Banyu Pharmaceutical Co. Ltd

Yoshiharu Tanaka

Susumu Nakagawa

Satoru Kuroyanagi

Akira Asai

Makoto Ishihara

Norikazu Otake

Ryosuke Ushijima

Koji Yamada

Fumio Nakano

Ryuji Mitomo

Moriaki Ishikawa

A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl and R.sup.21 is a group selected from the group consisting of: ##STR2## wherein R.sup.3 -R.sup.5, R.sup.31, R.sup.32, R.sup.41, R.sup.42 and R.sup.51 are as defined herein, and W is chlorine or bromine, is prepared by reacting a compound of the formula:

Process for producing enyne derivatives

(E)-N-(3-Chloro-2-propenyl)-N-methyl-1naphthylenemethanamine and (E)-3-chloro-N-(3-chloro-2-propenyl)-N-methylbenzo[b]thiophene-7-methanami ne which are useful as intermediates in the production of enyne compounds which exhibit squalene epoxidase inhibiting activity and anti-Eumycetes activity.

Intermediates for producing enyne derivatives

A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl; R.sup.21 is a group of the formula: ##STR2## wherein each of R.sup.3, R.sup.31, and R.sup.32 which may be the same or different, is hydrogen or lower alkyl, each of R.sup.4, R.sup.5, R.sup.41 and R.sup.51, which may be the same or different, is hydrogen, halogen, hydroxyl, lower alkyl or lower alkoxy, R.sup.42 is hydroxyl, halogen, R.sup.8 --O--, or R.sup.6 --X--Y-- wherein R.sup.6 is phenyl or thienyl which may have one or two substituents each of X and Y, which may be the same or different, is oxygen, sulfur, carbonyl, --CHR.sup.8 -- or --NR.sup.b, or X and Y together form a vinylene group or an ethynylene group, provided that when either one of X and Y is oxygen, sulfur or --NR.sup.b, the other is carbonyl or --CHR.sup.a, and R.sup.7 is lower alkyl or cycloalkyl which may be substituted by hydroxy or lower alkoxy, phenyl or tri-lower alkylsilyl; and W is chlorine or bromine.

A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula: ##STR1## wherein W is a halogen atom, with an acetylene derivative, in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.

A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane.epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula:

The present invention relates to a compound having the formula: ##STR1## wherein R is a hydrogen atom, a carboxyl-protecting group or a negative charge and Q is a hydrogen atom, a halogen atom, a hydroxyl group, an acetoxy group, a carbamoyloxy group, an azide group, a substituted or unsubstituted quarternary ammonio group or a substituted or unsubstituted heterocyclic thio group having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, or a non-toxic salt or physiologically hydrolyzable non-toxic ester thereof; a process for producing it; and an antibacterial agent comprising it as an active ingredient. Further, the present invention also relates to a compound having the formula: ##STR2## wherein R.sup.3 is a hydrogen atom or an amino-protecting group, and each of R.sup.4 and R.sup.5 which may be the same or different is a hydrogen atom or a carboxyl-protecting group, or a salt thereof; and a process for producing it.

1-carboxy-1-vinyloxyimino aminothiazole cephalosporin derivatives

A compound having the formula: ##STR1## wherein R is a straight chain or branched chain lower alkyl, cyclic lower alkyl, lower alkenyl (except for 1-carboxy-1-vinyl), lower alkynyl, aralkyl, phenyl or 2-pyrrolidon-3-yl group which may be substituted, and Q is ##STR2## (wherein R.sup.1 is a hydrogen atom or an acetyl group, R.sup.2 is a hydrogen atom, a carboxyl group or a carboxymethyl group, Y is a sulfur atom or an oxygen atom, Z is a sulfur atom, an oxygen atom or an imino group which may be substituted by a lower alkyl group); or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.

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Okazaki, Japan

Yoshiharu Tanaka