected from the group consisting of a polyoxyethylene fatty ether, a polyoxyethylene fatty ester, a fatty acid, a sulfated fatty acid surfactant, a phosphated fatty acid surfactant, a sulfosuccinate surfactant, an amphoteric surfactant, a non-ionic poloxamer surfactant, a non-ionic meroxapol surfactant, a petroleum derivative surfactant, an aliphatic amine surfactant, a polysiloxane derivative, a sorbitan fatty acid ester, pharmaceutically acceptable salts thereof, and mixtuxes thereof; and (iii) an acid in an amount to affect the composition's pH
selected from the group consisting of;
(a) acetylsalicyclic acid, ascorbic acid, boric acid, carbonic acid, formic acid, ethanesulfonic acid, fumaric acid, glycerophosphoric acid, hippuric acid, hydrochloric acid, maleic acid, methanesulfonic acid, nitrous acid, oxalic acid, phosphoric acid, saccharin, sorbic acid, sulfuric acid, thiosulfuric acid, undecylenic acid, ethanolamine, and a pharmaceutically acceptable salt, ester, or solvate thereof,;
(b) an alpha hydroxyacid of formula I:
(R a)(R b)C(OH)COOH I
or a pharmaceutically acceptable salt, lactone, or solvate thereof wherein R a and R b are independently selected from the group consisting of H, F, Cl, Br, and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein each of R a and R b may be optionally substituted with an OH, SH, CHO, COOH
group;
(c) an alpha ketoacid of formula II:
(R a) COCOO (R b) II
or a pharmaceutically acceptable salt, ester, or solvate thereof wherein R a and R b are independently selected from the group consisting of H and saturated or unsaturated, isomeric or non-isomeric, straight, branched, or cyclic C1-C25 alkyl, aralkyl, or aryl groups, wherein R a may be optionally substituted with an F, Cl, Br, I, OH, CHO, COOH, or alkoxy group having 1 to 9 carbon atoms;
(d) an acid of formula III:
or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein n is 0-6;
X is H, OH, or NH2, each Y is H or OH, or X and Y are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N;
Z is H, CH3, OH, COOH, or SH, provided that Y and Z are not both OH, or Y and Z are optionally taken together to form a 5-7 membered saturated or unsaturated carbocyclic ring or a 5-7 membered saturated or unsaturated heterocyclic ring, wherein one or more ring atom(s) of said heterocyclic ring is O, S, or N; and (e) mixtures thereof.
49. The method of claim 48, wherein said expelling force is in the form of a propellant.
50. The method of claim 49, wherein said propellant is a gas compressed by mechanical means.
51. The method of claim 49, wherein said propellant is air.
52. The method of claim 48, wherein said expelling force is created by a pump action.
53. The method of claim 48, wherein said expelling force is generated by a squeezing action.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/445,487 US7186416B2 (en) | 2003-05-28 | 2003-05-28 | Foamable pharmaceutical compositions and methods for treating a disorder |
| US10/445,487 | 2003-05-28 | ||
| PCT/US2004/016733 WO2004105702A2 (en) | 2003-05-28 | 2004-05-27 | Foamable pharmaceutical compositions and methods for treating a disorder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2527499A1 true CA2527499A1 (en) | 2004-12-09 |
| CA2527499C CA2527499C (en) | 2012-01-24 |
Family
ID=33450867
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2527499A Expired - Fee Related CA2527499C (en) | 2003-05-28 | 2004-05-27 | Foamable pharmaceutical compositions and methods for treating a disorder |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7186416B2 (en) |
| EP (1) | EP1633368B1 (en) |
| JP (1) | JP4871728B2 (en) |
| KR (1) | KR101141220B1 (en) |
| CN (1) | CN1794998A (en) |
| AT (1) | ATE533493T1 (en) |
| AU (1) | AU2004242963B2 (en) |
| BR (1) | BRPI0410721A (en) |
| CA (1) | CA2527499C (en) |
| ES (1) | ES2377064T3 (en) |
| IL (1) | IL172082A0 (en) |
| MX (1) | MXPA05012842A (en) |
| PL (1) | PL1633368T3 (en) |
| WO (1) | WO2004105702A2 (en) |
| ZA (1) | ZA200510388B (en) |
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- 2004-05-27 AT AT04753550T patent/ATE533493T1/en active
- 2004-05-27 CN CNA2004800144040A patent/CN1794998A/en active Pending
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- 2004-05-27 WO PCT/US2004/016733 patent/WO2004105702A2/en active Application Filing
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8940321B2 (en) | 2003-12-12 | 2015-01-27 | Otic Pharma Ltd. | Compositions for treatment of ear disorders and methods of use thereof |
| US9393242B2 (en) | 2003-12-12 | 2016-07-19 | Otic Pharma Ltd. | Compositions for treatment of ear disorders and methods of use thereof |
Also Published As
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| BRPI0410721A (en) | 2006-06-20 |
| EP1633368B1 (en) | 2011-11-16 |
| PL1633368T3 (en) | 2012-04-30 |
| KR20060023972A (en) | 2006-03-15 |
| ZA200510388B (en) | 2006-12-27 |
| US20040241099A1 (en) | 2004-12-02 |
| JP2007500235A (en) | 2007-01-11 |
| ATE533493T1 (en) | 2011-12-15 |
| KR101141220B1 (en) | 2012-05-07 |
| JP4871728B2 (en) | 2012-02-08 |
| WO2004105702A2 (en) | 2004-12-09 |
| CA2527499C (en) | 2012-01-24 |
| MXPA05012842A (en) | 2006-05-17 |
| WO2004105702A3 (en) | 2005-05-06 |
| EP1633368A4 (en) | 2007-03-14 |
| US7186416B2 (en) | 2007-03-06 |
| CN1794998A (en) | 2006-06-28 |
| US20070059253A1 (en) | 2007-03-15 |
| AU2004242963A1 (en) | 2004-12-09 |
| EP1633368A2 (en) | 2006-03-15 |
| ES2377064T3 (en) | 2012-03-22 |
| IL172082A0 (en) | 2009-02-11 |
| AU2004242963B2 (en) | 2009-05-28 |
| US7829107B2 (en) | 2010-11-09 |
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