CA1066303A - Aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the same - Google Patents
Aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the sameInfo
- Publication number
- CA1066303A CA1066303A CA254,544A CA254544A CA1066303A CA 1066303 A CA1066303 A CA 1066303A CA 254544 A CA254544 A CA 254544A CA 1066303 A CA1066303 A CA 1066303A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- carboxy
- chloroanthranilic
- preparing
- small amount
- 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
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
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- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 6
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- 230000001939 inductive effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000528 statistical test Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526092A DE2526092C2 (de) | 1975-06-11 | 1975-06-11 | Aminobenzoesäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JP51041041A JPS606355B2 (ja) | 1975-06-11 | 1976-04-12 | 新規アミノ安息香酸誘導体、その製法及び医薬組成物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1066303A true CA1066303A (en) | 1979-11-13 |
Family
ID=25769022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,544A Expired CA1066303A (en) | 1975-06-11 | 1976-06-10 | Aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the same |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4092426A (OSRAM) |
| AR (1) | AR212814A1 (OSRAM) |
| CA (1) | CA1066303A (OSRAM) |
| CH (1) | CH630605A5 (OSRAM) |
| ES (1) | ES448761A1 (OSRAM) |
| FI (1) | FI62283C (OSRAM) |
| FR (1) | FR2313921A1 (OSRAM) |
| GB (1) | GB1520179A (OSRAM) |
| NL (1) | NL185405C (OSRAM) |
| SE (1) | SE412907B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5791914A (en) * | 1980-11-28 | 1982-06-08 | Chugai Pharmaceut Co Ltd | Peptic unti-ulcer |
| GB2171012B (en) * | 1985-01-22 | 1989-01-05 | Chugai Pharmaceutical Co Ltd | Nephritis treating agent |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3390172A (en) * | 1964-03-27 | 1968-06-25 | Parke Davis & Co | Nu-(3-trifluoromethylphenyl)-anthranilic acids |
| US3369042A (en) * | 1964-04-07 | 1968-02-13 | Parke Davis & Co | N-(substituted phenyl)anthranilic acids, salts, and esters thereof |
| US3313848A (en) * | 1964-06-18 | 1967-04-11 | Parke Davis & Co | Anthranilic acids and derivatives |
| IT1061780B (it) * | 1966-09-03 | 1983-04-30 | Italfarmaco Spa | Acido n 4 carbossifenil antrantiico suoi derivati e processo per la loro preparazione |
| JPS5230511B2 (OSRAM) * | 1972-05-11 | 1977-08-09 |
-
1976
- 1976-06-01 US US05/691,432 patent/US4092426A/en not_active Expired - Lifetime
- 1976-06-04 GB GB23299/76A patent/GB1520179A/en not_active Expired
- 1976-06-10 SE SE7606592A patent/SE412907B/xx not_active IP Right Cessation
- 1976-06-10 ES ES448761A patent/ES448761A1/es not_active Expired
- 1976-06-10 CA CA254,544A patent/CA1066303A/en not_active Expired
- 1976-06-10 CH CH738076A patent/CH630605A5/de not_active IP Right Cessation
- 1976-06-11 FR FR7617799A patent/FR2313921A1/fr active Granted
- 1976-06-11 NL NLAANVRAGE7606309,A patent/NL185405C/xx not_active IP Right Cessation
- 1976-06-11 FI FI761677A patent/FI62283C/fi not_active IP Right Cessation
-
1978
- 1978-01-01 AR AR21281478D patent/AR212814A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AR212814A1 (es) | 1978-10-13 |
| GB1520179A (en) | 1978-08-02 |
| NL7606309A (nl) | 1976-12-14 |
| NL185405C (nl) | 1990-04-02 |
| ES448761A1 (es) | 1977-12-16 |
| SE412907B (sv) | 1980-03-24 |
| US4092426A (en) | 1978-05-30 |
| FI761677A7 (OSRAM) | 1976-12-12 |
| FI62283B (fi) | 1982-08-31 |
| CH630605A5 (de) | 1982-06-30 |
| NL185405B (nl) | 1989-11-01 |
| SE7606592L (sv) | 1976-12-12 |
| FI62283C (fi) | 1982-12-10 |
| FR2313921A1 (fr) | 1977-01-07 |
| FR2313921B1 (OSRAM) | 1979-09-28 |
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