JP2007512362A5 - - Google Patents
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- Publication number
- JP2007512362A5 JP2007512362A5 JP2006541579A JP2006541579A JP2007512362A5 JP 2007512362 A5 JP2007512362 A5 JP 2007512362A5 JP 2006541579 A JP2006541579 A JP 2006541579A JP 2006541579 A JP2006541579 A JP 2006541579A JP 2007512362 A5 JP2007512362 A5 JP 2007512362A5
- Authority
- JP
- Japan
- Prior art keywords
- heteroaryl
- aryl
- alkyl
- cycloalkyl
- halogen
- 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
Links
- 125000001072 heteroaryl group Chemical group 0.000 claims 177
- 125000003118 aryl group Chemical group 0.000 claims 159
- 125000000217 alkyl group Chemical group 0.000 claims 149
- 125000000623 heterocyclic group Chemical group 0.000 claims 122
- 125000000753 cycloalkyl group Chemical group 0.000 claims 121
- 229910052736 halogen Inorganic materials 0.000 claims 111
- 150000002367 halogens Chemical class 0.000 claims 111
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 110
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 98
- -1 resolved enantiomers Chemical class 0.000 claims 90
- 125000003342 alkenyl group Chemical group 0.000 claims 86
- 150000001875 compounds Chemical class 0.000 claims 76
- 125000003710 aryl alkyl group Chemical group 0.000 claims 75
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 73
- 125000000304 alkynyl group Chemical group 0.000 claims 72
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims 69
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 65
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 63
- 229910052739 hydrogen Inorganic materials 0.000 claims 63
- 239000001257 hydrogen Substances 0.000 claims 63
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 62
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 56
- 150000002431 hydrogen Chemical class 0.000 claims 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 38
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 37
- BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 32
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000004429 atom Chemical group 0.000 claims 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 12
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 12
- OBBCQHYXZOIRNT-UHFFFAOYSA-N azido(nitro)cyanamide Chemical compound [O-][N+](=O)N(C#N)N=[N+]=[N-] OBBCQHYXZOIRNT-UHFFFAOYSA-N 0.000 claims 11
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 5
- 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 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 5
- 229910019142 PO4 Inorganic materials 0.000 claims 5
- 125000000539 amino acid group Chemical group 0.000 claims 5
- 150000001448 anilines Chemical class 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 5
- 239000010452 phosphate Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 0 CC=C(C=CC(*)=**C*)Nc1c(C(OC)=O)nc(c(C)n[o]2)c2c1* Chemical compound CC=C(C=CC(*)=**C*)Nc1c(C(OC)=O)nc(c(C)n[o]2)c2c1* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52327003P | 2003-11-19 | 2003-11-19 | |
| US60/523,270 | 2003-11-19 | ||
| PCT/US2004/039053 WO2005051906A2 (en) | 2003-11-19 | 2004-11-18 | Heterocyclic inhibitors of mek and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007512362A JP2007512362A (ja) | 2007-05-17 |
| JP2007512362A5 true JP2007512362A5 (https=) | 2008-01-10 |
| JP4842137B2 JP4842137B2 (ja) | 2011-12-21 |
Family
ID=34632766
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006541579A Expired - Fee Related JP4842137B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋのヘテロ環系阻害剤及びその使用方法 |
| JP2006541582A Expired - Fee Related JP4768628B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋの二環系阻害剤及びその使用方法 |
| JP2006541580A Expired - Fee Related JP5046649B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋの二環系阻害剤及びその使用方法 |
| JP2006541581A Expired - Fee Related JP4869075B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋの複素環阻害剤及びその使用方法 |
| JP2011026680A Pending JP2011121984A (ja) | 2003-11-19 | 2011-02-10 | Ｍｅｋの二環系阻害剤及びその使用方法 |
| JP2011070628A Pending JP2011153151A (ja) | 2003-11-19 | 2011-03-28 | Ｍｅｋの複素環阻害剤及びその使用方法 |
| JP2011070629A Pending JP2011173890A (ja) | 2003-11-19 | 2011-03-28 | Ｍｅｋの複素環阻害剤及びその使用方法 |
| JP2012029242A Pending JP2012092151A (ja) | 2003-11-19 | 2012-02-14 | Ｍｅｋの二環系阻害剤及びその使用方法 |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006541582A Expired - Fee Related JP4768628B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋの二環系阻害剤及びその使用方法 |
| JP2006541580A Expired - Fee Related JP5046649B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋの二環系阻害剤及びその使用方法 |
| JP2006541581A Expired - Fee Related JP4869075B2 (ja) | 2003-11-19 | 2004-11-18 | Ｍｅｋの複素環阻害剤及びその使用方法 |
| JP2011026680A Pending JP2011121984A (ja) | 2003-11-19 | 2011-02-10 | Ｍｅｋの二環系阻害剤及びその使用方法 |
| JP2011070628A Pending JP2011153151A (ja) | 2003-11-19 | 2011-03-28 | Ｍｅｋの複素環阻害剤及びその使用方法 |
| JP2011070629A Pending JP2011173890A (ja) | 2003-11-19 | 2011-03-28 | Ｍｅｋの複素環阻害剤及びその使用方法 |
| JP2012029242A Pending JP2012092151A (ja) | 2003-11-19 | 2012-02-14 | Ｍｅｋの二環系阻害剤及びその使用方法 |
Country Status (30)
| Country | Link |
|---|---|
| US (7) | US7576072B2 (https=) |
| EP (5) | EP1689233B1 (https=) |
| JP (8) | JP4842137B2 (https=) |
| KR (3) | KR101264570B1 (https=) |
| CN (2) | CN102633716A (https=) |
| AT (2) | ATE524443T1 (https=) |
| AU (6) | AU2004293436B2 (https=) |
| BR (1) | BRPI0416692A (https=) |
| CA (4) | CA2546353A1 (https=) |
| CY (2) | CY1111155T1 (https=) |
| DE (1) | DE602004031037D1 (https=) |
| DK (2) | DK1682138T3 (https=) |
| EG (1) | EG24928A (https=) |
| ES (4) | ES2369835T3 (https=) |
| HR (1) | HRP20110105T4 (https=) |
| IL (3) | IL175716A (https=) |
| MX (1) | MXPA06005657A (https=) |
| NO (1) | NO20062692L (https=) |
| NZ (1) | NZ547481A (https=) |
| PH (1) | PH12012501386A1 (https=) |
| PL (4) | PL1689233T3 (https=) |
| PT (4) | PT2251327E (https=) |
| RS (2) | RS51861B2 (https=) |
| RU (1) | RU2351593C2 (https=) |
| SG (1) | SG149033A1 (https=) |
| SI (1) | SI1682138T1 (https=) |
| TW (7) | TW200526658A (https=) |
| UA (1) | UA84175C2 (https=) |
| WO (4) | WO2005051302A2 (https=) |
| ZA (2) | ZA200604580B (https=) |
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2004
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