JP2017535561A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017535561A5 JP2017535561A5 JP2017526957A JP2017526957A JP2017535561A5 JP 2017535561 A5 JP2017535561 A5 JP 2017535561A5 JP 2017526957 A JP2017526957 A JP 2017526957A JP 2017526957 A JP2017526957 A JP 2017526957A JP 2017535561 A5 JP2017535561 A5 JP 2017535561A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- pyrrolo
- pyrimidin
- pyrazin
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- -1 (5-methylpyrazin-2-yl) -2- (8- (3,3,4,4,4-pentafluorobutyl)-[1,2,4] Triazolo [1,5-a] pyrazin-6-yl) -5H-pyrrolo [2,3-d] pyrimidin-6 (7H) -one Chemical compound 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 206010016654 Fibrosis Diseases 0.000 claims description 8
- 206010019280 Heart failures Diseases 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 206010052337 Diastolic dysfunction Diseases 0.000 claims description 6
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 6
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 208000007536 Thrombosis Diseases 0.000 claims description 6
- 239000000674 adrenergic antagonist Substances 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 230000000747 cardiac effect Effects 0.000 claims description 6
- 208000020832 chronic kidney disease Diseases 0.000 claims description 6
- 230000007882 cirrhosis Effects 0.000 claims description 6
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 6
- 230000004064 dysfunction Effects 0.000 claims description 6
- 230000008694 endothelial dysfunction Effects 0.000 claims description 6
- 201000001881 impotence Diseases 0.000 claims description 6
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 6
- 208000010125 myocardial infarction Diseases 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 206010020852 Hypertonia Diseases 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000005541 ACE inhibitor Substances 0.000 claims description 4
- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 claims description 4
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 4
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 4
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 4
- 208000011514 Familial renal glucosuria Diseases 0.000 claims description 4
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims description 4
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 4
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims description 4
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 239000002170 aldosterone antagonist Substances 0.000 claims description 4
- 229940083712 aldosterone antagonist Drugs 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 4
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims description 4
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
- 239000002876 beta blocker Substances 0.000 claims description 4
- 239000000480 calcium channel blocker Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000002934 diuretic Substances 0.000 claims description 4
- 230000001882 diuretic effect Effects 0.000 claims description 4
- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 4
- 239000002792 enkephalinase inhibitor Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000002503 metabolic effect Effects 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 239000000810 peripheral vasodilating agent Substances 0.000 claims description 4
- 229960002116 peripheral vasodilator Drugs 0.000 claims description 4
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 4
- 239000004036 potassium channel stimulating agent Substances 0.000 claims description 4
- 208000007278 renal glycosuria Diseases 0.000 claims description 4
- 239000002461 renin inhibitor Substances 0.000 claims description 4
- 229940086526 renin-inhibitors Drugs 0.000 claims description 4
- 230000002889 sympathetic effect Effects 0.000 claims description 4
- 229940124549 vasodilator Drugs 0.000 claims description 4
- 239000003071 vasodilator agent Substances 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 3
- LXAOHLADQYQDKZ-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(3,4-difluorophenyl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=CC(=C(C=C1)F)F)=O)O)N=CN=2 LXAOHLADQYQDKZ-UHFFFAOYSA-N 0.000 claims description 2
- DGRJGTKRMXRNLZ-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(3-fluorophenyl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=CC(=CC=C1)F)=O)O)N=CN=2 DGRJGTKRMXRNLZ-UHFFFAOYSA-N 0.000 claims description 2
- MJPGVZAWISUCPN-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(4-chloro-3-fluorophenyl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=CC(=C(C=C1)Cl)F)=O)O)N=CN=2 MJPGVZAWISUCPN-UHFFFAOYSA-N 0.000 claims description 2
- FQESNKDMJREXNR-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(4-chlorophenyl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=CC=C(C=C1)Cl)=O)O)N=CN=2 FQESNKDMJREXNR-UHFFFAOYSA-N 0.000 claims description 2
- HQVUQJDUKZCAKM-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(4-fluorophenyl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=CC=C(C=C1)F)=O)O)N=CN=2 HQVUQJDUKZCAKM-UHFFFAOYSA-N 0.000 claims description 2
- IRJDCCOPVWQZFS-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-chloropyridin-2-yl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=NC=C(C=C1)Cl)=O)O)N=CN=2 IRJDCCOPVWQZFS-UHFFFAOYSA-N 0.000 claims description 2
- BJTDMLIJOGMFAB-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-fluoropyridin-2-yl)-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C)C1=NC=C(C=C1)F)=O)O)N=CN=2 BJTDMLIJOGMFAB-UHFFFAOYSA-N 0.000 claims description 2
- TXAOYIUUKRNHIX-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-methyl-5-(5-methylpyridin-2-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C1=NC=C(C=C1)C)C)=O)O)N=CN=2 TXAOYIUUKRNHIX-UHFFFAOYSA-N 0.000 claims description 2
- NVAZGOBZBPOMHJ-UHFFFAOYSA-N 2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C(CCC)C=1C=2N(C=C(N=1)C=1N=C(C3=C(N=1)NC(C3(C1=NC=C(C=C1)C(F)(F)F)C)=O)O)N=CN=2 NVAZGOBZBPOMHJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- LMRDQTUJMDYOSF-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(3,4-difluorophenyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C)C1=CC(=C(C=C1)F)F)=O LMRDQTUJMDYOSF-UHFFFAOYSA-N 0.000 claims description 2
- SMADCKIYUKQHTM-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(4-chloro-3-fluorophenyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C)C1=CC(=C(C=C1)Cl)F)=O SMADCKIYUKQHTM-UHFFFAOYSA-N 0.000 claims description 2
- QKSIYKIUIRBJLO-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(4-chlorophenyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C)C1=CC=C(C=C1)Cl)=O QKSIYKIUIRBJLO-UHFFFAOYSA-N 0.000 claims description 2
- RPLJYXSNLLLWJB-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(4-fluorophenyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C)C1=CC=C(C=C1)F)=O RPLJYXSNLLLWJB-UHFFFAOYSA-N 0.000 claims description 2
- DKJKIOMNQFKWRU-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-chloropyridin-2-yl)-5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1CC1)C1=NC=C(C=C1)Cl)=O DKJKIOMNQFKWRU-UHFFFAOYSA-N 0.000 claims description 2
- AYDTWTCFOONFAW-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-chloropyridin-2-yl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C)C1=NC=C(C=C1)Cl)=O AYDTWTCFOONFAW-UHFFFAOYSA-N 0.000 claims description 2
- BYZFKKBSQNZUHA-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-fluoropyridin-2-yl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C)C1=NC=C(C=C1)F)=O BYZFKKBSQNZUHA-UHFFFAOYSA-N 0.000 claims description 2
- TZNMGNJFFQFDSN-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-cyclopropyl-5-(5-methylpyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=NC=C(C=C1)C)C1CC1)=O TZNMGNJFFQFDSN-UHFFFAOYSA-N 0.000 claims description 2
- ARPIPJLVHMRNTM-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-cyclopropyl-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C=1OC(=NN=1)C(F)(F)F)C1CC1)=O ARPIPJLVHMRNTM-UHFFFAOYSA-N 0.000 claims description 2
- CFXHGGPGIWUSMF-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-cyclopropyl-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C1CC1)=O CFXHGGPGIWUSMF-UHFFFAOYSA-N 0.000 claims description 2
- SQPXVCJKVFWNAT-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-cyclopropyl-5-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=NC=CC=C1)C1CC1)=O SQPXVCJKVFWNAT-UHFFFAOYSA-N 0.000 claims description 2
- IBLMKKUNVUEJPK-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-methyl-5-(5-methylpyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=NC=C(C=C1)C)C)=O IBLMKKUNVUEJPK-UHFFFAOYSA-N 0.000 claims description 2
- WKZLLIKBYCBIRD-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-methyl-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C=1OC(=NN=1)C(F)(F)F)C)=O WKZLLIKBYCBIRD-UHFFFAOYSA-N 0.000 claims description 2
- GDSOLFAUGQUSPO-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C)=O GDSOLFAUGQUSPO-UHFFFAOYSA-N 0.000 claims description 2
- FUIAWYATXWPXHA-UHFFFAOYSA-N 4-amino-5-(3,4-difluorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C)C1=CC(=C(C=C1)F)F)=O FUIAWYATXWPXHA-UHFFFAOYSA-N 0.000 claims description 2
- UXFLSGRTDQWADO-UHFFFAOYSA-N 4-amino-5-(3,4-difluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=CC(=C(C=C1)F)F)=O UXFLSGRTDQWADO-UHFFFAOYSA-N 0.000 claims description 2
- DPINFZKMEZBXOX-UHFFFAOYSA-N 4-amino-5-(3-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=CC(=CC=C1)F)=O DPINFZKMEZBXOX-UHFFFAOYSA-N 0.000 claims description 2
- NCRWABGVHDOFSY-UHFFFAOYSA-N 4-amino-5-(4-chloro-3-fluorophenyl)-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1CC1)C1=CC(=C(C=C1)Cl)F)=O NCRWABGVHDOFSY-UHFFFAOYSA-N 0.000 claims description 2
- ILAXOCFPUSBEAT-UHFFFAOYSA-N 4-amino-5-(4-chloro-3-fluorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C)C1=CC(=C(C=C1)Cl)F)=O ILAXOCFPUSBEAT-UHFFFAOYSA-N 0.000 claims description 2
- JYDSMTRMKOUTQS-UHFFFAOYSA-N 4-amino-5-(4-chloro-3-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=CC(=C(C=C1)Cl)F)=O JYDSMTRMKOUTQS-UHFFFAOYSA-N 0.000 claims description 2
- FQFPGEPRBPWOPZ-UHFFFAOYSA-N 4-amino-5-(4-chloro-3-fluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=CC(=C(C=C1)Cl)F)=O FQFPGEPRBPWOPZ-UHFFFAOYSA-N 0.000 claims description 2
- IYELZELRRUTSRM-UHFFFAOYSA-N 4-amino-5-(4-chlorophenyl)-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1CC1)C1=CC=C(C=C1)Cl)=O IYELZELRRUTSRM-UHFFFAOYSA-N 0.000 claims description 2
- WGIHAFPDROKWSX-UHFFFAOYSA-N 4-amino-5-(4-chlorophenyl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C)C1=CC=C(C=C1)Cl)=O WGIHAFPDROKWSX-UHFFFAOYSA-N 0.000 claims description 2
- NDUOXCAEGKOONQ-UHFFFAOYSA-N 4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C)C1=CC=C(C=C1)Cl)=O NDUOXCAEGKOONQ-UHFFFAOYSA-N 0.000 claims description 2
- VCHOMOPTXOUEGA-UHFFFAOYSA-N 4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=CC=C(C=C1)Cl)=O VCHOMOPTXOUEGA-UHFFFAOYSA-N 0.000 claims description 2
- CRBYPVKGLITJSM-UHFFFAOYSA-N 4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=CC=C(C=C1)Cl)=O CRBYPVKGLITJSM-UHFFFAOYSA-N 0.000 claims description 2
- DNHSGSFOYNRUGB-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-2-[8-[(3-hydroxyphenyl)methyl]-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CC1=CC(=CC=C1)O)NC(C2(C)C1=CC=C(C=C1)F)=O DNHSGSFOYNRUGB-UHFFFAOYSA-N 0.000 claims description 2
- DXRSOXNGZMNAEL-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-2-[8-[(3-methoxyphenyl)methyl]-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CC1=CC(=CC=C1)OC)NC(C2(C)C1=CC=C(C=C1)F)=O DXRSOXNGZMNAEL-UHFFFAOYSA-N 0.000 claims description 2
- SVGKONLUXXYSDL-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-2-[8-[(4-fluorophenyl)methyl]-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CC1=CC=C(C=C1)F)NC(C2(C)C1=CC=C(C=C1)F)=O SVGKONLUXXYSDL-UHFFFAOYSA-N 0.000 claims description 2
- IYYOKZKDGWDNSR-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C)C1=CC=C(C=C1)F)=O IYYOKZKDGWDNSR-UHFFFAOYSA-N 0.000 claims description 2
- ZVOJZWYYPZJKMF-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(2-methylpropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CC(C)C)NC(C2(C)C1=CC=C(C=C1)F)=O ZVOJZWYYPZJKMF-UHFFFAOYSA-N 0.000 claims description 2
- HUKLGQVMRPFACU-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C)C1=CC=C(C=C1)F)=O HUKLGQVMRPFACU-UHFFFAOYSA-N 0.000 claims description 2
- MGCUKPRMLIXYBY-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=CC=C(C=C1)F)=O MGCUKPRMLIXYBY-UHFFFAOYSA-N 0.000 claims description 2
- CQLKLARDQREQRQ-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=CC=C(C=C1)F)=O CQLKLARDQREQRQ-UHFFFAOYSA-N 0.000 claims description 2
- USCPQVQKQOPVOT-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-cyclopropyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C1CC1)C1=NC=C(C=C1)Cl)=O USCPQVQKQOPVOT-UHFFFAOYSA-N 0.000 claims description 2
- GMEBMHXLCRVCDL-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-cyclopropyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C1CC1)C1=NC=C(C=C1)Cl)=O GMEBMHXLCRVCDL-UHFFFAOYSA-N 0.000 claims description 2
- LAELRCHSNCTPJT-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-cyclopropyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1CC1)C1=NC=C(C=C1)Cl)=O LAELRCHSNCTPJT-UHFFFAOYSA-N 0.000 claims description 2
- HLXPYMUSAFZNAF-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1CC1)C1=NC=C(C=C1)Cl)=O HLXPYMUSAFZNAF-UHFFFAOYSA-N 0.000 claims description 2
- MZIXUNMCTVYUOH-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)Cl)=O MZIXUNMCTVYUOH-UHFFFAOYSA-N 0.000 claims description 2
- TWEAKVSWDSWQBJ-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=NC=C(C=C1)Cl)=O TWEAKVSWDSWQBJ-UHFFFAOYSA-N 0.000 claims description 2
- XMYVQHFFWOGGMA-UHFFFAOYSA-N 4-amino-5-(5-chloropyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)Cl)=O XMYVQHFFWOGGMA-UHFFFAOYSA-N 0.000 claims description 2
- PLDWBQCIJIWSGW-UHFFFAOYSA-N 4-amino-5-(5-chloropyrimidin-2-yl)-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1CC1)C1=NC=C(C=N1)Cl)=O PLDWBQCIJIWSGW-UHFFFAOYSA-N 0.000 claims description 2
- RORZLIFFXJHOTM-UHFFFAOYSA-N 4-amino-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C=1OC(=NN=1)C1CC1)=O RORZLIFFXJHOTM-UHFFFAOYSA-N 0.000 claims description 2
- ZTRBJGVTFSWFHO-UHFFFAOYSA-N 4-amino-5-(5-fluoropyridin-2-yl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C)C1=NC=C(C=C1)F)=O ZTRBJGVTFSWFHO-UHFFFAOYSA-N 0.000 claims description 2
- KWOUQRODWWUDFA-UHFFFAOYSA-N 4-amino-5-(5-fluoropyridin-2-yl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)F)=O KWOUQRODWWUDFA-UHFFFAOYSA-N 0.000 claims description 2
- VAEQWDRGIKNKKS-UHFFFAOYSA-N 4-amino-5-(5-fluoropyridin-2-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=NC=C(C=C1)F)=O VAEQWDRGIKNKKS-UHFFFAOYSA-N 0.000 claims description 2
- VWQLPDQCMBHHSS-UHFFFAOYSA-N 4-amino-5-(5-fluoropyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)F)=O VWQLPDQCMBHHSS-UHFFFAOYSA-N 0.000 claims description 2
- SHFRQEFCNIPPLT-UHFFFAOYSA-N 4-amino-5-(5-fluoropyridin-3-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C=1C=NC=C(C=1)F)=O SHFRQEFCNIPPLT-UHFFFAOYSA-N 0.000 claims description 2
- IFJCGHBLZJDHAR-UHFFFAOYSA-N 4-amino-5-(5-hydroxypyridin-2-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=NC=C(C=C1)O)=O IFJCGHBLZJDHAR-UHFFFAOYSA-N 0.000 claims description 2
- BHSFYGHVINOUOL-UHFFFAOYSA-N 4-amino-5-(5-hydroxypyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)O)=O BHSFYGHVINOUOL-UHFFFAOYSA-N 0.000 claims description 2
- ZEYPXJBGPKEDQQ-UHFFFAOYSA-N 4-amino-5-(5-methoxypyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)OC)=O ZEYPXJBGPKEDQQ-UHFFFAOYSA-N 0.000 claims description 2
- RVMPPSLJQUDFMZ-UHFFFAOYSA-N 4-amino-5-(6-cyclopropylpyridin-3-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C=1C=NC(=CC=1)C1CC1)=O RVMPPSLJQUDFMZ-UHFFFAOYSA-N 0.000 claims description 2
- DGEWSXUGPVTVRX-UHFFFAOYSA-N 4-amino-5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C=1OC(=NN=1)C(F)F)=O DGEWSXUGPVTVRX-UHFFFAOYSA-N 0.000 claims description 2
- VJIXNODGCBZXAZ-UHFFFAOYSA-N 4-amino-5-[6-(1,1-difluoroethyl)pyridin-3-yl]-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C=1C=NC(=CC=1)C(C)(F)F)=O VJIXNODGCBZXAZ-UHFFFAOYSA-N 0.000 claims description 2
- SGDXPIZSAOAEGS-UHFFFAOYSA-N 4-amino-5-[6-(1,1-difluoroethyl)pyridin-3-yl]-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C=1C=NC(=CC=1)C(C)(F)F)=O SGDXPIZSAOAEGS-UHFFFAOYSA-N 0.000 claims description 2
- UDKBGNHZFUMFSW-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C1CC1)=O UDKBGNHZFUMFSW-UHFFFAOYSA-N 0.000 claims description 2
- DWPKLHAHQVIOGN-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C1CC1)=O DWPKLHAHQVIOGN-UHFFFAOYSA-N 0.000 claims description 2
- LBYFGSUCUDWNPM-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=CC=C1)C1CC1)=O LBYFGSUCUDWNPM-UHFFFAOYSA-N 0.000 claims description 2
- STJVSZIVMJVSAU-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[4-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC=C(C=C1)C(F)(F)F)C1CC1)=O STJVSZIVMJVSAU-UHFFFAOYSA-N 0.000 claims description 2
- HLNJUOKYJJEMME-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C=1OC(=NN=1)C(F)(F)F)C1CC1)=O HLNJUOKYJJEMME-UHFFFAOYSA-N 0.000 claims description 2
- XMRXUIDAWODQQT-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C1CC1)=O XMRXUIDAWODQQT-UHFFFAOYSA-N 0.000 claims description 2
- NXTJAESHJIRCED-UHFFFAOYSA-N 4-amino-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyrimidin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=N1)C(F)(F)F)C1CC1)=O NXTJAESHJIRCED-UHFFFAOYSA-N 0.000 claims description 2
- CAIUNFCQTGOBEW-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(1-cyclopropyltriazol-4-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C=1N=NN(C=1)C1CC1)C1CC1)=O CAIUNFCQTGOBEW-UHFFFAOYSA-N 0.000 claims description 2
- CKTKGBXOLMFEIA-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(3,4-difluorophenyl)-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C1=CC(=C(C=C1)F)F)C1CC1)=O CKTKGBXOLMFEIA-UHFFFAOYSA-N 0.000 claims description 2
- AKCBHEFDOWJMBE-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(3,4-difluorophenyl)-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C1=CC(=C(C=C1)F)F)C1CC1)=O AKCBHEFDOWJMBE-UHFFFAOYSA-N 0.000 claims description 2
- OBPMXGOBTRMOQX-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(3,4-difluorophenyl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=CC(=C(C=C1)F)F)C1CC1)=O OBPMXGOBTRMOQX-UHFFFAOYSA-N 0.000 claims description 2
- VAPMPFHTGOYTKX-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(3,4-difluorophenyl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC(=C(C=C1)F)F)C1CC1)=O VAPMPFHTGOYTKX-UHFFFAOYSA-N 0.000 claims description 2
- HLRUZIKEMSSUDD-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(4-fluorophenyl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC=C(C=C1)F)C1CC1)=O HLRUZIKEMSSUDD-UHFFFAOYSA-N 0.000 claims description 2
- GVMVMZLPQNTYFX-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C=1OC(=NN=1)C1CC1)C1CC1)=O GVMVMZLPQNTYFX-UHFFFAOYSA-N 0.000 claims description 2
- NNCUDLVFZBWIPD-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C=1OC(=NN=1)C1CC1)C1CC1)=O NNCUDLVFZBWIPD-UHFFFAOYSA-N 0.000 claims description 2
- YWGLIMUDDCYNLB-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-fluoropyridin-2-yl)-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC)NC(C2(C1=NC=C(C=C1)F)C1CC1)=O YWGLIMUDDCYNLB-UHFFFAOYSA-N 0.000 claims description 2
- FWEBZICMYGMECR-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-fluoropyridin-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)F)C1CC1)=O FWEBZICMYGMECR-UHFFFAOYSA-N 0.000 claims description 2
- PGTGKLBIWILVAP-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-fluoropyridin-3-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C=1C=NC=C(C=1)F)C1CC1)=O PGTGKLBIWILVAP-UHFFFAOYSA-N 0.000 claims description 2
- CKEYVUUKZGJNEV-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-hydroxypyridin-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)O)C1CC1)=O CKEYVUUKZGJNEV-UHFFFAOYSA-N 0.000 claims description 2
- AVMSVDHMKIFGKX-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-methoxypyridin-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)OC)C1CC1)=O AVMSVDHMKIFGKX-UHFFFAOYSA-N 0.000 claims description 2
- YCSHDNZHOLZUCA-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-methylpyridin-2-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=C(C=C1)C)C1CC1)=O YCSHDNZHOLZUCA-UHFFFAOYSA-N 0.000 claims description 2
- JBCFREOWAKXADE-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-(5-methylpyridin-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C)C1CC1)=O JBCFREOWAKXADE-UHFFFAOYSA-N 0.000 claims description 2
- CCSJDJFJESBSTJ-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-[5-(difluoromethyl)pyridin-2-yl]-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C(F)F)C1CC1)=O CCSJDJFJESBSTJ-UHFFFAOYSA-N 0.000 claims description 2
- VVDQPSLLNVAGFQ-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-[5-(trifluoromethyl)pyridin-2-yl]-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C1CC1)=O VVDQPSLLNVAGFQ-UHFFFAOYSA-N 0.000 claims description 2
- MSBVNXUXJJQPIP-UHFFFAOYSA-N 4-amino-5-cyclopropyl-5-pyridin-2-yl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=CC=C1)C1CC1)=O MSBVNXUXJJQPIP-UHFFFAOYSA-N 0.000 claims description 2
- LXMPXFGBGZDHMP-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-(1-propan-2-yltriazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C=1N=NN(C=1)C(C)C)=O LXMPXFGBGZDHMP-UHFFFAOYSA-N 0.000 claims description 2
- VLYGQEBBZHYBMS-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=CC=CC=C1)C)=O VLYGQEBBZHYBMS-UHFFFAOYSA-N 0.000 claims description 2
- WJVBISFJDFEURV-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical group NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=CC=C1)C)=O WJVBISFJDFEURV-UHFFFAOYSA-N 0.000 claims description 2
- JALDDVDOPHQSGH-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[4-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC=C(C=C1)C(F)(F)F)C)=O JALDDVDOPHQSGH-UHFFFAOYSA-N 0.000 claims description 2
- WEDFAJGOXJKPEJ-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C=1OC(=NN=1)C(F)(F)F)C)=O WEDFAJGOXJKPEJ-UHFFFAOYSA-N 0.000 claims description 2
- VGILGXVLAPAJGV-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyrazin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(N=C1)C(F)(F)F)C)=O VGILGXVLAPAJGV-UHFFFAOYSA-N 0.000 claims description 2
- ZHHHROQVQDTTFE-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C)=O ZHHHROQVQDTTFE-UHFFFAOYSA-N 0.000 claims description 2
- FAOZTINVUCJCHW-UHFFFAOYSA-N 4-amino-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyrimidin-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=N1)C(F)(F)F)C)=O FAOZTINVUCJCHW-UHFFFAOYSA-N 0.000 claims description 2
- MCJFAXLHHDSEHB-UHFFFAOYSA-N 4-amino-5-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C=1OC(=NN=1)C)C)=O MCJFAXLHHDSEHB-UHFFFAOYSA-N 0.000 claims description 2
- XIKMBSYHZAJKPJ-UHFFFAOYSA-N 4-amino-5-methyl-5-(5-methylpyridin-2-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=C(C=C1)C)C)=O XIKMBSYHZAJKPJ-UHFFFAOYSA-N 0.000 claims description 2
- YGSCFPDMHZVONW-UHFFFAOYSA-N 4-amino-5-methyl-5-(5-methylpyridin-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C)C)=O YGSCFPDMHZVONW-UHFFFAOYSA-N 0.000 claims description 2
- ACPMVAXNGRTZLY-UHFFFAOYSA-N 4-amino-5-methyl-5-[4-(trifluoromethyl)phenyl]-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C1=CC=C(C=C1)C(F)(F)F)C)=O ACPMVAXNGRTZLY-UHFFFAOYSA-N 0.000 claims description 2
- MNDMDZWBVHYYCC-UHFFFAOYSA-N 4-amino-5-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C(F)(F)F)C)=O MNDMDZWBVHYYCC-UHFFFAOYSA-N 0.000 claims description 2
- PXLIOHPCMQJXTA-UHFFFAOYSA-N 4-amino-5-methyl-5-[6-methyl-5-(trifluoromethyl)pyridin-2-yl]-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC(=C(C=C1)C(F)(F)F)C)C)=O PXLIOHPCMQJXTA-UHFFFAOYSA-N 0.000 claims description 2
- WKDGLWSBKZRFFL-UHFFFAOYSA-N 4-amino-5-methyl-5-phenyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC=CC=C1)C)=O WKDGLWSBKZRFFL-UHFFFAOYSA-N 0.000 claims description 2
- VDZIFQUIIMCOSF-UHFFFAOYSA-N 4-amino-5-methyl-5-pyridin-2-yl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=CC=C1)C)=O VDZIFQUIIMCOSF-UHFFFAOYSA-N 0.000 claims description 2
- GWKFVOOOQUZTLX-UHFFFAOYSA-N 5-(2-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=C(C=CC=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C GWKFVOOOQUZTLX-UHFFFAOYSA-N 0.000 claims description 2
- FXMFNQXAHCFMFN-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC=1C=C(C=CC=1F)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C FXMFNQXAHCFMFN-UHFFFAOYSA-N 0.000 claims description 2
- QEMBQQYXGMHHDZ-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC=1C=C(C=CC=1F)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C QEMBQQYXGMHHDZ-UHFFFAOYSA-N 0.000 claims description 2
- UYOVMYULXQMQPB-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC=1C=C(C=CC=1F)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C UYOVMYULXQMQPB-UHFFFAOYSA-N 0.000 claims description 2
- ZIQMLBVGBHFJMI-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=C(C=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC)=O)C)F ZIQMLBVGBHFJMI-UHFFFAOYSA-N 0.000 claims description 2
- XTZHSOJLALOJRU-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-5-methyl-2-[2-methyl-8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=C(C=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=C(N=2)C)CCC(C(F)(F)F)(F)F)=O)C)F XTZHSOJLALOJRU-UHFFFAOYSA-N 0.000 claims description 2
- GHMMCRQPZIYZHH-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=C(C=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(F)(F)F)=O)C)F GHMMCRQPZIYZHH-UHFFFAOYSA-N 0.000 claims description 2
- BZDAFTAFNAUHAP-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=C(C=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C)F BZDAFTAFNAUHAP-UHFFFAOYSA-N 0.000 claims description 2
- VTFPIOAZLAOGIP-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=C(C=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C)F VTFPIOAZLAOGIP-UHFFFAOYSA-N 0.000 claims description 2
- RQUJHXXCTCPMEU-UHFFFAOYSA-N 5-(4-chlorophenyl)-5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C1CC1 RQUJHXXCTCPMEU-UHFFFAOYSA-N 0.000 claims description 2
- MZQAKUBUKLVBNB-UHFFFAOYSA-N 5-(4-chlorophenyl)-5-methyl-2-(2-methyl-8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=C(N=2)C)CCC)=O)C MZQAKUBUKLVBNB-UHFFFAOYSA-N 0.000 claims description 2
- NQXKGNSTRHZFOG-UHFFFAOYSA-N 5-(4-chlorophenyl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC)=O)C NQXKGNSTRHZFOG-UHFFFAOYSA-N 0.000 claims description 2
- XVTLVBPEBCUUPH-UHFFFAOYSA-N 5-(4-chlorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(F)(F)F)=O)C XVTLVBPEBCUUPH-UHFFFAOYSA-N 0.000 claims description 2
- XGSAUVJSUOHIQR-UHFFFAOYSA-N 5-(4-chlorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C XGSAUVJSUOHIQR-UHFFFAOYSA-N 0.000 claims description 2
- QIHQYKPCZFVCLW-UHFFFAOYSA-N 5-(4-chlorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C QIHQYKPCZFVCLW-UHFFFAOYSA-N 0.000 claims description 2
- QEXQJEDNFMNQHS-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-[8-[(4-fluorophenyl)methyl]-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(CC=2C=3N(C=C(N=2)C=2N=C(C4=C(N=2)NC(C4(C)C2=CC=C(C=C2)F)=O)O)N=CN=3)C=C1 QEXQJEDNFMNQHS-UHFFFAOYSA-N 0.000 claims description 2
- QZVDNDBVKIRAMV-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC)=O)C QZVDNDBVKIRAMV-UHFFFAOYSA-N 0.000 claims description 2
- JCAADJBKSUZCPW-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[2-methyl-8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=C(N=2)C)CCC(C(F)(F)F)(F)F)=O)C JCAADJBKSUZCPW-UHFFFAOYSA-N 0.000 claims description 2
- RVWDIFMQHHMXAP-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[8-(2-methylpropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CC(C)C)=O)C RVWDIFMQHHMXAP-UHFFFAOYSA-N 0.000 claims description 2
- IAJVJHRGFMNGET-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[8-(2-methylpropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=CC=21)C=1N=C(C=2N(C=1)N=CN=2)CC(C)C)=O)C IAJVJHRGFMNGET-UHFFFAOYSA-N 0.000 claims description 2
- LNRXFHPGMNHSDF-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[8-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(F)(F)F)=O)C LNRXFHPGMNHSDF-UHFFFAOYSA-N 0.000 claims description 2
- GHHUNCRUKHYJBG-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C GHHUNCRUKHYJBG-UHFFFAOYSA-N 0.000 claims description 2
- FNQWGAJWOVJUBS-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=CC=21)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C FNQWGAJWOVJUBS-UHFFFAOYSA-N 0.000 claims description 2
- QMEGLEOBAWUJPM-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C QMEGLEOBAWUJPM-UHFFFAOYSA-N 0.000 claims description 2
- QOJYZXIZHRERGR-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-6-oxo-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidine-4-carboxamide Chemical compound FC1=CC=C(C=C1)C1(C(NC=2N=C(N=C(C=21)C(=O)N)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C QOJYZXIZHRERGR-UHFFFAOYSA-N 0.000 claims description 2
- HTSWBHXYYZTKOR-UHFFFAOYSA-N 5-(5-chloropyridin-2-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC=1C=CC(=NC=1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C HTSWBHXYYZTKOR-UHFFFAOYSA-N 0.000 claims description 2
- HDQSTMUOYLADDU-UHFFFAOYSA-N 5-(5-chloropyridin-2-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound ClC=1C=CC(=NC=1)C1(C(NC=2N=C(N=CC=21)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C HDQSTMUOYLADDU-UHFFFAOYSA-N 0.000 claims description 2
- NDBRZJKOQUYAFM-UHFFFAOYSA-N 5-(5-chloropyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound ClC=1C=CC(=NC=1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C NDBRZJKOQUYAFM-UHFFFAOYSA-N 0.000 claims description 2
- FQIDCQHKAQGVCE-UHFFFAOYSA-N 5-(5-fluoropyridin-2-yl)-5-methyl-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC=1C=CC(=NC=1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC)=O)C FQIDCQHKAQGVCE-UHFFFAOYSA-N 0.000 claims description 2
- RNLZSTFDCDPUOM-UHFFFAOYSA-N 5-(5-fluoropyridin-2-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC=1C=CC(=NC=1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C RNLZSTFDCDPUOM-UHFFFAOYSA-N 0.000 claims description 2
- SZKWCPXSXXZGBM-UHFFFAOYSA-N 5-(5-fluoropyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC=1C=CC(=NC=1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C SZKWCPXSXXZGBM-UHFFFAOYSA-N 0.000 claims description 2
- IRAXKEOTEXTBIZ-UHFFFAOYSA-N 5-(5-fluoropyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound FC=1C=CC(=NC=1)C1(C(NC=2N=C(N=CC=21)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C IRAXKEOTEXTBIZ-UHFFFAOYSA-N 0.000 claims description 2
- XIGIDVSPIFXCAQ-UHFFFAOYSA-N 5-(5-fluoropyridin-3-yl)-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound FC=1C=C(C=NC=1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C XIGIDVSPIFXCAQ-UHFFFAOYSA-N 0.000 claims description 2
- FLSGGECKLJAXPI-UHFFFAOYSA-N 5-(5-methoxypyridin-2-yl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)OC)=O FLSGGECKLJAXPI-UHFFFAOYSA-N 0.000 claims description 2
- GMFPXEDWXYMGSS-UHFFFAOYSA-N 5-cyclopropyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[4-(trifluoromethyl)phenyl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C1=CC=C(C=C1)C(F)(F)F GMFPXEDWXYMGSS-UHFFFAOYSA-N 0.000 claims description 2
- ZQPNNJBLYIUGRQ-UHFFFAOYSA-N 5-cyclopropyl-5-(3,4-difluorophenyl)-2-(8-propyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC)=O)C1=CC(=C(C=C1)F)F ZQPNNJBLYIUGRQ-UHFFFAOYSA-N 0.000 claims description 2
- RRHBOVMYQSORJM-UHFFFAOYSA-N 5-cyclopropyl-5-(3,4-difluorophenyl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C1=CC(=C(C=C1)F)F RRHBOVMYQSORJM-UHFFFAOYSA-N 0.000 claims description 2
- AWYLFKHLOUQDCJ-UHFFFAOYSA-N 5-cyclopropyl-5-(3,4-difluorophenyl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C1=CC(=C(C=C1)F)F AWYLFKHLOUQDCJ-UHFFFAOYSA-N 0.000 claims description 2
- UKWGKGCNJFZTMQ-UHFFFAOYSA-N 5-cyclopropyl-5-(4-fluorophenyl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C1=CC=C(C=C1)F UKWGKGCNJFZTMQ-UHFFFAOYSA-N 0.000 claims description 2
- ZBVSGZUWUCYQDO-UHFFFAOYSA-N 5-cyclopropyl-5-(5-fluoropyridin-3-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)O)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C=1C=NC=C(C=1)F ZBVSGZUWUCYQDO-UHFFFAOYSA-N 0.000 claims description 2
- POEYPFCJUOEHDS-UHFFFAOYSA-N 5-cyclopropyl-6-oxo-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-4-carboxamide Chemical compound C1(CC1)C1(C(NC=2N=C(N=C(C=21)C(=O)N)C=1N=C(C=2N(C=1)N=CN=2)CCC(C(F)(F)F)(F)F)=O)C1=NC=C(C=C1)C(F)(F)F POEYPFCJUOEHDS-UHFFFAOYSA-N 0.000 claims description 2
- FTURIAOICMDDDE-UHFFFAOYSA-N 5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-phenyl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=CC=CC=C1)C)=O FTURIAOICMDDDE-UHFFFAOYSA-N 0.000 claims description 2
- YZBBCEWESBXZLS-UHFFFAOYSA-N 5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-pyridin-2-yl-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=CC=C1)C)=O YZBBCEWESBXZLS-UHFFFAOYSA-N 0.000 claims description 2
- MMJJLMSPEWYVPY-UHFFFAOYSA-N 5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[4-(trifluoromethyl)phenyl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC=C(C=C1)C(F)(F)F)C)=O MMJJLMSPEWYVPY-UHFFFAOYSA-N 0.000 claims description 2
- WQUUWICGCVWZDN-UHFFFAOYSA-N 5-methyl-5-(5-methylpyridin-2-yl)-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1=NC=C(C=C1)C)C)=O WQUUWICGCVWZDN-UHFFFAOYSA-N 0.000 claims description 2
- AJOUZKWYHOFUBD-UHFFFAOYSA-N 5-methyl-5-(5-methylpyridin-2-yl)-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=C(C=C1)C)C)=O AJOUZKWYHOFUBD-UHFFFAOYSA-N 0.000 claims description 2
- MRIWGONMCZZCCX-UHFFFAOYSA-N 5-methyl-5-phenyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=CC=CC=C1)C)=O MRIWGONMCZZCCX-UHFFFAOYSA-N 0.000 claims description 2
- AUAGWZLHYJPYQO-UHFFFAOYSA-N 5-methyl-5-pyridin-2-yl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidine-4,6-dione Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1=NC=CC=C1)C)=O AUAGWZLHYJPYQO-UHFFFAOYSA-N 0.000 claims description 2
- FJQBCLXGEBWTQJ-UHFFFAOYSA-N 5-methyl-6-oxo-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-[5-(trifluoromethyl)pyridin-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-4-carboxamide Chemical compound CC1(C(NC=2N=C(N=C(C=21)C(=O)N)C=1N=C(C=2N(C=1)N=CN=2)CCCC(F)(F)F)=O)C1=NC=C(C=C1)C(F)(F)F FJQBCLXGEBWTQJ-UHFFFAOYSA-N 0.000 claims description 2
- YJWGDEYTAGQDLX-UHFFFAOYSA-N 6-[4-amino-5-cyclopropyl-6-oxo-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-3-carbonitrile Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C1CC1)C1=NC=C(C#N)C=C1)=O YJWGDEYTAGQDLX-UHFFFAOYSA-N 0.000 claims description 2
- ZZXQFRLDCWLXSC-UHFFFAOYSA-N 6-[4-amino-5-cyclopropyl-6-oxo-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-3-carbonitrile Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C1CC1)C1=NC=C(C#N)C=C1)=O ZZXQFRLDCWLXSC-UHFFFAOYSA-N 0.000 claims description 2
- UCYYTBUUTZUGSL-UHFFFAOYSA-N 6-[4-amino-5-methyl-6-oxo-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-3-carbonitrile Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=NC=C(C#N)C=C1)=O UCYYTBUUTZUGSL-UHFFFAOYSA-N 0.000 claims description 2
- RDUDGTAYTMYFEF-UHFFFAOYSA-N 6-[4-amino-5-methyl-6-oxo-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-3-carbonitrile Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C#N)C=C1)=O RDUDGTAYTMYFEF-UHFFFAOYSA-N 0.000 claims description 2
- LBVPDJBIFFOYKB-UHFFFAOYSA-N 6-[5-methyl-4,6-dioxo-2-[8-(3,3,4,4,4-pentafluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl]pyridine-3-carbonitrile Chemical compound OC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCC(C(F)(F)F)(F)F)NC(C2(C)C1=NC=C(C#N)C=C1)=O LBVPDJBIFFOYKB-UHFFFAOYSA-N 0.000 claims description 2
- XDDXRBZGDMREBJ-UHFFFAOYSA-N O=C(C1)NC2=C1C=NC(C1=CN3N=CN=C3C(CCC(F)(F)F)=N1)=N2 Chemical compound O=C(C1)NC2=C1C=NC(C1=CN3N=CN=C3C(CCC(F)(F)F)=N1)=N2 XDDXRBZGDMREBJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 239000003524 antilipemic agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
- BBCDREPRFLMMHC-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-cyclopropyl-5-(5-fluoropyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=NC=C(C=C1)F)C1CC1)=O BBCDREPRFLMMHC-UHFFFAOYSA-N 0.000 claims 1
- ZPHZAYGQQFNLLE-UHFFFAOYSA-N 4-amino-5-[5-(difluoromethyl)pyridin-2-yl]-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=NC=C(C=C1)C(F)F)=O ZPHZAYGQQFNLLE-UHFFFAOYSA-N 0.000 claims 1
- OEVSBRPRPGIELY-UHFFFAOYSA-N 4-amino-2-(8-butyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-cyclopropyl-5-(3,4-difluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC)NC(C2(C1=CC(=C(C=C1)F)F)C1CC1)=O OEVSBRPRPGIELY-UHFFFAOYSA-N 0.000 description 1
- HRFHQESZAJMGCE-UHFFFAOYSA-N 4-amino-5-(3-chloro-4-fluorophenyl)-5-methyl-2-[8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=CN=3)CCCC(F)(F)F)NC(C2(C)C1=CC(=C(C=C1)F)Cl)=O HRFHQESZAJMGCE-UHFFFAOYSA-N 0.000 description 1
- HPOHRFACRZAJPT-UHFFFAOYSA-N 4-amino-5-(4-fluorophenyl)-2-[8-[(4-fluorophenyl)methyl]-2-methyl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-one Chemical compound NC=1C2=C(N=C(N=1)C=1N=C(C=3N(C=1)N=C(N=3)C)CC1=CC=C(C=C1)F)NC(C2(C)C1=CC=C(C=C1)F)=O HPOHRFACRZAJPT-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1n[n](cc(-c2nc(*)c(C(*)C(N3)=O)c3n2)nc2*)c2n1 Chemical compound Cc1n[n](cc(-c2nc(*)c(C(*)C(N3)=O)c3n2)nc2*)c2n1 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462082686P | 2014-11-21 | 2014-11-21 | |
| US62/082,686 | 2014-11-21 | ||
| US201562144697P | 2015-04-08 | 2015-04-08 | |
| US62/144,697 | 2015-04-08 | ||
| PCT/US2015/061442 WO2016081668A1 (en) | 2014-11-21 | 2015-11-19 | Triazolo-pyrazinyl derivatives useful as soluble guanylate cyclase activators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017535561A JP2017535561A (ja) | 2017-11-30 |
| JP2017535561A5 true JP2017535561A5 (OSRAM) | 2019-01-10 |
Family
ID=54704159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017526957A Withdrawn JP2017535561A (ja) | 2014-11-21 | 2015-11-19 | 可溶性グアニル酸シクラーゼ活性化剤として有用なトリアゾロ−ピラジニル誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9822130B2 (OSRAM) |
| EP (1) | EP3221319B1 (OSRAM) |
| JP (1) | JP2017535561A (OSRAM) |
| KR (1) | KR20170084299A (OSRAM) |
| CN (1) | CN107001389A (OSRAM) |
| AU (1) | AU2015349888A1 (OSRAM) |
| BR (1) | BR112017010551A2 (OSRAM) |
| CA (1) | CA2967965A1 (OSRAM) |
| MX (1) | MX2017006649A (OSRAM) |
| RU (1) | RU2017121278A (OSRAM) |
| TW (1) | TW201625635A (OSRAM) |
| WO (1) | WO2016081668A1 (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015088885A1 (en) | 2013-12-11 | 2015-06-18 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| EP3079700B1 (en) | 2013-12-11 | 2020-11-25 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| EP3152214B1 (en) | 2014-06-04 | 2020-01-29 | Merck Sharp & Dohme Corp. | Imidazo-pyrazine derivatives useful as soluble guanylate cyclase activators |
| EP3186251A1 (de) * | 2014-08-29 | 2017-07-05 | Bayer Pharma Aktiengesellschaft | Substituierte annellierte pyrimidine und ihre verwendung |
| US10245264B2 (en) | 2015-05-27 | 2019-04-02 | Merck Sharp & Dohme Corp. | Substituted imidazo[1,2-a]pyrazines as soluble guanylate cyclase activators |
| US10213429B2 (en) | 2015-05-28 | 2019-02-26 | Merck Sharp & Dohme Corp. | Imidazo-pyrazinyl derivatives useful as soluble guanylate cyclase activators |
| WO2017107052A1 (en) | 2015-12-22 | 2017-06-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase stimulators |
| WO2017197555A1 (en) * | 2016-05-16 | 2017-11-23 | Merck Sharp & Dohme Corp. | Fused pyrazine derivatives useful as soluble guanylate cyclase stimulators |
| EP3458063A4 (en) * | 2016-05-18 | 2020-02-26 | Merck Sharp & Dohme Corp. | METHOD FOR USE OF TRIAZOLO-PYRAZINYL-SOLUBLE GUANYLATE CYCLASE ACTIVATORS IN FIBROTIC DISEASES |
| CN105968055B (zh) * | 2016-07-26 | 2018-08-28 | 中国科学院长春应用化学研究所 | 一种芳基嘧啶及其衍生物的制备方法 |
| IL292968B2 (en) * | 2016-09-02 | 2025-10-01 | Cyclerion Therapeutics Inc | SCG racers merge on bicycles |
| WO2018069148A1 (de) | 2016-10-11 | 2018-04-19 | Bayer Pharma Aktiengesellschaft | Kombination enthaltend sgc aktivatoren und mineralocorticoid-rezeptor-antagonisten |
| ES2985316T3 (es) | 2016-10-11 | 2024-11-05 | Bayer Pharma AG | Combinación que contiene el estimulador sGC vericuguat y el antagonista de los receptores de corticoides minerales finerenona |
| WO2019081456A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Aktiengesellschaft | USE OF SGC ACTIVATORS AND STIMULATORS COMPRISING A BETA2 SUBUNIT |
| EP3498298A1 (en) | 2017-12-15 | 2019-06-19 | Bayer AG | The use of sgc stimulators and sgc activators alone or in combination with pde5 inhibitors for the treatment of bone disorders including osteogenesis imperfecta (oi) |
| MX2020006433A (es) * | 2017-12-19 | 2020-09-17 | Cyclerion Therapeutics Inc | Estimuladores de guanilato ciclasa soluble (sgc). |
| JP7314173B2 (ja) | 2018-04-30 | 2023-07-25 | バイエル アクチェンゲゼルシャフト | 認知障害の治療のためのｓＧＣ活性化薬及びｓＧＣ刺激薬の使用 |
| KR20210008070A (ko) | 2018-05-15 | 2021-01-20 | 바이엘 악티엔게젤샤프트 | 신경 섬유 감작과 연관된 질환의 치료를 위한 1,3-티아졸-2-일 치환된 벤즈아미드 |
| EP3574905A1 (en) | 2018-05-30 | 2019-12-04 | Adverio Pharma GmbH | Method of identifying a subgroup of patients suffering from dcssc which benefits from a treatment with sgc stimulators and sgc activators in a higher degree than a control group |
| CA3126778A1 (en) | 2019-01-17 | 2020-07-23 | Bayer Aktiengesellschaft | Methods to determine whether a subject is suitable of being treated with an agonist of soluble guanylyl cyclase (sgc) |
| JP7663605B2 (ja) * | 2020-04-30 | 2025-04-16 | チア タイ ティエンチン ファーマシューティカル グループ カンパニー リミテッド | ピリミジン系三環式化合物及びその使用 |
| EP4326268A1 (en) | 2021-04-20 | 2024-02-28 | Tisento Therapeutics Inc. | Treatment of cns diseases with sgc stimulators |
| WO2022225903A1 (en) | 2021-04-20 | 2022-10-27 | Cyclerion Therapeutics, Inc. | Sgc stimulators |
| JP2025536344A (ja) | 2022-10-18 | 2025-11-05 | ティセント セラピューティクス インコーポレーテッド | ｓＧＣ刺激剤でのミトコンドリア疾患の処置 |
| CN116768868B (zh) * | 2023-08-15 | 2023-12-08 | 云南省药物研究所 | 一种哒嗪酮硫代衍生物及其制备方法和应用 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4845079A (en) | 1985-01-23 | 1989-07-04 | Luly Jay R | Peptidylaminodiols |
| US5066643A (en) | 1985-02-19 | 1991-11-19 | Sandoz Ltd. | Fluorine and chlorine statine or statone containing peptides and method of use |
| US4894437A (en) | 1985-11-15 | 1990-01-16 | The Upjohn Company | Novel renin inhibiting polypeptide analogs containing S-aryl-D- or L- or DL-cysteinyl, 3-(arylthio)lactic acid or 3-(arylthio)alkyl moieties |
| US4885292A (en) | 1986-02-03 | 1989-12-05 | E. R. Squibb & Sons, Inc. | N-heterocyclic alcohol renin inhibitors |
| US5089471A (en) | 1987-10-01 | 1992-02-18 | G. D. Searle & Co. | Peptidyl beta-aminoacyl aminodiol carbamates as anti-hypertensive agents |
| US4980283A (en) | 1987-10-01 | 1990-12-25 | Merck & Co., Inc. | Renin-inhibitory pepstatin phenyl derivatives |
| US5034512A (en) | 1987-10-22 | 1991-07-23 | Warner-Lambert Company | Branched backbone renin inhibitors |
| US5063207A (en) | 1987-10-26 | 1991-11-05 | Warner-Lambert Company | Renin inhibitors, method for using them, and compositions containing them |
| US5055466A (en) | 1987-11-23 | 1991-10-08 | E. R. Squibb & Sons, Inc. | N-morpholino derivatives and their use as anti-hypertensive agents |
| US5036054A (en) | 1988-02-11 | 1991-07-30 | Warner-Lambert Company | Renin inhibitors containing alpha-heteroatom amino acids |
| US5036053A (en) | 1988-05-27 | 1991-07-30 | Warner-Lambert Company | Diol-containing renin inhibitors |
| DE3841520A1 (de) | 1988-12-09 | 1990-06-13 | Hoechst Ag | Enzymhemmende harnstoffderivate von dipeptiden, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung |
| US5106835A (en) | 1988-12-27 | 1992-04-21 | American Cyanamid Company | Renin inhibitors |
| US5063208A (en) | 1989-07-26 | 1991-11-05 | Abbott Laboratories | Peptidyl aminodiol renin inhibitors |
| US5098924A (en) | 1989-09-15 | 1992-03-24 | E. R. Squibb & Sons, Inc. | Diol sulfonamide and sulfinyl renin inhibitors |
| US5104869A (en) | 1989-10-11 | 1992-04-14 | American Cyanamid Company | Renin inhibitors |
| US5114937A (en) | 1989-11-28 | 1992-05-19 | Warner-Lambert Company | Renin inhibiting nonpeptides |
| US5095119A (en) | 1990-03-08 | 1992-03-10 | American Home Products Corporation | Renin inhibitors |
| US5064965A (en) | 1990-03-08 | 1991-11-12 | American Home Products Corporation | Renin inhibitors |
| US5075451A (en) | 1990-03-08 | 1991-12-24 | American Home Products Corporation | Pyrrolimidazolones useful as renin inhibitors |
| US5071837A (en) | 1990-11-28 | 1991-12-10 | Warner-Lambert Company | Novel renin inhibiting peptides |
| AU6691498A (en) | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel benzimidazole inhibitors of fructose-1,6-bisphosphatase |
| US6284748B1 (en) | 1997-03-07 | 2001-09-04 | Metabasis Therapeutics, Inc. | Purine inhibitors of fructose 1,6-bisphosphatase |
| AU6691798A (en) | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| DE19744026A1 (de) | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE19744027A1 (de) | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Substituierte Pyrazolo[3,4-b]pyridine, ihre Herstellung und Verwendung in Arzneimitteln |
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| EP1112275B9 (en) | 1998-09-09 | 2004-03-10 | Metabasis Therapeutics, Inc. | Novel heteroaromatic inhibitors of fructose 1,6-bisphosphatase |
| JP2004513076A (ja) | 2000-07-25 | 2004-04-30 | メルク エンド カムパニー インコーポレーテッド | 糖尿病治療で有用なｎ−置換インドール類 |
| US6852738B2 (en) | 2001-01-30 | 2005-02-08 | Merck & Co., Inc. | Acyl sulfamides for treatment of obesity, diabetes and lipid disorders |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| AR040241A1 (es) | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
| RU2328483C2 (ru) | 2002-08-29 | 2008-07-10 | Мерк Энд Ко., Инк. | Индолы, обладающие противодиабетической активностью |
| WO2004019869A2 (en) | 2002-08-29 | 2004-03-11 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| CA2512879A1 (en) | 2003-01-17 | 2004-08-12 | Soumya P. Sahoo | N-cyclohexylaminocarbonyl benzenesulfonamide derivatives |
| JP2007504271A (ja) | 2003-09-05 | 2007-03-01 | ニューロジェン・コーポレーション | Ｃｒｆ１受容体リガンドである、ヘテロアリール縮合ピリジン類、ピラジン類及びピリミジン類 |
| WO2009000087A1 (en) | 2007-06-28 | 2008-12-31 | Merck Frosst Canada Ltd. | Substituted fused pyrimidines as antagonists of gpr105 activity |
| KR101404781B1 (ko) | 2007-06-28 | 2014-06-12 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 반도체 장치의 제조 방법 |
| WO2009023179A2 (en) | 2007-08-10 | 2009-02-19 | Genelabs Technologies, Inc. | Nitrogen containing bicyclic chemical entities for treating viral infections |
| KR20100059952A (ko) | 2007-09-06 | 2010-06-04 | 머크 샤프 앤드 돔 코포레이션 | 가용성 구아닐레이트 사이클라제 활성제 |
| WO2009042053A2 (en) | 2007-09-21 | 2009-04-02 | Merck & Co., Inc. | Neuromedin u receptor agonists and uses thereof |
| WO2010065275A1 (en) | 2008-11-25 | 2010-06-10 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| WO2010099054A2 (en) | 2009-02-26 | 2010-09-02 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| GB0917934D0 (en) | 2009-10-13 | 2009-11-25 | Syngenta Ltd | Herbicidal compounds |
| TW201200518A (en) | 2010-03-10 | 2012-01-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| WO2011119518A1 (en) | 2010-03-25 | 2011-09-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| BR112012030177B1 (pt) * | 2010-05-27 | 2019-08-27 | Merck Sharp & Dohme | composto ativador da guanilato ciclase solúvel, e, composição farmacêutica |
| JP6114189B2 (ja) | 2010-07-09 | 2017-04-12 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 縮合ピリミジンおよびトリアジンならびに心血管障害の処置および／または予防のためのその使用 |
| WO2012058132A1 (en) | 2010-10-28 | 2012-05-03 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| CN103619845B (zh) | 2011-04-21 | 2016-08-17 | 拜耳知识产权有限责任公司 | 氟烷基取代的吡唑并吡啶及其用途 |
| CA2834901A1 (en) | 2011-05-06 | 2012-11-15 | Bayer Intellectual Property Gmbh | Substituted imidazopyridines and imidazopyridazines and the use thereof |
| US20140228366A1 (en) | 2011-07-06 | 2014-08-14 | Bayer Intellectual Property Gmbh | Heteroaryl-substituted pyrazolopyridines and use thereof as soluble guanylate cyclase stimulators |
| EP2751106B1 (de) | 2011-09-02 | 2017-10-18 | Bayer Intellectual Property GmbH | Substituierte annellierte pyrimidine und ihre verwendung |
| DE102012200349A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte annellierte Pyrimidine und Triazine und ihre Verwendung |
| DE102012200352A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte, annellierte Imidazole und Pyrazole und ihre Verwendung |
| WO2015088885A1 (en) | 2013-12-11 | 2015-06-18 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| EP3079700B1 (en) | 2013-12-11 | 2020-11-25 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| EP3152214B1 (en) | 2014-06-04 | 2020-01-29 | Merck Sharp & Dohme Corp. | Imidazo-pyrazine derivatives useful as soluble guanylate cyclase activators |
-
2015
- 2015-11-13 TW TW104137596A patent/TW201625635A/zh unknown
- 2015-11-19 CN CN201580063273.3A patent/CN107001389A/zh active Pending
- 2015-11-19 EP EP15801104.9A patent/EP3221319B1/en active Active
- 2015-11-19 BR BR112017010551A patent/BR112017010551A2/pt not_active Application Discontinuation
- 2015-11-19 MX MX2017006649A patent/MX2017006649A/es unknown
- 2015-11-19 AU AU2015349888A patent/AU2015349888A1/en not_active Abandoned
- 2015-11-19 RU RU2017121278A patent/RU2017121278A/ru not_active Application Discontinuation
- 2015-11-19 US US14/945,576 patent/US9822130B2/en active Active
- 2015-11-19 WO PCT/US2015/061442 patent/WO2016081668A1/en not_active Ceased
- 2015-11-19 CA CA2967965A patent/CA2967965A1/en not_active Abandoned
- 2015-11-19 KR KR1020177016515A patent/KR20170084299A/ko not_active Withdrawn
- 2015-11-19 JP JP2017526957A patent/JP2017535561A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017535561A5 (OSRAM) | ||
| RU2017121278A (ru) | Триазоло-пиразинильные производные, применимые в качестве растворимых активаторов гуанилатциклазы | |
| JP2020527560A5 (OSRAM) | ||
| JP2022184886A5 (OSRAM) | ||
| US10421761B2 (en) | Compounds for kinase modulation, and indications therefor | |
| JP5789288B2 (ja) | 可溶性グアニル酸シクラーゼアクチベーター | |
| JP5911638B2 (ja) | ベンゾチアゾール−６−イル酢酸誘導体およびｈｉｖ感染を処置するためのそれらの使用 | |
| JP2016520116A5 (OSRAM) | ||
| JP7654071B2 (ja) | 複素環スピロ化合物及び使用方法 | |
| JP2019503337A5 (OSRAM) | ||
| RU2012130436A (ru) | Новое антитромботическое средство | |
| JP2004525149A5 (OSRAM) | ||
| RU2665036C9 (ru) | Гетероароматические соединения-модуляторы фосфоинозидит-3-киназы и способы применения | |
| RU2017112518A (ru) | Пиридоновые и азапиридоновые соединения и способы применения | |
| EP3004109A1 (en) | Imidazopyrrolidinone derivatives and their use in the treatment of disease | |
| JP2018515525A5 (OSRAM) | ||
| RU2672910C2 (ru) | Гетероароматические соединения как модуляторы фосфоинозитид-3-киназы | |
| JP2013523884A5 (OSRAM) | ||
| JP2016537384A5 (OSRAM) | ||
| KR20150096769A (ko) | 키나제 조절을 위한 화합물 및 방법, 및 그에 대한 적응증 | |
| JP2013522354A5 (OSRAM) | ||
| JP2018529731A5 (OSRAM) | ||
| US20130310374A1 (en) | Substituted Imidazoquinoline Derivatives | |
| EP3668858A1 (en) | Pyrazolo[1,5-a]pyrazin-4-yl and related derivatives | |
| JP2020502230A5 (OSRAM) |