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Tricycle compounds and its application in making medicine

A compound, benzene ring technology, used in organic chemistry, drug combinations, pharmaceutical formulations, etc.

Inactive Publication Date: 2007-04-18
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Our use of a D3 partial agonist to treat withdrawal-induced compulsive behaviors in morphine-addicted mice is highly effective, strongly suggesting that this new class of drug may control the addiction-driven compulsive seeking in heroin addicts drug behavior

Method used

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  • Tricycle compounds and its application in making medicine
  • Tricycle compounds and its application in making medicine
  • Tricycle compounds and its application in making medicine

Examples

Experimental program
Comparison scheme
Effect test

preparation example IV

[0128] Preparation IV: 4-((±)trans-3,4,4a,10b-tetrahydro-9-methoxy-2H,5H-[1]-benzopyran-[4,3-b] And-1,4-oxazin-yl)butyl-1-amine (70-1) and 4-((±)cis-3,4,4a,10b-tetrahydro-9-methoxy-2H , 5H-[1]-benzopyran-[4,3-b]-1,4-oxazin-yl)butyl-1-amine (71-1)

[0129]

[0130] Replace phenol (53) with p-methoxyphenol (53-1), and operate with the above-mentioned sequential experimental steps to prepare 4-((±)trans-3,4,4a,10b-tetrahydro-9-methoxy -2H, 5H-[1]-benzopyran-[4,3-b]-1,4-oxazin-yl)butyl-1-amine (70-1) and 4-((±) cis-3,4,4a,10b-tetrahydro-9-methoxy-2H,5H-[1]-benzopyran-[4,3-b]o-1,4-oxazin-yl ) Butyl-1-amine (71-1).

[0131] Preparation IV: 4-((±)trans-3,4,4a,10b-tetrahydro-2H,5H-[1]-benzothiopyran-[4,3-b]a-1, 4-oxazin-yl)butyl-1-amine (70-2) and 4-((±)cis-3,4,4a,10b-tetrahydro-2H,5H-[1]-benzothio Substituted pyran-[4,3-b]-1,4-oxazin-yl)butyl-1-amine (71-2)

[0132]Using thiophenol (53-2) instead of phenol (53), follow the above-mentioned sequential experimental steps to pre...

Embodiment 1

[0133] Example 1: N-[4-((±)trans-3,4,4a,10b-tetrahydro-2H,5H-[1]-benzopyran-[4,3-b]-1 , 4-oxazin-yl) butyl]-1-naphthylcarboxamide (I a-4)

[0134]

[0135] Get compound (70) 0.52g to dissolve with 20ml chloroform, add K 2 CO 3 2g and 2g of naphthoyl chloride were dissolved in an appropriate amount of chloroform, added dropwise with a constant pressure dropping funnel, after the dropwise addition, suction filtered, the mother liquor was concentrated under reduced pressure, and separated by column chromatography to obtain 0.67g of a white solid, with a yield of 82.3% , mp161-162°C.

[0136] IR(KBr):v 3265, 2947, 2866, 2806, 1632, 1583, 1456, 1302, 1128, 1080, 989, 932, 787, 762, 717cm -1 ; 13 C-NMR (CDCl 3 , 300MHz), δ(ppm): 23.6, 23.8, 27.8, 39.8, 52.1, 53.2, 59.6, 65.8, 67.0, 75.3, 115.6, 120.7, 122.0, 124.7, 124.8, 125.3, 125.4, 126.4, 127.1, 128.7, 128 , 130.1, 130.5, 133.7, 134.9, 153.1, 169.6; ESI-MS m / z: 417.2 [M+H] + ;Anal.calcd for C 26 h 28 N 2 o 3 (%): ...

Embodiment 2

[0137] Example 2: N-[4-((±)trans-3,4,4a,10b-tetrahydro-2H,5H-[1]-benzopyran-[4,3-b]-1 , 4-oxazin-yl)butyl]-4-chlorobenzamide (I a-1)

[0138] The specific experimental operation was the same as in Example 1, and chlorobenzoyl chloride was used instead of naphthoyl chloride to obtain 0.65 g of white solid (I a-1), yield 80.5%, mp 124-125°C.

[0139] Data for I a-1: IR (KBr): v 3302, 3072, 2970, 2864, 2812, 1632, 1587, 1541, 1302, 1230, 1128, 986, 841, 746cm -1 ; 1 H-NMR (CDCl 3 , 300MHz), δ (ppm): 1.60-1.70 (m, 4H, -N-CH 2 -CH 2 -CH 2 -CH 2 -NH-), 2.33-2.46(m, 2H, one of -N-CH 2 -CH 2 -CH 2 -CH 2 -NH- and one of-N-CH 2 -CH 2 -O-), 2.50-2.55(m, 1H, Ar-CH-CH-N-), 2.79-2.81(m, 1H, -N-CH 2 -CH 2 -CH 2 -CH 2 -NH-), 2.92(d, 1H, J=11.78Hz, -N-CH 2 -CH 2 -O-), 3.48(q, 2H, J=6.35Hz, -CONH-CH 2 -), 3.87-3.94 (m, 2H, one of -O-CH 2 -CH 2 -N- and one of Ar-O-CH 2 -), 4.05-4.10 (m, 1H, -O-CH 2 -CH 2 -N-), 4.43(d, 1H, J=8.96Hz, Ar-CH-), 4.51(dd, 1H, J=3.66Hz and 10.78...

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Abstract

The present invention relates to a tricyclic compound or its stereo-isomer or its pharmaceutically-acceptable salt and their application in preparation of medicine for curing the disease of central nervous system. Besides, said invention also provides the chemical general formula of said tricyclic compound and its detailed description.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and relates to a dopamine D3 receptor partial agonist, namely a tricyclic compound, and its application in pharmacy. Background technique [0002] The dopamine receptor subtype belongs to the G protein-coupled receptor family with 7 transmembrane domains. Seeman in 1988 divided the dopamine receptor subtypes into two families according to the difference in sequence and signal transduction coupling: D 1 dopamine-like receptors including D 1 and D 5 Receptor; D 2 dopamine-like receptors including D 2 ,D 3 and D 4 receptor. D. 2 The receptor is the main binding target of traditional antipsychotic drugs, but can cause extrapyramidal side effects. D. 3 Receptors are mainly concentrated in dopamine neural pathways in the limbic system of the brain, which is associated with emotional and cognitive functions. In the nerve structure of the limbic system, there are endogenous enkephalins and end...

Claims

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Application Information

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IPC IPC(8): C07D498/04A61K31/542A61P25/00A61P25/30A61P25/16A61P25/18
Inventor 吉民戴德哉蔡进戴茵华维一贾楠李铭东顾莉洁
Owner SOUTHEAST UNIV
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