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US 2003/0144323 A1Published application
Phenylalkynes
AssigneeOrtho-McNeil Pharmaceutical, Inc.
InventorsRichard Apodaca, Wei Xiao, Jill A. Jablonowski
Life of this patent
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Abstract
Substituted phenylalkynes of formula (I), compositions containing them, and methods of making and using them to treat histamine-mediated conditions.
Claims45
A compound of formula (I)
- 86
- wherein n is an integer from 0 to 1;
- R1 and R2 are independently selected from C1-3 alkyl, allyl, and C3-8 cycloalkyl, or taken together with the nitrogen to which they are attached, they form a non-aromatic 4-7 membered heterocyclyl optionally including up to two additional heteroatoms independently selected from O, S, and N;
- one of R3, R4, and R5 is G, one of the remaining two is hydrogen, and the other is selected from hydrogen, fluoro, and chloro;
- G is L2Q;
- L is methylene;
- Q is NR8R9 wherein R8 is independently selected from hydrogen, C1-6 alkyl, C3-6 alkenyl, 6-9 membered carbocyclyl, 3-12 membered heterocyclyl, phenyl, (5-9-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, (5-9-membered heterocyclyl)C1-6 alkylene, and (phenyl) C1-6 alkylene;
- or
- Q is a saturated 3-13 membered N-linked heterocyclyl, wherein, in addition to the N-linking nitrogen, the 3-13 membered heterocyclyl may optionally contain between 1 and 3 additional heteroatoms independently selected from O, S, and N;
- wherein each of the above alkyl, alkylene, alkenyl, heterocyclyl, cycloalkyl, carbocyclyl, and aryl groups of Formula (I) may each be independently and optionally substituted with between 1 and 3 substituents independently selected from methoxy, halo, amino, nitro, hydroxyl, and C1-3 alkyl;
- and wherein 1-3 substituents of Q can be further independently selected (in addition to the preceding paragraph) from tert-butyloxycarbonyl, carboxamide, Con alkyl, 5-9-membered heterocyclyl, N(C1-6 alkyl)(5-9 membered heterocyclyl), NH(5-9 membered heterocyclyl), O(5-9 membered heterocyclyl), (5-9 membered heterocyclyl)C1-3 alkylene, phenyl, C1-2-hydroxyalkylene, C2-6 alkoxy, (C3-6 cycloalkyl)-O—, phenyl, (phenyl)C1-3 alkylene, and (phenyl)C1-3 alkylene-O— and where said substituent groups of Q may optionally have between 1 and 3 substituents independently selected from trifluoromethyl, halo, nitro, cyano, and hydroxy;
- or a pharmaceutically acceptable salt, ester, or amide thereof.
10 more elements
Dependencies are inferred from the claim text.