FI58639C - Foerfarande foer framstaellning av kinazolinonderivat - Google Patents
Foerfarande foer framstaellning av kinazolinonderivat Download PDFInfo
- Publication number
- FI58639C FI58639C FI2282/73A FI228273A FI58639C FI 58639 C FI58639 C FI 58639C FI 2282/73 A FI2282/73 A FI 2282/73A FI 228273 A FI228273 A FI 228273A FI 58639 C FI58639 C FI 58639C
- Authority
- FI
- Finland
- Prior art keywords
- quinazolinone
- group
- phenyl
- chloro
- solution
- Prior art date
Links
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000013078 crystal Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- DCANGVYZWYRVOB-UHFFFAOYSA-N 2-amino-2-oxoacetyl chloride Chemical compound NC(=O)C(Cl)=O DCANGVYZWYRVOB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000006105 Hofmann reaction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XVRMPRSFJVHCKC-UHFFFAOYSA-N 1-(2-chlorophenyl)-6-nitroquinazolin-2-one Chemical compound ClC1=C(C=CC=C1)N1C(N=CC2=CC(=CC=C12)[N+](=O)[O-])=O XVRMPRSFJVHCKC-UHFFFAOYSA-N 0.000 description 1
- RLWCBNUYDMVYDZ-UHFFFAOYSA-N 1-methyl-5-nitro-3-phenylindole-2-carboxamide Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(C(N)=O)=C1C1=CC=CC=C1 RLWCBNUYDMVYDZ-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
- 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 1
- VBLPVYUNPGIAJN-UHFFFAOYSA-N 6-bromo-1-(cyclopropylmethyl)-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(Br)=CC=C2N1CC1CC1 VBLPVYUNPGIAJN-UHFFFAOYSA-N 0.000 description 1
- UWBMJRNZYZVMRI-UHFFFAOYSA-N 6-chloro-1-phenylquinazolin-2-one Chemical compound O=C1N=CC2=CC(Cl)=CC=C2N1C1=CC=CC=C1 UWBMJRNZYZVMRI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RHLFJUCLCJVOCL-UHFFFAOYSA-N C(C)(=O)OC(C)C1=NC(N(C2=CC=C(C=C12)Cl)C1=CC=CC=C1)=O Chemical compound C(C)(=O)OC(C)C1=NC(N(C2=CC=C(C=C12)Cl)C1=CC=CC=C1)=O RHLFJUCLCJVOCL-UHFFFAOYSA-N 0.000 description 1
- OBYZNUAMHPTBKP-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1C(C=CC=C1)(Cl)N(C(=O)C(=O)N)C Chemical compound C(C1=CC=CC=C1)(=O)C1C(C=CC=C1)(Cl)N(C(=O)C(=O)N)C OBYZNUAMHPTBKP-UHFFFAOYSA-N 0.000 description 1
- PWRXWSXLDFNTKE-UHFFFAOYSA-N C1(CC1)C(C)C1=NC(N(C2=CC=C(C=C12)Cl)C1=CC=CC=C1)=O Chemical compound C1(CC1)C(C)C1=NC(N(C2=CC=C(C=C12)Cl)C1=CC=CC=C1)=O PWRXWSXLDFNTKE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VICJELFWVUZRDU-UHFFFAOYSA-N ClC1=C(C=CC=C1)N1C(N=CC2=CC(=CC=C12)Cl)=O Chemical compound ClC1=C(C=CC=C1)N1C(N=CC2=CC(=CC=C12)Cl)=O VICJELFWVUZRDU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- IIIURPXTBCZMAI-UHFFFAOYSA-N N'-(2-benzoyl-4-chlorophenyl)-N'-methyloxamide Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=CC(=C1)Cl)N(C(=O)C(=O)N)C IIIURPXTBCZMAI-UHFFFAOYSA-N 0.000 description 1
- KQGIXKRZIYGRJZ-UHFFFAOYSA-N N'-(6-benzoyl-1-chlorocyclohexa-2,4-dien-1-yl)-N'-(cyclopropylmethyl)oxamide Chemical compound C(C1=CC=CC=C1)(=O)C1C(C=CC=C1)(Cl)N(C(=O)C(=O)N)CC1CC1 KQGIXKRZIYGRJZ-UHFFFAOYSA-N 0.000 description 1
- RKPVYOXUCBKXAW-UHFFFAOYSA-N N(C(=O)C(=O)N)C1(C(C=CC=C1)C(C1=CC=CC=C1)=O)Cl Chemical compound N(C(=O)C(=O)N)C1(C(C=CC=C1)C(C1=CC=CC=C1)=O)Cl RKPVYOXUCBKXAW-UHFFFAOYSA-N 0.000 description 1
- FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- WCRKZICZCPHVAB-UHFFFAOYSA-N [5-chloro-2-(cyclopropylmethylamino)phenyl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NCC1CC1 WCRKZICZCPHVAB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7325072A JPS5418269B2 (is") | 1972-07-20 | 1972-07-20 | |
| JP7325072 | 1972-07-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58639B FI58639B (fi) | 1980-11-28 |
| FI58639C true FI58639C (fi) | 1981-03-10 |
Family
ID=13512732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2282/73A FI58639C (fi) | 1972-07-20 | 1973-07-19 | Foerfarande foer framstaellning av kinazolinonderivat |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3910911A (is") |
| JP (1) | JPS5418269B2 (is") |
| AT (1) | AT329570B (is") |
| CA (1) | CA949574A (is") |
| CH (1) | CH585730A5 (is") |
| DK (1) | DK132430C (is") |
| FI (1) | FI58639C (is") |
| HU (1) | HU166497B (is") |
| NL (1) | NL7310055A (is") |
| PL (1) | PL91618B1 (is") |
| SE (1) | SE400281B (is") |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4202895A (en) * | 1971-06-04 | 1980-05-13 | Sumitomo Chemical Company, Limited | 1-Polyhaloalkyl-2(1H)-quinazolinone derivatives |
| US3988300A (en) * | 1973-05-31 | 1976-10-26 | American Cyanamid Company | Benzophenone ureas and method for utilizing the same |
| CA1114373A (en) * | 1978-08-11 | 1981-12-15 | Albert E. Fischli | Benzodiazepine derivatives |
| US5312820A (en) * | 1992-07-17 | 1994-05-17 | Merck & Co., Inc. | Substituted carbamoyl and oxycarbonyl derivatives of biphenylmethylamines |
| AR038658A1 (es) * | 2001-06-15 | 2005-01-26 | Novartis Ag | Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento |
| GB0230015D0 (en) * | 2002-12-23 | 2003-01-29 | Novartis Ag | Organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2037693C3 (de) * | 1969-08-02 | 1975-01-16 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 1-Cyclopropylmethyl-2(1 H)-chinazolinonderivate |
-
1972
- 1972-07-20 JP JP7325072A patent/JPS5418269B2/ja not_active Expired
-
1973
- 1973-07-10 CA CA176,081A patent/CA949574A/en not_active Expired
- 1973-07-10 DK DK383573A patent/DK132430C/da not_active IP Right Cessation
- 1973-07-12 US US378555A patent/US3910911A/en not_active Expired - Lifetime
- 1973-07-18 CH CH1052573A patent/CH585730A5/xx not_active IP Right Cessation
- 1973-07-19 NL NL7310055A patent/NL7310055A/xx not_active Application Discontinuation
- 1973-07-19 PL PL1973164172A patent/PL91618B1/pl unknown
- 1973-07-19 AT AT637373A patent/AT329570B/de not_active IP Right Cessation
- 1973-07-19 SE SE7310099A patent/SE400281B/xx unknown
- 1973-07-19 FI FI2282/73A patent/FI58639C/fi active
- 1973-07-20 HU HUSU827A patent/HU166497B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE400281B (sv) | 1978-03-20 |
| ATA637373A (de) | 1975-08-15 |
| NL7310055A (is") | 1974-01-22 |
| CA949574A (en) | 1974-06-18 |
| AT329570B (de) | 1976-05-25 |
| DK132430B (da) | 1975-12-08 |
| DK132430C (da) | 1976-05-03 |
| CH585730A5 (is") | 1977-03-15 |
| JPS5418269B2 (is") | 1979-07-06 |
| FI58639B (fi) | 1980-11-28 |
| PL91618B1 (is") | 1977-03-31 |
| US3910911A (en) | 1975-10-07 |
| HU166497B (is") | 1975-03-28 |
| JPS4931680A (is") | 1974-03-22 |
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