METHOD FOR PRODUCING METHYL- {4,6-DIAMINO-2-[1-(2-FLUOROBENZYL) -1H-PYRAZOLO[3,4-B]PYRIDIN-3-YL]-PYRIMIDIN-5-YL}-METHYL CARBAMATE AND ITS PURIFICATION FOR ITS USE AS A PHARMACEUTICAL AGENT

• Main Authors: SIEGEL, Konrad, JOENTGEN, Winfried, MAIS, Franz-Josef, REHSE, Joachim
• Format: Patent
• Language: English; Serbian
• Published: 28.04.2016
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

Postupak za pripremanje metil {4,6-diamino-2-[1-(2-fluorobenzil)-1H-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}metilkarbamata sa formulom (I), naznačen time što se 2-[1-(2-fluorobenzil)-1H-pirazolo[3,4-b]piridin-3-il]-5-[(E)-fenildiazenil]pirimidin-4,6-diamin sa formulom (III) razdvaja pomoću katalitičke hidrogenizacije i time što se 2-[1-(2-fluorobenzil)-1H-pirazolo[3,4-b]piridin-3-il]-4,5,6-pirimidintriamin sa formulom (VIII), posle filtracije katalizatora, precipitira iz C1-C4-alkohola i/ili vode bez posrednog formiranja soli.Prijava sadrži još 1 patentni zahtev. Preparing (P1) methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate (I), involves cleavage of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine by catalytic hydrogenation, and isolation of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine without intermediate formation of salts. Preparing (P1) methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate (I), involves: either cleavage of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine by catalytic hydrogenation, and isolation of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine without intermediate formation of salts; or reactionof 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine with methyl chloroformate or dimethyl dicarbonate to give methyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylcarbamate via a pyridine-free reaction route. Independent claims are included for the following: (1) purifying methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate, involving dissolving crude methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate in dimethyl sulfoxide; isolating the resulting methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate sulfinyldimethane; and removing the dimethyl sulfoxide by boiling in a solvent; (2) new methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate sulfinyldimethane (II); and (3) methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate is prepared by the process (P1). ACTIVITY : Cardiovascular-Gen.; Cardiant; Antianginal; Vasotropic; Antiarrhythmic; Thrombolytic; Cerebroprotective; Thrombolytic; Antiarteriosclerotic; Antiasthmatic; Cytostatic; Endocrine-Gen.; Osteopathic; Ophthalmological; Hypotensive; Respiratory-Gen.; Uropathic. No biological data given. MECHANISM OF ACTION : Soluble guanylate cyclase stimulator.