ES2371397T3 - Derivados de pirrolo[2,3-b]piridina como inhibidores de proteínas cinasas. - Google Patents
Derivados de pirrolo[2,3-b]piridina como inhibidores de proteínas cinasas. Download PDFInfo
- Publication number
- ES2371397T3 ES2371397T3 ES06773861T ES06773861T ES2371397T3 ES 2371397 T3 ES2371397 T3 ES 2371397T3 ES 06773861 T ES06773861 T ES 06773861T ES 06773861 T ES06773861 T ES 06773861T ES 2371397 T3 ES2371397 T3 ES 2371397T3
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- ES
- Spain
- Prior art keywords
- phenyl
- pyrrolo
- pyridin
- nhc
- difluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 108090000623 proteins and genes Proteins 0.000 title description 19
- 102000004169 proteins and genes Human genes 0.000 title description 16
- 239000003112 inhibitor Substances 0.000 title description 11
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 465
- 125000001424 substituent group Chemical group 0.000 claims abstract description 119
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 108
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 86
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 63
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 52
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 51
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 40
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000002367 halogens Chemical class 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 8
- 150000001336 alkenes Chemical class 0.000 claims abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 50
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 23
- 125000005843 halogen group Chemical group 0.000 claims abstract 16
- -1 C1-C6 alkyl carbon Chemical group 0.000 claims description 186
- 238000002360 preparation method Methods 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 59
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 56
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 50
- 201000010099 disease Diseases 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 238000006467 substitution reaction Methods 0.000 claims description 36
- 101100381978 Mus musculus Braf gene Proteins 0.000 claims description 34
- KKVYYGGCHJGEFJ-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-6-methyl-5-n-[3-(7h-purin-6-yl)pyridin-2-yl]isoquinoline-1,5-diamine Chemical compound N=1C=CC2=C(NC=3C(=CC=CN=3)C=3C=4N=CNC=4N=CN=3)C(C)=CC=C2C=1NC1=CC=C(Cl)C=C1 KKVYYGGCHJGEFJ-UHFFFAOYSA-N 0.000 claims description 33
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims description 29
- 102000001253 Protein Kinase Human genes 0.000 claims description 28
- 230000000694 effects Effects 0.000 claims description 28
- 108060006633 protein kinase Proteins 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 26
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 230000035772 mutation Effects 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 15
- 108010077182 raf Kinases Proteins 0.000 claims description 15
- 102000009929 raf Kinases Human genes 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 12
- 230000001225 therapeutic effect Effects 0.000 claims description 12
- MVKWDNQCWQPTST-UHFFFAOYSA-N (3-amino-2,6-difluorophenyl)-(5-chloro-1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound NC1=CC=C(F)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F MVKWDNQCWQPTST-UHFFFAOYSA-N 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 10
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 8
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 7
- TVFGCDQPUZGXMQ-UHFFFAOYSA-N n-[3-(5-bromo-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(Br)=CN=C3NC=2)=C1F TVFGCDQPUZGXMQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- BQQFXHJUISSMEC-UHFFFAOYSA-N (3-amino-2,6-difluorophenyl)-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound NC1=CC=C(F)C(C(=O)C=2C3=CC(Br)=CN=C3NC=2)=C1F BQQFXHJUISSMEC-UHFFFAOYSA-N 0.000 claims description 5
- HRRABEXPCDTYOU-UHFFFAOYSA-N (3-amino-2,6-difluorophenyl)-(5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=NC=CC=2)=C1F HRRABEXPCDTYOU-UHFFFAOYSA-N 0.000 claims description 5
- VLMVTMCKGVRPGT-UHFFFAOYSA-N (3-amino-2,6-difluorophenyl)-[5-(4-chlorophenyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]methanone Chemical compound NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F VLMVTMCKGVRPGT-UHFFFAOYSA-N 0.000 claims description 5
- 206010018338 Glioma Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 208000032612 Glial tumor Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- HWZXAINJEXHUQF-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2C(=C(C(=O)C=3C4=CC=CN=C4NC=3)C(F)=CC=2)F)=C1 HWZXAINJEXHUQF-UHFFFAOYSA-N 0.000 claims description 4
- LHBXDLRFMVOSCZ-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]thiophene-2-sulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=CS1 LHBXDLRFMVOSCZ-UHFFFAOYSA-N 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
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- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- BWVUSPPFFKJBAD-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-2,4-dimethoxybenzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC=CN=C3NC=2)=C1F BWVUSPPFFKJBAD-UHFFFAOYSA-N 0.000 claims description 3
- KMZWSNWGLJBGGH-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C(=C(C(=O)C=3C4=CC=CN=C4NC=3)C(F)=CC=2)F)=C1 KMZWSNWGLJBGGH-UHFFFAOYSA-N 0.000 claims description 3
- BZKCRNBHOYQGRL-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-2,5-dimethylthiophene-3-sulfonamide Chemical compound S1C(C)=CC(S(=O)(=O)NC=2C(=C(C(=O)C=3C4=CC=CN=C4NC=3)C(F)=CC=2)F)=C1C BZKCRNBHOYQGRL-UHFFFAOYSA-N 0.000 claims description 3
- AOOQIKHYJFCPHD-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 AOOQIKHYJFCPHD-UHFFFAOYSA-N 0.000 claims description 3
- PQZSWPJQHBXXQE-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC=CN=C3NC=2)=C1F PQZSWPJQHBXXQE-UHFFFAOYSA-N 0.000 claims description 3
- INPBUXXFTHBPOL-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]-3,5-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC=2C(=C(C(=O)C=3C4=CC(Cl)=CN=C4NC=3)C(F)=CC=2)F)=C1 INPBUXXFTHBPOL-UHFFFAOYSA-N 0.000 claims description 3
- GUOFQSHXQFNMSQ-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 GUOFQSHXQFNMSQ-UHFFFAOYSA-N 0.000 claims description 3
- AODBPKRKRLUCPK-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F AODBPKRKRLUCPK-UHFFFAOYSA-N 0.000 claims description 3
- VPGAMYMFGAJMSL-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F VPGAMYMFGAJMSL-UHFFFAOYSA-N 0.000 claims description 3
- QBFSPXMLKXRYHL-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F QBFSPXMLKXRYHL-UHFFFAOYSA-N 0.000 claims description 3
- TWMSZAZIWAFHJI-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=CC=C1 TWMSZAZIWAFHJI-UHFFFAOYSA-N 0.000 claims description 3
- GBHDVJBTTQEMCN-UHFFFAOYSA-N n-[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2-fluorophenyl]benzenesulfonamide Chemical compound C1=CC=C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)C(F)=C1NS(=O)(=O)C1=CC=CC=C1 GBHDVJBTTQEMCN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- ANKLZKQLTLTQLA-UHFFFAOYSA-N (3-amino-6-chloro-2-fluorophenyl)-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound NC1=CC=C(Cl)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F ANKLZKQLTLTQLA-UHFFFAOYSA-N 0.000 claims description 2
- DOFOKHVWOGFQPK-UHFFFAOYSA-N 2-cyano-n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C#N DOFOKHVWOGFQPK-UHFFFAOYSA-N 0.000 claims description 2
- CEAMNSBIDMDCIE-UHFFFAOYSA-N 3,4-dichloro-n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 CEAMNSBIDMDCIE-UHFFFAOYSA-N 0.000 claims description 2
- JIYBENCDPFFGFQ-UHFFFAOYSA-N 3-[3-[2,6-difluoro-3-(propylsulfonylamino)benzoyl]-1h-pyrrolo[2,3-b]pyridin-5-yl]benzoic acid Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=C(C=CC=2)C(O)=O)=C1F JIYBENCDPFFGFQ-UHFFFAOYSA-N 0.000 claims description 2
- FWLNBJYQDZJLOL-UHFFFAOYSA-N 3-cyano-n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=CC(C#N)=C1 FWLNBJYQDZJLOL-UHFFFAOYSA-N 0.000 claims description 2
- CBWKNPFPFBLMDT-UHFFFAOYSA-N 4-chloro-n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]benzenesulfonamide Chemical compound FC1=C(C(=O)C=2C3=CC=CN=C3NC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 CBWKNPFPFBLMDT-UHFFFAOYSA-N 0.000 claims description 2
- HBKNSUOCZYKZPE-UHFFFAOYSA-N N1C(C)=CN=C1C1=CN=C(NC=C2C(=O)C=3C(=C(N)C=CC=3F)F)C2=C1 Chemical compound N1C(C)=CN=C1C1=CN=C(NC=C2C(=O)C=3C(=C(N)C=CC=3F)F)C2=C1 HBKNSUOCZYKZPE-UHFFFAOYSA-N 0.000 claims description 2
- JOCBOSWOGIDFOI-UHFFFAOYSA-N NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(=CC=2)C(=O)N2CCOCC2)=C1F Chemical compound NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(=CC=2)C(=O)N2CCOCC2)=C1F JOCBOSWOGIDFOI-UHFFFAOYSA-N 0.000 claims description 2
- LHLKLXVPLSWZKU-UHFFFAOYSA-N NC1=CC=CC(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F Chemical compound NC1=CC=CC(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F LHLKLXVPLSWZKU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002619 bicyclic group Chemical group 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- UOTLSRGPYREYDK-UHFFFAOYSA-N methyl 5-[[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]sulfamoyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC=CN=C3NC=2)=C1F UOTLSRGPYREYDK-UHFFFAOYSA-N 0.000 claims description 2
- WBWXUOPQWBWLNE-UHFFFAOYSA-N methyl 5-[[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]sulfamoyl]-2-methylfuran-3-carboxylate Chemical compound O1C(C)=C(C(=O)OC)C=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F WBWXUOPQWBWLNE-UHFFFAOYSA-N 0.000 claims description 2
- YVOZPWCVBDTZFH-UHFFFAOYSA-N methyl 5-[[3-(5-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]sulfamoyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(Cl)=CN=C3NC=2)=C1F YVOZPWCVBDTZFH-UHFFFAOYSA-N 0.000 claims description 2
- MXFVNYXHSJMRJS-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-1,3-benzothiazole-6-sulfonamide Chemical compound C1=CC=C2C(C(=O)C3=C(F)C(NS(=O)(=O)C=4C=C5SC=NC5=CC=4)=CC=C3F)=CNC2=N1 MXFVNYXHSJMRJS-UHFFFAOYSA-N 0.000 claims description 2
- PDYWABCMBQVUKO-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC=CN=C3NC=2)=C1F PDYWABCMBQVUKO-UHFFFAOYSA-N 0.000 claims description 2
- PVAOWASURYEKIM-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC=CN=C3NC=2)=C1F PVAOWASURYEKIM-UHFFFAOYSA-N 0.000 claims description 2
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- BWPALGLCTHDSDG-UHFFFAOYSA-N n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]-3-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=C(C(=O)C=3C4=CC=CN=C4NC=3)C(F)=CC=2)F)=C1 BWPALGLCTHDSDG-UHFFFAOYSA-N 0.000 claims description 2
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PCT/US2006/024524 WO2007002433A1 (en) | 2005-06-22 | 2006-06-21 | Pyrrolo [2, 3-b] pyridine derivatives as protein kinase inhibitors |
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