JP2006524668A5 - - Google Patents
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- JP2006524668A5 JP2006524668A5 JP2006505807A JP2006505807A JP2006524668A5 JP 2006524668 A5 JP2006524668 A5 JP 2006524668A5 JP 2006505807 A JP2006505807 A JP 2006505807A JP 2006505807 A JP2006505807 A JP 2006505807A JP 2006524668 A5 JP2006524668 A5 JP 2006524668A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- groups
- group
- optionally substituted
- ny1y2
- 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.)
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- 239000000126 substance Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 35
- 150000003839 salts Chemical class 0.000 claims 35
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- -1 arylcarboxy Chemical group 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 21
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 125000003342 alkenyl group Chemical group 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 150000002431 hydrogen Chemical group 0.000 claims 16
- 150000007529 inorganic bases Chemical class 0.000 claims 16
- 150000007522 mineralic acids Chemical class 0.000 claims 16
- 150000007524 organic acids Chemical class 0.000 claims 16
- 235000005985 organic acids Nutrition 0.000 claims 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 150000007530 organic bases Chemical class 0.000 claims 14
- 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 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 11
- 239000004480 active ingredient Substances 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 102000001253 Protein Kinase Human genes 0.000 claims 8
- 108060006633 protein kinase Proteins 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 7
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims 6
- 125000005936 piperidyl group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 5
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical group C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 4
- 230000002062 proliferating effect Effects 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000002512 chemotherapy Methods 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 230000003176 fibrotic effect Effects 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 210000003584 mesangial cell Anatomy 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- ROBLKZZJHHQLLF-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)methoxy]-1H-pyrazol-5-yl]-1H-indole Chemical compound FC1=CC=CC(COC=2NN=C(C=2)C=2NC3=CC=CC=C3C=2)=C1 ROBLKZZJHHQLLF-UHFFFAOYSA-N 0.000 claims 1
- IVNMWVVOFVPHPL-UHFFFAOYSA-N 3-[[5-(1H-indol-2-yl)-1H-pyrazol-3-yl]oxymethyl]phenol Chemical compound OC1=CC=CC(COC=2NN=C(C=2)C=2NC3=CC=CC=C3C=2)=C1 IVNMWVVOFVPHPL-UHFFFAOYSA-N 0.000 claims 1
- JUCQIXUOLHWYIO-UHFFFAOYSA-N 6h-[1,3]dioxolo[4,5-e]benzimidazole Chemical group C1=C2N=CNC2=C2OCOC2=C1 JUCQIXUOLHWYIO-UHFFFAOYSA-N 0.000 claims 1
- QWLONAKTOUSDIR-UHFFFAOYSA-N 7,8-dihydro-3h-[1,4]dioxino[2,3-e]benzimidazole Chemical group O1CCOC2=C1C=CC1=C2NC=N1 QWLONAKTOUSDIR-UHFFFAOYSA-N 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 claims 1
- 101150017750 FGFRL1 gene Proteins 0.000 claims 1
- 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 claims 1
- 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 claims 1
- 102100023600 Fibroblast growth factor receptor 2 Human genes 0.000 claims 1
- 101710182389 Fibroblast growth factor receptor 2 Proteins 0.000 claims 1
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims 1
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims 1
- 102100027844 Fibroblast growth factor receptor 4 Human genes 0.000 claims 1
- 102100026149 Fibroblast growth factor receptor-like 1 Human genes 0.000 claims 1
- 101000917134 Homo sapiens Fibroblast growth factor receptor 4 Proteins 0.000 claims 1
- 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010023825 Laryngeal cancer Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000002231 Muscle Neoplasms Diseases 0.000 claims 1
- 208000010428 Muscle Weakness Diseases 0.000 claims 1
- 206010028372 Muscular weakness Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 claims 1
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 108091008605 VEGF receptors Proteins 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 238000004113 cell culture Methods 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 201000002077 muscle cancer Diseases 0.000 claims 1
- 125000001326 naphthylalkyl group Chemical group 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0305088A FR2854159B1 (fr) | 2003-04-25 | 2003-04-25 | Nouveaux derives de l'indole, leur preparation a titre de medicaments, compositions pharmaceutiques et notamment comme inhibiteurs de kdr |
| PCT/FR2004/000979 WO2004096792A2 (fr) | 2003-04-25 | 2004-04-22 | Nouveaux derives de l'indole, leur preparation a titre de medicaments, compositions pharmaceutiques et notamment comme inhibiteurs de kdr |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006524668A JP2006524668A (ja) | 2006-11-02 |
| JP2006524668A5 true JP2006524668A5 (https=) | 2007-06-14 |
Family
ID=33104394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006505807A Pending JP2006524668A (ja) | 2003-04-25 | 2004-04-22 | 新規なインドール誘導体、ならびに医薬物質および医薬組成物、特にｋｄｒ阻害剤としてのそれらの製造法 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1633738A2 (https=) |
| JP (1) | JP2006524668A (https=) |
| FR (1) | FR2854159B1 (https=) |
| WO (1) | WO2004096792A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI372050B (en) * | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| JP2008501628A (ja) * | 2004-06-02 | 2008-01-24 | 武田薬品工業株式会社 | インドール誘導体およびがんの治療用途 |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| WO2006019832A1 (en) | 2004-07-22 | 2006-02-23 | Ptc Therapeutics, Inc. | Thienopyridines for treating hepatitis c |
| US8399442B2 (en) * | 2005-12-30 | 2013-03-19 | Astex Therapeutics Limited | Pharmaceutical compounds |
| JP5523829B2 (ja) * | 2006-06-29 | 2014-06-18 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| HRP20151258T1 (hr) | 2009-08-07 | 2016-02-26 | Chugai Seiyaku Kabushiki Kaisha | Derivat aminopirazola |
| US8299070B2 (en) * | 2009-11-25 | 2012-10-30 | Japan Tobacco Inc. | Indole compounds and pharmaceutical use thereof |
| JP6514645B2 (ja) | 2013-12-27 | 2019-05-15 | 中外製薬株式会社 | Ｆｇｆｒゲートキーパー変異遺伝子およびそれを標的とする医薬 |
| JP6762300B2 (ja) | 2015-06-17 | 2020-09-30 | 中外製薬株式会社 | アミノピラゾール誘導体 |
| JP7313354B2 (ja) * | 2017-12-19 | 2023-07-24 | ブリストル－マイヤーズ スクイブ カンパニー | Ｔｌｒ阻害剤として有用なアミド置換されたインドール化合物 |
| CN115052860B (zh) * | 2020-01-30 | 2024-06-21 | 艾尼莫生物科技公司 | 胶原蛋白1翻译抑制剂和其使用方法 |
| CA3211730A1 (en) * | 2021-03-17 | 2022-09-22 | Hugh Y. Zhu | Nitrogen-containing heterocyclic ketones, preparation methods and medicinal uses thereof |
| CN116332912B (zh) * | 2023-03-02 | 2025-08-19 | 广西大学 | 一种2-氨基-5-硫基吲哚类衍生物的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6514977B1 (en) * | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| PE20010306A1 (es) * | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
| JP2001122855A (ja) * | 1999-10-27 | 2001-05-08 | Japan Tobacco Inc | インドール化合物及びその医薬用途 |
| YU54202A (sh) * | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| MXPA02010222A (es) * | 2000-04-18 | 2003-05-23 | Agouron Pharma | Pirazoles para inhibir proteina cinasa. |
| WO2003024969A1 (en) * | 2001-09-14 | 2003-03-27 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| FR2831537B1 (fr) * | 2001-10-26 | 2008-02-29 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation |
-
2003
- 2003-04-25 FR FR0305088A patent/FR2854159B1/fr not_active Expired - Fee Related
-
2004
- 2004-04-22 EP EP04742556A patent/EP1633738A2/fr not_active Ceased
- 2004-04-22 JP JP2006505807A patent/JP2006524668A/ja active Pending
- 2004-04-22 WO PCT/FR2004/000979 patent/WO2004096792A2/fr not_active Ceased
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