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Heteroaryl-substituted urea modulators of fatty acid amide hydrolase

An alkyl and phenyl technology, applied in the field of heteroaryl-substituted urea regulators of fatty acid amide hydrolase, can solve the unknown problems of human osteoporosis

Inactive Publication Date: 2010-03-31
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Genetics plays a considerable role in BMD, but the genetic factors involved in human osteoporosis are largely unknown

Method used

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  • Heteroaryl-substituted urea modulators of fatty acid amide hydrolase
  • Heteroaryl-substituted urea modulators of fatty acid amide hydrolase
  • Heteroaryl-substituted urea modulators of fatty acid amide hydrolase

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0149] Example 1: 4-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid Benzo[d]iso evil Azol-3-ylamide trifluoroacetate

[0150]

[0151] Step A: Benzo[d]iso evil Azol-3-yl-phenylcarbamate Benzo[d]isoxazol-3-ylamide (3.0g) and ClCO 2 Ph (0.94mL) in dry CH 3 The mixture in CN (30 mL) was stirred at 70 °C for 23 hours. The reaction mixture was poured into deionized water, stirred for 30 minutes and filtered. The isolated solid was rinsed thoroughly with water and dried under high vacuum to afford 1.90 g (100%) of the title compound. MS: 255.1.

[0152] Step B: 1-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine Piperazine-1-carboxylate tert-butyl ester (20.0 g) and 2,2-difluoro-benzo[1,3]dioxole-5-carbaldehyde (14.8 mL) in DCE (208 mL) A 0°C solution of NaB(OAc) 3 H (31.8g) treatment. The mixture was allowed to warm to room temperature and stirred for 16 hours. The resulting mixture was cooled in an ice bath and treated with 10% aqu...

example 2

[0155] Example 2: 4-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid (3-Phenyl-[1,2,4]thiadiazol-5-yl)-amide trifluoroacetate

[0156]

[0157] MS: 460.5. 1 H NMR (CDCl 3 ): 10.66 (br s, 1H), 8.10-8.08 (m, 2H), 7.46-7.43 (m, 3H), 7.00 (s, 1H), 6.96 (d, J=8.4, 1H), 6.91-6.89 ( dd, J = 1.2, 7.8, 1H), 3.33 (br s, 6H), 2.15 (br s, 4H).

example 3

[0158] Example 3: 4-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid (1H-tetrazol-5-yl)-amide trifluoroacetate

[0159]

[0160] MS: 368.5. 1 H NMR (d 6 -DMSO): 15.51(s, 1H), 10.98(s, 1H), 7.54(s, 2H), 7.33-7.32(m, 1H), 4.29(br s, 4H), 3.58-2.86(m, 6H) .

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Abstract

Certain heteroaryl-substituted piperidinyl and piperazinyl urea compounds are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods forthe treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity, such as anxiety, pain, inflammation, sleep disorders, eating disorders, insulin resistance, diabetes, osteoporosis, and movement disorders (e.g., multiple sclerosis).

Description

technical field [0001] The present invention relates to certain heteroaryl-substituted piperidinyl urea and piperazinyl urea compounds, pharmaceutical compositions containing them and their use in the treatment of fatty acids mediated by fatty acid amide hydrolase (FAAH) activity methods for disease states, disorders and conditions. Background technique [0002] The medicinal benefits of the cannabis plant have been known for centuries. The main bioactive component of cannabis is Δ 9 - Tetrahydro-cannabinol (THC). The discovery of THC eventually led to the identification of two endocannabinoid receptors responsible for its pharmacological effects, known as CB 1 and CB 2 (Goya, Exp. Opin. Ther. Patents 2000, 10, 1529). These findings not only established THC's site of action, but also inspired the search for endogenous agonists, or "endocannabinoids," of these receptors. The first endocannabinoid identified was the fatty acid amide anandamide (AEA). AEA itself induces ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/497
CPCC07D471/04C07D413/14C07D403/12C07D261/20C07D231/40C07D241/20C07D405/12C07D409/12C07D237/20C07D413/12C07D285/14C07D271/12C07D401/12C07D261/14C07D257/06C07D417/12A61P1/00A61P1/04A61P1/08A61P1/12A61P1/16A61P11/00A61P15/10A61P15/18A61P17/04A61P19/02A61P25/00A61P25/04A61P25/08A61P25/14A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P27/02A61P27/06A61P29/00A61P3/00A61P3/14A61P31/12A61P31/18A61P35/00A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P9/00A61P9/10A61P9/12A61P3/10C07D403/14A61K31/445A61K31/496
Inventor R·阿波达卡J·G·布雷滕布赫尔N·A·豪里卢克W·M·琼斯J·M·基思J·E·梅里特M·S·泰歇诺尔A·K·蒂蒙斯
Owner JANSSEN PHARMA NV
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