CA1189527A - Anti-inflammatory, analgesic, antipyretic, water- soluble compound and process for preparing the same - Google Patents
Anti-inflammatory, analgesic, antipyretic, water- soluble compound and process for preparing the sameInfo
- Publication number
- CA1189527A CA1189527A CA000405569A CA405569A CA1189527A CA 1189527 A CA1189527 A CA 1189527A CA 000405569 A CA000405569 A CA 000405569A CA 405569 A CA405569 A CA 405569A CA 1189527 A CA1189527 A CA 1189527A
- Authority
- CA
- Canada
- Prior art keywords
- water
- difluoro
- diphenyl
- preparing
- inflammatory
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 title description 6
- 230000003110 anti-inflammatory effect Effects 0.000 title description 4
- 230000000202 analgesic effect Effects 0.000 title description 2
- 230000001754 anti-pyretic effect Effects 0.000 title description 2
- 239000002221 antipyretic Substances 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 3
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical class N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229960000616 diflunisal Drugs 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- JXQCUCDXLSGQNZ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical class CC1=CC=C(C(C)(C)C)C(O)=C1C(O)=O JXQCUCDXLSGQNZ-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- -1 sqlves Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT48.719A/81 | 1981-06-19 | ||
| IT48719/81A IT1171318B (it) | 1981-06-19 | 1981-06-19 | Composto idrosolubile ad attivita' antinfiammatoria analgesica antipiretica e relativo procedimento di preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1189527A true CA1189527A (en) | 1985-06-25 |
Family
ID=11268237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000405569A Expired CA1189527A (en) | 1981-06-19 | 1982-06-21 | Anti-inflammatory, analgesic, antipyretic, water- soluble compound and process for preparing the same |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5843986A (ja) |
| BE (1) | BE893563A (ja) |
| CA (1) | CA1189527A (ja) |
| DE (1) | DE3223486A1 (ja) |
| ES (1) | ES8307832A1 (ja) |
| FR (1) | FR2508044B1 (ja) |
| GB (1) | GB2101135B (ja) |
| IT (1) | IT1171318B (ja) |
| NL (1) | NL8202473A (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1270996B (it) * | 1994-07-22 | 1997-05-26 | Wilton Licensing Ag | Derivati fosforilati di composti aventi attivita' antiinfiammatoria o analgesica e procedimento per la loro preparazione |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714226A (en) * | 1970-06-09 | 1973-01-30 | Merck & Co Inc | Phenyl benzoic acid compounds |
| DE2641526A1 (de) * | 1976-07-01 | 1978-01-12 | Uriach & Cia Sa J | 2-phosphonoxybenzoesaeure, deren salze, verfahren zu deren herstellung und pharmazeutische zusammensetzungen |
-
1981
- 1981-06-19 IT IT48719/81A patent/IT1171318B/it active
-
1982
- 1982-06-18 NL NL8202473A patent/NL8202473A/nl not_active Application Discontinuation
- 1982-06-18 GB GB08217710A patent/GB2101135B/en not_active Expired
- 1982-06-18 JP JP57105242A patent/JPS5843986A/ja active Pending
- 1982-06-18 DE DE19823223486 patent/DE3223486A1/de not_active Withdrawn
- 1982-06-18 FR FR828210635A patent/FR2508044B1/fr not_active Expired
- 1982-06-18 ES ES513246A patent/ES8307832A1/es not_active Expired
- 1982-06-18 BE BE0/208386A patent/BE893563A/fr not_active IP Right Cessation
- 1982-06-21 CA CA000405569A patent/CA1189527A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES513246A0 (es) | 1983-07-01 |
| IT1171318B (it) | 1987-06-10 |
| FR2508044A1 (fr) | 1982-12-24 |
| ES8307832A1 (es) | 1983-07-01 |
| FR2508044B1 (fr) | 1985-07-26 |
| GB2101135A (en) | 1983-01-12 |
| DE3223486A1 (de) | 1983-02-17 |
| NL8202473A (nl) | 1983-01-17 |
| JPS5843986A (ja) | 1983-03-14 |
| BE893563A (fr) | 1982-10-18 |
| GB2101135B (en) | 1984-10-24 |
| IT8148719A0 (it) | 1981-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |