Shionogi Company Limited

Daikan Kogyo Co., Ltd.

Tadahiko Tsushima

Mitsuaki Ohtani

Fumihiko Watanabe

Nobuhiro Haga

Susumu Kamata

Kenji Kawada

Tatsuo Tsuri

Masayuki Narisada

Kaoru Seno

Sanji Hagishita

Tetsuo Okada

Hiroshi Tanida

Susumu Misaki

Masahiro Suefuji

Shoichi Ishihara

The present invention relates to process for the isolation of (-)-(S)-3-methylamino-4-methylenepyrrolidine derivatives of the formula: ##STR1## wherein R is hydrogen or amino-protecting group, from the racemic mixture of them comprising the salt formation of the racemate with L-(+)-tartaric acid in a molar ratio of 2:1 and subsequent treatment with a base, and optionally followed by deprotection of the amino-protecting group. By this process, complicated procedure in resolutional crystallization is not necessary and (-)-(S)-3-methylamino-4-methylenepyrrolidine derivatives can be obtained as optically pure form in above 90% yield quantitatively by single procedure.

Optically active cyclic amine and the process of optical resolution

A compound of the formula: ##STR1## wherein R and R' each is hydrogen or a protecting group, or acid addition salts thereof, useful as a selective insecticide.

S-difluoromethylhomocysteines, preparation process, and selective

There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkyamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 -O--CH.sub.2 -- or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically accepatble salts. The compounds are useful as antithrombotic, anti-vasconstricting and anti-bronchoconstricting drugs.

6-oxa and thiabicyclo [3.1.0.] compounds

Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or hetelocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms and may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.

7-oxabicyclo[2.2.1] heptane sulfonamide derivatives

Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or heterocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms an may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.

Bicyclic sulfonamide derivatives

A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.

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Osaka, Japan

Tadahiko Tsushima