2-unsaturated alkylthio-pen-2-em-3-carboxylic acids

Details 2-unsaturated alkylthio-pen-2-em-3-carboxylic acids 2-unsaturated alkylthio-pen-2-em-3-carboxylic acids

1983-01-25

1987-06-23

Rizzo, Nicholas S.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540310, 540350, 514194, 514195, C07D49900, A61K 31425

Patent

active

046753176

ABSTRACT:
Disclosed are 6- and 6,6-disubstituted-2-substituted thio-pen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein: R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently selected from: hydrogen; substituted and unsubstituted: alkyl, cycloalkyl, halo, alkoxyl, alkenyl, aralkyl, aryl, heterocyclyl, heteroaryl, and heterocyclylalkyl; W is an electron withdrawing group, and, for example, is selected from: --COR.sup.5, --CN, SO.sub.2 C.sub.6 H.sub.5 ; R.sup.5 is hydrogen; substituted and unsubstituted: alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, or heterocyclylalkyl; or R.sup.5 may be --OR.sup.6, --NR.sup.7 R.sup.8, and --SR.sup.9 ; wherein R.sup.6 is H; substituted and unsubstituted: alkyl, alkenyl, or a group which defines --CO.sub.2 R.sup.6 as a pharmaceutically acceptable ester wherein R.sup.6 is, for example, phthalidyl, or 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl; R.sup.7 and R.sup.8 are independently selected from: hydrogen; substituted and unsubstituted: alkyl, aralkyl, aryl, heterocyclyl, and heterocyclylalkyl; R.sup.9 is substituted and unsubstituted: alkyl, aralkyl, aryl, heterocyclyl, and heterocyclyclalkyl; R.sup.3 may also be W; n is 0 or 1; when the unsaturated moiety attached to the exocyclic sulfur atom is acetylenic, then R.sup.3 and R.sup.4 are nonexistent and W is as previously defined. Such compounds I are new and they and their pharmaceutically acceptable salt and ester derivatives are useful as antibiotics.

REFERENCES:
patent: 4168314 (1979-09-01), Christensen et al.
patent: 4395418 (1983-07-01), Ohki et al.
patent: 4517124 (1985-05-01), Brown
J. Org. Chem. 42, 2960 (1977).
Merck Index, 9th ed., p. ONR-60.
J. Chem. Soc. Chem. Comm. No. 13, pp. 713-714 (1982).
Jeffrey & McCombie, J. Org. Chem. 43, 587 (1982).
A. Yoshida, T. Hayoshi, N. Takeda, S. Ohda & E. Olki Chem. Pharm. Bull. 29, 2899 (1981).

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