1-Phenyl-3-(1-piperazinyl)-1h-indazoles, a process and intermediates for their preparation, and the use thereof as medicaments

Claim 2

A compound of the formula I wherein n is an integer having a value of 0 or 1; m is an integer having a value of 0 to 2 inclusive; X and Y are independently halogen, loweralkyl, loweralkoxy, loweralkylthio, diloweralkylamino, loweralkylamino, amino, nitro, cyano, mercapto, hydroxy, or trifluoromethyl, wherein for each value of m, Y may be the same or different; and R is hydrogen, loweralkyl, cycloalkylloweralkyl, loweralkenyl, hydroxyloweralkyl, diloweralkylaminoloweralkyl, diloweralkylphosphinyl­loweralkyl, cyano, loweralkylcarbonyl, loweralkanoyl, aminocarbonyl, loweralkylaminocarbonyl, or a group of the formula wherein q is an integer having a value of 0 to 5, inclusive, X¹ is halogen, loweralkyl, loweralkoxy, loweralkylthio, diloweralkylamino, loweralkylamino, amino, nitro, cyano, mercapto, hydroxy, or trifluoromethyl, and p is an integer having a value of 0 to 2 inclusive, wherein for each value of p, X¹ may be the same or different; the geometrical isomers, optical antipodes or pharmaceutically acceptable acid addition salts thereof.

Claim 3

A compound according to claim 1 wherein n is 0, m is 0 or 1, Y is halogen or trifluoromethyl and R is hydrogen, loweralkyl, cycloalkylloweralkyl, loweralkenyl, loweralkanoyl, aminocarbonyl, loweralkylaminoloweralkyl, diloweralkylaminoloweralkyl or diloweralkylphosphinyl­loweralkyl.

Claim 4

A compound according to claim 2 wherein R is hydrogen, loweralkyl, or cycloalkylloweralkyl.

Claim 5

The compound of claim 3 which is 1-phenyl-3-(1-­piperazinyl)-1H-indazole, or a pharmaceutically acceptable acid addition salt thereof.

Claim 6

The compound according to claim 3 which is 1-phenyl-­3-(4-methyl-1-piperazinyl)-1H-indazole or a pharmaceutically acceptable acid addition salt thereof.

Claim 7

The compound according to claim 3 which is 1-(4-­fluorophenyl)-3-(4-methyl-1-piperazinyl)-1H-indazole or a pharmaceutically acceptable acid addition salt thereof.

Claim 8

The compound according to claim 2 which is 3-[4-­(dimethylphosphinylmethyl)-1-piperazinyl]-1-phenyl-­1H-indazole or a pharmaceutically acceptable acid addition salt thereof.

Claim 9

The compound according to claim 3 which is 3-(4-ethyl-­1-piperazinyl)-1-[4-(trifluoromethyl)phenyl]-1H-­indazole or a pharmaceutically acceptable acid addition salt thereof.

Claim 10

A compound of the formula II wherein R is loweralkyl, loweralkoxycarbonyl or a group of the formula wherein X¹ is halogen, loweralkyl, loweralkoxy, loweralkylthio, diloweralkylamino, nitro, cyano, or trifluoromethyl, and p is an integer having a value of 0 to 2 inclusive, wherein for each value of p, X¹ may be the same or different; X and Y are independently halogen, loweralkyl, loweralkoxy, loweralkylthio, diloweralkylamino, nitro, cyano, or trifluoromethyl, n is an integer having a value of 0 or 1; m is an integer having a value of 0 to 2 inclusive; wherein for each value of m, Y may be the same or different; and Z is fluorine or chlorine; the geometrical isomers, optical antipodes, or pharmaceutically acceptable acid addition salts thereof.

Claim 11

A compound of the formula II wherein R is loweralkyl, loweralkoxycarbonyl or a group of the formula wherein X¹ is halogen, loweralkyl, loweralkoxy, loweralkylthio, diloweralkylamino, nitro, cyano, or trifluoromethyl, and p is an integer having a value of 0 to 2 inclusive, wherein for each value of p, X¹ may be the same or different; X and Y are independently halogen, loweralkyl, loweralkoxy, loweralkylthio, diloweralkylamino, nitro, cyano, or trifluoromethyl, n is an integer having a value of 0 or 1; m is an integer having a value of 0 to 2 inclusive; wherein for each value of m, Y may be the same or different; and Z is fluorine or chlorine; the geometrical isomers, optical antipodes, or pharmaceutically acceptable acid addition salts thereof.

Claim 12

A pharmaceutical composition which comprises as the action ingredient a compound as defined in claim 1 in association with a pharmaceutically suitable carrier therefor.

Claim 13

Use of a compound as defined in claim 1 for the preparation of a medicament having analgesic, anti-­convulsant and/or antidepressant activity.

Claim 14

A process for the preparation of a compound as defined in claim 1, which comprises a) treating a compound of the formula II wherein X, Y, m and n are as defined in claim 9, R is loweralkyl, loweralkoxycarbonyl or phenyl and Z is fluorine or chlorine, with an inorganic base in the presence of an inert organic solvent, b) optionally hydrolyzing a compound of the formula I, wherein R is loweralkoxycarbonyl to afford a compound of the formula I, where R is hydrogen, c) optionally treating a compound of the formula I where R is hydrogen, with a halide of the formula R¹X² wherein R¹ is loweralkyl, cycloalkylloweralkyl, hydroxyloweralkyl, loweralkenyl, diloweralkyl­phosphinylloweralkyl, diloweralkylamino, loweralkanoyl, cyano or a radical of the formula wherein q, p, and X¹ are as previously described, and X² is halogen, to afford a compound of the formula I where R has the meaning of R¹ as previously defined, d) optionally treating a compound of the formula I wherein R is hydrogen, with formic acid in the presence of acetic anhydride to afford a compound of the formula I where R is the formyl group, e) optionally treating a compound of the formula I wherein R is hydrogen with a nitro-substituted urea of the formula NO₂NH- -NHR² wherein R² is hydrogen or loweralkyl, to afford a compound of the formula I wherein R is aminocarbonyl or loweralkylaminocarbonyl, f) and optionally preparing in a routine manner known in the art a pharmaceutically acceptable acid addition salt thereof.