Sumitomo Pharmaceuticals Company Limited

Sumitomo Chemical Company, Limited

Haruki Matsumura

Makoto Sunagawa

Takaaki Inoue

Masuhiro Kato

Akira Sasaki

Masatomo Fukasawa

Tsuneo Yano

Shinzi Takata

Yutaka Kitamura

Toshiyuki Hirohashi

Masao Enomoto

Tetsuo Noguchi

Yukio Ozaki

Yutaka Takeuchi

Yutaka Isobe

Masamoto Fukasawa

Yoshihito Nozaki

Takashi Bando

Novel and effective process for preparing a carbapenem compound of the formula (III): ##STR1## wherein R.sub.1 and R.sub.2 are each H or lower alkyl, R.sub.3 is lower alkyl, R.sub.4 is a protecting group, L is substituted or unsubstituted arylsulfonyloxy, lower alkanesulfonyloxy, halogeno-lower alkanesulfonyloxy, di-lower alkylphosphoryloxy, etc., and X is H or protected hydroxy, which comprises reacting a .beta.-lactam compound (I) with an acetic acid ester derivative (II), in the presence of base, followed by treating the product with an active esterifying agent for a hydroxy group, said compound (III) being useful as intermediate in preparing 1.beta.-alkylcarbapenem compounds having antibacterial activity.

Process for preparing carbapenem compounds

Pyrrolidine derivatives of the formula (1): ##STR1## wherein R is a protective group of the amino group, intermediates for constructing the 2-positioned side chain of antibacterial penem and carbapenem compounds, are prepared by allowing ##STR2## to react with active esterifying agents in the presence of a base, further allowing the product to react with hydrogen sulfide in the presence of a base and then treating the product with a base.

Pyrrolidine derivatives and process for preparing the same

Crystalline palladium tetrakis (triphenylphosphine) which exhibits a specific powder X-ray pattern and is excellent in storage stability is obtained by allowing palladium chloride to react with triphenylphosphine in aprotic polar solvents, treating the reaction mixture with an aqueous hydrazine solution, collecting the resulting crystals by filtration, washing with alcohols and further washing with hydrocarbon solvents.

Crystalline palladium tetrakis(triphenylphosphine) and a process for

An amino acid compound of the formula: ##STR1## wherein R is a lower alkyl group, R.sub.1 is a hydrogen atom or a protecting group for carboxyl, R.sub.2 is a hydrogen atom, a protecting group for amino, an optionally substituted allyl group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group or an aryl group), a beta-hydroxyethyl group in which the hydroxyl group is optionally protected, a formylmethyl group in which the formyl group is optionally protected, a carboxymethyl group in which the carboxyl group is protected or a 2-furylmethyl group and X is an optionally protected carboxyl group, a hydroxymethyl group in which the hydroxyl group is optionally protected or a substituted mercaptomethyl group of the formula:

3(1-hydoxyethyl)azetidinone compounds and their production

Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.

.beta.-lactam compounds

A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.

Beta-lactams

A beta-lactam compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, which is useful as an anti-microbial agent or an intermediate in the synthesis of anti-microbial agents.

Beta-lactam compounds

Beta-lactams and their production via stereospecific hydrogenation

A compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl group, R.sub.2 is a hydrogen atom or a conventional protecting group for a carboxyl group, R.sub.0 is a hydrogen atom or a conventional protecting group for a hydroxyl group, X is a protected or unprotected amino group, a carboxyl group, a lower alkoxycarbonyl group, an ar(lower)alkyloxycarbonyl group, a cyano group, a hydroxyl group, a lower alkyloxy group, a lower alkylthio group, a lower alkylsulfonyl group or a group of either one of the following formulas: ##STR2## wherein R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom or a lower alkyl group, or they are taken together to represent an alkylene chain to form, in combination with the adjacent nitrogen atom, a 3- to 7-membered cyclic amino group,

Carbapenem compounds and production thereof

(4R,5S,6S 8R,2'S,4'S)-3-[4-(2-Dimethylaminocarbonyl)pyrrolidinylthio]-4-methyl-6-(1- hydroxyethyl)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid of the formula: ##STR1## in a crystalline form, which is useful as an antibiotic agent.

Carbapenem compound in crystalline form, and its production and use

Novel .beta.-lactam compounds classified into penem compounds, a process for preparing the same and use of such .beta.-lactam compounds are disclosed. These .beta.-lactam compounds exhibit excellent antimicrobial activities useful as pharmaceuticals or they are important intermediates for the synthesis of compounds having antimicrobial activities.

Antibacterial .beta.-lactam compounds

A process for preparing a .beta.-lactam derivative having a hydrogen atom on the nitrogen atom of the .beta.-lactam ring, which comprises reacting a .beta.-lactam derivative having a mono- or diarylmethyl group on the nitrogen atom of the .beta.-lactam ring with an acid or ceric ammonium nitrate to cleave the bond between the nitrogen atom and the mono- or diarylmethyl group; and novel .beta.-lactam derivatives useful as intermediates for the synthesis of pharmaceutical agents.

Growing community of inventors

Nara, Japan

Haruki Matsumura