Patent ID: 6437151
Filing Date: 2002-08-20
Classification: C07D,C07H,C07K,C12N,C12P

Abstract:
A process for preparing a compound of formula 1:and to pharmaceutically acceptable salts thereof, wherein:R1 is an alpha-branched C3-C8 alkyl, alkenyl, alkynyl, alkoxyalkyl or alkylthioalkyl group any of which may optionally be substituted by one or more hydroxyl groups; a C5-C8 cycloalkylalkyl group wherein the alkyl group is an alpha-branched C2-C5 alkyl group; a C3-C8 cycloalkyl or C5-C8 cycloalkenyl group, either of which may optionally be substituted by methyl or one or more hydroxyl or one or more C1-C4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be saturated, or fully or partially unsaturated and which may optionally be substituted by one or more C1-C4 alkyl groups or halo atoms; or R1 is phenyl which may be optionally substituted with at least one substituent selected from C1-C4 alkyl, C1-C4 alkoxy and C1-C4 alkylthio groups, halogen atoms, hydroxyl groups, trifluoromethyl, and cyano; or R1 may be with formula (a) as shown below: wherein X is O, S or â€”CH2â€”, a, b, c, and d are each independently 0-2 and a+b+c+d&lE;5;R2 is H or OH; R3-R5 are each independently H, CH3, or CH2CH3; R6 is H or OH; and R7 is H, CH3, or CH3CH2; R8 is H or desosamine; R9 is H, CH3, or CH2CH3; R10 is OH, mycarose (R13 is H), or cladinose (R13 is CH3), R11 is H; or R10&boxH;R11&boxH;O; and R12 is H, CH3, or CH2CH3; or any of the above defined compounds modified by replacing one or more â€”CHOH or â€”CHOR groups by a keto group, which comprises fermenting an organism capable of producing erythromycin in the presence of a carboxylic acid of the formula R1CO2H wherein R1 is as defined hereinabove, or a salt, ester or amide thereof or oxidative precursor thereof, and isolating the compound of formula 1.