FR2478092A1 - Nouveaux sels de l'acide 5-fluoro-2-methyl-1-(p-(methyl-sulfinyl)-benzylidene)-indene-3-acetique, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux sels de l'acide 5-fluoro-2-methyl-1-(p-(methyl-sulfinyl)-benzylidene)-indene-3-acetique, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2478092A1 FR2478092A1 FR8023162A FR8023162A FR2478092A1 FR 2478092 A1 FR2478092 A1 FR 2478092A1 FR 8023162 A FR8023162 A FR 8023162A FR 8023162 A FR8023162 A FR 8023162A FR 2478092 A1 FR2478092 A1 FR 2478092A1
- Authority
- FR
- France
- Prior art keywords
- salts
- methyl
- benzylidene
- fluoro
- base
- 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
- 230000000202 analgesic effect Effects 0.000 title claims abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 6
- 230000001754 anti-pyretic effect Effects 0.000 title claims abstract description 6
- 239000002221 antipyretic Substances 0.000 title claims abstract description 6
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical class CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 title abstract 3
- 239000004475 Arginine Substances 0.000 title 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 title 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 title 1
- 238000002347 injection Methods 0.000 title 1
- 239000007924 injection Substances 0.000 title 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 5
- 230000007935 neutral effect Effects 0.000 claims abstract description 5
- 150000007529 inorganic bases Chemical group 0.000 claims abstract description 3
- 150000007530 organic bases Chemical group 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 239000002904 solvent Substances 0.000 claims description 11
- -1 p- (methylsulfinyl) -benzylidene Chemical group 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 239000006196 drop Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- OSHVGUAPPIYWIS-UHFFFAOYSA-N piperazin-1-ium;acetate Chemical compound CC(O)=O.C1CNCCN1 OSHVGUAPPIYWIS-UHFFFAOYSA-N 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000006186 oral dosage form Substances 0.000 abstract 1
- 229960000894 sulindac Drugs 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 241001558496 Talpa caeca Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- MLKXDPUZXIRXEP-UHFFFAOYSA-N 2-[6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]-1-indenyl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2C1=CC1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT27822/79A IT1127274B (it) | 1979-12-04 | 1979-12-04 | Sali dell'acido 5-fluoro-2-metil-1-(p-(metilsulfinil)-benzilidene)-indene-3-acetico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2478092A1 true FR2478092A1 (fr) | 1981-09-18 |
| FR2478092B1 FR2478092B1 (enExample) | 1983-04-01 |
Family
ID=11222398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8023162A Granted FR2478092A1 (fr) | 1979-12-04 | 1980-10-29 | Nouveaux sels de l'acide 5-fluoro-2-methyl-1-(p-(methyl-sulfinyl)-benzylidene)-indene-3-acetique, leur procede de preparation et leur application en therapeutique |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS5692264A (enExample) |
| DE (1) | DE3040737A1 (enExample) |
| FR (1) | FR2478092A1 (enExample) |
| IT (1) | IT1127274B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2685916A1 (fr) * | 1992-01-04 | 1993-07-09 | Scras | Inhibiteurs mixtes de la no synthase et de la cyclooxygenase, ainsi qu'un procede pour leur preparation. |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0405602A1 (en) * | 1989-06-30 | 1991-01-02 | Laboratorios Vinas S.A. | New Zinc derivatives of anti-inflammatory drugs having improved therapeutic activity |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2164489A1 (en) * | 1970-04-07 | 1973-08-03 | Merck & Co Inc | 2-methyl-1-(para-methylsulphinylbenzylidene)inden - -3-yl-acetic acid esters - anti-inflammatories, antipyretics and anal |
-
1979
- 1979-12-04 IT IT27822/79A patent/IT1127274B/it active
-
1980
- 1980-10-29 FR FR8023162A patent/FR2478092A1/fr active Granted
- 1980-10-29 DE DE19803040737 patent/DE3040737A1/de not_active Ceased
- 1980-12-03 JP JP17144980A patent/JPS5692264A/ja active Pending
-
1982
- 1982-03-23 JP JP57047032A patent/JPS57167958A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2164489A1 (en) * | 1970-04-07 | 1973-08-03 | Merck & Co Inc | 2-methyl-1-(para-methylsulphinylbenzylidene)inden - -3-yl-acetic acid esters - anti-inflammatories, antipyretics and anal |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2685916A1 (fr) * | 1992-01-04 | 1993-07-09 | Scras | Inhibiteurs mixtes de la no synthase et de la cyclooxygenase, ainsi qu'un procede pour leur preparation. |
| FR2685869A1 (fr) * | 1992-01-04 | 1993-07-09 | Scras | Compositions therapeutiques a base d'inhibiteurs mixtes de la no synthase et de la cyclooxygenase. |
| GR1001443B (el) * | 1992-01-04 | 1993-12-30 | Sod Conseils Rech Applic | Μέ?οδος παρασκευής διπλών παρεμποδιστών ΝΟ συν?άσης και κυκλοοξυγενάσης. |
| BE1006227A3 (fr) * | 1992-01-04 | 1994-06-14 | Sod Conseils Rech Applic | Inhibiteurs mixtes de la no synthase et de la cyclooxygenase, un procede pour leur preparation et des compositions therapeutiques les contenant. |
| US5360925A (en) * | 1992-01-04 | 1994-11-01 | Societe De Conseils De Recherches Et D'applications Scientifiques | Dual inhibitors of no synthase and cyclooxygenase, process for their preparation and therapeutical compositions containing them |
| US5480999A (en) * | 1992-01-04 | 1996-01-02 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Dual inhibitors of NO synthase and cyclooxygenase, therapeutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3040737A1 (de) | 1981-08-27 |
| JPS57167958A (en) | 1982-10-16 |
| FR2478092B1 (enExample) | 1983-04-01 |
| IT1127274B (it) | 1986-05-21 |
| JPS5692264A (en) | 1981-07-25 |
| IT7927822A0 (it) | 1979-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |