Cyclic amine-1-carboxylic acid ester derivative and pharmaceutical composition containing the same

一种甲酸酯、化合物的技术，应用在环状胺-1-甲酸酯衍生物及含有其的药物组合物领域，能够解决刺激痛强等问题

Inactive Publication Date: 2011-06-08
SUMITOMO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this cream has the problem of strong initial irritation

Method used

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  • Cyclic amine-1-carboxylic acid ester derivative and pharmaceutical composition containing the same
  • Cyclic amine-1-carboxylic acid ester derivative and pharmaceutical composition containing the same
  • Cyclic amine-1-carboxylic acid ester derivative and pharmaceutical composition containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0240] Preparation of cis-4-ethylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate:

[0241] 【Chemical 9】

[0242]

[0243] (1) In 4-benzyloxy-3-methoxybenzylamine hydrochloride (14.0g), 1-(tert-butoxycarbonyl)-piperidine-4-carboxylic acid (11.5g), triethyl To a mixture of amine (14.0ml) and dichloromethane (300ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (12.5g). The reaction solution was stirred at room temperature for 20 hours, washed successively with saturated ammonium chloride aqueous solution and saturated brine, and the organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane / ethyl acetate = gradient from 100 / 0 to 0 / 100) to obtain 4-(4-benzyloxy-3-methoxybenzylamino Formyl)-piperidine-1-carboxylic acid tert-butyl ester 16.3 g.

[0244] (2) The product (16.3 g) of the above (1) was...

Embodiment 2～12

[0250] Various substituted cyclohexanols were used instead of cis-4-ethylcyclohexanol in Example 1, and the same reaction and treatment as in Example 1 were carried out to obtain the compounds shown in Table 1 and Table 2.

[0251]

[0252]

Embodiment 13

[0254] Preparation of cis-2-ethylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate:

[0255] 【chemical 10】

[0256]

[0257] Replace the cis-4-ethylcyclohexanol in Example 1 with 2-Ethylcyclohexanol, and carry out the same reaction and treatment as in Example 1. Then, the resulting cis compound was separated by silica gel column chromatography (eluting solvent: hexane / ethyl acetate = gradient from 100 / 0 to 0 / 100) to obtain the desired product.

[0258]

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PUM

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Abstract

Disclosed is a compound useful as a therapeutic agent for pain or inflammation induced by various disease conditions including neurogenic pain and rheumatoid arthritis. Specifically disclosed is a compound represented by formula (I) or a salt thereof [in the formula, R1 represents a methyl group or a hydrogen atom; R2 represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an arylcarbonyl group; A represents a cycloalkyl group, a cycloalkenyl group, an aryl group or a heteroaryl group (each of these groups may be substituted by a substituent selected from the group consisting of an alkyl, an alkenyl, a cycloalkyl and a halogen); n and m independently represent an integer of 1, 2, or 3; and p represents an integer of 0, 1, 2 or 3].

Description

technical field [0001] The present invention relates to cyclic amine-1-carboxylate derivatives useful as therapeutic drugs for pain and inflammation, and in particular, to cyclic amine-1 having a 3,4-disubstituted benzylcarbamoyl group on the ring -Formate derivatives and pharmaceutical compositions containing them. Background technique [0002] Currently, as analgesics, narcotic analgesics such as morphine and non-narcotic analgesics such as NSAIDs (Non-Steroidal Anti-Inflammatory Drugs) are mainly used. However, the use of narcotic analgesics is strictly limited due to the development of tolerance, dependence, or other serious side effects. In addition, NSAIDs are ineffective against severe pain, and there are problems such as high frequency of upper gastrointestinal disorders or liver disorders after long-term administration. Therefore, an analgesic with higher analgesic effect and fewer side effects is highly desired. Furthermore, for neuropathic pain such as diabetic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D205/04A61K31/397A61K31/40A61K31/445A61P1/04A61P3/04A61P3/10A61P9/00A61P11/00A61P11/02A61P11/06A61P11/08A61P13/10A61P17/00A61P17/04A61P19/02A61P25/04A61P25/06A61P29/00A61P37/08C07D207/16C07D211/62
CPCC07D205/04A61P1/02A61P1/04A61P11/00A61P11/02A61P11/06A61P11/08A61P13/10A61P17/00A61P17/04A61P19/02A61P19/08A61P23/00A61P23/02A61P25/00A61P25/02A61P25/04A61P25/06A61P25/08A61P25/22A61P25/24A61P29/00A61P3/04A61P37/08A61P43/00A61P9/00A61P9/06A61P9/10A61P3/10
Inventor 筑木保知森江俊哉中村高典志水勇夫宫内政德
Owner SUMITOMO PHARMA CO LTD
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