SU900810A3 - Способ получени 4-арилхиназолин-2/1н/-онов - Google Patents
Способ получени 4-арилхиназолин-2/1н/-онов Download PDFInfo
- Publication number
- SU900810A3 SU900810A3 SU782658400A SU2658400A SU900810A3 SU 900810 A3 SU900810 A3 SU 900810A3 SU 782658400 A SU782658400 A SU 782658400A SU 2658400 A SU2658400 A SU 2658400A SU 900810 A3 SU900810 A3 SU 900810A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- yield
- isopropyl
- mixture
- benzene
- quinazolin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- TYNNEEKKMHSZMO-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-1h-quinazolin-2-one Chemical compound C1C=CC=C2NC(=O)NCC21 TYNNEEKKMHSZMO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 239000011133 lead Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- 239000010410 layer Substances 0.000 claims 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims 2
- ZWOUXWWGKJBAHQ-UHFFFAOYSA-N fluproquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=C(F)C=C1 ZWOUXWWGKJBAHQ-UHFFFAOYSA-N 0.000 claims 2
- 239000012044 organic layer Substances 0.000 claims 2
- 150000003738 xylenes Chemical class 0.000 claims 2
- 239000011787 zinc oxide Substances 0.000 claims 2
- VAFNJIFAZJWWNI-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methoxy-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(OC)=CC=C2N1CC1CC1 VAFNJIFAZJWWNI-UHFFFAOYSA-N 0.000 claims 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JAPCFGJAINHVJK-UHFFFAOYSA-N 5,7-dimethyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC(C)=C2C=1C1=CC=CC=C1 JAPCFGJAINHVJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000012258 stirred mixture Substances 0.000 claims 1
- HCHKCACWOHOZIP-NJFSPNSNSA-N zinc-67 Chemical compound [67Zn] HCHKCACWOHOZIP-NJFSPNSNSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- 229910052976 metal sulfide Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 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
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83041177A | 1977-09-06 | 1977-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU900810A3 true SU900810A3 (ru) | 1982-01-23 |
Family
ID=25256956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782658400A SU900810A3 (ru) | 1977-09-06 | 1978-09-05 | Способ получени 4-арилхиназолин-2/1н/-онов |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5455583A (es) |
| AR (1) | AR228235A1 (es) |
| AT (1) | AT376211B (es) |
| AU (1) | AU523728B2 (es) |
| BE (1) | BE870185A (es) |
| CA (1) | CA1111847A (es) |
| CH (1) | CH642638A5 (es) |
| DD (1) | DD138657A5 (es) |
| DE (1) | DE2837403A1 (es) |
| DK (1) | DK144999C (es) |
| ES (1) | ES473103A1 (es) |
| FI (1) | FI66362C (es) |
| FR (1) | FR2401917A1 (es) |
| GB (1) | GB2003873B (es) |
| GR (1) | GR73605B (es) |
| HU (1) | HU183018B (es) |
| IE (1) | IE47184B1 (es) |
| IL (1) | IL55492A (es) |
| IT (1) | IT1106289B (es) |
| NL (1) | NL7808981A (es) |
| NO (1) | NO782945L (es) |
| NZ (1) | NZ188329A (es) |
| PL (1) | PL114207B1 (es) |
| PT (1) | PT68505A (es) |
| SE (1) | SE7809098L (es) |
| SU (1) | SU900810A3 (es) |
| YU (1) | YU211078A (es) |
| ZA (1) | ZA785061B (es) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2358972C2 (ru) * | 2002-12-23 | 2009-06-20 | Новартис Аг | Производные арилхиназолина, которые способствуют высвобождению паратиреоидного гормона |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH637114A5 (de) * | 1978-08-16 | 1983-07-15 | Sandoz Ag | 2-(n-carboalkoxyamino)-benzophenone, ihre herstellung und verwendung. |
| CH645362A5 (de) * | 1979-07-05 | 1984-09-28 | Sandoz Ag | Verfahren zur herstellung von 4-phenyl-2(1h)-chinazolinonen. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE785937A (fr) * | 1971-07-08 | 1973-01-08 | Sandoz Sa | Nouveaux derives de la quinazoline, leur preparation et leur application comme medicaments |
-
1978
- 1978-08-25 CH CH904578A patent/CH642638A5/de not_active IP Right Cessation
- 1978-08-28 FI FI782619A patent/FI66362C/fi not_active IP Right Cessation
- 1978-08-28 DE DE19782837403 patent/DE2837403A1/de not_active Withdrawn
- 1978-08-29 DK DK382078A patent/DK144999C/da not_active IP Right Cessation
- 1978-08-29 SE SE7809098A patent/SE7809098L/xx unknown
- 1978-08-29 NO NO782945A patent/NO782945L/no unknown
- 1978-08-31 FR FR7825162A patent/FR2401917A1/fr active Granted
- 1978-08-31 GB GB7835143A patent/GB2003873B/en not_active Expired
- 1978-09-01 NL NL7808981A patent/NL7808981A/xx not_active Application Discontinuation
- 1978-09-01 IT IT50936/78A patent/IT1106289B/it active
- 1978-09-04 BE BE190237A patent/BE870185A/xx not_active IP Right Cessation
- 1978-09-04 JP JP10769178A patent/JPS5455583A/ja active Pending
- 1978-09-04 PT PT68505A patent/PT68505A/pt unknown
- 1978-09-04 NZ NZ188329A patent/NZ188329A/xx unknown
- 1978-09-04 IE IE1780/78A patent/IE47184B1/en unknown
- 1978-09-04 IL IL55492A patent/IL55492A/xx unknown
- 1978-09-05 AU AU39571/78A patent/AU523728B2/en not_active Expired
- 1978-09-05 AR AR273577A patent/AR228235A1/es active
- 1978-09-05 CA CA310,645A patent/CA1111847A/en not_active Expired
- 1978-09-05 AT AT0639978A patent/AT376211B/de not_active IP Right Cessation
- 1978-09-05 ES ES473103A patent/ES473103A1/es not_active Expired
- 1978-09-05 PL PL1978209423A patent/PL114207B1/pl unknown
- 1978-09-05 DD DD78207656A patent/DD138657A5/xx unknown
- 1978-09-05 SU SU782658400A patent/SU900810A3/ru active
- 1978-09-05 YU YU02110/78A patent/YU211078A/xx unknown
- 1978-09-05 HU HU78SA3133A patent/HU183018B/hu unknown
- 1978-09-06 ZA ZA785061A patent/ZA785061B/xx unknown
-
1980
- 1980-01-04 GR GR57147A patent/GR73605B/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2358972C2 (ru) * | 2002-12-23 | 2009-06-20 | Новартис Аг | Производные арилхиназолина, которые способствуют высвобождению паратиреоидного гормона |
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