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Diaryl ketimine derivative

A technology of diaryl ketimines and derivatives, applied in the field of diaryl ketimines derivatives, can solve the problems of no MCH receptor antagonism, no disclosure, etc.

Inactive Publication Date: 2009-08-26
BANYU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this specification does not disclose a compound having a piperidine skeleton and an imine skeleton which is the gist of the present invention.
Moreover, there is no record about MCH receptor antagonism in the specification

Method used

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  • Diaryl ketimine derivative
  • Diaryl ketimine derivative
  • Diaryl ketimine derivative

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0351] Reference example 1 Keto alcohol 10 Synthesis:

reference example 1-1

[0353] Synthesis of 3,4-difluoro-N-methoxy-N-methylbenzamide

[0354] To a chloroform solution (115 mL) of 3,4-difluorobenzoic acid (10.0 g) were added N, O-dimethylhydroxylamine hydrochloride (12.3 g), 1-hydroxybenzotriazole hydrate at 0° C. (14.5g), N-[3-(dimethylamino)propyl]-N'-ethylcarboximide hydrochloride (18.2g) and triethylamine (44.5mL), stirred at room temperature overnight . Water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After the organic layer was concentrated under reduced pressure, the residue was purified by silica gel column chromatography to obtain the title compound (12.8 g) as a colorless oil.

[0355] Mass spectrometer ESI-MS detection: m / z 202[M+H] +

reference example 1-2

[0357] Synthesis of 4-fluoro-N-methoxy-N-methylbenzamide

[0358] Using 4-fluorobenzoic acid (2.00 g), the same procedure as in Reference Example 1-1 was carried out to obtain the title compound (2.09 g) as a colorless oil.

[0359] ESI-MS Found: m / z 184[M+H] +

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PUM

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Abstract

Provided is a compound of a formula (I): [wherein R 1a and R 1b are the same or different, representing a hydrogen atom, etc.; R 2a and R 2b are the same or different, representing a hydrogen atom, etc., or R 2a and R 2b , taken together, form -CH 2 CH 2 -, R 3a and R 3b are the same or different, representing a hydrogen atom, etc.; or R 3a and R 3b , taken together, form - CH 2 CH 2 -etc.; Y 1 and Y 2 represent -C(R) 2 -, etc.; Z represents OR, NR 2 , etc.; R represents a hydrogen atom, a C 1-6 alkyl group, etc.; Ar 1 represents a 6-membered aromatic carbocyclic group, etc.; Ar 2 represents a 6-membered aromatic carbocyclic group, etc; A 3 represents a 6-membered aromatic carbocyclic group etc.]. The compound is useful as a medicine for central disorders, cardiovascular disorders, metabolic disorders.

Description

technical field [0001] The present invention relates to a novel diaryl ketimine derivative. This compound acts as a melanin-concentrating hormone receptor antagonist, and is useful as a preventive or therapeutic agent for various circulatory system diseases, nervous system diseases, metabolic system diseases, reproductive system diseases, respiratory diseases, digestive tract diseases and the like. Background technique [0002] Melanin Concentrating Hormone (hereinafter referred to as "MCH") is a cyclic peptide hormone / neuropeptide isolated for the first time from the pituitary gland of salmon by Kawauchi et al. in 1983 [see Nature, Vol.305, 321 (1983)] . This hormone can functionally antagonize the melanocyte-stimulating hormone contained in fish, cause the concentration of melanin granules in melanocytes, and participate in causing body color changes [refer to International Review of Cytology, Vol.126, 1 (1991); Trends in Endocrinology and Metabolism, Vol. 5, 120 (1994)]...

Claims

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Application Information

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IPC IPC(8): C07D491/20A61K31/438A61K31/444A61K31/497A61K31/506A61P5/00A61P9/04A61P9/10A61P9/12A61P11/00A61P1/00A61P13/12A61P1/16A61P15/06A61P3/04A61P15/10A61P3/06A61P17/00A61P3/10A61P19/06A61P25/02A61P25/28A61P25/08A61P25/32A61P25/14A61P25/36A61P25/18A61P35/00A61P25/22A61P43/00A61P25/24
Inventor 铃木隆雄安东诚宫副博龟田稔关野江都子守谷实
Owner BANYU PHARMA CO LTD
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