EP0000148A1 - Chinazolinon-3-Oxyd-derivate und Verfahren zu ihrer Herstellung - Google Patents
Chinazolinon-3-Oxyd-derivate und Verfahren zu ihrer Herstellung Download PDFInfo
- Publication number
- EP0000148A1 EP0000148A1 EP78100162A EP78100162A EP0000148A1 EP 0000148 A1 EP0000148 A1 EP 0000148A1 EP 78100162 A EP78100162 A EP 78100162A EP 78100162 A EP78100162 A EP 78100162A EP 0000148 A1 EP0000148 A1 EP 0000148A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- compound
- quinazolinone
- oxide
- chloro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 5
- FTAHQVWNRWZINV-UHFFFAOYSA-N 1-hydroxyquinazolin-2-one Chemical class C1=CC=C2C=NC(=O)N(O)C2=C1 FTAHQVWNRWZINV-UHFFFAOYSA-N 0.000 title abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 31
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 26
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000000460 chlorine Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 8
- -1 alkali metal salt Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910005143 FSO2 Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 3
- 229940035363 muscle relaxants Drugs 0.000 abstract description 2
- 239000003158 myorelaxant agent Substances 0.000 abstract description 2
- 229940125723 sedative agent Drugs 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 239000003204 tranquilizing agent Substances 0.000 abstract description 2
- 230000002936 tranquilizing effect Effects 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 7
- PIKZXHWPRIJZJN-UHFFFAOYSA-N 6-chloro-1-methyl-3-oxido-4-phenylquinazolin-3-ium-2-one Chemical compound [O-][N+]=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 PIKZXHWPRIJZJN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PFNXVIDDDAFQRQ-UHFFFAOYSA-N C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 PFNXVIDDDAFQRQ-UHFFFAOYSA-N 0.000 description 4
- AGKPGIOZNCJFTQ-UHFFFAOYSA-N [2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 AGKPGIOZNCJFTQ-UHFFFAOYSA-N 0.000 description 4
- WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ODHUYTANXZSDAG-UHFFFAOYSA-N 6-bromo-1-methyl-3-oxido-4-phenylquinazolin-3-ium-2-one Chemical compound [O-][N+]=1C(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 ODHUYTANXZSDAG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- XEZLUZCIJOCNSK-UHFFFAOYSA-N 1-methyl-3-oxidoquinazolin-3-ium-2-one Chemical class C1=CC=C2C=[N+]([O-])C(=O)N(C)C2=C1 XEZLUZCIJOCNSK-UHFFFAOYSA-N 0.000 description 2
- PZOZHMBWLDUJCP-UHFFFAOYSA-N 3-fluoro-1H-1,2-benzodiazepine Chemical class FC1=NNC2=C(C=C1)C=CC=C2 PZOZHMBWLDUJCP-UHFFFAOYSA-N 0.000 description 2
- ZXBWHSQNFXUCLP-UHFFFAOYSA-N C1=CC=C2NC(=O)[N+]([O-])=CC2=C1 Chemical class C1=CC=C2NC(=O)[N+]([O-])=CC2=C1 ZXBWHSQNFXUCLP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- XHPPBGZNBZMKNH-UHFFFAOYSA-N 1,2-dihydro-1,2-benzodiazepin-3-one Chemical compound C1=CC(O)=NNC2=CC=CC=C21 XHPPBGZNBZMKNH-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- JSBDUFBKBJIINE-UHFFFAOYSA-N 1-methyl-1-oxidoquinazolin-1-ium-2-one Chemical class C1=CC=C2[N+](C)([O-])C(=O)N=CC2=C1 JSBDUFBKBJIINE-UHFFFAOYSA-N 0.000 description 1
- FAIIZNBFZSTERU-UHFFFAOYSA-N 1-methyl-3-oxido-2h-quinazolin-3-ium Chemical class C1=CC=C2N(C)C[N+]([O-])=CC2=C1 FAIIZNBFZSTERU-UHFFFAOYSA-N 0.000 description 1
- NLHOVYMVGLRDPF-UHFFFAOYSA-N 1-oxidoquinazolin-1-ium Chemical class C1=CC=C2[N+]([O-])=CN=CC2=C1 NLHOVYMVGLRDPF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JRTXZECHXRHMEP-UHFFFAOYSA-N C12=CC(Br)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Br)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 JRTXZECHXRHMEP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
Definitions
- starting material (1) can be prepared by the process disclosed in U.S. Patent No. 3,398,139.
- the present invention relates to an improved process for making such N-methylaminobenzophenone anti-oximes, and novel intermediates used in the improved process.
- the present invention relates to a new process for the preparation of N-methylaminobenzophenone anti-oximes by alkylation, and subsequent hydrolysis, of the corresponding quinazoline oxides.
- the preparation of compounds of Formula III is accomplished in two interrelated stages.
- reaction products of Formula II (X, Y as defined) are then hydrolytically converted in the presence of base to the methylaminobenzophenone anti-oximes of Formula III (X, Y as defined).
- compounds of formula II which are preferred as intermediates are those where X is chlorine or bromine. More preferred compounds of formula II are those where X is chlorine or bromine and Y is hydrogen, chlorine or fluorine.
- Most preferred compounds are those where X is chlorine or bromine and Y is hydrogen or fluorine.
- 1-Methylquinazolinone oxides of Formula II can be prepared by treating a solution or mixture of a compound of Formula I, prepared as taught by Sulkowski and Childress, J. Org. Chem., 27 4424 (1962) or by the improved process disclosed by Middleton in copending U.S. Patent Application Serial Number filed simultaneously herewith (attorney's docket number CR-7794), and a suitable base with an alkylating agent in an inert organic solvent medium.
- the reaction is preferentially carried out at moderate temperatures of 50-75°, but this step can be effected at room temperature.or above.
- Suitable solvents include, but are not limited to, ethers such as tetrahydrofuran,.diethyl ether and glyme; amides of secondary amines such as N,N-dimethylformamide and N,N-dimethylacetamide.
- Representative bases useful in the generation of the alkali metal salt of a compound of Formula I include, but are not limited to, potassium carbonate, sodium hydride, sodium carbonate and sodium or potassium alkoxides such as sodium ethoxide or methoxide.
- the alkylated quinazolinone oxides can be isolated from the reaction mixture by conventional means, such as filtration of the insoluble product.
- the compound of Formula II can then be converted to the anti-oxime by heating with a base in an aqueous- alcoholic solvent.
- a base in an aqueous- alcoholic solvent.
- the reaction is conveniently carried out at the reflux temperature of the solvent.
- Useful alcoholic solvents include, but are not limited to, ethanol, methanol, propanol, isopropanol, butanol, 2-methoxyethanol, ethylene glycol and propylene glycol.
- suitable bases are alkali metal (such as sodium and potassium) hydroxides, carbonates and bicarbonates.
- the alkylaminobenzophenone anti-oximes obtained can be purified by evaporation of the reaction solvent and recrystallization of the solid residue.
- the yellow solid was dissolved in 350 ml of hot 1-chlorobutane. This hot viscous solution was filtered through a coarse fritted glass funnel. The filter and empty flask were thoroughly rinsed with exactly 150 ml of 1-chlorobutane and added to the filtrate. A total of only 500 ml of 1-chlorobutane was used. On addition of 2,000 ml of hexane to the chlorobutane solution, the desired product precipitated out.
- the anti-5-chloro-2-(N-methylamino)benzophenone oxime was obtained either in 88% yield (crystalline form "a", m.p. 90-91°) or 80% yield (crystalline form "b", m.p.
- the anti-oxime obtained exists in two different crystalline modifications. Their solid infrared spectra differ, as do color and solubility. The least soluble crystalline form, "a” precipitates out immediately on addition of hexane to the 1-chlorobutane solution. It is quite yellow, fluffy and obtained in good yield. The crystalline form "b” is more soluble and is obtained when hexane addition does not cause rapid precipitation, but rather a slow crystallization which requires thorough cooling. The material is pale yellow and crystalline.
- Table I shows additional 1-methylquinazolinone 3-oxides that can be prepared by the processes disclosed and illustrated above using the appropriate quinazolinone 3-oxide and a suitable methylating agent.
- Table II shows additional methylaminobenzophenone anti-oximes that can be prepared by the processes disclosed and illustrated above using the appropriate 1-methylquinazolinone 3-oxide and a suitable base.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/807,074 US4160092A (en) | 1977-06-16 | 1977-06-16 | Quinazolinone oxides and their use as intermediates for pharmaceutical agents |
| US807074 | 2007-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0000148A1 true EP0000148A1 (de) | 1979-01-10 |
Family
ID=25195499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100162A Withdrawn EP0000148A1 (de) | 1977-06-16 | 1978-06-15 | Chinazolinon-3-Oxyd-derivate und Verfahren zu ihrer Herstellung |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4160092A (de) |
| EP (1) | EP0000148A1 (de) |
| JP (1) | JPS545989A (de) |
| AR (1) | AR218668A1 (de) |
| AT (1) | AT359057B (de) |
| AU (1) | AU3713878A (de) |
| DK (1) | DK176478A (de) |
| ES (1) | ES470829A1 (de) |
| FI (1) | FI781929A7 (de) |
| GR (1) | GR64974B (de) |
| IL (1) | IL54922A0 (de) |
| IT (1) | IT1098333B (de) |
| NO (1) | NO782086L (de) |
| NZ (1) | NZ187582A (de) |
| PT (1) | PT68173A (de) |
| SU (1) | SU731893A3 (de) |
| ZA (1) | ZA783440B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5684735U (de) * | 1979-12-03 | 1981-07-08 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754246A (en) * | 1970-07-31 | 1970-12-31 | Sumitomo Chemical Co | Novel quinazoline derivs prepn |
| CH573412A5 (en) * | 1971-08-17 | 1976-03-15 | Sumitomo Chemical Co | 1-substd 4-aryl-2(1h) quinazolinones - anti-inflammatories, analgesics, uricosurics, andantivirals |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BG16042A3 (bg) * | 1968-11-12 | 1972-05-20 | Nans Ott | Метод за получаване на нови 2(1н)-хиназолинони |
-
1977
- 1977-06-16 US US05/807,074 patent/US4160092A/en not_active Expired - Lifetime
-
1978
- 1978-04-24 DK DK176478A patent/DK176478A/da not_active Application Discontinuation
- 1978-06-09 AR AR272533A patent/AR218668A1/es active
- 1978-06-15 ES ES470829A patent/ES470829A1/es not_active Expired
- 1978-06-15 ZA ZA00783440A patent/ZA783440B/xx unknown
- 1978-06-15 PT PT68173A patent/PT68173A/pt unknown
- 1978-06-15 AU AU37138/78A patent/AU3713878A/en active Pending
- 1978-06-15 EP EP78100162A patent/EP0000148A1/de not_active Withdrawn
- 1978-06-15 NO NO782086A patent/NO782086L/no unknown
- 1978-06-15 IL IL7854922A patent/IL54922A0/xx unknown
- 1978-06-15 AT AT436778A patent/AT359057B/de not_active IP Right Cessation
- 1978-06-15 IT IT24614/78A patent/IT1098333B/it active
- 1978-06-15 NZ NZ187582A patent/NZ187582A/xx unknown
- 1978-06-16 FI FI781929A patent/FI781929A7/fi not_active Application Discontinuation
- 1978-06-16 GR GR56540A patent/GR64974B/el unknown
- 1978-06-16 SU SU782626798A patent/SU731893A3/ru active
- 1978-06-16 JP JP7368078A patent/JPS545989A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754246A (en) * | 1970-07-31 | 1970-12-31 | Sumitomo Chemical Co | Novel quinazoline derivs prepn |
| CH573412A5 (en) * | 1971-08-17 | 1976-03-15 | Sumitomo Chemical Co | 1-substd 4-aryl-2(1h) quinazolinones - anti-inflammatories, analgesics, uricosurics, andantivirals |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS545989A (en) | 1979-01-17 |
| IL54922A0 (en) | 1978-08-31 |
| US4160092A (en) | 1979-07-03 |
| ES470829A1 (es) | 1979-10-01 |
| IT1098333B (it) | 1985-09-07 |
| DK176478A (da) | 1978-12-17 |
| ATA436778A (de) | 1980-03-15 |
| NZ187582A (en) | 1980-11-28 |
| AU3713878A (en) | 1979-12-20 |
| SU731893A3 (ru) | 1980-04-30 |
| GR64974B (en) | 1980-06-11 |
| PT68173A (en) | 1978-07-01 |
| IT7824614A0 (it) | 1978-06-15 |
| FI781929A7 (fi) | 1978-12-17 |
| AR218668A1 (es) | 1980-06-30 |
| ZA783440B (en) | 1979-06-27 |
| AT359057B (de) | 1980-10-27 |
| NO782086L (no) | 1978-12-19 |
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