Teijin Limited

Kazuhiko Itoh

Takeshi Hara

Sachio Ishimoto

Yoshinobu Hashimoto

Naomi Okamoto

Ryoichi Hasegawa

Yasutaka Kayama

Yoichi Sakata

Shuichiro Hino

Toshiro Mori

Hitoshi Fujimori

Toshinobu Murakami

Tamiko Sunami

Atsushi Noro

Human tissue plasminogen activator-human plasminogen activator inhibitor

Novel 4H-pyrrolo[1,2-a][1,4]benzodiazepine derivatives of the formula ##STR1## wherein at least one of R.sub.1, R.sub.2 and R.sub.3 represent lower alkyl and the remainder hydrogen, R.sub.4 represents hydrogen or lower alkyl, ring A optionally contains at least one substituent selected from halogen, nitro and trifluoromethyl, and ring B optionally contains at least one substituent selected from halogen, nitro, trifluoromethyl, lower alkyl and lower alkoxy; and novel intermediates thereof expressed by the formula ##STR2## wherein Z represents protected amino. Compounds of formula (I) are prepared by subjecting compounds of formula (II) to protective group-elimination and cyclization. The compounds of formula (I) and acid addition salts thereof have useful anti-anxietic, sedative, anti-convulsant, muscle relaxant and hypnotic, and their toxicity is low.

Benzodiazepine derivatives and pharmaceutical compositions containing

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Iwakuni, Japan

Kazuhiko Itoh