2-aminoquinoline derivative

一种氨基喹啉、衍生物的技术，应用在药物组合、杂环化合物有效成分、消化系统等方向，能够解决不容易得出Ar喹啉环等问题

Inactive Publication Date: 2006-06-21
BANYU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, it is not easy to draw from the above description that Ar is a bicyclic aromatic quinoline ring, and the Ar1 part is a combination of phenylpyrimidine ring skeleton

Method used

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Examples

Experimental program
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Effect test

reference example 1

[0238] 1-Methyl-7-(6-nitro-2-quinolyl)-2-oxo-1,7-diazaspiro[4,4]nonane

[0239] (1) Add n-butyllithium (2.6M hexane solution, 32ml) to a solution of diisopropylamine (12ml) in THF (200ml) under ice bath, and stir at the same temperature for 20 minutes. After cooling the solution to -78°C, a THF solution (30 ml) of 1-(tert-butyl) 3-methyl 1,3-pyrrolidinedicarboxylate (13.0 g) was added dropwise, followed by stirring at the same temperature for 1 hour. Next, allyl bromide (10 ml) was added to the reaction solution, and the mixture was stirred at -78°C for 1 hour, and then at room temperature for 1 hour. Saturated ammonium chloride aqueous solution was added to the reaction liquid, extracted with ethyl acetate, the ethyl acetate layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate = 15:1) to obtain 1-(tert-butyl) 3-methyl 3-allyl-1,3-pyrrolidinedicarboxylate in the form o...

reference example 2

[0247] 7-Methyl-2-(6-nitro-2-quinolyl)-8-oxo-2,7-diazaspiro[4,4]nonane

[0248] (1) Cool the mixed solution of 3-pyrrolidinol (4.0g) in dioxane-water (10:1, 50ml) to 5°C, and add 4-nitrobenzyl chloroformic acid dropwise while keeping the pH at 8-9 A solution of the ester (10.9g) in dioxane (20ml). After stirring at 5°C for 10 minutes, the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was dried with ethyl acetate and washed to obtain 3-hydroxy-1(p-nitrobenzyloxycarbonyl)pyrrolidine (6.6 g) as a light yellow solid.

[0249] (2) A solution of the compound obtained in (1) above (6.3 g) and triethylamine (26.5 mg) in DMSO (87 ml) was cooled to 10°C, and pyridinesulfur trioxide complex (11.3 g) was added. After stirring overnight at room temperature, water was added to the reaction solut...

reference example 3

[0263] (3R)-N-Methyl-N-[1-(6-nitro-2-quinolinyl)-3-pyrrolidinyl]isobutyramide

[0264](1) At 0°C, add triethylamine (29.3ml) and di Di-tert-butyl carbonate (34.4 g) was stirred overnight at room temperature. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. A 4N hydrochloric acid-ethyl acetate solution (29.0 ml) was added to the residue, and the resulting white crystals were washed with diisopropyl ether and filtered. The resultant was dried to obtain tert-butyl (3R)-N-(1-benzyl-3-pyrrolidinyl)-N-methylcarbamate hydrochloride (24.2 g) as white crystals.

[0265] ESI-MS Found: m / z 235[M+H]+

[0266] (2) Under a nitrogen atmosphere, 10% palladium carbon (7.2 g) was added to a methanol (225 ml) solution of the compound (22.0 g) obtained in the above (1), and stirred overnight under a hydrogen atmosphere of 1 atm. ...

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PUM

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Abstract

The present invention provides 2-aminoquinoline derivatives, which are represented by the general formula [I] [wherein, R1 and R2 represent lower alkyl groups, lower cycloalkyl groups, or R1 and R2 together form a fatty group with their bonded nitrogen atoms. group of nitrogen-containing heterocyclic rings, R3, R4, R6 and R7 represent hydrogen atoms, lower alkyl groups, etc., R8 represents lower alkyl groups, lower alkoxy groups, etc., and n represents an integer of 0 to 4]. The compound acts as an antagonist of the melanin aggregation hormone receptor, and is useful as a medicine for central diseases, circulatory diseases, and metabolic diseases.

Description

technical field [0001] The present invention relates to 2-aminoquinoline derivatives useful in the field of medicine. This compound acts as a melanin aggregation hormone receptor antagonist, and is useful as a preventive or therapeutic agent for various circulatory system diseases, nervous system diseases, metabolic system diseases, respiratory system diseases, digestive system diseases, and the like. Background technique [0002] Melanin Concentrating Hormone (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 [nature (nature), volume 305, page 321 ( 1983)]. It is known that the functional antagonism of melanocyte-stimulating hormone in fish causes the aggregation of melanin granules in melanocytes and participates in the change of body color [(International Review Of Cytology), volume 126, page 1 (1991); (Trends in Endocrinology...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61K31/506A61K31/55A61P1/00A61P1/16A61P3/04A61P3/06A61P3/10A61P5/00A61P9/00A61P9/04A61P9/10A61P9/12A61P11/00A61P13/12A61P15/00A61P15/06A61P15/08A61P17/00A61P19/06A61P25/00A61P25/02A61P25/08A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P35/00A61P43/00C07D401/14C07D405/12C07D405/14C07D487/04C07D487/10
CPCC07D401/12C07D401/14C07D405/14C07D487/04C07D487/10A61P1/00A61P1/16A61P11/00A61P11/02A61P13/12A61P15/00A61P15/06A61P15/08A61P15/10A61P17/00A61P17/16A61P19/06A61P25/00A61P25/02A61P25/08A61P25/14A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P25/32A61P25/36A61P27/00A61P3/00A61P3/10A61P35/00A61P3/04A61P3/06A61P43/00A61P5/00A61P9/00A61P9/04A61P9/10A61P9/12
Inventor 守谷实铃木隆雄石原安加祢岩浅央金谷章生
Owner BANYU PHARMA CO LTD
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