1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones and intermediates

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514339, 546256, 546273, C07D40104, A61K 3144

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active

054648467

ABSTRACT:
This application is a continuation-in-part of pending U.S. patent application Ser. No. 388,437, filed Aug. 2, 1989.
This invention relates to 1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl, aryl, arylloweralkyl or heteroarylloweralkyl selected from the group consisting of pyridinylmethyl, pyridinylethyl, thienylmethyl, thienylethyl; or R.sub.2 and R.sub.3 together form a cycloalkane ring or 4 to 6 carbons or a spiro-fused aryl cycloalkane or heterocycloalkyl selected from the group consisting of piperidine and tetrahydropyran; X and Y are independently hydrogen, halogen, hydroxy, loweralkyl, loweralkoxy, nitro, amino or trifluoromethyl; m and n are independently integers of 1 to 3, the pharmaceutically acceptable acid addition salts thereof and, where applicable the optical, geometrical and stereoisomers and racemic mixtures thereof. The compounds of this invention display utility as analgesics, anticonvulsants, for enhancing memory and for the treatment of Alzheimer's disease.

REFERENCES:
patent: 3975531 (1976-08-01), Welstead
patent: 4182774 (1980-01-01), Welstead
patent: 4260767 (1981-04-01), Dusza
patent: 5064852 (1991-11-01), Howard
V. B. Avdeyev, et al., Khimiya Geterotsiklicheskikh Soedinenii, 524 (1983) published in the Soviet Union and entitled "6-Substituted-1-Heterocyclic Arylamino-3-Arylhydroxyindoles" and English translation thereof.
H. E. Baumgarten, et al., 82, 3977 (1960) published in the U.S. and entitled "Cinnolines. VI. The Structure of Neber's Lactam, A New Synthesis of 3-Cinnolinol".
G. Winters, et al., Chemical Abstracts 102, 78764w (1985) published in the U.S. and entitled "Synthesis and pregnancy terminating activity of pyrazolo[1,5-a]indols and quinolines".

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