JP2007501831A5 - - Google Patents

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Publication number: JP2007501831A5
Authority: JP; Japan
Prior art keywords: fluoro; carbonyl; pyridinecarboxamide; methylphenyl; cyclopropylamino
Prior art date: 2004-08-09
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

Application number

JP2006522975A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007501831A (ja

JP4845733B2 (ja

Filing date

2004-08-09

Publication date

2007-09-20

2003-08-11 Priority claimed from GBGB0318814.1A external-priority patent/GB0318814D0/en

2004-08-09 Application filed filed Critical

2007-02-01 Publication of JP2007501831A publication Critical patent/JP2007501831A/ja

2007-09-20 Publication of JP2007501831A5 publication Critical patent/JP2007501831A5/ja

2011-12-28 Application granted granted Critical

2011-12-28 Publication of JP4845733B2 publication Critical patent/JP4845733B2/ja

2024-08-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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125000000217 alkyl group Chemical group 0.000 claims 13
150000001875 compounds Chemical class 0.000 claims 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
229910052739 hydrogen Inorganic materials 0.000 claims 10
239000001257 hydrogen Substances 0.000 claims 10
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 8
229910052736 halogen Inorganic materials 0.000 claims 8
150000002367 halogens Chemical class 0.000 claims 8
125000003545 alkoxy group Chemical group 0.000 claims 6
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 6
150000002431 hydrogen Chemical class 0.000 claims 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
125000001072 heteroaryl group Chemical group 0.000 claims 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
125000005842 heteroatom Chemical group 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
230000000694 effects Effects 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
230000001404 mediated effect Effects 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
239000001301 oxygen Substances 0.000 claims 2
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
239000011593 sulfur Chemical group 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
-1 3-ethyl-1-piperidinyl Chemical group 0.000 claims 1
DFCMDCPZZZMKML-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxido-n-pentan-3-ylpyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)NC(CC)CC)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C DFCMDCPZZZMKML-UHFFFAOYSA-N 0.000 claims 1
WESCIQGEWIIPRB-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxido-n-propylpyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)NCCC)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C WESCIQGEWIIPRB-UHFFFAOYSA-N 0.000 claims 1
WIYUGLNMUKOBJU-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2,2-dimethylpropyl)-1-oxidopyridin-1-ium-3-carboxamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=[N+]1[O-] WIYUGLNMUKOBJU-UHFFFAOYSA-N 0.000 claims 1
FJJONJDJIDGXOS-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2-methylbutan-2-yl)-1-oxidopyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)NC(C)(C)CC)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C FJJONJDJIDGXOS-UHFFFAOYSA-N 0.000 claims 1
SFFZRBYPYAXZLY-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2-methylbutan-2-yl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC(C)(C)CC)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C SFFZRBYPYAXZLY-UHFFFAOYSA-N 0.000 claims 1
MESZBQFBSFHEEG-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2-methylpropyl)-1-oxidopyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)NCC(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C MESZBQFBSFHEEG-UHFFFAOYSA-N 0.000 claims 1
SCMUUBWYJOXVQD-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2,5-dimethylphenyl)methyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound CC1=CC=C(C)C(CNC(=O)C=2C=[N+]([O-])C(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)=CC=2)=C1 SCMUUBWYJOXVQD-UHFFFAOYSA-N 0.000 claims 1
DQFUUKFVEQZPQQ-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2-ethylphenyl)methyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound CCC1=CC=CC=C1CNC(=O)C(C=[N+]1[O-])=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C DQFUUKFVEQZPQQ-UHFFFAOYSA-N 0.000 claims 1
MSHRGLRYOATXIV-CQSZACIVSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2r)-3,3-dimethylbutan-2-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)N[C@H](C)C(C)(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C MSHRGLRYOATXIV-CQSZACIVSA-N 0.000 claims 1
PYUKVRINYBQHCX-CQSZACIVSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2r)-3,3-dimethylbutan-2-yl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N[C@H](C)C(C)(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C PYUKVRINYBQHCX-CQSZACIVSA-N 0.000 claims 1
XDEQCYKIFPIEAL-CQSZACIVSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2r)-3-methylbutan-2-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)N[C@H](C)C(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C XDEQCYKIFPIEAL-CQSZACIVSA-N 0.000 claims 1
KTBQVLJAADKZTA-CQSZACIVSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2r)-3-methylbutan-2-yl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N[C@H](C)C(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C KTBQVLJAADKZTA-CQSZACIVSA-N 0.000 claims 1
HJAKOLLDSZLBIM-LBPRGKRZSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2s)-1-methoxypropan-2-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical class [O-][N+]1=CC(C(=O)N[C@@H](C)COC)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C HJAKOLLDSZLBIM-LBPRGKRZSA-N 0.000 claims 1
MSHRGLRYOATXIV-AWEZNQCLSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2s)-3,3-dimethylbutan-2-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)N[C@@H](C)C(C)(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C MSHRGLRYOATXIV-AWEZNQCLSA-N 0.000 claims 1
PYUKVRINYBQHCX-AWEZNQCLSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2s)-3,3-dimethylbutan-2-yl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N[C@@H](C)C(C)(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C PYUKVRINYBQHCX-AWEZNQCLSA-N 0.000 claims 1
XDEQCYKIFPIEAL-AWEZNQCLSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2s)-3-methylbutan-2-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC(C(=O)N[C@@H](C)C(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C XDEQCYKIFPIEAL-AWEZNQCLSA-N 0.000 claims 1
KTBQVLJAADKZTA-AWEZNQCLSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(2s)-3-methylbutan-2-yl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N[C@@H](C)C(C)C)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C KTBQVLJAADKZTA-AWEZNQCLSA-N 0.000 claims 1
IGZRKBXWJWDPEO-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(3,4-dimethylphenyl)methyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound C1=C(C)C(C)=CC=C1CNC(=O)C(C=[N+]1[O-])=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C IGZRKBXWJWDPEO-UHFFFAOYSA-N 0.000 claims 1
MOHQCDJFKYFECU-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(3,4-dimethylphenyl)methyl]pyridine-3-carboxamide Chemical compound C1=C(C)C(C)=CC=C1CNC(=O)C1=CC=C(C=2C(=C(F)C=C(C=2)C(=O)NC2CC2)C)N=C1 MOHQCDJFKYFECU-UHFFFAOYSA-N 0.000 claims 1
HFIGQSSOGGAORT-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[(3,5-dimethylphenyl)methyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound CC1=CC(C)=CC(CNC(=O)C=2C=[N+]([O-])C(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)=CC=2)=C1 HFIGQSSOGGAORT-UHFFFAOYSA-N 0.000 claims 1
ZWGJNQPKXGGUPF-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical class CC1=C(F)C=C(C(=O)NC2CC2)C=C1C([N+](=C1)[O-])=CC=C1C(=O)NCC1=CC(C(F)(F)F)=CC=C1F ZWGJNQPKXGGUPF-UHFFFAOYSA-N 0.000 claims 1
PDAASRZVZWUOGC-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-[[5-fluoro-2-(trifluoromethyl)phenyl]methyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical class CC1=C(F)C=C(C(=O)NC2CC2)C=C1C([N+](=C1)[O-])=CC=C1C(=O)NCC1=CC(F)=CC=C1C(F)(F)F PDAASRZVZWUOGC-UHFFFAOYSA-N 0.000 claims 1
CJADNGHARCVQSY-UHFFFAOYSA-N 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-pentan-3-ylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC(CC)CC)=CC=C1C1=CC(C(=O)NC2CC2)=CC(F)=C1C CJADNGHARCVQSY-UHFFFAOYSA-N 0.000 claims 1
KKYABQBFGDZVNQ-UHFFFAOYSA-N 6-[5-[(cyclopropylamino)-oxomethyl]-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)-3-pyridinecarboxamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1 KKYABQBFGDZVNQ-UHFFFAOYSA-N 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
102000004127 Cytokines Human genes 0.000 claims 1
108090000695 Cytokines Proteins 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000000034 method Methods 0.000 claims 1
BTWRTPSUYRKNOG-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethyl]-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C(C=[N+]1[O-])=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1CC1 BTWRTPSUYRKNOG-UHFFFAOYSA-N 0.000 claims 1
IJNAYAZAIAYOHP-UHFFFAOYSA-N n-[[2,4-bis(trifluoromethyl)phenyl]methyl]-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1C([N+](=C1)[O-])=CC=C1C(=O)NCC1=CC=C(C(F)(F)F)C=C1C(F)(F)F IJNAYAZAIAYOHP-UHFFFAOYSA-N 0.000 claims 1
XWSRZGAHUYOSQY-UHFFFAOYSA-N n-tert-butyl-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)NC(C)(C)C)C=[N+]1[O-] XWSRZGAHUYOSQY-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1

JP2006522975A 2003-08-11 2004-08-09 Ｐ３８キナーゼ阻害剤としての３−アミノカルボニル、６−フェニル置換ピリジン−１−オキシド Expired - Lifetime JP4845733B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB0318814.1		2003-08-11
GBGB0318814.1A GB0318814D0 (en)	2003-08-11	2003-08-11	Novel compounds
PCT/EP2004/008972 WO2005014550A1 (en)	2003-08-11	2004-08-09	3- aminocarbonyl, 6-phenyl substituted pyridine-1-oxides as p38 kinase inhibitors

Publications (3)

Publication Number	Publication Date
JP2007501831A JP2007501831A (ja)	2007-02-01
JP2007501831A5 true JP2007501831A5 (2)	2007-09-20
JP4845733B2 JP4845733B2 (ja)	2011-12-28

Family

ID=27840005

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2006522975A Expired - Lifetime JP4845733B2 (ja)	2003-08-11	2004-08-09	Ｐ３８キナーゼ阻害剤としての３−アミノカルボニル、６−フェニル置換ピリジン−１−オキシド

Country Status (6)

Country	Link
US (1)	US7838540B2 (2)
EP (1)	EP1654235B1 (2)
JP (1)	JP4845733B2 (2)
ES (1)	ES2400348T3 (2)
GB (1)	GB0318814D0 (2)
WO (1)	WO2005014550A1 (2)

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WO2012149106A1 (en)	2011-04-29	2012-11-01	The Board Of Trustees Of The Leland Stanford Junior University	Compositions and methods for increasing proliferation of adult salivary stem cells
IN2014KN02981A (2) *	2012-07-17	2015-05-08	Glaxosmithkline Llc
WO2014160185A2 (en)	2013-03-14	2014-10-02	The Board Of Trustees Of The Leland Stanford Junior University	Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof
WO2017054765A1 (zh) *	2015-09-30	2017-04-06	石药集团中奇制药技术（石家庄）有限公司	苯甲酰胺类衍生物
WO2019071144A1 (en)	2017-10-05	2019-04-11	Fulcrum Therapeutics, Inc.	USE OF P38 INHIBITORS TO REDUCE DUX4 EXPRESSION
US10342786B2 (en)	2017-10-05	2019-07-09	Fulcrum Therapeutics, Inc.	P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD

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2003
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2004
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- 2004-08-09 US US10/568,121 patent/US7838540B2/en active Active
- 2004-08-09 EP EP04763980A patent/EP1654235B1/en not_active Expired - Lifetime
- 2004-08-09 WO PCT/EP2004/008972 patent/WO2005014550A1/en not_active Ceased

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