NO132933B - - Google Patents

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Info

Publication number: NO132933B
Authority: NO; Norway
Prior art keywords: same meaning; general formula; compound; oxide; nitrogen atom
Prior art date: 1970-12-11

Application number

NO4384/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO132933C (de

Inventor

K Meguro

Y Kuwada

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1970-12-11

Filing date

1971-11-29

Publication date

1975-10-27

1971-11-29 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1975-10-27 Publication of NO132933B publication Critical patent/NO132933B/no

1976-02-04 Publication of NO132933C publication Critical patent/NO132933C/no

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)

NO4384/71A 1970-12-11 1971-11-29 NO132933C (de)

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)	CH569735A5 (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)

* Cited by examiner, † Cited by third party
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
AT361486B (de) *	1975-08-07	1981-03-10	Hoffmann La Roche	Verfahren zur herstellung von neuen imidazo(1,5 -a) (1,4)diazepinverbindungen, ihren salzen und optisch aktiven formen
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI50981C (fi) *	1968-11-05	1976-09-10	Takeda Chemical Industries Ltd	Menetelmä unilääkkeinä ja rauhoittavina lääkkeinä vaikuttavien s-triat solo-(4,3-a)(1,4)-bentsodiatsepiinien valmistamiseksi.
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
CH545803A (de)	1971-01-21	1974-02-15
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 DE DE19712159242 patent/DE2159242A1/de active Granted
- 1971-11-30 ZA ZA718044A patent/ZA718044B/xx unknown
- 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 CH1796171A patent/CH569735A5/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 CH1552974A patent/CH567022A5/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 ES ES397845A patent/ES397845A1/es not_active Expired
- 1971-12-10 CA CA129,850A patent/CA975363A/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 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 FR FR7144501A patent/FR2118028B1/fr 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
ZA718044B (en)	1972-08-30
US4235775A (en)	1980-11-25
NL173523B (nl)	1983-09-01
AU453008B2 (en)	1974-09-19
NO132933C (de)	1976-02-04
FR2118028B1 (de)	1975-06-13
CH569735A5 (de)	1975-11-28
AT315858B (de)	1974-06-10
ES397845A1 (es)	1975-05-16
DE2166657C2 (de)	1988-10-20
PH10822A (en)	1977-09-08
DE2159242A1 (de)	1972-12-07
DK141996B (da)	1980-08-04
GB1374469A (en)	1974-11-20
BE776514A (fr)	1972-04-04
DE2166657A1 (de)	1975-01-23
HU164524B (de)	1974-02-28
GB1374470A (en)	1974-11-20
CA975363A (en)	1975-09-30
CH567022A5 (de)	1975-09-30
YU35141B (en)	1980-09-25
DE2159242C2 (de)	1988-01-28
NL7116874A (de)	1972-06-13
AU3680271A (en)	1973-06-14
DK141996C (de)	1980-12-15
NL173523C (nl)	1984-02-01
FR2118028A1 (de)	1972-07-28
FI53128C (de)	1978-02-10
JPS4932874B1 (de)	1974-09-03
FI53128B (de)	1977-10-31
YU309471A (en)	1980-03-15
AT315181B (de)	1974-05-10

Publication	Publication Date	Title
US3950343A (en)	1976-04-13	Pyrroloisoquinoline derivatives
NO132933B (de)	1975-10-27
CS251795B2 (en)	1987-08-13	Method of 5h-2,3-benzodiazepine's derivatives preparation
JP2007502307A (ja)	2007-02-08	グルタミン酸ラセマーゼ（ｍｕｒｉ）の阻害剤としての縮合複素環
US3317524A (en)	1967-05-02	Substituted 1, 2, 3, 4-tetrahydro-pyrazino[1, 2-a]indoles
EP0655451B1 (de)	2001-06-20	Tetracyclische kondensierte heterocyclische Verbindungen zur Behandlung von seniler Demenz
AU640649B2 (en)	1993-09-02	9-substituted-8-unsubstituted-9-deazaguanines
JPH0433791B2 (de)	1992-06-04
JPS5831351B2 (ja)	1983-07-05	６−フエニル−Ｓ−トリアゾロ−（４，３−ａ）−ピリド−（２，３−ｆ）−（１，４）−ジアゼピン及びその製造方法
US3784556A (en)	1974-01-08	Certain 2-amino-6-phenyl-4h-s-triazolo (1,5-a)(1,4)benzodiazepines
US3651046A (en)	1972-03-21	Quinazolino-benzodiazepines and methods for the preparation thereof
US4587245A (en)	1986-05-06	Method of treating neuropsychic disturbances by benzodiazepine derivatives and composition therefor
US3852300A (en)	1974-12-03	CERTAIN 6-PHENYL-4H-S-TRIAZOLO{8 1,5-a{9 {8 1,4-BENZODIAZEPINES{9
US3947408A (en)	1976-03-30	Pyrrolo-benzodiazepines, method of preparation and method of use
US3846421A (en)	1974-11-05	Triazolobenzodiazepine derivatives
US4002638A (en)	1977-01-11	Benzazepine derivatives
IL39883A (en)	1976-06-30	2-aminomethyl-6-phenyl-4h-s-triazolo(1,5-alpha)(1,4)benzodiazepine derivatives,their production and pharmaceutical compositions containing them
JPH02268168A (ja)	1990-11-01	ベンゾジアゼピン
GB2055372A (en)	1981-03-04	Texahydro-trans-pyridoindole neuroleptic agents
US3857854A (en)	1974-12-31	6-phenyl-1h,4h-{8 1,2,4{9 oxadiazalo{8 4,3-2{9 {8 1,4{9 benzodiazepin-1-ones
US3968230A (en)	1976-07-06	Compositions containing benzodiazepindiones and method of use
US3268586A (en)	1966-08-23	Armnophenyl cycloalkyl ketones
CA1087182A (en)	1980-10-07	Substituted 1-piperazinyl-triazolo-thieno-1,4- diazepines
US3755360A (en)	1973-08-28	2,3,4,5-tetrahydro-7h-(1,3)diazepino-(2,1-a)isoindoles
US3838174A (en)	1974-09-24	3-phenyl-3-ortho amino phenylphthalanols