SU472505A3 - Способ получени производных диазепина - Google Patents
Способ получени производных диазепинаInfo
- Publication number
- SU472505A3 SU472505A3 SU1813891A SU1813891A SU472505A3 SU 472505 A3 SU472505 A3 SU 472505A3 SU 1813891 A SU1813891 A SU 1813891A SU 1813891 A SU1813891 A SU 1813891A SU 472505 A3 SU472505 A3 SU 472505A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- acid
- triazolo
- ester
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 title claims 2
- -1 methanesulfonic acid ester Chemical class 0.000 claims description 33
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005277 alkyl imino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000004494 ethyl ester group Chemical group 0.000 description 13
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- PHNMUQYFHNMYGN-UHFFFAOYSA-N 1h-1,4-benzodiazepine-2-carboxylic acid Chemical compound N1C(C(=O)O)=CN=CC2=CC=CC=C21 PHNMUQYFHNMYGN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 229940049706 benzodiazepine Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- GPOKFLSWUBGZBM-UHFFFAOYSA-N 1,2-benzodiazepine-2-carboxylic acid Chemical compound OC(=O)N1C=CC=C2C=CC=CC2=N1 GPOKFLSWUBGZBM-UHFFFAOYSA-N 0.000 description 2
- LERNPNYCRHZBDL-UHFFFAOYSA-N 2-[(2-chloroacetyl)amino]propanedioic acid Chemical compound OC(=O)C(C(O)=O)NC(=O)CCl LERNPNYCRHZBDL-UHFFFAOYSA-N 0.000 description 2
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LXJVUGANBDAASB-UHFFFAOYSA-N (2-amino-5-bromophenyl)-phenylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 LXJVUGANBDAASB-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
- RZMGZEJEAAVXRG-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxylic acid Chemical compound N1NN(C=C1)C(=O)O RZMGZEJEAAVXRG-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- BDMLDWKLIAIPFN-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BDMLDWKLIAIPFN-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 1
- XDSFEVFCNJALNV-WLHGVMLRSA-N 1h-1,2-benzodiazepine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N1N=CC=CC2=CC=CC=C12 XDSFEVFCNJALNV-WLHGVMLRSA-N 0.000 description 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- FDSBQUURQHFJEA-UHFFFAOYSA-N diethyl 2-[(2-chloroacetyl)amino]-2-[[2-(2-chlorobenzoyl)phenyl]diazenyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(NC(CCl)=O)N=NC1=C(C=CC=C1)C(C1=C(C=CC=C1)Cl)=O)=O FDSBQUURQHFJEA-UHFFFAOYSA-N 0.000 description 1
- AXWHLJPTWDPRRN-UHFFFAOYSA-N diethyl 2-[(2-chloroacetyl)amino]-2-[[4-chloro-2-(2-chlorobenzoyl)phenyl]diazenyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(NC(CCl)=O)N=NC1=C(C=C(C=C1)Cl)C(C1=C(C=CC=C1)Cl)=O)=O AXWHLJPTWDPRRN-UHFFFAOYSA-N 0.000 description 1
- FIRXYFZXNJPHDX-UHFFFAOYSA-N diethyl 2-[(2-chloroacetyl)amino]propanedioate Chemical compound CCOC(=O)C(NC(=O)CCl)C(=O)OCC FIRXYFZXNJPHDX-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VVOISGODVGAYPS-UHFFFAOYSA-N ethyl 1-(2-benzoyl-4-nitrophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)N=C(CCl)N1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 VVOISGODVGAYPS-UHFFFAOYSA-N 0.000 description 1
- GBLUEKKEMVNCGT-UHFFFAOYSA-N ethyl 1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-(chloromethyl)-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl GBLUEKKEMVNCGT-UHFFFAOYSA-N 0.000 description 1
- QIHNBRTVYICNTQ-UHFFFAOYSA-N ethyl 1h-1,4-benzodiazepine-2-carboxylate Chemical compound N1C(C(=O)OCC)=CN=CC2=CC=CC=C21 QIHNBRTVYICNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 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 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000002496 oximetry Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1088571A CH553801A (de) | 1971-07-23 | 1971-07-23 | Verfahren zur herstellung von neuen diazepinderivaten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU472505A3 true SU472505A3 (ru) | 1975-05-30 |
Family
ID=4367854
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1813891A SU472505A3 (ru) | 1971-07-23 | 1972-07-21 | Способ получени производных диазепина |
| SU1993157A SU497776A3 (ru) | 1971-07-23 | 1974-01-30 | Способ получени производных диазепина |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1993157A SU497776A3 (ru) | 1971-07-23 | 1974-01-30 | Способ получени производных диазепина |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3878205A (fr) |
| JP (1) | JPS561316B1 (fr) |
| AR (2) | AR194603A1 (fr) |
| AT (2) | AT319956B (fr) |
| AU (1) | AU472145B2 (fr) |
| BE (1) | BE786530A (fr) |
| CA (1) | CA967956A (fr) |
| CH (1) | CH553801A (fr) |
| CS (2) | CS178450B2 (fr) |
| DD (1) | DD99578A5 (fr) |
| DE (1) | DE2234652A1 (fr) |
| FI (1) | FI52729C (fr) |
| FR (1) | FR2147092B1 (fr) |
| GB (1) | GB1395416A (fr) |
| HU (1) | HU165319B (fr) |
| IE (1) | IE36563B1 (fr) |
| IL (1) | IL39883A (fr) |
| NL (1) | NL7209809A (fr) |
| NO (1) | NO134868C (fr) |
| PL (1) | PL85681B1 (fr) |
| SE (1) | SE380804B (fr) |
| SU (2) | SU472505A3 (fr) |
| ZA (1) | ZA724839B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209516A (en) * | 1974-01-14 | 1980-06-24 | Ciba-Geigy Corporation | Triazole derivatives |
| JPS5747915B2 (fr) * | 1974-04-17 | 1982-10-13 | ||
| US4209515A (en) * | 1974-06-14 | 1980-06-24 | Ciba-Geigy Corporation | Triazole derivatives |
| US3996230A (en) * | 1975-03-28 | 1976-12-07 | The Upjohn Company | 1-Piperazino-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| US4510141A (en) * | 1982-09-13 | 1985-04-09 | Ciba-Geigy Corporation | Tricyclic polyazaheterocycles for treating depression or anxiety |
| CN118019742A (zh) | 2021-09-29 | 2024-05-10 | 豪夫迈·罗氏有限公司 | 作为GABA A γ1 PAM的新颖苯并二氮杂䓬衍生物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758921A (fr) * | 1969-11-15 | 1971-04-16 | Takeda Chemical Industries Ltd | Derives de benzodiazepine |
-
0
- BE BE786530D patent/BE786530A/fr unknown
-
1971
- 1971-07-23 CH CH1088571A patent/CH553801A/xx not_active IP Right Cessation
-
1972
- 1972-06-28 FI FI721828A patent/FI52729C/fi active
- 1972-07-11 IL IL39883A patent/IL39883A/en unknown
- 1972-07-12 IE IE982/72A patent/IE36563B1/xx unknown
- 1972-07-13 ZA ZA724839A patent/ZA724839B/xx unknown
- 1972-07-13 SE SE7209242A patent/SE380804B/xx unknown
- 1972-07-14 US US272088A patent/US3878205A/en not_active Expired - Lifetime
- 1972-07-14 NL NL7209809A patent/NL7209809A/xx not_active Application Discontinuation
- 1972-07-14 DE DE2234652A patent/DE2234652A1/de active Pending
- 1972-07-17 CA CA147,245A patent/CA967956A/en not_active Expired
- 1972-07-19 NO NO2588/72A patent/NO134868C/no unknown
- 1972-07-20 CS CS489A patent/CS178450B2/cs unknown
- 1972-07-20 CS CS5172A patent/CS178411B2/cs unknown
- 1972-07-21 SU SU1813891A patent/SU472505A3/ru active
- 1972-07-21 DD DD164605A patent/DD99578A5/xx unknown
- 1972-07-21 HU HUCI1256A patent/HU165319B/hu unknown
- 1972-07-21 GB GB3421672A patent/GB1395416A/en not_active Expired
- 1972-07-21 FR FR7226331A patent/FR2147092B1/fr not_active Expired
- 1972-07-21 AU AU44837/72A patent/AU472145B2/en not_active Expired
- 1972-07-21 AT AT1013073A patent/AT319956B/de not_active IP Right Cessation
- 1972-07-21 AT AT631372A patent/AT318625B/de not_active IP Right Cessation
- 1972-07-21 PL PL1972156882A patent/PL85681B1/pl unknown
- 1972-07-22 JP JP7305972A patent/JPS561316B1/ja active Pending
- 1972-07-24 AR AR243233A patent/AR194603A1/es active
-
1973
- 1973-05-29 AR AR248269A patent/AR197989A1/es active
-
1974
- 1974-01-30 SU SU1993157A patent/SU497776A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA724839B (en) | 1973-04-25 |
| IE36563L (en) | 1973-01-23 |
| AT319956B (de) | 1975-01-27 |
| IE36563B1 (en) | 1976-12-08 |
| HU165319B (fr) | 1974-08-28 |
| SU497776A3 (ru) | 1975-12-30 |
| DD99578A5 (fr) | 1973-08-12 |
| FR2147092B1 (fr) | 1975-08-08 |
| IL39883A (en) | 1976-06-30 |
| CA967956A (en) | 1975-05-20 |
| NO134868B (fr) | 1976-09-20 |
| SE380804B (sv) | 1975-11-17 |
| GB1395416A (en) | 1975-05-29 |
| FR2147092A1 (fr) | 1973-03-09 |
| IL39883A0 (en) | 1972-09-28 |
| CS178411B2 (fr) | 1977-09-15 |
| BE786530A (fr) | 1973-01-22 |
| AU472145B2 (en) | 1976-05-20 |
| CS178450B2 (fr) | 1977-09-15 |
| DE2234652A1 (de) | 1973-02-01 |
| PL85681B1 (fr) | 1976-04-30 |
| JPS561316B1 (fr) | 1981-01-13 |
| NL7209809A (fr) | 1973-01-25 |
| AU4483772A (en) | 1974-01-24 |
| CH553801A (de) | 1974-09-13 |
| FI52729C (fi) | 1977-11-10 |
| AR194603A1 (es) | 1973-07-31 |
| AT318625B (de) | 1974-11-11 |
| AR197989A1 (es) | 1974-05-24 |
| NO134868C (fr) | 1976-12-29 |
| US3878205A (en) | 1975-04-15 |
| FI52729B (fr) | 1977-08-01 |
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