Riociguat Impurity 16

methyl (5,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b] pyridin-3-yl)pyrimidin-4-yl)carbamate methyl methyl(phenyl)carbamate N-(4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin- 3-yl)pyrimidin-5-yl)-N-methylacetamide Riociguat M1 Glucuronide BENZENEAZOMALONONITRILE

isopropyl(4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b] pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate 1-(4-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Riociguat Impurity 20 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dimethyl-7,9-dihydro-8H-purin-8-one 1-benzyl-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

Riociguat Impurity 19 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 Riociguat Impurity 18 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl) -7-methyl-7,9-dihydro-8H-purin-8-one