Hodogaya Chemical Co., Ltd.

Mochida Pharmaceutical Co., Ltd.

Akinori Haga

Kazuo Kato

Ei Mochida

Hiroki Tokunaga

Akio Uemura

The present invention relates to intermediate compounds to produce novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites. The present invention is based on two characters. One is the selection of acyl substituents of 2,3-dihydro-4(1H)-quinolinone at 1-position, namely propionyl, t-butylcarbonyl, benzoyl, 2-bromobenzoyl, 4-chlorobenzoyl, 2-methylbenzoyl, 2-ethylbenzoyl, 2,3-dimethoxybenzoyl, 2,4-dichlorobenzoyl, 4-chloro-2-methyl benzoyl or 2-chloro-4-nitrobenzoyl. The other is the selection of substituents and positional specificity at 6- or 7-position, namely halogen atom, methoxy, trifluoromethyl or dimethylamino group. 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives which are made from the intermediate compounds of the present invention have potent hypotensive, antioedematous and diuretic effect as well as an activity to remove ascites, and are extremely useful for the treatment of diseases and disorders mentioned above.

Intermediate compounds of 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime

The present invention relates to novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime-O-sulfonic acid compound, processes for producing said compounds, intermediate compounds to produce said compounds and compositions containing said compounds with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites. The present invention is based on the selection of 1-acyl-7-halo-2,3-dihydro-4(1H)-quinolinone-4-oxime-O-sulfonic acid compounds, namely heterocyclic-or fused heterocyclic- carbonyl derivatives at 1 position. The compounds of the present invention containing these substituents have potent hypotensive, antioedematous and diuretic effect as well as an activity to remove ascites and are extremely useful for the treatment of diseases and disorders mentioned above.

1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, process for

The present invention relates to novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, processes for producing said derivatives, intermediate compounds to produce said derivatives, processes to produce said intermediate compounds, and compositions containing said derivatives with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites. The present invention is based on the selection of 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, namely O-sulfate, O-mesylate, O-methylphosphate and O-carboxymethyl ether, especially O-sulfate of 4-oxime. The compounds of the present invention containing these substituents have potent hypotensive, anti-oedematous and diuretic effect as well as an activity to remove ascites and are extremely useful for the treatment of diseases and disorders mentioned above.

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Kawasaki, Japan

Akinori Haga