On May 22, 2008, Ohlmeyer, Michael J.; Bohnstedt, Adolph; Kingsbury, Celia; Ho, Koc-Kan; Quintero, Jorge published a patent.Synthetic Route of 138801-92-0 The title of the patent was Preparation of 7-substituted purine derivatives as inhibitors of tyrosine kinase Jak3 for immunosuppression. And the patent contained the following:
The present invention provides novel purinone and related derivatives [I; Q1, Q2 = independently CX1, CX2, or N wherein Q1 and Q2 are not both N; Q3 = N or CH; X1, X2 = independently H, C1-6 alkyl, cyano, halo, halo-C1-6 alkyl, HO, C1-6 alkoxy, halo-C1-6 alkoxy, or NO2; R1 = H, C1-6 alkyl; y = 0 or an integer of 1-3 ; R2 and R3 are selected independently for each occurrence of (CR2R3) from H and C1-6 alkyl; R4 = each (un)substituted alkyl, heterocyclyl, aryl, or heteroaryl; R5 = alkyl, (un)substituted heterocyclyl, or C1-C6 alkyl wherein (a) one or two CH2 is replaced by a group chosen from NH and N(alkyl); (b) one or two CH2 is replaced by O; (c) one or two CH2 is replaced by (C:O); (d) two CH2 are replaced by CH:CH or CC; or (e) any chem. stable combination of (a), (b) (c) and (d); and wherein from zero to three hydrogens is replaced by a substituent chosen from: (a) halogen, hydroxy, cyano, lower alkylsulfonyl, lower alkylsulfonyloxy, amino, lower alkylamino, di(lower alkyl)amino, alkoxyamino, sulfonylamino, acylamino, arylamino, lower alkoxy; (b) (un)substituted heterocyclyl; (c) (un)substituted Ph; and (d) (un)substituted heteroaryl]. These compounds are inhibitors of Jak3 kinase and useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease, hematol. malignancy, and transplant rejection. Thus, a solution of 20 mg 3-[9-((R)-6,8-difluorochroman-4-yl)-8-oxo-8,9-dihydro-7H-purin-2-yl]-3H-benzo[d]imidazole-5-carbonitrile in 2 mL MeCN was treated with 90 mg Me bromoacetate and 100 mg 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (2.2 mmol base/g) and the mixture was stirred at room temperature 48 h, and then filtered to give, after concentration of the filtrate in vacuo, Me 2-[2-(6-cyano-1H-benzo[d]imidazol-1-yl)-9-((R)-6,8-difluorochroman-4-yl)-8-oxo-8,9-dihydropurin-7-yl]acetate (II). The compounds I including II showed IC50 of 101 nM-1 μM against tyrosine kinase Jak3. The experimental process involved the reaction of 4-Oxochroman-6-carbonitrile(cas: 138801-92-0).Synthetic Route of 138801-92-0
The Article related to purine derivative preparation immunosuppressant, autoimmune disease inflammatory disease prevention treatment purine derivative preparation, mast cell mediated disease prevention treatment purine derivative preparation, hematol malignancy transplant rejection prevention treatment purine derivative preparation, tyrosine kinase jak3 inhibitor purine derivative and other aspects.Synthetic Route of 138801-92-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts