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US 6,602,889 B1Granted
5-heteroaryl substituted indoles
AssigneeH. Lundbeck A.S.
InventorsJens Kristian Perregaard, Kim Andersen, Thomas Balle
Life of this patent
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Abstract
The present invention relates to compounds having general formula (I) as defined herein, or a pharmaceutically acceptable acid addition salt thereof. The compounds are selective α1-adrenoceptor ligands.
Claims8
A compound having the formula
- wherein
- Het is selected from the group consisting of pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, tetrazol-1-yl, tetrazol-2-yl, tetrazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-oxadiazol-5-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,2,5-thiadiazol-3-yl, oxatriazol-4-yl, thiatriazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazine-3-yl, pyridazine-4-yl, pyrazine-2-yl, 1,2,3-triazine-4-yl, 1,2,3-triazine-5-yl, 1,2,4-triazine-3-yl, 1,2,4-triazine-5-yl, 1,2,4-triazine-6-yl, 1,3,5-triazine-2-yl and 1,2,4,5-tetrazine-3-yl, and optionally substituted with one or more substituents selected from C1-6-alkyl, C1-6-alkoxy, C1-6alkylthio and hydroxy;
- n is 0, or 1;
- G is N, C, or CH;
- the dotted line meaning a bond when G is C, and the dotted line meaning no bond when G is CH, or N;
- Ar is phenyl optionally substituted with one or more substituents independently selected from halogen, C1-6-alkyl, C1-6-alkoxy, hydroxy, trifluoromethyl and cyano, or Ar is 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 2-thiazolyl, 2-oxazolyl, 2-imidazolyl, 2-pyridyl, 3-pyridyl, or 4-pyridyl;
- R2, R3, R4 and R5 are independently selected from hydrogen, C1-6-alkyl, C1-6-alkoxy, hydroxy, halogen, trifluoromethyl, nitro, cyano, amino, C1-6-alkylamino and C1-6-dialkylamino;
- R6 is hydrogen, C3-8-cycloalkyl, C3-8-cycloalkyl-C1-6-alkyl, C1-6-alkyl, or C1-6-alkenyl, optionally substituted with one or two hydroxy groups, any hydroxy group present being optionally esterified with an aliphatic carboxylic acid having from two to twenty-four carbon atoms inclusive, or R6 is a group of the Formula II or III:
- wherein m is an integer from 2-6;
- W is O, or S;
- U is N or CH;
- Z is —(CH2)p—, p being 2 or 3, or Z is —CH═CH— or 1,2-phenylene optionally substituted with halogen or trifluoromethyl, or Z is —COCH2— or —CSCH2—;
- V is O, S, CH2, or NR9, wherein R9 is hydrogen, C1-6-alkyl or C2-6-alkenyl optionally substituted with one or two hydroxy groups, or a C3-8-cycloalkyl or C3-8-cycloalkyl-C1-6-alkyl group;
- X is N, C, or CH;
- Y is N, C, or CH;
- provided at least one of X and Y is N;
- and R7 is hydrogen, or C1-6-alkyl;
- or a pharmaceutically acceptable acid addition salt thereof.
15 more elements
Dependencies are inferred from the claim text.