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Immunomodulators, compositions and methods thereof

A technology of compounds and chelates, applied in the field of pharmaceutically active compounds

Pending Publication Date: 2021-02-19
BETTA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, small molecule inhibitors directly targeting PD-1 or PD-L1 are still not approved, and only CA170 has been clinically evaluated

Method used

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  • Immunomodulators, compositions and methods thereof
  • Immunomodulators, compositions and methods thereof
  • Immunomodulators, compositions and methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0213] The synthesis of embodiment 1 compound 1

[0214] 2-(2-(1'-Methyl-[4,4'-diindoline]-1-carbonyl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H) -yl)acetic acid

[0215]

[0216] To a solution of 4-bromoindole (50 mg) in ACN (20 mL) was added iodomethane (100 mg) and K 2 CO 3 (100mg). The mixture was stirred at 80°C for 12 hours. After the resulting solution was concentrated, the resulting solid was purified by column chromatography to give 4-bromo-1-methylindoline (50 mg).

[0217] To a solution of 4-bromo-1-methylindoline (100 mg) in dioxane (6 mL) was added 4,4,4',4',5,5,5',5'-octamethyl -2,2'-bis(1,3,2-dioxaborinane) (100mg), KOAC (50mg), Pd(dppf)Cl 2 (20mg). The mixture was stirred at 85°C for 12 hours. After the obtained solution was concentrated, the obtained solid was purified by column chromatography to obtain Compound 1-2 (100 mg).

[0218] Compound 1-2 (50mg), compound 4-3 (40mg), K 2 CO 3 (60mg) and Pd(dppf)Cl 2 (10 mg) in 1,4-dioxane (6 mL) and water...

Embodiment 4

[0219] The synthesis of embodiment 4 compound 4

[0220] 2-(2-(4-Phenylindoline-1-carbonyl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)acetic acid

[0221]

[0222] Step 1: Preparation of tert-butyl 2-(4-bromoindole-1-carbonyl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-acetate

[0223] To a solution of 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid (200 mg) in dry dichloromethane was added HATU (200 mg) and DIEA (5 mL). The mixture was stirred for 10 minutes. 4-Bromoindoline was added. The mixture was stirred at room temperature for two hours. After adding 100 mL of EA, washed with brine (4X20 mL). Na for organic phase 2 SO 4 dry. After the resulting solution was concentrated, the resulting solid was purified by column chromatography to give 2-(4-bromoindoline-1-carbonyl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H )-acetate (120mg).

[0224] Step 2 Preparation of (4-bromoindol-1-yl)(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)met...

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PUM

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Abstract

Disclosed are compounds of Formula I, methods of using the compounds as immunomodulators, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating, preventing orameliorating diseases or disorders such as cancer or infections. (I).

Description

technical field [0001] The present invention relates to pharmaceutically active compounds. The invention provides the compound, its composition and application method. Compounds modulate PD-1 / PD-L1 protein / protein interactions and are useful in the treatment of various diseases including infectious diseases and cancer. Background technique [0002] The immune system plays an important role in controlling and eliminating diseases such as cancer. However, cancer cells often employ strategies to evade or suppress the immune system, thereby promoting their growth. One such mechanism is the altered expression of co-stimulatory and co-inhibitory molecules on immune cells (Postowetal, J. Clinical Oncology 2015, 1-9). Blocking the signaling of inhibitory immune checkpoints such as PD-1 has proven to be a promising, effective form of treatment. [0003] The interaction between PD-1 and PD-L1 leads to a decrease in tumor-infiltrating lymphocytes, a decrease in T cell receptor-medi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/04C07D409/02C07D409/14C07D411/02A61K31/403A61P35/00A61P37/00C07D411/14
CPCA61P35/00A61P37/00C07D513/04C07D471/04C07D498/04C07D519/00C07D417/14C07D487/04C07D417/06
Inventor 付邦张垚王义乾刘湘永王家炳丁列明
Owner BETTA PHARM CO LTD
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