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Fluorinated compounds

A compound, the technology of difluoromethoxy, applied in the field of fluorine-containing compounds

Inactive Publication Date: 2013-02-13
NPS PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, any attempt to block this demethylation pathway may improve overall clinical outcomes

Method used

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  • Fluorinated compounds
  • Fluorinated compounds
  • Fluorinated compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0123] Example 1.1 : Methyl 2-(Benzhydrylamino)-3-Hydroxypropionate

[0124]

[0125] Methylserine hydrochloride (15 g, 0.096 mol) was stirred with potassium carbonate (66.6 g, 0.482 mol) and benzyl bromide (41.2 g, 0.24 mol) in acetonitrile (240 mL) for 24 hours at room temperature. The reaction mixture was filtered and washed with ethyl acetate. The filtrate was concentrated with silica gel. The product was purified by column chromatography, eluting with 5-20% ethyl acetate in hexanes, to yield methyl 2-(benzhydrylamino)-3-hydroxypropanoate (27 g , 93.5%). 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 7.25-7.40 (m, 10H), 3.94 (d, 2H), 3.83 (s, 3H), 3.79 (m, 2H), 3.71 (d, 2H), 3.60 (t, 1H) and 2.62(t, 1H).

Embodiment 21

[0126] Example 2.1 : Methyl 2-benzhydrylamino-3-difluoromethoxypropionate

[0127]

[0128] To a solution of methyl 2-(benzhydrylamino)-3-hydroxypropionate (23 g, 76.8 mmol) and sodium sulfate (3.9 g, 27.4 mmol) in acetonitrile at 40°C was added dropwise over 1.5 hours. Fluoro(fluorosulfonyl)acetic acid (25 g, 140 mmol). The reaction mixture was concentrated to dryness, and the residue was combined with silica gel in ethyl acetate and concentrated to dryness again. The product was purified by column chromatography eluting with 3-4% acetic acid in hexane to give methyl 2-benzhydrylamino-3-difluoromethoxypropionate (1.3 g, 4.8 %). 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 7.20-7.40 (m, 10H), 6.18 (bt, 1H), 4.05-4.24 (m, 2H), 3.90 (d, 2H), 3.83 (s, 3H) and 3.64-3.71 (m , 3H).

Embodiment 31

[0129] Example 3.1 : 2-(Benzhydrylamino)-3-(difluoromethoxy)propionic acid

[0130]

[0131] At 50°C, methyl 2-benzhydrylamino-3-difluoromethoxypropionate (1.2 g, 3.43 mmol) and 1N LiOH (10.3 mL, 10.3 mmol) were stirred in THF solution (40 mL) for 2 hours, then stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and acidified with 1N HCl. The organic layer was dried over sodium sulfate and concentrated over silica gel. The product was purified by column chromatography eluting with 10-50% ethyl acetate in hexanes to yield 2-(benzhydrylamino)-3-(difluoromethoxy)propanoic acid (730 mg , 63.5%). 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 7.26-7.42 (m, 10H), 6.29 (bt, 1H), 4.45 (dd, 1H), 4.28 (dd, 1H), 3.94 (q, 4H) and 3.85 (m, 1H).

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Abstract

Compounds of Formula I are useful in the treatment of epilepsy, neuropathic pain, acute and chronic inflammatory pain, migraine, tardive dyskinesia and other related CNS disorders. wherein: A and R1 to R8 are defined in the specification.

Description

technical field [0001] The present invention relates to a novel amino acid derivative, a preparation method thereof, a pharmaceutical composition containing the amino acid derivative, and their use in the treatment of epilepsy, neuropathic pain, acute and chronic inflammatory pain, migraine, and tardive dyskinesia and other related CNS disorders. Background technique [0002] Epilepsy is a common neurological disorder characterized by recurrent spontaneous seizures and is considered a major health problem affecting approximately 1% to 2% of the world's population [Brown et al. N..Engl.J.Med. , 2001, 344, 1145-1151.]. Epilepsy also imposes a considerable economic burden on society. The direct costs of epilepsy vary significantly according to the severity of the disease and the response to treatment. Despite considerable progress in the understanding of epilepsy and seizure pathophysiology and pharmacotherapy [McNamara Nature, 1999, 399, A15-A22.], the cellular basis of hum...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/20C07C271/22C07C237/06C07C311/06A61K31/165A61K31/18
CPCC07C311/06C07D233/20C07C237/22C07C271/22A61P25/00A61P25/04A61P25/06A61P29/00
Inventor G·A·希金斯M·伊萨科A·斯莱斯T·辛
Owner NPS PHARM INC
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