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7-phenylpyrazolopyridine compounds

A compound, methyl technology, applied in the field of 7-phenylpyrazolopyridine compounds

Inactive Publication Date: 2007-09-19
EISIA R&D MANAGEMENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] However, none of the compounds described in these literatures is mentioned as having CRF receptor antagonistic, anxiolytic or antidepressant properties

Method used

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Examples

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Embodiment

[0236] The following Preparation Examples, Examples and Test Examples are used for illustration only and do not impose any limitation on the compounds of the present invention. It is obvious to those skilled in the art that various modifications can be made to these examples within the scope of the claims of the present invention to maximize the effect of the present invention, and these modifications are also included in the scope of the claims.

[0237] The idiom "purify by silica gel column chromatography and obtain the title compound from fractions" in this specification means that the fraction containing the target compound obtained by silica gel column chromatography is concentrated and further recrystallized if necessary Purification affords the title compound.

preparation Embodiment 1

[0239] 2-(1-butynyl)pyridine

[0240]

[0241] Add dichlorobis(triphenylphosphine)palladium(II) (2.2g) and cuprous iodide (0.3g) in the solution that 2-bromopyridine (50g) is dissolved in diethylamine (500mL), reaction mixture is in Stir at room temperature for 4 hours while introducing gaseous 1-butyne (100 g). The resulting reaction mixture was bubbled with nitrogen, then ethyl acetate was added. The reaction mixture was filtered through celite to remove insoluble residue, and the filtrate was washed with water and brine. The organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (35 g) as a brown oil from n-hexane:ethyl acetate (5:1) fractions .

[0242] 1 H NMR (400MHz, CDCl 3 )δ1.26(t, J=7.6Hz, 3H), 2.45(q, J=7.6Hz, 2H), 7.16-7.20(m, 1H), 7.35-7.38(m, 1H), 7.59-7.63(m , 1H), 8.53-8.54(m, 1H).

preparation Embodiment 2

[0244] 2-Ethylpyrazolo[1,5-a]pyridine

[0245]

[0246] To a solution of 2-(1-butynyl)pyridine (12.8 g) dissolved in dichloromethane (60 mL) was added O-mesitylenesulfonyl hydroxylamine (reference: Synthesis, 1997, 1) (20 g) solution in dichloromethane (132 mL) while cooling with ice, and the reaction mixture was stirred for 30 minutes. Diethyl ether (2 L) was added to the reaction mixture to precipitate crystals, which were filtered and dried under reduced pressure to give crude N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate (12.6 g) as a colorless crystals.

[0247] 6.1 g of crude N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate was dissolved in tetrahydrofuran (600 mL), potassium tert-butoxide (3.55 g) was added at room temperature, and the reaction mixture was vigorously stirred for 30 minutes . Then ice water was added and extracted with ethyl acetate. After extracting the aqueous phase twice with ethyl acetate, the insoluble residue was filtered with diato...

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Abstract

A compound represented by the following general formula, its salt or hydrates thereof: (I) wherein R<1> represents methoxy, methyltio, ethyl, etc.; R<5> and R<6> independently represent each cyclopropylmethyl, (4-tetrahydropyranyl)methyl, etc.; and two of R<40>, R<41> and R<42> are C1-6 alkoxy while the remainder is methoxymethyl, etc. The above compound has an excellent antagonism to a corticotropin-releasing factor receptor.

Description

technical field [0001] The present invention relates to a new class of compound with adrenocorticotropic hormone releasing factor receptor antagonistic activity, its salt and its hydrate, its production method and its use as medicine. Background technique [0002] Corticotropin-releasing factor (hereinafter referred to as "CRF") is a neuropeptide containing 41 amino acids originally obtained from the hypothalamus of sheep [Science, 213 , 1394(1981)], and then its existence was found in rats [Proc.Natl.Acad.Sci.USA, 80 , 4851(1983)] and [EMBO J.5, 775(1983)] were verified. CRF is most abundant in the pituitary gland and hypothalamus, and is widely distributed in the cerebral cortex, cerebellum, and other parts of the brain. Its presence has also been demonstrated in peripheral tissues such as the placenta, adrenal gland, lung, liver, pancreas, and gastrointestinal tract [Exp.Clin.Endocrinol.Diabetes, 105 , 65 (1997)]. Two CRF receptor subtypes have been described: CRF1 an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61K31/4545A61K31/5377A61K31/695A61P1/00A61P1/04A61P1/08A61P1/10A61P1/12A61P5/38A61P25/00A61P25/18A61P25/20A61P25/22A61P25/24C07F7/18C07F5/02
CPCC07F5/025C07F7/1848C07D471/04A61P1/00A61P1/04A61P1/08A61P1/10A61P1/12A61P1/14A61P5/38A61P25/00A61P25/18A61P25/20A61P25/22A61P25/24C07F7/1804
Inventor 日比滋树星野伟久菊池浩一慎光玉高桥良典藤泽正枝柴田寿伊野充洋
Owner EISIA R&D MANAGEMENT CO LTD
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