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Deuterated compounds for the treatment of hematological malignancies, inflammation and autoimmune diseases

An autoimmune, malignant tumor technology, applied in the field of deuterated compounds for the treatment of hematological malignancies, inflammation and autoimmune diseases, can solve the problems of limited clinical effectiveness, undesired side effects, etc.

Active Publication Date: 2022-07-05
NEUFORM PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although drugs have been developed to treat some of these diseases and conditions, available treatments are often limited in clinical effectiveness and simultaneously have undesired side effects

Method used

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  • Deuterated compounds for the treatment of hematological malignancies, inflammation and autoimmune diseases
  • Deuterated compounds for the treatment of hematological malignancies, inflammation and autoimmune diseases
  • Deuterated compounds for the treatment of hematological malignancies, inflammation and autoimmune diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0132] compound synthesis

[0133] Scheme 1 outlines an exemplary synthetic method.

[0134] plan 1

[0135]

[0136] resolve resolution

[0137] Step 1. Synthesis of Compound 3

[0138] To a solution of 2-fluoro-6-nitrobenzoic acid 1 (100 g, 0.54 mol) and dimethylformamide (DMF) (5 mL) in dichloromethane was added oxalyl chloride (2M in DCM, 410 mL, 1.5 equiv). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure to give an orange syrup. The residue was dissolved in dry dioxane (80 mL) and slowly added to aniline 2 (49 mL, 1 equiv) and sodium bicarbonate (90 g, 2 equiv) in dioxane (250 mL) cooled in an ice-water bath and water (250 mL). After 30 minutes, the reaction mixture was treated with water (1.2 L). The precipitate was filtered, washed with water, air dried, and then dried under vacuum at 50°C for 24 hours to give 3 (139 g, 99%) as an off-white solid.

[0139] Steps 2 and 3. Synthesis of Compound ...

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Abstract

The present invention provides novel chemical compounds useful for the treatment of various hematological malignancies and inflammatory and autoimmune diseases or related diseases or disorders, as well as pharmaceutical compositions, preparation methods and uses thereof.

Description

[0001] Priority Claims and Related Patent Applications [0002] This application claims the benefit of priority from US Provisional Application Serial No. 62 / 255,704, filed November 16, 2015, and Serial No. 62 / 312,499, filed March 24, 2016, the entire contents of each of which are hereby incorporated by reference in their entirety. Incorporated into this article in its entirety. technical field [0003] The present invention generally relates to methods of treatment and management for certain diseases and conditions. More specifically, the present invention provides (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-8-chloro-2- with one or more deuterium substitutions at key positions Novel compounds of phenylisoquinolin-l(2H)-ones that exhibit immunomodulatory and antitumor activity and are useful in the treatment of various hematological malignancies and inflammatory and autoimmune diseases and related diseases and conditions; and Pharmaceutical composition and preparation method and u...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/34C07B59/00A61K31/52A61K38/02A61K39/395A61P35/00
CPCA61K38/00A61K39/395C07D473/34A61K45/06C07B59/002A61P35/00
Inventor 程昌富黄超然
Owner NEUFORM PHARMA INC
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