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US 5,665,773 AGranted
Cloprostenol and fluprostenol analogues and their use to treat glaucoma and ocular hypertension
AssigneeAlcon Laboratories, Inc.
InventorsPeter G. Klimko, John E. Bishop, Verney L. Sallee, Paul W. Zinke
Life of this patent
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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.
Claims20
A method of treating glaucoma and ocular hypertension which comprises topically administering to the affected eye a therapeutically effective amount of a compound of formula:
- ##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.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.sup.1 C.sub.1 -C.sub.12 straight-chain or branched acyl;
- and when R.sub.2 =R.sub.3 =H, then R.sub.1.sup.1 a cationic salt moiety;
- and
- with the further proviso that the following compounds be excluded:
- cyclopentane heptenol-5-cis-2-(3-.alpha.hydroxy-4-m-chlorophenoxy-1-transbutenyl)-3,5-d ihydroxy;
- and compounds of the formula:
- ##STR12## wherein R.sub.1 =hydrogen, a cationic salt moiety, C.sub.1 -C.sub.12 straight chain or branched alkyl or C.sub.3 -C.sub.8 cycloalkyl;
- and
- Z=Cl or CF.sub.3.
23 more elements
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 of formula:
- ##STR13## 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 a
- 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.sup.1 C.sub.1 -C.sub.12 straight-chain or branched acyl;
- and when R.sub.2 =R.sub.3 =H, then R.sub.1.sup.1 a cationic salt moiety;
- and
- with the further proviso that the following compounds be excluded:
- cyclopentane heptenol-5-cis-2-(3-.alpha.hydroxy-4-m-chlorophenoxy-1-transbutenyl)-3,5 dihydroxy;
- and compounds of the formula:
- ##STR14## wherein R.sub.1 =hydrogen, a cationic salt moiety, C.sub.1 -C.sub.12 straight chain or branched alkyl or C.sub.3 C.sub.8 cycloalkyl;
- and
- Z=Cl or CF.sub.3.
23 more elements
A compound of formula:
- ##STR15## 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;
- ---- 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.
16 more elements
Dependencies are inferred from the claim text.