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Immunomodulator

A heterocycloalkyl group, selected from the technology, applied in the field of immunomodulators and the preparation of drugs

Active Publication Date: 2019-11-29
HITGEN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Despite the existence of multiple IL-17A antibodies, few studies have investigated small molecule-specific inhibitors of IL-17 with orally bioavailable

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0173] The preparation of embodiment 1 intermediate 1

[0174]

[0175] Step 1 Preparation of intermediate 1-1

[0176]

[0177] Ethyl nitroacetate (28.5g, 130mmol) and 5-bromo-2-chlorobenzaldehyde (17.3g, 130mmol) were dissolved in anhydrous tetrahydrofuran (400mL), and titanium tetrachloride was slowly added dropwise at 0°C under nitrogen protection (28.5mL, 260.0mmol), after the dropwise addition, continue to stir the reaction at 0°C for 1 hour. N-methylmorpholine (57.8 mL, 520.0 mmol) was slowly added dropwise to the reaction solution, and after the dropwise addition, the temperature was slowly raised to room temperature, and the reaction was continued to stir for 2 hours. Add distilled water to quench the reaction, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure, and purify by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1 ) to obtain intermediate ...

Embodiment 2

[0190] The preparation of embodiment 2 intermediate 2

[0191]

[0192] Referring to the method for preparing intermediate 1 in Example 1, using o-chlorobenzaldehyde as the starting material, condensation, Grignard reaction, nitro reduction, Boc protected amino group, hydrolysis, and finally separated by SFC chiral separation column to prepare Four single chiral isomers 2-a, 2-b, 2-c, 2-d of intermediate 2 were obtained. MS m / z:242[M-99] + , 286 [M-55] + .

Embodiment 3

[0193] The preparation of embodiment 3 intermediate 3

[0194]

[0195] Referring to the method for preparing intermediate 1 in Example 1, using m-chlorobenzaldehyde as a starting material, condensation, Grignard reaction, nitro reduction, Boc protection of amino groups, hydrolysis, and finally separated by SFC chiral separation column can be prepared respectively Four single chiral isomers 3-a, 3-b, 3-c, 3-d of intermediate 3 were obtained. MS m / z:242[M-99] + , 286 [M-55] + .

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Abstract

The invention discloses an immunomodulator, particularly relates to a class of compounds for inhibiting IL-17A, and uses as immunomodulators in preparation of drugs, and discloses uses of a compound represented by a formula I, or a stereoisomer, or a pharmaceutically acceptable salt thereof in preparation of drugs for inhibiting IL-17A. According to the present invention, the new selection is provided in the clinical screening and / or preparing of drugs for treating diseases related to IL-17A activity.

Description

technical field [0001] The invention relates to an immunomodulator and its use in the preparation of medicines. Background technique [0002] IL-17 (Interleukin-17) is a pro-inflammatory cytokine that plays a role in the induction of other inflammatory cytokines, chemokines and adhesion factors. The IL-17 family consists of cytokines involved in acute and chronic inflammatory responses, including IL-17A (CTLA-8), IL-17B, IL-17C, IL-17D, IL-17E (IL-25) and IL-17F . IL-17A is expressed by TH17 cells, which are involved in the pathogenesis of inflammatory and autoimmune diseases. Human IL-17A is a glycoprotein with a molecular weight of approximately 17,000 Daltons. IL-17A transmits signals into cells through the IL-17 receptor complex (IL-17RA and IL-17RC) (Wright, et al. Journal of immunology, 2008, 181:2799-2805). The main function of IL-17A is through the upregulation of proinflammatory and neutrophil migration cytokines and chemokines including IL-6, G-CSF, TNF-α, IL-1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D403/14C07D405/14C07D413/14A61K31/4184A61K31/5377A61K31/422A61P29/00A61P37/02A61P31/00A61P35/00A61P13/12A61P1/16A61P17/06A61P3/10A61P19/02A61P27/02A61P1/00A61P9/10A61P13/10A61P11/06
CPCA61P1/00A61P1/16A61P3/10A61P9/10A61P11/06A61P13/10A61P13/12A61P17/06A61P19/02A61P27/02A61P29/00A61P31/00A61P35/00A61P37/02C07D403/12C07D403/14C07D405/14C07D413/14A61K31/4184A61K31/422A61K31/5377C07D235/06
Inventor 李进张登友白晓光张维熙尚巳耘钟猛潘垒昌陈伟
Owner HITGEN INC
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