CA2420024A1 - Fused pyrazole derivatives being protein kinase inhibitors - Google Patents
Fused pyrazole derivatives being protein kinase inhibitors Download PDFInfo
- Publication number
- CA2420024A1 CA2420024A1 CA002420024A CA2420024A CA2420024A1 CA 2420024 A1 CA2420024 A1 CA 2420024A1 CA 002420024 A CA002420024 A CA 002420024A CA 2420024 A CA2420024 A CA 2420024A CA 2420024 A1 CA2420024 A1 CA 2420024A1
- Authority
- CA
- Canada
- Prior art keywords
- fluorophenyl
- pyrazolo
- formula
- pyridin
- compound
- 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
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract description 4
- 239000003909 protein kinase inhibitor Substances 0.000 title abstract description 4
- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 404
- 150000003839 salts Chemical class 0.000 claims abstract description 60
- 239000012453 solvate Substances 0.000 claims abstract description 50
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- -1 C2-5alkenyl Chemical group 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 57
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 53
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 230000000694 effects Effects 0.000 claims description 40
- 230000001404 mediated effect Effects 0.000 claims description 40
- 102000002569 MAP Kinase Kinase 4 Human genes 0.000 claims description 38
- 108010068304 MAP Kinase Kinase 4 Proteins 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical group 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 24
- 102000004127 Cytokines Human genes 0.000 claims description 23
- 108090000695 Cytokines Proteins 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 21
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical group C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 5
- JIIWFBWSAHKMIA-UHFFFAOYSA-N 3-[[4-[2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound OCCCNC1=NC=CC(C2=C3C=CC(=CN3N=C2C=2C=CC(F)=CC=2)C(F)(F)F)=N1 JIIWFBWSAHKMIA-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
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- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 89
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 150000001412 amines Chemical class 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 64
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- 239000002904 solvent Substances 0.000 description 60
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
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- 238000001914 filtration Methods 0.000 description 46
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- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 42
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 229960004132 diethyl ether Drugs 0.000 description 28
- 230000002829 reductive effect Effects 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| GB0020576.5 | 2000-08-22 | ||
| GBGB0020556.7A GB0020556D0 (en) | 2000-08-22 | 2000-08-22 | Fused pyrazole derivatives |
| GB0020576A GB0020576D0 (en) | 2000-08-22 | 2000-08-22 | Fused pyrazole derivatives |
| GB0020556.7 | 2000-08-22 | ||
| PCT/GB2001/003783 WO2002016359A1 (en) | 2000-08-22 | 2001-08-22 | Fused pyrazole derivatives being protein kinase inhibitors |
Publications (1)
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| CA2420024A1 true CA2420024A1 (en) | 2002-02-28 |
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| CA002420024A Abandoned CA2420024A1 (en) | 2000-08-22 | 2001-08-22 | Fused pyrazole derivatives being protein kinase inhibitors |
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-
2001
- 2001-08-21 PE PE2001000842A patent/PE20020506A1/es not_active Application Discontinuation
- 2001-08-22 WO PCT/GB2001/003783 patent/WO2002016359A1/en not_active Ceased
- 2001-08-22 BR BR0113448-5A patent/BR0113448A/pt not_active Application Discontinuation
- 2001-08-22 ES ES01960928T patent/ES2259331T3/es not_active Expired - Lifetime
- 2001-08-22 HU HU0400757A patent/HUP0400757A2/hu unknown
- 2001-08-22 DE DE60117568T patent/DE60117568T2/de not_active Expired - Fee Related
- 2001-08-22 UY UY26899A patent/UY26899A1/es unknown
- 2001-08-22 KR KR10-2003-7002634A patent/KR20030040419A/ko not_active Withdrawn
- 2001-08-22 IL IL15440201A patent/IL154402A0/xx unknown
- 2001-08-22 JP JP2002521460A patent/JP2004506736A/ja active Pending
- 2001-08-22 AU AU2001282318A patent/AU2001282318A1/en not_active Abandoned
- 2001-08-22 AT AT01960928T patent/ATE318814T1/de not_active IP Right Cessation
- 2001-08-22 AR ARP010104007A patent/AR034261A1/es unknown
- 2001-08-22 EP EP01960928A patent/EP1311507B1/en not_active Expired - Lifetime
- 2001-08-22 CA CA002420024A patent/CA2420024A1/en not_active Abandoned
- 2001-08-22 PL PL36213001A patent/PL362130A1/xx not_active Application Discontinuation
- 2001-08-22 MX MXPA03001593A patent/MXPA03001593A/es unknown
- 2001-08-22 US US10/362,146 patent/US7166597B2/en not_active Expired - Fee Related
-
2003
- 2003-02-19 NO NO20030779A patent/NO20030779L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL362130A1 (en) | 2004-10-18 |
| AU2001282318A1 (en) | 2002-03-04 |
| KR20030040419A (ko) | 2003-05-22 |
| EP1311507B1 (en) | 2006-03-01 |
| HUP0400757A2 (hu) | 2004-07-28 |
| DE60117568T2 (de) | 2006-08-24 |
| BR0113448A (pt) | 2003-06-17 |
| NO20030779D0 (no) | 2003-02-19 |
| NO20030779L (no) | 2003-04-07 |
| EP1311507A1 (en) | 2003-05-21 |
| AR034261A1 (es) | 2004-02-18 |
| US20040053942A1 (en) | 2004-03-18 |
| ATE318814T1 (de) | 2006-03-15 |
| US7166597B2 (en) | 2007-01-23 |
| IL154402A0 (en) | 2003-09-17 |
| JP2004506736A (ja) | 2004-03-04 |
| DE60117568D1 (de) | 2006-04-27 |
| PE20020506A1 (es) | 2002-07-09 |
| UY26899A1 (es) | 2002-03-22 |
| MXPA03001593A (es) | 2003-06-04 |
| ES2259331T3 (es) | 2006-10-01 |
| WO2002016359A1 (en) | 2002-02-28 |
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| FZDE | Discontinued |