IL222498A - Compounds and methods for kinase modulation and indications therefor - Google Patents

Info

Publication number

IL222498A

IL222498A IL222498A IL22249812A IL222498A IL 222498 A IL222498 A IL 222498A IL 222498 A IL222498 A IL 222498A IL 22249812 A IL22249812 A IL 22249812A IL 222498 A IL222498 A IL 222498A

Authority

IL

Israel

Prior art keywords

fluoro

pyridyl

formula

amino

pyrrolo

Prior art date

2010-04-21

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 881
• 238000000034 method Methods 0.000 title description 37
• 108091000080 Phosphotransferase Proteins 0.000 title description 36
• 102000020233 phosphotransferase Human genes 0.000 title description 36
• 125000001153 fluoro group Chemical group F* 0.000 claims description 1111
• 125000000217 alkyl group Chemical group 0.000 claims description 836
• 125000003545 alkoxy group Chemical group 0.000 claims description 627
• 229910052739 hydrogen Inorganic materials 0.000 claims description 623
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 405
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 298
• -1 4-pyrazolyl Chemical group 0.000 claims description 219
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 171
• 150000003839 salts Chemical class 0.000 claims description 120
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
• 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 description 94
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 94
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 89
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 86
• 239000012453 solvate Substances 0.000 claims description 82
• 125000001246 bromo group Chemical group Br* 0.000 claims description 68
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
• 239000000203 mixture Substances 0.000 claims description 47
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 201000010099 disease Diseases 0.000 claims description 30
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 13
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 9
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• 239000003814 drug Substances 0.000 claims description 8
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
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• 229940127089 cytotoxic agent Drugs 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 206010065390 Inflammatory pain Diseases 0.000 claims description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
• 208000005298 acute pain Diseases 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
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• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 3
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• 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
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• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 3
• 208000007569 Giant Cell Tumors Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• 208000028622 Immune thrombocytopenia Diseases 0.000 claims description 3
• 208000005777 Lupus Nephritis Diseases 0.000 claims description 3
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 3
• 208000001132 Osteoporosis Diseases 0.000 claims description 3
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• 206010052306 Periprosthetic osteolysis Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 206010038468 Renal hypertrophy Diseases 0.000 claims description 3
• 206010038540 Renal tubular necrosis Diseases 0.000 claims description 3
• 201000009594 Systemic Scleroderma Diseases 0.000 claims description 3
• 206010042953 Systemic sclerosis Diseases 0.000 claims description 3
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 3
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 3
• 201000006334 interstitial nephritis Diseases 0.000 claims description 3
• 208000028867 ischemia Diseases 0.000 claims description 3
• 201000008627 kidney hypertrophy Diseases 0.000 claims description 3
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• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 238000001356 surgical procedure Methods 0.000 claims description 3
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
• 238000002054 transplantation Methods 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 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 description 2
• 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 description 2
• 206010018338 Glioma Diseases 0.000 claims description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
• 206010027452 Metastases to bone Diseases 0.000 claims description 2
• 208000009905 Neurofibromatoses Diseases 0.000 claims description 2
• 206010033128 Ovarian cancer Diseases 0.000 claims description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
• 229930012538 Paclitaxel Natural products 0.000 claims description 2
• 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 description 2
• 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 description 2
• VLMRYRMQQFHGAS-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]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)F)=CC=C1NC1CCC(F)CC1 VLMRYRMQQFHGAS-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• ZGOLZYGKOPQXNE-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)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=C1NC(C=N1)=CC=C1C1CC1 ZGOLZYGKOPQXNE-UHFFFAOYSA-N 0.000 claims description 2
• VMCQDPIBUAGJRJ-WOJBJXKFSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,2r)-2-hydroxycyclohexyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound O[C@@H]1CCCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(=CC=3)C3CC3)=CC=1)F)=CN2 VMCQDPIBUAGJRJ-WOJBJXKFSA-N 0.000 claims description 2
• 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 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 2
• 229960005277 gemcitabine Drugs 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 201000005202 lung cancer Diseases 0.000 claims description 2
• 208000020816 lung neoplasm Diseases 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 201000004931 neurofibromatosis Diseases 0.000 claims description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 229960001592 paclitaxel Drugs 0.000 claims description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 19
• 208000016192 Demyelinating disease Diseases 0.000 claims 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
• 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
• FKJOLNNYYKMHTO-UHFFFAOYSA-N 4-[[5-[6-[(4,4-difluorocyclohexyl)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=1NC1CCC(F)(F)CC1 FKJOLNNYYKMHTO-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
• 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
• 208000010392 Bone Fractures Diseases 0.000 claims 1
• 206010006002 Bone pain Diseases 0.000 claims 1
• 208000003174 Brain Neoplasms Diseases 0.000 claims 1
• 208000000094 Chronic Pain Diseases 0.000 claims 1
• 208000015439 Lysosomal storage disease Diseases 0.000 claims 1
• 206010059282 Metastases to central nervous system Diseases 0.000 claims 1
• SSSWAWRKVQBQCT-UHFFFAOYSA-N [2-chloro-6-(cyclohexylamino)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=C1NC1CCCCC1 SSSWAWRKVQBQCT-UHFFFAOYSA-N 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
• 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
• 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
• MTKHXWNCEKNMNS-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propan-2-ylamino)-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(NC(C)C)=C12 MTKHXWNCEKNMNS-UHFFFAOYSA-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
• 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
• WCMSACDKVXDZHV-UHFFFAOYSA-N [4-(cyclobutylamino)-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(NC3CCC3)=C12 WCMSACDKVXDZHV-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
• 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
• BMGUGRXFBFRZEV-UHFFFAOYSA-N [4-(cyclohexylamino)-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(NC3CCCCC3)=C12 BMGUGRXFBFRZEV-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
• 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
• 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
• 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
• 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 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
• KOCJZTRVGCGTEF-HUUCEWRRSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,3r)-3-hydroxycyclohexyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1[C@H](O)CCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 KOCJZTRVGCGTEF-HUUCEWRRSA-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
• 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
• QOTAVWBOEXMGIL-RTBURBONSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,2r)-2-hydroxycyclopentyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound O[C@@H]1CCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(=CC=3)C3CC3)=CC=1)F)=CN2 QOTAVWBOEXMGIL-RTBURBONSA-N 0.000 claims 1
• ICYYVDYWKKAIOX-NVXWUHKLSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,3r)-3-hydroxycyclohexyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1[C@H](O)CCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(=CC=3)C3CC3)=CC=1)F)=CN2 ICYYVDYWKKAIOX-NVXWUHKLSA-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
• 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
• 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
• 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
• 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
• 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
• 239000000126 substance Substances 0.000 claims 1
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• 150000002431 hydrogen Chemical group 0.000 description 168
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 99
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 81
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• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 23
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