FI58124C - Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan - Google Patents
Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan Download PDFInfo
- Publication number
- FI58124C FI58124C FI763614A FI763614A FI58124C FI 58124 C FI58124 C FI 58124C FI 763614 A FI763614 A FI 763614A FI 763614 A FI763614 A FI 763614A FI 58124 C FI58124 C FI 58124C
- Authority
- FI
- Finland
- Prior art keywords
- furoyl
- dimetoxy
- quinazoline
- piperazinyl
- dimethoxy
- Prior art date
Links
- -1 2-FUROYL Chemical class 0.000 title description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229960001289 prazosin Drugs 0.000 description 7
- BJAYMNUBIULRMF-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N)=C(C#N)C=C1OC BJAYMNUBIULRMF-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- SADPINFEWFPMEA-UHFFFAOYSA-N furan-2-yl(piperazin-1-yl)methanone Chemical compound C=1C=COC=1C(=O)N1CCNCC1 SADPINFEWFPMEA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- AFGXCIJBGLMDKI-UHFFFAOYSA-N 2-isothiocyanato-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N=C=S)=C(C#N)C=C1OC AFGXCIJBGLMDKI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MITDXNUXOAYFGC-UHFFFAOYSA-N 1-prop-2-ynylbenzimidazole Chemical compound C1=CC=C2N(CC#C)C=NC2=C1 MITDXNUXOAYFGC-UHFFFAOYSA-N 0.000 description 1
- SEUMXCKRKZIQAB-UHFFFAOYSA-N 4-(furan-2-carbonyl)piperazine-1-carbothioyl chloride Chemical compound C1CN(C(=S)Cl)CCN1C(=O)C1=CC=CO1 SEUMXCKRKZIQAB-UHFFFAOYSA-N 0.000 description 1
- RMNBSOZAKBNEIH-UHFFFAOYSA-N CON1CN=C2C=CC(=CC2=C1OC)N1CCN(CC1)C(=O)C=1OC=CC1 Chemical compound CON1CN=C2C=CC(=CC2=C1OC)N1CCN(CC1)C(=O)C=1OC=CC1 RMNBSOZAKBNEIH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MXWBCRALMDQINL-UHFFFAOYSA-N n-(2-cyano-4,5-dimethoxyphenyl)-4-(furan-2-carbonyl)-n-methylpiperazine-1-carbothioamide Chemical compound C1=C(OC)C(OC)=CC(C#N)=C1N(C)C(=S)N1CCN(C(=O)C=2OC=CC=2)CC1 MXWBCRALMDQINL-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI763614A FI58124C (fi) | 1976-12-15 | 1976-12-15 | Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan |
| CH1438277A CH630624A5 (en) | 1976-12-15 | 1977-11-24 | Processes for preparing 3,4-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinylthiocarbamido)benzo nitrile. |
| SE7713377A SE424993B (sv) | 1976-12-15 | 1977-11-25 | Mellanprodukt for framstellning av 6,7-dimetoxi-4-amino-2-/4-(2-furoyl)-1-piperazinyl/kinazolin med blodtryckssenkande verkan |
| AT867177A AT358047B (de) | 1976-12-15 | 1977-12-05 | Verfahren zur herstellung des neuen 3,4- -dimethoxy-6-(4-(2-furoyl)-1-piperazinylthio- carbamido)-benzonitril |
| ZA00777222A ZA777222B (en) | 1976-12-15 | 1977-12-05 | An intermediate product for the production of 6,7-dimethoxy-4-amino-2-(4-(furoyl)-1-piperazinyl)quinazoline having an antihypertensive effect |
| NL7713703A NL7713703A (nl) | 1976-12-15 | 1977-12-11 | Tussenprodukt voor de bereiding van 6,7-dimetho- xy-4-amino-2-(4-(furoyl)-1-piperazinyl) china- zoline dat een antihypertensieve werking heeft. |
| NO774263A NO146239C (no) | 1976-12-15 | 1977-12-12 | Mellomprodukt for fremstilling av 6,7-dimetoksy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtrykksenkende virkning |
| PL1977202898A PL106201B1 (pl) | 1976-12-15 | 1977-12-13 | Sposob wytwarzania 3,4-dwumetoksy-6-/4-/2-furoilo/-1-piperazynylotiokarbamido/-benzonitrylu |
| HU77OI217A HU174048B (hu) | 1976-12-15 | 1977-12-13 | Sposob poluchenija novogo intermediarnogo soedinenija dlja poluchenija 6,7-dimetoksi-4-amino-2-kvadratnaja skobka-4-skobka-2-furil-skobka zakryta-1-piperazinil-kvadratnaja skobka zakryta-kinazolina s antigipertenzivnojj aktivnost'ju |
| DK558377A DK145822C (da) | 1976-12-15 | 1977-12-14 | 3,4-dimethoxy-6-(4-(2-furoyl)-1-piperazinylthiocarbamido)benzonitril til anvendelse som mellemprodukt ved fremstillingen af 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)quinazolin |
| DE19772755638 DE2755638A1 (de) | 1976-12-15 | 1977-12-14 | Zwischenprodukt zur herstellung von blutdrucksenkendem 6,7-dimethoxy- 4-amino-2-eckige klammer auf 4-(2-furoyl)- 1-piperazinyl eckige klammer zu chinazolin |
| BE183425A BE861822A (fr) | 1976-12-15 | 1977-12-14 | Produit intermediaire pour la preparation de la 6,7-dimethoxy-4-amino-2(4-(2-furoyl)-1-piperazinyl)quinazoline exercant un effet antihypertensif |
| SU772555751A SU923370A3 (ru) | 1976-12-15 | 1977-12-14 | Способ получени 3,4-диметокси-6-/4-(2-фуроил)-1-пиперазинилтиокарбамидо/-бензонитрила |
| CA293,066A CA1102332A (en) | 1976-12-15 | 1977-12-14 | Intermediate product for the production of 6,7- dimethoxy-4-amino-2-¬4-(2-furoyl)-1- piperazinyl|quinazoline having an antihypertensive effect |
| DD77202667A DD134226A1 (de) | 1976-12-15 | 1977-12-15 | Verfahren zur herstellung von 3,4-demethoxy-6-eckige klammer auf 4-(2-furoyl)-1-piperazinyl eckige klammer zu-benzonitril |
| JP15157177A JPS5387375A (en) | 1976-12-15 | 1977-12-15 | 3*44dimethoxyy66*44*22furoyl**11piperadinylthioo carbamide*benzonitrile and method for its production |
| CS778433A CS197312B2 (en) | 1976-12-15 | 1977-12-15 | Method of producing 3,4-dimethoxy-6-/4-/2-furoyl/-1-piperazinyl-thiocarbamido/benzonitrile |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI763614A FI58124C (fi) | 1976-12-15 | 1976-12-15 | Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan |
| FI763614 | 1976-12-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763614A7 FI763614A7 (fi) | 1978-06-16 |
| FI58124B FI58124B (fi) | 1980-08-29 |
| FI58124C true FI58124C (fi) | 1980-12-10 |
Family
ID=8510504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI763614A FI58124C (fi) | 1976-12-15 | 1976-12-15 | Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI67699C (fi) * | 1979-01-31 | 1985-05-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935213A (en) * | 1973-12-05 | 1976-01-27 | Pfizer Inc. | Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives |
-
1976
- 1976-12-15 FI FI763614A patent/FI58124C/fi not_active IP Right Cessation
-
1977
- 1977-11-24 CH CH1438277A patent/CH630624A5/de not_active IP Right Cessation
- 1977-11-25 SE SE7713377A patent/SE424993B/sv not_active IP Right Cessation
- 1977-12-05 AT AT867177A patent/AT358047B/de not_active IP Right Cessation
- 1977-12-05 ZA ZA00777222A patent/ZA777222B/xx unknown
- 1977-12-11 NL NL7713703A patent/NL7713703A/xx not_active Application Discontinuation
- 1977-12-12 NO NO774263A patent/NO146239C/no unknown
- 1977-12-13 HU HU77OI217A patent/HU174048B/hu not_active IP Right Cessation
- 1977-12-13 PL PL1977202898A patent/PL106201B1/pl unknown
- 1977-12-14 DK DK558377A patent/DK145822C/da not_active IP Right Cessation
- 1977-12-14 CA CA293,066A patent/CA1102332A/en not_active Expired
- 1977-12-14 DE DE19772755638 patent/DE2755638A1/de not_active Ceased
- 1977-12-14 SU SU772555751A patent/SU923370A3/ru active
- 1977-12-14 BE BE183425A patent/BE861822A/xx not_active IP Right Cessation
- 1977-12-15 JP JP15157177A patent/JPS5387375A/ja active Granted
- 1977-12-15 DD DD77202667A patent/DD134226A1/xx unknown
- 1977-12-15 CS CS778433A patent/CS197312B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO146239C (no) | 1982-08-25 |
| AT358047B (de) | 1980-08-11 |
| DD134226A1 (de) | 1979-02-14 |
| NO774263L (no) | 1978-06-16 |
| PL202898A1 (pl) | 1978-08-28 |
| DK145822C (da) | 1983-08-29 |
| DK145822B (da) | 1983-03-14 |
| CH630624A5 (en) | 1982-06-30 |
| SU923370A3 (ru) | 1982-04-23 |
| FI763614A7 (fi) | 1978-06-16 |
| SE424993B (sv) | 1982-08-23 |
| NO146239B (no) | 1982-05-18 |
| CA1102332A (en) | 1981-06-02 |
| PL106201B1 (pl) | 1979-12-31 |
| SE7713377L (sv) | 1978-06-16 |
| JPS6225145B2 (enrdf_load_stackoverflow) | 1987-06-01 |
| ATA867177A (de) | 1980-01-15 |
| FI58124B (fi) | 1980-08-29 |
| CS197312B2 (en) | 1980-04-30 |
| NL7713703A (nl) | 1978-06-19 |
| DE2755638A1 (de) | 1978-06-22 |
| BE861822A (fr) | 1978-03-31 |
| DK558377A (da) | 1978-06-16 |
| HU174048B (hu) | 1979-10-28 |
| JPS5387375A (en) | 1978-08-01 |
| ZA777222B (en) | 1978-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ORION-YHTYMAE OY |