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US 2004/0110746 A1Published application
Piperazinyl and diazapanyl benzamides and benzthioamides
AssigneeJanssen Pharmaceutica NV
InventorsRichard L. Apodaca, Jill A. Jablonowski, Kiev S. Ly, Chandravadan R. Shah, Devin M. Swanson, Wei Xiao
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Abstract
Substituted piperazinyl and diazepanyl benzamides and benzthioamides of formula (I), compositions containing them, and methods of making and using them to treat histamine-mediated conditions.
Claims55
A composition comprising a compound of formula (I):
- 79
- wherein
- R1 is C1-10 alkyl, C3-8 alkenyl, C3-8 cycloalkyl, (C3-8 cycloalkyl)C1-6 alkyl, (C3-8 cycloalkyl)C3-8 alkenyl, or (C1-8 alkylcarbonyl)C1-8 alkyl;
- n is 1 or 2;
- X is O or S;
- one of R2, R3 and R4 is G and the other two independently are hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, methyl, or C1-3alkoxy;
- G is LQ;
- L is unbranched —(CH2)m— wherein m is an integer from 1 to 7;
- Q is NR8R9 wherein R8 is independently selected from hydrogen, C1-6 alkyl, C3-6 alkenyl, 3-9 membered carbocyclyl, 3-12 membered heterocyclyl, phenyl, (6-9-membered heterocyclyl)C1-6 alkylene, and (phenyl)C1-6 alkylene;
- and R9 is independently selected from C1-6 alkyl, C3-6 alkenyl, 6-9 membered carbocyclyl, 3-12 membered heterocyclyl, phenyl, (6-9-membered heterocyclyl)C1-6 alkylene, and (phenyl)C1-6 alkylene;
- or
- Q is a saturated 3-12 membered N-linked heterocyclyl, wherein, in addition to the N-linking nitrogen, the 3-12 membered heterocyclyl may optionally contain between 1 and 3 additional heteroatoms independently selected from O, S, and NH;
- wherein Q is optionally substituted with 1-3 substituents independently selected from the group consisting of hydroxy, halo, carboxamide, C1-6 alkyl, 5-9 membered or 6-9 membered heterocyclyl, —N(C1-6 alkyl)(5-9 membered or 6-9 membered heterocyclyl), —NH(5-9 membered or 6-9 membered heterocyclyl), —O(5-9 or 6-9 membered heterocyclyl), (5-9 membered or 6-9 membered heterocyclyl)C1-3 alkylene, C1-6 alkoxy, (C3-6 cycloalkyl)-O—, phenyl, (phenyl)C1-3 alkylene, and (phenyl)C1-3 alkylene-O—, where each of above heterocyclyl, phenyl, and alkyl groups may be optionally substituted with from 1 to 3 substituents independently selected from trifluoromethyl, methoxy, halo, nitro, cyano, hydroxy, and C1-3 alkyl;
- provided however that when R1 is methyl, G is not piperidin-1-ylmethyl;
- and
- wherein each of the above alkyl, alkylene, alkenyl, heterocyclyl, cycloalkyl, carbocyclyl, and aryl groups may each be independently and optionally substituted with between 1 and 3 substituents independently selected from trifluoromethyl, methoxy, halo, amino, nitro, hydroxy, and C1-3 alkyl;
- or a pharmaceutically acceptable salt, ester, tautomer, solvate or amide thereof.
14 more elements
Dependencies are inferred from the claim text.