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Pyrrolopyrimidine and pyrrolotriazine derivatives as CRF receptor antagon

A technology of triazine derivatives and pyrrolopyrimidines, applied in anti-inflammatory agents, drug combinations, non-central analgesics, etc., can solve the problems of undisclosed compounds

Inactive Publication Date: 2007-02-07
TAISHO PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compounds provided by the present invention are not disclosed

Method used

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  • Pyrrolopyrimidine and pyrrolotriazine derivatives as CRF receptor antagon
  • Pyrrolopyrimidine and pyrrolotriazine derivatives as CRF receptor antagon
  • Pyrrolopyrimidine and pyrrolotriazine derivatives as CRF receptor antagon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Synthesis of 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-(1-propyl-butylamino)-pyrrole[1,2-α]pyrimidine-6- Carboxylic acid amide hydrochloride (compound 1-001)

[0080]

[0081] (1) 8-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2-methyl-pyrrole[1,2-α]pyrimidine-6-carbonitrile (30.0g), A mixture of 1-propyl-butylamine (18.5 g), N,N-diisopropylethylamine (15.5 g) in ethanol (90 mL) was heated at reflux for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into saturated aqueous sodium bicarbonate solution, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a solid. The solid was washed with diisopropyl ether to give 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-(1-propyl-butylamino)- Pyrrole[1,2-α]pyrimidine-6-carbonitrile (27.0 g).

[0082]

[0083] (2) 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-(1...

Embodiment 2

[0087] Synthesis of 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-(N,N-dipropylamino)-pyrrole[1,2-α]pyrimidine-6- Carboxylic acid amide (compound 1-022)

[0088]

[0089] (1) 8-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2-methyl-pyrrole[1,2-α]pyrimidine-6-carbonitrile (7.50g), A mixture of thiourea (7.11 g) in ethanol (50 mL) was heated at reflux for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into 0.5M NaOH aqueous solution, stirred for 1 hour, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform / methanol=10:1), thereby obtaining 8-(4-bromo-2 , 6-Dimethyl-phenyl)-4-mercapto-2-methyl-pyrrole[1,2-α]pyrimidine-6-carbonitrile (7.52 g).

[0090]

[0091] (2) 8-(4-bromo-2,6-dimethyl-phenyl)-4-mercapto-2-me...

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Abstract

An object of the present invention is to provide an antagonist against CRF receptors which is effective as a therapeutic or prophylactic agent for diseases in which CRF is considered to be involved, such as depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastral diseases, drug dependence, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, cephalic external wound, inflammation, immunity-related diseases, alpecia, irritable bowel syndrome, sleep disorders, dermatitides, schizophrenia, pain, etc. A pyrrolopyrimidine or pyrrolotriazine derivative substituted with a carbamoyl group represented by the following formula [I]: has a high affinity for CRF receptors and is effective against diseases in which CRF is considered to be involved.

Description

technical field [0001] The present invention relates to a therapeutic agent for diseases believed to be associated with corticotropin releasing factor (CRF), such as depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's disease, Eating diseases, hypertension, gastrointestinal diseases, drug dependence, cerebral infarction, cerebral ischemia, cerebral edema, traumatic brain injury, inflammation, immune-related diseases, alopecia (alpecia), irritable bowel syndrome, sleep disorders, epilepsy , dermatitis, schizophrenia, pain, etc. Background technique [0002] CRF is a hormone containing 41 amino acids (Science, 213, 1394-1397, 1981; and J. Neurosci., 7, 88-100, 1987), and it is believed that CRF plays a central role in the biological response against stress ( Cell. Mol. Neurobiol., 14, 579-588, 1994; Endocrinol., 132, 723-728, 1994; and Neuroendocrinol. 61, 445-452, 1995). For CRF, there are two pathways: the pathway by which CRF acts on the peripheral...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/53A61K31/519
CPCC07D487/04A61P1/00A61P17/00A61P17/14A61P25/00A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P29/00A61P37/02A61P43/00A61P9/10A61P9/12
Inventor 中里笃郎大久保武利野泽大民田智子L·E·J·肯尼斯
Owner TAISHO PHARMACEUTICAL CO LTD
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