Patent ID: 8497393
Filing Date: 2013-07-30
Classification: A01N,A61K,A61P,C07C

Abstract:
1. A product comprising a compound of formula I or a pharmaceutically acceptable salt thereof, wherein said product is prepared by a process comprising (a) alkylating a compound of structure II with an alkylating agent to produce a compound of formula III, w=1, 2, or 3; Y 1 is trans-CH═CH—, cis-CH═CH—, —CH 2 (CH 2 ) m —, or —C≡C—; m is 1, 2, or 3; R 7 is (1) —C p H 2p —CH 3 , wherein p is an integer from 1 to 5, inclusive, (2) phenoxy optionally substituted by one, two or three chloro, fluoro, trifluoromethyl, (C 1 -C 3 ) alkyl, or (C 1 -C 3 )alkoxy, with the proviso that not more than two substituents are other than alkyl, with the proviso that R 7 is phenoxy or substituted phenoxy, only when R 3 and R 4 are hydrogen or methyl, being the same or different, (3) phenyl, benzyl, phenylethyl, or phenylpropyl optionally substituted on the aromatic ring by one, two or three chloro, fluoro, trifluoromethyl, (C 1 -C 3 )alkyl, or (C 1 -C 3 )alkoxy, with the proviso that not more than two substituents are other than alkyl, (4) cis-CH═CH—CH 2 —CH 3 , (5) —(CH 2 ) 2 —CH(OH)—CH 3 , or (6) —(CH 2 ) 3 —CH═C(CH 3 ) 2 ; —C(L (1) (C 4 -C 7 )cycloalkyl optionally substituted by 1 to 3 (C 1 -C 5 )alkyl; (2) 2-(2-furyl)ethyl, (3) 2-(3-thienyl)ethoxy, or (4) 3-thienyloxymethyl; M 1 is α-OH:β-R 5 or α-R 5 β-OH or α-OR 1 :β-R 5 or α-R 5 :β-OR 2 , wherein R 5 is hydrogen or methyl, R 2 is an alcohol protecting group, and L 1 is α-R 3 :β-R 4 , α-R 4 :β-R 3 , or a mixture of α-R 3 :β-R 4 and α-R 4 :β-R 3 , wherein R 3 and R 4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R 3 and R 4 is fluoro only when the other is hydrogen or fluoro, (b) hydrolyzing the product of formula III of step (a) with a base, (c) contacting the product of step (h) with a base B to form a salt of formula I (d) optionally reacting the salt formed in step (c) with an acid to form the compound of formula I.