1-(5-Amino-4H-1,2,4-triazol-3-yl)-4-substituted-piperazines

Claim 2

A compound selected from the group consisting of those of the formula: ##STR5## wherein R 1 is selected from the group consisting of alkyl having up to 3 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, allyl, benzyl, β-phenethyl, β-phenoxyethyl, 3,4,5-trimethoxyphenyl, 2-furyl, 2-quinolyl, 2-phenyl-2H-1,2,3-triazol-4-yl and a moiety of the formula: ##STR6## wherein R 2 is hydrogen, alkyl having up to 4 carbon atoms, fluoro, chloro, bromo, cyano, amino or dimethylamino and R 3 is hydrogen, methyl, fluoro, chloro, bromo or nitro; and the pharmacologically acceptable acid-addition salts thereof.

Claim 3

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-methylbenzyl)piperazine.

Claim 4

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-fluorobenzyl)piperazine.

Claim 5

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-phenethylpiperazine.

Claim 6

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(cyclohexylmethyl)piperazine.

Claim 7

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(o-fluorobenzyl)piperazine.

Claim 8

The compound according to claim 1, α-[4-(5-amino-4H-1,2,4-triazol-3-yl)-1-piperazinyl]-p-tolunitrile.

Claim 9

The compound according to claim 1, 2-[4-(5-amino-4H-1,2,4-triazol-3-yl)-1-piperazinylmethyl]-quinoline.

Claim 10

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-furfurylpiperazine.

Claim 11

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-dimethylaminobenzyl)piperazine.

Claim 12

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(3-phenylpropyl)piperazine.

Claim 13

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(o-bromo-p-dimethylaminobenzyl)piperazine.

Claim 14

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(m-chlorobenzyl)piperazine.

Claim 15

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(m-chloro-p-dimethylaminobenzyl)piperazine.

Claim 16

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-aminobenzyl)piperazine.

Claim 17

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(o-methylbenzyl)piperazine.

Claim 18

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(3,4,5-trimethoxybenzyl)piperazine.

Claim 19

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(m-methylbenzyl)piperazine.

Claim 20

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-[(2-phenyl-2H-1,2,3-triazol-4-yl)methyl]piperazine.

Claim 21

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-butylbenzyl)piperazine.

Claim 22

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3)-yl-4-(p-tert.-butylbenzyl)piperazine.

Claim 23

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(3-phenoxypropyl)piperazine.

Claim 24

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(o-nitrobenzyl)piperazine.

Claim 25

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(cyclopropylmethyl)piperazine.

Claim 26

The compound according to claim 1, 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-benzylpiperazine.

Claim 29

A composition of matter in dosage unit form comprising of the formula: ##STR9## from about 5 mg. to about 200 mg. of a compound selected from the group consisting of those wherein R 1 is selected from the group consisting of alkyl having up to 3 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, allyl, benzyl, β-phenethyl, β-phenoxyethyl, 3,4,5-trimethoxyphenyl, 2-furyl, 2-quinolyl, 2-phenyl-2H-1,2,3-triazol-4-yl and a moiety of the formula: ##STR10## wherein R 2 is hydrogen, alkyl having up to 4 carbon atoms, fluoro, chloro, bromo, cyano, amino or dimethylamino and R 3 is hydrogen, methyl, fluoro, chloro, bromo or nitro; and the pharmacologically acceptable acid-addition salts thereof; in association with a pharmaceutically acceptable carrier.

Claim 30

A composition of matter in dosage unit form comprising of the formula: ##STR9## from about 5 mg. to about 200 mg. of a compound selected from the group consisting of those wherein R 1 is selected from the group consisting of alkyl having up to 3 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, allyl, benzyl, β-phenethyl, β-phenoxyethyl, 3,4,5-trimethoxyphenyl, 2-furyl, 2-quinolyl, 2-phenyl-2H-1,2,3-triazol-4-yl and a moiety of the formula: ##STR10## wherein R 2 is hydrogen, alkyl having up to 4 carbon atoms, fluoro, chloro, bromo, cyano, amino or dimethylamino and R 3 is hydrogen, methyl, fluoro, chloro, bromo or nitro; and the pharmacologically acceptable acid-addition salts thereof; in association with a pharmaceutically acceptable carrier.

Claim 31

A process for producing a compound of the formula: ##STR11## wherein R 1 is selected from the group consisting of alkyl having up to 3 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, allyl, benzyl, β-phenethyl, β-phenoxyethyl, 3,4,5-trimethoxyphenyl, 2-furyl, 2-quinolyl, 2-phenyl-2H-1,2,3-triazol-4-yl and a moiety of the formula: ##STR12## wherein R 2 is hydrogen, alkyl having up to 4 carbon atoms, fluoro, chloro, bromo, cyano, amino or dimethylamino and R 3 is hydrogen, methyl, fluoro, chloro, bromo or nitro; which comprises reacting dimethyl cyanodithiominocarbonate with a piperazine of the formula: ##STR13## wherein R 1 is as described above, in ethanol at reflux for 4-18 hours, giving an N-cyano-4-substituted-1-piperazinecarboximidothioic acid, methyl ester of the formula ##STR14## which is then reacted with hydrazine hydrate in ethanol at reflux.

Claim 32

A process for producing a compound of the formula: ##STR11## wherein R 1 is selected from the group consisting of alkyl having up to 3 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, allyl, benzyl, β-phenethyl, β-phenoxyethyl, 3,4,5-trimethoxyphenyl, 2-furyl, 2-quinolyl, 2-phenyl-2H-1,2,3-triazol-4-yl and a moiety of the formula: ##STR12## wherein R 2 is hydrogen, alkyl having up to 4 carbon atoms, fluoro, chloro, bromo, cyano, amino or dimethylamino and R 3 is hydrogen, methyl, fluoro, chloro, bromo or nitro; which comprises reacting dimethyl cyanodithiominocarbonate with a piperazine of the formula: ##STR13## wherein R 1 is as described above, in ethanol at reflux for 4-18 hours, giving an N-cyano-4-substituted-1-piperazinecarboximidothioic acid, methyl ester of the formula ##STR14## which is then reacted with hydrazine hydrate in ethanol at reflux.

Claim 33

A compound selected from the group consisting of 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-chloro-α-phenylbenzyl)piperazine and the pharmacologically acceptable acid-addition salts thereof.

Claim 34

A compound selected from the group consisting of 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(p-chloro-α-phenylbenzyl)piperazine and the pharmacologically acceptable acid-addition salts thereof.

Claim 35

A compound selected from the group consisting of 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-cyclopentylpiperazine and the pharmacologically acceptable acid-addition salts thereof.

Claim 36

A compound selected from the group consisting of 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-cyclopentylpiperazine and the pharmacologically acceptable acid-addition salts thereof.