PL412154A1 - Sposób wytwarzania 1-fenylo-2-(2-hydroksyetylo)-6H-imidazo[1,5-c]chinazolino-3,5-dionu i 1-fenylo-2-(2-hydroksypropylo)-6H-imidazo[1,5-c]chinazolino-3,5-dionu - Google Patents
Sposób wytwarzania 1-fenylo-2-(2-hydroksyetylo)-6H-imidazo[1,5-c]chinazolino-3,5-dionu i 1-fenylo-2-(2-hydroksypropylo)-6H-imidazo[1,5-c]chinazolino-3,5-dionuInfo
- Publication number
- PL412154A1 PL412154A1 PL412154A PL41215415A PL412154A1 PL 412154 A1 PL412154 A1 PL 412154A1 PL 412154 A PL412154 A PL 412154A PL 41215415 A PL41215415 A PL 41215415A PL 412154 A1 PL412154 A1 PL 412154A1
- Authority
- PL
- Poland
- Prior art keywords
- stage
- imidazo
- dione
- phenyl
- solvent
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- PIFKVUFRJYUEBI-UHFFFAOYSA-N 1-phenyl-2,6-dihydroimidazo[1,5-c]quinazoline-3,5-dione Chemical compound C=12C3=CC=CC=C3NC(=O)N2C(=O)NC=1C1=CC=CC=C1 PIFKVUFRJYUEBI-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- KJMFQJFNQYWQAV-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinazoline Chemical group C1=NC=NC2=C(NC=N3)C3=CC=C21 KJMFQJFNQYWQAV-UHFFFAOYSA-N 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 150000002924 oxiranes Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Sposób dotyczy wytwarzania związku o wzorze strukturalnym 1, gdzie R oznacza odpowiednio atom wodoru -H albo grupę metylową -CH3, w reakcjach 1-fenylo-2H,6H-imidazo[1,5-c]chinazolino-3,5-dionu z oksiranami w postaci odpowiednio tlenku etylenu dla R = -H lub tlenku propylenu dla R = -CH3. W pierwszym etapie prowadzi się reakcje w reaktorze ciśnieniowym, przy stosunku molowym 1-fenylo-2H,6H-imidazo[1,5-c]chinazolino-3,5-dionu do oksiranu równym 1:1, w rozpuszczalniku w obecności trietyloaminy jako katalizatora, zaś w drugim etapie po zakończeniu reakcji oddestylowuje się pod zmniejszonym ciśnieniem katalizator i rozpuszczalnik, po czym otrzymany związek wytrąca acetonem, odsącza i następnie krystalizuje z etanolu. W pierwszym etapie, w przypadku tlenku etylenu reakcje prowadzi się w temperaturze 60 ÷ 70°C przez co najmniej 70 godzin, zaś w przypadku tlenku propylenu w temperaturze 70 ÷ 90°C przez co najmniej 78 godzin. Ponadto w pierwszym etapie jako rozpuszczalnik stosuje się sulfotlenek dimetylu, zaś w drugim etapie oddestylowanie katalizatora i rozpuszczalnika prowadzi się pod ciśnieniem mniejszym niż 10 mm Hg. Zastosowanie: jako potencjalne związki wykazujące czynność biologiczną, związki wyjściowe w syntezie leków, lub substraty do syntezy innych związków organicznych z pierścieniem imidazochinazolinowym.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL412154A PL236023B1 (pl) | 2015-04-28 | 2015-04-28 | Sposób wytwarzania 1-fenylo-2-(2-hydroksyetylo)-6H-imidazo[ 1,5-c]chinazolino-3,5-dionu i 1-fenylo-2-(2-hydroksypropylo)-6H- -imidazo[1,5-c]chinazolino-3,5-dionu |
| EP15781453.4A EP3288947A1 (en) | 2015-04-28 | 2015-09-07 | Preparation method for 1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione and 1-phenyl-2,6-bis(2-hydroxypropyl)imidazo[1,5-c]quinazoline-3,5-dione |
| PCT/PL2015/050037 WO2016175668A1 (en) | 2015-04-28 | 2015-09-07 | Preparation method for 1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione and 1-phenyl-2,6-bis(2-hydroxypropyl)imidazo[1,5-c]quinazoline-3,5-dione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL412154A PL236023B1 (pl) | 2015-04-28 | 2015-04-28 | Sposób wytwarzania 1-fenylo-2-(2-hydroksyetylo)-6H-imidazo[ 1,5-c]chinazolino-3,5-dionu i 1-fenylo-2-(2-hydroksypropylo)-6H- -imidazo[1,5-c]chinazolino-3,5-dionu |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL412154A1 true PL412154A1 (pl) | 2016-11-07 |
| PL236023B1 PL236023B1 (pl) | 2020-11-30 |
Family
ID=54330001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL412154A PL236023B1 (pl) | 2015-04-28 | 2015-04-28 | Sposób wytwarzania 1-fenylo-2-(2-hydroksyetylo)-6H-imidazo[ 1,5-c]chinazolino-3,5-dionu i 1-fenylo-2-(2-hydroksypropylo)-6H- -imidazo[1,5-c]chinazolino-3,5-dionu |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP3288947A1 (pl) |
| PL (1) | PL236023B1 (pl) |
| WO (1) | WO2016175668A1 (pl) |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH549045A (de) | 1970-01-30 | 1974-05-15 | Ciba Geigy Ag | Verfahren zur herstellung von neuen diglycidylderivaten von n-heterocyclischen verbindungen. |
| DE1954503C3 (de) | 1968-11-11 | 1974-09-19 | Ciba Geigy Ag | Diglycidylaether von N-heterocyclischen Verbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung |
| CH523279A (de) | 1968-11-11 | 1972-05-31 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Diglycidylverbindungen von N-heterocyclischen Verbindungen und deren Verwendung |
| ES373376A1 (es) | 1968-11-11 | 1972-01-16 | Ciba Geigy | Procedimiento para la preparacion de nuevos esteres dibli- cidilicos. |
| US4161594A (en) | 1968-11-11 | 1979-07-17 | Ciba-Geigy Ag | Dialcohols |
| SU372815A3 (pl) | 1968-11-11 | 1973-03-01 | ||
| AT300826B (de) | 1968-11-11 | 1972-08-10 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Diglycidylverbindungen |
| GB1334462A (en) | 1968-11-11 | 1973-10-17 | Ciba Geigy Ag | Hydroxy derivatives of n-heterocyclic compounds and processes for their manufacture |
| DE2104279A1 (en) | 1968-11-11 | 1971-08-05 | CIBA Geigy AG, Basel (Schweiz) | Diglycidyl derivs of heterocyclic cpds |
| CH521970A (de) | 1968-11-11 | 1972-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Mono- und Dialkoholen N-heterocyclischer Verbindungen |
| CH546242A (de) * | 1969-01-24 | 1974-02-28 | Ciba Geigy Ag | Verfahren zur herstellung von neuen dialkoholen von zwei n-heterocyclische ringe enthaltenden verbindungen. |
| ES386181A2 (es) | 1969-12-05 | 1974-01-01 | Ciba Geigy | Procedimiento para la preparacion de eteres diglicidilicos. |
| BE759863R (fr) | 1969-12-05 | 1971-06-04 | Ciba Geigy | Nouveaux derives diglycidyliques de composes n-heterocycliques,procede pour leur preparation et leur |
| SU407448A3 (pl) | 1970-01-30 | 1973-11-21 | ||
| ES379472A2 (es) | 1970-01-30 | 1975-11-01 | Ciba Geigy | Procedimiento para la preparacion de nuevos eteres diglici-dilicos. |
| CA962680A (en) | 1970-01-30 | 1975-02-11 | Hans Batzer | Five- or six-membered heterocyclic mono- and dialcohols |
| US4060525A (en) | 1970-01-30 | 1977-11-29 | Ciba-Geigy Ag | Five- or six-membered heterocyclic mono -and dialcohols |
| ES387744A2 (es) | 1970-01-30 | 1978-03-01 | Ciba Geigy | Procedimiento para la preparacion de nuevos eteres diglici- licos. |
| ZA703049B (en) | 1970-01-30 | 1971-01-27 | Ciba Ltd | Epoxide resin mixtures |
| ZA71501B (en) | 1970-01-30 | 1971-10-27 | Ciba Geigy Ag | New diglycidyl derivatives of n-heterocyclic compounds,process for their manufacture and use |
| GB0808948D0 (en) | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
| GB0808947D0 (en) | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
| GB0808950D0 (en) | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
-
2015
- 2015-04-28 PL PL412154A patent/PL236023B1/pl unknown
- 2015-09-07 EP EP15781453.4A patent/EP3288947A1/en not_active Withdrawn
- 2015-09-07 WO PCT/PL2015/050037 patent/WO2016175668A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PL236023B1 (pl) | 2020-11-30 |
| WO2016175668A1 (en) | 2016-11-03 |
| EP3288947A1 (en) | 2018-03-07 |
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