On July 1, 2021, Pinkerton, Anthony; Sergienko, Eduard; Kiyotsuka, Yohei; Kagechika, Katsuji; Kurosaki, Yasunobu; Arai, Yoshikazu; Nagamochi, Masatoshi; Ishibashi, Koutaro published a patent.Safety of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol The title of the patent was Preparation of bicyclic heteroaryls, especially thienopyrimidines, as ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) modulators. And the patent contained the following:
The invention is related to the preparation of bicyclic heteroaryl-based small mol. modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), e.g., of formula I [B = aryl or a 5 or 6-membered heteroaryl; n = 0-3; X = (CH2)1-2; p = 0-3; Y1 = NR4, O; L1 = Y2L2, Y2L2L3; Y2 = a bond, CO; L2 = a bond, (un)substituted alk(en/yn)ylene, heteroalkylene, C2-C6 cycloalkylene; R1 = H, halo, CN, OH, etc.; R2 = H, COOH and derivatives, fluoroalkoxy, etc.; R3 = H, halo, SH and derivatives, NH2 and derivatives, etc.; R5 = independently at each occurrence H, NO2, CN, SO2NH2 and derivatives, etc.; R6 = independently at each occurrence halo, alk(en/yn)yl, etc.; ], their pharmaceutically acceptable salts and solvates , compositions containing them, and methods of using the compounds and compositions comprising the compounds for treating disorders associated with ENPP1, such as pseudogout. Thus, II was prepared by cyclization of Me 3-amino-4-methylthiophene-2-carboxylate with formamide, chlorination of 7-methylthieno[3,2-d]pyrimidin-4-ol with POCl3, amination of 4-chloro-7-methylthieno[3,2-d]pyrimidine with tert-Bu (piperidin-4-yl)carbamate, cleavage of tert-butoxycarbonyl group and benzylation of 1-(7-methylthieno[3,2-d]pyrimidin-4-yl)piperidin-4-amine with benzyl chloride. II inhibited ENPP1 in a TR-FRET assay (IC50 in the range of 0.1μM – 1.0μM). The experimental process involved the reaction of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol(cas: 314021-93-7).Safety of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol
The Article related to bicyclic heteroaryl preparation ectonucleotide pyrophosphatase phosphodiesterase 1 enpp1 inhibitor, thienopyrimidine pyrazolopyrimidine pyrazolopyridine thienopyridine preparation enpp1 inhibitor pseudogout antiarthritic, triazolopyrimidine isoxazolopyrimidine pyrazolopyridazine isothiazolopyrimidine preparation enpp1 inhibitor and other aspects.Safety of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics