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A compound and its use

A technology of compounds, compound structures, applied in the field of compounds

Active Publication Date: 2022-01-25
SCINNOHUB PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] As a new type of IDO inhibitor, BMS-986205 is currently in the phase II clinical research stage, but there is still a lot of room for improvement in its efficacy and pharmacokinetic properties

Method used

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  • A compound and its use
  • A compound and its use
  • A compound and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0242] Example 1: 4-((1s,4s)-4-(1-(6-chloro-1H-benzo[d]imidazol-2-yl)ethyl)cyclohexane)-6-fluoroquinoline preparation

[0243] The synthesis steps are as follows:

[0244]

[0245] Step 1: Preparation of 1,4-dioxaspiro[4.5]dec-7-en-8-yl triflate

[0246] Under nitrogen protection, LiHMDS (1M, 1.5L, 1500.0mmol) was added dropwise to a dry THF (2L) solution containing 1,4-dioxaspiro[4.5]dec-8-one (200.0g, 1280.6mmol) , the system temperature was controlled at -78°C to -65°C, after the dropwise addition was completed, the reaction mixture was stirred and reacted at -78°C for 2h. Slowly add 1,1,1-trifluoro-N-phenyl-N-((trifluoromethyl)sulfonyl)methanesulfonamide (457.5 g, 1280.7 mmol) in dry THF (1.5 L) dropwise to the reaction system solution, the temperature of the system was controlled at -78°C to -65°C, the reaction mixture was naturally warmed to room temperature, stirred and reacted overnight, the reaction mixture was slowly poured into ice water, extracted three times...

Embodiment 2、3

[0271] Example 2, 3: 4-((1s,4s)-4-(1-(6-chloro-1H-benzo[d]imidazol-2-yl)ethyl)cyclohexane)-6-fluoroquine Preparation of morphine (homochiral, absolute configuration undetermined)

[0272] The synthesis steps are as follows:

[0273]

[0274] Step 1: 4-((1s,4s)-4-(1-(6-Chloro-1H-benzo[d]imidazol-2-yl)ethyl)cyclohexane)-6-fluoroquinoline (pure chiral, absolute configuration undetermined)

Embodiment 2

[0276] Embodiment 2: 1H NMR (400MHz, d 6 -DMSO)δ1.17-1.33(1H,m),1.34(3H,d,J=6.8Hz),1.50-1.65(2H,m),1.66-1.92(4H,m),1.93-2.20(2H, m),3.33-3.44(2H,m),7.10-7.14(1H,m),7.43-7.49(1H,m),7.50-7.59(2H,m),7.63-7.69(1H,m),7.95- 8.00(1H,m),8.08-8.11(1H,m),8.86(1H,d,J=4.4Hz),12.45-12.50(1H,m).

[0277] EM (calculated): 407.2; MS (ESI) m / e (M+H) + : 408.2

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Abstract

The present invention provides a new compound, which has certain inhibitory activity on the oxidoreductase indoleamine 2,3-dioxygenase (IDO), or can be used to treat related diseases, including cancer and immune-related disease use.

Description

[0001] The present invention is a later application of the earlier application with the application number CN201711423612.1. The present invention claims the priority of the earlier application, and the content recorded in the earlier application can be used as a supplement to the present invention. technical field [0002] The invention relates to the field of medicinal chemistry, in particular to a compound and its application. Background technique [0003] The full name of IDO is indoleamine 2,3 dioxygenase, which is a monomeric enzyme containing heme and the rate-limiting enzyme of human tryptophan metabolism. Like PD-1, it also regulates tumor immune response Key immunosuppressive enzyme. IDO is silent in most tissues, but IDO is continuously expressed in many tumor cells, resulting in a decrease in intracellular tryptophan levels and the production of a series of metabolites, which in turn affect immune and nervous system functions. [0004] The role of IDO is to deco...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/08C07D473/28C07D401/14C07F9/6558C07D413/08C07D471/04C07D487/04C07D473/34C07D473/08C07D473/04C07D498/04C07D491/056C07F9/6561A61K31/4709A61K31/52A61K31/522A61K31/496A61K31/5377A61K31/506A61K31/517A61K31/4985A61K31/519A61K31/675A61P35/00A61P35/02A61P37/00A61P31/12A61P25/24A61P31/18A61P19/00A61P25/22A61P27/12
CPCA61P19/00A61P25/22A61P25/24A61P27/12A61P31/12A61P31/18A61P35/00A61P35/02A61P37/00C07D401/08C07D401/14C07D413/08C07D471/04C07D473/04C07D473/08C07D473/28C07D473/34C07D487/04C07D491/056C07D498/04C07F9/65586C07F9/65616
Inventor 黄浩喜刘冠锋任俊峰易守兵陈垌珲何权鸿吴鲜财李英富苏忠海
Owner SCINNOHUB PHARM CO LTD