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Immunoregulatory agents
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A technology of solvates and compounds, applied in the field of compounds that regulate oxidoreductase indoleamine 2,3-dioxygenase, can solve problems such as different functions
Active Publication Date: 2017-08-01
FLEXUS BIOSCI
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A homolog of IDO (IDO2) has been identified that shares 44% amino acidsequence identity with IDO, but functions largely differently from IDO
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[0366] Using general procedure B, use a mixture containing cis-(4-phenylcyclohexyl)methanamine (19 mg, 0.1 mmol), 4-cyanobenzoyl chloride (17 mg, 0.1 mmol) and NEt 3 (51 mg, 0.5 mmol) CH 2 Cl 2 (1 mL) was prepared. Purification using silica gelchromatography (10% to 30% EtOAc / hexanes) gave the desired product as a white solid. 1 H NMR (400MHz; CDCl 3 ):δ7.89-7.86(m,2H),7.74-7.71(m,2H),7.32-7.17(m,5H),6.32-6.30(m,1H),3.58(dd,J=7.7,6.0Hz ,2H),2.66-2.59(m,1H),2.06-2.00(m,1H),1.80-1.69(m,8H). m / z 319.3 (M+H + ).
[0370] Using general procedure B, use a mixture containing cis-(4-phenylcyclohexyl)methanamine (19 mg, 0.1 mmol), 3-cyanobenzoyl chloride (17 mg, 0.1 mmol) and NEt 3 (51 mg, 0.5 mmol) CH 2 Cl 2 (1 mL) was prepared. Purification using silica gelchromatography (10% to 30% EtOAc / hexanes) gave the desired product as a white solid. 1 H NMR (400MHz; CDCl 3 ):δ8.09-8.08(m,1H),8.04(dt,J=7.9,1.5Hz,1H),7.76(dt,J=7.7,1.3Hz,1H),7.56(t,J=7.8Hz, 1H), 7.32-7.17(m, 5H), 6.49-6.46(m, 1H), 3.58(dd, J=7.7, 6.0Hz, 2H), 2.66-2.59(m, 1H), 2.07-2.01(m, 1H), 1.80-1.68 (m, 8H). m / z 319.2 (M+H + ).
[0374] Using general procedure B, use a mixture containing cis-(4-phenylcyclohexyl)methanamine (19 mg, 0.1 mmol), 4-chlorobenzoyl chloride (19 mg, 0.1 mmol) and NEt 3 (51 mg, 0.5 mmol) CH 2 Cl 2(1 mL) was prepared. Purification using silica gelchromatography (0% to 20% EtOAc / Hexanes) gave the desired product as a white solid. 1 H NMR (400MHz; CDCl 3 ):δ7.73-7.69(m,2H),7.41-7.38(m,2H),7.31-7.23(m,4H),7.20-7.16(m,1H),3.55(dd,J=7.7,5.9Hz ,2H), 2.63-2.59(m,1H), 2.04-1.98(m,1H), 1.79-1.67(m,8H). m / z 328.2 (M+H + ).
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Abstract
Compounds that modulate the oxidoreductaseenzyme 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 US Provisional Application Serial No. 62 / 075,678, filed November 5, 2014, which is hereby incorporated by reference in its entirety. [0003] Background of the invention [0004] 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 mouse and human sharing 63% sequence identity at the amino acid level. Data derived from its crystal structure and site-directed mutagenesis show that both substrate binding and the relationship between substrate and iron-bound dioxygenase are necessary for activity. ...
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