Use of cloprostenol and fluprostenol analogues to treat glaucoma and ocular hypertension
AssigneeAlcon Laboraties, Inc.
InventorsPeter G. Klimko, John E. Bishop, Verney L. Sallee, Paul W. Zinke
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Abstract
Disclosed is the use of cloprostenol and fluprostenol analogues for the treatment of glaucoma and ocular hypertension. Also disclosed are ophthalmic compositions comprising said compounds.
Claims22
A method of treating glaucoma and ocular hypertension which comprises topically administering to the affected eye a composition comprising a therapeutically effective amount of a compound having the absolute stereochemical structure of the following formula (IV), and being substantially free of the enantiomer of said compound:
- ##STR11## wherein:
- R.sub.1 =H;
- C.sub.1 -C.sub.12 straight-chain or branched alkyl;
- C.sub.1 -C.sub.12 straight-chain or branched acyl;
- C.sub.3 -C.sub.3 cycloalkyl;
- or a cationic salt moiety;
- R.sub.2, R.sub.3 =H, or C.sub.1 -C.sub.5 straight-chain or branched alkyl;
- or R.sub.2 and R.sub.3 taken together may represent O;
- X=O, S, or CH.sub.2 ;
- represents any combination of a single bond, or a cis or trans double bond for the alpha (upper) chain;
- and a single bond or trans double bond for the omega (lower) chain;
- R.sub.9 =H, C.sub.1 -C.sub.10 straight-chain or branched alkyl, or C.sub.1 -C.sub.10 straight-chain or branched acyl;
- R.sub.11 =H, C.sub.1 -C.sub.10 straight-chain or branched alkyl, or C.sub.1 -C.sub.10 straight-chain or branched acyl;
- Y=O;
- or H and OR.sub.15 in either configuration wherein R.sub.15 =H, C.sub.1 -C.sub.10 straightchain or branched alkyl, or C.sub.1 -C.sub.10 straight-chain or branched acyl;
- and
- Z=Cl or CF.sub.3 ;
- with the proviso that when R.sub.2 and R.sub.3 taken together represent O, then R.sub.1 .noteq.C.sub.1 -C.sub.12 straight-chain or branched acyl;
- and when R.sub.2 =R.sub.3 =H, then R.sub.1 .noteq.a cationic salt moiety;
- and
- with the further proviso that the following compound be excluded:
- cyclopentane heptenol-5-cis-2-(3-.alpha.hydroxy-4-m-chlorophenoxy-1-transbutenyl)-3,5 dihydroxy, 1.sub..alpha., 2.sub..beta., 3.sub..alpha., 5.sub..alpha. !.
A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension comprising an ophthalmically acceptable carrier and a therapeutically effective amount of a compound having the absolute stereochemical structure of the following formula (IV), and being substantially free of the enantiomer of said compound:
- ##STR12## wherein:
- R.sub.1 =H;
- C.sub.1 -C.sub.12 straight-chain or branched alkyl;
- C.sub.1 -C.sub.12 straight-chain or branched acyl;
- C.sub.3 -C.sub.8 cycloalkyl;
- or a cationic salt moiety;
- R.sub.2, R.sub.3 =H, or C.sub.1 -C.sub.5 straight-chain or branched alkyl;
- or R.sub.2 and R.sub.3 taken together may represent O;
- X=O, S, or CH.sub.2 ;
- represents any combination of a single bond, or a cis or trans double bond for the alpha (upper) chain;
- and a single bond or trans double bond for the omega (lower) chain;
- R.sub.9 =H, C.sub.1 -C.sub.10 straight-chain or branched alkyl, or C.sub.1 -C.sub.10 straight-chain or branched acyl;
- R.sub.11 =H, C.sub.1 -C.sub.10 straight-chain or branched alkyl, or C.sub.1 -C.sub.10 straight-chain or branched acyl;
- Y=O;
- or H and OR.sub.15 in either configuration wherein R.sub.15 =H, C.sub.1 -C.sub.10 straight-chain or branched alkyl, or C.sub.1 -C.sub.10 straight-chain or branched acyl;
- and
- Z=Cl or CF.sub.3 ;
- with the proviso that when R.sub.2 and R.sub.3 taken together represent O, then R.sub.1 .noteq.C.sub.1 -C.sub.12 straight-chain or branched acyl;
- and when R.sub.2 =R.sub.3 =H, then R.sub.1 .noteq.a cationic salt moiety;
- and
- with the further proviso that the following compound be excluded:
- cyclopentane heptenol-5-cis-2-(3-.mu.hydroxy4-m-chlorophenoxy-l1-transbutenyl)-3,5 dihydroxy, 1.sub..alpha., 2.sub..beta., 3.sub..alpha., 5.sub..alpha. !.
Dependencies are inferred from the claim text.