Patent ID: 6143909
Filing Date: 2000-11-07
Classification: A61P,C07D,Y02P

Abstract:
A process for preparing a compound of the formula ##STR71## wherein G is C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.12 alkynyl, or Ar;Ar is an aromatic or heteroaromatic group or a substituted aromatic or heteroaromatic group;R.sup.3 is C.sub.1 -C.sub.6 alkyl;R.sup.4 and R.sup.5 are each hydrogen; or R.sup.4 and R.sup.5 taken together form a second bond between C-13 and C-14;R.sup.7 and R.sup.8 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl; orR.sup.7 and R.sup.8 taken together form a cyclopropyl or cyclobutyl ring;R.sup.9 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, --(CH.sub.2).sub.m --(C.sub.3 -C.sub.5)cycloalkyl or benzyl, wherein m is the integer one to three;R.sup.10 is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sup.11 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl or benzyl;R.sup.14 is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sup.50 is hydrogen or (.dbd.O);Y is CH, O, NH, SO, SO.sub.2 or (C.sub.1 -C.sub.3)alkylamino;R.sup.6 is C.sub.1 -C.sub.6 alkyl, substituted (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.8)cycloalkyl, substituted (C.sub.3 -C.sub.8)cycloalkyl, a heteroaromatic or substituted heteroaromatic group or a group of formula (IA), (IB) or (IC): ##STR72## R.sup.6a, R.sup.6b, and R.sup.6c independently are H, halo or OR.sup.18 ; R.sup.15, R.sup.16, and R.sup.17 independently are hydrogen, halo, (C.sub.1 -C.sub.6) alkyl, OR.sup.18, O-aryl, NH.sub.2, NR.sup.18 R.sup.19, NO.sub.2, OPO.sub.4 H.sub.2, (C.sub.1 -C.sub.6 alkoxy)phenyl, S-benzyl, CONH.sub.2, CO.sub.2 H, PO.sub.3 H.sub.2, SO.sub.2 R.sup.23, or Z';R.sup.18 and R.sup.19 independently are hydrogen or C.sub.1 -C.sub.6 alkyl;R.sup.23 is hydrogen or (C.sub.1 -C.sub.3)alkyl;Z is --(CH.sub.2).sub.11 -- or (C.sub.3 -C.sub.5)cycloalkyl;n is 0, 1, or 2; andZ' is an aromatic or substituted aromatic group; or a pharmaceutically acceptable salt thereof;comprising epoxidizing a compound of the formula ##STR73## wherein G, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.14 and R.sup.50 are as defined above and Y is Y' or S; with an oxidant and a chiral ketone to form a compound of formula (I); and optionally forming a pharmaceutically acceptable salt thereof.