processo para a produção de metil-4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]-5-pirimidinilcarbamato e processo para produção de metil-{4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}metilcarbamato

a presente invenção refere-se a um processo para a produção de metil-{4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}metilcarbamato da fórmula (i), bem como a um processo para a produção de metil-4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]-5-pir...

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Bibliographische Detailangaben
Hauptverfasser: FRANZ-JOSEF MAIS, JOACHIM REHSE, WINFRIED JOENTGEN, KONRAD SIEGEL
Format: Patent
Sprache:por
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Zusammenfassung:a presente invenção refere-se a um processo para a produção de metil-{4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}metilcarbamato da fórmula (i), bem como a um processo para a produção de metil-4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]-5-pirimidinilcarbamato da fórmula (vi). 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; Resp