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US 2015/0307488 A1Published application
Cyclopropyl imidazopyridine pde10 inhibitors
AssigneeMerck Sharp & Dohme Corp.
InventorsScott D. Kuduk, Douglas C. Beshore, Thomas S. Reger
Life of this patent
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Abstract
The present invention is directed to substituted cyclopropyl imidazopyridine compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.
Claims19
A compound of the formula I:
- wherein:
- R and Rc independently represent H, or C1-6alkyl;
- Rc1 represents H, C1-6alkyl, C1-4haloalkyl, O—R, C(R)2OR, CN, O(CH2)nOR, or OCHR(CH2)nOR;
- Rc2 represents H, C1-6alkyl, C2-6alkenyl, halogen, or CN;
- R2 is selected from the group consisting of H, O—R, CN, O(CH2)nOR, OCHR(CH2)nOR, SR, SO2R, S(O)R, N(R)2, C(O)N(R)2, C1-3 haloalkyl, O(CH2)nC1-3haloalkyl, O(CH2)nC3-6cycloalkyl, (CH2)nC5-10heterocycle, C1-6alkyl, and C3-10cycloalkyl, said alkyl, cycloalkyl and heterocycle unsubstituted or substituted with 1 to 3 groups of Ra;
- Ra is selected from the group consisting of:
- (1) halogen,
- (2) hydroxyl,
- (3) C1-6alkyl,
- (4) —(CH2)nO—R,
- (5) (CH2)nC6-10aryl,
- (6) (CH2)nC5-10 heterocycle,
- (7) OC1-5 haloalkyl;
- (8) CO2R;
- (9) C(O)N(R)2;
- (10) (CH2)nC(O)R;
- (11) CN,
- (12) (CH2)nN(R)2;
- (13) (CH2)nC3-6cycloalkyl,
- (14) (CH2)nC1-3 haloalkyl;
- n represents 0-4,
- or a pharmaceutically acceptable salt thereof.
19 more elements
The compound of formula I represented by structural formula Iaa:
- or a pharmaceutically acceptable salt thereof.
A compound which is:
- 2-((1S,2S)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)imidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-5-methylimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-6-methylimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-7-methylimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-8-methylimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-8-fluoroimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-7-fluoroimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-3-iodoimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-3-methylimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-3-vinylimidazo[1,2-a]pyridine,
- 2-((trans)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)imidazo[1,2-a]pyridine-3-carbonitrile,
- or pharmaceutically acceptable salts thereof.
9 more elements
Dependencies are inferred from the claim text.