DE3104789C2 - Arylpropionsäureester, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate - Google Patents
Arylpropionsäureester, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische PräparateInfo
- Publication number
- DE3104789C2 DE3104789C2 DE3104789A DE3104789A DE3104789C2 DE 3104789 C2 DE3104789 C2 DE 3104789C2 DE 3104789 A DE3104789 A DE 3104789A DE 3104789 A DE3104789 A DE 3104789A DE 3104789 C2 DE3104789 C2 DE 3104789C2
- Authority
- DE
- Germany
- Prior art keywords
- ibuprofen
- preparation
- processes
- pharmaceutical preparations
- acids
- 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
- 150000002148 esters Chemical class 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title description 6
- 238000000034 method Methods 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- -1 aryl propionic acid ester Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 abstract description 11
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 abstract description 8
- 150000007513 acids Chemical class 0.000 abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 abstract description 6
- 230000002496 gastric effect Effects 0.000 abstract description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 29
- 229960001680 ibuprofen Drugs 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 239000000679 carrageenan Substances 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 229940113118 carrageenan Drugs 0.000 description 6
- 238000007912 intraperitoneal administration Methods 0.000 description 6
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
- 229960004373 acetylcholine Drugs 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- TUZRJGVLAFMQEK-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1.CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 TUZRJGVLAFMQEK-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010000059 abdominal discomfort Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000000544 hyperemic effect Effects 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19879/80A IT1147309B (it) | 1980-02-13 | 1980-02-13 | Esteri di acidi arilpropionici ad attivita' antiinfiammatoria,processo per la loro preparazione,e composizioni farmaceutiche relative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3104789A1 DE3104789A1 (de) | 1981-12-17 |
| DE3104789C2 true DE3104789C2 (de) | 1983-05-11 |
Family
ID=11162015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3104789A Expired DE3104789C2 (de) | 1980-02-13 | 1981-02-11 | Arylpropionsäureester, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4379091A (esLanguage) |
| JP (1) | JPS56128731A (esLanguage) |
| AR (1) | AR228590A1 (esLanguage) |
| AU (1) | AU529728B2 (esLanguage) |
| BE (1) | BE887460A (esLanguage) |
| DE (1) | DE3104789C2 (esLanguage) |
| ES (1) | ES499360A0 (esLanguage) |
| FR (1) | FR2475539A1 (esLanguage) |
| GB (1) | GB2068954B (esLanguage) |
| IT (1) | IT1147309B (esLanguage) |
| NL (1) | NL8100712A (esLanguage) |
| PH (1) | PH17112A (esLanguage) |
| PT (1) | PT72497B (esLanguage) |
| ZA (1) | ZA81904B (esLanguage) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2551973Y2 (ja) * | 1991-07-19 | 1997-10-27 | 三菱自動車工業株式会社 | 自動車の開閉部材施錠装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468760A1 (de) * | 1963-05-02 | 1969-01-09 | Parke Davis & Co | Verfahren zur Herstellung von 4- und 5-Aryl-1-naphthalinessigsaeuren und deren Derivaten |
| US4009197A (en) * | 1967-01-13 | 1977-02-22 | Syntex Corporation | 2-(6-Substituted-2'-naphthyl) acetic acid derivatives and the salts and esters thereof |
-
1980
- 1980-02-13 IT IT19879/80A patent/IT1147309B/it active
-
1981
- 1981-01-12 PT PT72497A patent/PT72497B/pt unknown
- 1981-02-06 AU AU66991/81A patent/AU529728B2/en not_active Ceased
- 1981-02-06 GB GB8103733A patent/GB2068954B/en not_active Expired
- 1981-02-09 AR AR284244A patent/AR228590A1/es active
- 1981-02-10 JP JP1889981A patent/JPS56128731A/ja active Pending
- 1981-02-10 PH PH25207A patent/PH17112A/en unknown
- 1981-02-11 ZA ZA00810904A patent/ZA81904B/xx unknown
- 1981-02-11 US US06/233,665 patent/US4379091A/en not_active Expired - Fee Related
- 1981-02-11 BE BE2/59006A patent/BE887460A/nl not_active IP Right Cessation
- 1981-02-11 FR FR8102713A patent/FR2475539A1/fr active Granted
- 1981-02-11 DE DE3104789A patent/DE3104789C2/de not_active Expired
- 1981-02-12 ES ES499360A patent/ES499360A0/es active Granted
- 1981-02-13 NL NL8100712A patent/NL8100712A/nl not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| BE887460A (nl) | 1981-06-01 |
| DE3104789A1 (de) | 1981-12-17 |
| ZA81904B (en) | 1982-02-24 |
| IT8019879A0 (it) | 1980-02-13 |
| FR2475539A1 (fr) | 1981-08-14 |
| AR228590A1 (es) | 1983-03-30 |
| AU529728B2 (en) | 1983-06-16 |
| AU6699181A (en) | 1981-08-20 |
| PT72497A (en) | 1981-02-01 |
| NL8100712A (nl) | 1981-09-16 |
| ES8202326A1 (es) | 1982-02-01 |
| JPS56128731A (en) | 1981-10-08 |
| ES499360A0 (es) | 1982-02-01 |
| FR2475539B1 (esLanguage) | 1984-05-25 |
| GB2068954A (en) | 1981-08-19 |
| PT72497B (en) | 1982-02-05 |
| US4379091A (en) | 1983-04-05 |
| PH17112A (en) | 1984-06-01 |
| GB2068954B (en) | 1983-08-10 |
| IT1147309B (it) | 1986-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |