FR2483923A1 - 6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique - Google Patents
6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique Download PDFInfo
- Publication number
- FR2483923A1 FR2483923A1 FR8012553A FR8012553A FR2483923A1 FR 2483923 A1 FR2483923 A1 FR 2483923A1 FR 8012553 A FR8012553 A FR 8012553A FR 8012553 A FR8012553 A FR 8012553A FR 2483923 A1 FR2483923 A1 FR 2483923A1
- Authority
- FR
- France
- Prior art keywords
- methyl
- pyridine
- furo
- compound according
- compound
- 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
- AZFBLAIWASUAIF-UHFFFAOYSA-N 6-methyl-4-piperazin-1-ylfuro[3,2-c]pyridine Chemical compound N=1C(C)=CC=2OC=CC=2C=1N1CCNCC1 AZFBLAIWASUAIF-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- WKGSLYHMRQRARV-UHFFFAOYSA-N 4-hydroxy-6-methyl-1h-pyridin-2-one Chemical compound CC1=CC(=O)C=C(O)N1 WKGSLYHMRQRARV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000935 antidepressant agent Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000008485 antagonism Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 206010015995 Eyelid ptosis Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 230000003470 muricidal effect Effects 0.000 description 3
- 201000003004 ptosis Diseases 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- -1 1-piperazinyl Chemical group 0.000 description 2
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- FNPYPLBPZILBRT-UHFFFAOYSA-N 3h-furo[3,2-b]pyridin-2-one Chemical compound C1=CC=C2OC(=O)CC2=N1 FNPYPLBPZILBRT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010042008 Stereotypy Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011670 long-evans rat Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003773 muricide Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical compound C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 description 1
- 229950002315 quipazine Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8012553A FR2483923A1 (fr) | 1980-06-05 | 1980-06-05 | 6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique |
| PCT/EP1981/000060 WO1981003493A1 (en) | 1980-06-05 | 1981-05-29 | 4-(1-piperazinyl)-furo(3,2c)pyridine derivatives,processes for their preparation and pharmaceutical compositions containing same |
| JP56501840A JPS57500876A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-06-05 | 1981-05-29 | |
| FI813293A FI813293A7 (fi) | 1980-06-05 | 1981-05-29 | 4-(1-piperatsinyyli)furo/3,2- c/pyridiinijohdannaisia, menetelmä niide n valmistamiseksi ja niitä sissisältäviä farmaseuttisia koostumuksia. |
| AU72273/81A AU7227381A (en) | 1980-06-05 | 1981-05-29 | 4-(1-piperazinyl)-furo(3,2-c) pyridine derivatives, processes for their preparation and pharmaceutical compositions containing same |
| PT73123A PT73123B (en) | 1980-06-05 | 1981-06-02 | 4-(1-piperazinyl)-furo<3,2-c>pyridine derivatives processes for their preparation and pharmaceutical compositions containing same |
| ZA00813678A ZA813678B (en) | 1980-06-05 | 1981-06-02 | 4-(-1-piperazinyl)-furo (3,2-c)pyridine derivatives,processes for their preparation and pharmaceutical compositions containing same |
| GR65138A GR75664B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-06-05 | 1981-06-03 | |
| EP81400889A EP0041891A1 (fr) | 1980-06-05 | 1981-06-04 | 4-(1-pipérazinyl)-furo (3,2-c) pyridines substituées, leurs procédés d'obtention et leur application en thérapeutique |
| ES502824A ES8203380A1 (es) | 1980-06-05 | 1981-06-05 | Un procedimiento de preparacion de 4-(1-piperazinil)-fu- ro(3,2-c)piridinas |
| DK498681A DK498681A (da) | 1980-06-05 | 1981-11-11 | 4-(1-piperazinyl)-furo (3,2-c) pyridinderivater fremgangsmaader til deres fremstilling og farmaceutiske midler indeholdende disse |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8012553A FR2483923A1 (fr) | 1980-06-05 | 1980-06-05 | 6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2483923A1 true FR2483923A1 (fr) | 1981-12-11 |
| FR2483923B1 FR2483923B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-05-27 |
Family
ID=9242757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8012553A Granted FR2483923A1 (fr) | 1980-06-05 | 1980-06-05 | 6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique |
Country Status (9)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4831031A (en) * | 1988-01-22 | 1989-05-16 | Pfizer Inc. | Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity |
| JP4559749B2 (ja) * | 2004-02-16 | 2010-10-13 | あすか製薬株式会社 | ピペラジニルピリジン誘導体 |
| JP4596792B2 (ja) * | 2004-02-24 | 2010-12-15 | あすか製薬株式会社 | ５−ｈｔ１ａ作動作用と５−ｈｔ３拮抗作用を併有する薬剤 |
-
1980
- 1980-06-05 FR FR8012553A patent/FR2483923A1/fr active Granted
-
1981
- 1981-05-29 JP JP56501840A patent/JPS57500876A/ja active Pending
- 1981-05-29 WO PCT/EP1981/000060 patent/WO1981003493A1/de active Application Filing
- 1981-06-02 ZA ZA00813678A patent/ZA813678B/xx unknown
- 1981-06-02 PT PT73123A patent/PT73123B/pt unknown
- 1981-06-03 GR GR65138A patent/GR75664B/el unknown
- 1981-06-04 EP EP81400889A patent/EP0041891A1/fr not_active Withdrawn
- 1981-06-05 ES ES502824A patent/ES8203380A1/es not_active Expired
- 1981-11-11 DK DK498681A patent/DK498681A/da not_active Application Discontinuation
Non-Patent Citations (2)
| Title |
|---|
| EXBK/71 * |
| EXBK/73 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES502824A0 (es) | 1982-04-01 |
| EP0041891A1 (fr) | 1981-12-16 |
| ZA813678B (en) | 1982-06-30 |
| ES8203380A1 (es) | 1982-04-01 |
| WO1981003493A1 (en) | 1981-12-10 |
| GR75664B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-02 |
| JPS57500876A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-05-20 |
| PT73123B (en) | 1982-07-15 |
| DK498681A (da) | 1981-12-10 |
| PT73123A (en) | 1981-07-01 |
| FR2483923B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1103676A (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et leurs sels | |
| EP0080934A1 (fr) | Acides (oxo-4-4H-(1)-benzopyran-8-yl) alcanoiques, sels et dérivés, préparation et médicaments les contenant | |
| FR2460919A1 (fr) | Amino-ethers oxydes, leur procede de preparation et leur application en therapeutique | |
| FR2554719A1 (fr) | Medicaments a base de nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine | |
| CA1097647A (fr) | Procede de preparation de nouvelles imidazoquinoleines et de leurs sels | |
| EP0024960B1 (fr) | Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux | |
| CA1121353A (fr) | Procede de preparation de nouvelles imidazoquinoxalines et de leurs sels | |
| EP0239461A1 (fr) | Dérivés de N-¬¬(hydroxy-2 phényl) (phényl) méthylène amino-2 éthyl acétamide, leur préparation et leur application en thérapeutique | |
| EP0239436B1 (fr) | Nouveau dérivé tricyclique dénommé acide (chloro-3 méthyl-6 dioxo-5,5 dihydro-6, 11 dibenzo (c,f) thiazépine (1,2) yl-11 amino) -5 pentanoique, son procédé de préparation et les compositions pharmaceutiques qui le contiennent | |
| EP0173597B1 (fr) | Nouveaux éther-oxydes dérivés de cyclopropylphénols | |
| EP0006789A1 (fr) | Composés bis (aryloxyalcanecarboxyliques), leur préparation et leur utilisation en thérapeutique | |
| FR2483923A1 (fr) | 6-methyl-4-(1-piperazinyl)-furo (3,2-c) pyridine, son procede d'obtention et son application en therapeutique | |
| CA1133904A (fr) | Procedes de preparation de nouveaux derives de la piperidylbenzimidazolinone | |
| LU84841A1 (fr) | Nouveaux derives de l'acide 4-hydrox 3-quinoleine carboxyclique substitues en 2,leur preparation,leur application comme medicaments,les compositions les renfermant et les intermediaires obtenus | |
| FR2600647A1 (fr) | Derives de la glycine | |
| EP0117171B1 (fr) | Dérivés aminés de la pyridazine substitués en position 6 par un hétérocycle ou un alicycle, procédé d'obtention et médicaments les contenant | |
| CH449652A (fr) | Procédé de préparation de nouvelles hydroxydiamines | |
| EP0196943B1 (fr) | Nouveaux dérivés 8-thiotétrahydroquinoléines et leurs sels | |
| FR2467203A1 (fr) | Derives de 1,2,4-oxadiazolin-5-one, procede pour leur preparation et compositions pharmaceutiques les contenant | |
| EP0079810A1 (fr) | Nouveaux dérivés de la phényl-4 quinazoline actifs sur le système nerveux central | |
| CA1098524A (fr) | Procede de preparation de nouveaux derives de l'acide piperazinecarbodithioique | |
| EP0005091B1 (fr) | Nouvelles pipérazines monosubstituées, leurs procédés de préparation et les compositions pharmaceutiques les renfermant | |
| EP1242381A2 (fr) | Derives de 2-phenyl-quinoleine et leur utilisation en tant qu'agent contractant des muscles lisses | |
| EP0038731A2 (fr) | Dérivés de thiazole, leur préparation et leur application en thérapeutique | |
| EP0169186B1 (fr) | Nouveaux dérivés de décahydroquinoléinol, leur procédé de préparation et les compositions les contenant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |