CS219282B2 - Method of making the 4-phenyl-2/ 1h/-chinazoline a-tetrahydro-21/1h/-chinazoline - Google Patents

Method of making the 4-phenyl-2/ 1h/-chinazoline a-tetrahydro-21/1h/-chinazoline Download PDF

Info

Publication number: CS219282B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; alkyl; compound; trifluoromethyl; compounds
Prior art date: 1979-07-05

Application number

CS804807A

Other languages

Czech (cs)

English (en)

Inventor

Peter Fufschilling

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.)

1979-07-05

Filing date

1980-07-04

Publication date

1983-03-25

1980-07-04 Application filed by Sandoz Ag filed Critical Sandoz Ag

1983-03-25 Publication of CS219282B2 publication Critical patent/CS219282B2/cs

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 8
230000007062 hydrolysis Effects 0.000 claims abstract description 5
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical class C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 51
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
125000000753 cycloalkyl group Chemical group 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
SDQJTWBNWQABLE-UHFFFAOYSA-N benzoylene urea Natural products C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 abstract description 3
238000003747 Grignard reaction Methods 0.000 abstract 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
150000003254 radicals Chemical class 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
-1 alkyl carbamates Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 3
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 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 description 2
239000000543 intermediate Substances 0.000 description 2
BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
ISKUTHMMLMPNFI-UHFFFAOYSA-N 3-methyl-n-propan-2-ylbut-2-en-1-imine Chemical compound CC(C)N=CC=C(C)C ISKUTHMMLMPNFI-UHFFFAOYSA-N 0.000 description 1
SMETZXVTVAOJNK-UHFFFAOYSA-N 4-(4-fluorophenyl)-7-methyl-1-propan-2-yl-4a,5,6,8a-tetrahydroquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2C=C(C)CCC2C=1C1=CC=C(F)C=C1 SMETZXVTVAOJNK-UHFFFAOYSA-N 0.000 description 1
RXPYIVMIOVRDTC-UHFFFAOYSA-N 4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2=CC=CC=C2C=1C1=CC=CC=C1 RXPYIVMIOVRDTC-UHFFFAOYSA-N 0.000 description 1
XBWNPWYUORIVAM-UHFFFAOYSA-N 7-methyl-1-propan-2-yl-4a,5,6,8a-tetrahydroquinazoline-2,4-dione Chemical compound C1=C(C)CCC2C(=O)NC(=O)N(C(C)C)C21 XBWNPWYUORIVAM-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
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 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000001316 cycloalkyl alkyl 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
239000012024 dehydrating agents‎ Substances 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
NLVYNZBDFVFSCX-UHFFFAOYSA-N methyl n-(6-cyano-3-methylcyclohex-2-en-1-yl)-n-propan-2-ylcarbamate Chemical compound COC(=O)N(C(C)C)C1C=C(C)CCC1C#N NLVYNZBDFVFSCX-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
125000006684 polyhaloalkyl group Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 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 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
239000012485 toluene extract Substances 0.000 description 1
FUCBQMFTYFQCOB-UHFFFAOYSA-N trityl perchlorate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCl(=O)(=O)=O)C1=CC=CC=C1 FUCBQMFTYFQCOB-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
- 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

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)
Quinoline Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Steroid Compounds (AREA)
Compounds Of Unknown Constitution (AREA)

CS804807A 1979-07-05 1980-07-04 Method of making the 4-phenyl-2/ 1h/-chinazoline a-tetrahydro-21/1h/-chinazoline CS219282B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH629879A CH645362A5 (de)	1979-07-05	1979-07-05	Verfahren zur herstellung von 4-phenyl-2(1h)-chinazolinonen.

Publications (1)

Publication Number	Publication Date
CS219282B2 true CS219282B2 (en)	1983-03-25

Family

ID=4307353

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS804807A CS219282B2 (en)	1979-07-05	1980-07-04	Method of making the 4-phenyl-2/ 1h/-chinazoline a-tetrahydro-21/1h/-chinazoline

Country Status (27)

Country	Link
US (1)	US4395550A (fr)
JP (1)	JPS5618968A (fr)
KR (1)	KR840002124B1 (fr)
AR (1)	AR227890A1 (fr)
AU (1)	AU544053B2 (fr)
BE (1)	BE884141A (fr)
CA (1)	CA1147730A (fr)
CH (1)	CH645362A5 (fr)
CS (1)	CS219282B2 (fr)
DE (1)	DE3022926A1 (fr)
DK (1)	DK291780A (fr)
ES (2)	ES493067A0 (fr)
FI (1)	FI802053A7 (fr)
FR (1)	FR2465726B1 (fr)
GB (1)	GB2055096B (fr)
HU (1)	HU188132B (fr)
IE (1)	IE50464B1 (fr)
IL (1)	IL60479A (fr)
IT (1)	IT1133033B (fr)
MA (1)	MA18896A1 (fr)
NL (1)	NL8003830A (fr)
NO (1)	NO802006L (fr)
NZ (1)	NZ194231A (fr)
PT (1)	PT71499B (fr)
SE (1)	SE8004923L (fr)
YU (1)	YU174680A (fr)
ZA (1)	ZA804056B (fr)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2217632A (en) *	1939-02-25	1940-10-08	Wingfoot Corp	Nitriles and method of preparing the same
BG16042A3 (bg) *	1968-11-12	1972-05-20	Nans Ott	Метод за получаване на нови 2(1н)-хиназолинони
DE2022470A1 (de) *	1970-05-08	1971-11-25	Entenmann Guenther Dipl Chem	Verfahren zur Herstellung halogensubstituierter 1.3-Diazaheterocyclen
JPS4821955B1 (fr) *	1970-12-11	1973-07-02
US3996227A (en) *	1971-07-08	1976-12-07	Sandoz, Inc.	7-Methyl-1-isopropyl-4-phenyl-5,6,7,8-tetrahydro-2(1H)-quinazolinone
DE2142317A1 (de) *	1971-08-24	1973-03-01	Bayer Ag	Hypnotisches mittel
NL7114936A (en) *	1971-10-29	1972-05-03		Quinazoline cpds - useful as analgesics and antipyretics
US3937705A (en) *	1972-03-09	1976-02-10	Sandoz, Inc.	1-isopropyl-7-methyl-4-(p-fluorophenyl)-2(1h)-quinazolinone
US4065496A (en) *	1976-01-07	1977-12-27	Chon Corporation	Trans-N-acyl-N-alkyl-1-amino-1,3-butadienes, trans-N-acyl-N-aryl-1-amino-1,3-butadienes and preparation thereof
US4171441A (en) *	1977-09-06	1979-10-16	Sandoz, Inc.	Preparation of quinazolin-2(1H)-ones
CH642638A5 (de) *	1977-09-06	1984-04-30	Sandoz Ag	Verfahren zur herstellung von chinazolin-2(1h)-onen.

1979
- 1979-07-05 CH CH629879A patent/CH645362A5/de not_active IP Right Cessation
1980
- 1980-06-19 DE DE19803022926 patent/DE3022926A1/de not_active Withdrawn
- 1980-06-27 FI FI802053A patent/FI802053A7/fi not_active Application Discontinuation
- 1980-07-02 NL NL8003830A patent/NL8003830A/nl not_active Application Discontinuation
- 1980-07-02 GB GB8021610A patent/GB2055096B/en not_active Expired
- 1980-07-03 NZ NZ194231A patent/NZ194231A/xx unknown
- 1980-07-03 CA CA000355388A patent/CA1147730A/fr not_active Expired
- 1980-07-03 HU HU801663A patent/HU188132B/hu unknown
- 1980-07-03 SE SE8004923A patent/SE8004923L/xx not_active Application Discontinuation
- 1980-07-03 NO NO802006A patent/NO802006L/no unknown
- 1980-07-03 IL IL60479A patent/IL60479A/xx unknown
- 1980-07-03 BE BE1/9876A patent/BE884141A/fr not_active IP Right Cessation
- 1980-07-03 YU YU01746/80A patent/YU174680A/xx unknown
- 1980-07-03 ES ES493067A patent/ES493067A0/es active Granted
- 1980-07-03 AU AU60084/80A patent/AU544053B2/en not_active Ceased
- 1980-07-04 PT PT71499A patent/PT71499B/pt unknown
- 1980-07-04 AR AR281668A patent/AR227890A1/es active
- 1980-07-04 IT IT49170/80A patent/IT1133033B/it active
- 1980-07-04 DK DK291780A patent/DK291780A/da not_active Application Discontinuation
- 1980-07-04 MA MA19094A patent/MA18896A1/fr unknown
- 1980-07-04 ZA ZA00804056A patent/ZA804056B/xx unknown
- 1980-07-04 IE IE1397/80A patent/IE50464B1/en unknown
- 1980-07-04 FR FR8014949A patent/FR2465726B1/fr not_active Expired
- 1980-07-04 JP JP9216280A patent/JPS5618968A/ja active Pending
- 1980-07-04 KR KR1019800002659A patent/KR840002124B1/ko not_active Expired
- 1980-07-04 CS CS804807A patent/CS219282B2/cs unknown
1981
- 1981-02-27 ES ES499901A patent/ES499901A0/es active Granted
- 1981-11-05 US US06/318,480 patent/US4395550A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AR227890A1 (es)	1982-12-30
PT71499A (en)	1980-08-01
IT1133033B (it)	1986-07-09
IE801397L (en)	1981-01-05
BE884141A (fr)	1981-01-05
GB2055096A (en)	1981-02-25
GB2055096B (en)	1983-11-23
DE3022926A1 (de)	1981-01-29
ES8205206A1 (es)	1982-06-01
DK291780A (da)	1981-01-06
KR840002124B1 (ko)	1984-11-19
IL60479A0 (en)	1980-09-16
IE50464B1 (en)	1986-04-30
ES8105718A1 (es)	1981-06-16
FR2465726B1 (fr)	1986-04-18
ZA804056B (en)	1982-02-24
AU544053B2 (en)	1985-05-16
FR2465726A1 (fr)	1981-03-27
NL8003830A (nl)	1981-01-07
CH645362A5 (de)	1984-09-28
ES493067A0 (es)	1981-06-16
HU188132B (en)	1986-03-28
NO802006L (no)	1981-01-06
PT71499B (en)	1981-08-11
FI802053A7 (fi)	1981-01-01
AU6008480A (en)	1981-01-15
CA1147730A (fr)	1983-06-07
YU174680A (en)	1983-09-30
KR830003438A (ko)	1983-06-20
ES499901A0 (es)	1982-06-01
SE8004923L (sv)	1981-01-06
IL60479A (en)	1986-01-31
US4395550A (en)	1983-07-26
JPS5618968A (en)	1981-02-23
IT8049170A0 (it)	1980-07-04
NZ194231A (en)	1983-06-14
MA18896A1 (fr)	1981-04-01

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JPS62234069A (ja)	1987-10-14	２―ピラゾリン―５―オン類の製造法
WO2006021974A1 (fr)	2006-03-02	Procede pour synthetiser un diol (viii), intermediaire du sodium de montelukast
EP0009384A1 (fr)	1980-04-02	Procédés de préparation de triazinones et de triazinones condensées, et les composés ainsi obtenus
US4803270A (en)	1989-02-07	Process of producing fluoroaniline derivatives
US4021469A (en)	1977-05-03	Process for preparing N-phenylcarbamates
SU591149A3 (ru)	1978-01-30	Способ получени производных триазолоизохинолина
US4634769A (en)	1987-01-06	Process for the preparation of 8-halo-5,6-dialkoxyquinazoline-2,4-diones and their salts
CS219282B2 (en)	1983-03-25	Method of making the 4-phenyl-2/ 1h/-chinazoline a-tetrahydro-21/1h/-chinazoline
US3910911A (en)	1975-10-07	Production of quinazolinone compounds
NO162342B (no)	1989-09-04	Fremgangsmaate ved fremstilling av beta-carboliner ved dehydrogenering.
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US4212804A (en)	1980-07-15	Process for the preparation of optionally substituted 2,3-indolinediones
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US5710319A (en)	1998-01-20	Process for the preparation of substituted quinazoline-2,4-diones
US3993660A (en)	1976-11-23	2-[3-(Phthalimidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzophenones
JPS5920676B2 (ja)	1984-05-15	新規なピリミド〔４，５−ｄ〕ピリミジン誘導体の製造法
SK115299A3 (en)	2000-01-18	Process for preparation of 4h-4-oxo-quinolizine-3-carboxylic acid derivatives