CA2408008A1 - Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin - Google Patents
Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin Download PDFInfo
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- CA2408008A1 CA2408008A1 CA002408008A CA2408008A CA2408008A1 CA 2408008 A1 CA2408008 A1 CA 2408008A1 CA 002408008 A CA002408008 A CA 002408008A CA 2408008 A CA2408008 A CA 2408008A CA 2408008 A1 CA2408008 A1 CA 2408008A1
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- alkynyl
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
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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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
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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
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
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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
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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
-
- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
Abstract
Disclosed are pharmaceutical compositions containing a cyclodextrin and a therapeutically effective amount of a glycopeptide antibiotic or a salt thereof. Also disclosed are methods of treating a bacterial disease in a mammal by administering such pharmaceutical compositions.
Claims (19)
1. A composition comprising a cyclodextrin and a glycopeptide antibiotic, or a pharmaceutically acceptable salt thereof.
2. The composition of claim 1 which further comprises water.
3. The composition of claim 1 which is a powder.
4. The composition of claim 1 which is a lyophilized powder.
5. A pharmaceutical composition comprising an aqueous cyclodextrin carrier and a therapeutically effective amount of a glycopeptide antibiotic, or a pharmaceutically acceptable salt thereof.
6. The pharmaceutical composition of Claim 5, wherein the pharmaceutical composition comprises:
(a) a therapeutically effective amount of a glycopeptide antibiotic, or a pharmaceutically acceptable salt thereof;
(b) 1 to 40 weight percent of a cyclodextrin; and (c) 60 to 99 weight percent of water, provided that the components of the composition total 100 weight percent.
(a) a therapeutically effective amount of a glycopeptide antibiotic, or a pharmaceutically acceptable salt thereof;
(b) 1 to 40 weight percent of a cyclodextrin; and (c) 60 to 99 weight percent of water, provided that the components of the composition total 100 weight percent.
7. The pharmaceutical composition of Claim 5, wherein the cyclodextrin is hydroxypropyl-.beta.-cyclodextrin or sulfobutyl ether .beta.-cyclodextrin.
8. The pharmaceutical composition of Claim 7, wherein the cyclodextrin is hydroxypropyl-.beta.-cyclodextrin.
9. The pharmaceutical composition of Claim 6, wherein the cyclodextrin comprises about 5 to 35 weight percent of the composition.
10. The pharmaceutical composition of Claim 9, wherein the cyclodextrin comprises about 10 to 30 weight percent of the composition.
11. The pharmaceutical composition of Claim 6, wherein the glycopeptide antibiotic is a lipidated glycopeptide antibiotic.
12. The pharmaceutical composition of Claim 1, wherein the glycopeptide antibiotic is a compound of formula I:
wherein:
R1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic and -R a-Y-R b-(Z)x; or R1 is a saccharide group optionally substituted with -R a-Y-R b-(Z)x, R f -C(O)R f, or -C(O)-R a-Y-R b-(Z)x;
R2 is hydrogen or a saccharide group optionally substituted with -R a-Y-R b-(Z)x, R f, -C(O)R f, or -C(O)-R a-Y-R b-(Z)x;
R3 is -OR c, -NR c R c, -O-R a-Y-R b-(Z)x, -NR c-R a-Y-R b-(Z)x, -NR c R e;
or -O-R e; or R3 is a nitrogen-linked, oxygen-linked, or sulfur-linked substituent that comprises one or more phosphono groups;
R4 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, -R a-Y-R b-(Z)x, -C(O)R d and a saccharide group optionally substituted with -R a-Y-R b-(Z)x, R
f, -C(O)R f, or -C(O)-R a-Y-R b-(Z)x;
R5 is selected from the group consisting of hydrogen, halo, -CH(R c)-NR c R c, -CH(R c)-NR c R c, -CH(R c)-NR c-R a-Y-R b-(Z)x,-CH(R c)-R
x, -CH(R c)-NR c-R a-C(=O)-R x, and a substituent that comprises one or more phosphono groups;
R6 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, -R a-Y-R b-(Z)x, -C(O)R d and a saccharide group optionally substituted with -NR c-R a-Y-R b-(Z)x, or R5 and R6 can be joined, together with the atoms to which they are attached, form a heterocyclic ring optionally substituted with -NR c-R a-Y-R b-(Z)x;
R7 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl,-R a-Y-R b-(Z)x, and -C(O)R d;
R8 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic;
R9 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, allcenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic;
R10 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic; or R8 and R10 are joined to form -Ar1-O-Ar2-, where Ar1 and Ar2 are independently arylene or heteroarylene;
R11 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic, or R10 and R11 are joined, together with the carbon and nitrogen atoms to which they are attached, to form a heterocyclic ring;
R12 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic, -C(O)R d, -C(NH)R d, -C(O)NR c R c, -C(O)OR d, -C(NH)NR c R c and -R a-Y-R b-(Z) x, or R11 and R12 are joined, together with the nitrogen atom to which they are attached, to form a heterocyclic ring;
R13 is selected from the group consisting of hydrogen or -OR14;
R14 is selected from hydrogen, -C(O)R d and a saccharide group;
each R a is independently selected from the group consisting of alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene and substituted alkynylene;
each R b is independently selected from the group consisting of a covalent bond, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene and substituted alkynylene, provided R b is not a covalent bond when Z is hydrogen;
each R c is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic and -C(O)R d;
each R d is independently selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic;
R e is a saccharide group;
each R f is independently alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, or heterocyclic;
R x is an N-linked amino saccharide or an N-linked heterocycle;
X1, X2 and X3 are independently selected from hydrogen or chloro;
each Y is independently selected from the group consisting of oxygen, sulfur, -S-S-, -NR c-, -S(O)-, -SO2-, -NR c C(O)-, -OSO2-, -OC(O)-, -NR c SO2-, -C(O)NR c-, -C(O)O-, -SO2NR c-, -SO2O-, -P(O)(OR c)O-, -P(O)(OR c)NR c-, -OP(O)(OR c)O-,-OP(O)(OR c)NR c-, -OC(O)O-, -NR c C(O)O-, -NR c C(O)NR c-, -OC(O)NR c-, -C(=O)-, and -NR cSO2NR c-;
each Z is independently selected from hydrogen, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclic;
n is 0, I or 2; and x is 1 or 2;
or a pharmaceutically acceptable salt, stereoisomer, or prodrug thereof.
wherein:
R1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic and -R a-Y-R b-(Z)x; or R1 is a saccharide group optionally substituted with -R a-Y-R b-(Z)x, R f -C(O)R f, or -C(O)-R a-Y-R b-(Z)x;
R2 is hydrogen or a saccharide group optionally substituted with -R a-Y-R b-(Z)x, R f, -C(O)R f, or -C(O)-R a-Y-R b-(Z)x;
R3 is -OR c, -NR c R c, -O-R a-Y-R b-(Z)x, -NR c-R a-Y-R b-(Z)x, -NR c R e;
or -O-R e; or R3 is a nitrogen-linked, oxygen-linked, or sulfur-linked substituent that comprises one or more phosphono groups;
R4 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, -R a-Y-R b-(Z)x, -C(O)R d and a saccharide group optionally substituted with -R a-Y-R b-(Z)x, R
f, -C(O)R f, or -C(O)-R a-Y-R b-(Z)x;
R5 is selected from the group consisting of hydrogen, halo, -CH(R c)-NR c R c, -CH(R c)-NR c R c, -CH(R c)-NR c-R a-Y-R b-(Z)x,-CH(R c)-R
x, -CH(R c)-NR c-R a-C(=O)-R x, and a substituent that comprises one or more phosphono groups;
R6 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, -R a-Y-R b-(Z)x, -C(O)R d and a saccharide group optionally substituted with -NR c-R a-Y-R b-(Z)x, or R5 and R6 can be joined, together with the atoms to which they are attached, form a heterocyclic ring optionally substituted with -NR c-R a-Y-R b-(Z)x;
R7 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl,-R a-Y-R b-(Z)x, and -C(O)R d;
R8 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic;
R9 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, allcenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic;
R10 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic; or R8 and R10 are joined to form -Ar1-O-Ar2-, where Ar1 and Ar2 are independently arylene or heteroarylene;
R11 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic, or R10 and R11 are joined, together with the carbon and nitrogen atoms to which they are attached, to form a heterocyclic ring;
R12 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic, -C(O)R d, -C(NH)R d, -C(O)NR c R c, -C(O)OR d, -C(NH)NR c R c and -R a-Y-R b-(Z) x, or R11 and R12 are joined, together with the nitrogen atom to which they are attached, to form a heterocyclic ring;
R13 is selected from the group consisting of hydrogen or -OR14;
R14 is selected from hydrogen, -C(O)R d and a saccharide group;
each R a is independently selected from the group consisting of alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene and substituted alkynylene;
each R b is independently selected from the group consisting of a covalent bond, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene and substituted alkynylene, provided R b is not a covalent bond when Z is hydrogen;
each R c is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic and -C(O)R d;
each R d is independently selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic;
R e is a saccharide group;
each R f is independently alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, or heterocyclic;
R x is an N-linked amino saccharide or an N-linked heterocycle;
X1, X2 and X3 are independently selected from hydrogen or chloro;
each Y is independently selected from the group consisting of oxygen, sulfur, -S-S-, -NR c-, -S(O)-, -SO2-, -NR c C(O)-, -OSO2-, -OC(O)-, -NR c SO2-, -C(O)NR c-, -C(O)O-, -SO2NR c-, -SO2O-, -P(O)(OR c)O-, -P(O)(OR c)NR c-, -OP(O)(OR c)O-,-OP(O)(OR c)NR c-, -OC(O)O-, -NR c C(O)O-, -NR c C(O)NR c-, -OC(O)NR c-, -C(=O)-, and -NR cSO2NR c-;
each Z is independently selected from hydrogen, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclic;
n is 0, I or 2; and x is 1 or 2;
or a pharmaceutically acceptable salt, stereoisomer, or prodrug thereof.
13. The pharmaceutical composition of Claim 1, wherein the glycopeptide antibiotic has formula II:
wherein:
R19 is hydrogen;
R20 is -R a-Y-R b-(Z) x, R f, -C(O)R f, or -C(O)-R a-Y-R b-(Z) x; and R a, Y, R b, Z, x, R f, R3, and R5 are as defined in Claim 7;
or a pharmaceutically acceptable salt, stereoisomer, or prodrug thereof.
wherein:
R19 is hydrogen;
R20 is -R a-Y-R b-(Z) x, R f, -C(O)R f, or -C(O)-R a-Y-R b-(Z) x; and R a, Y, R b, Z, x, R f, R3, and R5 are as defined in Claim 7;
or a pharmaceutically acceptable salt, stereoisomer, or prodrug thereof.
14. A method of treating a mammal having a bacterial disease, the method comprising administering to the mammal a pharmaceutical composition of any one of Claims 1-13.
15. A method of treating a bacterial disease in a mammal, the method comprising administering to the mammal a therapeutically effective amount of a glycopeptide antibiotic in combination with a cyclodextrin.
16. A method for reducing tissue accumulation of a glycopeptide antibiotic when administered to a mammal, the method comprising administering the glycopeptide antibiotic to the mammal in a pharmaceutical composition comprising a cyclodextrin and a therapeutically effective amount of the glycopeptide antibiotic or a pharmaceutically acceptable salt thereof.
17. A method for reducing nephrotoxicity produced by a glycopeptide antibiotic when administered to a mammal, the method comprising administering the glycopeptide antibiotic to the mammal in a pharmaceutical composition comprising a cyclodextrin and a therapeutically effective amount of the glycopeptide antibiotic or a pharmaceutically acceptable salt thereof.
18. A method for reducing histamine release produced by a glycopeptide antibiotic when administered to a mammal, the method comprising administering the glycopeptide antibiotic to the mammal in a pharmaceutical composition comprising a cyclodextrin and a therapeutically effective amount of the glycopeptide antibiotic or a pharmaceutically acceptable salt thereof.
19. A method for reducing vascular irritation produced by a glycopeptide antibiotic when administered to a mammal, the method comprising administering the glycopeptide antibiotic to the mammal in a pharmaceutical composition comprising a cyclodextrin and a therapeutically effective amount of the glycopeptide antibiotic or a pharmaceutically acceptable salt thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2726789A CA2726789A1 (en) | 2000-02-05 | 2001-05-01 | Cyclodextrin containing glycopeptide antibiotic compositions |
Applications Claiming Priority (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20117800P | 2000-05-02 | 2000-05-02 | |
US60/201,178 | 2000-05-02 | ||
US21341700P | 2000-06-22 | 2000-06-22 | |
US21314600P | 2000-06-22 | 2000-06-22 | |
US21341500P | 2000-06-22 | 2000-06-22 | |
US21342800P | 2000-06-22 | 2000-06-22 | |
US21341000P | 2000-06-22 | 2000-06-22 | |
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PCT/US2001/014000 WO2001082971A2 (en) | 2000-05-02 | 2001-05-01 | Cyclodextrin containing glycopeptide antibiotic compositions |
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CA2726789A Division CA2726789A1 (en) | 2000-02-05 | 2001-05-01 | Cyclodextrin containing glycopeptide antibiotic compositions |
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CA2408008A Expired - Lifetime CA2408008C (en) | 2000-02-05 | 2001-05-01 | Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin |
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CA2726789A Abandoned CA2726789A1 (en) | 2000-02-05 | 2001-05-01 | Cyclodextrin containing glycopeptide antibiotic compositions |
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JP (2) | JP4870314B2 (en) |
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AT (1) | ATE416791T1 (en) |
AU (1) | AU2001259306A1 (en) |
BR (1) | BR0110530A (en) |
CA (2) | CA2726789A1 (en) |
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- 2001-05-01 EP EP01932810A patent/EP1278549B1/en not_active Expired - Lifetime
- 2001-05-01 AU AU2001259306A patent/AU2001259306A1/en not_active Abandoned
- 2001-05-01 CN CNB018104746A patent/CN1223378C/en not_active Expired - Lifetime
- 2001-05-01 WO PCT/US2001/014000 patent/WO2001082971A2/en active Application Filing
- 2001-05-01 SI SI200130903T patent/SI1278549T1/en unknown
- 2001-05-01 CA CA2408008A patent/CA2408008C/en not_active Expired - Lifetime
- 2001-05-01 US US09/846,893 patent/US6858584B2/en not_active Expired - Lifetime
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- 2001-05-01 AT AT01932810T patent/ATE416791T1/en not_active IP Right Cessation
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US20060194717A1 (en) | 2006-08-31 |
DE60136926D1 (en) | 2009-01-22 |
CA2408008C (en) | 2011-01-18 |
US8158580B2 (en) | 2012-04-17 |
JP2008231109A (en) | 2008-10-02 |
US20100081609A1 (en) | 2010-04-01 |
US7026288B2 (en) | 2006-04-11 |
US7544364B2 (en) | 2009-06-09 |
AU2001259306A1 (en) | 2001-11-12 |
SI1278549T1 (en) | 2009-04-30 |
US20050026820A1 (en) | 2005-02-03 |
CA2726789A1 (en) | 2001-11-08 |
CN1223378C (en) | 2005-10-19 |
EP1278549A2 (en) | 2003-01-29 |
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