HRP20171660T1 - Spojevi i postupci za modulaciju kinaze, te indikacije za njih - Google Patents
Spojevi i postupci za modulaciju kinaze, te indikacije za njih Download PDFInfo
- Publication number
- HRP20171660T1 HRP20171660T1 HRP20171660TT HRP20171660T HRP20171660T1 HR P20171660 T1 HRP20171660 T1 HR P20171660T1 HR P20171660T T HRP20171660T T HR P20171660TT HR P20171660 T HRP20171660 T HR P20171660T HR P20171660 T1 HRP20171660 T1 HR P20171660T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyridyl
- amino
- fluoro
- pyrrolo
- pyrimidin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 31
- 108091000080 Phosphotransferase Proteins 0.000 title 1
- 102000020233 phosphotransferase Human genes 0.000 title 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 23
- 239000012453 solvate Substances 0.000 claims 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- -1 4-pyrazolyl Chemical group 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 208000002193 Pain Diseases 0.000 claims 8
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 8
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 3
- 208000005298 acute pain Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 201000002528 pancreatic cancer Diseases 0.000 claims 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000010392 Bone Fractures Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 206010059282 Metastases to central nervous system Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 208000009905 Neurofibromatoses Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010052306 Periprosthetic osteolysis Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010038468 Renal hypertrophy Diseases 0.000 claims 2
- LHRCGLXUDAFJTE-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[(1,1-dioxothian-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CS(=O)(=O)CCC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 LHRCGLXUDAFJTE-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 201000008627 kidney hypertrophy Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 201000004931 neurofibromatosis Diseases 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- HHSUOQFZFBXWTK-UHFFFAOYSA-N (4-amino-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(N)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 HHSUOQFZFBXWTK-UHFFFAOYSA-N 0.000 claims 1
- MCAADPPLQIKSNB-UHFFFAOYSA-N (4-amino-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 MCAADPPLQIKSNB-UHFFFAOYSA-N 0.000 claims 1
- NJDNEOJYPDSWCL-UHFFFAOYSA-N (4-amino-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N)=C12 NJDNEOJYPDSWCL-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- INHWYJCCLKTJGY-UHFFFAOYSA-N 4-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1-methylpiperidin-2-one Chemical compound C1C(=O)N(C)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 INHWYJCCLKTJGY-UHFFFAOYSA-N 0.000 claims 1
- QFXDKMGIHBVRGX-UHFFFAOYSA-N 4-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 QFXDKMGIHBVRGX-UHFFFAOYSA-N 0.000 claims 1
- YUNLJTVRPLBFTN-UHFFFAOYSA-N 4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1-methylpiperidin-2-one Chemical compound C1C(=O)N(C)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(=CC=3)C3CC3)=CC=1)F)=CN2 YUNLJTVRPLBFTN-UHFFFAOYSA-N 0.000 claims 1
- NCVGEUDTYJBSMF-UHFFFAOYSA-N 4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]piperidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NCC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 NCVGEUDTYJBSMF-UHFFFAOYSA-N 0.000 claims 1
- RLWNUHAGAKPBBV-UHFFFAOYSA-N 4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 RLWNUHAGAKPBBV-UHFFFAOYSA-N 0.000 claims 1
- WTYADSIKJZTFJI-UHFFFAOYSA-N 5-[[6-(cyclohexylamino)-2-fluoropyridin-3-yl]methyl]-n-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(CC=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCCCC1 WTYADSIKJZTFJI-UHFFFAOYSA-N 0.000 claims 1
- WRCVQOCGIBTZHJ-UHFFFAOYSA-N 5-[[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methyl]-n-(2,2,2-trifluoroethyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(CC=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 WRCVQOCGIBTZHJ-UHFFFAOYSA-N 0.000 claims 1
- SANIUIWLLLEGJH-UHFFFAOYSA-N 5-[[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methyl]-n-(2,2,2-trifluoroethyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(CC=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 SANIUIWLLLEGJH-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010006002 Bone pain Diseases 0.000 claims 1
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000007569 Giant Cell Tumors Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000028622 Immune thrombocytopenia Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 208000015439 Lysosomal storage disease Diseases 0.000 claims 1
- 206010027452 Metastases to bone Diseases 0.000 claims 1
- 208000006670 Multiple fractures Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010038540 Renal tubular necrosis Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- NRHWYWIIFWCXTO-UHFFFAOYSA-N [2-chloro-6-(cyclohexylamino)pyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCCCC1 NRHWYWIIFWCXTO-UHFFFAOYSA-N 0.000 claims 1
- KNEGJOPIJIRDOK-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC(F)(F)F)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 KNEGJOPIJIRDOK-UHFFFAOYSA-N 0.000 claims 1
- DSRQJGZVRXOCQH-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1CC(F)(F)CCC1NC(N=C1Cl)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 DSRQJGZVRXOCQH-UHFFFAOYSA-N 0.000 claims 1
- VGSSPQMRSDVCDE-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 VGSSPQMRSDVCDE-UHFFFAOYSA-N 0.000 claims 1
- YLBZHNFWGMYDDT-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 YLBZHNFWGMYDDT-UHFFFAOYSA-N 0.000 claims 1
- IVNPIZKBXPBLLI-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1CC(F)CCC1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(F)(F)F)=C12 IVNPIZKBXPBLLI-UHFFFAOYSA-N 0.000 claims 1
- WYIDRDMKRPEKEF-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 WYIDRDMKRPEKEF-UHFFFAOYSA-N 0.000 claims 1
- PGOHENXRKHRKHN-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(methoxymethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 PGOHENXRKHRKHN-UHFFFAOYSA-N 0.000 claims 1
- PQZQDKDOBUWBFM-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 PQZQDKDOBUWBFM-UHFFFAOYSA-N 0.000 claims 1
- DCMWXXAKOGADFO-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(oxan-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1CC(F)CCC1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCOCC3)=C12 DCMWXXAKOGADFO-UHFFFAOYSA-N 0.000 claims 1
- UYOWRFDIDRQRKR-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound COC1=CN=CC(NC=2N=C(F)C(C(=O)C=3C4=C(NCC(F)(F)F)N=CN=C4NC=3)=CC=2)=C1 UYOWRFDIDRQRKR-UHFFFAOYSA-N 0.000 claims 1
- ZVQNVYRKVWPYBM-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CN=CC(OC)=C1 ZVQNVYRKVWPYBM-UHFFFAOYSA-N 0.000 claims 1
- RATANAFRZIPGTF-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound COC1=CN=CC(NC=2N=C(F)C(C(=O)C=3C4=C(NC(C)C)N=CN=C4NC=3)=CC=2)=C1 RATANAFRZIPGTF-UHFFFAOYSA-N 0.000 claims 1
- BLJRHFNFRNIISP-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CN=CC(OC)=C1 BLJRHFNFRNIISP-UHFFFAOYSA-N 0.000 claims 1
- FPHOGLJGMLSCQH-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N3CCOCC3)=C12 FPHOGLJGMLSCQH-UHFFFAOYSA-N 0.000 claims 1
- FVFHEIGDUBGYDJ-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-(4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N3CCCCC3)=C12 FVFHEIGDUBGYDJ-UHFFFAOYSA-N 0.000 claims 1
- PWFRRCRPLOOVLK-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(F)(F)F)=C12 PWFRRCRPLOOVLK-UHFFFAOYSA-N 0.000 claims 1
- CHTCUCONDUXAEE-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 CHTCUCONDUXAEE-UHFFFAOYSA-N 0.000 claims 1
- SDJXXHWYKHLCED-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 SDJXXHWYKHLCED-UHFFFAOYSA-N 0.000 claims 1
- KPWCIJXXGAIBCF-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(oxolan-2-ylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3OCCC3)=C12 KPWCIJXXGAIBCF-UHFFFAOYSA-N 0.000 claims 1
- NHRYYSKFZNHNKN-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(pentan-3-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(CC)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 NHRYYSKFZNHNKN-UHFFFAOYSA-N 0.000 claims 1
- PXQVDDZXJLCQFS-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 PXQVDDZXJLCQFS-UHFFFAOYSA-N 0.000 claims 1
- OVZQVBPXCQJZDW-CQSZACIVSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-[[(1R)-1-(4-fluorophenyl)ethyl]amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound COc1ccc(Nc2ccc(C(=O)c3c[nH]c4ncnc(N[C@H](C)c5ccc(F)cc5)c34)c(F)n2)cn1 OVZQVBPXCQJZDW-CQSZACIVSA-N 0.000 claims 1
- OVZQVBPXCQJZDW-AWEZNQCLSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N[C@@H](C)C=3C=CC(F)=CC=3)=C12 OVZQVBPXCQJZDW-AWEZNQCLSA-N 0.000 claims 1
- RYVOCKFHUXYHJD-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC=3C=NC(=CC=3)C(F)(F)F)=C12 RYVOCKFHUXYHJD-UHFFFAOYSA-N 0.000 claims 1
- WROCPEAEWKBPSQ-UHFFFAOYSA-N [2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(F)(F)F)=C12 WROCPEAEWKBPSQ-UHFFFAOYSA-N 0.000 claims 1
- PMPQAEQHSYUJPD-UHFFFAOYSA-N [2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(C)N=C1 PMPQAEQHSYUJPD-UHFFFAOYSA-N 0.000 claims 1
- XLOVWHBMDZAAQU-UHFFFAOYSA-N [2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(C)N=C1 XLOVWHBMDZAAQU-UHFFFAOYSA-N 0.000 claims 1
- UDYZZJBRHGPPKF-UHFFFAOYSA-N [2-fluoro-6-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(C(F)(F)F)N=C1 UDYZZJBRHGPPKF-UHFFFAOYSA-N 0.000 claims 1
- DEBXQNXQYQWNAH-UHFFFAOYSA-N [4-(butan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NC(C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 DEBXQNXQYQWNAH-UHFFFAOYSA-N 0.000 claims 1
- SEHVKNHBWWPHSA-UHFFFAOYSA-N [4-(butylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 SEHVKNHBWWPHSA-UHFFFAOYSA-N 0.000 claims 1
- WIGMCZFCZCSMMW-UHFFFAOYSA-N [4-(butylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(NCCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(CC)N=C1 WIGMCZFCZCSMMW-UHFFFAOYSA-N 0.000 claims 1
- CPDWZEWHLKZRPK-UHFFFAOYSA-N [4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1CC(F)CCC1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC3)=C12 CPDWZEWHLKZRPK-UHFFFAOYSA-N 0.000 claims 1
- UOCJEKKRDDEQOY-UHFFFAOYSA-N [4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CCC4)N=CN=C3NC=2)C(F)=NC=1NC1CC(F)(F)C1 UOCJEKKRDDEQOY-UHFFFAOYSA-N 0.000 claims 1
- SKFWYKIBBFEPDL-UHFFFAOYSA-N [4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CCC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 SKFWYKIBBFEPDL-UHFFFAOYSA-N 0.000 claims 1
- RZBZKNSIVHKKOV-UHFFFAOYSA-N [4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC3)=C12 RZBZKNSIVHKKOV-UHFFFAOYSA-N 0.000 claims 1
- MJMGSHMCTGDDFP-UHFFFAOYSA-N [4-(cyclohexylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound COC1=CN=CC(NC=2N=C(F)C(C(=O)C=3C4=C(NC5CCCCC5)N=CN=C4NC=3)=CC=2)=C1 MJMGSHMCTGDDFP-UHFFFAOYSA-N 0.000 claims 1
- PKIKTIUCRYUKKG-UHFFFAOYSA-N [4-(cyclohexylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCCCC3)=C12 PKIKTIUCRYUKKG-UHFFFAOYSA-N 0.000 claims 1
- SYPWIOWRJUHZFJ-UHFFFAOYSA-N [4-(cyclopentylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCCC3)=C12 SYPWIOWRJUHZFJ-UHFFFAOYSA-N 0.000 claims 1
- PIGOLIXOPXWVLS-UHFFFAOYSA-N [4-(cyclopentylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCCC3)=C12 PIGOLIXOPXWVLS-UHFFFAOYSA-N 0.000 claims 1
- SWBBIIIBOYOSKX-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1CC(F)CCC1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 SWBBIIIBOYOSKX-UHFFFAOYSA-N 0.000 claims 1
- NNOPOPDWWUVUEL-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound COC1=CN=CC(NC=2N=C(F)C(C(=O)C=3C4=C(NC5CC5)N=CN=C4NC=3)=CC=2)=C1 NNOPOPDWWUVUEL-UHFFFAOYSA-N 0.000 claims 1
- XTLZUAAGYLGJEM-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 XTLZUAAGYLGJEM-UHFFFAOYSA-N 0.000 claims 1
- RDBRHLLTUROZDI-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1=CC=C(C(F)(F)F)N=C1 RDBRHLLTUROZDI-UHFFFAOYSA-N 0.000 claims 1
- DHMZZTHZKKUJPN-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 DHMZZTHZKKUJPN-UHFFFAOYSA-N 0.000 claims 1
- PGDNQHCNRNEZST-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 PGDNQHCNRNEZST-UHFFFAOYSA-N 0.000 claims 1
- AMOXKRFYMZWTAI-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 AMOXKRFYMZWTAI-UHFFFAOYSA-N 0.000 claims 1
- USDGGAHPETZXCE-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 USDGGAHPETZXCE-UHFFFAOYSA-N 0.000 claims 1
- RGSWZIQVPKTVSQ-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 RGSWZIQVPKTVSQ-UHFFFAOYSA-N 0.000 claims 1
- ZSRQKNXWSKESRS-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 ZSRQKNXWSKESRS-UHFFFAOYSA-N 0.000 claims 1
- RECGXXWAANSOAE-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 RECGXXWAANSOAE-UHFFFAOYSA-N 0.000 claims 1
- PZGILXHXYSCVQW-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 PZGILXHXYSCVQW-UHFFFAOYSA-N 0.000 claims 1
- JYYOWPLYDVTMEM-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(CC)N=C1 JYYOWPLYDVTMEM-UHFFFAOYSA-N 0.000 claims 1
- HCFXIXONMLXQLJ-UHFFFAOYSA-N [4-(tert-butylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC(C)(C)C)=C12 HCFXIXONMLXQLJ-UHFFFAOYSA-N 0.000 claims 1
- QKRHXRNNIDKEBP-UHFFFAOYSA-N [4-[(1-ethylpiperidin-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1CN(CC)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(OC)=CC=3)=CC=1)F)=CN2 QKRHXRNNIDKEBP-UHFFFAOYSA-N 0.000 claims 1
- WNICXRILOHTSDF-UHFFFAOYSA-N [4-[(4,4-difluorocyclohexyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC(F)(F)CC3)=C12 WNICXRILOHTSDF-UHFFFAOYSA-N 0.000 claims 1
- NICCYTIXGQSYBK-UHFFFAOYSA-N [4-[(4,4-difluorocyclohexyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC(F)(F)CC3)=C12 NICCYTIXGQSYBK-UHFFFAOYSA-N 0.000 claims 1
- HTNOMZMPUYZIGE-LRVUVFPRSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 HTNOMZMPUYZIGE-LRVUVFPRSA-N 0.000 claims 1
- WWLTXCJGKUULKE-SNVBAGLBSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 WWLTXCJGKUULKE-SNVBAGLBSA-N 0.000 claims 1
- DYHZSAQXHDXWDO-GFCCVEGCSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 DYHZSAQXHDXWDO-GFCCVEGCSA-N 0.000 claims 1
- HTNOMZMPUYZIGE-GRTSSRMGSA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 HTNOMZMPUYZIGE-GRTSSRMGSA-N 0.000 claims 1
- WWLTXCJGKUULKE-JTQLQIEISA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 WWLTXCJGKUULKE-JTQLQIEISA-N 0.000 claims 1
- DYHZSAQXHDXWDO-LBPRGKRZSA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 DYHZSAQXHDXWDO-LBPRGKRZSA-N 0.000 claims 1
- GQGXOAFWKBFUPX-LBPRGKRZSA-N [4-[[(2s)-butan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N[C@@H](C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 GQGXOAFWKBFUPX-LBPRGKRZSA-N 0.000 claims 1
- HBRLFMUTJKOUOY-ZDUSSCGKSA-N [4-[[(2s)-butan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N[C@@H](C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 HBRLFMUTJKOUOY-ZDUSSCGKSA-N 0.000 claims 1
- MLZJHYYTGXCFDI-UHFFFAOYSA-N [6-(cyclohexylamino)-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCCCC1 MLZJHYYTGXCFDI-UHFFFAOYSA-N 0.000 claims 1
- IUWDOUDLGKJYOM-UHFFFAOYSA-N [6-(cyclohexylamino)-2-fluoropyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCCCC1 IUWDOUDLGKJYOM-UHFFFAOYSA-N 0.000 claims 1
- KMUJEQBTZNFUTI-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC1CC(F)(F)C1 KMUJEQBTZNFUTI-UHFFFAOYSA-N 0.000 claims 1
- OKZIXHATEKJFCV-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 OKZIXHATEKJFCV-UHFFFAOYSA-N 0.000 claims 1
- FBQYBWMASKYPQH-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 FBQYBWMASKYPQH-UHFFFAOYSA-N 0.000 claims 1
- KOVBGKZUQLABCR-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(methoxymethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 KOVBGKZUQLABCR-UHFFFAOYSA-N 0.000 claims 1
- AIWOCBWNWVBKCK-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 AIWOCBWNWVBKCK-UHFFFAOYSA-N 0.000 claims 1
- JCTCPKUYDKZSCR-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 JCTCPKUYDKZSCR-UHFFFAOYSA-N 0.000 claims 1
- AYVPLGIMBXBDSH-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 AYVPLGIMBXBDSH-UHFFFAOYSA-N 0.000 claims 1
- FENZTOJYXRYVBZ-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 FENZTOJYXRYVBZ-UHFFFAOYSA-N 0.000 claims 1
- BNDLGCCGTQTJAL-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(2-methoxyethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 BNDLGCCGTQTJAL-UHFFFAOYSA-N 0.000 claims 1
- SGSWGBQLRLNDJP-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 SGSWGBQLRLNDJP-UHFFFAOYSA-N 0.000 claims 1
- IWAOCCCXQLRBIP-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(4-hydroxybutan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(CCO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 IWAOCCCXQLRBIP-UHFFFAOYSA-N 0.000 claims 1
- UFJCQWQNZVJFEU-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UFJCQWQNZVJFEU-UHFFFAOYSA-N 0.000 claims 1
- LLQDTYOHPTWZIA-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 LLQDTYOHPTWZIA-UHFFFAOYSA-N 0.000 claims 1
- BLPGXVOGHTVVKM-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(oxan-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CCOCC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 BLPGXVOGHTVVKM-UHFFFAOYSA-N 0.000 claims 1
- QRIPRUSSGVOLQJ-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[(1,1-dioxothiolan-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CS(=O)(=O)CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 QRIPRUSSGVOLQJ-UHFFFAOYSA-N 0.000 claims 1
- UURRFCIRZCTHIV-SNVBAGLBSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)C(F)(F)F)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UURRFCIRZCTHIV-SNVBAGLBSA-N 0.000 claims 1
- WTXNGRKDIZVULC-GFCCVEGCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxybutan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 WTXNGRKDIZVULC-GFCCVEGCSA-N 0.000 claims 1
- LRNOPCNTRVGVIB-LLVKDONJSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 LRNOPCNTRVGVIB-LLVKDONJSA-N 0.000 claims 1
- UOHFJNMMFPVFEW-GFCCVEGCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-methoxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)COC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UOHFJNMMFPVFEW-GFCCVEGCSA-N 0.000 claims 1
- JWGYHEGOQZVAOT-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 JWGYHEGOQZVAOT-UHFFFAOYSA-N 0.000 claims 1
- JWCDSHIWFRMHAG-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(4-hydroxybutan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(CCO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 JWCDSHIWFRMHAG-UHFFFAOYSA-N 0.000 claims 1
- SDAGHBYLOGGCFP-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 SDAGHBYLOGGCFP-UHFFFAOYSA-N 0.000 claims 1
- VBHLKVYEPTYWMP-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[(1,1-dioxothian-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CS(=O)(=O)CCC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 VBHLKVYEPTYWMP-UHFFFAOYSA-N 0.000 claims 1
- PLGRWFYWCZSJCU-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[(2-hydroxy-2-methylpropyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC(C)(O)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 PLGRWFYWCZSJCU-UHFFFAOYSA-N 0.000 claims 1
- XFJOFQKRWJHXTA-LLVKDONJSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)C(F)(F)F)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 XFJOFQKRWJHXTA-LLVKDONJSA-N 0.000 claims 1
- XNEKKGRUDFBXJS-CQSZACIVSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxybutan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 XNEKKGRUDFBXJS-CQSZACIVSA-N 0.000 claims 1
- IFKWVZBGWSQRNQ-GFCCVEGCSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 IFKWVZBGWSQRNQ-GFCCVEGCSA-N 0.000 claims 1
- NXYJGRDGHPDSRT-CYBMUJFWSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-methoxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)COC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 NXYJGRDGHPDSRT-CYBMUJFWSA-N 0.000 claims 1
- SHTXMIJOPIKDLI-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(F)(F)F)=C12 SHTXMIJOPIKDLI-UHFFFAOYSA-N 0.000 claims 1
- CXWLVIXFFABWKC-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(2-methoxyethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCCOC)=C12 CXWLVIXFFABWKC-UHFFFAOYSA-N 0.000 claims 1
- OFPUKCDGHDUEMO-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(2-methylpropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(C)C)=C12 OFPUKCDGHDUEMO-UHFFFAOYSA-N 0.000 claims 1
- MDYACODVGZYCEL-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCCCOC)=C12 MDYACODVGZYCEL-UHFFFAOYSA-N 0.000 claims 1
- QSSQFUZJTHJXGT-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC)=C12 QSSQFUZJTHJXGT-UHFFFAOYSA-N 0.000 claims 1
- WXAOXLFSDVCIIW-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(oxan-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCOCC3)=C12 WXAOXLFSDVCIIW-UHFFFAOYSA-N 0.000 claims 1
- BVADCBZLJPCTRQ-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC(C)C)=C12 BVADCBZLJPCTRQ-UHFFFAOYSA-N 0.000 claims 1
- SDLSSKZWMVKYKN-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(CC)N=C1 SDLSSKZWMVKYKN-UHFFFAOYSA-N 0.000 claims 1
- QMMTZSFZPNOWJC-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[(2-hydroxy-2-methylpropyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(C)(C)O)=C12 QMMTZSFZPNOWJC-UHFFFAOYSA-N 0.000 claims 1
- NLKKRUJTDKZYLX-UHFFFAOYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[(6-methylpyridin-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC=3C=NC(C)=CC=3)=C12 NLKKRUJTDKZYLX-UHFFFAOYSA-N 0.000 claims 1
- ISRDIBYOJNKGJE-OAHLLOKOSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r)-1-(4-fluorophenyl)ethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N[C@H](C)C=3C=CC(F)=CC=3)=C12 ISRDIBYOJNKGJE-OAHLLOKOSA-N 0.000 claims 1
- ISRDIBYOJNKGJE-HNNXBMFYSA-N [6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N[C@@H](C)C=3C=CC(F)=CC=3)=C12 ISRDIBYOJNKGJE-HNNXBMFYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 201000006334 interstitial nephritis Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- VKJMBMYIPBPEKA-UHFFFAOYSA-N n-cyclopropyl-5-[[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(CC=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 VKJMBMYIPBPEKA-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
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Claims (23)
1. Spoj koji ima kemijsku strukturu s Formulom I,
[image]
ili njegova sol, solvat, tautomer ili stereoizomer,
naznačen time da:
X1 je -N=;
Y1 je -N= i R3 je H; ili Y1 je -C(H)= i R3 je fluoro ili kloro;
L1 je -CH2- ili -C(O)-;
Cy1 je cikloalkil proizvoljno supstituiran s jednim ili više R4, fenil proizvoljno supstituiran s jednim ili više R5, ili 5 ili 6 člani heteroaril proizvoljno supstituiran na raspoloživom ugljikovom atomu s jednim ili više R6 i proizvoljno supstituiran na raspoloživom dušikovom atomu s R7;
R2 je -N(R9a)(R9b);
svaki R4 je neovisno odabran iz skupine koja sadrži fluoro, -OH, C1-C6 alkil proizvoljno supstituiran s jednim ili više fluoro, i C1-C6 alkoksi proizvoljno supstituiran s jednim ili više fluoro;
svaki R5 je neovisno odabran iz skupine koja sadrži fluoro, kloro, -O-R10, -S-R11, -S(O2)-R12, i C1-C6 alkil proizvoljno supstituiran s jednim ili više R13;
svaki R6 je neovisno odabran iz skupine koja sadrži fluoro, kloro, bromo, cikloalkil, C1-C6 alkil proizvoljno supstituiran s jednim ili više fluoro, i C1-C6 alkoksi proizvoljno supstituiran s jednim ili više fluoro; ili dva R6 vezani na susjedne ugljikove atome heteroarilnog prstena tvore kondenzirani cikloalkilni prsten;
R7 je cikloalkil, C1-C6 alkoksi ili C1-C6 alkil proizvoljno supstituiran s jednim ili više fluoro;
R9a je H i R9b je odabran iz skupine koju čine (i) H, C1-C6 alkil, C1-C6 alkil supstituiran s jednim ili više fluoro, C1-C6 alkil supstituiran s C1-C6 alkoksi ili C1-C6 alkil supstituiran s hidroksilom i (ii) cikloalkil, cikloalkilalkil, heterocikloalkil, heterocikloalkilalkil, arilalkil, heteroarilalkil, svaki od kojih je proizvoljno supstituiran s jednim do tri člana koji se biraju od C1-C6 alkil, haloalkil, C1-C6 alkoksi ili fluoro; ili
R9a i R9b zajedno s dušikom na koji su vezani tvore 5- ili 6-člani prsten koji ima od 0 do 1 dodatni heteroatom koji se bira od O, N ili S, svaki od kojih je proizvoljno supstituiran s jednim do tri člana koji se biraju od C1-C6 alkil, haloalkil, C1-C6 alkoksi ili fluoro;
svaki R10, R11 i R12 su neovisno C1-C6 alkil proizvoljno supstituiran s jednim ili više fluoro; i
svaki R13 je neovisno odabran iz skupine koja sadrži fluoro, -OH, i C1-C6 alkoksi proizvoljno supstituiran s jednim ili više fluoro.
2. Spoj prema zahtjevu 1, naznačen time da:
L1 je -CH2-, Y1 je -C(H)= i R3 je fluoro;
L1 je -CH2-, Y1 je -N= i R3 je H ;
L1 je -C(O)-, Y1 je -C(H)= i R3 je fluoro; ili
L1 je -C(O)-, Y1 je -N= i R3 je H,
ili njegova sol, solvat, tautomer ili stereoizomer.
3. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time da Cy1 je cikloalkil proizvoljno supstituiran s jednim ili više R4, poželjno pri čemu Cy1 je ciklopropil, ciklobutil, ciklopentil, ili cikloheksil, svaki od kojih je proizvoljno supstituiran s od 1 do 3 R4, ili njegova sol, solvat, tautomer ili stereoizomer.
4. Spoj prema bilo kojem od zahtjeva 1 ili 2, naznačen time da Cy1 je fenil proizvoljno supstituiran s jednim ili više R5, ili njegova sol, solvat, tautomer ili stereoizomer.
5. Spoj prema bilo kojem od zahtjeva 1 ili 2, naznačen time da Cy1 je 5 ili 6-člani heteroaril proizvoljno supstituiran na raspoloživom ugljikovom atomu s jednim ili više R6 i proizvoljno supstituiran na raspoloživom dušikovom atomu s R7, poželjno pri čemu Cy1 je 3-piridil, 2-pirolil, 3-pirolil ili 4-pyrazolil, proizvoljno supstituiran na raspoloživom ugljikovom atomu s od 1 do 3 R6 i proizvoljno supstituiran na raspoloživom dušikovom atomu s R7, ili njegova sol, solvat, tautomer ili stereoizomer.
6. Spoj prema zahtjevu 5, naznačen time da je svaki R6 neovisno odabran iz skupine koja sadrži fluoro, kloro, bromo, cikloalkil, C1-C6 alkil proizvoljno supstituiran s od jednim do tri fluoro, i C1-C6 alkoksi proizvoljno supstituiran s jednim do tri fluoro; ili dva R6 vezani na susjedne ugljikove atome heteroarilnog prstena tvore kondenzirani cikloalkilni prsten, ili njegova sol, solvat, tautomer ili stereoizomer.
7. Spoj prema bilo kojem od zahtjeva 1 ili 2, naznačen time da R9a je H i R9b je odabran od H, C1-C6 alkil, C1-C6 alkil supstituiran s hidroksi, C1-C6 alkil supstituiran s C1-C6 alkoksi, C1-C6 alkil supstituiran s 1 do 3 fluoro skupine, cikloalkil proizvoljno supstituiran s C1-C6 alkilom ili jednim do tri fluoro, cikloalkilalkil proizvoljno supstituiran s C1-C6 alkilom ili jednim do tri fluoro supstituenata, heterocikloalkil proizvoljno supstituiran s C1-C6 alkilom, heterocikloalkilalkil, arilalkil proizvoljno supstituiran s od 1 do 3 člana koji se biraju od C1-C6 alkila, fluoro ili haloalkil i heteroarilalkil proizvoljno supstituiran s od jednog do tri člana koji se biraju iz niza koji čine alkil, fluoro ili haloalkil, poželjno pri čemu R9a je H i R9b je odabran od (i) H, metil, etil, t-butil, propil, izopropil, 2-butil, n-butil, 2-hidroksi-2-metilpropil, 2-metoksietil, 3-metoksipropil, 2,2,2-trifluoroetil, ili 4-metoksibutil i (ii) ciklopropil, ciklobutil, ciklopentil, cikloheksil, ciklopropilmetil, ciklobutilmetil, ciklopentilmetil, cikloheksilmetil, benzil, 1-metilbenzil, 4,4-difluorocikloheksil, 2-tetrahidrofuranilmetil, ili 4-piperidinil, svaki od kojih je proizvoljno supstituiran s od 1 do 3 člana koji se biraju od C1-C6 alkila, fluoro ili CF, ili njegova sol, solvat, tautomer ili stereoizomer.
8. Spoj prema bilo kojem od zahtjeva 1 ili 2, naznačen time da -N(R9a)(R9b) je 1-piperidinil, 4-morfolinil, 1-piperazinil ili 1-pirolidinil, svaki od kojih je proizvoljno supstituiran s jednim do tri člana koji se biraju od C1-C6 alkil, haloalkil, C1-C6 alkoksi ili fluoro, ili njegova sol, solvat, tautomer ili stereoizomer.
9. Spoj prema zahtjevu 1, naznačen time da je spoj odabran iz skupine koja sadrži:
(4-amino-7H-pirolo[2,3-d]pirimidin-5-il)-[2-kloro-6-[(4,4-difluorocikloheksil)amino]-3-piridil]metanon (P-4046),
(4-amino-7H-pirolo[2,3-d]pirimidin-5-il)-[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4048),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[(2-hidroksi-2-metil-propil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4049),
[2-kloro-6-[(4,4-difluorocikloheksil)amino]-3-piridil]-[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4050),
[4-(tert-butilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4055),
[4-[(4,4-difluorocikloheksil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4056),
[2-kloro-6-[(4,4-difluorocikloheksil)amino]-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4057),
[2-kloro-6-[(4,4-difluorocikloheksil)amino]-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4058),
[2-kloro-6-[(4,4-difluorocikloheksil)amino]-3-piridil]-[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4059),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4060),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4061),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]metanon (P-4062),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4063),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[(2-hidroksi-2-metil-propil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4064),
(4-amino-7H-pirolo[2,3-d]pirimidin-5-il)-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4065),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4066),
[4-(ciklopropilmetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4067),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(propilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4068),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(1-piperidil)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4069),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-(4-morfolino-7H-pirolo[2,3-d]pirimidin-5-il)metanon (P-4070),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-[[6-(trifluorometil)-3-piridil]metilamino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4071),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-[[(1S)-1-(4-fluorofenil)etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4072),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(tetrahidrofuran-2-ilmetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4073),
[4-[(1-etil-4-piperidil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4074),
[4-(ciklopentilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4075),
[4-(ciklobutilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4076),
[4-(1-etilpropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4077),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(sec-butilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4078),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(3-metoksipropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4079),
[4-(butilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4080),
[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4081),
[4-(cikloheksilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4082),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4083),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4084),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[(6-metil-3-piridil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4086),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4090),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[[6-(trifluorometil)-3-piridil]amino]-3-piridil]metanon (P-4091),
[2-fluoro-6-[[6-(trifluorometil)-3-piridil]amino]-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4092),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4093),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4094),
[4-(ciklobutilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4095),
[4-[(4,4-difluorocikloheksil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4096),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1S)-1-(4-fluorofenil)etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4097),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(3-metoksipropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4098),
[4-(ciklopentilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4099),
[4-(butilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4100),
[6-(cikloheksilamino)-2-fluoro-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4101),
[6-(cikloheksilamino)-2-fluoro-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4102),
[2-fluoro-6-[(5-metoksi-3-piridil)amino]-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4103),
[4-(cikloheksilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(5-metoksi-3-piridil)amino]-3-piridil]metanon (P-4104),
[2-fluoro-6-[(5-metoksi-3-piridil)amino]-3-piridil]-[4-(propilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4105),
[2-fluoro-6-[(5-metoksi-3-piridil)amino]-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4106),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(5-metoksi-3-piridil)amino]-3-piridil]metanon (P-4107),
[2-fluoro-6-[(5-metoksi-3-piridil)amino]-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4108),
[2-kloro-6-(cikloheksilamino)-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4109),
[2-kloro-6-(cikloheksilamino)-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4110),
[4-(cikloheksilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metil-3-piridil)amino]-3-piridil]metanon (P-4111),
[2-fluoro-6-[(6-metil-3-piridil)amino]-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4112),
[4-(ciklopropilmetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metil-3-piridil)amino]-3-piridil]metanon (P-4113),
[2-fluoro-6-[(6-metil-3-piridil)amino]-3-piridil]-[4-(propilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4114),
[2-fluoro-6-[(6-metil-3-piridil)amino]-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4115),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(tetrahidropyran-4-ilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4116),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4117),
[4-(ciklopropilmetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4118),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(2-metoksietilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4119),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4120),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(isobutilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4121),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(propilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4122),
[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4123),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4124),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]metanon (P-4125),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]metanon (P-4126),
5-[[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]metil]-N-(2,2,2-trifluoroetil)-7H-pirolo[2,3-d]pirimidin-4-amin (P-4128),
N-ciklopropil-5-[[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]metil]-7H-pirolo[2,3-d]pirimidin-4-amin (P-4129),
5-[[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]metil]-N-(2,2,2-trifluoroetil)-7H-pirolo[2,3-d]pirimidin-4-amin (P-4130),
5-[[6-(cikloheksilamino)-2-fluoro-3-piridil]metil]-N-ciklopropil-7H-pirolo[2,3-d]pirimidin-4-amin (P-4131),
[2-fluoro-6-[(6-metoksi-3-piridil)amino]-3-piridil]-[4-[[(1R)-1-(4-fluorofenil)etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4132),
[6-[(6-etil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-1-(4-fluorofenil)etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4133),
[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4134),
[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]metanon (P-4135),
[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4136),
[4-(ciklopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]metanon (P-4137),
[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4138),
[4-[[(1R)-1-ciklopropiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]metanon (P-4139),
[4-[[(1S)-1-ciklopropiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]metanon (P-4140),
[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]-[4-(metoksimetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4141),
[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]-[4-(3-metoksipropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4142),
[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]-[4-(tetrahidropyran-4-ilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4143),
[4-(ciklobutilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[2-fluoro-6-[(4-fluorocikloheksil)amino]-3-piridil]metanon (P-4144),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(metilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4145),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4146),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(propilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4147),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(izopropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4148),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(2,2,2-trifluoroetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4149),
[4-[[(1R)-1-ciklopropiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]metanon (P-4150),
[4-[[(1S)-1-ciklopropiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]metanon (P-4151),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(metoksimetilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4152),
[6-[(3,3-15difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(tetrahidropyran-4-ilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4153),
[4-(ciklobutilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]metanon (P-4154),
[6-[(3,3-difluorociklobutil)amino]-2-fluoro-3-piridil]-[4-(3-metoksipropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4155),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-(3-metoksipropilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4156),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-(2-metoksietilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4157),
[4-(ciklobutilamino)-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]metanon (P-4158),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-(tetrahidropyran-4-ilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4159),
[4-[[(1R)-1-ciklopropiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]metanon (P-4160),
[4-[[(1S)-1-ciklopropiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]metanon (P-4161),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-(etilamino)-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4162),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1S)-1-metilpropil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4169),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[(3-hidroksi-1-metilpropil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4170),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-1-(hidroksimetil)propil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4171),
4-[[5-[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-piridin-3-karbonil]-7H-pirolo[2,3-d]pirimidin-4-il]amino]pirolidin-2-on (P-4172),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-2-hidroksi-1-metil-etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4173),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[(1,1-dioksotiolan-3-il)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4178),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-2-metoksi-1-metil-etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4180),
4-[[5-[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-piridin-3-karbonil]-7H-pirolo[2,3-d]pirimidin-4-il]amino]piperidin-2-on (P-4181),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-2,2,2-trifluoro-1-metil-etil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4182),
4-[[5-[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-piridin-3-karbonil]-7H-pirolo[2,3-d]pirimidin-4-il]amino]-1-metil-piperidin-2-on (P-4183),
[6-[(6-ciklopropil-3-piridil)amino]-2-fluoro-3-piridil]-[4-[(1,1-dioksotian-3-il)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4184),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[[(1S)-1-metilpropil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4186),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[(3-hidroksi-1-metilpropil)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4187),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-1-(hidroksimetil)propil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4188),
4-[[5-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-piridin-3-karbonil]-7H-pirolo[2,3-d]pirimidin-4-il]amino]pirolidin-2-on (P-4189),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-2-hidroksi-1-metiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4190),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[(1,1-dioksotiolan-3-il)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4195),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-2-metoksi-1-metiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4197),
4-[[5-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-piridin-3-karbonil]-7H-pirolo[2,3-d]pirimidin-4-il]amino]piperidin-2-on (P-4198),
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[[(1R)-2,2,2-trifluoro-1-metiletil]amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4199),
4-[[5-[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-piridin-3-karbonil]-7H-pirolo[2,3-d]pirimidin-4-il]amino]-1-metil-piperidin-2-on (P-4200), i
[6-[(4,4-difluorocikloheksil)amino]-2-fluoro-3-piridil]-[4-[(1,1-dioksotian-3-il)amino]-7H-pirolo[2,3-d]pirimidin-5-il]metanon (P-4201);
ili njegova sol, solvat, tautomer ili stereoizomer.
10. Spoj prema zahtjevu 1, naznačen time da je spoj odabran iz skupine koja sadrži:
[image]
[image]
[image]
[image]
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[image]
[image]
[image]
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i
[image]
ili njegova sol, solvat, tautomer ili stereoizomer.
11. Spoj prema zahtjevu 1, naznačen time da spoj je
[image]
ili njegova sol, solvat, tautomer ili stereoizomer.
12. Spoj prema zahtjevu 1, naznačen time da spoj je
[image]
ili njegova sol, solvat, tautomer ili stereoizomer.
13. Spoj prema zahtjevu 1, naznačen time da spoj je
[image]
ili njegova sol, solvat, tautomer ili stereoizomer.
14. Spoj prema zahtjevu 1, naznačen time da spoj je
[image]
ili njegova sol, solvat, tautomer ili stereoizomer.
15. Spoj prema zahtjevu 1, naznačen time da spoj je
[image]
ili njegova sol, solvat, tautomer ili stereoizomer.
16. Sol spoja definiranog u bilo kojem od zahtjeva 9 do 15.
17. Pripravak naznačen time da sadrži spoj ili njegovu sol, solvat, tautomer ili stereoizomer prema bilo kojem prethodnom zahtjevu; i farmaceutski prihvatljiv nosač i proizvoljno barem jedno kemoterapijsko sredstvo.
18. Spoj ili njegova sol, solvat, tautomer ili stereoizomer prema bilo kojem od zahtjeva 1 do 16 naznačen time da je za upotrebu u liječenju bolesti ili stanja koje se bira iz skupa koji čine: reumatoidni artritis, osteoartritis, osteoporoza, periprotetička osteoliza, sistemska skleroza, demijelinizirajući poremećaji, multipla skleroza, sindrom Charcot Marie Tooth, amiotrofna lateralna skleroza, Alzheimerova bolest, Parkinsonova bolest, globalna ishemija, ulcerozni kolitis, Crohnova bolest, imunološka trombocitopenična purpura, ateroskleroza, sistemski eritemski lupus, mijelopriprava za autolognu transplantaciju, odbacivanje transplantata, glomerulonefritis, intersticijski nefritis, Lupus nefritis, tubularna nekroza, dijabetička nefropatija, hipertrofija bubrega, dijabetes tipa I, akutna bol, upalna bol, neuropatska bol, akutna mijeloidna leukemija, melanom, multipli mijelom, rak dojke, rak prostate, rak gušterače, rak pluća, rak jajnika, glioma, glioblastoma, neurofibromatoza, osteolitičke metastaze kostiju, metastaze mozga, gastrointestinalni stromalni tumori, te tumori velikih stanica poželjno pri čemu je navedena bolest ili stanje odabrano od: reumatoidnog artritisa, osteoartritisa, osteoporoze, periprotetičke osteolize, multiple skleroze, Alzheimerove bolesti, Parkinsonove bolesti, globalne ishemije, hipertrofije bubrega, akutne mijeloidne leukemije, melanoma, multiplog mijeloma, raka dojke, raka prostate, raka gušterače, glioblastoma, neurofibromatoze, metastaza mozga, gastrointestinalnih stromalnih tumora, i/ili je odabrano od: raka gušterače, gastrointestinalnih stromalnih tumora i tumora divovskih stanica.
19. Uporaba spoja ili njegove soli, solvata, tautomera ili stereoizomera prema bilo kojem od zahtjeva 1 do 16 naznačena time da je za proizvodnju lijeka za liječenje bolesti ili stanja koje je definirano u zahtjevu 18.
20. Spoj ili njegova sol, solvat, tautomer ili stereoizomer prema bilo kojem od zahtjeva 1 do 16, ili pripravak prema zahtjevu 17, naznačen time da je za uporabu za liječenje kronične boli, akutne boli, upalne boli, neuropatske boli, ili boli u kostima.
21. Spoj ili njegova sol, solvat, tautomer ili stereoizomer prema bilo kojem od zahtjeva 1 do 16, ili pripravak prema zahtjevu 17, naznačena time da je za uporabu za liječenje boli povezane s rakom, operacijom, ili lomom kostiju.
22. Uporaba spoja ili njegove soli, solvata, tautomera ili stereoizomera prema bilo kojem od zahtjeva 1 do 16 naznačena time da je za proizvodnju lijeka za liječenje kronične boli, akutne boli, upalne boli, neuropatske boli, boli u kostima, ili boli povezane s rakom, operacijom, ili lomom kostiju.
23. Spoj ili njegova sol, solvat, tautomer ili stereoizomer prema bilo kojem od zahtjeva 1 do 16, ili pripravak prema zahtjevu 17, naznačen time da je za upotrebu u liječenju poremećaja pohrane lizosoma.
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