1-Substituted-3,4-epoxypyrrolidines
AssigneeA. H. Robins Company, Incorporated
InventorsDavid A. Walsh, William J. Welstead, Jr.
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Abstract
3,4-Epoxypyrrolidines substituted in the 1-position with alkyl, cycloalkyl and phenylalkyl are disclosed which have pharmaceutical application in cataract prevention in animals and as intermediates in preparation of trans-3-aryloxy-4-hydroxypyrrolidines. The epoxypyrrolidines are prepared by a novel route involving chlorination of pyrrolines in aqueous medium.
Claims22
A compound selected from 1-substituted-3,4-epoxypyrrolidines having the formula:
- ##STR4## wherein R is loweralkyl, cycloalkyl having 3 to 9 carbon atoms or phenylalkyl wherein the alkyl moiety includes radicals of up to 4 carbon atoms and the acid addition salts thereof.
A method for the prevention or amelioration of diabetes complications consisting of cataracts in a diabetic animal which comprises administering to said animal an effective amount of a compound having the formula:
- ##STR5## wherein R is loweralkyl, cycloalkyl having 3 to 9 carbon atoms or phenylalkyl wherein the alkyl moiety includes radicals of up to 4 carbon atoms and the pharmaceutically acceptable addition salts thereof.
A pharmaceutical composition for the prevention or amelioration of diabetic complications consisting of cataracts in a diabetic animal comprising (a) from 5 milligrams to 100 milligrams of a compound selected from 1-substituted -3,4-epoxypyrrolidines having the formula:
- ##STR6## wherein R is loweralkyl, cycloalkyl having 3 to 9 carbon atoms or phenylalkyl wherein the alkyl moiety includes radicals of up to 4 carbon atoms and the pharmaceutically acceptable addition salts thereof, and (b) a pharmaceutically acceptable carrier.
A process for the preparation of 1-substituted-3,4-epoxypyrrolidines having the formula:
- ##STR7## wherein R is loweralkyl, cycloalkyl and phenylalkyl which comprises the steps of (1) reacting a 1-substituted .DELTA..sup.3 pyrroline having the formula:
- ##STR8## with chlorine in aqueous acidic medium to form 1-substituted-3-hydroxy-4-chloropyrrolidine having the formula:
- ##STR9## wherein R is as defined above and (2) causing epoxidation by reaction with base to form said 1-substituted-3,4-epoxypyrrolidines.
Dependencies are inferred from the claim text.