Lederle (japan), Ltd.

Chisato Sato

Satoshi Tamai

Takeshi Isoda

Toshio Kumagai

Takao Abe

Ado Mihira

Kazuhiko Hayashi

A first embodiment of the invention relates to novel carbapenem compounds, (1R, 5S, 6S)-2-�1-(1,3-thiazolin-2-yl)azetidin-3-yl!thio-6-�(R)-1-hydroxy-ethyl!-1- methylcarbapen-2-em-3-carboxyic acid derivatives. These carbapenem compounds are represented by the following formula having a beta-coordinated methyl group introduced at the 1-position and a �1-(1,3-thia-zolin-2-yl)azetidin-3-yl!thio group introduced at the 2-position. ##STR1## In the formula, R is hydrogen; lower alkyl group which is unsubstituted or substituted by hydroxy, lower alkoxy or lower alkoxy-lower alkoxy group; group --COOR.sup.1 (R.sup.1 is hydrogen or lower alkyl group); or group --CONR.sup.2 R.sup.3 (R.sup.2 and R.sup.3 are, independently each other, hydrogen or lower alkyl), and Y is carboxy, --COO.sup..crclbar. or protected carboxy. These compounds are useful antibiotics for prevention and treatment of bacterial infections. The second embodiment of the invention relates to 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine represented by the following formula and its acid addition salts ##STR2## and to the production process therefor. The above compounds are useful as intermediates for preparing carbapenem compounds, which have strong antibacterial activity, with convenience and high yield.

Sulfur-containing compounds method for their use and prodction

Novel carbapenem compounds, (1R,5S,6S)-2-�1-(1,3-thiazolin-2-yl)azetidin-3-yl!thio-6-�(R)-1-hydroxyeth yl!-1-methyl-carbapen-2-em-3-carboxyic acid derivatives. These carbapenem compounds are represented by the following formula having a beta-coordinated methyl group introduced at the 1-position and a �1-(1,3-thiazolin-2-yl)azetidin-3-yl!thio group introduced at the 2-position. ##STR1## In the formula, R is hydrogen; lower alkyl group which is unsubstituted or substituted by hydroxy, lower alkoxy or lower alkoxy-lower alkoxy group; group --COOR.sup.1 (R.sup.1 is hydrogen or lower alkyl group); or group --CONR.sup.2 R.sup.3 (R.sup.2 and R.sup.3 are, independently each other, hydrogen or lower alkyl), and

2-�1-(1,3-thiazolin-2-yl)azetidin-3-yl!thio-carbapenem derivatives

This invention relates to 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine represented by the following formula and its acid addition salts ##STR1## and to the production process therefor. The above compounds are useful as intermediates for preparing carbapenem compounds, which have strong antibacterial activity, with convenience and high yield.

Thiol compounds

Novel carbapenem compounds, (1R,5S,6S)-2-[1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyeth yl]-1-methyl-carbapen-2-em-3 -carboxyic acid derivatives. These carbapenem compounds are represented by the following formula having a beta-coordinated methyl group introduced at the 1-position and a [1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio group introduced at the 2-position. ##STR1## In the formula, R is hydrogen; lower alkyl group which is unsubstituted or substituted by hydroxy, lower alkoxy or lower alkoxy-lower alkoxy group; group --COOR.sup.1 (R.sup.1 is hydrogen or lower alkyl group); or group --CONR.sup.2 R.sup.3 (R.sup.2 and R.sup.3 are, independently each other, hydrogen or lower alkyl), and Y is carboxy, --COO.sup..crclbar. or protected carboxy. These compounds are useful antibiotics for prevention and treatment of bacterial infections.

Growing community of inventors

Kamifukuoka, Japan

Chisato Sato