CA2613015C - Pyrrolo [2, 3-b] pyridine derivatives as protein kinase inhibitors - Google Patents
Pyrrolo [2, 3-b] pyridine derivatives as protein kinase inhibitors Download PDFInfo
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- CA2613015C CA2613015C CA2613015A CA2613015A CA2613015C CA 2613015 C CA2613015 C CA 2613015C CA 2613015 A CA2613015 A CA 2613015A CA 2613015 A CA2613015 A CA 2613015A CA 2613015 C CA2613015 C CA 2613015C
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- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical class C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 title description 22
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 334
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- 201000010099 disease Diseases 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 937
- 239000001257 hydrogen Substances 0.000 claims description 936
- 125000001153 fluoro group Chemical group F* 0.000 claims description 754
- 125000000217 alkyl group Chemical group 0.000 claims description 460
- 150000002431 hydrogen Chemical class 0.000 claims description 445
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 360
- 229910020008 S(O) Inorganic materials 0.000 claims description 285
- 229910052736 halogen Inorganic materials 0.000 claims description 281
- 125000004414 alkyl thio group Chemical group 0.000 claims description 260
- 150000002367 halogens Chemical class 0.000 claims description 212
- 125000001072 heteroaryl group Chemical group 0.000 claims description 209
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 182
- 125000003107 substituted aryl group Chemical group 0.000 claims description 132
- 125000001424 substituent group Chemical group 0.000 claims description 118
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 105
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 105
- 150000003839 salts Chemical class 0.000 claims description 85
- 125000005843 halogen group Chemical group 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 66
- -1 C1-C6 alkyl carbon Chemical group 0.000 claims description 63
- 229910052799 carbon Inorganic materials 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
- 238000006467 substitution reaction Methods 0.000 claims description 49
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
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- 150000001336 alkenes Chemical class 0.000 claims description 8
- 150000001345 alkine derivatives Chemical class 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 42
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- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 6
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- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
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- 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 2
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
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- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 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 2
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- 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 1
- QGVRCVIZDLXMPO-UHFFFAOYSA-N 4-butoxy-n-[2,4-difluoro-3-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl]benzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC=CN=C3NC=2)=C1F QGVRCVIZDLXMPO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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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