FR2361390A1 - 2-2 thenyl-1,4,5 trimethyl-1,2,3,6-tetrahydropyridine a application therapeutique comme analgesique - Google Patents
2-2 thenyl-1,4,5 trimethyl-1,2,3,6-tetrahydropyridine a application therapeutique comme analgesiqueInfo
- Publication number
- FR2361390A1 FR2361390A1 FR7709585A FR7709585A FR2361390A1 FR 2361390 A1 FR2361390 A1 FR 2361390A1 FR 7709585 A FR7709585 A FR 7709585A FR 7709585 A FR7709585 A FR 7709585A FR 2361390 A1 FR2361390 A1 FR 2361390A1
- Authority
- FR
- France
- Prior art keywords
- thenyl
- trimethyl
- tetrahydropyridine
- analgesic
- therapeutic application
- 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.)
- Withdrawn
Links
- RRTRZWZVMHLHIF-UHFFFAOYSA-N 3,3,5-trimethyl-2,6-dihydro-1H-pyridine Chemical compound CC1(C=C(CNC1)C)C RRTRZWZVMHLHIF-UHFFFAOYSA-N 0.000 title 1
- 230000000202 analgesic effect Effects 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 2-thenyl Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 abstract 1
- XLNIRNAYIMZQLV-UHFFFAOYSA-N 4,5-dimethyl-2-thiophen-2-ylpyridine Chemical compound S1C(=CC=C1)C1=NC=C(C(=C1)C)C XLNIRNAYIMZQLV-UHFFFAOYSA-N 0.000 abstract 1
- SJSJDKXIYIGGOO-UHFFFAOYSA-N 4,5-dimethylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C=C1C SJSJDKXIYIGGOO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16C—SHAFTS; FLEXIBLE SHAFTS; ELEMENTS OR CRANKSHAFT MECHANISMS; ROTARY BODIES OTHER THAN GEARING ELEMENTS; BEARINGS
- F16C2300/00—Application independent of particular apparatuses
- F16C2300/10—Application independent of particular apparatuses related to size
- F16C2300/14—Large applications, e.g. bearings having an inner diameter exceeding 500 mm
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
2-(2-thényl)1,4,5-triméthyl-1,2,3,6-tétrahydropyndine et son procédé de préparation. On fait réagir du 2-cyano-4,5-diméthylpyridine avec une solution éthérée de thiényllithium, et par hydrolyse acide on obtient la 2-thiényl-(4,5-diméthyl-2-pyridino)cétone; par chauffage en présence d'hydrate d'hydrazine en milieu basique on obtient une 2-(2-thiényl)-4,5-diméthylpyridine qui par chauffage en présence d'ioduré de méthyle donne un produit intermédiaire que l'on purifie avec du NaBH4 dans l'éthanol pour obtenir une 2-(2-thényl)-1,4,5-triméthyl)1,2,3,6-tétrahydropyridine. Applications pharmaceutiques comme analgésiques.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES441097A ES441097A1 (es) | 1975-09-19 | 1975-09-19 | Procedimiento para la obtencion de 2,4, 5-trimetil-tieno (3,2-f) morfano. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2361390A1 true FR2361390A1 (fr) | 1978-03-10 |
Family
ID=8470007
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7627080A Withdrawn FR2362128A1 (fr) | 1975-09-19 | 1976-09-09 | 2-cyano-4,5-dimethyl-pyridine, et procede de preparation |
| FR7709585A Withdrawn FR2361390A1 (fr) | 1975-09-19 | 1977-03-30 | 2-2 thenyl-1,4,5 trimethyl-1,2,3,6-tetrahydropyridine a application therapeutique comme analgesique |
| FR7709584A Withdrawn FR2361389A1 (fr) | 1975-09-19 | 1977-03-30 | 2-(2-thenyl)-4,5-dimethylpyridine a application therapeutique comme analgesique |
| FR7709583A Withdrawn FR2361388A1 (fr) | 1975-09-19 | 1977-03-30 | 2-thienyl-(4,5-dimethyl-2-pyridyl)-cetone a application therapeutique comme analgesique |
| FR7709582A Withdrawn FR2361397A1 (fr) | 1975-09-19 | 1977-03-30 | 2,4,5 trimethyl-thieno(3,2-f)morphane, procede de preparation et application pharmacologique |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7627080A Withdrawn FR2362128A1 (fr) | 1975-09-19 | 1976-09-09 | 2-cyano-4,5-dimethyl-pyridine, et procede de preparation |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7709584A Withdrawn FR2361389A1 (fr) | 1975-09-19 | 1977-03-30 | 2-(2-thenyl)-4,5-dimethylpyridine a application therapeutique comme analgesique |
| FR7709583A Withdrawn FR2361388A1 (fr) | 1975-09-19 | 1977-03-30 | 2-thienyl-(4,5-dimethyl-2-pyridyl)-cetone a application therapeutique comme analgesique |
| FR7709582A Withdrawn FR2361397A1 (fr) | 1975-09-19 | 1977-03-30 | 2,4,5 trimethyl-thieno(3,2-f)morphane, procede de preparation et application pharmacologique |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5248694A (fr) |
| AR (1) | AR210612A1 (fr) |
| AT (1) | AT347051B (fr) |
| BE (1) | BE845755A (fr) |
| CA (1) | CA1068279A (fr) |
| CH (1) | CH617195A5 (fr) |
| DE (1) | DE2639181C3 (fr) |
| ES (1) | ES441097A1 (fr) |
| FR (5) | FR2362128A1 (fr) |
| GB (1) | GB1513980A (fr) |
| NL (1) | NL7610437A (fr) |
| NZ (1) | NZ181870A (fr) |
| PT (1) | PT65547B (fr) |
| SE (2) | SE7609357L (fr) |
| SU (3) | SU620210A3 (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1274913A (fr) * | 1959-09-09 | 1961-11-03 | Rohm & Haas | Procédé de cyanuration de composés nu-hétérocycliques et nitriles ainsi obtenus |
-
1975
- 1975-09-19 ES ES441097A patent/ES441097A1/es not_active Expired
-
1976
- 1976-08-24 SE SE7609357A patent/SE7609357L/xx not_active Application Discontinuation
- 1976-08-25 GB GB35397/76A patent/GB1513980A/en not_active Expired
- 1976-08-26 NZ NZ181870A patent/NZ181870A/xx unknown
- 1976-08-26 AR AR264463A patent/AR210612A1/es active
- 1976-08-31 DE DE2639181A patent/DE2639181C3/de not_active Expired
- 1976-09-01 BE BE170277A patent/BE845755A/fr unknown
- 1976-09-02 PT PT65547A patent/PT65547B/pt unknown
- 1976-09-09 FR FR7627080A patent/FR2362128A1/fr not_active Withdrawn
- 1976-09-16 AT AT687976A patent/AT347051B/de not_active IP Right Cessation
- 1976-09-17 SU SU762401851A patent/SU620210A3/ru active
- 1976-09-17 CH CH1182776A patent/CH617195A5/fr not_active IP Right Cessation
- 1976-09-17 JP JP51110886A patent/JPS5248694A/ja active Pending
- 1976-09-20 CA CA261,567A patent/CA1068279A/fr not_active Expired
- 1976-09-20 NL NL7610437A patent/NL7610437A/xx not_active Application Discontinuation
-
1977
- 1977-02-21 SU SU772453400A patent/SU650506A3/ru active
- 1977-02-21 SU SU772455453A patent/SU671731A3/ru active
- 1977-03-30 FR FR7709585A patent/FR2361390A1/fr not_active Withdrawn
- 1977-03-30 FR FR7709584A patent/FR2361389A1/fr not_active Withdrawn
- 1977-03-30 FR FR7709583A patent/FR2361388A1/fr not_active Withdrawn
- 1977-03-30 FR FR7709582A patent/FR2361397A1/fr not_active Withdrawn
-
1979
- 1979-08-27 SE SE7907106A patent/SE7907106L/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2361397A1 (fr) | 1978-03-10 |
| DE2639181C3 (de) | 1979-05-31 |
| SU620210A3 (ru) | 1978-08-15 |
| SE7907106L (sv) | 1979-08-27 |
| GB1513980A (en) | 1978-06-14 |
| JPS5248694A (en) | 1977-04-18 |
| DE2639181B2 (de) | 1978-10-05 |
| FR2362128A1 (fr) | 1978-03-17 |
| ES441097A1 (es) | 1977-03-16 |
| FR2361389A1 (fr) | 1978-03-10 |
| FR2361388A1 (fr) | 1978-03-10 |
| AR210612A1 (es) | 1977-08-31 |
| SU671731A3 (ru) | 1979-06-30 |
| CH617195A5 (en) | 1980-05-14 |
| AT347051B (de) | 1978-12-11 |
| BE845755A (fr) | 1977-03-01 |
| NZ181870A (en) | 1978-11-13 |
| SE7609357L (sv) | 1977-03-20 |
| AU1715576A (en) | 1978-03-02 |
| PT65547B (en) | 1978-03-24 |
| CA1068279A (fr) | 1979-12-18 |
| PT65547A (en) | 1976-10-01 |
| NL7610437A (nl) | 1977-03-22 |
| SU650506A3 (ru) | 1979-02-28 |
| ATA687976A (de) | 1978-04-15 |
| DE2639181A1 (de) | 1977-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |