4H-quinolizin-4-one compounds exhibiting therapeutic activities

Claim 1

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration of from about 0.02 mg to 5 mg per kg of mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound corresponds to the formula: ##STR17## where R is an alkyl group or a phenylalkyl group; A is a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5 or 6 membered heterocyclic group; with the proviso that the heterocyclic group is bonded to the quinolizine ring at a nitrogen atom of the heterocyclic ring; or a pharmaceutically acceptable salt thereof.

Claim 2

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration of from about 0.02 mg to 5 mg per kg of mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound corresponds to the formula: ##STR17## where R is an alkyl group or a phenylalkyl group; A is a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5 or 6 membered heterocyclic group; with the proviso that the heterocyclic group is bonded to the quinolizine ring at a nitrogen atom of the heterocyclic ring; or a pharmaceutically acceptable salt thereof.

Claim 3

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration or from about 0.02 mg to 5 per kg of mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound corresponds to the formula: ##STR18## where R is an alkyl group or a phenylalkyl group; Ar is a substituted or unsubstituted phenyl group; or a pharmaceutically acceptable salt thereof.

Claim 4

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration or from about 0.02 mg to 5 per kg of mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound corresponds to the formula: ##STR18## where R is an alkyl group or a phenylalkyl group; Ar is a substituted or unsubstituted phenyl group; or a pharmaceutically acceptable salt thereof.

Claim 5

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration or from about 0.02 mg to 5 mg per kg mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound corresponds to the formula: ##STR19## where R is an alkyl group or a phenylalkyl group; Het is a 5 or 6 membered heterocyclic group; with the proviso that the heterocyclic group is bonded to the quinolizine ring at a nitrogen atom of the heterocyclic ring; or a pharmaceutically acceptable salt thereof.

Claim 6

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration or from about 0.02 mg to 5 mg per kg mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound corresponds to the formula: ##STR19## where R is an alkyl group or a phenylalkyl group; Het is a 5 or 6 membered heterocyclic group; with the proviso that the heterocyclic group is bonded to the quinolizine ring at a nitrogen atom of the heterocyclic ring; or a pharmaceutically acceptable salt thereof.

Claim 7

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration or from about 0.02 mg to 5 mg per kg of mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound is selected from the group consisting of 3-cyano-1-ethoxycarbonyl-2-phenyl-4H-quinolizin-4-one; 2-(4-biphenylyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-Bromophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-tertbutylphenyl)-4H-quinolizin-4-one; 3-cyano-2-(3,4-dimethoxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methylphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3,4-methylenedioxyphenyl)-4H-quinolizin-4-one; 3-cyano-2-(2,4-dichlorophenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-2-phenyl-1-propoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-methoxycarbonyl-2-phenyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-fluorophenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3-fluoro-4-methylphenyl)-4H-quinolizin-4-one; 3-cyano-2-(3,4-dimethylphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-ethoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-isopropoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3-methoxyphenyl)-4H-quinolizin-4-one; 2-(4-benzyloxyphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3,4,5-trimethoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-nitrophenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(2-methoxyphenyl)-4H-quinolizin-4-one; 2-(3-bromophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin4-one; 2-(3-benzyloxy-4-methoxyphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-benzyloxy-3-methoxyphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methylthiophenyl)-4H-quinolizin-4-one; 2(4-acetylaminophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-benzoylphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-2-(2,3-dimethoxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-2-(3,5-dimethoxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-hydroxyphenyl)-4H-quinolizin-4-one; 3-cyano-2-(3,4-dihydroxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-hydroxy-3-methoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3-hydroxy-4-methoxyphenyl)-4H-quinolizin-4-one; 2-(4-aminophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-methylthio-4H-quinolizin-4-one; 3-cyano-2-methylthio-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-piperidino-4H-quinolizin-4-one; 3-cyano-1-(3-phenylpropoxycarbonyl)-2-piperidino-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(1-pyrrolidinyl)-4H-quinolizin-4-one; 3-cyano-1-(3-phenylpropoxycarbonyl)-2-(1-pyrrolidinyl)-4Hquinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-[4-(2-hydroxyethyl)piperazin-1-yl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-formylpiperazin-1-yl)-4H-quinolizin-4-one; 3-cyano-2-(4-formylpiperazin-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methylpiperazin-1-yl)-4H-quinolizin-4one; 3-cyano-2-(4-methylpiperazin-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 2-(4-benzylpiperidino)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-benzylpiperidino)-3-cyano-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-phenylpiperidino)-4H-quinolizin-4-one; 3-cyano-2-(4-phenylpiperidino)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-morpholino-4H-quinolizin-4-one; 3-cyano-2-morpholino-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(imidazol-1-yl)-4H-quinolizin-4-one; 3-cyano-2-(imidazol-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(1,3,4-triazol-1-yl)-4H-quinolizin-4-one; 3-cyano-1-(3-phenylpropoxycarbonyl)-2-(1,3,4-triazol-1-yl)-4H-quinolizin-4-one; 3-cyano-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-morpholinocarbonylmethylpiperazin-1-yl)-4H-quinolizin-4-one; 3-cyano-2-4-morpholinocarbonylmethylpiperazin-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; and 3-cyano-1-(2-hydroxyethyloxycarbonyl)-2-piperidino-4H-quinolizin-4-one;or a pharmaceutically acceptable salt thereof.

Claim 8

A method for the treatment of allergic bronchial asthma, allergic rhinitis, atopic dermatitis and hypersensitiveness diseases associated with immunoglobulin E-antibody formation in a mammal which comprises administering an effective dosage from about 0.1 mg to 10 mg per kg of mammal weight by oral administration or from about 0.02 mg to 5 mg per kg of mammal weight by parenteral administration per day of an immunoglobulin E-antibody formation-inhibiting 4H-quinolizin-4-one compound to the mammal; wherein the 4H-quinolizin-4-one compound is selected from the group consisting of 3-cyano-1-ethoxycarbonyl-2-phenyl-4H-quinolizin-4-one; 2-(4-biphenylyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-Bromophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-tertbutylphenyl)-4H-quinolizin-4-one; 3-cyano-2-(3,4-dimethoxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methylphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3,4-methylenedioxyphenyl)-4H-quinolizin-4-one; 3-cyano-2-(2,4-dichlorophenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-2-phenyl-1-propoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-methoxycarbonyl-2-phenyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-fluorophenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3-fluoro-4-methylphenyl)-4H-quinolizin-4-one; 3-cyano-2-(3,4-dimethylphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-ethoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-isopropoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3-methoxyphenyl)-4H-quinolizin-4-one; 2-(4-benzyloxyphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3,4,5-trimethoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-nitrophenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(2-methoxyphenyl)-4H-quinolizin-4-one; 2-(3-bromophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin4-one; 2-(3-benzyloxy-4-methoxyphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-benzyloxy-3-methoxyphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methylthiophenyl)-4H-quinolizin-4-one; 2(4-acetylaminophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-benzoylphenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-2-(2,3-dimethoxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-2-(3,5-dimethoxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-hydroxyphenyl)-4H-quinolizin-4-one; 3-cyano-2-(3,4-dihydroxyphenyl)-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-hydroxy-3-methoxyphenyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(3-hydroxy-4-methoxyphenyl)-4H-quinolizin-4-one; 2-(4-aminophenyl)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-methylthio-4H-quinolizin-4-one; 3-cyano-2-methylthio-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-piperidino-4H-quinolizin-4-one; 3-cyano-1-(3-phenylpropoxycarbonyl)-2-piperidino-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(1-pyrrolidinyl)-4H-quinolizin-4-one; 3-cyano-1-(3-phenylpropoxycarbonyl)-2-(1-pyrrolidinyl)-4Hquinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-[4-(2-hydroxyethyl)piperazin-1-yl-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-formylpiperazin-1-yl)-4H-quinolizin-4-one; 3-cyano-2-(4-formylpiperazin-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-methylpiperazin-1-yl)-4H-quinolizin-4one; 3-cyano-2-(4-methylpiperazin-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 2-(4-benzylpiperidino)-3-cyano-1-ethoxycarbonyl-4H-quinolizin-4-one; 2-(4-benzylpiperidino)-3-cyano-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-phenylpiperidino)-4H-quinolizin-4-one; 3-cyano-2-(4-phenylpiperidino)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-morpholino-4H-quinolizin-4-one; 3-cyano-2-morpholino-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(imidazol-1-yl)-4H-quinolizin-4-one; 3-cyano-2-(imidazol-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(1,3,4-triazol-1-yl)-4H-quinolizin-4-one; 3-cyano-1-(3-phenylpropoxycarbonyl)-2-(1,3,4-triazol-1-yl)-4H-quinolizin-4-one; 3-cyano-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; 3-cyano-1-ethoxycarbonyl-2-(4-morpholinocarbonylmethylpiperazin-1-yl)-4H-quinolizin-4-one; 3-cyano-2-4-morpholinocarbonylmethylpiperazin-1-yl)-1-(3-phenylpropoxycarbonyl)-4H-quinolizin-4-one; and 3-cyano-1-(2-hydroxyethyloxycarbonyl)-2-piperidino-4H-quinolizin-4-one;or a pharmaceutically acceptable salt thereof.