TWI380981B - 有機化合物之合成方法 - Google Patents
有機化合物之合成方法 Download PDFInfo
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- TWI380981B TWI380981B TW095120304A TW95120304A TWI380981B TW I380981 B TWI380981 B TW I380981B TW 095120304 A TW095120304 A TW 095120304A TW 95120304 A TW95120304 A TW 95120304A TW I380981 B TWI380981 B TW I380981B
- Authority
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- Taiwan
- Prior art keywords
- methyl
- trifluoromethyl
- imidazol
- compound
- stirred
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 8
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 52
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 18
- WWTGXYAJVXKEKL-UHFFFAOYSA-N 3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)aniline Chemical compound C1=NC(C)=CN1C1=CC(N)=CC(C(F)(F)F)=C1 WWTGXYAJVXKEKL-UHFFFAOYSA-N 0.000 claims description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- WQKQODZOQAFYPR-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(F)=CC(C(F)(F)F)=C1 WQKQODZOQAFYPR-UHFFFAOYSA-N 0.000 claims description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- HJTLKVYOWNTDPF-UHFFFAOYSA-N 3-bromo-5-(trifluoromethyl)aniline Chemical compound NC1=CC(Br)=CC(C(F)(F)F)=C1 HJTLKVYOWNTDPF-UHFFFAOYSA-N 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- CZXXZRIHUHYXIQ-UHFFFAOYSA-N 1-bromo-2,3,4,6-tetrafluoro-5-methylbenzene Chemical compound CC1=C(F)C(F)=C(F)C(Br)=C1F CZXXZRIHUHYXIQ-UHFFFAOYSA-N 0.000 claims description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
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- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 claims description 2
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 1
- 108091008606 PDGF receptors Proteins 0.000 description 1
- 241001482237 Pica Species 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- DXPIZCZNFUTPEI-UHFFFAOYSA-O diphenylphosphanium;azide Chemical compound [N-]=[N+]=[N-].C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 DXPIZCZNFUTPEI-UHFFFAOYSA-O 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000005226 trifluoromethylbenzenes Chemical class 0.000 description 1
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68897605P | 2005-06-09 | 2005-06-09 |
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|---|---|
| TW200716563A TW200716563A (en) | 2007-05-01 |
| TWI380981B true TWI380981B (zh) | 2013-01-01 |
Family
ID=37149980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095120304A TWI380981B (zh) | 2005-06-09 | 2006-06-08 | 有機化合物之合成方法 |
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| EP (3) | EP1896426B1 (enExample) |
| JP (2) | JP5225078B2 (enExample) |
| KR (2) | KR101249199B1 (enExample) |
| CN (6) | CN102174020B (enExample) |
| AR (1) | AR057056A1 (enExample) |
| AT (1) | ATE540931T1 (enExample) |
| AU (3) | AU2006258050B2 (enExample) |
| BR (1) | BRPI0611683A2 (enExample) |
| CA (4) | CA2942046A1 (enExample) |
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| IN (2) | IN2014DN08578A (enExample) |
| JO (1) | JO2758B1 (enExample) |
| MX (1) | MX2007015609A (enExample) |
| MY (1) | MY146795A (enExample) |
| PE (3) | PE20070109A1 (enExample) |
| PL (3) | PL2266961T3 (enExample) |
| PT (3) | PT2292607E (enExample) |
| RU (1) | RU2446162C2 (enExample) |
| SI (2) | SI2266961T1 (enExample) |
| TW (1) | TWI380981B (enExample) |
| WO (1) | WO2006135640A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS53639B1 (sr) | 2004-03-05 | 2015-04-30 | Nissan Chemical Industries Ltd. | Izoksazolinom supstituisano benzamidno jedinjenje i sredstvo za kontrolu štetnih organizama |
| MY146795A (en) * | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| TWI412322B (zh) | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| MX2009013469A (es) | 2007-06-13 | 2010-01-20 | Du Pont | Insecticidas de isoxazolina. |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| HUE037127T2 (hu) | 2007-06-27 | 2018-08-28 | Du Pont | Állati károkozó irtására szolgáló eljárás |
| TWI461411B (zh) | 2007-08-17 | 2014-11-21 | Du Pont | 製備５－鹵烷基－４，５－二氫異唑衍生物之方法 |
| US8367584B2 (en) | 2007-10-03 | 2013-02-05 | E.I. Du Pont De Nemours And Company | Naphthalene isoxazoline compounds for control of invertebrate pests |
| TWI583664B (zh) | 2008-04-09 | 2017-05-21 | 杜邦股份有限公司 | 羰基化合物及其製備方法 |
| WO2010009402A2 (en) * | 2008-07-17 | 2010-01-21 | Teva Pharmaceutical Industries Ltd. | Nilotinib intermediates and preparation thereof |
| EP2530081A3 (en) | 2008-11-05 | 2013-04-10 | Teva Pharmaceutical Industries, Ltd. | Nilotinib HCI crystalline forms |
| WO2010060074A1 (en) * | 2008-11-24 | 2010-05-27 | Teva Pharmaceutical Industries Ltd. | Preparation of nilotinib and intermediates thereof |
| US20110053968A1 (en) | 2009-06-09 | 2011-03-03 | Auspex Pharmaceuticals, Inc. | Aminopyrimidine inhibitors of tyrosine kinase |
| SI2576523T1 (sl) | 2010-05-27 | 2016-05-31 | E.I. du Pont de Nemours and Company Chestnut Run Plaza 974 Center Road | Kristalinične oblike 4-(5-(3-kloro-5-(trifluorometil)fenil)-4,5-dihidro 5-(trifluorometil)-3-izoksazolil)-N-(2-okso-2-((2,2,2-trifluoroetil) amino)etil)-1 naftalenkarboksamida |
| BR122019019582B1 (pt) | 2011-12-30 | 2021-07-13 | Hanmi Pharm. Co., Ltd. | Compostos derivados de tieno[3,2-d]pirimidina, composição farmacêutica contendo os ditos compostos e uso dos mesmos para a prevenção ou tratamento de uma doença causada por ativação anormal de uma proteína quinase |
| CN102592837B (zh) * | 2012-03-12 | 2014-01-15 | 河北师范大学 | 制备超级电容器用四氯合金属季铵盐掺杂聚苯胺电极的方法 |
| CN103694176B (zh) * | 2014-01-07 | 2015-02-18 | 苏州立新制药有限公司 | 尼洛替尼中间体的制备方法 |
| CN104592122B (zh) * | 2014-12-09 | 2018-01-23 | 凯莱英医药集团（天津）股份有限公司 | 3‑(4‑甲基‑1h‑咪唑‑1‑基)‑5‑(三氟甲基)苯胺的制备方法 |
| CN105985293B (zh) * | 2015-03-04 | 2018-04-03 | 埃斯特维华义制药有限公司 | 尼洛替尼中间体的制备方法 |
| EP3095782A1 (en) | 2015-05-18 | 2016-11-23 | Esteve Química, S.A. | New method for preparing 3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl)benzenamine |
| CN107201532B (zh) * | 2017-05-09 | 2019-08-27 | 吉林凯莱英医药化学有限公司 | 芳香化合物的硝化方法 |
| WO2019130254A1 (en) * | 2018-01-01 | 2019-07-04 | Laurus Labs Ltd | An improved process for 3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl) aniline |
| CN108530364B (zh) * | 2018-04-10 | 2020-01-21 | 江苏创诺制药有限公司 | 一种3-(4-甲基-1h-咪唑-1-基)-5-三氟甲基苯胺单盐酸盐的晶型及其应用 |
| KR20210042896A (ko) | 2018-06-15 | 2021-04-20 | 한다 파마슈티칼스, 인코포레이티드 | 카이네이스 억제제 염 및 이의 조성물 |
| CA3136189A1 (en) * | 2019-04-06 | 2020-10-15 | Trinapco, Inc. | Sulfonyldiazoles and n-(fluorosulfonyl)azoles, and methods of making the same |
| EP3904342A1 (en) | 2020-04-28 | 2021-11-03 | Grindeks, A Joint Stock Company | Process for the preparation of 3-(trifluoromethyl)-5-(4-methyl-1h-imidazole-1-yl)-benzeneamine hydrochloride |
| CN114751836B (zh) * | 2021-02-23 | 2024-05-31 | 四川青木制药有限公司 | 3-(4-甲基-1h-咪唑-1-基)-5-(三氟甲基)苯胺合成方法及其中间体 |
| CN114853734A (zh) * | 2022-06-14 | 2022-08-05 | 海南鑫开源医药科技有限公司 | 一种尼洛替尼游离碱的制备方法 |
| CN116478319B (zh) * | 2022-11-07 | 2025-07-01 | 华北电力大学 | 一种离子共价有机聚合物的制备方法及其在碱性环境吸附ReO4-的应用 |
| CN115626880B (zh) * | 2022-11-15 | 2023-11-14 | 常州大学 | 3-硝基-5-氰基三氟甲苯的合成方法 |
| CN118108670B (zh) * | 2023-12-28 | 2025-07-01 | 江苏希迪制药有限公司 | 尼罗替尼中间体3-(4-甲基-1h-咪唑-1-基)-5-(三氟甲基)苯胺的精制纯化方法 |
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| EP0166533A1 (en) * | 1984-05-29 | 1986-01-02 | Pfizer Limited | Quinolone inotropic agents |
| WO2001053274A1 (en) * | 2000-01-21 | 2001-07-26 | Agouron Pharmaceuticals, Inc. | Amide compounds for inhibiting protein kinases |
| WO2004005281A1 (en) * | 2002-07-05 | 2004-01-15 | Novartis Ag | Inhibitors of tyrosine kinases |
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| SU1051076A1 (ru) * | 1982-04-09 | 1983-10-30 | Алтайский политехнический институт | Способ получени производных имидазола |
| GB8413685D0 (en) * | 1984-05-29 | 1984-07-04 | Pfizer Ltd | Quinolone inotropic agents |
| GB8502267D0 (en) * | 1985-01-30 | 1985-02-27 | Pfizer Ltd | Quinolone inotropic agents |
| GB0023383D0 (en) * | 2000-09-23 | 2000-11-08 | Synprotec Ltd | 3,5-Bis (Trifluormethyl)Benzene derivatives |
| TW200406374A (en) | 2002-05-29 | 2004-05-01 | Novartis Ag | Diaryl urea derivatives useful for the treatment of protein kinase dependent diseases |
| GB0222514D0 (en) * | 2002-09-27 | 2002-11-06 | Novartis Ag | Organic compounds |
| CN1939910A (zh) * | 2004-12-31 | 2007-04-04 | 孙飘扬 | 氨基嘧啶类化合物及其盐和其制备方法与药物用途 |
| MY146795A (en) * | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
| GT200600207A (es) * | 2005-06-09 | 2007-01-15 | Novartis Ag | Proceso para la síntesis de compuestos orgánicos |
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|---|---|---|---|---|
| EP0166533A1 (en) * | 1984-05-29 | 1986-01-02 | Pfizer Limited | Quinolone inotropic agents |
| WO2001053274A1 (en) * | 2000-01-21 | 2001-07-26 | Agouron Pharmaceuticals, Inc. | Amide compounds for inhibiting protein kinases |
| WO2004005281A1 (en) * | 2002-07-05 | 2004-01-15 | Novartis Ag | Inhibitors of tyrosine kinases |
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