17.alpha. and 17.beta.-substituted estra-1,3,5(10)-triene-3-carbboxlic acid

US5618806A · kind A · utility

Assignee

• SmithKline Beecham Limited · US

Inventors

• Dennis A. Holt · Downingtown, US
• Mark A. Levy · Wayne, US

Key dates

• Filing date: Oct 28, 1994
• Grant date: Apr 8, 1997
• Expiry date: Oct 28, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J43/003
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Invented are 17.alpha. and 17.beta.-substituted acyl-3-carboxy aromatic A ring analogues of steroidal synthetic compounds. Representative of such compounds include the following ##STR1## wherein Z is .alpha. or .beta. ##STR2## in which A is absent or present as a linear or branched, saturated or unsaturated hydrocarbon chain containing from 1-6 carbon atoms and R is PA1 a) a linear or branched, saturated or unsaturated hydrocarbon chain containing 1-12 carbon atoms substituted with one or more substituents selected from the group consisting of: --OC.sub.6 -C.sub.12 aryl, --OC.sub.1 -C.sub.4 alkyl, halogen, carboxy and --S(O).sub.n .sup.R.sup.7, where n is 0-2 and R.sup.7 is hydrogen or C.sub.1-4 alkyl; PA1 b) C.sub.3 -C.sub.8 nonaromatic, unsaturated or saturated, cycloalkyl, optionally substituted with one or more substituents selected from the group consisting of: PA2 --OC.sub.6 -C.sub.12 aryl, --(CH.sub.2).sub.m OH, --OC.sub.1 -C.sub.4 alkyl, C.sub.6 -C.sub.12 aryl, C.sub.1 -C.sub.4 alkyl, trifluoromethyl, halogen, --(CH.sub.2).sub.p COOH, --S(O).sub.n R.sup.7 and protected --OH, where m is 0-4, p is 0-3, n is 0-2 and R.sup.7 is hydrogen or C.sub.1-4 alkyl; or PA1 c) C.sub.4 -C.…