Sumitomo Pharmaceuticals Company Limited

Sumitomo Chemical Company, Limited

Dainippon Sumitomo Pharma Co., Ltd.

Fujifilm Corporation

Nitto Electric Industrial Co., Ltd.

Makoto Sunagawa

Haruki Matsumura

Akira Sasaki

Takaaki Inoue

Hisao Yamamoto

Junki Katsube

Masatomo Fukasawa

Masuhiro Kato

Hiroshi Yamaga

Hiromi Sato

Koshiro Goda

Atsuyuki Kojima

Yoshito Kameno

Masao Enomoto

Yoshinori Takashima

Hiroshi Nouda

Hisatoshi Shinagawa

Yoshihiro Sumita

Tsuneo Yano

Shinzi Takata

Yutaka Kitamura

Masanori Itoh

Erwin Goetschi

Shiro Terashima

Tamejiro Hiyama

Yutaka Hori

Kunikazu Sakai

Katsumi Tamoto

Naoki Matsuoka

Toshiyuki Hirohashi

Seiji Hori

Tetsuo Noguchi

Nobuo Kato

Yoshikazu Kimura

Katsumi Kubota

Yukio Ozaki

Yoshio Ito

Takeo Kawabata

Takashi Bando

Masamoto Fukasawa

Yutaka Takeuchi

Yusuke Higuchi

Yutaka Isobe

Chihiro Kondo

Yoshihito Nozaki

The object is to provide a stable SM-108 derivative, which is effective as a carcinostatic agent, particularly an SM-108 derivative having good storage stability. An SM-108 compound having good storage stability can be produced by producing an organic sulfonic acid salt compound of SM-108. Further, a crystalline SM-108 compound containing a trace amount of an organic carboxylic acid can be produced by using an aqueous solution of the organic sulfonic acid salt of SM-108, and by adding an alkali metal salt of an organic carboxylic acid to the aqueous solution to neutralize the aqueous solution and then causing the crystal precipitation in the solution.

Sulfonic acid salt compound of 4-carbamoyl-5-hydroxy-imidazole derivative

Carbapenem compounds represented by the general formula [1] or pharmaceutically acceptable salts thereof: wherein Ris C-Calkyl or hydroxylated C-Calkyl, R is hydrogen atom or a group which is hydrolyzed in vivo into a carboxy group, and G is a group represented by one of the formulae [G1], [G2], and [G3]. 

Carbapenem compounds

A compound or its pharmaceutically acceptable salt represented by the following formula: The invention is a carbapenem compound which has a potent antibacterial activity over a broad range of Gram negative and Gram positive bacteria, especially penicillin-resistant(PRSP) which has been isolated at an elevated frequency in recent years and thus causes a serious clinical problem, andwhich has acquired resistance against the existing &#x3b2;-lactam antibiotics over a wide scope due to penicillin-binding protein (PBP) mutations such as &#x3b2;-lactamase non-producing ampicillin-resistant (BLNAR), and has excellent oral absorbability.

1. A &#x3b2;-lactam compound of the formula [1]; wherein Ris a lower alkyl, a lower alkyl substituted by a hydroxy; Ris a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Yis a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Yis hydrogen, an alkyl, cyano, &#x2014;C(R)&#x2550;NR(wherein Rand Rare hydrogen, an amino, an alkyl, etc., or Rand Rmay combine each other together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has an excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.

&#x3b2;-lactam compounds and process for producing the same

Carbapenem compounds having a substituted phenyl or a substituted thienyl directly attached to the-position of carbapenem nucleus as represented by the formula: wherein Ring E is benzene ring or thiophene ring; Ris optionally OH-substituted Calkyl; Rand Rrepresent each H, optionally substituted lower alkyl, etc.; R is H, or a group which is hydrolyzed in the living body to regenerate a carboxyl group, etc.; X is O or S; and Y represents H, lower alkyl, etc., or pharmaceutically acceptable salts thereof and medicaments containing said compound as the active ingredient. These compounds exhibit an excellent antibacterial activity over a broad range of Gram-positive and Gram-negative bacteria, in particular, penicillin-resistant(PRSP) which has been isolated at an elevated frequency in recent years and thus causes a serious clinical problem, andwhich has acquired resistance against the existing &#x3b2;-lactam antibiotics over a wide scope due to penicillin-binding protein (PBP) mutations such as &#x3b2;-lactamase non-producing ampicillin-resistant (BLNAR)

&bgr;-lactam compounds and process for producing the same

&bgr;-lactam compounds and process for preparing the same

Carbapenem compounds and process for producing the same

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

A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, the same or different, each a hydrogen atom or a lower alkyl group, R.sub.3.sup.o is a lower alkyl group having a beta-configuration, R.sub.4 is a carboxyl-protecting group, X is a hydrogen atom or a protected hydroxyl group and COZ is a protected thiolcarboxyl group, which is useful as a valuable intermediate in the stereospecific production of 1-alkylcarbapenem compounds.

Beta-lactams and their production

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

A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, the same or different, each a hydrogen atom or a lower alkyl group, R.sub.3.sup.0 is a hydroen atom or a lower alkyl group having a beta-configuration, R.sub.4 is a carboxyl-protecting group, X is a hydrogen atom or a protected hydroxyl group and COZ is a protected thiolcarboxyl group, which is useful as a valuable intermediate in the stereospecific production of 1-alkylcarbapenem compounds.

A compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group, an ar(lower)alkyl group or an aryl group, or R.sub.1 and R.sub.2 may be combined together to form a lower alkylene group and/or R.sub.3 and R.sub.4 are combined together to form a lower alkylene group, or R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be combined together to form an o-phenylene group, X is a halogen atom and Y is an oxygen atom or a nitrogen atom substituted with lower alkyl or aryl, which is useful as an intermediate in the synthesis of 1.beta.-methylcarbapenem compounds valuable as antibiotics.

Heterocyclic compounds and their production

A compound of the formula: ##STR1## , which is useful as an antimicrobial agent.

.beta.-lactam compounds and their production

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

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Itami, Japan

Makoto Sunagawa