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 US7235537B2 (en) | 2002-03-13 | 2003-08-29 | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| US10/652,733 | 2003-08-29 | ||
| 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 (enExample) | 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 (enExample) |
| EP (1) | EP1663210B1 (enExample) |
| JP (1) | JP5026076B2 (enExample) |
| KR (1) | KR20060121853A (enExample) |
| CN (1) | CN1874768A (enExample) |
| AR (1) | AR045738A1 (enExample) |
| AU (1) | AU2004270166A1 (enExample) |
| BR (1) | BRPI0413152A (enExample) |
| CA (1) | CA2537098A1 (enExample) |
| ES (1) | ES2628959T3 (enExample) |
| IL (1) | IL173935A (enExample) |
| IS (1) | IS8384A (enExample) |
| MX (1) | MXPA06002268A (enExample) |
| NO (1) | NO20061432L (enExample) |
| RU (1) | RU2006109600A (enExample) |
| TW (1) | TW200524879A (enExample) |
| WO (1) | WO2005023251A1 (enExample) |
| ZA (1) | ZA200602588B (enExample) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1482932E (pt) * | 2002-03-13 | 2010-01-12 | Array Biopharma Inc | Derivados de benzimidazole alquilado n3 como inibidores de mek |
| ES2331246T3 (es) * | 2003-07-24 | 2009-12-28 | Warner-Lambert Company Llc | Derivados de benzamidazol como inhibidores del mek. |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7538120B2 (en) * | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7732616B2 (en) * | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| KR101190912B1 (ko) * | 2003-11-19 | 2012-10-12 | 어레이 바이오파마 인크. | Ｍｅｋ의 헤테로시클릭 억제제 및 그의 사용 방법 |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| BRPI0416852A (pt) * | 2003-11-21 | 2007-02-27 | Array Biopharma Inc | inibidores da quinase akt |
| CN102321030A (zh) * | 2005-05-18 | 2012-01-18 | 阵列生物制药公司 | Mek的杂环抑制剂及其使用方法 |
| AU2006302415B2 (en) | 2005-10-07 | 2012-09-13 | Exelixis, Inc. | Azetidines as MEK inhibitors for the treatment of proliferative diseases |
| ATE507224T1 (de) | 2005-11-15 | 2011-05-15 | Array Biopharma Inc | Verfahren und zwischenverbindungen zur herstellung von n4-phenyl-quinazolin-4-amin derivaten |
| EP1966155A1 (en) * | 2005-12-21 | 2008-09-10 | AstraZeneca AB | Tosylate salt of 6- (4-br0m0-2-chl0r0phenylamin0) -7-fluoro-n- (2-hydroxyethoxy) -3-methyl-3h-benzimi dazole- 5 - carboxamide , mek inhibitor useful in the treatment of cancer |
| RU2418790C3 (ru) * | 2005-12-21 | 2022-03-14 | Астразенека Аб | Новая гидросульфатная соль |
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| DK2054418T3 (da) | 2006-07-06 | 2012-02-27 | Array Biopharma Inc | Dihydrothieno-pyrimidiner som AKT-proteinkinase-inhibitorer |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| SI2049500T1 (sl) * | 2006-07-06 | 2012-01-31 | Array Biopharma Inc | Ciklopenta (d) pirimidini kot AKT protein kinazni inhibitorji |
| CA2656566C (en) | 2006-07-06 | 2014-06-17 | Array Biopharma Inc. | Dihydrofuro pyrimidines as akt protein kinase inhibitors |
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| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
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| BRPI0815180A2 (pt) * | 2007-08-16 | 2019-09-24 | Hoffmann La Roche | hindantoinas substituídas |
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| BRPI0915901A2 (pt) * | 2008-07-11 | 2015-10-27 | Novartis Ag | combinação de (a) um inibidor de fosfoinositídeo 3-quinase e (b) um modulador da via ras/raf/mek |
| JP5746630B2 (ja) | 2008-11-10 | 2015-07-08 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換スルホンアミドフェノキシベンズアミド |
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| WO2012019113A2 (en) | 2010-08-05 | 2012-02-09 | Case Western Reserve University | Inhibitors of erk for developmental disorders of neuronal connectivity |
| SI2624696T1 (sl) | 2010-10-06 | 2017-04-26 | Glaxosmithkline Llc Corporation Service Company | Benzimidazolni derivati kot inhibitorji pi3-kinaze |
| JP2013542214A (ja) | 2010-10-29 | 2013-11-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 置換フェノキシピリジン類 |
| CN102020651B (zh) | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
| ES2531465T3 (es) | 2010-12-23 | 2015-03-16 | Sanofi | Derivados de pirimidinona, su preparación y su utilización farmacéutica |
| CN103857395A (zh) | 2011-04-01 | 2014-06-11 | 基因泰克公司 | Akt抑制剂化合物和阿比特龙的组合及使用方法 |
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| EP2714037B1 (en) | 2011-05-25 | 2016-07-13 | Université Paris Descartes | Erk inhibitors for use in treating spinal muscular atrophy |
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| CN103204827B (zh) | 2012-01-17 | 2014-12-03 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的苯并噻二唑化合物及其制备方法和用途 |
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| CN120309621A (zh) | 2021-10-20 | 2025-07-15 | 豪夫迈·罗氏有限公司 | 喹唑啉衍生物的结晶形式、其制备、组合物和用途 |
| 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 |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
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2003
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2004
- 2004-08-20 CN CNA2004800323322A patent/CN1874768A/zh active Pending
- 2004-08-20 AU AU2004270166A patent/AU2004270166A1/en not_active Abandoned
- 2004-08-20 KR KR1020067004187A patent/KR20060121853A/ko not_active Withdrawn
- 2004-08-20 EP EP04781809.1A patent/EP1663210B1/en not_active Expired - Lifetime
- 2004-08-20 CA CA002537098A patent/CA2537098A1/en not_active Abandoned
- 2004-08-20 MX MXPA06002268A patent/MXPA06002268A/es unknown
- 2004-08-20 JP JP2006524761A patent/JP5026076B2/ja not_active Expired - Lifetime
- 2004-08-20 ZA ZA200602588A patent/ZA200602588B/en unknown
- 2004-08-20 WO PCT/US2004/027199 patent/WO2005023251A1/en not_active Ceased
- 2004-08-20 RU RU2006109600/04A patent/RU2006109600A/ru not_active Application Discontinuation
- 2004-08-20 ES ES04781809.1T patent/ES2628959T3/es not_active Expired - Lifetime
- 2004-08-20 BR BRPI0413152-5A patent/BRPI0413152A/pt not_active Application Discontinuation
- 2004-08-20 TW TW093125125A patent/TW200524879A/zh unknown
- 2004-08-27 AR ARP040103103A patent/AR045738A1/es not_active Application Discontinuation
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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
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2007
- 2007-06-14 US US11/762,897 patent/US7842816B2/en not_active Expired - Lifetime