CA2521228A1 - Biphenyl carboxylic amide p38 kinase inhibitors - Google Patents
Biphenyl carboxylic amide p38 kinase inhibitors Download PDFInfo
- Publication number
- CA2521228A1 CA2521228A1 CA002521228A CA2521228A CA2521228A1 CA 2521228 A1 CA2521228 A1 CA 2521228A1 CA 002521228 A CA002521228 A CA 002521228A CA 2521228 A CA2521228 A CA 2521228A CA 2521228 A1 CA2521228 A1 CA 2521228A1
- Authority
- CA
- Canada
- Prior art keywords
- 6alkyl
- optionally substituted
- groups
- methyl
- hydrogen
- 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.)
- Abandoned
Links
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title claims abstract description 30
- 229940043355 kinase inhibitor Drugs 0.000 title abstract description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 title abstract description 3
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 239000003814 drug Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 65
- -1 CONHR9 Chemical group 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical class 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 239000011593 sulfur Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 14
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
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PCT/EP2004/003774 WO2004089874A1 (en) | 2003-04-09 | 2004-04-07 | Biphenyl carboxylic amide p38 kinase inhibitors |
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DK1474395T3 (da) | 2002-02-12 | 2008-02-11 | Smithkline Beecham Corp | Nicotinamidderivater, der er nyttige som p38-inhibitorer |
TWI263497B (en) * | 2002-03-29 | 2006-10-11 | Lilly Co Eli | Pyridinoylpiperidines as 5-HT1F agonists |
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CA2574600C (en) * | 2004-07-23 | 2010-08-31 | Pfizer Inc. | Pyridine derivatives |
TW200628153A (en) * | 2004-10-05 | 2006-08-16 | Smithkline Beecham Corp | Novel compounds |
RU2452729C2 (ru) * | 2005-09-16 | 2012-06-10 | Арроу Терапьютикс Лимитед | Бифенильные производные и их применение при лечении гепатита с |
CA2621364A1 (en) * | 2005-09-16 | 2007-03-22 | Arrow Therapeutics Limited | Biphenyl derivatives and their use in treating hepatitis c |
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NZ596161A (en) * | 2009-04-02 | 2013-11-29 | Colucid Pharmaceuticals Inc | Composition of 2,4,6-trifluoro-n-[6-(1-methyl-piperidin-4-carbonyl)-pyridin-2-yl]-benzamide |
US8697876B2 (en) | 2010-04-02 | 2014-04-15 | Colucid Pharmaceuticals, Inc. | Compositions and methods of synthesis of pyridinolypiperidine 5-HT1F agonists |
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2004
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- 2004-04-07 WO PCT/EP2004/003774 patent/WO2004089874A1/en active Application Filing
- 2004-04-07 EP EP04726134A patent/EP1608616A1/en not_active Withdrawn
- 2004-04-07 AU AU2004228199A patent/AU2004228199A1/en not_active Abandoned
- 2004-04-07 JP JP2006505071A patent/JP2006523194A/ja active Pending
- 2004-04-07 CA CA002521228A patent/CA2521228A1/en not_active Abandoned
- 2004-04-07 US US10/551,502 patent/US7572790B2/en not_active Expired - Fee Related
- 2004-04-07 MX MXPA05010521A patent/MXPA05010521A/es not_active Application Discontinuation
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2005
- 2005-08-29 ZA ZA200506919A patent/ZA200506919B/en unknown
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MXPA05010521A (es) | 2005-12-14 |
AU2004228199A1 (en) | 2004-10-21 |
US7572790B2 (en) | 2009-08-11 |
WO2004089874A1 (en) | 2004-10-21 |
ZA200506919B (en) | 2006-11-29 |
GB0308186D0 (en) | 2003-05-14 |
JP2006523194A (ja) | 2006-10-12 |
BRPI0408727A (pt) | 2006-03-07 |
EP1608616A1 (en) | 2005-12-28 |
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