CH411910A - Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten - Google Patents
Verfahren zur Herstellung von 1,4-Benzodiazepin-DerivatenInfo
- Publication number
- CH411910A CH411910A CH1349060A CH1349060A CH411910A CH 411910 A CH411910 A CH 411910A CH 1349060 A CH1349060 A CH 1349060A CH 1349060 A CH1349060 A CH 1349060A CH 411910 A CH411910 A CH 411910A
- Authority
- CH
- Switzerland
- Prior art keywords
- halogen
- quinazoline
- hydrogen
- trifluoromethyl
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 5
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 8
- -1 nitro, amino Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- GZYBWMKOQXCCHC-UHFFFAOYSA-N (2-amino-5-methylsulfanylphenyl)-phenylmethanone Chemical compound CSC1=CC=C(N)C(C(=O)C=2C=CC=CC=2)=C1 GZYBWMKOQXCCHC-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
- AGPSBKMDGOYZKQ-UHFFFAOYSA-N 2-(chloromethyl)-3-oxido-4-phenyl-6-(trifluoromethyl)quinazolin-3-ium Chemical compound ClCC1=NC2=CC=C(C=C2C(=[N+]1[O-])C1=CC=CC=C1)C(F)(F)F AGPSBKMDGOYZKQ-UHFFFAOYSA-N 0.000 description 2
- KJYDELJAWGDQPO-UHFFFAOYSA-N 2-(chloromethyl)-6-nitro-3-oxido-4-phenylquinazolin-3-ium Chemical compound ClCC1=NC2=CC=C(C=C2C(=[N+]1[O-])C1=CC=CC=C1)[N+](=O)[O-] KJYDELJAWGDQPO-UHFFFAOYSA-N 0.000 description 2
- LCISFYAQKHOWBP-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(Cl)C(C#N)=C1 LCISFYAQKHOWBP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- MXIQGSGGDKPJFE-UHFFFAOYSA-N Cl.ClC1=C(C(C2=CC=CC=C2)=N)C=C(C=C1)C(F)(F)F Chemical compound Cl.ClC1=C(C(C2=CC=CC=C2)=N)C=C(C=C1)C(F)(F)F MXIQGSGGDKPJFE-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- AVPYVFOHLZKIET-UHFFFAOYSA-N N-[[2-amino-5-(trifluoromethyl)phenyl]-phenylmethylidene]hydroxylamine Chemical compound NC1=C(C(C2=CC=CC=C2)=NO)C=C(C=C1)C(F)(F)F AVPYVFOHLZKIET-UHFFFAOYSA-N 0.000 description 2
- NRMOBHGSHDKJLW-UHFFFAOYSA-N [2-amino-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 NRMOBHGSHDKJLW-UHFFFAOYSA-N 0.000 description 2
- QHDJJBSLUFDASY-UHFFFAOYSA-N [2-chloro-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 QHDJJBSLUFDASY-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- ONHUMNWRIVWZHH-UHFFFAOYSA-N n-[(2-amino-5-nitrophenyl)-phenylmethylidene]hydroxylamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=NO)C1=CC=CC=C1 ONHUMNWRIVWZHH-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003246 quinazolines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 description 1
- WWEHKSOZUNFOMP-UHFFFAOYSA-N (4-amino-3-benzoylphenyl) thiocyanate Chemical compound NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)SC#N WWEHKSOZUNFOMP-UHFFFAOYSA-N 0.000 description 1
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- NLHOVYMVGLRDPF-UHFFFAOYSA-N 1-oxidoquinazolin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CN=CC2=C1 NLHOVYMVGLRDPF-UHFFFAOYSA-N 0.000 description 1
- WFFWEEOVGFHGGZ-UHFFFAOYSA-N 2-(chloromethyl)-6-methyl-3-oxido-4-phenylquinazolin-3-ium Chemical compound C12=CC(C)=CC=C2N=C(CCl)[N+]([O-])=C1C1=CC=CC=C1 WFFWEEOVGFHGGZ-UHFFFAOYSA-N 0.000 description 1
- VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 1
- TWMCPKMLXDZUQU-UHFFFAOYSA-N 2-methyl-3-oxidoquinazolin-3-ium Chemical compound C1=CC=C2C=[N+]([O-])C(C)=NC2=C1 TWMCPKMLXDZUQU-UHFFFAOYSA-N 0.000 description 1
- LFILBRVANBXLHX-UHFFFAOYSA-N 6-bromo-2-(chloromethyl)-3-oxido-4-phenylquinazolin-3-ium Chemical compound [O-][N+]1=C(CCl)N=C2C=CC(Br)=CC2=C1C1=CC=CC=C1 LFILBRVANBXLHX-UHFFFAOYSA-N 0.000 description 1
- HRFMKWKILQFPCB-UHFFFAOYSA-N 6-chloro-2-(chloromethyl)-3-oxido-4-phenylquinazolin-3-ium;hydrochloride Chemical compound Cl.[O-][N+]1=C(CCl)N=C2C=CC(Cl)=CC2=C1C1=CC=CC=C1 HRFMKWKILQFPCB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OHNISMFYEZSZNG-UHFFFAOYSA-N BrC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=C(C=C2)C)C1 Chemical compound BrC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=C(C=C2)C)C1 OHNISMFYEZSZNG-UHFFFAOYSA-N 0.000 description 1
- MCTYNVDBNGNARP-UHFFFAOYSA-N CC=1C(=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1)C Chemical compound CC=1C(=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1)C MCTYNVDBNGNARP-UHFFFAOYSA-N 0.000 description 1
- SYYDSEGZZPPCRG-UHFFFAOYSA-N CSC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1 Chemical compound CSC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1 SYYDSEGZZPPCRG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KTJBKMAOHBRUTF-UHFFFAOYSA-N ClC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=C(C=C2)Cl)C1 Chemical compound ClC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=C(C=C2)Cl)C1 KTJBKMAOHBRUTF-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- LOTYFHMCWDVECI-UHFFFAOYSA-N N-[(2-amino-5-methylsulfanylphenyl)-phenylmethylidene]hydroxylamine Chemical compound NC1=C(C(C2=CC=CC=C2)=NO)C=C(C=C1)SC LOTYFHMCWDVECI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- RXBKPDNCXZSXJM-UHFFFAOYSA-N [N+](=O)([O-])C=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1 Chemical compound [N+](=O)([O-])C=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1 RXBKPDNCXZSXJM-UHFFFAOYSA-N 0.000 description 1
- OJDGPERBKOETAX-UHFFFAOYSA-N [O-][N+]1=C(c2ccccc2Cl)c2cc(Cl)ccc2NC(=O)C1 Chemical compound [O-][N+]1=C(c2ccccc2Cl)c2cc(Cl)ccc2NC(=O)C1 OJDGPERBKOETAX-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 239000003054 catalyst Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- HQNIJHRMGXERBP-UHFFFAOYSA-N chembl1611846 Chemical compound C12=CC(Br)=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1 HQNIJHRMGXERBP-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 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
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- 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
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80983A US3336295A (en) | 1960-12-02 | 1961-01-06 | Hydroxy or alkoxy substituted 5-phenyl-3h-1, 4-benzodiazepin-2(1h)-ones |
| US149527A US3136815A (en) | 1959-12-10 | 1961-11-02 | Amino substituted benzophenone oximes and derivatives thereof |
| US154921A US3371085A (en) | 1959-12-10 | 1961-11-20 | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
| US502510A US3344183A (en) | 1960-12-02 | 1965-10-22 | 2 n-substituted amino benzophenones |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85856459A | 1959-12-10 | 1959-12-10 | |
| US260560A | 1960-01-15 | 1960-01-15 | |
| US2468660A | 1960-04-26 | 1960-04-26 | |
| US3873260A | 1960-06-27 | 1960-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH411910A true CH411910A (de) | 1966-04-30 |
Family
ID=27485190
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1349060A CH411910A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1349360A CH418342A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepinen |
| CH1349460A CH414652A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1349560A CH414653A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1349260A CH418341A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepinen |
| CH1349160A CH408029A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepinen |
| CH1230565A CH408045A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von Benzophenonderivaten |
| CH1348960A CH408940A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1389960A CH396016A (de) | 1959-12-10 | 1960-12-13 | Verfahren zur Herstellung von fluorhaltigen Benzodiazepinen |
Family Applications After (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1349360A CH418342A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepinen |
| CH1349460A CH414652A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1349560A CH414653A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1349260A CH418341A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepinen |
| CH1349160A CH408029A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepinen |
| CH1230565A CH408045A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von Benzophenonderivaten |
| CH1348960A CH408940A (de) | 1959-12-10 | 1960-12-02 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
| CH1389960A CH396016A (de) | 1959-12-10 | 1960-12-13 | Verfahren zur Herstellung von fluorhaltigen Benzodiazepinen |
Country Status (11)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795231C3 (de) * | 1963-05-29 | 1978-07-13 | American Home Products Corp., New York, N.Y. (V.St.A.) | Verfahren zur Herstellung von 5-Aryl-1,2-dihydro -3H-1,4-benzodiazepin-2-on-4-oxyden |
| GB1333501A (en) * | 1971-03-05 | 1973-10-10 | Ravizza Spa | Process for the preparation of 7-chlorobenzodiazepine de rivatives |
| US4820834A (en) * | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| CA1332410C (en) * | 1984-06-26 | 1994-10-11 | Roger M. Freidinger | Benzodiazepine analogs |
| JP2005503356A (ja) | 2001-06-07 | 2005-02-03 | ニューロ３デー | 環状ヌクレオチドホスホジエステラーゼ阻害剤、その製造および使用 |
| CA2784937A1 (en) * | 2002-05-24 | 2003-12-04 | Millennium Pharmaceuticals, Inc. | Ccr9 inhibitors and methods of use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2893992A (en) * | 1959-07-07 | I ii i i |
-
1960
- 1960-12-02 CH CH1349060A patent/CH411910A/de unknown
- 1960-12-02 CH CH1349360A patent/CH418342A/de unknown
- 1960-12-02 CH CH1349460A patent/CH414652A/de unknown
- 1960-12-02 CH CH1349560A patent/CH414653A/de unknown
- 1960-12-02 CH CH1349260A patent/CH418341A/de unknown
- 1960-12-02 CH CH1349160A patent/CH408029A/de unknown
- 1960-12-02 CH CH1230565A patent/CH408045A/de unknown
- 1960-12-02 CH CH1348960A patent/CH408940A/de unknown
- 1960-12-07 DE DEH41138A patent/DE1290143B/de active Pending
- 1960-12-07 DE DEH41137A patent/DE1288609B/de active Pending
- 1960-12-07 DE DEH41139A patent/DE1288610B/de active Pending
- 1960-12-07 BR BR124755/60A patent/BR6024755D0/pt unknown
- 1960-12-09 GB GB42401/60A patent/GB972963A/en not_active Expired
- 1960-12-09 ES ES0263123A patent/ES263123A1/es not_active Expired
- 1960-12-09 GB GB20071/63A patent/GB972976A/en not_active Expired
- 1960-12-09 BE BE598012A patent/BE598012A/fr unknown
- 1960-12-09 BE BE598013A patent/BE598013A/fr unknown
- 1960-12-09 BE BE598015A patent/BE598015A/fr unknown
- 1960-12-09 GB GB42408/60A patent/GB972968A/en not_active Expired
- 1960-12-09 GB GB42404/60A patent/GB972966A/en not_active Expired
- 1960-12-09 BE BE598008A patent/BE598008A/fr unknown
- 1960-12-09 GB GB42402/60A patent/GB972964A/en not_active Expired
- 1960-12-09 GB GB42400/60A patent/GB972962A/en not_active Expired
- 1960-12-09 GB GB40979/62A patent/GB972973A/en not_active Expired
- 1960-12-09 GB GB42399/60A patent/GB972961A/en not_active Expired
- 1960-12-09 GB GB42405/60A patent/GB972967A/en not_active Expired
- 1960-12-09 ES ES0263124A patent/ES263124A1/es not_active Expired
- 1960-12-09 GB GB40978/62A patent/GB972972A/en not_active Expired
- 1960-12-09 GB GB42403/60A patent/GB972965A/en not_active Expired
- 1960-12-13 CH CH1389960A patent/CH396016A/de unknown
- 1960-12-19 DE DE19601445073 patent/DE1445073A1/de active Pending
-
1961
- 1961-01-11 GB GB1168/61A patent/GB972969A/en not_active Expired
- 1961-01-11 GB GB29834/62A patent/GB972970A/en not_active Expired
-
1964
- 1964-09-10 DE DE19641445908 patent/DE1445908A1/de active Pending
- 1964-10-21 NL NL6412251A patent/NL6412251A/xx unknown
- 1964-10-21 NL NL6412250A patent/NL6412250A/xx unknown
- 1964-12-16 OA OA50896A patent/OA00817A/xx unknown
- 1964-12-16 OA OA50895A patent/OA00816A/xx unknown
- 1964-12-26 OA OA51048A patent/OA00953A/xx unknown
- 1964-12-26 OA OA51053A patent/OA00958A/xx unknown
- 1964-12-26 OA OA51054A patent/OA00959A/xx unknown
-
1965
- 1965-09-17 SE SE12149/65A patent/SE310887B/xx unknown
- 1965-11-03 CY CY32465A patent/CY324A/xx unknown
- 1965-12-31 MY MY1965178A patent/MY6500178A/xx unknown
-
1967
- 1967-03-30 OA OA52850A patent/OA02385A/xx unknown
- 1967-03-30 OA OA52849A patent/OA02384A/xx unknown
- 1967-11-15 SE SE1570567A patent/SE318283B/xx unknown
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