3-(1-substituted-4-piperazinyl)-1H-indazoles
First Claim
1. A compound of the formula ##STR39## wherein R1 is hydrogen, lower alkyl, arylloweralkyl, acyl, cycloalkylloweralkylene, and phenylsulfonyl;
- wherein the term "aryl" signifies a phenyl group optionally substituted by one or more hydrogen or halogen atoms or loweralkyl, loweralkoxy, trifluoromethyl, nitro or amino groups;
the term "cycloalkyl" refers to a saturated hydrocarbon possessing at least one carbocyclic ring of three to seven carbon atoms; and
the term "acyl" refers to a substituent having the formula loweralkyl ##STR40## and R2 is hydrogen, lower alkyl, hydroxyloweralkyl of the formula ##STR41## where Z is selected from hydrogen, halogen, loweralkoxy, CF3, NO2 and NH2 ;
##STR42## where Z is as defined above, ##STR43## where Z is as defined above;
##STR44## where R3 and R4 are each independently hydrogen and loweralkyl;
##STR45## where Z is as defined above;
##STR46## where R'"'"' and R" are each independently hydrogen and loweralkyl;
X is hydrogen, loweralkyl, hydroxyl, halogen, loweralkoxy, CF3, NO2 ;
n is an integer of 1 to 4, with the proviso that if X is a chlorine atom attached at the 5 or 6 position of the benzene ring, R2 cannot be hydrogen or loweralkyl and R1 cannot be hydrogen or ##STR47## the pharmaceutically acceptable acid addition salts thereof; and
where applicable the geometric and optical isomers thereof and the racemic mixtures thereof.
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Abstract
This invention relates to 3-(1-substituted-4-piperazinyl)-1H-indazoles having the following formula ##STR1## wherein R1 is hydrogen, lower alkyl, arylloweralkyl, acyl, cycloalkylloweralkylene, and phenylsulfonyl: and R2 is hydrogen, lower alkyl, hydroxyloweralkyl of the formula ##STR2## where Z is selected from hydrogen, halogen, loweralkoxy, CF3, NO2, and NH2 ; ##STR3## where Z is as defined above; ##STR4## where Z is as defined above; ##STR5## where R3 and R4 are each independently hydrogen and loweralkyl; ##STR6## where Z is as defined above; ##STR7## where R'"'"' and R" are each independently hydrogen and loweralkyl; X is hydrogen, loweralkyl, hydroxyl, halogen, loweralkoxy, CF3, NO2 and amino; n is an integer of 1 to 4, with the further proviso that R2 is not loweralkyl when R1 is hydrogen or acyl and X is chloro; the pharmaceutically acceptable acid addition salts thereof and where appropriate the geometric isomers, the stereoisomers and racemic mixtures thereof. The compounds of this invention display utility as analgesic and antipsychotic agents.
143 Citations
187 Claims
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1. A compound of the formula ##STR39## wherein R1 is hydrogen, lower alkyl, arylloweralkyl, acyl, cycloalkylloweralkylene, and phenylsulfonyl;
- wherein the term "aryl" signifies a phenyl group optionally substituted by one or more hydrogen or halogen atoms or loweralkyl, loweralkoxy, trifluoromethyl, nitro or amino groups;
the term "cycloalkyl" refers to a saturated hydrocarbon possessing at least one carbocyclic ring of three to seven carbon atoms; and
the term "acyl" refers to a substituent having the formula loweralkyl ##STR40## and R2 is hydrogen, lower alkyl, hydroxyloweralkyl of the formula ##STR41## where Z is selected from hydrogen, halogen, loweralkoxy, CF3, NO2 and NH2 ;
##STR42## where Z is as defined above, ##STR43## where Z is as defined above;
##STR44## where R3 and R4 are each independently hydrogen and loweralkyl;
##STR45## where Z is as defined above;
##STR46## where R'"'"' and R" are each independently hydrogen and loweralkyl;
X is hydrogen, loweralkyl, hydroxyl, halogen, loweralkoxy, CF3, NO2 ;
n is an integer of 1 to 4, with the proviso that if X is a chlorine atom attached at the 5 or 6 position of the benzene ring, R2 cannot be hydrogen or loweralkyl and R1 cannot be hydrogen or ##STR47## the pharmaceutically acceptable acid addition salts thereof; and
where applicable the geometric and optical isomers thereof and the racemic mixtures thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186)
- wherein the term "aryl" signifies a phenyl group optionally substituted by one or more hydrogen or halogen atoms or loweralkyl, loweralkoxy, trifluoromethyl, nitro or amino groups;
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135. The composition as defined in claim 135 wherein said compound is the hemifumarate.
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187. A compound of the formula ##STR51## wherein R9 is loweralkyl, CN and n is an integer of 1 to 4;
- and X is hydrogen, loweralkyl, hydroxy, halogen, loweralkoxy, CF3, NO2, NH2.
Specification
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- Resources
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Current AssigneeAventis Holdings Incorporated (Sanofi )
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Original AssigneeHoechst-Roussel Pharmaceuticals Incorporated (Sanofi )
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InventorsBordeau, Kenneth J., Strupczewski, Joseph T.
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Primary Examiner(s)Shen, Cecilia
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Application NumberUS07/405,161Time in Patent Office358 DaysField of Search544/230, 544/232, 544/366, 544/368, 514/254US Class Current514/80CPC Class CodesA61P 25/04 Centrally acting analgesics...A61P 25/18 Antipsychotics, i.e. neurol...C07D 231/56 Benzopyrazoles; Hydrogenate...C07D 401/12 linked by a chain containin...C07D 403/12 linked by a chain containin...C07D 413/12 linked by a chain containin...C07F 9/65583 each of the hetero rings co...
