FR2475539A1 - Esters d'acides arylpropioniques, leur procede de preparation et leur application en therapeutique - Google Patents
Esters d'acides arylpropioniques, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2475539A1 FR2475539A1 FR8102713A FR8102713A FR2475539A1 FR 2475539 A1 FR2475539 A1 FR 2475539A1 FR 8102713 A FR8102713 A FR 8102713A FR 8102713 A FR8102713 A FR 8102713A FR 2475539 A1 FR2475539 A1 FR 2475539A1
- Authority
- FR
- France
- Prior art keywords
- monoester
- phenyl
- radical
- glycol
- propionic acid
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 14
- 150000002148 esters Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 8
- 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 compound C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 1-oxo-2-isoindolinyl Chemical group 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical group 0.000 claims description 3
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- 235000019260 propionic acid Nutrition 0.000 claims 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 2
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003254 radicals Chemical group 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical group COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 229960001680 ibuprofen Drugs 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 8
- 235000010418 carrageenan Nutrition 0.000 description 7
- 229920001525 carrageenan Polymers 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000036461 convulsion Effects 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000036470 plasma concentration Effects 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
- 241000238876 Acari Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 238000003556 assay Methods 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
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000010828 elution 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
- 238000013213 extrapolation Methods 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000000544 hyperemic effect Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 108091050528 miR-653 stem-loop Proteins 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Indole Compounds (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 |
|---|---|
| FR2475539A1 true FR2475539A1 (fr) | 1981-08-14 |
| FR2475539B1 FR2475539B1 (Direct) | 1984-05-25 |
Family
ID=11162015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8102713A Granted FR2475539A1 (fr) | 1980-02-13 | 1981-02-11 | Esters d'acides arylpropioniques, leur procede de preparation et leur application en therapeutique |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4379091A (Direct) |
| JP (1) | JPS56128731A (Direct) |
| AR (1) | AR228590A1 (Direct) |
| AU (1) | AU529728B2 (Direct) |
| BE (1) | BE887460A (Direct) |
| DE (1) | DE3104789C2 (Direct) |
| ES (1) | ES499360A0 (Direct) |
| FR (1) | FR2475539A1 (Direct) |
| GB (1) | GB2068954B (Direct) |
| IT (1) | IT1147309B (Direct) |
| NL (1) | NL8100712A (Direct) |
| PH (1) | PH17112A (Direct) |
| PT (1) | PT72497B (Direct) |
| ZA (1) | ZA81904B (Direct) |
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
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 |
| AR228590A1 (es) | 1983-03-30 |
| AU529728B2 (en) | 1983-06-16 |
| DE3104789C2 (de) | 1983-05-11 |
| 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 (Direct) | 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 |
|---|---|---|---|
| ST | Notification of lapse |