DE3014011A1 - Benzo-as-triazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Benzo-as-triazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE3014011A1 DE3014011A1 DE19803014011 DE3014011A DE3014011A1 DE 3014011 A1 DE3014011 A1 DE 3014011A1 DE 19803014011 DE19803014011 DE 19803014011 DE 3014011 A DE3014011 A DE 3014011A DE 3014011 A1 DE3014011 A1 DE 3014011A1
- Authority
- DE
- Germany
- Prior art keywords
- benzo
- radical
- triazine
- triazolo
- triazine derivatives
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- GDAXJBDYNVDMDF-UHFFFAOYSA-N 1,2,4-benzotriazine Chemical class N1=NC=NC2=CC=CC=C21 GDAXJBDYNVDMDF-UHFFFAOYSA-N 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- -1 pyrazinylcarbonyl Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000003840 hydrochlorides Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- JDWSWQMLJIQTEP-UHFFFAOYSA-N 5-hydroxypyrazol-3-one Chemical group OC1=CC(=O)N=N1 JDWSWQMLJIQTEP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- DUCNKBZIKNAQOS-UHFFFAOYSA-N O=[C]C1=CC=CN=C1 Chemical compound O=[C]C1=CC=CN=C1 DUCNKBZIKNAQOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- SGEAPMBJSKNHBX-UHFFFAOYSA-N pyrazole-3,5-dione Chemical group O=C1CC(=O)N=N1 SGEAPMBJSKNHBX-UHFFFAOYSA-N 0.000 claims description 2
- BLZBTELUFMBNLX-UHFFFAOYSA-N 5-hydroxy-1,2-dihydropyrazol-3-one Chemical group OC1=CC(=O)NN1 BLZBTELUFMBNLX-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000001819 mass spectrum Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- YVLGNCIEJDIHQK-UHFFFAOYSA-N 3,5-dihydro-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazine Chemical compound N1NC2=CC=CC=C2N2C1=NN=C2 YVLGNCIEJDIHQK-UHFFFAOYSA-N 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 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
- 229960005489 paracetamol Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
- IJUSQMXFGMYLGQ-UHFFFAOYSA-N 1-(4-acetyl-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl)ethanone Chemical compound CC(=O)N1N(C(C)=O)C2=CC=CC=C2N2C1=NN=C2 IJUSQMXFGMYLGQ-UHFFFAOYSA-N 0.000 description 2
- XAPQRLRNCLYRFN-UHFFFAOYSA-N 1-(4h-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)NC3=NN=CN3C2=C1 XAPQRLRNCLYRFN-UHFFFAOYSA-N 0.000 description 2
- HMNDQUGVMLNXEZ-UHFFFAOYSA-N 1-(4h-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl)propan-1-one Chemical compound C1=CC=C2N(C(=O)CC)NC3=NN=CN3C2=C1 HMNDQUGVMLNXEZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000010513 Stupor Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960004815 meprobamate Drugs 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229960005333 tetrabenazine Drugs 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- RCGYOVLNPQDSAV-UHFFFAOYSA-N 1,2,4-benzotriazine dihydrochloride Chemical compound Cl.Cl.N1=NC=NC2=C1C=CC=C2 RCGYOVLNPQDSAV-UHFFFAOYSA-N 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZFLICVANUASFIR-UHFFFAOYSA-N 1-(1-methylsulfanyl-4-propanoyl-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl)propan-1-one Chemical compound CCC(=O)N1N(C(=O)CC)C2=CC=CC=C2N2C1=NN=C2SC ZFLICVANUASFIR-UHFFFAOYSA-N 0.000 description 1
- LTPIXWWCANXFSM-UHFFFAOYSA-N 1-(4-octadecanoyl-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl)octadecan-1-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)N1N(C(=O)CCCCCCCCCCCCCCCCC)C2=CC=CC=C2N2C1=NN=C2 LTPIXWWCANXFSM-UHFFFAOYSA-N 0.000 description 1
- AJGLEHMKALKOKG-UHFFFAOYSA-N 1-(4-propanoyl-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl)propan-1-one Chemical compound CCC(=O)N1N(C(=O)CC)C2=CC=CC=C2N2C1=NN=C2 AJGLEHMKALKOKG-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- ZKQGDULKQKNVHR-UHFFFAOYSA-N 1-[1-(4-methylpiperazin-1-yl)-4-propanoyl-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl]propan-1-one Chemical compound N=1N=C2N(C(=O)CC)N(C(=O)CC)C3=CC=CC=C3N2C=1N1CCN(C)CC1 ZKQGDULKQKNVHR-UHFFFAOYSA-N 0.000 description 1
- KOEIXVZMTIOQMJ-UHFFFAOYSA-N 1-butylpyrazolidine-3,5-dione Chemical compound CCCCN1NC(=O)CC1=O KOEIXVZMTIOQMJ-UHFFFAOYSA-N 0.000 description 1
- XFCKCXJLCKRUFG-UHFFFAOYSA-N 2-chloro-1-[4-(2-chloroacetyl)-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-5-yl]ethanone Chemical compound ClCC(=O)N1N(C(=O)CCl)C2=CC=CC=C2N2C1=NN=C2 XFCKCXJLCKRUFG-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- ZPKLKQNMZTUIFZ-UHFFFAOYSA-N 2-phenylethanone Chemical compound O=[C]CC1=CC=CC=C1 ZPKLKQNMZTUIFZ-UHFFFAOYSA-N 0.000 description 1
- MLNSYGKGQFHSNI-UHFFFAOYSA-N 2-propylpropanedioyl dichloride Chemical compound CCCC(C(Cl)=O)C(Cl)=O MLNSYGKGQFHSNI-UHFFFAOYSA-N 0.000 description 1
- SJTHSEBGKUXZSR-UHFFFAOYSA-N 2H-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-1-one Chemical compound C1(NN=C2N=NC3=C(N21)C=CC=C3)=O SJTHSEBGKUXZSR-UHFFFAOYSA-N 0.000 description 1
- WUKGDOPTNMQMCQ-UHFFFAOYSA-N 3,5-dihydro-2h-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-1-one Chemical compound C1=CC=C2N3C(=O)NNC3=NNC2=C1 WUKGDOPTNMQMCQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UNBPKAKPNOMMQM-UHFFFAOYSA-N 4-butyl-1,2-diphenylpyrazolidine Chemical compound C1C(CCCC)CN(C=2C=CC=CC=2)N1C1=CC=CC=C1 UNBPKAKPNOMMQM-UHFFFAOYSA-N 0.000 description 1
- DLEQTSUDAVCHRV-UHFFFAOYSA-N 7-chloro-2,4,5-tri(propanoyl)-[1,2,4]triazolo[3,4-c][1,2,4]benzotriazin-1-one Chemical compound ClC1=CC=C2N3C(=O)N(C(=O)CC)N=C3N(C(=O)CC)N(C(=O)CC)C2=C1 DLEQTSUDAVCHRV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 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
- RZIVOIQAYOABCF-UHFFFAOYSA-N [1,2,4]triazolo[3,4-c][1,2,4]benzotriazine Chemical compound C1=CC=C2N3C=NN=C3N=NC2=C1 RZIVOIQAYOABCF-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 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
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2646A HU179158B (en) | 1979-04-11 | 1979-04-11 | Process for producing triasolo-benzo-asimetrical-triasine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3014011A1 true DE3014011A1 (de) | 1980-11-27 |
Family
ID=10995838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803014011 Withdrawn DE3014011A1 (de) | 1979-04-11 | 1980-04-11 | Benzo-as-triazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4316022A (enExample) |
| AT (1) | AT380255B (enExample) |
| AU (1) | AU534271B2 (enExample) |
| BE (1) | BE882675A (enExample) |
| CH (1) | CH644125A5 (enExample) |
| DD (1) | DD150061A5 (enExample) |
| DE (1) | DE3014011A1 (enExample) |
| ES (1) | ES490505A0 (enExample) |
| FR (1) | FR2453861A1 (enExample) |
| GB (1) | GB2047693B (enExample) |
| GR (1) | GR68093B (enExample) |
| HU (1) | HU179158B (enExample) |
| IT (1) | IT1212412B (enExample) |
| NL (1) | NL8002120A (enExample) |
| SU (2) | SU1187722A3 (enExample) |
| YU (1) | YU100180A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624925A (en) | 1986-09-25 | 1997-04-29 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| US5175287A (en) * | 1986-09-25 | 1992-12-29 | S R I International | Process for preparing 1,2,4-benzotriazine oxides |
| WO2000034278A1 (en) * | 1998-12-04 | 2000-06-15 | Toray Industries, Inc. | Triazolo derivatives and chemokine inhibitors containing the same as the active ingredient |
| US6833454B1 (en) | 2003-01-15 | 2004-12-21 | The United States Of America As Represented By The Secretary Of The Navy | Chemical compounds containing bis(triazolo)triazine structures and methods thereof |
| EP1502918A1 (en) * | 2003-07-31 | 2005-02-02 | Bayer CropScience GmbH | The use of fused ring-1,2,4-benzotriazine derivatives as herbicides or plant growth regulators for the control of undesired plants or vegetation, compounds and compositions thereof, and processes for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933816A (en) * | 1974-09-12 | 1976-01-20 | The Upjohn Company | 3-(Substituted aminomethyl)-7-substituted-3,5-dihydro-as-triazino[4,3-a][1,5]benzodiazepines |
| US4017492A (en) * | 1976-04-02 | 1977-04-12 | The Upjohn Company | As-triazinobenzodiazepin-1-ones |
-
1979
- 1979-04-11 HU HU79EE2646A patent/HU179158B/hu not_active IP Right Cessation
-
1980
- 1980-03-28 US US06/135,143 patent/US4316022A/en not_active Expired - Lifetime
- 1980-03-31 GB GB8010792A patent/GB2047693B/en not_active Expired
- 1980-04-02 GR GR61603A patent/GR68093B/el unknown
- 1980-04-03 SU SU802902200A patent/SU1187722A3/ru active
- 1980-04-08 BE BE1/9779A patent/BE882675A/fr not_active IP Right Cessation
- 1980-04-08 DD DD80220282A patent/DD150061A5/de unknown
- 1980-04-10 IT IT8021284A patent/IT1212412B/it active
- 1980-04-10 AU AU57301/80A patent/AU534271B2/en not_active Ceased
- 1980-04-10 FR FR8008051A patent/FR2453861A1/fr active Granted
- 1980-04-10 CH CH274180A patent/CH644125A5/de not_active IP Right Cessation
- 1980-04-11 AT AT0197380A patent/AT380255B/de not_active IP Right Cessation
- 1980-04-11 ES ES490505A patent/ES490505A0/es active Granted
- 1980-04-11 YU YU01001/80A patent/YU100180A/xx unknown
- 1980-04-11 NL NL8002120A patent/NL8002120A/nl not_active Application Discontinuation
- 1980-04-11 DE DE19803014011 patent/DE3014011A1/de not_active Withdrawn
-
1982
- 1982-02-18 SU SU823393298A patent/SU1234401A1/ru active
Non-Patent Citations (2)
| Title |
|---|
| CA 72, 1970, 12692 b * |
| CA 86, 1977, 72583 r * |
Also Published As
| Publication number | Publication date |
|---|---|
| YU100180A (en) | 1983-09-30 |
| ES8104807A1 (es) | 1981-04-16 |
| AU534271B2 (en) | 1984-01-12 |
| AT380255B (de) | 1986-05-12 |
| IT1212412B (it) | 1989-11-22 |
| SU1234401A1 (ru) | 1986-05-30 |
| AU5730180A (en) | 1980-10-16 |
| FR2453861B1 (enExample) | 1983-06-24 |
| SU1187722A3 (ru) | 1985-10-23 |
| GR68093B (enExample) | 1981-10-30 |
| IT8021284A0 (it) | 1980-04-10 |
| ES490505A0 (es) | 1981-04-16 |
| NL8002120A (nl) | 1980-10-14 |
| BE882675A (fr) | 1980-10-08 |
| GB2047693B (en) | 1983-05-25 |
| GB2047693A (en) | 1980-12-03 |
| HU179158B (en) | 1982-08-28 |
| FR2453861A1 (fr) | 1980-11-07 |
| US4316022A (en) | 1982-02-16 |
| CH644125A5 (de) | 1984-07-13 |
| ATA197380A (de) | 1985-09-15 |
| DD150061A5 (de) | 1981-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |