GB989951A - Anti-inflammatory pharmaceutical compositions containing n-phenyl anthranilic acid derivatives - Google Patents
Anti-inflammatory pharmaceutical compositions containing n-phenyl anthranilic acid derivativesInfo
- Publication number
- GB989951A GB989951A GB2272761A GB2272761A GB989951A GB 989951 A GB989951 A GB 989951A GB 2272761 A GB2272761 A GB 2272761A GB 2272761 A GB2272761 A GB 2272761A GB 989951 A GB989951 A GB 989951A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- group
- hydrogen
- halogen
- general 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
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-Phenylanthranilic acid derivatives of the general formula <FORM:0989951/C2/1> (wherein R1 is a halogen atom or a methyl group; R2 is a halogen atom or a methyl or ethyl group; R3 and R5 are each hydrogen or halogen atoms or methyl groups, R5 not being hydrogen when R3 is halogen; R4 is a hydrogen or halogen atom, R4 and R3 both being hydrogen when R1 and R2 are both methyl; and at least one of R3, R4 and R5 being a hydrogen atom) are prepared by reacting an o-halogenated benzoic acid compound of general formula <FORM:0989951/C2/2> wherein M is hydrogen or a metal and X is halogen, with a compound of the general formula <FORM:0989951/C2/3> in the presence of a copper-containing catalyst and a proton acceptor. Alternatively, compounds of the Formula 1 above may be prepared by the hydrolysis of N-acylated diphenylamines of formula <FORM:0989951/C2/4> wherein R1-5 have the above meanings and R is a carboxy group or a group hydrolysable thereto (e.g. a cyano, carboalkoxy, carboaryloxy, carboarylalkoxy, carbamido or carbonyl halide group), which groups, and also the acyl group, may contain one or more substituents, e.g. C1-4 alkyl, C1-4 alkoxy, halogen, nitro, carboxy and carboalkoxy radicals. N - Phenyl - N - acyl - anthranilic acid compounds of Formula 4 above may be prepared by the following reaction sequences: (a) an anilide of the general formula <FORM:0989951/C2/5> in which R6 is a tertiary alkyl group or an aryl radical optionally substituted by one or more halogen, nitro, C1-4 alkyl, C1-4 alkoxy, carboxy and carboalkoxy groups and R7 is a cyano, carboxy, carboalkoxy, carboaryloxy, carboarylalkoxy or carbamido group is reacted with PCl5 to produce a benzimidoyl chloride of general formula <FORM:0989951/C2/6> which is reacted with a phenol compound of the general formula <FORM:0989951/C2/7> or an alkali metal salt thereof to give an imido imido ester of general formula <FORM:0989951/C2/8> which is heated to arrange intramolecularly to give an N-acylated diphenylamine of formula <FORM:0989951/C2/9> Alternatively, N-acylated diphenylamines of Formula 7 above in which R7 is cyano or carbamido may be prepared by reacting a compound of formula <FORM:0989951/C2/100> in which R8 is a cyano or carbamido group with thionyl chloride to produce the corresponding imino chloride of formula <FORM:0989951/C2/111> which is reacted with a phenol of general formula <FORM:0989951/C2/122> to produce an imidoester of formula <FORM:0989951/C2/133> which is rearranged by heat to obtain an N-acylated diphenylamine of formula <FORM:0989951/C2/144> The N-acylated-N-phenylanthranilic acid starting materials which contain non-oxidizable substituents in the N-phenyl ring can be prepared by the oxidation of a compound of formula <FORM:0989951/C2/155> wherein R9 is a radical oxidizable to a carboxyl group, Ar represents a phenyl ring containing non-oxidizable substituents R1, R2, R3, R4 and R5 and Acyl has the above meaning, such compounds being prepared from the o-R9-substituted -NCOR6 aniline and the corresponding substituted phenol as described above.ALSO:Anti-inflammatory pharmaceutical compositions comprise a carrier and a substantially chemically pure compound (or a pharmaceutically acceptable salt thereof) of general formula <FORM:0989951/A5-A6/1> wherein R1 is a halogen atom or a methyl group; R2 is a halogen atom or a methyl or ethyl group; R3 and R5 each represent a hydrogen atom or a methyl group, R5 being halogen or methyl when R3 is halogen; R4 is a hydrogen or halogen atom, R4 and R3 both being hydrogen when R1 and R2 are methyl groups; and at least one of R3, R4 and R5 is hydrogen. Specified salts are those with sodium, potassium, calcium, ammonium, choline, 2 - hydroxyethyl - ammonium, bis(2-hydroxyethyl)ammonium and tris-(2-hydroxyethyl) ammonium. The compositions may be in conventional forms suitable for oral and parenteral administration and may optionally comprise other anti-inflammatory agents such as corticosteroids, e.g. prednisone, prednisolone, cortisone, hydrocortisone and 9- or 12-halocorticosteroids.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38097A US3138636A (en) | 1960-06-23 | 1960-06-23 | Anthranilic acid derivatives |
US8218561A | 1961-01-12 | 1961-01-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB989951A true GB989951A (en) | 1965-04-22 |
Family
ID=26714852
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2272761A Expired GB989951A (en) | 1960-06-23 | 1961-06-22 | Anti-inflammatory pharmaceutical compositions containing n-phenyl anthranilic acid derivatives |
Country Status (3)
Country | Link |
---|---|
BE (2) | BE605302A (en) |
FR (9) | FR1249M (en) |
GB (1) | GB989951A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0053379A1 (en) * | 1980-11-28 | 1982-06-09 | Chugai Seiyaku Kabushiki Kaisha | Anti-peptic ulcer agent |
US5155110A (en) * | 1987-10-27 | 1992-10-13 | Warner-Lambert Company | Fenamic acid hydroxamate derivatives having cyclooxygenase and 5-lipoxygenase inhibition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1288123B1 (en) | 1996-09-04 | 1998-09-10 | Nicox Sa | USE OF NITRO-DERIVATIVES FOR URINARY INCONTINENCE |
-
1961
- 1961-06-22 FR FR865793A patent/FR1249M/en not_active Expired
- 1961-06-22 FR FR765794A patent/FR1250M/en not_active Expired
- 1961-06-22 FR FR865797A patent/FR1252M/en not_active Expired
- 1961-06-22 FR FR865796A patent/FR1416M/en not_active Expired
- 1961-06-22 BE BE605302D patent/BE605302A/xx unknown
- 1961-06-22 GB GB2272761A patent/GB989951A/en not_active Expired
- 1961-06-22 FR FR865795A patent/FR1251M/en not_active Expired
- 1961-06-22 BE BE605303D patent/BE605303A/xx unknown
- 1961-09-21 FR FR873839A patent/FR1381M/en not_active Expired
- 1961-09-21 FR FR873838A patent/FR1380M/en not_active Expired
- 1961-09-21 FR FR873840A patent/FR1382M/en not_active Expired
- 1961-09-21 FR FR873837A patent/FR1379M/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0053379A1 (en) * | 1980-11-28 | 1982-06-09 | Chugai Seiyaku Kabushiki Kaisha | Anti-peptic ulcer agent |
US5155110A (en) * | 1987-10-27 | 1992-10-13 | Warner-Lambert Company | Fenamic acid hydroxamate derivatives having cyclooxygenase and 5-lipoxygenase inhibition |
Also Published As
Publication number | Publication date |
---|---|
FR1416M (en) | 1962-08-31 |
FR1251M (en) | 1962-05-18 |
BE605302A (en) | 1961-10-16 |
FR1381M (en) | 1962-08-03 |
FR1379M (en) | 1962-08-03 |
FR1382M (en) | 1962-08-03 |
FR1249M (en) | 1962-05-18 |
BE605303A (en) | 1961-10-16 |
FR1252M (en) | 1962-05-18 |
FR1380M (en) | 1962-08-03 |
FR1250M (en) | 1962-05-18 |
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