US2003114528A1PendingUtilityA1

Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents

62
Priority: Sep 21, 1992Filed: Oct 28, 2002Published: Jun 19, 2003
Est. expirySep 21, 2012(expired)· nominal 20-yr term from priority
Inventors:David F. WoodwardSteven W. AndrewsRobert M. BurkMichael E. Garst
A61K 31/557C07C 35/21A61P 27/02C07C 255/36C07C 215/42A61K 31/559C07C 2601/08C07C 405/00A61K 31/381A61P 27/06C07C 235/34C07C 247/10A61K 31/5585A61K 31/5575
62
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Claims

Abstract

The present invention provides cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl compounds, which may be substituted in the 1-position with amino, amido, ether or ester groups, e.g., a 1-OH cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) compound. The cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma. Moreover, the cyclopentane heptanoic, 2-(cycloalkyl or arylalkyl) compounds of this invention are smooth muscle relaxants with broad application in systemic hypertensive and pulmonary diseases; smooth muscle relaxants with application in gastrointestinal disease, reproduction, fertility, incontinence, shock, etc.

Claims

exact text as granted — not AI-modified
26 . 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:  
       
         
           
           
               
               
           
         
       
       wherein R 1 =hydrogen, a cationic salt moiety, a pharmaceutically acceptable amine moiety or C 1 -C 12  alkyl cycloalkyl or aryl; and R 2 =Cl or CF 3 .  
     
     
         27 . The method of  claim 26 , wherein R 1  is selected from the group consisting of H, CH 3 , CH(CH 3 ) 2  and C(CH 3 ) 3 .  
     
     
         28 . The method of  claim 26 , wherein R 1  is selected from the group consisting of Na +  and CH 3  N + (CH 2 OH) 3 .  
     
     
         29 . The method of  claim 26 , wherein R 2  is Cl.  
     
     
         30 . The method of  claim 27 , wherein R 2  is CF 3 .  
     
     
         31 . The method of  claim 26 , wherein between about 0.001 and about 1000 μg/eye of a compound of formula (I) is administered.  
     
     
         32 . The method of  claim 31 , wherein between about 0.01 and about 100 μg/eye of a compound of formula (I) is administered.  
     
     
         33 . The method of  claim 31 , wherein between about 0.05 and about 10 μg/eye of a compound of formula (I) is administered.  
     
     
         34 . A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension in primates, comprising topically a therapeutically effective amount of a compound of formula:  
       
         
           
           
               
               
           
         
       
       wherein R 1 =hydrogen, a cationic salt moiety, a pharmaceutically acceptable amine moiety or C 1 -C 12  alkyl cycloalkyl or aryl; and R 2 =Cl or CF 3 .  
     
     
         35 . The composition of  claim 34 , wherein R 1  is selected from the group consisting of H, CH 3 , CH(CH 3 ) 2  and C(CH 3 ) 3 .  
     
     
         36 . The composition of  claim 34 , wherein R 1  is selected from the group consisting of Na +  and CH 3 N + (CH 2 OH) 3 .  
     
     
         7 . The method of claim  6 , wherein between about 0.01 and about 100 μg/eye of a compound of formula (I) is administered.  
     
     
         8 . The method of claim  6 , wherein between about 0.05 and about 10 μg/eye of a compound of formula (I) is administered.  
     
     
         9 . A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension in primates, comprising topically a therapeutically effective amount of a compound of formula:  
       
         
           
           
               
               
           
         
       
       wherein R 1 =hydrogen, a cationic salt moiety, a pharmaceutically acceptable amine moiety or C 1 -C 12  alkyl cycloalkyl or aryl; and R 2 =Cl or CF 3 .  
     
     
         10 . The composition of  claim 9 , wherein R 1  is selected from the group consisting of H, CH 3 , CH(CH 3 ) 2  and C(CH 3 ) 3 .  
     
     
         11 . The composition of  claim 9 , wherein R 1  is selected from the group consisting of Na +  and CH 3 N + (CH 2 OH) 3 .  
     
     
         12 . The composition of  claim 9 , wherein R 2  is Cl.  
     
     
         13 . The composition of  claim 9 , wherein R 2  is CF 3 .  
     
     
         14 . The composition of  claim 9 , wherein between about 0.001 and about 100 μg/eye of a compound of formula (I) is administered.  
     
     
         15 . The composition of  claim 14 , wherein between about 0.01 and about 100 μg/eye of a compound of formula (I) is administered.  
     
     
         16 . The composition of  claim 15 , wherein between about 0.05 and about 10 μg/eye of a compound of formula (I) is administered.  
     
     
         17 . 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:  
       
         
           
           
               
               
           
         
       
       wherein R 1 =a pharmaceutically acceptable ester moiety; and R 2 =Cl or CF 3 .  
     
     
         18 . The method of  claim 17 , wherein R 2  is Cl.  
     
     
         19 . The method of  claim 17 , wherein R 2  is CF 3 .  
     
     
         20 . The method of  claim 17 , wherein between about 0.001 and about 1000 μg/eye of a compound of formula (I) is administered.  
     
     
         21 . A method of treating glaucoma and ocular hypertension which comprises topically administering to the affected eye a therapeutically effective amount of cyclopentane heptenoic acid, 5-cis-2-(3-α-hydroxy-4-m-chlorophenoxy-1-trans-butenyl)-3,5-dihydroxy 1 α ,2 β ,3 α ,5 α ].  
     
     
         22 . A method of treating glaucoma and ocular hypertension which comprises topically administering to the affected eye a therapeutically effective amount of fluprostenol.  
     
     
         23 . A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension in humans, comprising a therapeutically effective amount of fluprostenol.  
     
     
         37 . The composition of  claim 34 , wherein R 2  is Cl.  
     
     
         38 . The composition of  claim 34 , wherein R 2  is CF 3 .  
     
     
         39 . The composition of  claim 34 , wherein between about 0.001 and about 100 μg/eye of a compound of formula (I) is administered.  
     
     
         40 . The composition of  claim 39 , wherein between about 0.01 and about 100 μg/eye of a compound of formula (I) is administered.  
     
     
         41 . The composition of  claim 40 , wherein between about 0.05 and about 10 μg/eye of a compound of formula (I) is administered.  
     
     
         42 . 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:  
       
         
           
           
               
               
           
         
       
       wherein R 1 =a pharmaceutically acceptable ester moiety; and R 2 =C 1  or CF 3 .  
     
     
         43 . The method of  claim 42 , wherein R 2  is Cl.  
     
     
         44 . The method of  claim 42 , wherein R 2  is CF 3 .  
     
     
         45 . The method of  claim 42 , wherein between about 0.001 and about 1000 μg/eye of a compound of formula (I) is administered.  
     
     
         46 . A method of treating glaucoma and ocular hypertension which comprises topically administering to the affected eye a therapeutically effective amount of cyclopentane heptenoic acid, 5-cis-2-(3-a-hydroxy-4-m-chlorophenoxy-1-trans-butenyl)-3,5-dihydroxy 1 α ,2 β ,3 α ,5 α ].  
     
     
         47 . A method of treating glaucoma and ocular hypertension which comprises topically administering to the affected eye a therapeutically effective amount of fluprostenol.  
     
     
         48 . A topical ophthalmic composition for the treatment of glaucoma and ocular hypertension in humans, comprising a therapeutically effective amount of fluprostenol.

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