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US 2006/0142364 A1Published application
Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
AssigneeAstraZeneca AB
InventorsDaniel Page, Christopher Walpole, Hua Yang
Life of this patent
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Abstract
Compounds of formula (I) or pharmaceutically acceptable salts thereof: Formula (I) wherein R1, R2, RF1, RF2 and Z are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
Claims12
A compound of formula I or a pharmaceutically acceptable salt thereof:
- wherein
- RF1 and RF2 are independently C1-6alkyl substituted by one or more groups selected from —F, —Cl, —Br, —NO2, —CN, —OH, —CHO, —C(═O)—R′ and —OR′, wherein R′ is a C1-3alkyl;
- Z is selected from O═ and S═;
- R1 is selected from C1-10alkyl, C2-10alkenyl, C2-10alkynyl, R3R4N—C1-6alkyl, R3O—C1-6alkyl, R3C(═O)N(—R4)—C1-6alkyl, R3R4NS(═O)2—C1-6alkyl, R3CS(═O)2N(—R4)—C1-6alkyl, R3R4NC(═O)N(—R5)—C1-6alkyl, R3R4NS(═O)2N(R5)—C1-6alkyl, C6-10aryl-C6-10alkyl, C6-10aryl-C(═O)—C1-6alkyl, C3-10cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocyclyl-C1-6alkyl, C3-6heterocyclyl-C(═O)—C1-6alkyl, R3R4N—, R3O—, R3C(═O)N(—R4)—, R3R4NS(═O)2—, R3CS(═O)2N(—R4)—, R3R4NC(═O)N(—R5)—, R3R4NS(═O)2N(R5)—, C6-10aryl, C6-10aryl-C(═O)—, C3-10cycloalkyl, C4-8cycloalkenyl, C3-6heterocyclyl and C3-6heterocyclyl-C(═O)—;
- wherein said C1-10alkyl, C2-10alkenyl, C2-10alkynyl, C6-10aryl-C1-6alkyl, C6-10aryl-C(═O)—C1-6alkyl, C3-10cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocyclyl-C1-6alkyl, C3-6heterocyclyl-C(═O)—C1-6alkyl, C1-10hydrocarbylamino, C6-10aryl, C6-10aryl-C(═O)—, C3-10cycloalkyl, C4-8cycloalkenyl, C3-6heterocyclyl or C3-6heterocyclyl-C(═O)— used in defining R1 is optionally substituted by one or more groups selected from halogen, cyano, nitro, methoxy, ethoxy, methyl, ethyl, hydroxy, and R3R4N—;
- R2 is selected from the group consisting of C1-10alkyl, C2-10alkenyl, C2-10alkynyl, C3-10cycloalkyl, C3-10cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocycloalkyl-C1-6alkyl, C4-8cycloalkenyl, R3R4N—, C3-5heteroaryl, C6-10aryl and C3-6heterocycloalkyl, wherein said C1-10alkyl, C2-10alkenyl, C2-10alkynyl, C3-10cycloalkyl, C3-10cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocycloalkyl-C1-6alkyl, C4-8cycloalkenyl, C3-5heteroaryl, C6-10aryl or C3-6heterocycloalkyl used in defining R2 is optionally substituted by one or more groups selected from halogen, cyano, nitro, methoxy, ethoxy, methyl, ethyl, hydroxy and R3R4N—;
- and
- R3 and R4 and are independently selected from —H, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and a divalent C1-6 group that together with another divalent C1-6group selected from R3 and R4 forms a portion of a ring.
5 more elements
A compound selected from 2-tert-Butyl-1-(cyclohexylmethyl)-N,N-bis(2,2,2-trifluoroethyl)-1H-benzimidazole-5 -carboxamide and pharmaceutically acceptable salts thereof.
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A method for preparing a compound of formula I,
- comprising the step of reacting a compound of formula II,
- with a compound of R2C(═O)—X to form the compound of formula I, wherein
- RF1 and RF2 are independently selected from —CF3, —CH2CF3, —CH2CHF2, —CHFCF3, —CHFCHF2, —CHFCH2F, —CF2CF3, —CF2CH3, —CF2CH2F, —CF2CHF2, and —CF3;
- Z is selected from O═ and S═;
- X is selected from —Cl, —Br, —I, —OH, —OCH3, and —OCH2CH3;
- R1 is selected from C1-6alkyl, C2-6alkenyl, R3R4N—C1-4alkyl, R3O—C1-4alkyl, R3C(═O)N(—R4)—C1-4alkyl, phenyl-C1-4alkyl, phenyl-C(═O)—C1-4alkyl, C3-10cycloalkyl-C1-4alkyl, C4-6cycloalkenyl-C1-4alkyl, C3-6heterocyclyl-C1-4alkyl, C3-6heterocycly-C(═O)—C1-4alkyl, phenyl, C3-10cycloalkyl, C3-6heterocyclyl and C3-6heterocyclyl-C(═O)—;
- wherein said C1-6alkyl, C2-6alkenyl, R3R4N—C1-4alkyl, R3O—C1-4alkyl, R3C(═O)N(—R4)—C1-4alkyl, phenyl-C1-4alkyl, phenyl-C(═O)—C1-4alkyl, C3-10cycloalkyl-C1-4alkyl, C4-6cycloalkenyl-C1-4alkyl, C3-6heterocyclyl-C1-4alkyl, C3-6heterocycly-C(═O)—C1-4alkyl, phenyl, C3-10cycloalkyl, C3-6heterocyclyl or C3-6heterocyclyl-C(═O)— used in defining R1 is optionally substituted by one or more groups selected from halogen, cyano, nitro, methoxy, ethoxy, methyl, ethyl, hydroxy, and R3R4N—;
- R2 is selected from the group consisting of C1-6alkyl, C3-6cycloalkyl, R3R4N—, C3-6cycloalkyl-C1-4alkyl, C3-6heterocycloalkyl-C1-4alkyl, C3-6heterocycloalkyl, C3-5heteroaryl, and phenyl wherein said C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C3-6heterocycloalkyl-C1-4alkyl, C3-6heterocycloalkyl, C3-5heteroaryl, and phenyl used in defining R2 is optionally substituted by one or more groups selected from halogen, cyano, nitro, methoxy, ethoxy, methyl, ethyl, hydroxy and amino;
- and
- R3 and R4 are independently selected from —H, C1-6alkyl and C2-6alkenyl.
7 more elements
Dependencies are inferred from the claim text.