CH630624A5 - Processes for preparing 3,4-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinylthiocarbamido)benzo nitrile. - Google Patents
Processes for preparing 3,4-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinylthiocarbamido)benzo nitrile. Download PDFInfo
- Publication number
- CH630624A5 CH630624A5 CH1438277A CH1438277A CH630624A5 CH 630624 A5 CH630624 A5 CH 630624A5 CH 1438277 A CH1438277 A CH 1438277A CH 1438277 A CH1438277 A CH 1438277A CH 630624 A5 CH630624 A5 CH 630624A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethoxy
- furoyl
- amino
- formula
- benzonitrile
- Prior art date
Links
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 10
- -1 2-furoyl Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 9
- BJAYMNUBIULRMF-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N)=C(C#N)C=C1OC BJAYMNUBIULRMF-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 7
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229960001289 prazosin Drugs 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000001077 hypotensive effect Effects 0.000 claims 2
- 208000001953 Hypotension Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 208000021822 hypotensive Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- SADPINFEWFPMEA-UHFFFAOYSA-N furan-2-yl(piperazin-1-yl)methanone Chemical compound C=1C=COC=1C(=O)N1CCNCC1 SADPINFEWFPMEA-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 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 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZOJJJVRLKLQJNV-UHFFFAOYSA-N 2-(2,2-dimethoxyethoxy)-1,1-dimethoxyethane Chemical compound COC(OC)COCC(OC)OC ZOJJJVRLKLQJNV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 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)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630624A5 true CH630624A5 (en) | 1982-06-30 |
Family
ID=8510504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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. |
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 |
| 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 |
| FI58124C (fi) | 1980-12-10 |
| 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 |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |