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US 6,649,653 B1Granted
15-fluoro prostaglandins as ocular hypotensives
AssigneeAlcon Manufacturing, Ltd.
InventorsPeter G. Klimko, Mark R. Hellberg, Paul W. Zinke
Life of this patent
Estimating the term…
Abstract
15-Fluoro substituted analogs of PGF2α and methods of their use in treating glaucoma and ocular hypertension are disclosed.
Claims25
A method of treating glaucoma or ocular hypertension in a patient, which comprises administering to the patient a pharmaceutically effective amount of a compound of formula I:
- wherein:
- R1=CO2R, CONR4R5, CH2OR6, or CH2NR7R8;
- where
- R=H or cationic salt moiety, or CO2R=ophthalmically acceptable ester moiety;
- R4, R5=same or different=H or alkyl;
- R6=H, acyl, or alkyl;
- R7,
- R8=same or different=H, acyl, or alkyl;
- with the proviso that if one of R7,
- R8=acyl, then the other=H or alkyl;
- n=0 or 2;
- =single or non-cumulated double bond, with the provisos that a double bond between carbons 4 and 5 may not be of the trans configuration;
- and that a double bond between carbons 13 and 14 may not be of the cis configuration;
- R2, R3=same or different=H, alkyl, or acyl;
- D, D1=different=H and fluorine;
- X=(CH2)q or (CH2)qO;
- where q=1-6;
- and
- Y=a phenyl ring optionally substituted with alkyl, halo, trihalomethyl, alkoxy, acyl, acyloxy, amino, alkylamino, acylamino, or hydroxy;
- or
- X—Y=(CH2)pY1;
- where p=0-6;
- and
- wherein:
- W=CH2, O, S(O)m, NR9, CH2CH2, CH═CH, CH2O, CH2S(O)m, CH═N, or CH2NR9;
- where m=0-2, and R9=H, alkyl, or acyl;
- Z=H, alkyl, alkoxy, acyl, acyloxy, halo, trihalomethyl, amino, alkylamino, acylamino, or hydroxy;
- and
- =single or double bond.
26 more elements
A compound of formula I:
- wherein:
- R1=CO2R, CONR4R5, CH2OR6, or CH2NR7R8;
- where R=H or cationic salt moiety or CO2R=pharmaceutically acceptable ester moiety;
- R4, R5=same or different=H or alkyl;
- R6 H, acyl, or alkyl;
- R7, R8 =same or different=H, acyl, or alkyl;
- with the proviso that if one of R7, R8=acyl, then the other=H or alkyl;
- n=0 or 2;
- =single or non-cumulated double bond, with the provisos that a double bond between carbons 4 and 5 may not be of the trans configuration;
- and that a double bond between carbons 13 and 14 may not be of the cis configuration;
- R2, R3=same or different=H, alkyl, or acyl;
- D, D1=different=H and fluorine;
- X=(CH2)q or (CH2)qO;
- where q=1-6;
- and
- Y=a phenyl ring optionally substituted with alkyl, halo, trihalomethyl, alkoxy, acyl, acyloxy, amino, alkylamino, acylamino, or hydroxy;
- or
- X—Y=(CH2)pY1;
- where p=0-6;
- and
- wherein:
- W=CH2, O, S(O)m, NR9, CH2CH2, CH═CH, CH2O, CH2S(O)m, CH═N, or CH2NR9;
- where m=0-2, and R9=H, alkyl, or acyl;
- Z=H, alkyl, alkoxy, acyl, acyloxy, halo, trihalomethyl, amino, alkylamino, acylamino, or hydroxy;
- and
- =single or double bond.
23 more elements
A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension, comprising a compound of formula I:
- wherein:
- R1=CO2R, CONR4R5, CH2OR6, or CH2NR7R8;
- where
- R=H or cationic salt moiety, or CO2R=ophthalmically acceptable ester moiety;
- R4, R5=same or different=H or alkyl;
- R6=H, acyl, or alkyl;
- R7, R8=same or different=H, acyl, or alkyl;
- with the proviso that if one of R7, R8=acyl, then the other=H or alkyl;
- n=0 or 2;
- =single or non-cumulated double bond, with the provisos that a double bond between carbons 4 and 5 may not be of the trans configuration;
- and that a double bond between carbons 13 and 14 may not be of the cis configuration;
- R2, R3=same or different=H, alkyl, or acyl;
- D, D1=different=H and fluorine;
- X=(CH2)q or (CH2)qO;
- where q=1-6;
- and
- Y=a phenyl ring optionally substituted with alkyl, halo, trihalomethyl, alkoxy, acyl, acyloxy, amino, alkylamino, acylamino, or hydroxy;
- or
- X—Y=(CH2)pY1;
- where p=0-6;
- and
- wherein:
- W=CH2, O, S(O)m, NR9, CH2CH2, CH═CH, CH2O, CH2S(O)m, CH═N, or CH2NR9;
- where m=0-2, and R9=H, alkyl, or acyl;
- Z=H, alkyl, alkoxy, acyl, acyloxy, halo, trihalomethyl, amino, alkylamino, acylamino, or hydroxy;
- and
- =single or double bond;
- and
- an ophthalmically acceptable vehicle therefor.
26 more elements
Dependencies are inferred from the claim text.