GB1139332A - Substituted phenylacetic acids and processes for their production - Google Patents
Substituted phenylacetic acids and processes for their productionInfo
- Publication number
- GB1139332A GB1139332A GB15497/66A GB1549766A GB1139332A GB 1139332 A GB1139332 A GB 1139332A GB 15497/66 A GB15497/66 A GB 15497/66A GB 1549766 A GB1549766 A GB 1549766A GB 1139332 A GB1139332 A GB 1139332A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- alkyl
- compounds
- radical
- formula
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1,139,332. Amino-phenylacetic acids and their salts. J. R. GEIGY A.G. 7 April, 1966 [8 April, 1965], No. 15497/66. Heading C2C. [Also in Division A5] The invention comprises substituted aminophenylacetic acids of the general formula wherein R 1 represents a C 1-4 alkyl or alkoxy radical, a halogen atom up to the atomic number 35 or the trifluoromethyl group; R 2 and R 3 each represent hydrogen, a C 1-4 alkyl or alkoxy radical or a halogen atom up to atomic number 35, R 4 represents hydrogen, a low alkyl or alkoxy radical, a halogen atom up to atomic number 35 or the trifluoromethyl group, and R 5 and R 6 each represent hydrogen, a low alkyl radical or a benzyl radical, and their salts with inorganic and organic bases. The novel compounds may be made by heating a compound of the general formula with an alkali metal hydroxide or carbonate or an alkaline earth metal hydroxide and, if desired, liberating the acid from the salt. Alternatively, a compound of general formula wherein A represents hydrogen or a carboxylic acyl radical, and R 7 represents a C 1-4 alkyl, or aralkyl, particularly benzyl, radical, is heated with an alkali metal hydroxide, carbonate or bicarbonate, an alkaline earth metal hydroxide or a basic ion-exchanger, or if R 7 is the benzyl radical, splitting this off by catalytic hydrogenolysis. As a further alternative, a compound of general formula is heated with an alkali metal hydroxide in an aqueous solvent. The 1-aryl-2-indolinones (II) are also novel and may be made by chloracetylating corresponding unsymmetrically substituted diphenylamines to form substituted 2-chloro-N-phenyl acetanilides and heating the latter with aluminium chloride. The radicals R 5 and R 6 can be introduced by alkylation with an alkyl halide or dialkyl sulphate or an aralkyl halide. A benzyl radical may be introduced by reaction with benzaldehyde and reduction of the benzal so formed. Compounds of Formula II where R 5 is low alkyl and R 6 is a hydrogen atom are made by reacting α-halogen alkanoic acid halides with substituted diphenylamines and then closing the ring. Compounds of Formula II are also obtained by saponification of compounds of Formulµ III and IV whereby ring closure occurs. Compounds of Formula III are obtained by converting the corresponding cyano compounds into imino-ether hydrochlorides and decomposing these with water. They can also be made by treating acids of Formula I with diazo alkanes or dialkyl sulphates, or with an aralkyl alcohol and N,N-dimethyl formamide neopentyl acetal, or with thionyl chloride at - 10‹ C. in abs. alkyl or aralkyl alcohol. Compounds of Formula IV are made by reacting α-halogen-N-aryl-o-toluidines or toluidides with sodium or potassium cyanide. α-Chloro-otoluidines or toluidides are made from o-arylamino-benzyl alcohols by boiling with acetyl chloride. The o-aryl-amino-benzyl alcohols are made by reduction of N-aryl-anthranilic acid alkyl esters with lithium aluminium hydride in ether or tetrahydrofuran, sodium borohydride in methanol or sodium borohydride and lithium bromide in diglyme. Diphenylamines substituted by R 1 to R 4 can be made by decarboxylating corresponding o-anilinobenzoic acids, or by reacting a substituted acetanilide with an R 4 - substituted bromobenzene. The substituted acetanilides are made by reacting the appropriate substituted aniline with acetyl chloride in glacial acetic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH496165A CH460804A (en) | 1965-04-08 | 1965-04-08 | Process for the production of new substituted phenylacetic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1139332A true GB1139332A (en) | 1969-01-08 |
Family
ID=4285534
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15497/66A Expired GB1139332A (en) | 1965-04-08 | 1966-04-07 | Substituted phenylacetic acids and processes for their production |
Country Status (16)
Country | Link |
---|---|
AT (4) | AT263755B (en) |
BE (1) | BE679315A (en) |
CH (1) | CH460804A (en) |
CY (1) | CY637A (en) |
DE (1) | DE1543639B2 (en) |
DK (1) | DK117639B (en) |
DO (2) | DOP1977002615A (en) |
ES (2) | ES325271A1 (en) |
FI (1) | FI44619C (en) |
FR (2) | FR1487352A (en) |
GB (1) | GB1139332A (en) |
IL (1) | IL25545A (en) |
MY (1) | MY7200118A (en) |
NL (2) | NL6604752A (en) |
NO (1) | NO120793B (en) |
SE (1) | SE322527B (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2124077A (en) * | 1982-05-11 | 1984-02-15 | Mitsubishi Chem Ind | Immunomodulating agent |
EP0400558A2 (en) * | 1989-05-29 | 1990-12-05 | Laboratorios Vinas S.A. | Phenylacetic acid derivative |
US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
US5347036A (en) * | 1985-07-22 | 1994-09-13 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
WO2001003684A2 (en) * | 1999-07-08 | 2001-01-18 | Exocell, Inc. | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
US8362294B2 (en) | 2006-06-26 | 2013-01-29 | Novartis Ag | Phenylacetic acid derivatives |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513199A (en) * | 1967-05-05 | 1970-05-19 | Smithkline Corp | Substituted anilino benzyl alcohols |
CH506480A (en) * | 1969-02-20 | 1971-04-30 | Ciba Geigy Ag | Process for the production of new, substituted o-anilino-phenethyl alcohols |
JPS549240A (en) * | 1977-06-23 | 1979-01-24 | Asahi Chem Ind Co Ltd | New derivative of phenylglycolic acid, its preparation and analgesic and antiinflammatory agent contining it as effective component |
DE3623193A1 (en) * | 1986-07-10 | 1988-01-14 | Gruenenthal Gmbh | NEW COMPOUNDS, THIS MEDICINAL PRODUCT AND METHOD FOR THE PRODUCTION THEREOF |
EP0405602A1 (en) * | 1989-06-30 | 1991-01-02 | Laboratorios Vinas S.A. | New Zinc derivatives of anti-inflammatory drugs having improved therapeutic activity |
CN114516813A (en) | 2022-02-25 | 2022-05-20 | 复旦大学 | Continuous flow preparation method of diclofenac sodium |
CN114539086B (en) | 2022-02-25 | 2023-10-03 | 复旦大学 | Synthesis method of diclofenac sodium |
-
0
- NL NL133740D patent/NL133740C/xx active
-
1965
- 1965-04-08 FR FR57111A patent/FR1487352A/en not_active Expired
- 1965-04-08 CH CH496165A patent/CH460804A/en unknown
-
1966
- 1966-04-06 NO NO162524A patent/NO120793B/no unknown
- 1966-04-06 FI FI660898A patent/FI44619C/en active
- 1966-04-06 ES ES0325271A patent/ES325271A1/en not_active Expired
- 1966-04-06 DK DK180566AA patent/DK117639B/en unknown
- 1966-04-06 ES ES0325270A patent/ES325270A1/en not_active Expired
- 1966-04-07 DE DE1966G0046553 patent/DE1543639B2/en active Granted
- 1966-04-07 AT AT334966A patent/AT263755B/en active
- 1966-04-07 NL NL6604752A patent/NL6604752A/xx unknown
- 1966-04-07 AT AT619767A patent/AT266096B/en active
- 1966-04-07 SE SE4833/66A patent/SE322527B/xx unknown
- 1966-04-07 IL IL25545A patent/IL25545A/en unknown
- 1966-04-07 AT AT619567A patent/AT262982B/en active
- 1966-04-07 GB GB15497/66A patent/GB1139332A/en not_active Expired
- 1966-04-07 AT AT619667A patent/AT262983B/en active
- 1966-04-08 BE BE679315D patent/BE679315A/xx not_active IP Right Cessation
- 1966-07-06 FR FR68443A patent/FR5524M/fr not_active Expired
-
1972
- 1972-04-19 CY CY63772A patent/CY637A/en unknown
- 1972-12-31 MY MY1972118A patent/MY7200118A/en unknown
-
1977
- 1977-11-21 DO DO1977002615A patent/DOP1977002615A/en unknown
- 1977-12-09 DO DO1977002614A patent/DOP1977002614A/en unknown
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2124077A (en) * | 1982-05-11 | 1984-02-15 | Mitsubishi Chem Ind | Immunomodulating agent |
US5495043A (en) * | 1985-07-22 | 1996-02-27 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
US5347036A (en) * | 1985-07-22 | 1994-09-13 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
US5416113A (en) * | 1985-07-22 | 1995-05-16 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
US5498745A (en) * | 1985-07-22 | 1996-03-12 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
US5527824A (en) * | 1985-07-22 | 1996-06-18 | Riker Laboratories, Inc. | Substituted Di-T-Butlyphenols useful for inhibiting leukotriene synthesis |
EP0400558A3 (en) * | 1989-05-29 | 1992-03-04 | Laboratorios Vinas S.A. | Phenylacetic acid derivative |
EP0400558A2 (en) * | 1989-05-29 | 1990-12-05 | Laboratorios Vinas S.A. | Phenylacetic acid derivative |
US6552077B2 (en) | 1996-02-20 | 2003-04-22 | Exocell, Inc. | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
WO2001003684A2 (en) * | 1999-07-08 | 2001-01-18 | Exocell, Inc. | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
WO2001003684A3 (en) * | 1999-07-08 | 2002-06-06 | Exocell Inc | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
US8362294B2 (en) | 2006-06-26 | 2013-01-29 | Novartis Ag | Phenylacetic acid derivatives |
US8586782B2 (en) | 2006-06-26 | 2013-11-19 | Novartis Ag | Phenylacetic acid derivatives |
Also Published As
Publication number | Publication date |
---|---|
AT263755B (en) | 1968-08-12 |
FI44619C (en) | 1971-12-10 |
FI44619B (en) | 1971-08-31 |
FR5524M (en) | 1967-11-06 |
AT262982B (en) | 1968-07-10 |
DE1543639B2 (en) | 1977-02-24 |
MY7200118A (en) | 1972-12-31 |
NL6604752A (en) | 1966-10-10 |
DOP1977002615A (en) | 1983-05-27 |
NO120793B (en) | 1970-12-07 |
CY637A (en) | 1972-04-19 |
DE1543639A1 (en) | 1970-02-05 |
DE1793592A1 (en) | 1972-04-20 |
AT266096B (en) | 1968-11-11 |
DK117639B (en) | 1970-05-19 |
DOP1977002614A (en) | 1983-05-27 |
FR1487352A (en) | 1967-07-07 |
IL25545A (en) | 1970-07-19 |
AT262983B (en) | 1968-07-10 |
ES325270A1 (en) | 1967-04-01 |
DE1793592B2 (en) | 1977-06-16 |
CH460804A (en) | 1968-08-15 |
ES325271A1 (en) | 1967-04-01 |
SE322527B (en) | 1970-04-13 |
BE679315A (en) | 1966-10-10 |
NL133740C (en) |
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