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Benzopyrrolin-2-one derivatives substituted by n-benzoic acid group and use thereof

A technology for methyl and use, applied in the field of N-benzoic acid-substituted benzopyrrolin-2-one derivatives and their uses

Active Publication Date: 2020-11-03
BEIJING HANMI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ligands of nuclear receptors include thyroid hormones, steroid hormones, retinoic acid, fatty acids, sterols, etc. In addition, there is a class of nuclear receptors that have not yet identified ligands, called orphan nuclear receptors

Method used

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  • Benzopyrrolin-2-one derivatives substituted by n-benzoic acid group and use thereof
  • Benzopyrrolin-2-one derivatives substituted by n-benzoic acid group and use thereof
  • Benzopyrrolin-2-one derivatives substituted by n-benzoic acid group and use thereof

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach

[0126] The preparation of the compound of the present application

[0127] The compounds of the examples in this application can be prepared according to the following schemes. However, the following reaction schemes only illustrate the preparation methods of the compounds of the present application.

[0128] It should be understood by those skilled in the art that in the following description, combinations of substituents are permissible only when such combination can result in a stable compound.

[0129] Those skilled in the art will also understand that in the methods described below, the functional groups of intermediate compounds may need to be protected by appropriate protecting groups. Such functional groups include hydroxyl, amino, mercapto and carboxylic acid. Suitable hydroxy protecting groups include trialkylsilyl or diarylalkylsilyl groups (eg tert-butyldimethylsilyl, tert-butyldiphenylsilyl or trimethylsilyl) , tetrahydropyranyl, benzyl, etc. Suitable protec...

Embodiment 1

[0154] Example 1: (trans)-4-(3-(2-chloro-6-cyclopropyl-benzylidene)-4-methylindolin-2-one-1-yl)-2-hydroxyl benzoic acid

[0155]

[0156] Synthetic Compound Example 1 takes (1-1) as the starting material, and the detailed route is as follows:

[0157]

[0158] (1) Step 1: Synthesis of 4-(4-methylindolin-2-one)-iodosalicylic acid methyl ester (1-2)

[0159]

[0160] 4-Methyl-2-indolinone (147 mg, 1 mmol), methyl 4-iodosalicylate (306 mg, 1.1 mmol), dissolved in 2 mL of dioxane, then added iodide Cuprous (38 mg, 0.2 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol), potassium carbonate (415 mg, 3 mmol). Microwave heating at 125°C for 120 minutes. Cool to room temperature, dilute with 20 ml of ethyl acetate, filter, and distill off the solvent under reduced pressure. The residue was separated by column chromatography (silica gel 200-300 mesh, eluent: n-hexane / ethyl acetate=4 / 1) to obtain 4-(4-methylindolin-2-one)-iodosalicylic acid methyl 70 mg of ester, yellow solid, yi...

Embodiment 2

[0169] Example 2: The preparation of the compound of this example can be carried out according to the similar steps of the aforementioned Preparation Example 1, the difference is that in step 1, raw material 3b in Table 1 is used instead of raw material 3a to obtain (trans)-4-( 3-(2-Chloro-6-cyclopropyl-benzylidene)-4-methylindolin-2-on-1-yl)-benzoic acid (2A)

[0170]

[0171] Relevant characterization data are as follows: ESI-MS: [M+H] + =430.3

[0172] 1 H-NMR (300MHz, DMSO-d 6 )δ: ppm 8.03 (d, 2H, J = 8.7Hz), 7.84 (s, 1H), 7.50 (d, 2H, J = 8.7Hz), 7.22 (m, 3H), 6.96 (q, 2H, J = 7.8Hz), 6.73(d, 1H, J=7.8Hz), 2.60(s, 3H), 1.87(m, 1H), 0.81(m, 2H), 0.62(m, 2H).

[0173] and (trans)-4-(3-(2-chloro-6-cyclopropyl-benzylidene)-4-methylindolin-2-on-1-yl)-benzoic acid (2B)

[0174]

[0175] Relevant characterization data are as follows: ESI-MS: [M+H] + =430.2

[0176] 1 H-NMR (300MHz, DMSO-d 6 )δ: ppm 8.03 (d, 2H, J = 8.7Hz), 7.84 (s, 1H), 7.50 (d, 2H, J = 8.7Hz), 7....

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Abstract

Disclosed are a compound, a stereisomer and a tautomer thereof, a pharmaceutically acceptable salt thereof, and a solvate or a prodrug thereof, which can be used for preventing or treating a ROR³ mediated disease. The compound has the structural formula (I).

Description

technical field [0001] The present application relates to compounds useful as retinoic acid-related orphan receptor gamma (RORγ) modulators, their pharmaceutical compositions, their use in pharmacy and their use in the treatment and / or prevention of RORγ in mammals, especially humans Methods of mediating disease. Background technique [0002] Nuclear receptors are a ligand-dependent superfamily of transcription factors, which are widely distributed in organisms and play roles in metabolism, development, biological rhythm, inflammation and immune regulation. The ligands of nuclear receptors include thyroid hormones, steroid hormones, retinoic acid, fatty acids, sterols, etc. In addition, there is a class of nuclear receptors that have not yet identified ligands, called orphan nuclear receptors. Retinoic acid-related orphan receptors (retinoid-relatedorphan receptors, RORs), also known as NF1R, this type of nuclear receptor is due to the gene sequence and retinoic acid recept...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34A61K31/404A61P19/02A61P29/00A61P25/00A61P17/06A61P1/00A61P1/18A61P11/06A61P37/02A61P11/00A61P37/06A61P17/00A61P19/04A61P7/04A61P5/14A61P11/08A61P11/02A61P3/10A61P27/02A61P21/04A61P19/00A61P1/04
CPCC07B2200/09C07D209/34A61K31/03A61K31/192A61K31/196A61K31/404A61P1/00A61P1/04A61P1/18A61P3/10A61P5/14A61P7/00A61P7/04A61P11/00A61P11/02A61P11/06A61P11/08A61P17/00A61P17/06A61P19/00A61P19/02A61P19/04A61P21/04A61P25/00A61P27/02A61P29/00A61P37/02A61P37/06A61P37/08A61P43/00C07D209/08C07D209/10Y02A50/30
Inventor 薛海赵涛马涛车美英金孟燮
Owner BEIJING HANMI PHARMA CO LTD
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