Kyowa Hakko Kogyo Co., Ltd.

Kyowa Hakko Kogyo Kabushiki Kaisha

Kentaro Tamaki

Takayoshi Yamauchi

Kaneaki Hattori

Shunichi Ikeda

Kyoichi Fujii

Shun-ichi Ikeda

Naoki Naito

Seiichi Yada

Kenji Nakao

Fumio Nishimura

Shiro Kudo

Nobuo Nakamura

Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxymethylene, or --CH.sub.2 --O--.

Cyclopentane derivatives

Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopetanecarbonyl)-R-1,1-diaminoet hane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxymethylene, or --CH.sub.2 --O--.

Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxy-methylene, or --CH.sub.2 --O--.

Compounds having anti-inflammatory and analgesic activity of the formula ##STR1## are produced from compounds having the formula ##STR2## by rearrangement in the presence of a base or an amide and (1) X S O X.sup.1 or X S O.sub.2 X.sup.1 where X and X.sup.1 are halogen or trifluoromethyl or (2) sulfur dioxide and halogen.

Process for producing an .alpha.-aromatic group substituted alkanoic

Disclosed is 3-(3-methyl-3-butenyl)-1, 2, 3, 4, 5, 6-hexahydro-6, 11-dimethyl-8-hydroxy-2, 6-methano-3-benzazocine, a new derivative of benzazocine, which has superior analgesic properties.

Analgesic

6,7-Benzomorphan derivatives, which are useful as unaddictive analgesics, are prepared from aromatic aminoketones through several steps of reactions. Most of the intermediates are new compounds. Process for preparing 2-benzyl-1,2,5,6-tetrahydropyridine derivatives which are known as intermediates for the preparation of 6,7-benzomorphan derivatives is also disclosed.

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Sakai, Japan

Kentaro Tamaki