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US 5,698,733 AGranted
Use of 9-deoxy prostaglandin derivatives to treat glaucoma
AssigneeAlcon Laboratories, Inc.
InventorsMark R. Hellberg, Thomas R. Dean, Paul W. Zinke, Robert D. Selliah, John E. Bishop
Life of this patent
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Abstract
Disclosed are 9-deoxyprostaglandins which are useful in the treatment of glaucoma and ocular hypertension. Some of these 9-deoxyprostaglandins are novel. Also disclosed are ophthalmic, pharmaceutical compositions comprising such prostaglandins.
Claims15
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:
- ##STR12## wherein:
- Y=C(O)NR.sub.1 R.sub.2, CH.sub.2 OR.sub.3, CH.sub.2 NR.sub.1 R.sub.2, CO.sub.2 R.sub.1, CO.sub.2 M where M is a cationic salt moiety;
- R.sub.1, R.sub.2 (same or different)=H, C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- R, R.sub.3 (same or different)=C(O)R.sub.4, H;
- R.sub.4 =C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- X=O, S(O).sub.n, CH.sub.2 ;
- n=0, 1, or 2;
- A=CH.sub.2 CH.sub.2, cis or trans CH.dbd.CH, or C.tbd.C;
- Z=CH.sub.2 CH.sub.2, trans CH.dbd.CH, or C.tbd.C;
- W=(CH.sub.2).sub.m, Aryl, (CH.sub.2).sub.m OAryl where m=1-6 and Aryl=phenyl, optionally substituted with halogen, hydroxy, alkoxy, haloalkyl, amino, or acylamino;
- or ##STR13## where V=H, alkyl, halogen, hydroxy, alkoxy, acryloxy, haloalkyl, amino, acylamino, and L=CH.sub.2, O, S(O).sub.m, CH.sub.2 CH.sub.2, CH.sub.2 O, NR, CH.dbd.N, CH.sub.2 S(O).sub.m, CH.dbd.CH, CH.sub.2 NR where m=0-2 and R is as defined above.
8 more elements
A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension, said composition comprising an ophthalmically acceptable vehicle and a therapeutically effective amount of a compound of formula:
- ##STR14## wherein:
- Y=C(O)NR.sub.1 R.sub.2, CH.sub.2 OR.sub.2, CH.sub.2 NR.sub.1 R.sub.2, CO.sub.2 R.sub.1, CO.sub.2 M where M is a cationic salt moiety;
- R.sub.1, R.sub.2 (same or different)=H, C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- R, R.sub.3 (same or different)=C(O)R.sub.4, H;
- R.sub.4 =C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- X=O, S(O).sub.n, CH.sub.2 ;
- n=0, 1, or 2;
- A=CH.sub.2 CH.sub.2 cis or trans CH.dbd.CH, or C.tbd.C;
- Z:
- CH.sub.2 CH.sub.2, trans CH.dbd.CH, or C.tbd.C;
- W=(CH.sub.2).sub.m Aryl, (CH.sub.2).sub.m OAryl where m=1-6 and Aryl=phenyl, optionally substituted with halogen, hydroxy, alkoxy, haloalkyl, amino, or acylamino;
- or ##STR15## where V=H, alkyl, halogen, hydroxy, alkoxy, acryloxy, haloalkyl, amino, acylamino, and L=CH.sub.2, O, S(O).sub.m, CH.sub.2 CH.sub.2, CH.sub.2 O, NR, CH.dbd.N, CH.sub.2 S(O).sub.m, CH.dbd.CH, CH.sub.2 NR where m=0-2 and R is as defined above.
9 more elements
A compound of formula:
- ##STR16## wherein:
- Y=C(O)NR.sub.1 R.sub.2, CH.sub.2 OR.sub.3, or CH.sub.2 NR.sub.1 R.sub.2 ;
- R.sub.1, R.sub.2 (same or different)=H, C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- R, R.sub.3 (same or different)=C(O)R.sub.4, H;
- R.sub.4 =C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- X=O, S(O).sub.n, or CH.sub.2 ;
- n=0, 1, or2;
- A=CH.sub.2 CH.sub.2, cis or trans CH.dbd.CH, or C.tbd.C;
- Z=CH.sub.2 CH.sub.2, trans CH.dbd.CH, or C.tbd.C;
- W=(CH.sub.2).sub.m Aryl or (CH.sub.2).sub.m OAryl;
- m=1-6;
- and
- Aryl=phenyl, optionally substituted with halogen, hydroxy, alkoxy, haloalkyl, amino, or acylamino;
- with the proviso that the following compounds be excluded:
- ##STR17## wherein:
- A=CH.sub.2 CH.sub.2 or CH.dbd.CH;
- Z=CH.sub.2 CH.sub.2 or trans- CH.dbd.CH;
- W=CH.sub.2 OAryl or (CH.sub.2).sub.m Aryl, wherein m=2 or 3, and Aryl=phenyl, optionally substituted with halogen, hydroxy, alkoxy, or haloalkyl.
15 more elements
A compound of the formula:
- ##STR18## wherein:
- Y=C(O)NR.sub.1 R.sub.2, CH.sub.2 OR.sub.3, CH.sub.2 NR.sub.1 R.sub.2, CO.sub.2 R.sub.1, CO.sub.2 M where M is a cationic salt moiety;
- R.sub.1, R.sub.2 (same or different)=H, C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- R, R.sub.3 (same or different)=C(O)R.sub.4, H;
- R.sub.4 =C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl;
- X=O, S(O).sub.n, CH.sub.2 ;
- n=0, 1, or 2;
- A=CH.sub.2 CH.sub.2, cis or trans CH.dbd.CH, or C.tbd.C;
- Z=CH.sub.2 CH.sub.2, trans CH.dbd.CH, or C.tbd.C;
- ##STR19## V=H, alkyl, halogen, hydroxy, alkoxy, acryloxy, haloalkyl, amino, acylamino, and L=CH.sub.2, O, S(O).sub.m, CH.sub.2 CH.sub.2, CH.sub.2 O, NR, CH.dbd.N, CH.sub.2 S(O).sub.m, CH.dbd.CH, CH.sub.2 NR where m=0-2 and R is as defined above.
7 more elements
Dependencies are inferred from the claim text.