Sankyo Company, Limited

Hideo Nakao

Hiroaki Yanagisawa

Shinichi Sugawara

Akiko Ando

Masami Fukushima

Koichi Fujimoto

Masakatsu Kaneko

Sadao Ishihara

Bunji Shimizu

Isamu Igarashi

Mitsuo Nagano

Norio Nakamura

Akio Saito

Eiji Nakayama

Hachio Miyazawa

Masao Arakawa

Masafumi Yoshimoto

Takuzo Nishimura

Compounds of formula (I): ##STR1## wherein: R.sup.1 represents a lower alkyl group selected from methyl groups and ethyl groups;

7-(2-amin

7-[2-(2-A

The compounds of the formula (I): ##STR1## wherein: R.sup.1 represents a hydrogen atom and

Cephalosporin derivative and antibiotic compositions

The acetoxymethyl group at the 3-position of 3-acetoxymethylcephalosporanic acids and salts thereof may be replaced by an alkoxymethyl group, by reacting the 3-acetoxymethylcephalosporanic acid or salt thereof with a C.sub.1 -C.sub.4 alkanol in the presence of halide ions.

Process for preparing 3-alkoxymethylcephalosporin derivatives

7.alpha.-Methoxycephalosporin derivatives of general formula (I): ##STR1## wherein: R.sup.1 represents a hydroxy group; a C.sub.1 -C.sub.4 alkoxy group; a C.sub.2 -C.sub.5 aliphatic acyloxy group; a benzoyloxy group which is unsubstituted or has one or more C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or halogen substituents; a benzenesulphonyloxy group which is unsubstituted or has one or more C.sub.1 -C.sub.4 alkyl substituents; or a C.sub.1 -C.sub.3 alkanesulphonyloxy group which is unsubstituted or has one or more C.sub.1 -C.sub.3 alkoxy, cyano, nitro, halogen or C.sub.2 -C.sub.4 alkoxycarbonyl substituents;

7.alpha.-Methoxycephalosporin derivatives and their pharmaceutical

A compound having the formula ##STR1## wherein Y represents a 2-carboxyethylthio group or a trifluoromethylthio group and a nontoxic pharmaceutically acceptable salt thereof are useful as antibacterial agents. They may be prepared by (a) reacting a compound having the formula ##STR2## wherein X.sub.1 represents a halogen atom with a compound having the formula

7-Methoxycephalosporin derivatives

Process for preparing .beta.-lactam antibiotic substances useful as intermediate for various cephalosporin or penicillin derivatives, which comprises oxidation of 7-benzylideneaminocephem or 6-benzylideneaminopenam compounds capable of being converted to their quinoid forms by oxidation followed by reaction with lower alkanols.

Process for preparing beta-lactam antibiotic substances

A process for preparing 7.alpha.-methoxycephalosporin compounds which comprises reacting a salt of a 7.beta.-benzylideneamino-7.alpha.-methoxy-3-cephem-4-carboxylic acid with a hydrazine compound to give a salt of a 7.beta.-amino-7.alpha.-methoxy-3-cephem-4-carboxylic acid and reacting the latter compound with a carboxylic acid or its reactive derivative. The products are useful as antibacterial agents.

Process for preparing 7-methoxycephalosporin compounds

Process for preparing 7-alkoxy cephalosporins useful as intermediates for various cephalosporin or penicillin derivatives which comprises reacting 7-benzylideneaminocephem or 6-benzylideneaminopenam compounds with a halide cation-producing compound in the presence of an alcohol and a base capable of forming a salt with a phenolic hydroxyl group or converting a phenolic hydroxyl group to phenolate ion.

Process for preparing alkoxylated derivatives of cephalosporin compounds

A process for introducing an alkoxy group into the 7.alpha.-position of a 7-amino-3-cephem-4-carboxylic acid derivative which comprises oxidizing a salt of 7-benzylideneamino-3-cephem-4-carboxylic acid derivative and reacting the product with an alkanol. The 7.alpha.-alkoxy-3-cephem-4-carboxylic acid derivatives obtained by the present invention are useful as intermediates for the synthesis of antibacterial agents.

Process for preparing 7 .alpha.-alkoxycephalosporin derivatives

Process for preparing cephalosporin derivatives

A compound of the formula ##STR1## wherein A represents acetoxy group, carbamoyloxy group or (1-metyl-1H-tetrazol-5-yl)thio group and Y represents propargylthio group, azidomethylthio group, 2-hydroxyethylthio group, 3-isoxazolyloxy group, 3-isoxazolylthio group, methylsulfonyl group, ethylsulfonyl group, 2-cyanoethyl-sulfonyl group or sydnon-3-yl group and nontoxic pharmaceutically acceptable salts thereof are prepared by a process which comprises reacting a compound of the formula ##STR2## wherein R represents a protective group for a carboxyl group and A has the same meaning as defined above with a carboxylic acid of the formula

Cephalosporin derivatives

Nitrosourea derivatives represented by the formula ##STR1## wherein A represents a group of the formula B--Y-- in which B is an unsaturated 5- or 6-membered heterocyclic group which has the as hetero atom at least one nitrogen atom, an unsaturated 9-membered heterocyclic group which has as the hetero atom at least one nitrogen atom and a bicyclic fused ring or an unsaturated 10-membered heterocyclic group which has as the hetero atom at least one nitrogen atom and a bicyclic fused ring, the heterocyclic groups optionally having alkyl, alkoxy, hydroxyl, amino, hydroxyalkyl or halogen as ring substituent and Y represents a group of the formula --(CH.sub.2).sub.m -- in which m is an integer of 1 or 2, the group optionally having alkyl as a substituent; A group of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be the same or different and each represents a hydrogen atom or an alkyl group; or a group of the formula ##STR3## in which R's may be the same or different and each represents a halogen atom or an alkyl group, n is an integer of 0 to 3 inclusive and Z is an ethylene group which may be substituted with alkyl; and X represents a halogen atom and acid addition salts thereof. The Compounds of the present invention are prepared from the corresponding 2-halogeno-ethylurea derivatives by means of conventional nitrosation procedures and useful as an antileukemic drug for various types of leukemia.

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Tokyo, Japan

Hideo Nakao