CA2369457A1 - Ocular treatment using cyclosporin-a derivatives - Google Patents

Ocular treatment using cyclosporin-a derivatives Download PDF

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Publication number
CA2369457A1
CA2369457A1 CA002369457A CA2369457A CA2369457A1 CA 2369457 A1 CA2369457 A1 CA 2369457A1 CA 002369457 A CA002369457 A CA 002369457A CA 2369457 A CA2369457 A CA 2369457A CA 2369457 A1 CA2369457 A1 CA 2369457A1
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CA
Canada
Prior art keywords
nr1r2
pharmaceutically acceptable
acceptable excipient
alkyl
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002369457A
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French (fr)
Other versions
CA2369457C (en
Inventor
Michael E. Garst
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Allergan Inc
Original Assignee
Allergan Sales, Inc.
Michael E. Garst
Allergan Sales, Llc
Allergan, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Allergan Sales, Inc., Michael E. Garst, Allergan Sales, Llc, Allergan, Inc. filed Critical Allergan Sales, Inc.
Publication of CA2369457A1 publication Critical patent/CA2369457A1/en
Application granted granted Critical
Publication of CA2369457C publication Critical patent/CA2369457C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A61K38/13—Cyclosporins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/04—Artificial tears; Irrigation solutions
    • 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
    • A61K9/0048—Eye, e.g. artificial tears

Abstract

A method of treating a disorder in an eye, for example, an aqueous deficient dry eye state, phacoanaphylactic endophthalmitis, or uveitis, is provided. The method generally includes administering a therapeutically effective amount of a certain cyclosporin A derivative topically to the affected eye. The derivative may be administered as a solution, suspension or ointment in a pharmaceutically acceptable excipient.

Claims (18)

What is claimed is:
1. A method for the treatment of an aqueous deficient dry eye state, uveitis or phacoanaphylactic endophthalmitis in an eye, said method comprising administering, topically to the eye, a therapeutically effective amount of a cyclosporin A derivative selected from the group consisting of compounds represented by the general formulas:

wherein Me is methyl; Alk is 2-6C alkylene or 3-6C cycloalkylene; R is OH, COOH, alkoxycarbonyl,-NR1R2 or -N(R3)-(CH2)n-NR1R2; wherein R1, R2 is H, alkyl, 3-6C cycloalkyl, phenyl (optionally substituted by halo, alkoxy, alkoxycarbonyl, amino, alkylamino or dialkylamino), benzyl or saturated or unsaturated heterocyclyl having 5 or 6 members and 1-3 heteroatoms; or NR1R2 is a 5 or 6 membered heterocycle which may contain a further N, O or S heteroatom and may be alkylated; R3 is H or alkyl and n is 2-4; and alkyl moieties contain 1-4C.
2. The method of claim 1 wherein 0.01 to 50wt% of the compound in a pharmaceutically acceptable excipient is used.
3. The method of claim 2 wherein 0.1 to 20wt% of the compound in a pharmaceutically acceptable excipient is used.
4. The method of claim 2 wherein the pharmaceutically acceptable excipient is selected from the group consisting of animal oil and vegetable oil.
5. The method of claim 2 wherein the pharmaceutically acceptable excipient is selected from the group consisting of olive oil, arachis oil, castor oil, mineral oil, petroleum jelly, dimethyl sulphoxide, an alcohol, silicone fluid and mixtures thereof.
6. The method of claim 2 wherein the pharmaceutically acceptable excipient is selected from the group consisting of comprises polyvinyl alcohol, polyoxyethylated castor oil or methyl cellulose and mixtures thereof.
7. The method of claim 5 wherein the pharmaceutically acceptable excipient is dimethyl sulphoxide.
A method for the treatment of a disorder caused by excessive immune activity in the anterior segment, posterior segment or the vitreous body of an eye, which comprises topically administering to said eye, a cyclosporin A derivative selected from the group consisting of compounds represented by the general formulas wherein Me is methyl; Alk is 2-6C alkylene or 3-6C cycloalkylene; R is OH, COOH, alkoxycarbonyl,-NR1R2 or -N(R3)-(CH2)n - NR1R2; wherein R1, R2 is H, alkyl, 3-6C cycloalkyl, phenyl (optionally substituted by halo, alkoxy, alkoxycarbonyl, amino, alkylamino or dialkylamino), benzyl or saturated or unsaturated heterocyclyl having 5 or 6 members and 1 -3 heteroatoms; or NR1R2 is a 5 or 6 membered heterocycle which may contain a further N, O or S heteroatom and may be alkylated; R3 is H or alkyl and n is 2-4; and alkyl moieties contain 1-4C, the compound being administered in an amount sufficient to reduce said immune activity.
9. A method for enhancing or restoring lacrimal gland tearing in an eye, the method comprising administering topically to the eye, in a pharmaceutically acceptable excipient, a cyclosporin A derivative selected from the group consisting of compounds represented by the general formulas wherein Me is methyl; Alk is 2-6C alkylene or 3-6C cycloalkylene; R is OH, COOH, alkoxycarbonyl,-NR1R2 or -N(R3)-(CH2)n - NR1R2; wherein R1, R2 is H, alkyl, 3-6C cycloalkyl, phenyl (optionally substituted by halo, alkoxy, alkoxycarbonyl, amino, alkylamino or dialkylamino), benzyl or saturated or unsaturated heterocyclyl having 5 or 6 members and 1-3 heteroatonis; or NR1R2 is a 5 or 6 membered heterocycle which may contain a further N, O or S heteroatom and may be alkylated; R3 is H or alkyl and n is 2-4; and alkyl moieties contain 1-4C.
10. The method according to claim 9 wherein the compound is administered as a solution, suspension or ointment comprising 0.01 to 50 weight percent of the compound.
11. The method according to claim 10 wherein the compound is administered in an amount of 0.1 to 20 weight percent.
12. The method according to claim 9 wherein the pharmaceutically acceptable excipient is selected from the group consisting of olive oil, arachis oil, castor oil, polyoxyethylated castor oil, mineral oil, petroleum jelly, dimethyl sulphoxide, an alcohol, liposome, silicone fluid and mixtures thereof.
13. The method of claim 12 wherein the pharmaceutically acceptable excipient is dimethyl sulphoxide.
14. A method for treating a disorder exacerbated by deficient tear production in a patient, the method comprising administering topically to the eye, in a pharmaceutically acceptable excipient, a cyclosporin A derivative selected from the group consisting of compounds represented by the general formulas wherein Me is methyl; Alk is 2-6C alkylene or 3-6C cycloalkylene; R is OH, COOH, alkoxycarbonyl,-NR1R2 or -N(R3)-(CH2)n - NR1R2; wherein R1, R2 is H, alkyl, 3-6C cycloalkyl, phenyl (optionally substituted by halo, alkoxy, alkoxycarbonyl, amino, alkylamino or dialkylamino), benzyl or saturated or unsaturated heterocyclyl having 5 or 6 members and 1-3 heteroatoms; or NR1R2 is a 5 or 6 membered heterocycle which may contain a further N, O or S heteroatom and may be alkylated; R3 is H or alkyl and n is 2-4; and alkyl moieties contain 1-4C.
15. The method according to claim 14 wherein the compound is administered as a solution, suspension or ointment comprising 0.01 to 50 weight percent of the compound.
16. The method according to claim 15 wherein the compound is administered in an amount of 0.1 to 20 weight percent.
17. The method according to claim 14 wherein the pharmaceutically acceptable excipient is selected from the group consisting of olive oil, arachis oil, castor oil, polyoxyethylated castor oil, mineral oil, petroleum jelly, dimethyl sulphoxide, an alcohol, liposome, silicone fluid and mixtures thereof.
18. The method of claim 17 wherein the pharmaceutically acceptable excipient is dimethyl sulphoxide.
CA2369457A 1999-04-13 2000-04-04 Ocular treatment using cyclosporin-a derivatives Expired - Fee Related CA2369457C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/290,833 1999-04-13
US09/290,833 US6254860B1 (en) 1999-04-13 1999-04-13 Ocular treatment using cyclosporin-A derivatives
PCT/US2000/008877 WO2000061168A1 (en) 1999-04-13 2000-04-04 Ocular treatment using cyclosporin-a derivatives

Publications (2)

Publication Number Publication Date
CA2369457A1 true CA2369457A1 (en) 2000-10-19
CA2369457C CA2369457C (en) 2010-08-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2369457A Expired - Fee Related CA2369457C (en) 1999-04-13 2000-04-04 Ocular treatment using cyclosporin-a derivatives

Country Status (11)

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US (2) US6254860B1 (en)
EP (1) EP1169050B1 (en)
JP (1) JP4711516B2 (en)
AT (1) ATE423566T1 (en)
AU (1) AU759753B2 (en)
CA (1) CA2369457C (en)
DE (1) DE60041637D1 (en)
DK (1) DK1169050T3 (en)
ES (1) ES2319853T3 (en)
NZ (1) NZ514105A (en)
WO (1) WO2000061168A1 (en)

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Also Published As

Publication number Publication date
EP1169050B1 (en) 2009-02-25
DE60041637D1 (en) 2009-04-09
WO2000061168A1 (en) 2000-10-19
US6254860B1 (en) 2001-07-03
CA2369457C (en) 2010-08-10
NZ514105A (en) 2005-01-28
DK1169050T3 (en) 2009-04-14
US6350442B2 (en) 2002-02-26
US20010036449A1 (en) 2001-11-01
AU4193500A (en) 2000-11-14
AU759753B2 (en) 2003-05-01
ATE423566T1 (en) 2009-03-15
ES2319853T3 (en) 2009-05-14
JP2002541207A (en) 2002-12-03
EP1169050A1 (en) 2002-01-09
JP4711516B2 (en) 2011-06-29

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