Sumitomo Chemical Company, Limited

Sumitomo Pharmaceuticals Company Limited

Shigeaki Morooka

Hisao Yamamoto

Shigeho Inaba

Michihiro Yamamoto

Masao Koshiba

Atsuyuki Kojima

Masao Enomoto

Yuzuru Sanemitsu

Masato Mizutani

Shunji Aono

Yoshihiro Komuro

You Tanabe

Hiroshi Noguchi

Toshiaki Komatsu

Katsumi Tamoto

Hiroaki Masumori

Youichi Hara

Naruhito Masai

Akira Matuura

Nobuyuki Hara

Thiazolidin-4-one derivative represented by the following general formula (I) and acid addition salts thereof ##STR1## wherein; R.sup.1 and R.sup.2 are the same or different and denote each

Thiazolidin-4-one derivatives and acid addition salts thereof useful for

A 2-pyridyl-thiazolidin-4-one derivative represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom, an C.sub.1 -C.sub.20 alkyl group, an C.sub.2 -C.sub.20 alkenyl group, an C.sub.2 -C.sub.20 alkynyl group, an aryl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group which may have a substituent, R.sub.3 is a hydrogen atom, an C.sub.1 -C.sub.20 alkyl group, an C.sub.2 -C.sub.20 alkenyl group, an C.sub.2 -C.sub.20 alkynyl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group which may have a substituent, P is a pyridyl group or its N-substituted pyridinium salt which may have a substituent, said substituent being selected from the group consisting of halogen atom, cyano group, hydroxy group, amino group, lower alkyl group, lower alkoxy group, lower alkylamino group, halogenated lower alkyl group, acyl group, acyloxy group, acylthio group, acylamino group, carboxyl group, lower alkoxycarbonyl group, carbamoyl group, lower alkyl substituted carbamoyl group, heterocyclic group, and lower cycloalkyl group, and n represents an integer of 0, 1 or 2, or a pharmaceutically acceptable salts thereof and an anti-ulcer agent which contains, as an effective ingredient, said 2-pyridyl-thiazolidine-4-one derivative or a pharmaceutically acceptable salt thereof.

Certain pyridyl-thiazolidin-4-one having anti-ulcer activity

Thiazolidin-4-one derivative represented by the folowing general formula (I) and acid addition salts thereof ##STR1## wherein; R.sup.1 and R.sup.2 are the same or different and denote each

Thiazolidin-4-one derivatives useful for treating diseases caused by

Imidazo- and pyrimido[2,1-b]quinazolines of the formula, ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, trifluoromethyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or R.sub.1 and R.sub.2 may together represent methylenedioxy; R.sub.3 is hydrogen, C.sub.1-4 alkyl, phenyl or substituted phenyl of the formula, ##STR2## (wherein R is halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy); R.sub.4 is hydrogen, C.sub.1-4 alkyl or aralkyl; and A is C.sub.2-3 alkylene wich may be optionally substituted by one or two C.sub.1-2 alkyl radicals, and pharmaceutically acceptable acid addition salts thereof, are prepared by reacting a compound of the formula, ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A are as defined above; and X is oxygen or sulfur, with a halogenating agent at a temperature of about 30.degree. C. to about 180.degree. C. In the above imidaxo- and pyrimido[2,1-b]quinazolines, those having C.sub.1-4 alkyl, or ##STR4## as R.sub.3 are novel compounds and show antidepressant and/or antihypertensive activities.

Imidazo- and pyrimido[2,1-b]quinazolines and preparation thereof

Viral infections caused by viruses which belong to, e.g. Pox, Herpes, Adeno, Myxo, Paramyxo groups are controlled by administering an effective amount of quinazoline derivatives of the formula ##STR1## wherein R.sub.1 is cyclo, C.sub.3 -C.sub.8 alkyl, cyclo C.sub.3 -C.sub.8 alkyl C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.2-C.sub.5 alkenyloxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, polyhalo C.sub.1- C.sub.4 alkyl, a group of the formula ##STR2## (wherein m is an integer of 1 to 3; and R.sub.4 and R.sub.5 are individually C.sub.1 -C.sub.4 alkyl, and may form together with the adjacent nitrogen atom an unsubstituted or C.sub.1 -C.sub.4 alkyl substituted 3 to 6 membered saturated heterocyclic ring, which may contain another nitrogen or oxygen atom) or a group of the formula --C.sub.n H.sub.2n --R.sub.6 (wherein n is 0 or an integer of 1 to 3; and R.sub.6 is a phenyl group, a substituted phenyl group or an aromatic or non-aromatic 3 to 6 membered heterocyclic ring which contains one or two hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atom, and may be optionally substituted by one or two C.sub.1 -C.sub.4 alkyl, and further, those substituents on adjacent carbon atoms may be joined to form a benzene or cyclohexane ring); R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, trifluoromethyl or nitro; and R.sub.3 is phenyl, substituted phenyl, cyclo C.sub.3 -C.sub.6 alkyl, pyridyl, furyl, nitrofuryl, thienyl, nitrothienyl, methylthienyl or pyrimidinyl.

Nitroquinazolinone compounds having antiviral properties

An improved process for preparing indole derivatives of the formula, ##STR1## wherein R.sub.1 and R.sub.2 each are hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, nitro, cyano or trifluoromethyl, or when taken together, form methylenedioxy; R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, nitro, cyano or dimethylamino; and R.sub.4 is hydrogen or halogen, which comprises cyclizing a compound of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above, with an acidic condensing agent. The indole derivatives of the formula (I) mentioned above are useful as a key intermediate for the preparation of benzodiazepines, which are useful as tranquilizers, muscle relaxants and the like.

Preparation of indole derivatives

Triazoloquinazolines of the formula, ##STR1## wherein R.sub.1 is C.sub.1.sub.-4 alkyl or aryl; R.sub.2 and R.sub.3 are independently hydrogen, halogen, trifluoromethyl, nitro, C.sub.1.sub.-4 alkyl or C.sub.1.sub.-4 alkoxy, or R.sub.2 and R.sub.3 together may form methylenedioxy; and R.sub.4 is hydrogen, C.sub.1.sub.-4 alkyl, aralkyl, C.sub.1.sub.-4 haloalkyl, or C.sub.3.sub.-6 cycloalkyl; and pharmaceutically acceptable acid addition salts thereof are prepared by (a) reacting a 2-hydrazinoquinazoline derivative with a carboxylic acid or reactive derivative thereof, (b) cyclizing a 2-acylhydrazinoquinazoline derivative with heating or (c) reacting a triazolylbenzophenone derivative with ammonia. Said triazoloquinazolines and pharmaceutically acceptable acid addition salts thereof show excellent anti-inflammatory and analgesic activities.

Triazoloquinazolines

Quinazolinone derivatives of the formula, ##SPC1## Wherein R is a polyalicyclic hydrocarbon group; R.sup.1 and R.sup.2 are independently a hydrogen atom, a nitro group, a trifluoromethyl group or a methylsulfonyl group; R.sup.3 is a phenyl group, a substituted phenyl group, a pyridyl group or a thienyl group; and n is 0 or an integer of 1 to 3, have potent antiviral activity with low toxicities. These compounds can be prepared using a variety of processes analogous to known methods, for example, by oxidizing a 3,4-dihydro-2(1H)-quinazolinone having a polyalicyclic hydrocarbon group bonded through an alkylene group at the 1 position.

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Kawanishi, Japan

Shigeaki Morooka