Riociguat Impurity 20

6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dihydro-8H-purin-8-one Methyl [4,6-diaMino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyriMidin-5-yl]carbaMate 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dimethyl-7,9-dihydro-8H-purin-8-one BENZENEAZOMALONONITRILE isopropyl(4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b] pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate

Riociguat IMpurtiy 5 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl) -7-methyl-7,9-dihydro-8H-purin-8-one Methyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbiMidate Riociguat Impurity 9 Riociguat Impurity 7

1-benzyl-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide hydrochloride Riociguat Impurity 22 Riociguat Impurity 8 Riociguat IMpurtiy 3 1-(4-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

1-benzyl-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Riociguat Impurity 19 Riociguat Impurity 18