17-g(a) AND 17-g(b)-SUBSTITUTED ESTRA-1,3,5(10)-TRIENE-3-CARBOXYLIC ACID

• Main Authors: LEVY, MARK ALAN, HOLT, DENNIS ALAN
• Format: Patent
• Language: English; French; German
• Published: 04.10.1995
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC USE OF COSMETICS OR SIMILAR TOILETPREPARATIONS; STEROIDS

PCT No. PCT/US93/03778 Sec. 371 Date Oct. 28, 1994 Sec. 102(e) Date Oct. 28, 1994 PCT Filed Apr. 22, 1993 PCT Pub. No. WO93/22333 PCT Pub. Date Nov. 11, 1993Invented 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 (I) wherein Z is alpha or beta 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 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: -OC6-C12aryl, -OC1-C4alkyl, halogen, carboxy and -S(O)nR7, where n is 0-2 and R7 is hydrogen or C1-4alkyl; b) C3-C8 nonaromatic, unsaturated or saturated, cycloalkyl, optionally substituted with one or more substituents selected from the group consisting of: -OC6-C12aryl, -(CH2)mOH, -OC1-C4alkyl, C6-C12aryl, C1-C4alkyl, trifluoromethyl, halogen, -(CH2)pCOOH, -S(O)nR7 and protected -OH, where m is 0-4, p is 0-3, n is 0-2 and R7 is hydrogen or C1-4alkyl; or c) C4-C12aryl, optionally containing one or more heteroatoms, provided that when C is 4 the aromatic ring contains at least one heteroatom, and optionally substituted with one or more substituents selected from the group consisting of: -OC6-C12aryl, -(CH2)mOH, C6-C12aryl, C1-C4alkyl, -OC1-C4alkyl, trifluoromethyl, halogen, -(CH2)pCOOH, -S(O)nR7 and protected -OH, where m is 0-4, p is 0-3, n is 0-2 and R7 is hydrogen or C1-4alkyl. Also invented are pharmaceutical compositions containing these compounds, and methods for using these compounds to inhibit steroid 5 alpha -reductase. Also invented are intermediates and processes used in preparing these compounds.