OA11861A - Method for making 2-(N-phenylamino) benzoic acids. - Google Patents

Method for making 2-(N-phenylamino) benzoic acids. Download PDF

Info

Publication number: OA11861A
Authority: OA; OAPI
Prior art keywords: benzoic acid; phenylamino; aniline; hexamethyldisilazide; acid
Prior art date: 1999-04-21

Application number

OA1200100260A

Other languages

English (en)

Inventor

Michael Huai Gu Chen

Ann Arbor

Javier Magano

Original Assignee

Warner Lambert Co

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

2006-03-02

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

2006-03-02 Publication of OA11861A publication Critical patent/OA11861A/en

Links

238000000034 method Methods 0.000 title claims abstract description 39
ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 title claims abstract description 17
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 50
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 42
235000010233 benzoic acid Nutrition 0.000 claims abstract description 26
239000005711 Benzoic acid Substances 0.000 claims abstract description 25
XGIUDIMNNMKGDE-UHFFFAOYSA-N bis(trimethylsilyl)azanide Chemical compound C[Si](C)(C)[N-][Si](C)(C)C XGIUDIMNNMKGDE-UHFFFAOYSA-N 0.000 claims abstract description 11
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
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
125000001424 substituent group Chemical group 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
238000005859 coupling reaction Methods 0.000 abstract description 7
230000008878 coupling Effects 0.000 abstract description 4
238000010168 coupling process Methods 0.000 abstract description 4
239000002184 metal Substances 0.000 abstract 1
229960004365 benzoic acid Drugs 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 13
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
150000001875 compounds 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
150000001448 anilines Chemical class 0.000 description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
150000001559 benzoic acids Chemical class 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical class C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 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
WEPXLRANFJEOFZ-UHFFFAOYSA-N 2,3,4-trifluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1F WEPXLRANFJEOFZ-UHFFFAOYSA-N 0.000 description 1
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
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
239000012820 MEK1 Inhibitor Substances 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid 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
238000005580 one pot reaction Methods 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 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)

OA1200100260A 1999-04-21 2000-02-16 Method for making 2-(N-phenylamino) benzoic acids. OA11861A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US13038499P	1999-04-21	1999-04-21

Publications (1)

Publication Number	Publication Date
OA11861A true OA11861A (en)	2006-03-02

Family

ID=22444462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200100260A OA11861A (en)	1999-04-21	2000-02-16	Method for making 2-(N-phenylamino) benzoic acids.

Country Status (34)

Country	Link
EP (1)	EP1171418B1 (fr)
JP (1)	JP3769192B2 (fr)
KR (1)	KR20010108521A (fr)
CN (1)	CN1213997C (fr)
AP (1)	AP2001002328A0 (fr)
AT (1)	ATE286015T1 (fr)
AU (1)	AU773096B2 (fr)
BG (1)	BG106132A (fr)
BR (1)	BR0009886A (fr)
CA (1)	CA2368807A1 (fr)
CR (1)	CR6486A (fr)
CU (1)	CU22996A3 (fr)
DE (1)	DE60017109T2 (fr)
DK (1)	DK1171418T3 (fr)
EA (1)	EA004209B1 (fr)
EE (1)	EE200100546A (fr)
ES (1)	ES2235843T3 (fr)
GE (1)	GEP20033089B (fr)
HK (1)	HK1045682B (fr)
HR (1)	HRP20010850A2 (fr)
HU (1)	HUP0200932A3 (fr)
IL (1)	IL146056A0 (fr)
MA (1)	MA25412A1 (fr)
NO (1)	NO20015095D0 (fr)
NZ (1)	NZ515120A (fr)
OA (1)	OA11861A (fr)
PL (1)	PL351085A1 (fr)
PT (1)	PT1171418E (fr)
SK (1)	SK14732001A3 (fr)
TR (1)	TR200103015T2 (fr)
UA (1)	UA70995C2 (fr)
WO (1)	WO2000064856A1 (fr)
YU (1)	YU73701A (fr)
ZA (1)	ZA200107834B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AP2001002249A0 (en) *	2000-08-25	2001-09-30	Warner Lambert Co	Process for making N-ARYL-ANTHRANILIC acids and their derivatives.
TW200702329A (en) *	2005-04-06	2007-01-16	Chugai Pharmaceutical Co Ltd	A process for preparing 2,3,4-trifluoro-5-(iodo or bromo)benzoic acid
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
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
JP2013519715A (ja) *	2010-02-19	2013-05-30	センターナショナルデラリシェルシェサイエンティフィック	少なくとも１つの電子求引性基を有する芳香族カルボン酸誘導体の芳香族求核置換による目的の化学化合物の調製方法
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
ES2229515T3 (es) *	1997-07-01	2005-04-16	Warner-Lambert Company Llc	Derivados 4-bromo o 4-yodo del acido fenilamino benzhidroxamico y su uso como inhibidores de la mek.

2000
- 2000-02-16 WO PCT/US2000/003982 patent/WO2000064856A1/fr not_active Ceased
- 2000-02-16 DE DE60017109T patent/DE60017109T2/de not_active Expired - Fee Related
- 2000-02-16 IL IL14605600A patent/IL146056A0/xx unknown
- 2000-02-16 GE GEAP20006152A patent/GEP20033089B/en unknown
- 2000-02-16 KR KR1020017013402A patent/KR20010108521A/ko not_active Ceased
- 2000-02-16 SK SK1473-2001A patent/SK14732001A3/sk unknown
- 2000-02-16 PT PT00913489T patent/PT1171418E/pt unknown
- 2000-02-16 OA OA1200100260A patent/OA11861A/en unknown
- 2000-02-16 CN CNB008064423A patent/CN1213997C/zh not_active Expired - Fee Related
- 2000-02-16 BR BR0009886-8A patent/BR0009886A/pt not_active IP Right Cessation
- 2000-02-16 DK DK00913489T patent/DK1171418T3/da active
- 2000-02-16 YU YU73701A patent/YU73701A/sh unknown
- 2000-02-16 ES ES00913489T patent/ES2235843T3/es not_active Expired - Lifetime
- 2000-02-16 HK HK02107069.9A patent/HK1045682B/zh not_active IP Right Cessation
- 2000-02-16 UA UA2001096639A patent/UA70995C2/uk unknown
- 2000-02-16 EA EA200101113A patent/EA004209B1/ru not_active IP Right Cessation
- 2000-02-16 NZ NZ515120A patent/NZ515120A/en unknown
- 2000-02-16 JP JP2000613809A patent/JP3769192B2/ja not_active Expired - Fee Related
- 2000-02-16 EP EP00913489A patent/EP1171418B1/fr not_active Expired - Lifetime
- 2000-02-16 TR TR2001/03015T patent/TR200103015T2/xx unknown
- 2000-02-16 CA CA002368807A patent/CA2368807A1/fr not_active Abandoned
- 2000-02-16 AU AU34928/00A patent/AU773096B2/en not_active Ceased
- 2000-02-16 AP APAP/P/2001/002328A patent/AP2001002328A0/en unknown
- 2000-02-16 PL PL00351085A patent/PL351085A1/xx not_active IP Right Cessation
- 2000-02-16 HU HU0200932A patent/HUP0200932A3/hu unknown
- 2000-02-16 AT AT00913489T patent/ATE286015T1/de not_active IP Right Cessation
- 2000-02-16 HR HR20010850A patent/HRP20010850A2/hr not_active Application Discontinuation
- 2000-02-16 EE EEP200100546A patent/EE200100546A/xx unknown
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

Also Published As

Publication number	Publication date
NZ515120A (en)	2003-08-29
SK14732001A3 (sk)	2002-05-09
NO20015095L (no)	2001-10-19
JP3769192B2 (ja)	2006-04-19
DK1171418T3 (da)	2005-05-09
ATE286015T1 (de)	2005-01-15
HK1045682B (zh)	2006-04-07
EA004209B1 (ru)	2004-02-26
HK1045682A1 (en)	2002-12-06
YU73701A (sh)	2005-06-10
CR6486A (es)	2004-03-11
EA200101113A1 (ru)	2002-04-25
AU3492800A (en)	2000-11-10
HUP0200932A2 (hu)	2002-07-29
WO2000064856A1 (fr)	2000-11-02
BG106132A (en)	2002-06-28
KR20010108521A (ko)	2001-12-07
NO20015095D0 (no)	2001-10-19
AP2001002328A0 (en)	2001-12-31
MA25412A1 (fr)	2002-04-01
JP2002543055A (ja)	2002-12-17
HRP20010850A2 (en)	2002-12-31
EE200100546A (et)	2003-02-17
BR0009886A (pt)	2002-01-22
CA2368807A1 (fr)	2000-11-02
ZA200107834B (en)	2002-12-23
DE60017109D1 (de)	2005-02-03
CU22996A3 (es)	2004-10-12
DE60017109T2 (de)	2006-01-12
CN1347403A (zh)	2002-05-01
IL146056A0 (en)	2002-07-25
EP1171418A1 (fr)	2002-01-16
ES2235843T3 (es)	2005-07-16
CN1213997C (zh)	2005-08-10
TR200103015T2 (tr)	2002-01-21
PL351085A1 (en)	2003-03-24
GEP20033089B (en)	2003-10-27
PT1171418E (pt)	2005-02-28
AU773096B2 (en)	2004-05-13
HUP0200932A3 (en)	2002-11-28
EP1171418B1 (fr)	2004-12-29
UA70995C2 (uk)	2004-11-15

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