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Novel tricyclic compound as irak4 inhibitor

A cyclic compound, chemical formula technology, applied in the field of new tricyclic compounds as IRAK4 inhibitors, can solve the problems of inability to greatly improve the disease, high cost, and achieve excellent inhibitory activity.

Pending Publication Date: 2021-08-06
KOREA RES INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Belimumab (Benlysta: belimumab, GSK, 2010), the first new drug for lupus, is an antibody injection that inhibits abnormal B lymphocytes by inhibiting the binding of B-cell receptors of BlyS (BAFF), but it is not only expensive, Also has the problem of not being able to substantially improve the disease

Method used

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  • Novel tricyclic compound as irak4 inhibitor
  • Novel tricyclic compound as irak4 inhibitor
  • Novel tricyclic compound as irak4 inhibitor

Examples

Experimental program
Comparison scheme
Effect test

manufacture example 16

[0132] [Production Example 1] Production of 6-bromo-4-chloro-9H-pyrimido[4,5-b]indole (compound 4a)

[0133]

[0134] Step 1. Production of compound 2a

[0135] After compound 1a (36 g, 143 mmol) was dissolved in dichloromethane (300 ml), triethylamine (40 mL, 287 mmol) was added, and trifluoroacetic anhydride (30 mL, 216 mmol) was added slowly at 0°C. Wash with distilled water (2×300mL) after the reaction finishes, then wash with sodium sulfate (Na 2 SO 4 ) to remove moisture and concentrate under reduced pressure to obtain 50 g of trifluoroacetamide (trifluoroacetamide) derivatives.

[0136] Dissolve the trifluoroacetamide derivative in DMSO (dimethyl sulfoxide)-distilled water (1:1; 280 mL), and add methyl cyanoacetate (15 mL, 170 mmol), DL-proline (3.3 g, 18.8 mmol ), K 2 CO 3 (40g, 289mmol), CuI (2.73g, 14.3mmol), and stirred at 60°C for 14 hours. After cooling the reactant to room temperature, the solid was filtered, washed with methanol (2×100 mL), and the filt...

manufacture example 2

[0144] [Production Example 2] Production of ethyl 4-chloro-9H-pyrimido[4,5-b]indole-6-carboxylic acid methyl ester (compound 4b)

[0145]

[0146] Compound 4b was produced from compound 1b in three steps in the same manner as in Production Example 1 above.

[0147] 4b: 1 H-NMR (300MHz, DMSO-d 6 )δ1.38(t, J=7.1Hz, 3H), 4.38(q, J=7.1Hz, 2H), 7.70(d, J=8.6Hz, 1H), 8.19(dd, J=8.6, 1.3Hz, 1H), 8.80(s,1H), 8.85(s,1H), 13.13(s,1H).

manufacture example 37

[0148] [Production Example 3] Production of 7-bromo-4-chloro-9H-pyrimido[4,5-b]indole (Compound 4c)

[0149] Compound 4c was produced from compound 1c in three steps in the same manner as in Production Example 1 above.

[0150] 4c: 1 H-NMR (300MHz, DMSO-d 6 )δ7.60(dd, J=8.4,1.8Hz,1H),7.81(d,J=1.7Hz,1H),8.22(d,J=8.5Hz,1H),8.83(s,1H),12.94( s, 1H).

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Abstract

The present invention relates to a pharmaceutical composition for preventing or treating autoimmune diseases or tumors, containing, as an active ingredient, a tricyclic compound represented by the following formula 1 or a pharmaceutically acceptable salt thereof, and a health food composition for preventing or alleviating autoimmune diseases or tumors, containing the tricyclic compound as an active ingredient. [Chemical formula 1] A tricyclic compound represented by chemical formula 1 of the present invention has an excellent inhibitory activity against IRAK4, and thus can be effectively used in the prevention, treatment, or alleviation of autoimmune diseases or tumors.

Description

technical field [0001] The present invention relates to a novel tricyclic compound as an IRAK4 inhibitor, a pharmaceutical composition for preventing or treating autoimmune diseases or tumors containing the tricyclic compound or a pharmaceutically acceptable salt thereof as an active ingredient, And a health food composition containing the ternary compound as an active ingredient for preventing or improving autoimmune diseases or tumors. Background technique [0002] IRAK4 (Interleukin-1 receptor (IL-1R) associated kinase 4) acts as a mediator to send Toll-like receptor (TLR) and interleukin-1 receptor (IL-1R) signals into cells in bone marrow cells and lymphocytes It is the main phosphorylase that is transmitted, and it is being actively studied as a therapeutic target for rare immune diseases such as systemic lupus erythematosus (SLE) and lymphoma (Current Topics in Medicinal Chemistry, 2009, 9, 724-737) . [0003] Lupus is an autoimmune disease of unknown cause, if 4 or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P37/00A23L29/00A23L33/10
CPCA23L33/10A61K31/519A61P35/00A61P37/00C07D487/04A23L29/03A23V2002/00A61K31/5377A61K31/541C07D487/14C07D471/14C07D519/00A23V2200/308A23V2200/324A61K2300/00
Inventor 曹姬荣林熙钟朴右圭郑大永金炫暎尹新春李廷玉李兴璟维克托·苏克邦·洪崔智惠
Owner KOREA RES INST OF CHEM TECH
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