GB984120A - Anthranilic acid derivatives and methods for producing same - Google Patents
Anthranilic acid derivatives and methods for producing sameInfo
- Publication number
- GB984120A GB984120A GB22726/61A GB2272661A GB984120A GB 984120 A GB984120 A GB 984120A GB 22726/61 A GB22726/61 A GB 22726/61A GB 2272661 A GB2272661 A GB 2272661A GB 984120 A GB984120 A GB 984120A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- group
- methyl
- radical
- cooh
- 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
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- -1 acyl radical Chemical class 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000002463 imidates Chemical class 0.000 abstract 2
- 230000008707 rearrangement Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- MBISZJKAVPBLDT-UHFFFAOYSA-N 2,6-dichloro-3-ethylaniline Chemical compound CCC1=CC=C(Cl)C(N)=C1Cl MBISZJKAVPBLDT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- ZAQGLDMWELFZPL-UHFFFAOYSA-N 3,6-dichloro-2-methylaniline Chemical compound CC1=C(Cl)C=CC(Cl)=C1N ZAQGLDMWELFZPL-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 208000025747 Rheumatic disease Diseases 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 abstract 1
- IAHMNSCQDXESII-UHFFFAOYSA-N benzenecarboximidoyl chloride Chemical compound ClC(=N)C1=CC=CC=C1 IAHMNSCQDXESII-UHFFFAOYSA-N 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 abstract 1
- 229960001231 choline Drugs 0.000 abstract 1
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004820 halides Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052751 metal Chemical group 0.000 abstract 1
- 239000002184 metal Chemical group 0.000 abstract 1
- NALGTKRTIJHBBK-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(Cl)=C1C NALGTKRTIJHBBK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003254 radicals Chemical group 0.000 abstract 1
- 230000000552 rheumatic effect Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229960004418 trolamine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0984120/C2/1> (wherein R1 represents a chlorine atom or a methyl group and R2 a chlorine atom or a methyl or ethyl group, R2 being chlorine when R1 is methyl) and their salts, and the preparation thereof by condensing a benzoic acid derivatives of the general formula <FORM:0984120/C2/2> with a compound of the general formula <FORM:0984120/C2/3> (wherein Y and Z are different and represent -NH2 or a halogen atom and M represents hydrogen or a metal) or by hydrolysing (preferably under alkaline conditions) an N-acyldiphenylamine of the general formula <FORM:0984120/C2/4> (wherein Acyl represents an acyl radical, especially an optionally substituted benzoyl radical, and R represents a carboxyl group or a group hydrolysable thereto). N-Acyldiphenylamines of the last general formula above may be prepared as follows: (a) by reacting an anilide of the general formula <FORM:0984120/C2/5> (wherein R3 represents a tertiary alkyl group or an optionally substituted aryl radical) with phosphorus pentachloride to produce a benzimidoyl chloride of the general formula <FORM:0984120/C2/6> which is then reacted with an o-R4-phenol or alkali metal phenate (where R4 is a cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl or carbamido group) to form an imido-ester of the general formula <FORM:0984120/C2/7> from which the desired compounds is formed by thermal rearrangement; (b) (when R = CN) by treating an N-acylaniline of the general formula <FORM:0984120/C2/8> with thionyl chloride to obtain an iminochloride of the general formula <FORM:0984120/C2/9> which with an alkali metal salt of a phenol of the general formula <FORM:0984120/C2/100> yields an imido-ester of the general formula <FORM:0984120/C2/111> from which again the desired compounds is obtained by thermal rearrangement; (c) (when R = COOH and neither R1 nor R2 is an oxidizable substituent) by oxidizing a compound of the general formula <FORM:0984120/C2/122> (wherein R6 represents a radical oxidizable to COOH and Ar an o-chlorophenyl group containing non-oxidizable R1 and R2 substituents); (d) (when R is a carboxylic halide group) by treating the corresponding acid (R = COOH) with a halogenating agent. 2 - Methyl - 3,6 - dichloroaniline is prepared by brominating 2-methyl-3-chloroacetanilide in the 4-position, chlorinating the product in the 6-position, and removing the bromine atom by catalytic hydrogenolysis and the acetyl group by acid hydrolysis. 2,6 - Dichloro - 3 - ethylaniline is prepared analogously from 3-ethylacetanilide, using two molecular proportions of chlorine in the chlorination step. Pharmaceutical preparations, having antiinflammatory activity and suitable for heating rheumatic symptoms, comprise the compounds of the first general formula above, or their salts (e.g. alkali and alkaline-earth metal, ammonium, choline and mono-, di- and tri-ethanolamine salts), together with a solid or liquid carrier or diluent. They are preferably in forms suitable for oral administration, e.g. tablets, capsules, powders, dragees, suspensions or solutions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8218561A | 1961-01-12 | 1961-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB984120A true GB984120A (en) | 1965-02-24 |
Family
ID=22169584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22726/61A Expired GB984120A (en) | 1961-01-12 | 1961-06-22 | Anthranilic acid derivatives and methods for producing same |
Country Status (8)
| Country | Link |
|---|---|
| BR (1) | BR6130119D0 (en) |
| CH (2) | CH405348A (en) |
| DE (1) | DE1149015B (en) |
| DK (1) | DK105594C (en) |
| ES (1) | ES268522A1 (en) |
| FR (2) | FR1457258A (en) |
| GB (1) | GB984120A (en) |
| NL (2) | NL266265A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0301834A3 (en) * | 1987-07-29 | 1990-01-10 | IDB HOLDING S.p.A. | Derivatives of benzoyloxyacetic acid, and preparation and formulations thereof for therapeutic use |
| WO2016049790A1 (en) * | 2014-09-30 | 2016-04-07 | Pontificia Universidad Catolica De Chile | Method for producing pyrimido- or imidazo-quinoline-derived compounds from n-(2-cyanophenyl)benzimidoyl chloride with ethylenediamine or 1,3-diaminopropane |
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 |
-
0
- NL NL123122D patent/NL123122C/xx active
- NL NL266265D patent/NL266265A/xx unknown
-
1961
- 1961-06-19 BR BR130119/61A patent/BR6130119D0/en unknown
- 1961-06-22 DK DK186962AA patent/DK105594C/en active
- 1961-06-22 CH CH1440065A patent/CH405348A/en unknown
- 1961-06-22 FR FR865810A patent/FR1457258A/en not_active Expired
- 1961-06-22 GB GB22726/61A patent/GB984120A/en not_active Expired
- 1961-06-22 CH CH731261A patent/CH401992A/en unknown
- 1961-06-22 DE DEP27408A patent/DE1149015B/en active Pending
- 1961-06-22 ES ES268522A patent/ES268522A1/en not_active Expired
- 1961-09-21 FR FR873841A patent/FR1383M/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0301834A3 (en) * | 1987-07-29 | 1990-01-10 | IDB HOLDING S.p.A. | Derivatives of benzoyloxyacetic acid, and preparation and formulations thereof for therapeutic use |
| WO2016049790A1 (en) * | 2014-09-30 | 2016-04-07 | Pontificia Universidad Catolica De Chile | Method for producing pyrimido- or imidazo-quinoline-derived compounds from n-(2-cyanophenyl)benzimidoyl chloride with ethylenediamine or 1,3-diaminopropane |
Also Published As
| Publication number | Publication date |
|---|---|
| ES268522A1 (en) | 1962-04-16 |
| DE1149015B (en) | 1963-05-22 |
| FR1383M (en) | 1962-07-02 |
| NL123122C (en) | |
| CH401992A (en) | 1965-11-15 |
| DK105594C (en) | 1966-10-17 |
| NL266265A (en) | |
| FR1457258A (en) | 1966-01-24 |
| CH405348A (en) | 1966-01-15 |
| BR6130119D0 (en) | 1973-06-07 |
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