Piperidine derivative or pharmaceutically acceptable salt thereof

A derivative and pharmaceutical technology, applied in the field of pharmaceutical compositions, can solve the problem of not mentioning or suggesting sodium channel inhibitory effect or analgesic effect, etc., and achieve excellent sodium channel inhibitory effect, high analgesic effect, and excellent analgesic effect. Effect

Inactive Publication Date: 2007-08-08
ASTELLAS PHARMA INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also, the application of the compounds of Patent Documents 2 and 3 is as a calcium channel antagonist (Patent Document 2) and an acetylcholine release accelerator (Patent Document 3), and in these Patent Documents, there is no mention or suggestion of sodium channel inhibition or sedation. pain effect

Method used

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  • Piperidine derivative or pharmaceutically acceptable salt thereof
  • Piperidine derivative or pharmaceutically acceptable salt thereof
  • Piperidine derivative or pharmaceutically acceptable salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] To 15.0 ml of a N,N-dimethylformamide suspension containing 2.38 g of (2-chlorobenzyl)(triphenyl)phosphonium chloride, 0.63 g of potassium tert-butoxide was added. The mixture was stirred at room temperature for 10 minutes. To the obtained orange suspension, 1.00 g of tert-butyl 4-formylpiperidine-1-carboxylate was added, and the reactant was stirred for 15 minutes to carry out the reaction. The resulting reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with brine, then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate) to give 1.45 g of tert-butyl 4-[2-(2-chlorophenyl)vinyl]piperidine-1-carboxylate in the form of a colorless oil .

Embodiment 2-32

[0092] Compounds shown in Tables 1-3 were obtained in the same manner as in Reference Example 1.

Embodiment 33

[0094] To 1.45 g of tert-butyl 4-[2-(2-chlorophenyl)vinyl]piperidine-1-carboxylate was added 2.10 g of p-toluenesulfonic acid. The mixture was stirred at 150° C. for 5 hours to conduct a reaction. 10.0 ml of water was added to the resulting reaction mixture. The mixture was adjusted to pH about 11 with 10% aqueous sodium hydroxide solution, and extracted with chloroform. The organic layer was washed with water and brine, then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 0.97 g of 4-[(E)-2-(2-chlorophenyl)vinyl]piperidine in the form of a yellow oil.

[0095] (Reference Examples 34-40)

[0096] Compounds shown in Table 3 were obtained in the same manner as in Reference Example 33.

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Abstract

A derivative and salt are excellent in sodium channel inhibitory activity and analgetic activity and have a high analgetic effect especially on neurogenic pains. The piperidine derivative in which the piperidine ring is bonded in the 4-position to a monosubstituted or unsubstituted (-R<1>) benzene ring through vinylene and has an acyl group (-C(=O)-R<4>) in the 1-position; or a pharmaceutically acceptable salt of the derivative. The compounds are useful as a sodium channel inhibitor reduced in side effects.

Description

technical field [0001] The present invention relates to a novel pyridine derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition. More specifically, the present invention relates to a novel pyridine derivative or a pharmaceutically acceptable salt thereof having an excellent sodium channel inhibitory effect and an excellent analgesic effect, and a combination of the above-mentioned pyridine derivative or a pharmaceutically acceptable salt thereof and The pharmaceutical composition with a pharmaceutically acceptable carrier, more specifically relates to a pharmaceutical composition which has analgesic effect on neuropathic pain but has reduced side effects, and can be used as a sodium channel inhibitor. Background technique [0002] Voltage-dependent sodium channels are proteins responsible for initiating and propagating action potentials in neurons. The voltage-dependent sodium channel consists of a larger α subunit and two smaller β subun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/16C07D211/18C07D211/22C07D211/28C07D211/34C07D211/42C07D211/62C07D401/06C07D401/12C07D405/12C07D413/06C07D471/18C07D487/08C07D491/113A61K31/445A61K31/453A61K31/454A61K31/4545A61K31/496A61K31/5377A61K31/55A61K31/553A61K31/438A61K31/439A61P25/00A61P25/04A61P43/00
CPCC07D487/08C07D401/12C07D211/26C07D405/12C07D211/46C07D211/22C07D491/10C07D211/18C07D413/12C07D211/34C07D211/16A61P25/00A61P25/04A61P43/00A61K31/438C07D401/06
Inventor 菊池和美藤安次郎渡边俊博永仓透记富山泰曾根川元治德嵜一夫岩井辰宪
Owner ASTELLAS PHARMA INC
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