CH642638A5 - Verfahren zur herstellung von chinazolin-2(1h)-onen. - Google Patents

Verfahren zur herstellung von chinazolin-2(1h)-onen. Download PDF

Info

Publication number: CH642638A5
Authority: CH; Switzerland
Prior art keywords: bromine; chlorine; fluorine; molar ratio; aryl
Prior art date: 1977-09-06

Application number

CH904578A

Other languages

German (de)

English (en)

Inventor

Joseph Antonio Smith

Original Assignee

Sandoz Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-09-06

Filing date

1978-08-25

Publication date

1984-04-30

1978-08-25 Application filed by Sandoz Ag filed Critical Sandoz Ag

1984-04-30 Publication of CH642638A5 publication Critical patent/CH642638A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000002736 metal compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Chemical group 0.000 claims description 12
239000000460 chlorine Chemical group 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 4
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
239000004215 Carbon black (E152) Substances 0.000 claims description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
238000006356 dehydrogenation reaction Methods 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
229910052976 metal sulfide Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
-1 6,7-methylenedioxy group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000001339 alkali metal compounds Chemical class 0.000 claims description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical compound C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 claims 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
150000001875 compounds Chemical class 0.000 description 12
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 7
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
229920002301 cellulose acetate Polymers 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
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 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000012485 toluene extract Substances 0.000 description 3
239000011787 zinc oxide Substances 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
YKFXBRUJMZNBAN-UHFFFAOYSA-N 7-methyl-4-phenyl-1-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C=2CC(C)CCC=2C=1C1=CC=CC=C1 YKFXBRUJMZNBAN-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
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 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BNHGVULTSGNVIX-UHFFFAOYSA-N 1-(2-ethoxyethoxy)ethanol Chemical compound CCOCCOC(C)O BNHGVULTSGNVIX-UHFFFAOYSA-N 0.000 description 1
NOJAJMMKDHHEGC-UHFFFAOYSA-N 4-(4-fluorophenyl)-7-methyl-1-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C=2CC(C)CCC=2C=1C1=CC=C(F)C=C1 NOJAJMMKDHHEGC-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
DBXATJCVRRXUTC-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1h-quinazolin-2-one Chemical compound C1CCCC2=NC(O)=NC=C21 DBXATJCVRRXUTC-UHFFFAOYSA-N 0.000 description 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 description 1
XLKSQIVWBJAEJN-UHFFFAOYSA-N 7-methyl-4-(4-methylphenyl)-1-propan-2-ylquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=C(C)C=C1 XLKSQIVWBJAEJN-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
NCCVXJLKVMTMGJ-UHFFFAOYSA-N bismuth;calcium Chemical compound [Ca+2].[Bi+3] NCCVXJLKVMTMGJ-UHFFFAOYSA-N 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
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 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011133 lead Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
HCHKCACWOHOZIP-NJFSPNSNSA-N zinc-67 Chemical compound [67Zn] HCHKCACWOHOZIP-NJFSPNSNSA-N 0.000 description 1
229910052726 zirconium Inorganic materials 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH904578A 1977-09-06 1978-08-25 Verfahren zur herstellung von chinazolin-2(1h)-onen. CH642638A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US83041177A	1977-09-06	1977-09-06

Publications (1)

Publication Number	Publication Date
CH642638A5 true CH642638A5 (de)	1984-04-30

Family

ID=25256956

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH904578A CH642638A5 (de)	1977-09-06	1978-08-25	Verfahren zur herstellung von chinazolin-2(1h)-onen.

Country Status (28)

Country	Link
JP (1)	JPS5455583A (fr)
AR (1)	AR228235A1 (fr)
AT (1)	AT376211B (fr)
AU (1)	AU523728B2 (fr)
BE (1)	BE870185A (fr)
CA (1)	CA1111847A (fr)
CH (1)	CH642638A5 (fr)
DD (1)	DD138657A5 (fr)
DE (1)	DE2837403A1 (fr)
DK (1)	DK144999C (fr)
ES (1)	ES473103A1 (fr)
FI (1)	FI66362C (fr)
FR (1)	FR2401917A1 (fr)
GB (1)	GB2003873B (fr)
GR (1)	GR73605B (fr)
HU (1)	HU183018B (fr)
IE (1)	IE47184B1 (fr)
IL (1)	IL55492A (fr)
IT (1)	IT1106289B (fr)
NL (1)	NL7808981A (fr)
NO (1)	NO782945L (fr)
NZ (1)	NZ188329A (fr)
PL (1)	PL114207B1 (fr)
PT (1)	PT68505A (fr)
SE (1)	SE7809098L (fr)
SU (1)	SU900810A3 (fr)
YU (1)	YU211078A (fr)
ZA (1)	ZA785061B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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.
GB0230015D0 (en) *	2002-12-23	2003-01-29	Novartis Ag	Organic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 NO NO782945A patent/NO782945L/no unknown
- 1978-08-29 SE SE7809098A patent/SE7809098L/xx unknown
- 1978-08-29 DK DK382078A patent/DK144999C/da not_active IP Right Cessation
- 1978-08-31 GB GB7835143A patent/GB2003873B/en not_active Expired
- 1978-08-31 FR FR7825162A patent/FR2401917A1/fr active Granted
- 1978-09-01 IT IT50936/78A patent/IT1106289B/it active
- 1978-09-01 NL NL7808981A patent/NL7808981A/xx not_active Application Discontinuation
- 1978-09-04 NZ NZ188329A patent/NZ188329A/xx unknown
- 1978-09-04 BE BE190237A patent/BE870185A/fr not_active IP Right Cessation
- 1978-09-04 JP JP10769178A patent/JPS5455583A/ja active Pending
- 1978-09-04 IE IE1780/78A patent/IE47184B1/en unknown
- 1978-09-04 PT PT68505A patent/PT68505A/fr unknown
- 1978-09-04 IL IL55492A patent/IL55492A/xx unknown
- 1978-09-05 SU SU782658400A patent/SU900810A3/ru active
- 1978-09-05 YU YU02110/78A patent/YU211078A/xx unknown
- 1978-09-05 AU AU39571/78A patent/AU523728B2/en not_active Expired
- 1978-09-05 DD DD78207656A patent/DD138657A5/xx unknown
- 1978-09-05 HU HU78SA3133A patent/HU183018B/hu unknown
- 1978-09-05 CA CA310,645A patent/CA1111847A/fr not_active Expired
- 1978-09-05 PL PL1978209423A patent/PL114207B1/pl unknown
- 1978-09-05 ES ES473103A patent/ES473103A1/es not_active Expired
- 1978-09-05 AT AT0639978A patent/AT376211B/de not_active IP Right Cessation
- 1978-09-05 AR AR273577A patent/AR228235A1/es active
- 1978-09-06 ZA ZA785061A patent/ZA785061B/xx unknown
1980
- 1980-01-04 GR GR57147A patent/GR73605B/el unknown

Also Published As

Publication number	Publication date
PL114207B1 (en)	1981-01-31
PT68505A (fr)	1978-10-01
IE47184B1 (en)	1984-01-11
DE2837403A1 (de)	1979-03-08
IT1106289B (it)	1985-11-11
DD138657A5 (de)	1979-11-14
IT7850936A0 (it)	1978-09-01
FI782619A7 (fi)	1979-03-07
AT376211B (de)	1984-10-25
FI66362C (fi)	1984-10-10
YU211078A (en)	1982-10-31
IL55492A0 (en)	1978-12-17
ES473103A1 (es)	1979-04-01
BE870185A (fr)	1979-03-05
FI66362B (fi)	1984-06-29
GB2003873B (en)	1982-03-10
IL55492A (en)	1982-08-31
SE7809098L (sv)	1979-03-07
PL209423A1 (pl)	1979-06-04
CA1111847A (fr)	1981-11-03
NO782945L (no)	1979-03-07
ATA639978A (de)	1984-03-15
IE781780L (en)	1979-03-06
AR228235A1 (es)	1983-02-15
AU523728B2 (en)	1982-08-12
NL7808981A (nl)	1979-03-08
FR2401917A1 (fr)	1979-03-30
HU183018B (en)	1984-04-28
GB2003873A (en)	1979-03-21
DK144999B (da)	1982-07-26
FR2401917B1 (fr)	1982-12-17
JPS5455583A (en)	1979-05-02
DK382078A (da)	1979-03-07
ZA785061B (en)	1980-04-30
AU3957178A (en)	1980-03-13
GR73605B (fr)	1984-03-26
DK144999C (da)	1982-12-13
NZ188329A (en)	1981-05-15
SU900810A3 (ru)	1982-01-23

Legal Events

Date	Code	Title	Description
1985-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2914494C2 (fr)	1989-07-20
DE1770561A1 (de)	1971-11-04	Verfahren zur Herstellung von Isochinuclidinderivaten
EP0606065B1 (fr)	1999-08-25	Procédé pour la préparation de dérivés de biphényle
DE2339240A1 (de)	1974-02-14	Metallextraktionsverfahren
CH642638A5 (de)	1984-04-30	Verfahren zur herstellung von chinazolin-2(1h)-onen.
DE69707860T2 (de)	2002-04-11	Verfahren zur herstellung von tetrahydroindolizinen
DE69119961T2 (de)	1996-11-28	Verfahren zur Reduzierung von Carbonyl enthaltendem Akridin
DE1932402C3 (de)	1981-09-03	1-Isopropyl-4-phenyl-3,4-dihydro-2(1H)chinazolinonderivate und deren Weiterverarbeitung zu 1-Isopropyl-4-phenyl-2(1H)chinazolinonen
DE1670032A1 (de)	1971-02-25	Neue 11-(Piperazinyl)-dibenz (b,f)(1,4)oxazepine und analoge -thiazepine
CH646971A5 (de)	1984-12-28	Dihalogen-substituierte anelierte pyrimidin-4-on-derivate und verfahren zu ihrer herstellung.
CH626347A5 (en)	1981-11-13	Process for the preparation of 4-hydroxy-2-quinolinone-3-carboxylic esters
US4171441A (en)	1979-10-16	Preparation of quinazolin-2(1H)-ones
DE2433176C3 (de)	1979-06-07	N-Cyano-cyano-acetimidate und Verfahren zur Herstellung von 2-Halopyrinüdinderivaten
DD249909A5 (de)	1987-09-23	Verfahren zur herstellung von carbocyclischen acetidin-3-saeuren und deren salzen
EP0030215A2 (fr)	1981-06-10	3,3,5-Trichloroglutarimide, procédé pour sa préparation et son utilisation pour la préparation de 2,3,5,6-tétrachloropyridine
DE3530061A1 (de)	1986-03-06	Verfahren zur herstellung von guanidinothiazolderivaten
KR820001716B1 (ko)	1982-09-21	4-아릴-퀴나졸린-2(1h)-온류의 제조방법
AT258916B (de)	1967-12-27	Verfahren zur Herstellung von neuen Alkyl-3-amino-5-chlor-6-X-pyrazinoaten
AT238209B (de)	1965-01-25	Verfahren zur Herstellung neuer 4-Oxo-1, 2, 3, 4-tetrahydro-chinazoline, deren Säureadditionssalzen und quaternären Ammoniumverbindungen
DE1770848A1 (de)	1972-03-09	Verfahren zur Herstellung von 3-Methansulfonylphenthiazinen
AT239786B (de)	1965-04-26	Verfahren zur Herstellung von neuen 3,6-disubstituierten 7-Sulfamylbenzo-1,1-dioxo-1-thia-2,4-diazinderivaten
AT258264B (de)	1967-11-10	Verfahren zur Herstellung von 5-(3'-Methylaminopropyl)-5H-dibenzo[a,d] cyclohepten
AT208866B (de)	1960-05-10	Verfahren zur Herstellung von neuen Phenthiazinverbindungen
DD246110A5 (de)	1987-05-27	Verfahren zur herstellung von 10 -methoxy-6-methylergolin-derivaten und ihren saeureadditionssalzen
DE2365755A1 (de)	1976-04-08	Alpha-ketosaeurederivate und verfahren zu ihrer herstellung