new mono (carboxyacylates) prostaglandins, their preparation and medicines containing plant

摘要

1389070 Cyclic boron prostaglandin intermediate UPJOHN CO 28 Nov 1972 [30 Dec 1971] 32010/74 Divided out of 1389069 Heading C2B The invention comprises optically active compounds of the formula or racemates thereof, wherein (a) X is trans- -CH=CH- or -CH 2 CH 2 - andY and Z are both -CH 2 CH 2 -, or (b) X is Y is cis-CH=CH- and Z is -CH 2 CH 2 - or cis-CH=CH-; M being where R 2 is H; C 1-17 alkyl; C 1-12 alkyl substituted by 1-3 substitutents selected from one or more of halogen, phenyl, phenoxy or C 3-7 cycloalkyl; phenyl optionally substituted 1-5 times by one or more of halogen, -CF 3 , nitro, phenyl or C 1-8 alkyl; or naphthyl; R 1 being H or C 1-8 alkyl; and R 3 being C 1-12 alkyl optionally substituted 1-3 times by one or more of halogen, amino, phenyl, trimethylsilyl or C 1-4 alkoxy; phenyl optionally substituted 1-5 times by one or more of halogen, nitro, hydroxy, C 1-4 alkoxy, carboxy, amino, phenyl or C 1-8 alkyl; naphthyl; or phenanthryl; and also, when R 1 is hydrogen, the pharmacologically acceptable salts of such compounds. The compounds are prepared by (1) reacting an optically active compound of the formula or a racemate thereof, wherein G is with a boronic acid R 3 B(OH) 2 , usually in a non- hydroxylic solvent such as pyridine, acetonitrile, acetone or N,N-dimethyl-formamide and under anhydrous conditions, to produce an optically active boronate of formula or a racemate thereof and (ii) reacting this boronate with a carboxyacylating agent such as R 2 COX (X is Cl, Br or F), or (R 2 CO) 2 O, preferably in the presence of a tertiary amine such as pyridine or (C 2 H 5 ) 3 N and using a substantial excess of the carboxyacylating agent and, optionally, a diluent.