NOVEL PROSTAGLANDINS

1476661 Prostaglandins AMERICAN CYANAMID CO 13 May 1974 21132/74 Headings C2C C2J and C2P [Also in Division C3] The invention comprises prostaglandins of the Formulae A and B wherein the side chains attached to the C 8 and C 12 positions of the cyclopentane, cyclopentene or cyclohexane ring are trans to each other and a hydroxy substituent at the C 11 position is trans to the side chain at the C 12 position; Y is Z is -(CH 2 ) m -, -(CH 2 ) m -C(R 4 ) 2 -CH 2 -, -(CH 2 ) m -CH(R 5 )-, -(CH 2 ) m -O-CH 2 -, cis-CH 2 -CH=CH-CH(R 6 )-(CH 2 ) p - or -(CH 2 ) m -S-CH 2 -, wherein m is 3 to 8, p is 1 to 5, R 4 is C 1-3 alkyl, R 5 is C 1-3 alkyl, F or phenyl, and R 6 is H or C 1-4 alkyl; -C 13 -C 14 - is ethylene or trans-vinylene; R 1 is C 1-3 alkyl; X is -CH 2 -, -CH 2 CH 2 - or Q is wherein R 7 is H or C 1-3 alkyl; R 3 is OH, C 1-12 alkoxy, 2-tetrahydropyranyloxy or trialkylsilyloxy; s is 0 to 5; t is 0 or 1; and R is C 5-9 cycloalkyl, C 5-9 cycloalkenyl, mono- or dialkyl substituted C 3-8 cyclo-alkyl or mono- or di-alkyl substituted C 5-8 cycloalkenyl; with the first proviso that when s and t are both 0 and -C 13 -C 14 - is trans-vinylene then R cannot be an optionally substituted cyclopropyl group; with the second proviso that when Z is -(CH 2 ) m - or and R is optionally substituted cycloalkyl then the sum of s and t is at least 1; and with the third proviso that when -C 13 -C 14 - is ethylene then Z cannot be and pharmaceutically acceptable salts thereof when R 3 is OH. The compounds are prepared by reacting cyclopentenones or cyclohexenones of the Formula H and R1 3 has all the values of R 3 except hydroxy, with alonates of the formula where R 9 is alkyl and R1 2 is triphenylmethyl or mono- or di-methoxy-substituted triphenylmethyl, to give compounds of the Formula J followed by hydrolysing the ester and ester groups with weak acids, to give compounds of the Formula K wherein R11 3 is OH or C 1-12 alkoxy, and optionally hydrolysing those compounds in which R 3 11 is C 1-12 alkoxy; optionally hydrogenating the C 13 -C 44 double bonds; optionally dehydrating the resulting compounds in which X is to give compounds of the Formula B above, optionally reducing the 9-oxo groups, and optionally introducing a C 1-3 alkyl group at C 16 in a known manner. The following intermediates and starting materials were also prepared: cyclopentenones or cyclohexenones of Formula H above including compounds in which X1 is 2 - (# - carboxy - 2 - cis - alkenyl) - 3,4 - epoxycycl