DE60017109T2 - Verfahren zur herstellung von 2-(n-phenylalmino)benzoesäure - Google Patents
Verfahren zur herstellung von 2-(n-phenylalmino)benzoesäure Download PDFInfo
- Publication number
- DE60017109T2 DE60017109T2 DE60017109T DE60017109T DE60017109T2 DE 60017109 T2 DE60017109 T2 DE 60017109T2 DE 60017109 T DE60017109 T DE 60017109T DE 60017109 T DE60017109 T DE 60017109T DE 60017109 T2 DE60017109 T2 DE 60017109T2
- Authority
- DE
- Germany
- Prior art keywords
- benzoic acid
- aniline
- phenylamino
- alkali metal
- hexamethyldisilazide
- 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.)
- Expired - Fee Related
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 50
- 235000010233 benzoic acid Nutrition 0.000 title claims description 26
- 239000005711 Benzoic acid Substances 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- -1 alkali metal hexamethyldisilazide Chemical class 0.000 claims description 17
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical group [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WEPXLRANFJEOFZ-UHFFFAOYSA-N 2,3,4-trifluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1F WEPXLRANFJEOFZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- MYDAOWXYGPEPJT-UHFFFAOYSA-N 2-chloro-4-iodoaniline Chemical group NC1=CC=C(I)C=C1Cl MYDAOWXYGPEPJT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- XGIUDIMNNMKGDE-UHFFFAOYSA-N bis(trimethylsilyl)azanide Chemical compound C[Si](C)(C)[N-][Si](C)(C)C XGIUDIMNNMKGDE-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 239000012820 MEK1 Inhibitor Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13038499P | 1999-04-21 | 1999-04-21 | |
| US130384P | 1999-04-21 | ||
| PCT/US2000/003982 WO2000064856A1 (en) | 1999-04-21 | 2000-02-16 | Method for making 2-(n-phenylamino)benzoic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60017109D1 DE60017109D1 (de) | 2005-02-03 |
| DE60017109T2 true DE60017109T2 (de) | 2006-01-12 |
Family
ID=22444462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60017109T Expired - Fee Related DE60017109T2 (de) | 1999-04-21 | 2000-02-16 | Verfahren zur herstellung von 2-(n-phenylalmino)benzoesäure |
Country Status (34)
| Country | Link |
|---|---|
| EP (1) | EP1171418B1 (https=) |
| JP (1) | JP3769192B2 (https=) |
| KR (1) | KR20010108521A (https=) |
| CN (1) | CN1213997C (https=) |
| AP (1) | AP2001002328A0 (https=) |
| AT (1) | ATE286015T1 (https=) |
| AU (1) | AU773096B2 (https=) |
| BG (1) | BG106132A (https=) |
| BR (1) | BR0009886A (https=) |
| CA (1) | CA2368807A1 (https=) |
| CR (1) | CR6486A (https=) |
| CU (1) | CU22996A3 (https=) |
| DE (1) | DE60017109T2 (https=) |
| DK (1) | DK1171418T3 (https=) |
| EA (1) | EA004209B1 (https=) |
| EE (1) | EE200100546A (https=) |
| ES (1) | ES2235843T3 (https=) |
| GE (1) | GEP20033089B (https=) |
| HK (1) | HK1045682B (https=) |
| HR (1) | HRP20010850A2 (https=) |
| HU (1) | HUP0200932A3 (https=) |
| IL (1) | IL146056A0 (https=) |
| MA (1) | MA25412A1 (https=) |
| NO (1) | NO20015095D0 (https=) |
| NZ (1) | NZ515120A (https=) |
| OA (1) | OA11861A (https=) |
| PL (1) | PL351085A1 (https=) |
| PT (1) | PT1171418E (https=) |
| SK (1) | SK14732001A3 (https=) |
| TR (1) | TR200103015T2 (https=) |
| UA (1) | UA70995C2 (https=) |
| WO (1) | WO2000064856A1 (https=) |
| YU (1) | YU73701A (https=) |
| ZA (1) | ZA200107834B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030059115A (ko) * | 2000-08-25 | 2003-07-07 | 워너-램버트 캄파니 엘엘씨 | Ｎ-아릴-안트라닐산 및 그의 유도체의 제조 방법 |
| WO2006109661A1 (ja) | 2005-04-06 | 2006-10-19 | Chugai Seiyaku Kabushiki Kaisha | ２，３，４－トリフルオロ－５－（ヨード又はブロモ）安息香酸の製造方法 |
| WO2007021001A1 (ja) * | 2005-08-18 | 2007-02-22 | Ube Industries, Ltd. | ２，３，４－トリフルオロ－５－置換安息香酸化合物及びその製法 |
| CN102958892A (zh) * | 2010-02-19 | 2013-03-06 | 国家科学研究中心 | 通过芳香族亲核取代来制备目的化合物的方法 |
| CA2789373A1 (en) * | 2010-02-19 | 2011-08-25 | Centre National De La Recherche Scientifique | Process for preparing chemical compounds of interest by nucleophilic aromatic substitution of aromatic carboxylic acid derivatives supporting at least one electro-attractive group |
| JP2016034900A (ja) * | 2012-11-26 | 2016-03-17 | 中外製薬株式会社 | ５−置換−２−フェニルアミノ−ベンズアミド類の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ501276A (en) * | 1997-07-01 | 2000-10-27 | Warner Lambert Co | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors in treating proliferative disorders |
-
2000
- 2000-02-16 DE DE60017109T patent/DE60017109T2/de not_active Expired - Fee Related
- 2000-02-16 GE GEAP20006152A patent/GEP20033089B/en unknown
- 2000-02-16 IL IL14605600A patent/IL146056A0/xx unknown
- 2000-02-16 KR KR1020017013402A patent/KR20010108521A/ko not_active Ceased
- 2000-02-16 PL PL00351085A patent/PL351085A1/xx not_active IP Right Cessation
- 2000-02-16 HK HK02107069.9A patent/HK1045682B/zh not_active IP Right Cessation
- 2000-02-16 EA EA200101113A patent/EA004209B1/ru not_active IP Right Cessation
- 2000-02-16 ES ES00913489T patent/ES2235843T3/es not_active Expired - Lifetime
- 2000-02-16 AT AT00913489T patent/ATE286015T1/de not_active IP Right Cessation
- 2000-02-16 WO PCT/US2000/003982 patent/WO2000064856A1/en not_active Ceased
- 2000-02-16 YU YU73701A patent/YU73701A/sh unknown
- 2000-02-16 CN CNB008064423A patent/CN1213997C/zh not_active Expired - Fee Related
- 2000-02-16 TR TR2001/03015T patent/TR200103015T2/xx unknown
- 2000-02-16 UA UA2001096639A patent/UA70995C2/uk unknown
- 2000-02-16 JP JP2000613809A patent/JP3769192B2/ja not_active Expired - Fee Related
- 2000-02-16 HU HU0200932A patent/HUP0200932A3/hu unknown
- 2000-02-16 DK DK00913489T patent/DK1171418T3/da active
- 2000-02-16 SK SK1473-2001A patent/SK14732001A3/sk unknown
- 2000-02-16 AP APAP/P/2001/002328A patent/AP2001002328A0/en unknown
- 2000-02-16 PT PT00913489T patent/PT1171418E/pt unknown
- 2000-02-16 OA OA1200100260A patent/OA11861A/en unknown
- 2000-02-16 AU AU34928/00A patent/AU773096B2/en not_active Ceased
- 2000-02-16 CA CA002368807A patent/CA2368807A1/en not_active Abandoned
- 2000-02-16 NZ NZ515120A patent/NZ515120A/en unknown
- 2000-02-16 EE EEP200100546A patent/EE200100546A/xx unknown
- 2000-02-16 BR BR0009886-8A patent/BR0009886A/pt not_active IP Right Cessation
- 2000-02-16 EP EP00913489A patent/EP1171418B1/en not_active Expired - Lifetime
- 2000-02-16 HR HR20010850A patent/HRP20010850A2/hr not_active Application Discontinuation
-
2001
- 2001-09-21 ZA ZA200107834A patent/ZA200107834B/en unknown
- 2001-09-21 CU CU20010213A patent/CU22996A3/es unknown
- 2001-10-19 NO NO20015095A patent/NO20015095D0/no not_active Application Discontinuation
- 2001-10-19 CR CR6486A patent/CR6486A/es not_active Application Discontinuation
- 2001-11-16 MA MA26413A patent/MA25412A1/fr unknown
- 2001-11-21 BG BG106132A patent/BG106132A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |