SK14732001A3 - Spôsob výroby kyselín 2-(N-fenylamino)benzoových - Google Patents

Spôsob výroby kyselín 2-(N-fenylamino)benzoových Download PDF

Info

Publication number: SK14732001A3
Authority: SK; Slovakia
Prior art keywords: benzoic acid; aniline; phenylamino; alkali metal; benzoic
Prior art date: 1999-04-21

Application number

SK1473-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Michael Huai Gu Chen

Javier Magano

Original Assignee

Warner-Lambert Company

Priority date (The priority date 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 date listed.)

1999-04-21

Filing date

2000-02-16

Publication date

2002-05-09

2000-02-16 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2002-05-09 Publication of SK14732001A3 publication Critical patent/SK14732001A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 32
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 53
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 46
235000010233 benzoic acid Nutrition 0.000 claims abstract description 27
239000005711 Benzoic acid Substances 0.000 claims abstract description 26
ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 claims abstract description 16
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 19
-1 alkali metal hexamethyldisilazide Chemical class 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
229910052783 alkali metal Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
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
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 1
238000005859 coupling reaction Methods 0.000 abstract description 7
230000008878 coupling Effects 0.000 abstract description 3
238000010168 coupling process Methods 0.000 abstract description 3
XGIUDIMNNMKGDE-UHFFFAOYSA-N bis(trimethylsilyl)azanide Chemical compound C[Si](C)(C)[N-][Si](C)(C)C XGIUDIMNNMKGDE-UHFFFAOYSA-N 0.000 abstract 1
239000002184 metal Substances 0.000 abstract 1
239000002585 base Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
150000001448 anilines Chemical class 0.000 description 4
125000000896 monocarboxylic acid group Chemical group 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
125000005843 halogen group Chemical group 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
BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
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
102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 1
101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
NNNDGNSOCBWTJG-UHFFFAOYSA-N aniline;benzoic acid Chemical compound NC1=CC=CC=C1.OC(=O)C1=CC=CC=C1 NNNDGNSOCBWTJG-UHFFFAOYSA-N 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
230000000694 effects Effects 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
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
238000011084 recovery Methods 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)

SK1473-2001A 1999-04-21 2000-02-16 Spôsob výroby kyselín 2-(N-fenylamino)benzoových SK14732001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13038499P	1999-04-21	1999-04-21
PCT/US2000/003982 WO2000064856A1 (en)	1999-04-21	2000-02-16	Method for making 2-(n-phenylamino)benzoic acids

Publications (1)

Publication Number	Publication Date
SK14732001A3 true SK14732001A3 (sk)	2002-05-09

Family

ID=22444462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1473-2001A SK14732001A3 (sk)	1999-04-21	2000-02-16	Spôsob výroby kyselín 2-(N-fenylamino)benzoových

Country Status (34)

Country	Link
EP (1)	EP1171418B1 (de)
JP (1)	JP3769192B2 (de)
KR (1)	KR20010108521A (de)
CN (1)	CN1213997C (de)
AP (1)	AP2001002328A0 (de)
AT (1)	ATE286015T1 (de)
AU (1)	AU773096B2 (de)
BG (1)	BG106132A (de)
BR (1)	BR0009886A (de)
CA (1)	CA2368807A1 (de)
CR (1)	CR6486A (de)
CU (1)	CU22996A3 (de)
DE (1)	DE60017109T2 (de)
DK (1)	DK1171418T3 (de)
EA (1)	EA004209B1 (de)
EE (1)	EE200100546A (de)
ES (1)	ES2235843T3 (de)
GE (1)	GEP20033089B (de)
HK (1)	HK1045682B (de)
HR (1)	HRP20010850A2 (de)
HU (1)	HUP0200932A3 (de)
IL (1)	IL146056A0 (de)
MA (1)	MA25412A1 (de)
NO (1)	NO20015095L (de)
NZ (1)	NZ515120A (de)
OA (1)	OA11861A (de)
PL (1)	PL351085A1 (de)
PT (1)	PT1171418E (de)
SK (1)	SK14732001A3 (de)
TR (1)	TR200103015T2 (de)
UA (1)	UA70995C2 (de)
WO (1)	WO2000064856A1 (de)
YU (1)	YU73701A (de)
ZA (1)	ZA200107834B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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
JPWO2007021001A1 (ja) *	2005-08-18	2009-02-26	宇部興産株式会社	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
CN102985399A (zh) *	2010-02-19	2013-03-20	国家科学研究中心	通过对携带至少一个吸电子基团的芳香族羧酸衍生物进行亲核芳香族取代来制备目的化合物的方法
WO2011101599A1 (fr) *	2010-02-19	2011-08-25	Centre National De La Recherche Scientifique	Procédé de préparation de composés chimiques d'intérêt par substitution nucléophile aromatique
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU757046B2 (en) *	1997-07-01	2003-01-30	Warner-Lambert Company	4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors

2000
- 2000-02-16 PL PL00351085A patent/PL351085A1/xx not_active IP Right Cessation
- 2000-02-16 YU YU73701A patent/YU73701A/sh unknown
- 2000-02-16 TR TR2001/03015T patent/TR200103015T2/xx unknown
- 2000-02-16 OA OA1200100260A patent/OA11861A/en unknown
- 2000-02-16 DE DE60017109T patent/DE60017109T2/de not_active Expired - Fee Related
- 2000-02-16 KR KR1020017013402A patent/KR20010108521A/ko not_active Ceased
- 2000-02-16 EP EP00913489A patent/EP1171418B1/de not_active Expired - Lifetime
- 2000-02-16 ES ES00913489T patent/ES2235843T3/es not_active Expired - Lifetime
- 2000-02-16 IL IL14605600A patent/IL146056A0/xx unknown
- 2000-02-16 GE GEAP20006152A patent/GEP20033089B/en unknown
- 2000-02-16 CA CA002368807A patent/CA2368807A1/en not_active Abandoned
- 2000-02-16 JP JP2000613809A patent/JP3769192B2/ja not_active Expired - Fee Related
- 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 PT PT00913489T patent/PT1171418E/pt unknown
- 2000-02-16 AU AU34928/00A patent/AU773096B2/en not_active Ceased
- 2000-02-16 BR BR0009886-8A patent/BR0009886A/pt not_active IP Right Cessation
- 2000-02-16 AT AT00913489T patent/ATE286015T1/de not_active IP Right Cessation
- 2000-02-16 HU HU0200932A patent/HUP0200932A3/hu unknown
- 2000-02-16 DK DK00913489T patent/DK1171418T3/da active
- 2000-02-16 AP APAP/P/2001/002328A patent/AP2001002328A0/en unknown
- 2000-02-16 UA UA2001096639A patent/UA70995C2/uk unknown
- 2000-02-16 SK SK1473-2001A patent/SK14732001A3/sk unknown
- 2000-02-16 EE EEP200100546A patent/EE200100546A/xx unknown
- 2000-02-16 HR HR20010850A patent/HRP20010850A2/hr not_active Application Discontinuation
- 2000-02-16 NZ NZ515120A patent/NZ515120A/en unknown
- 2000-02-16 CN CNB008064423A patent/CN1213997C/zh not_active Expired - Fee Related
- 2000-02-16 WO PCT/US2000/003982 patent/WO2000064856A1/en not_active Ceased
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/NO20015095L/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

Also Published As

Publication number	Publication date
JP3769192B2 (ja)	2006-04-19
AU773096B2 (en)	2004-05-13
WO2000064856A1 (en)	2000-11-02
UA70995C2 (uk)	2004-11-15
CU22996A3 (es)	2004-10-12
HUP0200932A3 (en)	2002-11-28
MA25412A1 (fr)	2002-04-01
EA004209B1 (ru)	2004-02-26
HK1045682B (zh)	2006-04-07
NO20015095D0 (no)	2001-10-19
NZ515120A (en)	2003-08-29
HK1045682A1 (en)	2002-12-06
CN1213997C (zh)	2005-08-10
ZA200107834B (en)	2002-12-23
CR6486A (es)	2004-03-11
IL146056A0 (en)	2002-07-25
ES2235843T3 (es)	2005-07-16
EP1171418A1 (de)	2002-01-16
BG106132A (en)	2002-06-28
HUP0200932A2 (hu)	2002-07-29
EE200100546A (et)	2003-02-17
TR200103015T2 (tr)	2002-01-21
NO20015095L (no)	2001-10-19
CN1347403A (zh)	2002-05-01
JP2002543055A (ja)	2002-12-17
HRP20010850A2 (en)	2002-12-31
EP1171418B1 (de)	2004-12-29
ATE286015T1 (de)	2005-01-15
OA11861A (en)	2006-03-02
AU3492800A (en)	2000-11-10
KR20010108521A (ko)	2001-12-07
GEP20033089B (en)	2003-10-27
PT1171418E (pt)	2005-02-28
CA2368807A1 (en)	2000-11-02
DE60017109D1 (de)	2005-02-03
PL351085A1 (en)	2003-03-24
EA200101113A1 (ru)	2002-04-25
AP2001002328A0 (en)	2001-12-31
YU73701A (sh)	2005-06-10
DK1171418T3 (da)	2005-05-09
DE60017109T2 (de)	2006-01-12
BR0009886A (pt)	2002-01-22

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