16-AMINO-17-PHENYL-18,19,20-TRINOR-PROSTA-GLANDIN DERIVATIVES

• Main Authors: GABRIELLA MEZEI, EVA TOTH-SARUDY, GABOR AMBRUS, IMRE MORAVCSIK, GYORGY CSEH, JANOS BORVENDEG
• Format: Patent
• Language: English
• Published: 17.06.1982
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

The invention relates to new 16-amino-18,19,20-trinor-prostaglandin derivatives of general formula I, having at C-17 a substituted or unsubstituted phenyl group, wherein C-15 and C-16 may have either S or R configuration, Y stands for a hydrogen atom or a lower alkyl group, W stands for a hydrogen atom, halogen atom, hydroxy group, lower alkyl or alkoxy group, and their acid addition salts. These compounds can be prepared by removing the ester group and the p-nitrobenzyloxycarbonyl protective group of a 9 alpha ,11 alpha ,15-trihydroxy-16-p-nitrobenzyloxycarbonylamido-17-phenyl-5-cis,13-tra ns-18,19,20-trinor-prostadienoic acid derivative of general formula XII-wherein C-15 and C-16 may have either S or R configuration, W is as defined above, and Y stands for a lower alkyl group-in an optional sequence with the limitation that in those compounds of general formula I where W is as defined above and Y stands for a lower alkyl group, solely the p-nitrobenzyloxycarbonyl group is removed, and the resulting product of general formula I is optionally converted with an organic or inorganic acid into a salt. The new prostaglandin derivatives of the invention have valuable therapeutical properties, and can be applied in cattle raising for estrus and birth synchronization, furthermore in the veterinary praxis for the treatment of sterility, chronic endometritis and pyometry.