JP2007504139A5 - - Google Patents
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- Publication number
- JP2007504139A5 JP2007504139A5 JP2006524761A JP2006524761A JP2007504139A5 JP 2007504139 A5 JP2007504139 A5 JP 2007504139A5 JP 2006524761 A JP2006524761 A JP 2006524761A JP 2006524761 A JP2006524761 A JP 2006524761A JP 2007504139 A5 JP2007504139 A5 JP 2007504139A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- heteroaryl
- heterocyclyl
- alkyl
- fluoro
- 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 24
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims 15
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims 8
- -1 het Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 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 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- WWWTWPXKLJTKPM-UHFFFAOYSA-N 2-aminooxyethanol Chemical compound NOCCO WWWTWPXKLJTKPM-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- LEIHLFODGVRBMK-UHFFFAOYSA-N 1-[6-(4-bromo-2-chloroanilino)-7-fluoro-3-methylbenzimidazol-5-yl]-2-hydroxyethanone Chemical compound OCC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl LEIHLFODGVRBMK-UHFFFAOYSA-N 0.000 claims 1
- TYWZTXWVZYCZNW-UHFFFAOYSA-N 1-[6-(4-bromo-2-chloroanilino)-7-fluoro-3h-benzimidazol-5-yl]-2-methoxyethanone Chemical compound COCC(=O)C1=CC=2NC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl TYWZTXWVZYCZNW-UHFFFAOYSA-N 0.000 claims 1
- XHHGPLBYQFIILA-UHFFFAOYSA-N 5-[6-(4-bromo-2-methylanilino)-7-fluoro-3h-benzimidazol-5-yl]-1,3,4-oxadiazol-2-amine Chemical compound CC1=CC(Br)=CC=C1NC(C(=C1)C=2OC(N)=NN=2)=C(F)C2=C1NC=N2 XHHGPLBYQFIILA-UHFFFAOYSA-N 0.000 claims 1
- PCDIFCAYTFFSCS-UHFFFAOYSA-N 6-(4-bromo-2-chloroanilino)-7-fluoro-n-(1-hydroxy-2-methylpropan-2-yl)oxy-3-methylbenzimidazole-5-carboxamide Chemical compound OCC(C)(C)ONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl PCDIFCAYTFFSCS-UHFFFAOYSA-N 0.000 claims 1
- HVUPVWYURYMZHF-UHFFFAOYSA-N 6-(4-bromo-2-chloroanilino)-n-(2,3-dihydroxypropoxy)-7-fluoro-3-methylbenzimidazole-5-carboxamide Chemical compound OCC(O)CONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl HVUPVWYURYMZHF-UHFFFAOYSA-N 0.000 claims 1
- KHNUMHAPGZJGJD-UHFFFAOYSA-N 6-(4-bromo-2-chloroanilino)-n-(cyclopropylmethoxy)-7-fluoro-3h-benzimidazole-5-carboxamide Chemical compound C1CC1CONC(=O)C1=CC=2NC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl KHNUMHAPGZJGJD-UHFFFAOYSA-N 0.000 claims 1
- DHZGVPNAMLHFJL-UHFFFAOYSA-N 6-(4-bromo-2-methylanilino)-n-(cyclopropylmethoxy)-7-fluoro-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC(Br)=CC=C1NC(C(=C1)C(=O)NOCC2CC2)=C(F)C2=C1N=CN2 DHZGVPNAMLHFJL-UHFFFAOYSA-N 0.000 claims 1
- DVIZCUIJAJSXJB-UHFFFAOYSA-N 6-(4-chloro-2-methylanilino)-7-fluoro-n-[(2-methylpropan-2-yl)oxy]-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC(Cl)=CC=C1NC(C(=C1)C(=O)NOC(C)(C)C)=C(F)C2=C1NC=N2 DVIZCUIJAJSXJB-UHFFFAOYSA-N 0.000 claims 1
- ZASPDCHDEWDRLZ-UHFFFAOYSA-N 7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide Chemical compound Cn1cnc2c(F)cc(cc12)C(=O)NOCCO ZASPDCHDEWDRLZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 125000000539 amino acid group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- ACWZRVQXLIRSDF-UHFFFAOYSA-N binimetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1F ACWZRVQXLIRSDF-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000005541 phosphonamide group Chemical group 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- CYOHGALHFOKKQC-UHFFFAOYSA-N selumetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl CYOHGALHFOKKQC-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/652,733 | 2003-08-29 | ||
| US10/652,733 US7235537B2 (en) | 2002-03-13 | 2003-08-29 | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| PCT/US2004/027199 WO2005023251A1 (en) | 2003-08-29 | 2004-08-20 | N3 alkylated benzimidazole derivatives as mek inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007504139A JP2007504139A (ja) | 2007-03-01 |
| JP2007504139A5 true JP2007504139A5 (OSRAM) | 2007-09-27 |
| JP5026076B2 JP5026076B2 (ja) | 2012-09-12 |
Family
ID=34273411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006524761A Expired - Lifetime JP5026076B2 (ja) | 2003-08-29 | 2004-08-20 | Ｍｅｋ阻害剤としてのｎ３アルキル化ベンズイミダゾール誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7235537B2 (OSRAM) |
| EP (1) | EP1663210B1 (OSRAM) |
| JP (1) | JP5026076B2 (OSRAM) |
| KR (1) | KR20060121853A (OSRAM) |
| CN (1) | CN1874768A (OSRAM) |
| AR (1) | AR045738A1 (OSRAM) |
| AU (1) | AU2004270166A1 (OSRAM) |
| BR (1) | BRPI0413152A (OSRAM) |
| CA (1) | CA2537098A1 (OSRAM) |
| ES (1) | ES2628959T3 (OSRAM) |
| IL (1) | IL173935A (OSRAM) |
| IS (1) | IS8384A (OSRAM) |
| MX (1) | MXPA06002268A (OSRAM) |
| NO (1) | NO20061432L (OSRAM) |
| RU (1) | RU2006109600A (OSRAM) |
| TW (1) | TW200524879A (OSRAM) |
| WO (1) | WO2005023251A1 (OSRAM) |
| ZA (1) | ZA200602588B (OSRAM) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2478374C (en) * | 2002-03-13 | 2009-01-06 | Eli M. Wallace | N3 alkylated benzimidazole derivatives as mek inhibitors |
| WO2005009975A2 (en) | 2003-07-24 | 2005-02-03 | Warner-Lambert Company Llc | Benzimidazole derivatives as mek inhibitors |
| US7538120B2 (en) * | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7517994B2 (en) * | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| JP4869075B2 (ja) * | 2003-11-19 | 2012-02-01 | アレイ バイオファーマ、インコーポレイテッド | Ｍｅｋの複素環阻害剤及びその使用方法 |
| US7732616B2 (en) * | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
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| RU2500673C2 (ru) * | 2005-05-18 | 2013-12-10 | Астразенека Аб | Гетероциклические ингибиторы мек и способы их применения |
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| JP2024539212A (ja) | 2021-10-20 | 2024-10-28 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | キナゾリン誘導体の結晶形態、調製、組成物およびその使用 |
| CN116135839A (zh) * | 2021-11-18 | 2023-05-19 | 江苏润安制药有限公司 | 一种阿齐沙坦关键中间体的制备方法 |
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| US5750545A (en) * | 1993-07-23 | 1998-05-12 | The Green Cross Corporation | Triazole derivative and pharmaceutical use thereof |
| US5525625A (en) | 1995-01-24 | 1996-06-11 | Warner-Lambert Company | 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6310060B1 (en) * | 1998-06-24 | 2001-10-30 | Warner-Lambert Company | 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as MEK inhibitors |
| JP2002509536A (ja) | 1997-07-01 | 2002-03-26 | ワーナー−ランバート・カンパニー | ２−（４−ブロモ又は４−ヨードフェニルアミノ）安息香酸誘導体及びｍｅｋ阻害物質としてのそれらの使用 |
| JP2002511092A (ja) | 1997-07-01 | 2002-04-09 | ワーナー−ランバート・コンパニー | ４−ブロモまたは４−ヨードフェニルアミノベンズヒドロキサム酸誘導体およびそのｍｅｋ阻害剤としての使用 |
| US6821963B2 (en) * | 1997-07-01 | 2004-11-23 | Warner-Lambert Company | 4-Bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors |
| US6506798B1 (en) | 1997-07-01 | 2003-01-14 | Warner-Lambert Company | 4-Arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective MEK inhibitors |
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| CA2348236A1 (en) | 1999-01-13 | 2000-07-20 | Stephen Douglas Barrett | 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors |
| IL144214A0 (en) | 1999-01-13 | 2002-05-23 | Warner Lambert Co | Benzoheterocycles and their use as mek inhibitors |
| AP2001002225A0 (en) * | 1999-01-13 | 2001-09-30 | Warner Lambert Co | 1-heterocycle substituted diarylamines. |
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| EP1144371B1 (en) | 1999-01-13 | 2005-11-09 | Warner-Lambert Company Llc | Benzenesulphonamide derivatives and their use as mek inhibitors |
| GB9910577D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
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-
2003
- 2003-08-29 US US10/652,733 patent/US7235537B2/en not_active Expired - Lifetime
-
2004
- 2004-08-20 AU AU2004270166A patent/AU2004270166A1/en not_active Abandoned
- 2004-08-20 ZA ZA200602588A patent/ZA200602588B/en unknown
- 2004-08-20 CA CA002537098A patent/CA2537098A1/en not_active Abandoned
- 2004-08-20 KR KR1020067004187A patent/KR20060121853A/ko not_active Withdrawn
- 2004-08-20 MX MXPA06002268A patent/MXPA06002268A/es unknown
- 2004-08-20 EP EP04781809.1A patent/EP1663210B1/en not_active Expired - Lifetime
- 2004-08-20 CN CNA2004800323322A patent/CN1874768A/zh active Pending
- 2004-08-20 JP JP2006524761A patent/JP5026076B2/ja not_active Expired - Lifetime
- 2004-08-20 RU RU2006109600/04A patent/RU2006109600A/ru not_active Application Discontinuation
- 2004-08-20 WO PCT/US2004/027199 patent/WO2005023251A1/en not_active Ceased
- 2004-08-20 ES ES04781809.1T patent/ES2628959T3/es not_active Expired - Lifetime
- 2004-08-20 TW TW093125125A patent/TW200524879A/zh unknown
- 2004-08-20 BR BRPI0413152-5A patent/BRPI0413152A/pt not_active Application Discontinuation
- 2004-08-27 AR ARP040103103A patent/AR045738A1/es not_active Application Discontinuation
-
2006
- 2006-02-26 IL IL173935A patent/IL173935A/en active IP Right Grant
- 2006-03-29 NO NO20061432A patent/NO20061432L/no not_active Application Discontinuation
- 2006-03-29 IS IS8384A patent/IS8384A/is unknown
-
2007
- 2007-06-14 US US11/762,897 patent/US7842816B2/en not_active Expired - Lifetime
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