NO132933B - - Google Patents
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- Publication number
- NO132933B NO132933B NO4384/71A NO438471A NO132933B NO 132933 B NO132933 B NO 132933B NO 4384/71 A NO4384/71 A NO 4384/71A NO 438471 A NO438471 A NO 438471A NO 132933 B NO132933 B NO 132933B
- Authority
- NO
- Norway
- Prior art keywords
- same meaning
- general formula
- compound
- oxide
- nitrogen atom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- KYTREVLPRJOBEM-UHFFFAOYSA-N triazolo[4,5-i][1,2]benzodiazepine Chemical class C1=CC2=CC=CN=NC2=C2C1=NN=N2 KYTREVLPRJOBEM-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- -1 psychosedative Substances 0.000 description 8
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000932 sedative agent Substances 0.000 description 6
- 230000001624 sedative effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003158 myorelaxant agent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000002040 relaxant effect Effects 0.000 description 3
- 229940125723 sedative agent Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-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
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- GWSXDWFXNVOIIC-UHFFFAOYSA-N (7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)hydrazine Chemical compound N=1CC(NN)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 GWSXDWFXNVOIIC-UHFFFAOYSA-N 0.000 description 1
- CIEBUYROYKGPDC-UHFFFAOYSA-N 1-(8-chloro-5-oxido-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-5-ium-1-yl)-n,n-dimethylmethanamine Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2C[N+]([O-])=C1C1=CC=CC=C1 CIEBUYROYKGPDC-UHFFFAOYSA-N 0.000 description 1
- XPMACCNVZKHGPT-UHFFFAOYSA-N 1-(8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-n-methylmethanamine Chemical compound C12=CC(Cl)=CC=C2N2C(CNC)=NN=C2CN=C1C1=CC=CC=C1 XPMACCNVZKHGPT-UHFFFAOYSA-N 0.000 description 1
- CQTKONQMSBMSLG-UHFFFAOYSA-N 1-(bromomethyl)-8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N2C(CBr)=NN=C2CN=2)C=1C=2C1=CC=CC=C1 CQTKONQMSBMSLG-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- LVCXDKYVLLYQIH-UHFFFAOYSA-N 1-[8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl LVCXDKYVLLYQIH-UHFFFAOYSA-N 0.000 description 1
- YSKXJLOUBWWXFA-UHFFFAOYSA-N 1-[8-chloro-6-(4-methoxyphenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C1=CC(OC)=CC=C1C1=NCC2=NN=C(CN(C)C)N2C2=CC=C(Cl)C=C12 YSKXJLOUBWWXFA-UHFFFAOYSA-N 0.000 description 1
- MSBSHUNLSUABTN-UHFFFAOYSA-N 2-[4-[(8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CC1=NN=C2N1C1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)=NC2 MSBSHUNLSUABTN-UHFFFAOYSA-N 0.000 description 1
- SBMGVOGULSMFEO-UHFFFAOYSA-N 4-[(8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methyl]morpholine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C=CC=CC=1)=NCC3=NN=C2CN1CCOCC1 SBMGVOGULSMFEO-UHFFFAOYSA-N 0.000 description 1
- GOGYLAXZWVRXNA-UHFFFAOYSA-N 8-chloro-1-[(4-methylpiperazin-1-yl)methyl]-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C1CN(C)CCN1CC1=NN=C2N1C1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)=NC2 GOGYLAXZWVRXNA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 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
- 125000004429 atom Chemical group 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000003635 deoxygenating effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- OUGDNLWJKYDPDQ-UHFFFAOYSA-N n,n-dimethyl-1-(6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical compound C12=CC=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 OUGDNLWJKYDPDQ-UHFFFAOYSA-N 0.000 description 1
- NSBOMOVWNCUVNL-UHFFFAOYSA-N n,n-dimethyl-1-(8-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical compound C12=CC(C)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 NSBOMOVWNCUVNL-UHFFFAOYSA-N 0.000 description 1
- YTVYBJLYJZNDJZ-UHFFFAOYSA-N n,n-dimethyl-1-(8-nitro-5-oxido-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-5-ium-1-yl)methanamine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2C(CN(C)C)=NN=C2C[N+]([O-])=C1C1=CC=CC=C1 YTVYBJLYJZNDJZ-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- PZCWZBPBSKCHBC-UHFFFAOYSA-N n-[(8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methyl]cyclohexanamine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C=CC=CC=1)=NCC3=NN=C2CNC1CCCCC1 PZCWZBPBSKCHBC-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000012976 tarts Nutrition 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45110716A JPS4932874B1 (de) | 1970-12-11 | 1970-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132933B true NO132933B (de) | 1975-10-27 |
| NO132933C NO132933C (de) | 1976-02-04 |
Family
ID=14542652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4384/71A NO132933C (de) | 1970-12-11 | 1971-11-29 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4235775A (de) |
| JP (1) | JPS4932874B1 (de) |
| AT (2) | AT315858B (de) |
| AU (1) | AU453008B2 (de) |
| BE (1) | BE776514A (de) |
| CA (1) | CA975363A (de) |
| CH (2) | CH567022A5 (de) |
| DE (2) | DE2166657A1 (de) |
| DK (1) | DK141996B (de) |
| ES (1) | ES397845A1 (de) |
| FI (1) | FI53128C (de) |
| FR (1) | FR2118028B1 (de) |
| GB (2) | GB1374470A (de) |
| HU (1) | HU164524B (de) |
| NL (1) | NL173523C (de) |
| NO (1) | NO132933C (de) |
| PH (1) | PH10822A (de) |
| YU (1) | YU35141B (de) |
| ZA (1) | ZA718044B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1331015A (en) * | 1971-04-28 | 1973-09-19 | Upjohn Co | 1-substituted-6-phenyl-4h-s-triazolo-4,3-a-1,4-benzodiazepines |
| US4141902A (en) * | 1971-04-28 | 1979-02-27 | The Upjohn Company | 1-Halomethyl-6-phenyl-4H-s-[4,3-a][1,4]benzodiazepines |
| GB1377230A (en) * | 1971-09-13 | 1974-12-11 | Upjohn Co | 4h-s-triazolo -4,3-a- 1,4-benzodiazepines |
| US3842090A (en) * | 1973-02-14 | 1974-10-15 | Upjohn Co | Certain 1-aminomethyl-6-phenyl 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
| US3894025A (en) * | 1974-03-21 | 1975-07-08 | Upjohn Co | 1-Piperazino-6-phenyl-4H-s-triazolo{8 4,3-a{9 {8 1,4{9 -benzodiazepine compounds |
| CA1055490A (en) * | 1974-06-19 | 1979-05-29 | Upjohn Company (The) | Process for preparing triazolobenzodiazepines |
| ZA755418B (en) * | 1974-09-11 | 1977-06-29 | Hoffmann La Roche | Diazepine derivatives |
| US4021441A (en) * | 1975-04-07 | 1977-05-03 | The Upjohn Company | 1-[(Allylamino)-methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| AU509371B2 (en) * | 1975-08-07 | 1980-05-08 | F. Hoffmann-La Roche Ag | Diazepine Derivatives |
| US4009175A (en) * | 1976-03-15 | 1977-02-22 | The Upjohn Company | 1-[(Aminooxy)-methyl]-6-substituted-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 |
| US4663454A (en) * | 1985-04-17 | 1987-05-05 | The Upjohn Company | Process to prepare α-chloroalprazolam |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH9315A (en) * | 1968-11-05 | 1975-08-22 | K Meguro | Triazolo(4,3-a)(1,4)benzodiazepine derivatives |
| FR2022598A1 (en) * | 1969-11-04 | 1970-07-31 | Pakeda Chemical Ind | Sedative chloro-phenyl-triazolobenzodiazepines |
| DE2156472A1 (de) | 1970-11-23 | 1972-05-31 | Ciba-Geigy Ag, Basel (Schweiz) | Verfahren zur Herstellung von neuen Diazepinderivaten |
| CH544764A (de) | 1971-01-21 | 1974-01-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivaten |
| US3681343A (en) * | 1971-05-11 | 1972-08-01 | Upjohn Co | 6-phenyl-s-triazolo{8 4,3-a{9 {8 1,4{9 {0 benzodiazepines |
-
1970
- 1970-12-11 JP JP45110716A patent/JPS4932874B1/ja active Pending
-
1971
- 1971-11-29 NO NO4384/71A patent/NO132933C/no unknown
- 1971-11-30 DE DE19712166657 patent/DE2166657A1/de active Granted
- 1971-11-30 ZA ZA718044A patent/ZA718044B/xx unknown
- 1971-11-30 DE DE19712159242 patent/DE2159242A1/de active Granted
- 1971-12-06 PH PH13074A patent/PH10822A/en unknown
- 1971-12-08 NL NLAANVRAGE7116874,A patent/NL173523C/xx not_active IP Right Cessation
- 1971-12-09 CH CH1552974A patent/CH567022A5/xx not_active IP Right Cessation
- 1971-12-09 FI FI3513/71A patent/FI53128C/fi active
- 1971-12-09 YU YU3094/71A patent/YU35141B/xx unknown
- 1971-12-09 CH CH1796171A patent/CH569735A5/xx not_active IP Right Cessation
- 1971-12-09 GB GB2027774A patent/GB1374470A/en not_active Expired
- 1971-12-09 GB GB5719171A patent/GB1374469A/en not_active Expired
- 1971-12-10 AT AT481273A patent/AT315858B/de not_active IP Right Cessation
- 1971-12-10 DK DK603471AA patent/DK141996B/da not_active IP Right Cessation
- 1971-12-10 FR FR7144501A patent/FR2118028B1/fr not_active Expired
- 1971-12-10 AT AT1064071A patent/AT315181B/de not_active IP Right Cessation
- 1971-12-10 BE BE776514A patent/BE776514A/xx not_active IP Right Cessation
- 1971-12-10 CA CA129,850A patent/CA975363A/en not_active Expired
- 1971-12-10 ES ES397845A patent/ES397845A1/es not_active Expired
- 1971-12-11 HU HUTA1154A patent/HU164524B/hu unknown
- 1971-12-13 AU AU36802/71A patent/AU453008B2/en not_active Expired
-
1979
- 1979-06-15 US US06/049,055 patent/US4235775A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL173523C (nl) | 1984-02-01 |
| FR2118028A1 (de) | 1972-07-28 |
| ZA718044B (en) | 1972-08-30 |
| BE776514A (fr) | 1972-04-04 |
| DK141996B (da) | 1980-08-04 |
| NO132933C (de) | 1976-02-04 |
| AU453008B2 (en) | 1974-09-19 |
| DE2166657A1 (de) | 1975-01-23 |
| ES397845A1 (es) | 1975-05-16 |
| YU309471A (en) | 1980-03-15 |
| AT315858B (de) | 1974-06-10 |
| NL7116874A (de) | 1972-06-13 |
| DK141996C (de) | 1980-12-15 |
| CA975363A (en) | 1975-09-30 |
| YU35141B (en) | 1980-09-25 |
| AT315181B (de) | 1974-05-10 |
| AU3680271A (en) | 1973-06-14 |
| US4235775A (en) | 1980-11-25 |
| DE2159242C2 (de) | 1988-01-28 |
| NL173523B (nl) | 1983-09-01 |
| GB1374469A (en) | 1974-11-20 |
| PH10822A (en) | 1977-09-08 |
| FI53128C (de) | 1978-02-10 |
| CH567022A5 (de) | 1975-09-30 |
| FI53128B (de) | 1977-10-31 |
| JPS4932874B1 (de) | 1974-09-03 |
| FR2118028B1 (de) | 1975-06-13 |
| DE2159242A1 (de) | 1972-12-07 |
| HU164524B (de) | 1974-02-28 |
| GB1374470A (en) | 1974-11-20 |
| DE2166657C2 (de) | 1988-10-20 |
| CH569735A5 (de) | 1975-11-28 |
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