Process of producing 8A- and 9A-azalide antibiotics
AssigneeMerck & Co., Inc.
InventorsSherman T. Waddell, Timothy A. Blizzard
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Abstract
A process of producing 8a- and 9a- azalide compounds is disclosed, comprised of reacting an 8a- aza or 9a- aza azalide eastern fragment or a derivative thereof with a compound of the formula: X--A'--Y wherein X and Y are appropriate reactive groups and A' is a fragment or compound which forms the western portion of the azalide, and cyclizing this intermediate to form the target 8a- or 9a-azalide compound. Compounds of formula I, II and III as well as other azalides can be synthesized according to this process.
Claims9
A process of producing an 8a- or 9a-azalide compound comprising reacting an 8a- or 9a-azalide eastern fragment or a derivative thereof with a compound of the formula:
- X--A'--Y wherein X and Y are appropriate reactive groups and A' is a compound which forms the western portion of the azalide, and
- cyclizing to form the 8a- or 9a-azalide compound.
A process of producing an 8a- or 9a-azalide comprised of:
- (a) reacting an 8a-aza or 9a-aza fragment of the formula:
- ##STR538## wherein P' is methyl or benzyl, or the carboxylate derivative of said 8a-or 9a-azalide fragment, with a compound of the formula X--A'--Y wherein X and Y are groups reactive with the ester or carboxylate and amine functional groups respectively of the 8a- and 9a-azalide fragments,, and A' is a chain containing three to five carbon atoms, uninterrupted or interrupted by one or two heteroatoms selected from O, S and NR.sup.1, wherein R.sup.1 represents H, C.sub.1 to C.sub.7 alkyl, aralkyl or arylsulfonyl, said alkyl, aralkyl and arylsulfonyl being unsubstituted or substituted with fluoro, alkyl or R.sup.10 O,
- or said chain further being optionally interrupted by a heterocycle, cycloalkyl, aryl or heteroaryl group,
- said --A'-- being unsubstituted or substituted with lower alkyl, hydroxy, halo, alkoxy, amino, aryl, heteroaryl, cycloalkyl, aryloxy, heteroaryloxy, heterocycloalkyl, heterocycloalkoxy, haloalkyl, arylsulfonyl or arylsulfonylamino to form the 8a- or 9a-azalide compound.
Dependencies are inferred from the claim text.