Patent ID: 6765117
Filing Date: 2004-07-20
Classification: C07C

Abstract:
A stereoselectively produced isomeric compound according to the following formula: that is produced by a process for making 9-deoxy-PGF1-type compounds, the process comprising cyclizing a starting compound of the formula: into a compound of the following formula: by intramolecular cyclization of the enyne, wherein Z is O, S, CH2, or NR8 in which R8 is H, alkyl or aryl; X is H, CN, OR9, or COOR9 in which R9 is H, alkyl, a pharmacologically acceptable cation, THP or TBDMS; wherein n is 0, 1, 2, or 3; wherein Y1 is trans-CH&boxH;CHâ€”, cis-CH&boxH;CHâ€”, CH2(CH2)m-, or â€”Câ‰¡Câ€”; m is 1,2, or 3; wherein R1 is an alcohol protecting group; wherein R7 is (1) â€”C2H2pâ€”CH3, wherein p is an integer from one to 5, inclusive, (2) phenoxy optionally substituted by one, two or three chloro, fluoro, trifluoromethyl, (C1-C3)alkyl, or (C1-C3)alkoxy, with the proviso that not more than two substituents are other than alkyl, with the proviso that R7 is phenoxy or substituted phenoxy, only when R3 and R4 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, (C1-C3)alkyl, or (C1-C3)alkoxy, with the proviso that not more than two substituents are other than alkyl, (4) cis-CH&boxH;CHâ€”CH2â€”CH3, (5) â€”(CH2)2â€”CH(OH)â€”CH3, or (6) â€”(CH2)3â€”CH&boxH;C(CH3)2; wherein â€”C(L1)â€”R7 taken together is (1) (C4-C7)cycloalkyl optionally substituted by one to 3 (C1-C5) alkyl; (2) 2-(2-furyl)ethyl, (3) 2-(3-thienyl)ethoxy, or (4) 3-thienyloxymethyl; wherein M1 is &agr;-OH:&bgr;-R5 or &agr;-R5:&bgr;-OH or &agr;-OR1:&bgr;-R5 or &agr;-R5:&bgr;-OR1, wherein R5 is hydrogen or methyl and R1 is an alcohol protecting group; and wherein L1 is &agr;-R3:&bgr;-R4, &agr;-R4:&bgr;-R3, or a mixture of &agr;-R3:&bgr;-R4 and &agr;-R4:&bgr;-R3, wherein R3 and R4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R3 and R4 is fluoro only when the other is hydrogen or fluoro.