On June 28, 2012, Bohno, Ayako; Matsuda, Daisuke; Otake, Norikazu; Kakinuma, Hiroyuki; Kobashi, Yohei; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Iwata, Yuki; Hamada, Makoto published a patent.Name: 2-Chloro-5-isopropylpyrimidine The title of the patent was Preparation of 4-piperidinyl-condensed heterocyclic compounds as GPR119 agonists. And the patent contained the following:
The title compounds represented by general formula [I; group A = each (un)substituted Ph or 5 or 6-membered heteroaryl; W = a single bond, O, NH, OCH2, or CH2O; X = a nitrogen atom or CR21; Y1 = a nitrogen atom or CR22; Y2 = a nitrogen atom or CR23; Y3 = a nitrogen atom or CR24; R21, R22, R23, R24 = a hydrogen atom or C1-6 alkyl; group B = C2-6 alkyl, C3-8 cycloalkyl, (C3-8 cycloalkyl)C1-6 alkyl, (aryl)C1-6 alkyl, (saturated heterocyclyl)C1-6 alkyl, CO2R31 (R31 = C1-6 alkyl, C3-8 cycloalkyl, aryl or saturated heterocyclyl), or 5 or 6-membered heteroaryl] or pharmaceutically permitted salts thereof are prepared These compounds including indazolylpiperidine, benzotriazolylpiperidine, pyrazolopyridinylpiperidine, and triazolopyridinylpiperidine compounds have an outstanding glucose-dependent insulinotropic polypeptide receptors (GPR119) agonist action. They are useful as blood-sugar lowering agents for the prevention and/or treatment of diabetes. Thus, a solution of 150 mg tert-Bu 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl]piperidine-1-carboxylate in 1.5 mL DMF was treated with 155 mg 4-(1H-Tetrazol-1-yl)phenyl trifluoromethanesulfonate, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride and 525 μL 2 M aqueous Na2CO3 solution, stirred at 100° for 1.5 h, and concentrated under reduced pressure to give, after silica gel chromatog., 100 mg tert-Bu 4-(5-[4-(1H-tetrazol-1-yl)phenyl]-1H-indazol-1-yl)piperidine-1-carboxylate (II). II and 4-[3-[1-(5-Chloropyrimidin-2-yl)piperidin-4-yl]-3H-[1,2,3]triazolo[4,5-c]pyridin-6-yl]-N-ethyl-2,3-difluorobenzamide(III) in vitro promoted the cellular production of cAMP with ED50 of 13 and 2 nM, resp., in cells expressing human GPR119. The experimental process involved the reaction of 2-Chloro-5-isopropylpyrimidine(cas: 596114-50-0).Name: 2-Chloro-5-isopropylpyrimidine
The Article related to diabetes prevention treatment piperidinyl condensed heterocyclic compound preparation, piperidinyl condensed heterocyclic compound preparation gpr119 agonist, indazolylpiperidine benzotriazolylpiperidine preparation gpr119 agonist, pyrazolopyridinylpiperidine triazolopyridinylpiperidine preparation gpr119 agonist and other aspects.Name: 2-Chloro-5-isopropylpyrimidine
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia