Immunoregulatory agents

A solvate and compound technology, which is applied in the field of compounds that regulate oxidoreductase indoleamine 2,3-dioxygenase, and can solve problems such as different functions

Active Publication Date: 2017-12-01
FLEXUS BIOSCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

An analog of IDO (IDO2) has been identified that shares 44% amino acid

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 and 2

[0341] N-(4-Chlorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide

[0342]

[0343] N-(4-Chlorophenyl)-2-(4-(cis-quinolin-4-yl)cyclohexyl)acetamide

[0344]

[0345] Examples 1 and 2: N-(4-chlorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide and N-(4-chlorophenyl)-2-( cis-4-(quinolin-4-yl)cyclohexyl)acetamide

[0346] Examples 1 and 2 were prepared using general procedures A, B and G. General procedure A used 7.91 g (25 mmol) ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate and 4.56 g (26 mmol) quinoline -4-boronic acid. General procedure B used 20 wt% dry Pd / C (10 wt%) and methanol as solvent. General Procedure G used 100 mg ethyl 2-(4-(quinolin-4-yl)cyclohexyl)acetate (mixture of diastereomers) and 87 mg 4-chloroaniline. Purification using silica gel chromatography (0% to 60% ethyl acetate / toluene) afforded Example 1 (trans-diastereomer) as the first eluting isomer. trans-isomer 1 HNMR (400MHz; CDCl 3):δ8.85(d,J=4.6Hz,1H),8.0...

Embodiment 3 and 4

[0349] N-(4-cyanophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide hydrochloride

[0350]

[0351] N-(4-cyanophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)acetamide hydrochloride

[0352]

[0353] Examples 3 and 4: N-(4-cyanophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide hydrochloride and N-(4-cyanophenyl )-2-(cis-4-(quinolin-4-yl)cyclohexyl)acetamide hydrochloride

[0354] Examples 3 and 4 were prepared using general procedures A, B and G. General procedure A used 7.91 g (25 mmol) ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate and 4.56 g (26 mmol) quinoline -4-boronic acid. General procedure B used 20 wt% dry Pd / C (10 wt%) and methanol as solvent. General Procedure G uses 100 mg ethyl 2-(4-(quinolin-4-yl)cyclohexyl)acetate (mixture of diastereomers) and 80 mg 4-cyanoaniline. Purification using silica gel chromatography (0% to 60% ethyl acetate / toluene) afforded Example 3 (trans-diastereomer) as the first eluting isomer. The free ba...

Embodiment 5 and 6

[0357] N-(4-fluorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide

[0358]

[0359] N-(4-fluorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)acetamide

[0360]

[0361] Examples 5 and 6: N-(4-fluorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide and N-(4-fluorophenyl)-2-( cis-4-(quinolin-4-yl)cyclohexyl)acetamide

[0362] Prepared using general procedures A, B and G. General procedure A used 7.91 g (25 mmol) ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate and 4.56 g (26 mmol) quinoline -4-boronic acid. General procedure B used 20 wt% dry Pd / C (10 wt%) and methanol as solvent. General Procedure G used 100 mg ethyl 2-(4-(quinolin-4-yl)cyclohexyl)acetate (mixture of diastereomers) and 76 mg 4-fluoroaniline. Purification using silica gel chromatography (0% to 60% ethyl acetate / toluene) afforded Example 5 (trans-diastereomer) as the first eluting isomer. trans-isomer 1 HNMR (400MHz; CDCl 3 ):δ8.85(d,J=4.5Hz,1H),8.05-8.15(m,2H),7.67-7.7...

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Abstract

Compounds that modulate the oxidoreductase enzyme indoleamine 2,3- dioxygenase, and compositions containing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by indoleamine 2,3-dioxygenase is also provided.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to U.S. Provisional Application Nos. 62 / 075,671, filed November 5, 2014, and 62 / 098,022, filed December 30, 2014, respectively, the entire contents of which applications are incorporated herein by reference middle. Background of the invention [0003] Indoleamine 2,3-dioxygenase (IDO; also known as IDO1) is an IFN-γ target gene that plays a role in immune regulation. IDO is an oxidoreductase and is one of two enzymes that catalyze the first and rate-limiting step in the conversion of tryptophan to N-formyl-kynurenine. It exists as a 41 kD monomer found in several cell populations including immune cells, endothelial cells and fibroblasts. IDO is relatively well conserved between species, with mice and humans sharing 63% sequence identity at the amino acid level. Data derived from its crystal structure and site-directed mutagenesis show that substrate binding and the relationship between...

Claims

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Application Information

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IPC IPC(8): A61K31/4375A61K31/4709A61K31/496
CPCC07D487/04C07D215/06A61K31/47C07D231/56A61K31/416C07D215/233C07D471/04A61K31/437C07D239/74A61K31/517A61K31/4375C07D217/04C07D405/08A61K31/4709C07D417/08C07D401/12C07D401/14A61K31/496A61K31/519A61K45/06C07D215/14C07D405/12C07D417/12A61P35/02C07D215/12C07D217/12C07D217/24A61K2300/00A61K31/506A61K39/39558
Inventor H.P.贝克J.C.耶恩M.奥西波夫J.P.鲍尔斯M.K.雷利H.P.舒纳托纳J.R.沃尔克M.兹宾斯基J.A.巴洛格D.K.威廉斯J.A.马克沃尔德E.C.彻尔尼W.单A.黄
Owner FLEXUS BIOSCI
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