DE3040737A1 - Salze der 5-fluor-2-methyl-1(p-(methylsulfinyl)-benzyliden)-inden-3-essigsaeure, vefahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen - Google Patents
Salze der 5-fluor-2-methyl-1(p-(methylsulfinyl)-benzyliden)-inden-3-essigsaeure, vefahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungenInfo
- Publication number
- DE3040737A1 DE3040737A1 DE19803040737 DE3040737A DE3040737A1 DE 3040737 A1 DE3040737 A1 DE 3040737A1 DE 19803040737 DE19803040737 DE 19803040737 DE 3040737 A DE3040737 A DE 3040737A DE 3040737 A1 DE3040737 A1 DE 3040737A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- methylsulfinyl
- benzylidene
- fluoro
- indene
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 17
- -1 p- (methylsulfinyl) -benzylidene Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 230000001754 anti-pyretic effect Effects 0.000 claims description 5
- 239000002221 antipyretic Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 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
- 239000007788 liquid Substances 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
- 239000008298 dragée Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- MKYNHKOAYQRSBD-UHFFFAOYSA-N dioxouranium;nitric acid Chemical compound O=[U]=O.O[N+]([O-])=O.O[N+]([O-])=O MKYNHKOAYQRSBD-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JMNVALXGIOSFGW-UHFFFAOYSA-N 2-(3h-inden-1-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CCC2=C1 JMNVALXGIOSFGW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- JAUUPKPADFYNKU-UHFFFAOYSA-N 2-(3H-inden-1-yl)-3-(4-methylsulfinylphenyl)prop-2-enoic acid Chemical compound C1=CC(S(=O)C)=CC=C1C=C(C(O)=O)C1=CCC2=CC=CC=C12 JAUUPKPADFYNKU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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 (1)
| Publication Number | Publication Date |
|---|---|
| DE3040737A1 true DE3040737A1 (de) | 1981-08-27 |
Family
ID=11222398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803040737 Ceased DE3040737A1 (de) | 1979-12-04 | 1980-10-29 | Salze der 5-fluor-2-methyl-1(p-(methylsulfinyl)-benzyliden)-inden-3-essigsaeure, vefahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen |
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 |
|---|---|---|---|---|
| EP0405602A1 (en) * | 1989-06-30 | 1991-01-02 | Laboratorios Vinas S.A. | New Zinc derivatives of anti-inflammatory drugs having improved therapeutic activity |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9200114D0 (en) * | 1992-01-04 | 1992-02-26 | Scras | Dual inhibitors of no synthase and cyclooxygenase |
Family Cites Families (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
Cited By (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 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2478092A1 (fr) | 1981-09-18 |
| 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 |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8131 | Rejection |