CS195347B2 - Process for preparing antihypertensive 6,7-dimethoxy4-4-amino-2-/4-/2-furoyl/-1-piperazinyl/quinazoline - Google Patents
Process for preparing antihypertensive 6,7-dimethoxy4-4-amino-2-/4-/2-furoyl/-1-piperazinyl/quinazoline Download PDFInfo
- Publication number
- CS195347B2 CS195347B2 CS778432A CS843277A CS195347B2 CS 195347 B2 CS195347 B2 CS 195347B2 CS 778432 A CS778432 A CS 778432A CS 843277 A CS843277 A CS 843277A CS 195347 B2 CS195347 B2 CS 195347B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dimethoxy
- furoyl
- piperazinyl
- formula
- amino
- Prior art date
Links
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title description 4
- 230000003276 anti-hypertensive effect Effects 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 24
- -1 alkali metal amide Chemical class 0.000 claims abstract description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 14
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
- 239000002798 polar solvent Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- GYAUHKHLMYZHEM-UHFFFAOYSA-N [4-(4-amino-6,7-dimethoxyquinolin-2-yl)piperazin-1-yl]-(furan-2-yl)methanone Chemical compound C=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 GYAUHKHLMYZHEM-UHFFFAOYSA-N 0.000 claims 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract description 30
- 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 abstract description 10
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 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 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229960001289 prazosin Drugs 0.000 description 8
- SADPINFEWFPMEA-UHFFFAOYSA-N furan-2-yl(piperazin-1-yl)methanone Chemical compound C=1C=COC=1C(=O)N1CCNCC1 SADPINFEWFPMEA-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BJAYMNUBIULRMF-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N)=C(C#N)C=C1OC BJAYMNUBIULRMF-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000001816 cooling Methods 0.000 description 5
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-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
- 239000000543 intermediate Substances 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
- 239000000725 suspension 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
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-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
- HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-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
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- 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 |
|---|---|---|---|
| FI763613A FI58125C (fi) | 1976-12-15 | 1976-12-15 | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195347B2 true CS195347B2 (en) | 1980-01-31 |
Family
ID=8510503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS778432A CS195347B2 (en) | 1976-12-15 | 1977-12-15 | Process for preparing antihypertensive 6,7-dimethoxy4-4-amino-2-/4-/2-furoyl/-1-piperazinyl/quinazoline |
Country Status (17)
Families Citing this family (2)
| 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 |
| PL3290414T3 (pl) * | 2012-05-23 | 2020-01-31 | Nerviano Medical Sciences S.R.L. | Sposób otrzymywania n-[5-(3,5-difluorobenzylo)-1h-indazol-3-ilo]-4-(4-metylopiperazyn-1-ylo)-2-(tetrahydropiran-4-yloamino)benzamidu |
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 FI763613A patent/FI58125C/fi not_active IP Right Cessation
-
1977
- 1977-11-24 CH CH1438177A patent/CH630625A5/de not_active IP Right Cessation
- 1977-11-25 SE SE7713376A patent/SE435284B/xx not_active IP Right Cessation
- 1977-12-05 ZA ZA00777223A patent/ZA777223B/xx unknown
- 1977-12-05 AT AT867277A patent/AT358048B/de not_active IP Right Cessation
- 1977-12-11 NL NL7713702A patent/NL7713702A/xx not_active Application Discontinuation
- 1977-12-12 NO NO774262A patent/NO147244C/no unknown
- 1977-12-13 HU HU77OA538A patent/HU174047B/hu not_active IP Right Cessation
- 1977-12-13 PL PL1977202899A patent/PL106031B1/pl unknown
- 1977-12-14 SU SU772555247A patent/SU753360A3/ru active
- 1977-12-14 DE DE19772755637 patent/DE2755637A1/de active Granted
- 1977-12-14 BE BE183424A patent/BE861821A/xx not_active IP Right Cessation
- 1977-12-14 CA CA293,065A patent/CA1092117A/en not_active Expired
- 1977-12-14 DK DK558277A patent/DK144972C/da not_active IP Right Cessation
- 1977-12-15 JP JP15157077A patent/JPS5387377A/ja active Granted
- 1977-12-15 CS CS778432A patent/CS195347B2/cs unknown
- 1977-12-15 DD DD7700202666A patent/DD133671A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI58125B (fi) | 1980-08-29 |
| DD133671A1 (de) | 1979-01-17 |
| FI58125C (fi) | 1985-01-02 |
| SU753360A3 (ru) | 1980-07-30 |
| CH630625A5 (en) | 1982-06-30 |
| PL202899A1 (pl) | 1978-08-28 |
| NO147244C (no) | 1984-10-09 |
| NL7713702A (nl) | 1978-06-19 |
| DE2755637A1 (de) | 1978-06-22 |
| ZA777223B (en) | 1978-09-27 |
| AT358048B (de) | 1980-08-11 |
| FI763613A7 (fi) | 1978-06-16 |
| BE861821A (fr) | 1978-03-31 |
| CA1092117A (en) | 1980-12-23 |
| DE2755637C2 (enrdf_load_html_response) | 1987-09-24 |
| DK558277A (da) | 1978-06-16 |
| JPS6225147B2 (enrdf_load_html_response) | 1987-06-01 |
| DK144972B (da) | 1982-07-19 |
| SE7713376L (sv) | 1978-06-16 |
| SE435284B (sv) | 1984-09-17 |
| NO774262L (no) | 1978-06-16 |
| HU174047B (hu) | 1979-10-28 |
| DK144972C (da) | 1988-08-29 |
| NO147244B (no) | 1982-11-22 |
| ATA867277A (de) | 1980-01-15 |
| PL106031B1 (pl) | 1979-11-30 |
| JPS5387377A (en) | 1978-08-01 |
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