FI58125C - Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan - Google Patents
Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan Download PDFInfo
- Publication number
- FI58125C FI58125C FI763613A FI763613A FI58125C FI 58125 C FI58125 C FI 58125C FI 763613 A FI763613 A FI 763613A FI 763613 A FI763613 A FI 763613A FI 58125 C FI58125 C FI 58125C
- Authority
- FI
- Finland
- Prior art keywords
- furoyl
- dimethoxy
- piperazinyl
- amino
- quinazoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 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 18
- 238000002360 preparation method Methods 0.000 claims description 11
- -1 2-furoyl Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 229960001289 prazosin Drugs 0.000 description 12
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 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 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KJSWIMFSQRWZBK-UHFFFAOYSA-N 4-(furan-2-carbonyl)piperazine-1-carbonitrile Chemical compound C=1C=COC=1C(=O)N1CCN(C#N)CC1 KJSWIMFSQRWZBK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 239000005457 ice water Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 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
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-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
- 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 1
- LSZOFTRAUPQMAG-UHFFFAOYSA-N C(=S)N.O1C(=CC=C1)C(=O)N1CCNCC1 Chemical compound C(=S)N.O1C(=CC=C1)C(=O)N1CCNCC1 LSZOFTRAUPQMAG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- ZMTPYWSLOOYBIS-UHFFFAOYSA-N [S-]C#N.[NH2+]1CCNCC1 Chemical compound [S-]C#N.[NH2+]1CCNCC1 ZMTPYWSLOOYBIS-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RUUFMZWBOOOMFM-UHFFFAOYSA-N methyl 4-(furan-2-carbonyl)piperazine-1-carboximidate Chemical compound C1CN(C(=N)OC)CCN1C(=O)C1=CC=CO1 RUUFMZWBOOOMFM-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 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 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)
Priority Applications (17)
| 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 |
| CH1438177A CH630625A5 (en) | 1976-12-15 | 1977-11-24 | Process for the preparation of antihypertensive 6,7-dimethoxy-4-amino-2-[4-(2-furoyl)-1-piperazinyl]quinazoline |
| SE7713376A SE435284B (sv) | 1976-12-15 | 1977-11-25 | Forfarande for framstellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinoazolin |
| AT867277A AT358048B (de) | 1976-12-15 | 1977-12-05 | Verfahren zur herstellung von 6,7-dimethoxy-4- -amino-2-(4-(2-furoyl)-1-piperazinyl)chinazolin |
| ZA00777223A ZA777223B (en) | 1976-12-15 | 1977-12-05 | Method for the production of 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)quinazoline having an antihypertensive effect |
| NL7713702A NL7713702A (nl) | 1976-12-15 | 1977-12-11 | Werkwijze voor de bereiding van 6,7-dimethoxy- -4-amino-2-(4-(2-furoyl)-1-piperazinyl) china- zoline dat een antihypertensieve werking heeft. |
| NO774262A NO147244C (no) | 1976-12-15 | 1977-12-12 | Fremgangsmaate til fremstilling av 6,7-dimetoksy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin |
| HU77OA538A HU174047B (hu) | 1976-12-15 | 1977-12-13 | Sposob poluchenija 6,7-dimetoksi-4-amino-2-kvadratnaja skobka-4-skobka-2-furil-skobka zakryta-piperazinil-kvadratnaja skobka zakryta-kinazolina s antigipertenzivnojj aktivnost'ju |
| PL1977202899A PL106031B1 (pl) | 1976-12-15 | 1977-12-13 | Sposob wytwarzania 6,7-dwumetoksy-4-amino-2-/4-/2-furoilo/-1-piperazynylo/chinazoliny o dzialaniu przeciwnadcisnieniowym |
| DE19772755637 DE2755637A1 (de) | 1976-12-15 | 1977-12-14 | Verfahren zur herstellung von blutdrucksenkendem 6,7-dimethoxy-4-amino-2- eckige klammer auf 4-(2-furoyl)-1-piperazinyl eckige klammer zu chinazolin |
| DK558277A DK144972C (da) | 1976-12-15 | 1977-12-14 | Fremgangsmaade til fremstilling af 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)quinazolin |
| SU772555247A SU753360A3 (ru) | 1976-12-15 | 1977-12-14 | Способ получени 6,7-диметокси-4амино-2(4,/2-фуроил/-1-пиперазинил)хиназолина |
| BE183424A BE861821A (fr) | 1976-12-15 | 1977-12-14 | Procede de preparation de la 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)-quinazoline exercant un effet antihypertensif |
| CA293,065A CA1092117A (en) | 1976-12-15 | 1977-12-14 | Method for the production of 6,7-dimethoxy-4-amino-2- ¬4-(2-furoyl)-1-piperazinyl| quinazoline having an antihypertensive effect |
| JP15157077A JPS5387377A (en) | 1976-12-15 | 1977-12-15 | Method of producing 6*77dimethoxyy44aminoo22 *44*22furoyl**11piperazinyl*quinazoline |
| 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 |
| DD7700202666A DD133671A1 (de) | 1976-12-15 | 1977-12-15 | Verfahren zur herstellung von 6,7-dimethoxy-4-amino-2-eckige klammer auf 4-(2-furoyl)-1-piperazinyl eckige klammer zu chinazolin |
Applications Claiming Priority (2)
| 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 |
| FI763613 | 1976-12-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763613A7 FI763613A7 (fi) | 1978-06-16 |
| FI58125B FI58125B (fi) | 1980-08-29 |
| FI58125C true FI58125C (fi) | 1985-01-02 |
Family
ID=8510503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
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 |
| JP6231556B2 (ja) * | 2012-05-23 | 2017-11-15 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | Ｎ−［５−（３，５−ジフルオロ−ベンジル）−１ｈ−インダゾール−３−イル］−４−（４−メチル−ピペラジン−１−イル）−２−（テトラヒドロ−ピラン−４−イルアミノ）−ベンズアミドの調製方法 |
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 DK DK558277A patent/DK144972C/da not_active IP Right Cessation
- 1977-12-14 CA CA293,065A patent/CA1092117A/en not_active Expired
- 1977-12-15 JP JP15157077A patent/JPS5387377A/ja active Granted
- 1977-12-15 DD DD7700202666A patent/DD133671A1/xx unknown
- 1977-12-15 CS CS778432A patent/CS195347B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7713702A (nl) | 1978-06-19 |
| CA1092117A (en) | 1980-12-23 |
| DK144972B (da) | 1982-07-19 |
| BE861821A (fr) | 1978-03-31 |
| FI58125B (fi) | 1980-08-29 |
| PL106031B1 (pl) | 1979-11-30 |
| CS195347B2 (en) | 1980-01-31 |
| JPS5387377A (en) | 1978-08-01 |
| ATA867277A (de) | 1980-01-15 |
| DD133671A1 (de) | 1979-01-17 |
| NO147244C (no) | 1984-10-09 |
| PL202899A1 (pl) | 1978-08-28 |
| DE2755637C2 (enrdf_load_stackoverflow) | 1987-09-24 |
| AT358048B (de) | 1980-08-11 |
| DE2755637A1 (de) | 1978-06-22 |
| DK144972C (da) | 1988-08-29 |
| ZA777223B (en) | 1978-09-27 |
| HU174047B (hu) | 1979-10-28 |
| SE435284B (sv) | 1984-09-17 |
| NO147244B (no) | 1982-11-22 |
| SU753360A3 (ru) | 1980-07-30 |
| NO774262L (no) | 1978-06-16 |
| CH630625A5 (en) | 1982-06-30 |
| DK558277A (da) | 1978-06-16 |
| FI763613A7 (fi) | 1978-06-16 |
| SE7713376L (sv) | 1978-06-16 |
| JPS6225147B2 (enrdf_load_stackoverflow) | 1987-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ORION-YHTYMAE OY |