CH545296A - Verfahren zur Herstellung von 6,7,8-Trialkoxychinazolin-4(3H)-onen - Google Patents
Verfahren zur Herstellung von 6,7,8-Trialkoxychinazolin-4(3H)-onenInfo
- Publication number
- CH545296A CH545296A CH1519573A CH1519573A CH545296A CH 545296 A CH545296 A CH 545296A CH 1519573 A CH1519573 A CH 1519573A CH 1519573 A CH1519573 A CH 1519573A CH 545296 A CH545296 A CH 545296A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- amino
- formamide
- known per
- Prior art date
Links
- QYUJUMGMWSGPJJ-UHFFFAOYSA-N 6,7,8-trimethoxyquinazolin-4-amine Chemical class N1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1N QYUJUMGMWSGPJJ-UHFFFAOYSA-N 0.000 title abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- ORRMRZIJVLFOOZ-UHFFFAOYSA-N 6,7,8-trimethoxy-1h-quinazolin-4-one Chemical compound COC1=C(OC)C(OC)=CC2=C1NC=NC2=O ORRMRZIJVLFOOZ-UHFFFAOYSA-N 0.000 claims description 4
- CDLRORXPBBREER-UHFFFAOYSA-N COCC(C(COC)=C1COC)=CC(C(O)=O)=C1N Chemical compound COCC(C(COC)=C1COC)=CC(C(O)=O)=C1N CDLRORXPBBREER-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 229910004679 ONO2 Inorganic materials 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 230000000916 dilatatory effect Effects 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87043969A | 1969-12-05 | 1969-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH545296A true CH545296A (de) | 1974-01-31 |
Family
ID=25355372
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1519573A CH545296A (de) | 1969-12-05 | 1970-11-23 | Verfahren zur Herstellung von 6,7,8-Trialkoxychinazolin-4(3H)-onen |
| CH1519273A CH554878A (de) | 1969-12-05 | 1970-11-23 | Verfahren zur herstellung von in stellung 4 substituierten 6,7,8-trialkoxychinazolinen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1519273A CH554878A (de) | 1969-12-05 | 1970-11-23 | Verfahren zur herstellung von in stellung 4 substituierten 6,7,8-trialkoxychinazolinen. |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT317218B (ro) |
| CH (2) | CH545296A (ro) |
| DK (2) | DK126329B (ro) |
| NO (1) | NO130477C (ro) |
| PL (1) | PL77821B1 (ro) |
| RO (1) | RO60107A (ro) |
| SU (1) | SU400098A3 (ro) |
| ZA (1) | ZA708200B (ro) |
-
1970
- 1970-08-28 NO NO3285/70A patent/NO130477C/no unknown
- 1970-08-28 DK DK444470AA patent/DK126329B/da unknown
- 1970-11-23 CH CH1519573A patent/CH545296A/de not_active IP Right Cessation
- 1970-11-23 CH CH1519273A patent/CH554878A/xx not_active IP Right Cessation
- 1970-12-03 PL PL1970150248A patent/PL77821B1/pl unknown
- 1970-12-03 RO RO65179A patent/RO60107A/ro unknown
- 1970-12-04 AT AT1094670A patent/AT317218B/de not_active IP Right Cessation
- 1970-12-04 ZA ZA708200A patent/ZA708200B/xx unknown
- 1970-12-04 SU SU1499660A patent/SU400098A3/ru active
-
1971
- 1971-08-11 DK DK392471AA patent/DK125799B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH554878A (de) | 1974-10-15 |
| ZA708200B (en) | 1972-07-26 |
| SU400098A3 (ro) | 1973-10-03 |
| RO60107A (ro) | 1976-08-15 |
| NO130477B (ro) | 1974-09-09 |
| NO130477C (ro) | 1974-12-18 |
| DK125799B (da) | 1973-05-07 |
| PL77821B1 (en) | 1975-04-30 |
| DK126329B (da) | 1973-07-02 |
| AT317218B (de) | 1974-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |