Dainippon Pharmaceutical Company, Limited

Hitoshi Uno

Hideo Nakamura

Masanao Shimizu

Haruki Nishimura

Mikio Kurokawa

Kagayaki Natsuka

Noriaki Shimokawa

Yasutaka Nagai

Katsuhiko Hino

Yoshinobu Masuda

Toshiaki Kadokawa

Tadahiko Karasawa

Tatsuya Kon

Fuminori Sato

Katsuyoshi Kawashima

Katsumi Ishii

Tokuhiko Shindo

Yoshinori Nishikawa

Jun-ichi Matsumoto

Shinichi Nakamura

Kiyoshi Furukawa

Naonobu Hatano

Shunsuke Naruto

Junji Nakano

Teruyuki Miyamoto

Tetsuo Hirooka

Tsugutaka Ito

Heteroarylcarboxamide derivatives, process for preparing the same and

Dibenz[b,e]oxepin derivatives and pharmaceutical composition containing

Compounds of the formula: ##STR1## wherein X is alkylene or --(CR.sub.6 .dbd.CR.sub.7).sub.r -- wherein R.sub.6 is H, alkyl or phenyl, R.sub.7 is H, alkyl, cyano or phenyl, and r is 1 or 2; A is alkylene or alkylene interrupted by at least one double bond; R.sub.1 is H, halogen, alkyl, alkoxy, alkylthio, cycloalkyloxy, cycloalkylthio, alkoxycarbonyl, carboxy, phenyl, phenoxy, phenylthio, 3-pyridyloxy or 3-pyridylthio; R.sub.2 is H, hydroxy, alkanoyloxy or alkoxycarbonyloxy, or adjacent R.sub.1 and R.sub.2 may combine to form tetramethylene or --CH.sub.2 OCR.sub.8 R.sub.9 O-- (R.sub.8 and R.sub.9 are alkyl); R.sub.3 is H, alkyl or hydroxyalkyl; R.sub.4 is H or alkyl; R.sub.5 is phenyl, heteroaryl or --(CH.sub.2).sub.m --CHR.sub.10 R.sub.11 (R.sub.10 is H or phenyl, R.sub.11 is phenyl or pyridyl and m is 0 to 2); p is 0 or 1; and q is 2 or 3; the phenyl group or moiety being optionally substituted, and a salt thereof, process for the preparation thereof, and pharmaceutical composition containing the same. Said compounds and salts thereof show excellent antiallergic activity mainly through 5-lipoxygenase inhibiting activity, antihistamine activity and/or inhibitory activity against chemical mediator release and useful for treatment of allergic diseases.

.omega.-(3-pyridyl)alkenamide derivatives and anti-allergenic

2-(1-piperazinyl)-4-substituted phenylquinoline derivatives, processes

Calcium antagonist piperazine derivatives, and compositions therefor

Use of a compound of the formula: ##STR1## wherein R is hydrogen atom or ethyl group, or a pharmaceutically acceptable salt thereof for prophylaxis and/or treatment of peptic ulcer, and a method for prophylaxis and/or treatment of peptic ulcer disease which comprises administering an effective amount of the above-mentioned compound to warm blooded aninal, especially human. Said active compounds have excellent pharmacological activities such as inhibition of ulceration and inhibition of gastric secretion, and hence, are useful as an anti-peptic ulcer agent.

Anti-peptic ulcer agent

The present invention relates to a 1,8-naphthyridine derivative of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each hydrogen or lower alkyl having 1 to 5 carbon atoms; and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents.

Antibacterial

1-(2,3-Dimethyl-4-methoxyphenyl)-2-methyl-3-(1-pyrrolidinyl)-1-propanone and its pharmaceutically acceptable acid addition salts, which are useful as centrally acting muscle relaxants in the treatment of spasticity in mammals including humans, process for the preparation thereof, and pharmaceutical composition containing said compound as an active ingredient.

1-(2,3-Dimethyl-4-methoxyphenyl)-2-methyl-3-(1-pyrrolidinyl)-1-propanone

Novel acetic acid derivatives of the formula: ##STR1## wherein X is oxygen or sulfur; R.sub.1 is hydrogen or a lower alkyl; R.sub.2 is hydroxy, an alkoxy, an alkenyloxy, a cycloalkyloxy, an aryloxy, a substituted aryloxy, an aryl-lower alkoxy, a substituted aryl-lower alkoxy, an aryl-lower alkenyloxy, a substituted aryl-lower alkenyloxy, an .omega.-disubstituted amino-lower alkoxy, a lower alkoxycrbonyl-lower alkoxy, a lower alkoxy-lower alkoxy, a hydroxy-lower alkoxy-lower alkoxy, an acyl-lower alkoxy, or a group ##STR2## wherein R.sub.3 is hydrogen, hydroxy, a lower alkyl, an aryl-lower alkyl, a hydroxy-lower alkyl, or a carboxy-lower alkyl, R.sub.4 is hydrogen, a lower alkyl or a hydroxy-lower alkyl, or the R.sub.3 and R.sub.4 may combine together with the nitrogen atom to which they are joined to form a heterocyclic group; and the group --CH(R.sub.1)COR.sub.2 is joined to the carbon atom at 2- or 3-position, and pharmaceutically acceptable salts thereof, processes for their preparation, and pharmaceutical compositions containing these compounds. They have excellent anti-inflammatory, analgesic and antipyretic activities with weak ulcerogenicity in the gastrointestinal tract and toxicity.

Acetic acid derivatives and composition containing the same

Novel 4-(2'-pyridylamino)phenylacetic acid derivatives of the formula: ##STR1## wherein R.sub.1 is hydrogen, a halogen, a lower alkyl having 1 to 3 carbon atoms, or nitro, R.sub.2 is hydrogen, a halogen, or a lower alkyl having 1 to 3 carbon atoms, R.sub.3 is hydrogen, a halogen, or a lower alkyl having 1 to 3 carbon atoms, R.sub.4 is hydrogen or a lower alkyl having 1 to 3 carbon atoms, R.sub.5 is hydrogen or --CH.sub.2 CH.sub.2 OR.sub.6 wherein R.sub.6 is a lower alkyl having 2 or 3 carbon atoms and being substituted with 1 or 2 hydroxy groups, provided that R.sub.1 or R.sub.2 is not 4-halogen, or pharmaceutically acceptable salts thereof, and a process for the preparation thereof, pharmaceutical composition of said compounds, and a method of using said compounds as anti-inflammatory and analgesic agents. They have excellent anti-inflammatory and analgesic activities with an extremely weak ulcerogenicity in the gastrointestinal tract. Some of the compounds have superior inhibitory activity against chronic inflammation mediated by cellular immunity.

4-(2-Pyridylamino)phenylacetic acid derivatives

Novel dibenz[b,f]oxepin and dibenzo[b,f]thiepin derivatives of the formula ##STR1## wherein X is an oxygen or sulfur atom, each of R.sub.1 and R.sub.2 is a hydrogen atom or a methyl group, and R.sub.3 is a hydrogen atom or a 2-(2-hydroxyethoxy)ethyl group; provided that when R.sub.1 is a hydrogen atom, the group ##STR2## is a group other than a 1-carboxyethyl group; and when X is a sulfur atom, both R.sub.1 and R.sub.2 are methyl groups; and pharmaceutically acceptable salts of said compounds in which R.sub.3 is a hydrogen atom. Compositions of said compounds, processes for the preparation of said compounds, and a method of using said compounds are also provided. These novel compounds have excellent anti-inflammatory, analgesic and antipyretic activities.

Dibenz[b,f]oxepin and dibenzo[b,f]thiepin derivatives, process for

2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline and its pharmaceutically acceptable acid addition salts, which are useful as antidepressant agents in the treatment of depression or depressive state in mammals including humans, and processes for the preparation thereof.

2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline, process for preparation

Methane-sulfonamide derivatives of the formula: ##STR1## wherein R.sub.1 is hydrogen or a halogen atom, R.sub.2 and R.sub.3 are the same or different and are each hydrogen or a straight or branched alkyl having 1 to 3 carbon atoms, and one of X and Y is a carbon atom and another is a nitrogen atom, provided that the group: --CH.sub.2 SO.sub.2 NR.sub.2 R.sub.3 is bonded to the carbon atom of either of X and Y, and an alkali metal salt thereof, and a process for the preparation of said methane-sulfonamide derivatives. Said compounds have an excellent anticonvulsant activity and are useful as anticonvulsants for controlling convulsions and seizures in patients with epilepsy.

Methane-sulfonamide derivatives, the preparation thereof and composition

1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives of the formula: ##STR1## wherein X is 2- or 3-hydroxy, 2-methoxy, 3-methyl, 3-alkoxy having 1 to 4 carbon atoms, or 2- or 3-alkanoyloxy having 2 to 5 carbon atoms; R is allyl, 3-hydroxyisoamyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, propyl, an unsubstituted monocycloalkyl having 5 to 8 carbon atoms, 2-chlorophenyl, or a phenyl substituted by hydroxy or methoxy; with proviso that when X is a substituent at position 2, R is cyclohexyl and when X is 3-methyl, R is 2-methoxyphenyl or an unsubstituted monocycloalkyl having 6 to 8 carbon atoms, and their pharmaceutically acceptable salts, and the preparation thereof, and analgesic or antitussive compositions containing the same as the essentially active ingredient.

1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives and

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Takatsuki, Japan

Hitoshi Uno