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Thienopyrimidine and thienopyridine derivatives substituted with cyclic amino group

A cyclic amino and pyrimidine technology, which can be used in drug combinations, digestive system, endocrine system diseases, etc., and can solve problems such as undisclosed compounds

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

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Problems solved by technology

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

Method used

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  • Thienopyrimidine and thienopyridine derivatives substituted with cyclic amino group
  • Thienopyrimidine and thienopyridine derivatives substituted with cyclic amino group
  • Thienopyrimidine and thienopyridine derivatives substituted with cyclic amino group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0132] Synthesis of {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidine -4-yl}-methanol hydrochloride (compound 1-004)

[0133]

[0134] (1) 7-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2,6-dimethyl-thieno[3,2-d]pyrimidine (500mg), piperidine - A mixture of 4-ylmethanol (226 mg), N,N-diisopropylethylamine (253 mg) in ethanol (1.5 mL) was heated at reflux for 1 day. After the reaction mixture was cooled to room temperature, it was poured into saturated aqueous sodium bicarbonate solution, and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane / EtOAc=3:1) to give {1-[7- (4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol (568 mg).

[0135] (2) Under ice cooling, in {1-[7-(4-bromo-2,6-d...

Embodiment 2

[0138] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidine- 4-yl}-acetic acid

[0139]

[0140] (1) {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]- A mixture of piperidin-4-yl}-acetonitrile (350 mg) and KOH (492 mg) in EtOH (1.5 mL) and water (1.0 mL) was heated in a sealed tube at 105°C for 3 hours. After the reaction mixture was concentrated under reduced pressure, 5% KHSO was added 4 aqueous solution with CHCl 3 extraction. The organic layer was washed with brine and washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was purified by silica gel column chromatography (silica gel: Wako Gel (C200), eluent: CHCl 3 / methanol=20:1) to obtain the title compound (164 mg).

[0141] Table 1 lists the compounds obtained in Example 2 and the compounds obtained according to the similar steps described in Example 2.

Embodiment 3

[0143] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piper Pyridine-4-yl}-acetamide

[0144]

[0145] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidine- 4-yl}-acetonitrile hydrochloride (30mg) was dissolved in CH 2 SO 4 (0.5 mL), and the solution was stirred at room temperature for 20 hours. After adding ice, use NaOH aqueous solution and NaHCO 3 Aqueous solution made the reaction mixture basic (pH 7). The mixture was extracted with EtOAc and the organic layer was washed with brine, washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was purified by silica gel column chromatography (silica gel: Wako Gel (C200), eluent: EtOAc) to obtain the title compound (20 mg) as white crystals.

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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 thienopyrimidine or thienopyridine derivative substituted with a cyclic amino 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04A61P1/00A61P1/04A61P17/00A61P17/14A61P25/02A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/36A61P29/00A61P37/00A61P5/40A61P9/10
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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