GPR120 protein receptor inhibitor as well as preparation and application thereof

A C1-C6, C1-C4 technology, applied in the field of small molecule protein inhibitors, can solve problems such as unobserved

Pending Publication Date: 2021-06-01
NANJING IMMUNOPHAGE BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this effect was not observed in GPR120 knockout mice

Method used

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  • GPR120 protein receptor inhibitor as well as preparation and application thereof
  • GPR120 protein receptor inhibitor as well as preparation and application thereof
  • GPR120 protein receptor inhibitor as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0072] The preparation of formula I compound

[0073] The present invention also provides a method for preparing the compound as described in the first aspect of the present invention, comprising the steps of:

[0074]

[0075] In an appropriate solvent, react with alcohol Ia and phenol Ib to obtain compound Ic, and obtain a compound of formula I after deprotection, wherein LG is a leaving group, preferably C 1 -C 4 alkyl.

[0076] Pharmaceutical compositions and methods of administration

[0077] Since the compound of the present invention has excellent GPR120 inhibitory activity, the compound of the present invention and its various crystal forms, pharmaceutically acceptable inorganic or organic salts, hydrates or solvates, and compounds containing the compound of the present invention as the main active ingredient The pharmaceutical composition can be used to prevent and / or treat diseases related to GPR120 signaling pathway (for example, cancer).

[0078] The pharmac...

Embodiment 1

[0092] 3-(4-((2-isopropyl-5-methylbenzyl)oxy)-3-methylphenyl)propanoic acid

[0093]

[0094] Step 1: Synthesis of (2-isopropyl-5-methylphenyl)methanol

[0095] A solution of 2-isopropyl-5-methylbenzaldehyde (100 mg, 0.62 mol) in THF (5 mL) was cooled to -78 °C. LAH (1.0 M in THF, 0.8 mL, 0.8 mmol) was added at this temperature and the reaction was allowed to warm to room temperature. The reaction was poured into ice-water mixture, and extracted with ethyl acetate (20 mL*2). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography to afford the title compound as a yellow oil (80 mg, 80% yield). MS(ESI): m / z 165.5(M+H) + .

[0096] Step 2: Synthesis of methyl 3-(4-(((2-isopropyl-5-methylbenzyl)oxy)-3-methylphenyl)propanoate

[0097] (2-Isopropyl-5-methylphenyl)methanol (80mg, 0.49mmol), methyl 3-(4-hydroxy-3-methylphenyl)propionate (105mg, 0.54mmol) and PPh 3 (14...

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PUM

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Abstract

The invention provides a GPR120 protein receptor inhibitor and preparation and application thereof, and particularly provides a compound as shown in the following formula I in the specification or pharmaceutically acceptable salt thereof. The compound disclosed by the invention has excellent GPR120 protein inhibition activity.

Description

technical field [0001] The present invention relates to the field of small molecule protein inhibitors, specifically, the present invention provides the preparation and application of a compound with regulation function of GPR120 protein. Background technique [0002] GPR120, a G protein-coupled receptor, induces various biological responses by binding to unsaturated long-chain fatty acids such as α-linoleic acid to cause intracellular signaling. The action of GPR120 and its ligands has been reported to promote the secretion of glucagon-like peptide 1 ("GLP-1"), thereby reducing blood glucose levels in gastrointestinal cell lines. GLP-1, which is a peptide hormone, has been found to induce insulin secretion in response to blood glucose levels. The use of GLP-1 has also been suggested to delay beta-cell apoptosis in type II diabetes. [0003] GPR120 is expressed in adipocytes. Increasing expression of GPR120 has been found to be induced by adipogenic differentiation. Addi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/64C07C255/54C07D213/65A61P3/10A61P3/04A61P3/06A61P29/00A61K31/192A61K31/277A61K31/44
CPCC07C59/64C07C255/54C07D213/65A61P3/10A61P3/04A61P3/06A61P29/00C07C2601/02
Inventor 范国煌
Owner NANJING IMMUNOPHAGE BIOTECH CO LTD
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