CA1062256A - Benzazepine derivatives - Google Patents
Benzazepine derivativesInfo
- Publication number
- CA1062256A CA1062256A CA209,274A CA209274A CA1062256A CA 1062256 A CA1062256 A CA 1062256A CA 209274 A CA209274 A CA 209274A CA 1062256 A CA1062256 A CA 1062256A
- Authority
- CA
- Canada
- Prior art keywords
- triazolo
- benzazepin
- dihydro
- formula
- compound
- 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.)
- Expired
Links
- 150000008038 benzoazepines Chemical class 0.000 title abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052717 sulfur Chemical group 0.000 claims abstract description 12
- 239000011593 sulfur Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- -1 morpholino, 1-pyrrolidinyl Chemical group 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- LJRBJFDQRCJULB-UHFFFAOYSA-N 2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)NN=C2CC2=CC=CC=C21 LJRBJFDQRCJULB-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- CWTSUEBNXOUGHX-UHFFFAOYSA-N 1h-3-benzazepin-2-ylhydrazine Chemical compound C1C(NN)=NC=CC2=CC=CC=C21 CWTSUEBNXOUGHX-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000005059 halophenyl group Chemical group 0.000 claims description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- WYSZNBHOUQAGIC-UHFFFAOYSA-N 2,5,6,11-tetrahydro-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)NN=C2CC2=CC=CC=C21 WYSZNBHOUQAGIC-UHFFFAOYSA-N 0.000 claims description 2
- WRMNPDJOULNIBU-UHFFFAOYSA-N 2-benzyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound N1=C2CC3=CC=CC=C3C=CN2C(=O)N1CC1=CC=CC=C1 WRMNPDJOULNIBU-UHFFFAOYSA-N 0.000 claims description 2
- YJNMRBHGDMKJLX-UHFFFAOYSA-N 2-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(C)N=C2CC2=CC=CC=C21 YJNMRBHGDMKJLX-UHFFFAOYSA-N 0.000 claims description 2
- JMACQUOBALBYDC-UHFFFAOYSA-N 8,9-dimethoxy-2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1C2=NNC(=O)N2C=CC2=C1C=C(OC)C(OC)=C2 JMACQUOBALBYDC-UHFFFAOYSA-N 0.000 claims description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 3
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 229940117953 phenylisothiocyanate Drugs 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 3
- 210000003205 muscle Anatomy 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 230000002040 relaxant effect Effects 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- SYIUPRKONIOYIL-UHFFFAOYSA-N 1-benzazepin-3-one Chemical compound N1=CC(=O)C=CC2=CC=CC=C21 SYIUPRKONIOYIL-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- BWOJTQQETZTVGT-UHFFFAOYSA-N (1h-3-benzazepin-2-ylamino)urea Chemical compound C1C(NNC(=O)N)=NC=CC2=CC=CC=C21 BWOJTQQETZTVGT-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BYPPFEHJEPMCFM-UHFFFAOYSA-N 2-ethyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(CC)N=C2CC2=CC=CC=C21 BYPPFEHJEPMCFM-UHFFFAOYSA-N 0.000 description 2
- GPRLCAFTNAULNY-UHFFFAOYSA-N 2-ethyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(CC)N=C2CC2=CC=CC=C21 GPRLCAFTNAULNY-UHFFFAOYSA-N 0.000 description 2
- VAXYLTGMMGTQIB-UHFFFAOYSA-N 2-methyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(C)N=C2CC2=CC=CC=C21 VAXYLTGMMGTQIB-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- LLFKVLMPTGTZGA-UHFFFAOYSA-N (7,8-dimethyl-1h-3-benzazepin-2-yl)hydrazine Chemical compound C1C(NN)=NC=CC2=C1C=C(C)C(C)=C2 LLFKVLMPTGTZGA-UHFFFAOYSA-N 0.000 description 1
- QGHQKHSVZVOHIO-UHFFFAOYSA-N 1-(1h-3-benzazepin-2-ylamino)-3-benzylurea Chemical compound N=1C=CC2=CC=CC=C2CC=1NNC(=O)NCC1=CC=CC=C1 QGHQKHSVZVOHIO-UHFFFAOYSA-N 0.000 description 1
- LAEFHEXCIOLSIJ-UHFFFAOYSA-N 1-(1h-3-benzazepin-2-ylamino)-3-methylurea Chemical compound C1C(NNC(=O)NC)=NC=CC2=CC=CC=C21 LAEFHEXCIOLSIJ-UHFFFAOYSA-N 0.000 description 1
- ZPXTVFZGXQSJTF-UHFFFAOYSA-N 1-(1h-3-benzazepin-2-ylamino)-3-phenylurea Chemical compound N=1C=CC2=CC=CC=C2CC=1NNC(=O)NC1=CC=CC=C1 ZPXTVFZGXQSJTF-UHFFFAOYSA-N 0.000 description 1
- GHNVLJXZJZKXJM-UHFFFAOYSA-N 10-chloro-2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepine-3-thione Chemical compound C1=CN2C(=S)NN=C2CC2=C1C=CC=C2Cl GHNVLJXZJZKXJM-UHFFFAOYSA-N 0.000 description 1
- NKYAUDACAYPWRT-UHFFFAOYSA-N 10-chloro-2-(2-methoxyethyl)-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(CCOC)N=C2CC2=C(Cl)C=CC=C21 NKYAUDACAYPWRT-UHFFFAOYSA-N 0.000 description 1
- HFJDYSQGDQNPDH-UHFFFAOYSA-N 1h-3-benzazepin-2-amine;hydrobromide Chemical compound Br.C1C(N)=NC=CC2=CC=CC=C21 HFJDYSQGDQNPDH-UHFFFAOYSA-N 0.000 description 1
- BUCOSGQQUGDVAW-UHFFFAOYSA-N 2,8,9-trimethyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(C)N=C2CC2=C1C=C(C)C(C)=C2 BUCOSGQQUGDVAW-UHFFFAOYSA-N 0.000 description 1
- COFPZXFQCNVDQU-UHFFFAOYSA-N 2-(2-methoxyethyl)-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(CCOC)N=C2CC2=CC=CC=C21 COFPZXFQCNVDQU-UHFFFAOYSA-N 0.000 description 1
- IDCLKIPILMQNKZ-UHFFFAOYSA-N 2-(2-piperazin-1-ylethyl)-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound N1=C2CC3=CC=CC=C3CCN2C(=O)N1CCN1CCNCC1 IDCLKIPILMQNKZ-UHFFFAOYSA-N 0.000 description 1
- FHMOMACUUSDBOV-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)ethyl]-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1CN(C)CCN1CCN1C(=O)N2C=CC3=CC=CC=C3CC2=N1 FHMOMACUUSDBOV-UHFFFAOYSA-N 0.000 description 1
- SUWMOXPEPBBQLY-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-8,9-dimethyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(CCN(C)C)N=C2CC2=CC(C)=C(C)C=C21 SUWMOXPEPBBQLY-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- DLXPSAMTOZCNMB-UHFFFAOYSA-N 2-ethyl-8,9-dimethyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(CC)N=C2CC2=CC(C)=C(C)C=C21 DLXPSAMTOZCNMB-UHFFFAOYSA-N 0.000 description 1
- SYUKRWAJKLTLQR-UHFFFAOYSA-N 2-hexyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(CCCCCC)N=C2CC2=CC=CC=C21 SYUKRWAJKLTLQR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OSUXFTCZXCDVMF-UHFFFAOYSA-N 2-propyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(CCC)N=C2CC2=CC=CC=C21 OSUXFTCZXCDVMF-UHFFFAOYSA-N 0.000 description 1
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- UQEKKNCVOWNBOT-UHFFFAOYSA-N 7-chloro-2-ethyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(CC)N=C2CC2=CC=CC(Cl)=C21 UQEKKNCVOWNBOT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZONBXFRGJCOVQO-UHFFFAOYSA-N 8,9-dimethoxy-2-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1C2=NN(C)C(=O)N2C=CC2=C1C=C(OC)C(OC)=C2 ZONBXFRGJCOVQO-UHFFFAOYSA-N 0.000 description 1
- NSLOFLSKBNAKPJ-UHFFFAOYSA-N 8,9-dimethyl-2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1C2=NNC(=O)N2C=CC2=C1C=C(C)C(C)=C2 NSLOFLSKBNAKPJ-UHFFFAOYSA-N 0.000 description 1
- DNVFYZOAOOWACQ-UHFFFAOYSA-N 8-chloro-2,5,6,11-tetrahydro-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CC2=CC(Cl)=CC=C2CC2=NNC(=O)N21 DNVFYZOAOOWACQ-UHFFFAOYSA-N 0.000 description 1
- JWTODBLFIVUXST-UHFFFAOYSA-N 8-chloro-2-methyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(C)N=C2CC2=CC=C(Cl)C=C21 JWTODBLFIVUXST-UHFFFAOYSA-N 0.000 description 1
- YENJZWQEXNKUNS-UHFFFAOYSA-N 9-chloro-2-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CN2C(=O)N(C)N=C2CC2=CC(Cl)=CC=C21 YENJZWQEXNKUNS-UHFFFAOYSA-N 0.000 description 1
- HVRJDEZJENFCNG-UHFFFAOYSA-N 9-chloro-2-methyl-6,11-dihydro-5h-[1,2,4]triazolo[4,3-c][3]benzazepin-3-one Chemical compound C1CN2C(=O)N(C)N=C2CC2=CC(Cl)=CC=C21 HVRJDEZJENFCNG-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 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
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- NUIWRMGOBPOIOY-UHFFFAOYSA-N ethanesulfonic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCS(O)(=O)=O NUIWRMGOBPOIOY-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LURQBQNWDYASPJ-UHFFFAOYSA-N hydrazinyl Chemical compound N[NH] LURQBQNWDYASPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- NWKYZYGOSPOKDY-UHFFFAOYSA-N n,n-dimethylformamide;pyridine Chemical compound CN(C)C=O.C1=CC=NC=C1 NWKYZYGOSPOKDY-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10425673A JPS5711914B2 (en, 2012) | 1973-09-14 | 1973-09-14 | |
| JP617374A JPS5719112B2 (en, 2012) | 1974-01-10 | 1974-01-10 | |
| JP2306274A JPS5742079B2 (en, 2012) | 1974-02-26 | 1974-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062256A true CA1062256A (en) | 1979-09-11 |
Family
ID=27277049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA209,274A Expired CA1062256A (en) | 1973-09-14 | 1974-09-16 | Benzazepine derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4002638A (en, 2012) |
| BE (1) | BE819893A (en, 2012) |
| CA (1) | CA1062256A (en, 2012) |
| CH (1) | CH615435A5 (en, 2012) |
| DE (1) | DE2442987A1 (en, 2012) |
| FR (1) | FR2243700B1 (en, 2012) |
| GB (1) | GB1453910A (en, 2012) |
| NL (1) | NL7412222A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU505150B2 (en) | 1976-08-06 | 1979-11-08 | Takeda Chemical Industries, Ltd | Triazolobenzazepine derivatives |
| US4243589A (en) * | 1979-11-30 | 1981-01-06 | Hoffmann-La Roche Inc. | Triazolobenzazepines and processes for their production |
| DE19824673A1 (de) * | 1998-05-26 | 1999-12-02 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3876634A (en) * | 1970-10-30 | 1975-04-08 | Takeda Chemical Industries Ltd | Bendodiazepine derivatives |
| US3853882A (en) * | 1972-11-16 | 1974-12-10 | Upjohn Co | 2,9-DIHYDRO-{8 c,f{9 -S-TRIAZOLO{8 4,3-a{9 AZEPIN-3-ONES |
-
1974
- 1974-09-07 DE DE2442987A patent/DE2442987A1/de not_active Withdrawn
- 1974-09-10 CH CH1232274A patent/CH615435A5/de not_active IP Right Cessation
- 1974-09-11 US US05/505,088 patent/US4002638A/en not_active Expired - Lifetime
- 1974-09-13 FR FR7430980A patent/FR2243700B1/fr not_active Expired
- 1974-09-13 NL NL7412222A patent/NL7412222A/xx unknown
- 1974-09-13 GB GB3999174A patent/GB1453910A/en not_active Expired
- 1974-09-13 BE BE148502A patent/BE819893A/xx unknown
- 1974-09-16 CA CA209,274A patent/CA1062256A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1453910A (en) | 1976-10-27 |
| DE2442987A1 (de) | 1975-03-20 |
| US4002638A (en) | 1977-01-11 |
| CH615435A5 (en, 2012) | 1980-01-31 |
| NL7412222A (nl) | 1975-03-18 |
| BE819893A (fr) | 1975-03-13 |
| FR2243700A1 (en, 2012) | 1975-04-11 |
| FR2243700B1 (en, 2012) | 1978-07-21 |
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