JP2008545654A5 - - Google Patents
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- Publication number
- JP2008545654A5 JP2008545654A5 JP2008512476A JP2008512476A JP2008545654A5 JP 2008545654 A5 JP2008545654 A5 JP 2008545654A5 JP 2008512476 A JP2008512476 A JP 2008512476A JP 2008512476 A JP2008512476 A JP 2008512476A JP 2008545654 A5 JP2008545654 A5 JP 2008545654A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- dihydropyridine
- oxo
- fluoro
- carboxamide
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 66
- -1 2-fluoro-4- (methylthio) phenylamino Chemical group 0.000 claims 17
- 150000001408 amides Chemical class 0.000 claims 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 238000002441 X-ray diffraction Methods 0.000 claims 6
- 239000007822 coupling agent Substances 0.000 claims 5
- RWEVIPRMPFNTLO-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-3-pyridinecarboxamide Chemical compound CN1C(=O)C(C)=CC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F RWEVIPRMPFNTLO-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 claims 2
- ICXZCGXSOXMFBC-UHFFFAOYSA-N CC=1N(C(C=CC1C(=O)N)=O)C Chemical compound CC=1N(C(C=CC1C(=O)N)=O)C ICXZCGXSOXMFBC-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 230000031709 bromination Effects 0.000 claims 2
- 238000005893 bromination reaction Methods 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000004820 halides Chemical group 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 230000004968 inflammatory condition Effects 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- JZBQFLNWUKMAKK-UHFFFAOYSA-N n-(2-ethenoxyethoxy)-2-(2-fluoro-4-iodoanilino)-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound CN1C(=O)C(C)=CC(C(=O)NOCCOC=C)=C1NC1=CC=C(I)C=C1F JZBQFLNWUKMAKK-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 2
- LHWUAGUJWYLNNL-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(2-hydroxyethoxy)-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound CN1C(=O)C(C)=CC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1Cl LHWUAGUJWYLNNL-UHFFFAOYSA-N 0.000 claims 1
- AQPBVQMMZYZSLA-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(2-hydroxyethoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C(NC=2C(=CC(I)=CC=2)Cl)=C1C(=O)NOCCO AQPBVQMMZYZSLA-UHFFFAOYSA-N 0.000 claims 1
- YUIKGEAGXCVTLR-JTQLQIEISA-N 2-(2-chloro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(C)C(=O)N(C)C(NC=2C(=CC(I)=CC=2)Cl)=C1C(=O)NOC[C@@H](O)C YUIKGEAGXCVTLR-JTQLQIEISA-N 0.000 claims 1
- BOXZLZXQVSFYCS-VIFPVBQESA-N 2-(2-chloro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C(NC=2C(=CC(I)=CC=2)Cl)=C1C(=O)NOC[C@@H](O)C BOXZLZXQVSFYCS-VIFPVBQESA-N 0.000 claims 1
- NAMRBZNINMQMQI-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound CN1C(=O)C(C)=CC(C(N)=O)=C1NC1=CC=C(I)C=C1F NAMRBZNINMQMQI-UHFFFAOYSA-N 0.000 claims 1
- UFYHNTBWMOLAFZ-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOCCO UFYHNTBWMOLAFZ-UHFFFAOYSA-N 0.000 claims 1
- HZTGWVZQZRYCIJ-JTQLQIEISA-N 2-(2-fluoro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(C)C(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOC[C@@H](O)C HZTGWVZQZRYCIJ-JTQLQIEISA-N 0.000 claims 1
- SFYAWJWIRRKIGT-VIFPVBQESA-N 2-(2-fluoro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOC[C@@H](O)C SFYAWJWIRRKIGT-VIFPVBQESA-N 0.000 claims 1
- ZFURDWPQBHLAJG-UHFFFAOYSA-N 2-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)C=C(C)C(=O)N1C ZFURDWPQBHLAJG-UHFFFAOYSA-N 0.000 claims 1
- VSVSQTSOMXDCEP-UHFFFAOYSA-N 2-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)C=CC(=O)N1C VSVSQTSOMXDCEP-UHFFFAOYSA-N 0.000 claims 1
- QKZGOLDDVJWDRG-NSHDSACASA-N 2-(2-fluoro-4-methylsulfanylanilino)-n-[(2s)-2-hydroxypropoxy]-1,5-dimethyl-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOC[C@H](C)O)C=C(C)C(=O)N1C QKZGOLDDVJWDRG-NSHDSACASA-N 0.000 claims 1
- GXCXKKDPOHSMKY-JTQLQIEISA-N 2-(2-fluoro-4-methylsulfanylanilino)-n-[(2s)-2-hydroxypropoxy]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOC[C@H](C)O)C=CC(=O)N1C GXCXKKDPOHSMKY-JTQLQIEISA-N 0.000 claims 1
- RMWAGHMXANQTBX-UHFFFAOYSA-N 5-chloro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(Cl)C(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOCCO RMWAGHMXANQTBX-UHFFFAOYSA-N 0.000 claims 1
- PKGUFCFNPBLKAQ-QMMMGPOBSA-N 5-chloro-2-(2-fluoro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(Cl)C(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOC[C@@H](O)C PKGUFCFNPBLKAQ-QMMMGPOBSA-N 0.000 claims 1
- HSVJEISLTOFHPB-UHFFFAOYSA-N 5-fluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxypropoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(F)C(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOCC(O)C HSVJEISLTOFHPB-UHFFFAOYSA-N 0.000 claims 1
- OVVOSACGKCNWKT-UHFFFAOYSA-N 5-fluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(F)C(=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)NOCCO OVVOSACGKCNWKT-UHFFFAOYSA-N 0.000 claims 1
- KZPVGTXIQWCSNW-UHFFFAOYSA-N 5-fluoro-2-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)-1-methyl-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)C=C(F)C(=O)N1C KZPVGTXIQWCSNW-UHFFFAOYSA-N 0.000 claims 1
- UIYYKSUHRZUEQP-VIFPVBQESA-N 5-fluoro-2-(2-fluoro-4-methylsulfanylanilino)-n-[(2s)-2-hydroxypropoxy]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOC[C@H](C)O)C=C(F)C(=O)N1C UIYYKSUHRZUEQP-VIFPVBQESA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 0 CN(C(C(Br)=C1)=O)C(Cl)=C1C(O*)=O Chemical compound CN(C(C(Br)=C1)=O)C(Cl)=C1C(O*)=O 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68233505P | 2005-05-18 | 2005-05-18 | |
| US60/682,335 | 2005-05-18 | ||
| PCT/US2006/019108 WO2007044084A2 (en) | 2005-05-18 | 2006-05-17 | Heterocyclic inhibitors of mek and methods of use thereof |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009120619A Division JP5089649B2 (ja) | 2005-05-18 | 2009-05-19 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
| JP2012220857A Division JP5576919B2 (ja) | 2005-05-18 | 2012-10-03 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008545654A JP2008545654A (ja) | 2008-12-18 |
| JP2008545654A5 true JP2008545654A5 (enExample) | 2009-07-02 |
| JP5270336B2 JP5270336B2 (ja) | 2013-08-21 |
Family
ID=37943261
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008512476A Expired - Fee Related JP5270336B2 (ja) | 2005-05-18 | 2006-05-17 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
| JP2009120619A Expired - Fee Related JP5089649B2 (ja) | 2005-05-18 | 2009-05-19 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
| JP2012220857A Expired - Fee Related JP5576919B2 (ja) | 2005-05-18 | 2012-10-03 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009120619A Expired - Fee Related JP5089649B2 (ja) | 2005-05-18 | 2009-05-19 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
| JP2012220857A Expired - Fee Related JP5576919B2 (ja) | 2005-05-18 | 2012-10-03 | Ｍｅｋの複素環式阻害剤及びその使用方法 |
Country Status (32)
Families Citing this family (66)
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