CA2610402C - Process for the synthesis of 5-(methyl-1h-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine - Google Patents
Process for the synthesis of 5-(methyl-1h-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine Download PDFInfo
- Publication number
- CA2610402C CA2610402C CA2610402A CA2610402A CA2610402C CA 2610402 C CA2610402 C CA 2610402C CA 2610402 A CA2610402 A CA 2610402A CA 2610402 A CA2610402 A CA 2610402A CA 2610402 C CA2610402 C CA 2610402C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- trifluoromethyl
- imidazole
- compound
- process according
- 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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Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 13
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- BETRKLAUVABHFV-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)-5-(trifluoromethyl)aniline Chemical compound CC1=NC=CN1C1=CC(N)=CC(C(F)(F)F)=C1 BETRKLAUVABHFV-UHFFFAOYSA-N 0.000 title 1
- 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 abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- JMLCVCGQBRZYOZ-UHFFFAOYSA-N 4-methyl-1-[3-nitro-5-(trifluoromethyl)phenyl]imidazole Chemical compound C1=NC(C)=CN1C1=CC([N+]([O-])=O)=CC(C(F)(F)F)=C1 JMLCVCGQBRZYOZ-UHFFFAOYSA-N 0.000 claims 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- JGJYPPNLUXMOKO-UHFFFAOYSA-N 2-(pyrimidin-2-ylamino)benzamide Chemical class NC(=O)C1=CC=CC=C1NC1=NC=CC=N1 JGJYPPNLUXMOKO-UHFFFAOYSA-N 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- YEAOVYLCHBNHNT-UHFFFAOYSA-N 1,2-dinitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1[N+]([O-])=O YEAOVYLCHBNHNT-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- -1 potassium alkoxide Chemical class 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- 108091008606 PDGF receptors Proteins 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68892005P | 2005-06-09 | 2005-06-09 | |
| US60/688,920 | 2005-06-09 | ||
| PCT/US2006/022026 WO2006135619A1 (en) | 2005-06-09 | 2006-06-07 | Process for the synthesis of 5- (methyl- 1h-imidazol-1-yl) -3- (trifluoromethyl) -benzeneamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2610402A1 CA2610402A1 (en) | 2006-12-21 |
| CA2610402C true CA2610402C (en) | 2014-09-16 |
Family
ID=37085334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2610402A Active CA2610402C (en) | 2005-06-09 | 2006-06-07 | Process for the synthesis of 5-(methyl-1h-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7709657B2 (enExample) |
| EP (1) | EP1896425B1 (enExample) |
| JP (1) | JP5139273B2 (enExample) |
| KR (1) | KR101319071B1 (enExample) |
| CN (1) | CN101193866B (enExample) |
| AR (1) | AR057351A1 (enExample) |
| AT (1) | ATE483690T1 (enExample) |
| AU (1) | AU2006258116B2 (enExample) |
| BR (1) | BRPI0611924A2 (enExample) |
| CA (1) | CA2610402C (enExample) |
| DE (1) | DE602006017369D1 (enExample) |
| ES (1) | ES2354115T3 (enExample) |
| GT (1) | GT200600207A (enExample) |
| MX (1) | MX2007015420A (enExample) |
| PE (1) | PE20070084A1 (enExample) |
| PL (1) | PL1896425T3 (enExample) |
| PT (1) | PT1896425E (enExample) |
| RU (1) | RU2404167C2 (enExample) |
| TW (1) | TW200710084A (enExample) |
| WO (1) | WO2006135619A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY146795A (en) * | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
| GB0618832D0 (en) * | 2006-09-25 | 2006-11-01 | Phoenix Chemicals Ltd | Chemical process |
| US20110053968A1 (en) * | 2009-06-09 | 2011-03-03 | Auspex Pharmaceuticals, Inc. | Aminopyrimidine inhibitors of tyrosine kinase |
| EP3144194B1 (en) | 2014-05-16 | 2018-05-09 | Robert Bosch GmbH | Abs hydraulic unit |
| KR102335216B1 (ko) | 2017-04-26 | 2021-12-03 | 삼성전자 주식회사 | 발광소자 패키지 |
| CN107235910B (zh) * | 2017-07-31 | 2020-04-24 | 安礼特（上海）医药科技有限公司 | 一种尼洛胺的合成方法 |
| 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 |
| CN113292537B (zh) | 2018-06-15 | 2024-04-05 | 汉达癌症医药责任有限公司 | 激酶抑制剂的盐类及其组合物 |
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8413685D0 (en) * | 1984-05-29 | 1984-07-04 | Pfizer Ltd | Quinolone inotropic agents |
| US5516775A (en) * | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
| CN1047776C (zh) * | 1993-10-01 | 1999-12-29 | 诺瓦蒂斯有限公司 | 具有药理学活性的吡啶类衍生物及其制备方法 |
| US6323366B1 (en) | 1997-07-29 | 2001-11-27 | Massachusetts Institute Of Technology | Arylamine synthesis |
| US6395916B1 (en) | 1998-07-10 | 2002-05-28 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| HN2001000008A (es) * | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| PE20040522A1 (es) * | 2002-05-29 | 2004-09-28 | Novartis Ag | Derivados de diarilurea dependientes de la cinasa de proteina |
| US7202367B2 (en) | 2002-05-31 | 2007-04-10 | Rhodia Chimie | Process for arylating or vinylating or alkynating a nucleophilic compound |
| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
-
2006
- 2006-05-18 GT GT200600207A patent/GT200600207A/es unknown
- 2006-06-07 ES ES06772366T patent/ES2354115T3/es active Active
- 2006-06-07 CA CA2610402A patent/CA2610402C/en active Active
- 2006-06-07 BR BRPI0611924-7A patent/BRPI0611924A2/pt active Search and Examination
- 2006-06-07 US US11/915,658 patent/US7709657B2/en active Active
- 2006-06-07 KR KR1020077028640A patent/KR101319071B1/ko not_active Expired - Fee Related
- 2006-06-07 JP JP2008515848A patent/JP5139273B2/ja not_active Expired - Fee Related
- 2006-06-07 RU RU2007147927/04A patent/RU2404167C2/ru active
- 2006-06-07 EP EP06772366A patent/EP1896425B1/en active Active
- 2006-06-07 DE DE602006017369T patent/DE602006017369D1/de active Active
- 2006-06-07 PT PT06772366T patent/PT1896425E/pt unknown
- 2006-06-07 WO PCT/US2006/022026 patent/WO2006135619A1/en not_active Ceased
- 2006-06-07 CN CN2006800202295A patent/CN101193866B/zh not_active Expired - Fee Related
- 2006-06-07 PL PL06772366T patent/PL1896425T3/pl unknown
- 2006-06-07 AT AT06772366T patent/ATE483690T1/de active
- 2006-06-07 PE PE2006000629A patent/PE20070084A1/es not_active Application Discontinuation
- 2006-06-07 AU AU2006258116A patent/AU2006258116B2/en not_active Ceased
- 2006-06-07 AR ARP060102368A patent/AR057351A1/es not_active Application Discontinuation
- 2006-06-07 MX MX2007015420A patent/MX2007015420A/es active IP Right Grant
- 2006-06-08 TW TW095120303A patent/TW200710084A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR057351A1 (es) | 2007-11-28 |
| AU2006258116B2 (en) | 2010-11-25 |
| PL1896425T3 (pl) | 2011-04-29 |
| WO2006135619A1 (en) | 2006-12-21 |
| US20080200691A1 (en) | 2008-08-21 |
| BRPI0611924A2 (pt) | 2010-10-05 |
| CN101193866B (zh) | 2011-01-19 |
| DE602006017369D1 (de) | 2010-11-18 |
| TW200710084A (en) | 2007-03-16 |
| JP2008545782A (ja) | 2008-12-18 |
| RU2404167C2 (ru) | 2010-11-20 |
| MX2007015420A (es) | 2008-02-21 |
| KR101319071B1 (ko) | 2013-10-17 |
| JP5139273B2 (ja) | 2013-02-06 |
| RU2007147927A (ru) | 2009-07-20 |
| CA2610402A1 (en) | 2006-12-21 |
| ATE483690T1 (de) | 2010-10-15 |
| EP1896425B1 (en) | 2010-10-06 |
| EP1896425A1 (en) | 2008-03-12 |
| US7709657B2 (en) | 2010-05-04 |
| PT1896425E (pt) | 2010-11-30 |
| ES2354115T3 (es) | 2011-03-10 |
| PE20070084A1 (es) | 2007-03-09 |
| AU2006258116A1 (en) | 2006-12-21 |
| GT200600207A (es) | 2007-01-15 |
| CN101193866A (zh) | 2008-06-04 |
| KR20080016618A (ko) | 2008-02-21 |
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