Kali-chemie Pharma Gmbh

Dimitri Yavordios

Daniel Jasserand

Horst Zeugner

Wolfgang Milkowski

Henning Heinemann

Marie-Odile Christen

Dominique Biard

5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds of the Formula ##STR1## in which R.sub.1 is a straight-chain, branched or cyclic alkyl group with up to 6 carbon atoms, Z is an alkylene chain with 2 to 4 carbon atoms, and 1-phenyl substituent is an optionally substituted phenyl ring, and R.sub.4 is a phenyl or pyridyl group which is optionally substituted and their preparation are described. The compounds have pharmacological, particularly antiallergic, properties.

Antiallergic 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds

Compounds corresponding to the formula: ##STR1## wherein R.sub.1 and R.sub.3 each represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl; R.sub.2 and R.sub.4 each represent hydrogen, halogen, lower alkyl or lower alkoxy; Z represents an alkylene radical with 2 to 6 carbon atoms and Y' is halogen, hydroxyl, lower alkanesulphonyl, benzenesulphonyl, or lower alkyl or halogen substituted benzenesulphonyl, and acid addition salts thereof, with the proviso the Y' is other than chlorine if R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each are hydrogen and Z is ethylene or propylene. The claimed compounds are useful intermediates in the synthesis of 1-phenyl-2-[(4-substituted piperazinyl) alkyl]-1,2-dihydro-3H-indazol-3-ones which exhibit antiallergic activity.

1-Phenylindazol-3-one compounds

Intermediates of the isomeric formulae II or III ##STR1## wherein R.sub.1 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxyl, trifluoromethyl or lower alkanoyloxy group,

1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates

New 1-phenylindazol-3-one compounds are described which have the formula I ##STR1## where R.sub.1 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy or trifluoromethyl radical, R.sub.2 is a hydrogen or halogen atom, or a lower alkyl or lower alkoxy radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy or trifluoromethyl radical, R.sub.4 is a hydrogen or halogen, atom, or a lower alkyl or lower alkoxy radical, Z is an alkylene radical with 2 to 6 carbon atoms and R.sub.5 is an unsubstituted or substituted pyridyl radical, a thienyl radical or an unsubstituted or substituted phenyl radical. The compounds have pharmacological actions, for example antiallergic actions. Methods of preparing these compounds are described as well as intermediates useful in these methods. Pharmaceutical compositions containing the compounds are also described.

1-Phenylindazole-3-one compounds, process and intermediates for their

New 1,5-diphenylpyrazolin-3-one compounds and a method of preparing them are described. The compounds have the general formula I ##STR1## where R.sub.1 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or lower alkanoyloxy radical, R.sub.2 is a hydrogen or halogen atom, or a lower alkyl, or lower alkoxy radical, or R.sub.1 and R.sub.2 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or lower alkanoyloxy radical, R.sub.4 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy radical, or R.sub.3 and R.sub.4 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy radical, Z is an alkylene radical with 2 to 6 carbon atoms and R.sub.5 is an optionally substituted pyridyl radical, a thienyl radical or an optionally substituted phenyl radical. The compounds have pharmacological properties, for example antiallergic properties.

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Chatillon sur Chalaronne, France

Dimitri Yavordios