6,9-nitrilo-prostaglandin analogues

C - Chemistry – Metallurgy – 07 – D

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260/235.01

C07D 209/52 (2006.01) C07C 405/00 (2006.01)

Patent

CA 1154442

A B S T R A C T 6 9 -NITRILO-PROSTAGLANDIN ANALOGUES" Prostaglandin I2 analogues of the general formula: Image II [wherein R1 represents a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aralkyl group containing from 7 to 13 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group containing from 1 to 4 carbon atoms, a phenyl group unsubstituted or substituted by at least one halogen atom, trifluoromethyl or phenyl group, or by at least one alkyl, alkoxy or alkylthio group containing from 1 to 4 carbon atoms, or represents a group Image , Image or Image , in which m represents an integer of 1 to 12, n represents an integer of 2 to 12, R6 , R8 and R9 , which may be the same or different, each represent an alkyl group containing from 1 to 4 carbon atoms, and R7 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, R2 represents a hydrogen atom, or a methyl or ethyl group, R3 represents an alkyl group containing from 1 to 4 carbon atoms, R4 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, R5 represents an alkyl group containing from 1 to 10 carbon atoms, Y represents ethylene or trans-vinylene, the hydroxy group attached to the C-ll carbon atom is in a-configuration, and the wavy line Image attached to the C-15 carbon atom is in .alpha.- or .beta.-configuration or a mixture thereof]and non-toxic acid addition salts thereof and, when Rl represents a hydrogen atom, non-toxic salts thereof are new compounds possessing pharmacological properties typical of the prostaglandins.

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