CA2408008A1 - Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin - Google Patents

Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin Download PDF

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Publication number
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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Prior art keywords
substituted
alkynyl
alkyl
alkenyl
cycloalkenyl
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CA002408008A
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French (fr)
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CA2408008C (en
Inventor
J. Kevin Judice
Jeng-Pyng Shaw
Yongqi Mu
Michael W. Conner
John Pace
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Cumberland Pharmaceuticals Inc
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Priority to CA2726789A priority Critical patent/CA2726789A1/en
Publication of CA2408008A1 publication Critical patent/CA2408008A1/en
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Publication of CA2408008C publication Critical patent/CA2408008C/en
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716Glucans
    • A61K31/724Cyclodextrins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/04Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/14Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40Cyclodextrins; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal 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
    • A61K47/69Medicinal 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
    • A61K47/6949Medicinal 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
    • A61K47/6951Medicinal 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0014Skin, i.e. galenical aspects of topical compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0019Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0087Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/02Suppositories; Bougies; Bases therefor; Ovules
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19Particulate 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • A61K9/2018Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841Filling excipients; Inactive ingredients
    • A61K9/4858Organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K9/00Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/006Peptides 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
    • C07K9/008Peptides 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26Carbohydrates, 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.
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.
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.
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.
CA2408008A 2000-02-05 2001-05-01 Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin Expired - Lifetime CA2408008C (en)

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
US60/213,428 2000-06-22
US60/213,410 2000-06-22
US60/213,415 2000-06-22
US60/213,417 2000-06-22
US60/213,146 2000-06-22
US22672700P 2000-08-18 2000-08-18
US60/226,727 2000-08-18
PCT/US2001/014000 WO2001082971A2 (en) 2000-05-02 2001-05-01 Cyclodextrin containing glycopeptide antibiotic compositions

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2726789A Division CA2726789A1 (en) 2000-02-05 2001-05-01 Cyclodextrin containing glycopeptide antibiotic compositions

Publications (2)

Publication Number Publication Date
CA2408008A1 true CA2408008A1 (en) 2001-11-08
CA2408008C CA2408008C (en) 2011-01-18

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ID=27569291

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CA2726789A Abandoned CA2726789A1 (en) 2000-02-05 2001-05-01 Cyclodextrin containing glycopeptide antibiotic compositions
CA2408008A Expired - Lifetime CA2408008C (en) 2000-02-05 2001-05-01 Pharmaceutical compositions containing a glycopeptide antibiotic and a cyclodextrin

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA2726789A Abandoned CA2726789A1 (en) 2000-02-05 2001-05-01 Cyclodextrin containing glycopeptide antibiotic compositions

Country Status (12)

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US (5) US6858584B2 (en)
EP (1) EP1278549B1 (en)
JP (2) JP4870314B2 (en)
CN (1) CN1223378C (en)
AT (1) ATE416791T1 (en)
AU (1) AU2001259306A1 (en)
BR (1) BR0110530A (en)
CA (2) CA2726789A1 (en)
DE (1) DE60136926D1 (en)
ES (1) ES2316445T3 (en)
SI (1) SI1278549T1 (en)
WO (1) WO2001082971A2 (en)

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