WO1981003493A1 - 4-(1-piperazinyl)-furo(3,2c)pyridine derivatives,processes for their preparation and pharmaceutical compositions containing same - Google Patents
4-(1-piperazinyl)-furo(3,2c)pyridine derivatives,processes for their preparation and pharmaceutical compositions containing same Download PDFInfo
- Publication number
- WO1981003493A1 WO1981003493A1 PCT/EP1981/000060 EP8100060W WO8103493A1 WO 1981003493 A1 WO1981003493 A1 WO 1981003493A1 EP 8100060 W EP8100060 W EP 8100060W WO 8103493 A1 WO8103493 A1 WO 8103493A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- furo
- piperazinyl
- formula
- preparation
- processes
- Prior art date
Links
- LUIZVTKJWSGSPA-UHFFFAOYSA-N 4-piperazin-1-ylfuro[3,2-c]pyridine Chemical class C1CNCCN1C1=NC=CC2=C1C=CO2 LUIZVTKJWSGSPA-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 230000001430 anti-depressive effect Effects 0.000 claims abstract description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000001003 psychopharmacologic effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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 3
- 229960003147 reserpine Drugs 0.000 description 3
- 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 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-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
- 239000002585 base Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000003470 muricidal effect Effects 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical compound C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 description 2
- 229950002315 quipazine Drugs 0.000 description 2
- 239000007858 starting material Substances 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 1
- ZEZJPIDPVXJEME-UHFFFAOYSA-N 2,4-Dihydroxypyridine Chemical class OC=1C=CNC(=O)C=1 ZEZJPIDPVXJEME-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- 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
- XMXQLSCBPQZGAD-UHFFFAOYSA-N 4-chloro-6-methylfuro[3,2-c]pyridine Chemical class ClC1=NC(C)=CC2=C1C=CO2 XMXQLSCBPQZGAD-UHFFFAOYSA-N 0.000 description 1
- OPFFYLJLHPZSEO-UHFFFAOYSA-N 4-chlorofuro[3,2-c]pyridine Chemical compound ClC1=NC=CC2=C1C=CO2 OPFFYLJLHPZSEO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AZFBLAIWASUAIF-UHFFFAOYSA-N 6-methyl-4-piperazin-1-ylfuro[3,2-c]pyridine Chemical class N=1C(C)=CC=2OC=CC=2C=1N1CCNCC1 AZFBLAIWASUAIF-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 206010042008 Stereotypy Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000013289 male long evans rat Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003773 muricide Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000002627 tracheal intubation 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
Definitions
- the present invention relates to new 4- (1-piperazinyl) -furo [3,2-c] pyridine derivatives, to processes for their preparation and to pharmaceutical compositions containing same in the form of the free base or a pharmaceutically acceptable salt.
- R represents hydrogen or a lower alkyl (1-6 C) group.
- the compounds of formula I can be obtained by. condensation of piperazines with a 4-halo-furo [3,2-c] pyridine derivative (formula II).
- the latter starting compound can, for example, be prepared starting from a 4-hydroxy-2-oxo-1,2-dihydro-pyridine derivative according to the following reaction steps:
- the condensation of a compound II with piperazine is carried out using piperazine in excess, preferably by refluxing the mixture in a suitable solvent, such as ethylene glycol monomethyl ether.
- a salt of the compounds of formula I is obtained by reaction of the free base with an organic or inorganic acid, such as HCl, HBr, H 3 PO 4 , acetic acid, maleic acid, fumaric acid, tartaric acid, etc.
- organic or inorganic acid such as HCl, HBr, H 3 PO 4 , acetic acid, maleic acid, fumaric acid, tartaric acid, etc.
- the compounds of the invention and the pharmaceutically acceptable salts thereof have potent psychopharmacological activities and particularly an anti-depressive activity.
- the compounds of formula I, associated with the usual pharmaceutical carriers, can be administered enterally or parenterally, preferably in a daily dosage of from 0.1-50 mg / kg bodyweight, and more particularly from 1-10 mg / kg bodyweight.
- the preferred daily dosage ranks for use in human is from about 50-100 mg.
- psycopharmacological activity and especially the anti-depressive activity of compounds of formula I are illustrated by the following test results.
- a - Antaqonism to reserpine ptosis in mice The product under study (or the vehicle alone - gum arabic and water 1/1 - for the control group) is administered by oesophageal Intubation to male mice of OF1 IFFA CREDO stock of mean weight 22 ⁇ 1 g, and then, 60 min. after treatment, all animals receive intraperitoneally 1 mg / kg -1 of reserpine base.
- the compound I, in which R is CH 3 , and the reference compound quipazine are administered in a dose of 40 mg / kg and the compound I, in which R is hydrogen, in a dose of 10 mg / kg.
- the compound obtained is converted into the maleattee salt; mp 295 ° C. (This salt further contained 1/4 H 2 O per mol.).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| FI813293A FI813293L (fi) | 1980-06-05 | 1981-05-29 | 4-(1-piperazinyl)-furo/3,2-c/pyridinderivat foerfarande foer framstaellning av dem och dessa innehaollande farmaceutiska kompositioner |
| 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8012553 | 1980-06-05 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| WO1981003493A1 true WO1981003493A1 (en) | 1981-12-10 |
Family
ID=9242757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (9)
Cited By (1)
| 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 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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/ES502824A0/es active Granted
- 1981-11-11 DK DK498681A patent/DK498681A/da not_active Application Discontinuation
Non-Patent Citations (2)
| Title |
|---|
| Bulletin de la Societe Chimique de France, no. 5, May 1971 (Paris, FR) E. Bisagni: "Furannes et pyrroles disubstitués en 2,3 X. Synthèse de furo [3,2-c] pyridines à partir du formyl-2 carbéthoxy-3 furanne", pages 1727-30 * |
| Chimie Therapeutique, volume VIII, no. 5, issued September - October 1973, (Chantenay-Malabry, FR) E. Bisagni: "Aza-indoles-II. Nouveaux dérivés aza-5 indoliques et leurs propriétés pharmacologiques", pages 559-566 * |
Cited By (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK498681A (da) | 1981-12-10 |
| GR75664B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-02 |
| EP0041891A1 (fr) | 1981-12-16 |
| ZA813678B (en) | 1982-06-30 |
| FR2483923B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-05-27 |
| PT73123B (en) | 1982-07-15 |
| ES8203380A1 (es) | 1982-04-01 |
| PT73123A (en) | 1981-07-01 |
| JPS57500876A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-05-20 |
| FR2483923A1 (fr) | 1981-12-11 |
| ES502824A0 (es) | 1982-04-01 |
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