Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1976-10-08
1978-02-28
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
424180, C07H 1516
Patent
active
RE0295582
ABSTRACT:
Compounds of the formula: ##STR1## are disclosed, wherein R.sub.1 taken independently is hydrogen; R.sub.2 taken independently is the moiety ##STR2## wherein Ac is carboxacyl or an acyl group of formula: ##STR3## wherein Z is hydrogen, lower alkyl or a protective group removable by hydrogenolysis; R.sub.5 is lower alkyl; R.sub.1 and R.sub.2 when together are the divalent group; ##STR4## wherein Z and R.sub.5 are as defined above; R.sub.3 is hydrogen when R.sub.1 and R.sub.2 are taken together and is a monovalent thio group of formula: ##STR5## located in the 7(S)-position when R.sub.1 and R.sub.2 are taken independently, A represents hydrogen or hydroxyl, B represents hydrogen or hydroxyalkyl, n is the integer 0 when B is hydroxyalkyl and n is an integer of 0 to 1, inclusive, when B is hydrogen, X is oxygen [or sulfur], D is the acyl radical of a lower hydrocarbon carboxylic acid; R.sub.4 is lower alkyl and Y is carboxacyl or hydrogen.
Disclosed also are methods of making and using the novel compounds of the invention, which are useful intermediates in the chemical synthesis of useful antibacterial lincomycin analogs. Certain of the compounds of the invention are also active as antibacterial agents.
REFERENCES:
patent: 3271385 (1966-09-01), Martin
patent: 3689474 (1972-09-01), Kagan et al.
patent: 3702322 (1972-11-01), Bannister
Brown Johnnie R.
Eisele Joseph T.
Saliwanchik Roman
Stein Bruce
The Upjohn Company
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