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Process for the preparation of substituted phenylalanines

A phenyl and hydrocarbon group technology, applied in the field of compound synthesis, can solve problems such as side effects

Inactive Publication Date: 2011-09-28
LEXICON PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Because serotonin is involved in so many biochemical processes, drugs that affect serotonin levels are often accompanied by side effects

Method used

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  • Process for the preparation of substituted phenylalanines
  • Process for the preparation of substituted phenylalanines
  • Process for the preparation of substituted phenylalanines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0092] One embodiment of the invention comprises deprotecting a compound of formula I(a) to provide a compound of formula I:

[0093]

[0094] where: R 1 is hydrogen or an optionally substituted hydrocarbyl, hydrocarbyl-aryl, hydrocarbyl-heterocycle, aryl or heterocycle. In a specific embodiment, the compound of formula I is represented by formula I(b):

[0095]

[0096] where: each R 11 are independently hydrogen, cyano, nitro, halogen, OR 8 、NR 9 R 10 , or an optionally substituted hydrocarbyl, hydrocarbyl-aryl or hydrocarbyl-heterocycle; each R 12 are independently hydrogen, cyano, nitro, halogen, OR 8 、NR 9 R 10 , or an optionally substituted hydrocarbyl, hydrocarbyl-aryl or hydrocarbyl-heterocycle; m is 1-5; and p is 1-4.

[0097] In one embodiment, the compound of formula I(b) is represented by formula I(c), I(d) or I(e):

[0098]

[0099] Certain embodiments of the present invention can be understood with reference to Scheme 1:

[0100]

[0101] R...

Embodiment

[0126] The following non-limiting examples describe (S)-2-amino-3-(4-(2-amino-6-((R)-2,2,2-trifluoro-1-(3'-methanol Synthesis of oxybiphenyl-4-yl)ethoxy)pyrimidin-4-yl)phenyl)-propionic acid.

[0127] Generally, intermediate compounds 3 and 8 are first prepared as shown in Reaction Schemes 3(a) and 3(b) below.

[0128]

[0129] Scheme 3(a)

[0130]

[0131] Scheme 3(b)

[0132] An alternative synthesis of compound 8 is shown in Scheme 3(c):

[0133]

[0134] Scheme 3(c)

[0135] The intermediate is then coupled as shown in Scheme 3(d) below:

[0136]

[0137] Scheme 3(d)

[0138] In the following examples, the yields of various reactions are reported on a molar basis. Reagents are commercially available and can be purchased from Sigma-Aldrich Company, Inc. (Milwaukee, WI, USA) unless otherwise noted.

[0139] Preparation of (R)-1-(4-bromophenyl)-2,2,2-trifluoroethanol (2)

[0140]

[0141] This compound was prepared based on literature procedures (Ohkuma...

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Abstract

Intermediates and synthetic processes for the preparation of substituted phenylalanine-based compounds (e.g., of Formula I) are disclosed:

Description

technical field [0001] The present invention relates to synthetic methods for the preparation of substituted phenylalanine based compounds. Background technique [0002] The neurotransmitter [5-hydroxytryptamine (5-HT)] is involved in multiple central nervous facets of mood control and is involved in the regulation of sleep, anxiety disorders, alcoholism, drug abuse, food intake and sexual behaviour. In peripheral tissues, serotonin has been reported to be involved in the regulation of vascular tone, intestinal motility, primary hemostasis, and cell-mediated immune responses. Walther, D.J., et al., Science 299:76 (2003). [0003] The enzyme tryptophan hydroxylase (TPH) catalyzes the rate-limiting step in serotonin biosynthesis. Two isoforms of TPH have been reported: TPH1, which is expressed peripherally, mainly in the gastrointestinal tract (GI); and TPH2, which is expressed in the brain. The source is the same as above. The isoform TPH1 is encoded by the tph1 gene; TP...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07D239/47C07C43/23
CPCC07D239/42C07C43/23C07D239/47
Inventor 休·艾尔弗雷德·博古恩拉玛奈亚·C·卡纳马拉普第伊恩·弗雷瑟·皮科尔斯基尔史志才吴文学张海明赵芒柱
Owner LEXICON PHARM INC
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