2-Substituted penam derivatives

Abstract

A compound of the general formula: ##STR1## wherein R.sup.1 is amino or a conventional, pharmaceutically acceptable acylamino, R.sup.2 is carboxy or a conventionally protected carboxy, X is --S-- or ##STR2## R.sup.3 is lower alkyl and Y" is a residue of a strong nucleophile selected from the group consisting of azido, thiocyanato, lower alkyanoylthio and piperidinothiocarbonylthio.

Description

Claims

1. A compound of the general formula: ##STR247## wherein R.sup.1 is a conventional, pharmaceutically acceptable penicillin acylamino, R.sup.2 is carboxy or a conventionally protected carboxy, X is --S-- or ##STR248## R.sup.3 is lower alkyl and Y" is a residue of a strong nucleophile selected from the group consisting of thiocyanato, lower alkyanoylthio and piperidinothiocarbonylthio.

2. The compound according to claim 1, in which R.sup.1 is phenyl (lower) alkanoylamino, phenoxy(lower)alkanoylamino, N-lower alkyoxycarbonylphenylglycylamino or 3-halophenyl-5-(lower)alkylisoxazol-4-ylcarboxamido, R.sup.2 is carboxy, lower alkoxycarbonyl, trihalo(lower)alkoxycarbonyl and carboxy salt , R.sup.3 is lower alkyl, X is --S-- or ##STR249## or Y" is thiocyanato, lower alkanoylthio or piperidinothiocarbonylthio.

3. The compound according to claim 2, in which R.sup.1 is phenylacetamido, phenoxyacetamido, N-(1-cyclopropylethoxy)carbonylphenylglycylamino or 3-(2-chlorophenyl)-5-methylisoxazol-4-ylcarboxamido, R.sup.2 is carboxy, methoxycarbonyl, 2,2,2-trichloroethoxycarbonyl or a carboxy salt with N,N'-dibenzylethylenediamine, R.sup.3 is a methyl, X is --S-- or ##STR250## and Y" is thiocyanato, acetylthio or piperidinothicarbonylthio.

4. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-thiocanatomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate.

5. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-thiocyanatomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate.

6. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-thiocyanatomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-.beta.-oxide.

7. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-thiocyanatomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate.

8. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-thiocyanatomethyl-2-methyl-6-[3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido]penam-3-carboxylate.

9. The compound according to claim 3, which is N,N'-dibenzylethylenediamine 2-acetylthiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate.

10. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-acetylthiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate.

11. The compound according to claim 3, which is N,N'-dibenzylethylenediamine 2-piperidinothiocarbonylthiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate.

12. The compound according to claim 3, which is 2,2,2-trichloroethyl 2-piperidinothiocarbonylthiomethyl-2-methyl-6-(2-phenylacetamido) penam-3-carboxylate.