Inhibitors of indoleamine 2,3-dioxygenase (IDO)
A C3-C8, C2-C10 technology, applied in the field of enzyme active compounds, can solve the problem of increased tolerance of the tumor microenvironment
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[0223] The preparation of prodrugs is well known in the art and described in, for example, King, F.D., ed., Medicinal Chemistry: Principles and Practice, The Royal Society of Chemistry, Cambridge, UK (2 nd edition,reproduced,2006); Testa,B.etal.,HydrolysisinDrugandProdrugMetabolism.Chemistry,BiochemistryandEnzymology,VCHAandWiley-VCH,Zurich,Switzerland(2003);Wermuth,C.G.,ed.,The Practice ofMedicinalChemistry,3 rd edition, Academic Press, San Diego, CA (2008).
[0224] The present invention is intended to include all isotopes of atoms present in the compounds of the present invention. Isotopes include atoms that have the same atomic number but different mass numbers. By way of general example and not limitation, isotopes of hydrogen include deuterium and tritium. Isotopes of carbon include 13 C and 14 C. The isotope-labeled compounds of the present invention can be prepared as follows: generally by conventional techniques known to those skilled in the art or by methods similar t...
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[0386] Racemic Example 1. Racemic (1R, 2S)-2-(4-(diisobutylamino)-3-(3-(p-tolyl)ureido)phenyl)cyclopropanecarboxylic acid
[0387] To a solution of 1D (140 mg, 0.421 mmol) in THF (4 mL) was added 1-isocyanato-4-methylbenzene (0.079 mL, 0.632 mmol). The resulting solution was stirred at room temperature for 3h. LC-MS indicated completion. The reaction mixture was concentrated and used in the next step without purification. The crude ester (180 mg, 0.387 mmol) was dissolved in THF (4 mL), and NaOH (1N aqueous solution) (1.160 mL, 1.160 mmol) was added. Then MeOH (1 mL) was added to dissolve the precipitate and it became a clear yellow solution. After 60h, LC-MS indicated that the reaction was complete. Most of the MeOH and THF were removed in vacuo and the crude product was diluted with 2 mL of water, and the pH was adjusted to about 2 using 1N aqueous HCl. Then the aqueous phase was extracted with EtOAc (3×10 mL) and the combined organic phase was washed with brine, and Na 2 ...
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[0424] Example 2-16
[0425]
[0426] Following the procedure of Example 1, Enantiomer 1, Method C, using the corresponding isocyanate, Examples 2-16 were prepared.
[0427]
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