DE2735158A1 - Triazolbenzazepinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen - Google Patents
Triazolbenzazepinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungenInfo
- Publication number
- DE2735158A1 DE2735158A1 DE19772735158 DE2735158A DE2735158A1 DE 2735158 A1 DE2735158 A1 DE 2735158A1 DE 19772735158 DE19772735158 DE 19772735158 DE 2735158 A DE2735158 A DE 2735158A DE 2735158 A1 DE2735158 A1 DE 2735158A1
- Authority
- DE
- Germany
- Prior art keywords
- triazolo
- benzazepine
- formula
- deep
- methylthio
- 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- Withdrawn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
- -1 TRIAZOLE BENZAZEPINE DERIVATIVES Chemical class 0.000 title claims description 72
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- RVQIESIGBRFTHT-UHFFFAOYSA-N 3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2CC2=CC=CC=C21 RVQIESIGBRFTHT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 239000012435 aralkylating agent Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- YEDIWYRGAGPJBT-UHFFFAOYSA-N 3-methylsulfanyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(SC)=NN=C2C1C1=CC=CC=C1 YEDIWYRGAGPJBT-UHFFFAOYSA-N 0.000 claims description 5
- ACVORYUPDXMBQD-UHFFFAOYSA-N 3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2CC2=CC=CC=C21 ACVORYUPDXMBQD-UHFFFAOYSA-N 0.000 claims description 5
- AFJYPTHUEIWEBN-UHFFFAOYSA-N 8-chloro-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2CC2=CC=C(Cl)C=C21 AFJYPTHUEIWEBN-UHFFFAOYSA-N 0.000 claims description 5
- YXFPHSOMYDVYMU-UHFFFAOYSA-N 8-methyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2CC2=CC=C(C)C=C21 YXFPHSOMYDVYMU-UHFFFAOYSA-N 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- MPRVKFWTLHDBFD-UHFFFAOYSA-N 11-methyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(C)C2=CC=CC=C21 MPRVKFWTLHDBFD-UHFFFAOYSA-N 0.000 claims description 4
- KEAGMSGUYOLEJC-UHFFFAOYSA-N 3-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2CC2=CC=CC=C21 KEAGMSGUYOLEJC-UHFFFAOYSA-N 0.000 claims description 4
- IOFXQUCFYGGFMY-UHFFFAOYSA-N 8-chloro-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2CC2=CC=C(Cl)C=C21 IOFXQUCFYGGFMY-UHFFFAOYSA-N 0.000 claims description 4
- RMLFDKUGEDZEOS-UHFFFAOYSA-N 8-methoxy-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC(OC)=CC=C2CC2=NN=C(SC)N21 RMLFDKUGEDZEOS-UHFFFAOYSA-N 0.000 claims description 4
- DDTPPUQXTNDZNO-UHFFFAOYSA-N 9-methoxy-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2CC2=CC(OC)=CC=C21 DDTPPUQXTNDZNO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- UKVXZIVGJRRPOD-UHFFFAOYSA-N 11-methyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)C2=NN=C(S(C)(=O)=O)N21 UKVXZIVGJRRPOD-UHFFFAOYSA-N 0.000 claims description 3
- FLFVQXOEZNFNIL-UHFFFAOYSA-N 11-methylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=C)C2=CC=CC=C21 FLFVQXOEZNFNIL-UHFFFAOYSA-N 0.000 claims description 3
- UNVVGCAFSITXOS-UHFFFAOYSA-N 11-methylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2C(=C)C2=CC=CC=C21 UNVVGCAFSITXOS-UHFFFAOYSA-N 0.000 claims description 3
- KMNMJQPLETWAQJ-UHFFFAOYSA-N 3,9-dimethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2CC2=CC(OC)=CC=C21 KMNMJQPLETWAQJ-UHFFFAOYSA-N 0.000 claims description 3
- XZWRYUPEZNZNIO-UHFFFAOYSA-N 3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(SC)N21 XZWRYUPEZNZNIO-UHFFFAOYSA-N 0.000 claims description 3
- HQUZPEZUJNRQGP-UHFFFAOYSA-N 3-methylsulfonyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(S(=O)(=O)C)=NN=C2C1C1=CC=CC=C1 HQUZPEZUJNRQGP-UHFFFAOYSA-N 0.000 claims description 3
- BIKUJDUEAYPCCH-UHFFFAOYSA-N 3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2CC2=CC=CC=C21 BIKUJDUEAYPCCH-UHFFFAOYSA-N 0.000 claims description 3
- ACNGTSHGGPPRGE-UHFFFAOYSA-N 6-methyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CN2C(SC)=NN=C2CC2=CC=CC=C21 ACNGTSHGGPPRGE-UHFFFAOYSA-N 0.000 claims description 3
- QFWGWMUJXDDXET-UHFFFAOYSA-N 8-methoxy-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC(OC)=CC=C2CC2=NN=C(S(C)(=O)=O)N21 QFWGWMUJXDDXET-UHFFFAOYSA-N 0.000 claims description 3
- DIJDGVPINNCUEP-UHFFFAOYSA-N 8-methyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC(C)=CC=C2CC2=NN=C(S(C)(=O)=O)N21 DIJDGVPINNCUEP-UHFFFAOYSA-N 0.000 claims description 3
- FLAQYQFFMWSKRL-UHFFFAOYSA-N 9-methoxy-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2CC2=CC(OC)=CC=C21 FLAQYQFFMWSKRL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- NYRUQCJPKVMWIR-UHFFFAOYSA-N 3,8-dimethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2CC2=CC=C(OC)C=C21 NYRUQCJPKVMWIR-UHFFFAOYSA-N 0.000 claims description 2
- HGISNLIVVZRSQI-UHFFFAOYSA-N 3-ethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC=CC=C21 HGISNLIVVZRSQI-UHFFFAOYSA-N 0.000 claims description 2
- WBCPSEHAHLOGDN-UHFFFAOYSA-N 3-ethylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SCC)=NN=C2CC2=CC=CC=C21 WBCPSEHAHLOGDN-UHFFFAOYSA-N 0.000 claims description 2
- DQCWSIYGFFPBHK-UHFFFAOYSA-N 3-ethylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)CC)=NN=C2CC2=CC=CC=C21 DQCWSIYGFFPBHK-UHFFFAOYSA-N 0.000 claims description 2
- CVGQUZWXSWUMMT-UHFFFAOYSA-N 3-methoxy-11-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(C)C2=CC=CC=C21 CVGQUZWXSWUMMT-UHFFFAOYSA-N 0.000 claims description 2
- AWQFOMGLQHZNGP-UHFFFAOYSA-N 3-methoxy-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=C)C2=CC=CC=C21 AWQFOMGLQHZNGP-UHFFFAOYSA-N 0.000 claims description 2
- HQCXJRWMVKKWTJ-UHFFFAOYSA-N 3-methoxy-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(OC)=NN=C2C1C1=CC=CC=C1 HQCXJRWMVKKWTJ-UHFFFAOYSA-N 0.000 claims description 2
- NVBJHWZOEZPVGL-UHFFFAOYSA-N 3-methoxy-8-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2CC2=CC=C(C)C=C21 NVBJHWZOEZPVGL-UHFFFAOYSA-N 0.000 claims description 2
- UYOBGAVTLPSKBN-UHFFFAOYSA-N 3-methoxy-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(OC)N21 UYOBGAVTLPSKBN-UHFFFAOYSA-N 0.000 claims description 2
- KKCMFUVFCVORMP-UHFFFAOYSA-N 3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(S(=O)(=O)C)N21 KKCMFUVFCVORMP-UHFFFAOYSA-N 0.000 claims description 2
- PPRQAJUGVLQQPI-UHFFFAOYSA-N 8-chloro-3-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2CC2=CC=C(Cl)C=C21 PPRQAJUGVLQQPI-UHFFFAOYSA-N 0.000 claims description 2
- ZZALQYQHIQQLTI-UHFFFAOYSA-N 8-chloro-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(Cl)=CC=C2C(=O)C2=NN=C(SC)N21 ZZALQYQHIQQLTI-UHFFFAOYSA-N 0.000 claims description 2
- QHBPASLXKIYMTE-UHFFFAOYSA-N 8-chloro-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2CC2=CC=C(Cl)C=C21 QHBPASLXKIYMTE-UHFFFAOYSA-N 0.000 claims description 2
- CYYATTKKCPRMKI-UHFFFAOYSA-N 8-methoxy-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC(OC)=CC=C2CC2=NN=C(S(C)=O)N21 CYYATTKKCPRMKI-UHFFFAOYSA-N 0.000 claims description 2
- ILPPHEGPVJZIGH-UHFFFAOYSA-N 8-methyl-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(C)=CC=C2C(=O)C2=NN=C(SC)N21 ILPPHEGPVJZIGH-UHFFFAOYSA-N 0.000 claims description 2
- SVJMWLLLMLHSDO-UHFFFAOYSA-N 8-methyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC(C)=CC=C2CC2=NN=C(S(C)=O)N21 SVJMWLLLMLHSDO-UHFFFAOYSA-N 0.000 claims description 2
- FPIUPLBBRYGJPB-UHFFFAOYSA-N 9-methoxy-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)=O)=NN=C2CC2=CC(OC)=CC=C21 FPIUPLBBRYGJPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
- 238000002844 melting Methods 0.000 description 75
- 230000008018 melting Effects 0.000 description 75
- 238000001953 recrystallisation Methods 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 239000013078 crystal Substances 0.000 description 60
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 55
- 238000000921 elemental analysis Methods 0.000 description 50
- 239000002904 solvent Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 33
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 29
- 239000000243 solution Substances 0.000 description 26
- 239000011734 sodium Substances 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 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 235000010265 sodium sulphite Nutrition 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- SYIUPRKONIOYIL-UHFFFAOYSA-N 1-benzazepin-3-one Chemical compound N1=CC(=O)C=CC2=CC=CC=C21 SYIUPRKONIOYIL-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 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 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 229940035676 analgesics Drugs 0.000 description 5
- 239000000730 antalgic agent Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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 4
- DJTHSRALXGPFIO-UHFFFAOYSA-N 3-benzyl-4-(2,2-diethoxyethyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OCC)OCC)C(CC=2C=CC=CC=2)=N1 DJTHSRALXGPFIO-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 229940035363 muscle relaxants Drugs 0.000 description 4
- 239000003158 myorelaxant agent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical class NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 description 3
- LCMYLIKMCLNTKX-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-4-(2,2-diethoxyethyl)-5-methylsulfanyl-1,2,4-triazole Chemical compound N1=C(SC)N(CC(OCC)OCC)C(CC=2C=CC(Cl)=CC=2)=N1 LCMYLIKMCLNTKX-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- VXAXUVCCBGOVLW-UHFFFAOYSA-N 3-benzyl-4-(2,2-diethoxyethyl)-5-methylsulfanyl-1,2,4-triazole Chemical compound N1=C(SC)N(CC(OCC)OCC)C(CC=2C=CC=CC=2)=N1 VXAXUVCCBGOVLW-UHFFFAOYSA-N 0.000 description 3
- PJENGMLQBLNXHQ-UHFFFAOYSA-N 3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(S(=O)C)N21 PJENGMLQBLNXHQ-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000137 polyphosphoric acid Chemical class 0.000 description 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- ZZVICZHVZHMXJS-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)-3-[(2,2-diphenylacetyl)amino]thiourea Chemical compound C=1C=CC=CC=1C(C(=O)NNC(=S)NCC(OCC)OCC)C1=CC=CC=C1 ZZVICZHVZHMXJS-UHFFFAOYSA-N 0.000 description 2
- RDQBODXZDWPCCM-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)-3-[[2-(3-methoxyphenyl)acetyl]amino]thiourea Chemical compound CCOC(OCC)CNC(=S)NNC(=O)CC1=CC=CC(OC)=C1 RDQBODXZDWPCCM-UHFFFAOYSA-N 0.000 description 2
- KZOSCGDZMKACAB-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)-3-[[2-(4-methoxyphenyl)acetyl]amino]thiourea Chemical compound CCOC(OCC)CNC(=S)NNC(=O)CC1=CC=C(OC)C=C1 KZOSCGDZMKACAB-UHFFFAOYSA-N 0.000 description 2
- IMCUASVCQKYODV-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)-3-[[2-(4-methylphenyl)acetyl]amino]thiourea Chemical compound CCOC(OCC)CNC(=S)NNC(=O)CC1=CC=C(C)C=C1 IMCUASVCQKYODV-UHFFFAOYSA-N 0.000 description 2
- GEBCWIOIPJTNLP-UHFFFAOYSA-N 1-(3-benzyl-5-methylsulfanyl-1,2,4-triazol-4-yl)propan-2-one Chemical compound CC(=O)CN1C(SC)=NN=C1CC1=CC=CC=C1 GEBCWIOIPJTNLP-UHFFFAOYSA-N 0.000 description 2
- AIJCCFXWTFQRFY-UHFFFAOYSA-N 1-(3-benzyl-5-sulfanylidene-1h-1,2,4-triazol-4-yl)propan-2-one Chemical compound N1C(=S)N(CC(=O)C)C(CC=2C=CC=CC=2)=N1 AIJCCFXWTFQRFY-UHFFFAOYSA-N 0.000 description 2
- FLZXCDLWPHCMQW-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)acetyl]amino]-3-(2,2-diethoxyethyl)thiourea Chemical compound CCOC(OCC)CNC(=S)NNC(=O)CC1=CC=C(Cl)C=C1 FLZXCDLWPHCMQW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- LBVZKBCZRFLVKD-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-4-(2,2-diethoxyethyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OCC)OCC)C(CC=2C=CC(Cl)=CC=2)=N1 LBVZKBCZRFLVKD-UHFFFAOYSA-N 0.000 description 2
- PIMOLFYSPXZEAY-UHFFFAOYSA-N 3-benzhydryl-4-(2,2-diethoxyethyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OCC)OCC)C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 PIMOLFYSPXZEAY-UHFFFAOYSA-N 0.000 description 2
- SAICKWVSSCTFMH-UHFFFAOYSA-N 3-benzhydryl-4-(2,2-diethoxyethyl)-5-methylsulfanyl-1,2,4-triazole Chemical compound CCOC(OCC)CN1C(SC)=NN=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 SAICKWVSSCTFMH-UHFFFAOYSA-N 0.000 description 2
- IRFPUTBIOBTARV-UHFFFAOYSA-N 3-benzyl-4-[(2-methyl-1,3-dioxolan-2-yl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1CC1=NNC(=S)N1CC1(C)OCCO1 IRFPUTBIOBTARV-UHFFFAOYSA-N 0.000 description 2
- CZKNURUSJAYBFY-UHFFFAOYSA-N 4-(2,2-diethoxyethyl)-3-[(3-methoxyphenyl)methyl]-5-methylsulfanyl-1,2,4-triazole Chemical compound N1=C(SC)N(CC(OCC)OCC)C(CC=2C=C(OC)C=CC=2)=N1 CZKNURUSJAYBFY-UHFFFAOYSA-N 0.000 description 2
- QTOMDHKSIZKWSR-UHFFFAOYSA-N 4-(2,2-diethoxyethyl)-3-[(4-methoxyphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OCC)OCC)C(CC=2C=CC(OC)=CC=2)=N1 QTOMDHKSIZKWSR-UHFFFAOYSA-N 0.000 description 2
- PSXYDMPGGYPHSC-UHFFFAOYSA-N 4-(2,2-diethoxyethyl)-3-[(4-methylphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OCC)OCC)C(CC=2C=CC(C)=CC=2)=N1 PSXYDMPGGYPHSC-UHFFFAOYSA-N 0.000 description 2
- LDOFDRQFIUGCJF-UHFFFAOYSA-N 4-(2,2-diethoxyethyl)-3-[(4-methylphenyl)methyl]-5-methylsulfanyl-1,2,4-triazole Chemical compound N1=C(SC)N(CC(OCC)OCC)C(CC=2C=CC(C)=CC=2)=N1 LDOFDRQFIUGCJF-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000000112 Myalgia Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HPRRRCJCXROIAC-UHFFFAOYSA-N 1,1-diethoxy-2-isothiocyanatoethane Chemical compound CCOC(OCC)CN=C=S HPRRRCJCXROIAC-UHFFFAOYSA-N 0.000 description 1
- RRGZUAKKNQDSGT-UHFFFAOYSA-N 1-benzazepine-3-thione Chemical compound N1=CC(C=CC2=C1C=CC=C2)=S RRGZUAKKNQDSGT-UHFFFAOYSA-N 0.000 description 1
- RBEIXLNFMZLTJD-UHFFFAOYSA-N 10-chloro-3-ethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=C(Cl)C=CC=C21 RBEIXLNFMZLTJD-UHFFFAOYSA-N 0.000 description 1
- BYZIXIGCWKPSQD-UHFFFAOYSA-N 10-chloro-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2CC2=C(Cl)C=CC=C21 BYZIXIGCWKPSQD-UHFFFAOYSA-N 0.000 description 1
- FXKQJBCXDCHFHS-UHFFFAOYSA-N 10-chloro-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2CC2=C(Cl)C=CC=C21 FXKQJBCXDCHFHS-UHFFFAOYSA-N 0.000 description 1
- CLAVTMMIVIYDTR-UHFFFAOYSA-N 10-chloro-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2CC2=C(Cl)C=CC=C21 CLAVTMMIVIYDTR-UHFFFAOYSA-N 0.000 description 1
- MQMFODBUOKOYGS-UHFFFAOYSA-N 11,11-dimethyl-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(SC)N21 MQMFODBUOKOYGS-UHFFFAOYSA-N 0.000 description 1
- IMBDVDBCPNSCBC-UHFFFAOYSA-N 11,11-dimethyl-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(S(=O)C)N21 IMBDVDBCPNSCBC-UHFFFAOYSA-N 0.000 description 1
- XGDJUNRGJRXZMG-UHFFFAOYSA-N 11,11-dimethyl-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(S(C)(=O)=O)N21 XGDJUNRGJRXZMG-UHFFFAOYSA-N 0.000 description 1
- KGMFEBDGNUOAGQ-UHFFFAOYSA-N 11-benzyl-3-ethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(OCC)=NN=C2C1CC1=CC=CC=C1 KGMFEBDGNUOAGQ-UHFFFAOYSA-N 0.000 description 1
- QBWPKKTYMHIHAE-UHFFFAOYSA-N 11-benzyl-3-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(OC)=NN=C2C1CC1=CC=CC=C1 QBWPKKTYMHIHAE-UHFFFAOYSA-N 0.000 description 1
- OOBLYWDMPOLSAW-UHFFFAOYSA-N 11-benzyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(SC)=NN=C2C1CC1=CC=CC=C1 OOBLYWDMPOLSAW-UHFFFAOYSA-N 0.000 description 1
- YUOCULWMIQANGM-UHFFFAOYSA-N 11-benzyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(S(=O)C)=NN=C2C1CC1=CC=CC=C1 YUOCULWMIQANGM-UHFFFAOYSA-N 0.000 description 1
- MCOCMMUNYURDKD-UHFFFAOYSA-N 11-benzyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(S(=O)(=O)C)=NN=C2C1CC1=CC=CC=C1 MCOCMMUNYURDKD-UHFFFAOYSA-N 0.000 description 1
- HYAZFGYHJYUBKK-UHFFFAOYSA-N 11-butyl-3-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CCCC)C2=NN=C(OC)N21 HYAZFGYHJYUBKK-UHFFFAOYSA-N 0.000 description 1
- AEIMTNJTILZQOG-UHFFFAOYSA-N 11-butyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CCCC)C2=NN=C(SC)N21 AEIMTNJTILZQOG-UHFFFAOYSA-N 0.000 description 1
- JDEBWMBMCBHXPF-UHFFFAOYSA-N 11-ethyl-11-methyl-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)(C)C2=NN=C(SC)N21 JDEBWMBMCBHXPF-UHFFFAOYSA-N 0.000 description 1
- HMSGRQWZZYJSFG-UHFFFAOYSA-N 11-ethyl-11-methyl-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)(C)C2=NN=C(S(C)=O)N21 HMSGRQWZZYJSFG-UHFFFAOYSA-N 0.000 description 1
- VOSRZYCZPLJWOK-UHFFFAOYSA-N 11-ethyl-11-methyl-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)(C)C2=NN=C(S(C)(=O)=O)N21 VOSRZYCZPLJWOK-UHFFFAOYSA-N 0.000 description 1
- GCNKTUNTBCSALA-UHFFFAOYSA-N 11-ethyl-3-ethylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SCC)=NN=C2C(CC)C2=CC=CC=C21 GCNKTUNTBCSALA-UHFFFAOYSA-N 0.000 description 1
- JUAYWNDARXPBPR-UHFFFAOYSA-N 11-ethyl-3-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)C2=NN=C(OC)N21 JUAYWNDARXPBPR-UHFFFAOYSA-N 0.000 description 1
- KSVGEDLKEPRJFC-UHFFFAOYSA-N 11-ethyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)C2=NN=C(SC)N21 KSVGEDLKEPRJFC-UHFFFAOYSA-N 0.000 description 1
- MYMSKUUJJDJJTN-UHFFFAOYSA-N 11-ethyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)C2=NN=C(S(C)=O)N21 MYMSKUUJJDJJTN-UHFFFAOYSA-N 0.000 description 1
- JNKYISHBFDNSKM-UHFFFAOYSA-N 11-ethyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)C2=NN=C(S(C)(=O)=O)N21 JNKYISHBFDNSKM-UHFFFAOYSA-N 0.000 description 1
- ALOMMVINAJTZKT-UHFFFAOYSA-N 11-ethyl-3-propan-2-ylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CC)C2=NN=C(SC(C)C)N21 ALOMMVINAJTZKT-UHFFFAOYSA-N 0.000 description 1
- KWDLIFSMTZSRBT-UHFFFAOYSA-N 11-ethylidene-3-methoxy-8-methyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=CC)C2=CC=C(C)C=C21 KWDLIFSMTZSRBT-UHFFFAOYSA-N 0.000 description 1
- VRWDDPBFFPSJGV-UHFFFAOYSA-N 11-ethylidene-3-methoxy-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=CC)C2=CC=CC=C21 VRWDDPBFFPSJGV-UHFFFAOYSA-N 0.000 description 1
- JFPZVJJMGRYPNJ-UHFFFAOYSA-N 11-ethylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=CC)C2=CC=CC=C21 JFPZVJJMGRYPNJ-UHFFFAOYSA-N 0.000 description 1
- GKQOPJXCPBGNCN-UHFFFAOYSA-N 11-ethylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(=CC)C2=NN=C(S(C)=O)N21 GKQOPJXCPBGNCN-UHFFFAOYSA-N 0.000 description 1
- DVOPEXOFJBLLFV-UHFFFAOYSA-N 11-ethylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(=CC)C2=NN=C(S(C)(=O)=O)N21 DVOPEXOFJBLLFV-UHFFFAOYSA-N 0.000 description 1
- JYPYRVXIVDQCAN-UHFFFAOYSA-N 11-methyl-2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CC2=CC=CC=C2C(C)C2=NNC(=O)N21 JYPYRVXIVDQCAN-UHFFFAOYSA-N 0.000 description 1
- NCIZNMPVQVWEPN-UHFFFAOYSA-N 11-methyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)C2=NN=C(S(C)=O)N21 NCIZNMPVQVWEPN-UHFFFAOYSA-N 0.000 description 1
- KPIGPUBHYKCBEI-UHFFFAOYSA-N 11-methyl-3-propan-2-yloxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC(C)C)=NN=C2C(C)C2=CC=CC=C21 KPIGPUBHYKCBEI-UHFFFAOYSA-N 0.000 description 1
- OHOBBUKFYJGDAB-UHFFFAOYSA-N 11-methyl-3-propan-2-ylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC(C)C)=NN=C2C(C)C2=CC=CC=C21 OHOBBUKFYJGDAB-UHFFFAOYSA-N 0.000 description 1
- ZVUULZKHTNTIIC-UHFFFAOYSA-N 11-methyl-3-propan-2-ylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C(C)C)=NN=C2C(C)C2=CC=CC=C21 ZVUULZKHTNTIIC-UHFFFAOYSA-N 0.000 description 1
- NXUMHMSATOTJBX-UHFFFAOYSA-N 11-methylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2C(=C)C2=CC=CC=C21 NXUMHMSATOTJBX-UHFFFAOYSA-N 0.000 description 1
- DOPGIQVHBVRZCR-UHFFFAOYSA-N 11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C=NN=C2C1C1=CC=CC=C1 DOPGIQVHBVRZCR-UHFFFAOYSA-N 0.000 description 1
- SVOONDBCNPDXEI-UHFFFAOYSA-N 11-phenyl-2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C12=CC=CC=C2C=CN2C(=O)NN=C2C1C1=CC=CC=C1 SVOONDBCNPDXEI-UHFFFAOYSA-N 0.000 description 1
- HNFVYSOTJKOXKV-UHFFFAOYSA-N 11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2CC2=NN=CN21 HNFVYSOTJKOXKV-UHFFFAOYSA-N 0.000 description 1
- RYMYEECKBLSAHO-UHFFFAOYSA-N 2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepine-3-thione Chemical compound C1=CN2C(=S)NN=C2CC2=CC=CC=C21 RYMYEECKBLSAHO-UHFFFAOYSA-N 0.000 description 1
- YBBSKAGTEPBSNK-UHFFFAOYSA-N 2,2-diphenylacetohydrazide Chemical compound C=1C=CC=CC=1C(C(=O)NN)C1=CC=CC=C1 YBBSKAGTEPBSNK-UHFFFAOYSA-N 0.000 description 1
- XEALVGVRTCEVES-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetohydrazide Chemical compound COC1=CC=CC(CC(=O)NN)=C1 XEALVGVRTCEVES-UHFFFAOYSA-N 0.000 description 1
- ZXTSFZRZKFXXRG-UHFFFAOYSA-N 2-(4-chlorophenyl)acetohydrazide Chemical compound NNC(=O)CC1=CC=C(Cl)C=C1 ZXTSFZRZKFXXRG-UHFFFAOYSA-N 0.000 description 1
- BCHPFJXZQWWCCZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetohydrazide Chemical compound COC1=CC=C(CC(=O)NN)C=C1 BCHPFJXZQWWCCZ-UHFFFAOYSA-N 0.000 description 1
- WIVOCOQKIVAVRM-UHFFFAOYSA-N 2-(4-methylphenyl)acetohydrazide Chemical compound CC1=CC=C(CC(=O)NN)C=C1 WIVOCOQKIVAVRM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AJFUTCZBTOLZJK-UHFFFAOYSA-N 2-phenylpropanehydrazide Chemical compound NNC(=O)C(C)C1=CC=CC=C1 AJFUTCZBTOLZJK-UHFFFAOYSA-N 0.000 description 1
- WXGHXJFJQHUPOE-UHFFFAOYSA-N 3,8-dimethoxy-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=C)C2=CC=C(OC)C=C21 WXGHXJFJQHUPOE-UHFFFAOYSA-N 0.000 description 1
- VGYPLETXTADKCI-UHFFFAOYSA-N 3,9-dimethoxy-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=C)C2=CC(OC)=CC=C21 VGYPLETXTADKCI-UHFFFAOYSA-N 0.000 description 1
- KNMBXDDWSCGNIX-UHFFFAOYSA-N 3-(2-phenylethoxy)-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound N=1N=C2CC3=CC=CC=C3C=CN2C=1OCCC1=CC=CC=C1 KNMBXDDWSCGNIX-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- QPEQDFGRIWGAJV-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-4-(2,2-diethoxyethyl)-1,2,4-triazole Chemical compound ClC1=CC=C(CC2=NN=CN2CC(OCC)OCC)C=C1 QPEQDFGRIWGAJV-UHFFFAOYSA-N 0.000 description 1
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 description 1
- MZVFYVWANFKQGG-UHFFFAOYSA-N 3-benzylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound N=1N=C2CC3=CC=CC=C3C=CN2C=1S(=O)CC1=CC=CC=C1 MZVFYVWANFKQGG-UHFFFAOYSA-N 0.000 description 1
- WIKJDKWAPTZNTG-UHFFFAOYSA-N 3-benzylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound N=1N=C2CC3=CC=CC=C3C=CN2C=1S(=O)(=O)CC1=CC=CC=C1 WIKJDKWAPTZNTG-UHFFFAOYSA-N 0.000 description 1
- YYYBOCXXVUVIMQ-UHFFFAOYSA-N 3-bromo-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(Br)=NN=C2CC2=CC=CC=C21 YYYBOCXXVUVIMQ-UHFFFAOYSA-N 0.000 description 1
- VWHUJAPKWYYHLG-UHFFFAOYSA-N 3-butoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCCCC)=NN=C2CC2=CC=CC=C21 VWHUJAPKWYYHLG-UHFFFAOYSA-N 0.000 description 1
- DOEGIZCOVWHRLO-UHFFFAOYSA-N 3-butylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SCCCC)=NN=C2CC2=CC=CC=C21 DOEGIZCOVWHRLO-UHFFFAOYSA-N 0.000 description 1
- UWYHXFRXHIQOKF-UHFFFAOYSA-N 3-butylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)CCCC)=NN=C2CC2=CC=CC=C21 UWYHXFRXHIQOKF-UHFFFAOYSA-N 0.000 description 1
- ZZDHPYHDRZDAPT-UHFFFAOYSA-N 3-butylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)CCCC)=NN=C2CC2=CC=CC=C21 ZZDHPYHDRZDAPT-UHFFFAOYSA-N 0.000 description 1
- UUZRLQJRPGWUIO-UHFFFAOYSA-N 3-ethoxy-11,11-dimethyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(OCC)N21 UUZRLQJRPGWUIO-UHFFFAOYSA-N 0.000 description 1
- NGGSNUJFRZKLLL-UHFFFAOYSA-N 3-ethoxy-11-ethyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2C(CC)C2=CC=CC=C21 NGGSNUJFRZKLLL-UHFFFAOYSA-N 0.000 description 1
- NXQDQAZZQUAURV-UHFFFAOYSA-N 3-ethoxy-11-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2C(C)C2=CC=CC=C21 NXQDQAZZQUAURV-UHFFFAOYSA-N 0.000 description 1
- BMUYGGVMGVSZBI-UHFFFAOYSA-N 3-ethoxy-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2C(=C)C2=CC=CC=C21 BMUYGGVMGVSZBI-UHFFFAOYSA-N 0.000 description 1
- UGROZIQIGBLKRB-UHFFFAOYSA-N 3-ethoxy-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(OCC)=NN=C2C1C1=CC=CC=C1 UGROZIQIGBLKRB-UHFFFAOYSA-N 0.000 description 1
- OLCCQBWRSCHWMX-UHFFFAOYSA-N 3-ethoxy-11-propyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CCC)C2=NN=C(OCC)N21 OLCCQBWRSCHWMX-UHFFFAOYSA-N 0.000 description 1
- GTNLGPNFNQKURH-UHFFFAOYSA-N 3-ethoxy-5,11-dimethyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=C(C)N2C(OCC)=NN=C2C(C)C2=CC=CC=C21 GTNLGPNFNQKURH-UHFFFAOYSA-N 0.000 description 1
- HIJJMAXHBAYILT-UHFFFAOYSA-N 3-ethoxy-5-methyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=C(C)N2C(OCC)=NN=C2C1C1=CC=CC=C1 HIJJMAXHBAYILT-UHFFFAOYSA-N 0.000 description 1
- DBMNAPCEQNBBFU-UHFFFAOYSA-N 3-ethoxy-5-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=C(C)N2C(OCC)=NN=C2CC2=CC=CC=C21 DBMNAPCEQNBBFU-UHFFFAOYSA-N 0.000 description 1
- JYRAOOVYAFOALU-UHFFFAOYSA-N 3-ethoxy-6-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CN2C(OCC)=NN=C2CC2=CC=CC=C21 JYRAOOVYAFOALU-UHFFFAOYSA-N 0.000 description 1
- OXQXPCYSCHRDBQ-UHFFFAOYSA-N 3-ethoxy-6-methyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=C(C)C2=CC=CC=C2C(=O)C2=NN=C(OCC)N21 OXQXPCYSCHRDBQ-UHFFFAOYSA-N 0.000 description 1
- MDOBLYCCPJNLES-UHFFFAOYSA-N 3-ethoxy-8,9-dimethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC(OC)=C(OC)C=C21 MDOBLYCCPJNLES-UHFFFAOYSA-N 0.000 description 1
- SHKKJTLBQIULQN-UHFFFAOYSA-N 3-ethoxy-8-(trifluoromethyl)-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC=C(C(F)(F)F)C=C21 SHKKJTLBQIULQN-UHFFFAOYSA-N 0.000 description 1
- RLAYYRCQNYUVCB-UHFFFAOYSA-N 3-ethoxy-8-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC=C(OC)C=C21 RLAYYRCQNYUVCB-UHFFFAOYSA-N 0.000 description 1
- YWUXLBWXFKGCBD-UHFFFAOYSA-N 3-ethoxy-8-methoxy-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(OC)=CC=C2C(=O)C2=NN=C(OCC)N21 YWUXLBWXFKGCBD-UHFFFAOYSA-N 0.000 description 1
- JELUPJCZKDBAAR-UHFFFAOYSA-N 3-ethoxy-8-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC=C(C)C=C21 JELUPJCZKDBAAR-UHFFFAOYSA-N 0.000 description 1
- QOJAETZBCMJMLP-UHFFFAOYSA-N 3-ethoxy-8-methyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(C)=CC=C2C(=O)C2=NN=C(OCC)N21 QOJAETZBCMJMLP-UHFFFAOYSA-N 0.000 description 1
- XWVRSPLDNFIZAA-UHFFFAOYSA-N 3-ethoxy-9-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC(OC)=CC=C21 XWVRSPLDNFIZAA-UHFFFAOYSA-N 0.000 description 1
- NVOZJOCJQACKOZ-UHFFFAOYSA-N 3-ethoxy-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(OCC)N21 NVOZJOCJQACKOZ-UHFFFAOYSA-N 0.000 description 1
- LSMVVAGUJIWZSS-UHFFFAOYSA-N 3-ethylsulfanyl-11,11-dimethyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(SCC)N21 LSMVVAGUJIWZSS-UHFFFAOYSA-N 0.000 description 1
- FBQSVENDIXKFBP-UHFFFAOYSA-N 3-ethylsulfanyl-11-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SCC)=NN=C2C(C)C2=CC=CC=C21 FBQSVENDIXKFBP-UHFFFAOYSA-N 0.000 description 1
- UONQVZJGIVRNSZ-UHFFFAOYSA-N 3-ethylsulfanyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(SCC)=NN=C2C1C1=CC=CC=C1 UONQVZJGIVRNSZ-UHFFFAOYSA-N 0.000 description 1
- BPYMTCUTCCUJLA-UHFFFAOYSA-N 3-ethylsulfanyl-11-propan-2-yl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SCC)=NN=C2C(C(C)C)C2=CC=CC=C21 BPYMTCUTCCUJLA-UHFFFAOYSA-N 0.000 description 1
- ZKFFLFVPDNVRQT-UHFFFAOYSA-N 3-ethylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(SCC)N21 ZKFFLFVPDNVRQT-UHFFFAOYSA-N 0.000 description 1
- JIIIZNHWDOBAKC-UHFFFAOYSA-N 3-ethylsulfinyl-11,11-dimethyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(S(=O)CC)N21 JIIIZNHWDOBAKC-UHFFFAOYSA-N 0.000 description 1
- YRHQCBCBHDOUPR-UHFFFAOYSA-N 3-ethylsulfinyl-11-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)CC)=NN=C2C(C)C2=CC=CC=C21 YRHQCBCBHDOUPR-UHFFFAOYSA-N 0.000 description 1
- FPMKBGQAYCXFNU-UHFFFAOYSA-N 3-ethylsulfinyl-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)CC)=NN=C2C(=C)C2=CC=CC=C21 FPMKBGQAYCXFNU-UHFFFAOYSA-N 0.000 description 1
- BOADBYDARUIWHY-UHFFFAOYSA-N 3-ethylsulfinyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(S(=O)CC)=NN=C2C1C1=CC=CC=C1 BOADBYDARUIWHY-UHFFFAOYSA-N 0.000 description 1
- VYIZTMPSAPJNPX-UHFFFAOYSA-N 3-ethylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(S(=O)CC)N21 VYIZTMPSAPJNPX-UHFFFAOYSA-N 0.000 description 1
- NWFVDAGRLUJTDT-UHFFFAOYSA-N 3-ethylsulfonyl-11,11-dimethyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(S(=O)(=O)CC)N21 NWFVDAGRLUJTDT-UHFFFAOYSA-N 0.000 description 1
- HMDLIYHLUDSPKF-UHFFFAOYSA-N 3-ethylsulfonyl-11-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)CC)=NN=C2C(C)C2=CC=CC=C21 HMDLIYHLUDSPKF-UHFFFAOYSA-N 0.000 description 1
- RMIQILDYOQTEQD-UHFFFAOYSA-N 3-ethylsulfonyl-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)CC)=NN=C2C(=C)C2=CC=CC=C21 RMIQILDYOQTEQD-UHFFFAOYSA-N 0.000 description 1
- FMWBPHCNJADAFB-UHFFFAOYSA-N 3-ethylsulfonyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(S(=O)(=O)CC)=NN=C2C1C1=CC=CC=C1 FMWBPHCNJADAFB-UHFFFAOYSA-N 0.000 description 1
- JCEGHYMHUNWHHM-UHFFFAOYSA-N 3-ethylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)CC)=NN=C2CC2=CC=CC=C21 JCEGHYMHUNWHHM-UHFFFAOYSA-N 0.000 description 1
- XBKODNHIYPTAQX-UHFFFAOYSA-N 3-ethylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(S(=O)(=O)CC)N21 XBKODNHIYPTAQX-UHFFFAOYSA-N 0.000 description 1
- AQWUTDFHNHKOFI-UHFFFAOYSA-N 3-methoxy-11,11-dimethyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C)(C)C2=NN=C(OC)N21 AQWUTDFHNHKOFI-UHFFFAOYSA-N 0.000 description 1
- PZMZHBIBLNQKJW-UHFFFAOYSA-N 3-methoxy-11-propyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CCC)C2=NN=C(OC)N21 PZMZHBIBLNQKJW-UHFFFAOYSA-N 0.000 description 1
- HWUUTNIAIKNPMU-UHFFFAOYSA-N 3-methoxy-11-propylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(=CCC)C2=NN=C(OC)N21 HWUUTNIAIKNPMU-UHFFFAOYSA-N 0.000 description 1
- CWRIRBPCKMFDHT-UHFFFAOYSA-N 3-methoxy-5-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=C(C)N2C(OC)=NN=C2CC2=CC=CC=C21 CWRIRBPCKMFDHT-UHFFFAOYSA-N 0.000 description 1
- FJEZLOHSLFJIQJ-UHFFFAOYSA-N 3-methoxy-6-methyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CN2C(OC)=NN=C2CC2=CC=CC=C21 FJEZLOHSLFJIQJ-UHFFFAOYSA-N 0.000 description 1
- ILBNIZPDFFSHIO-UHFFFAOYSA-N 3-methoxy-8-methyl-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=C)C2=CC=C(C)C=C21 ILBNIZPDFFSHIO-UHFFFAOYSA-N 0.000 description 1
- DBMNEPZGXIZUJS-UHFFFAOYSA-N 3-methylsulfanyl-11-propan-2-yl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(C(C)C)C2=CC=CC=C21 DBMNEPZGXIZUJS-UHFFFAOYSA-N 0.000 description 1
- LOYVTVJZZOWAGO-UHFFFAOYSA-N 3-methylsulfanyl-11-propylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(=CCC)C2=NN=C(SC)N21 LOYVTVJZZOWAGO-UHFFFAOYSA-N 0.000 description 1
- RMLYXCIQKYHTCA-UHFFFAOYSA-N 3-methylsulfanyl-5-propan-2-yl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=C(C(C)C)N2C(SC)=NN=C2CC2=CC=CC=C21 RMLYXCIQKYHTCA-UHFFFAOYSA-N 0.000 description 1
- ORYNJLQHDBISHL-UHFFFAOYSA-N 3-methylsulfanyl-8-(trifluoromethyl)-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(C(F)(F)F)=CC=C2C(=O)C2=NN=C(SC)N21 ORYNJLQHDBISHL-UHFFFAOYSA-N 0.000 description 1
- BHIROAOZBOTFOB-UHFFFAOYSA-N 3-methylsulfinyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=CN2C(S(=O)C)=NN=C2C1C1=CC=CC=C1 BHIROAOZBOTFOB-UHFFFAOYSA-N 0.000 description 1
- OAFJKHCVATUBRM-UHFFFAOYSA-N 3-methylsulfinyl-11-propan-2-yl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C(C)C)C2=NN=C(S(C)=O)N21 OAFJKHCVATUBRM-UHFFFAOYSA-N 0.000 description 1
- DMGOTOHCXADBHB-UHFFFAOYSA-N 3-methylsulfinyl-11-propyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CCC)C2=NN=C(S(C)=O)N21 DMGOTOHCXADBHB-UHFFFAOYSA-N 0.000 description 1
- YFVIFTZAFXZZQM-UHFFFAOYSA-N 3-methylsulfinyl-11-propylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(=CCC)C2=NN=C(S(C)=O)N21 YFVIFTZAFXZZQM-UHFFFAOYSA-N 0.000 description 1
- VQKSDYAYTOXWAH-UHFFFAOYSA-N 3-methylsulfinyl-8-(trifluoromethyl)-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2CC2=CC=C(C(F)(F)F)C=C21 VQKSDYAYTOXWAH-UHFFFAOYSA-N 0.000 description 1
- PCBHDSLXSASQIF-UHFFFAOYSA-N 3-methylsulfinyl-8-(trifluoromethyl)-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(C(F)(F)F)=CC=C2C(=O)C2=NN=C(S(=O)C)N21 PCBHDSLXSASQIF-UHFFFAOYSA-N 0.000 description 1
- HMOHKFZFIUQPPP-UHFFFAOYSA-N 3-methylsulfonyl-11-propan-2-yl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(C(C)C)C2=NN=C(S(C)(=O)=O)N21 HMOHKFZFIUQPPP-UHFFFAOYSA-N 0.000 description 1
- ZBLNYLCAYMUXJY-UHFFFAOYSA-N 3-methylsulfonyl-11-propyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(CCC)C2=NN=C(S(C)(=O)=O)N21 ZBLNYLCAYMUXJY-UHFFFAOYSA-N 0.000 description 1
- JCSDPOZAVJQCLV-UHFFFAOYSA-N 3-methylsulfonyl-11-propylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2C(=CCC)C2=NN=C(S(C)(=O)=O)N21 JCSDPOZAVJQCLV-UHFFFAOYSA-N 0.000 description 1
- IHMIKMKOCNTTFN-UHFFFAOYSA-N 3-methylsulfonyl-8-(trifluoromethyl)-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2CC2=CC=C(C(F)(F)F)C=C21 IHMIKMKOCNTTFN-UHFFFAOYSA-N 0.000 description 1
- YHWQEYGKPKCLGL-UHFFFAOYSA-N 3-methylsulfonyl-8-(trifluoromethyl)-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(C(F)(F)F)=CC=C2C(=O)C2=NN=C(S(=O)(=O)C)N21 YHWQEYGKPKCLGL-UHFFFAOYSA-N 0.000 description 1
- MWOYMAHGPVXRMA-UHFFFAOYSA-N 3-phenylmethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound N=1N=C2CC3=CC=CC=C3C=CN2C=1OCC1=CC=CC=C1 MWOYMAHGPVXRMA-UHFFFAOYSA-N 0.000 description 1
- MXNJTTPRXUEOGB-UHFFFAOYSA-N 3-propan-2-yloxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC(C)C)=NN=C2CC2=CC=CC=C21 MXNJTTPRXUEOGB-UHFFFAOYSA-N 0.000 description 1
- MESIKNINFOGMRW-UHFFFAOYSA-N 3-propan-2-ylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC(C)C)=NN=C2CC2=CC=CC=C21 MESIKNINFOGMRW-UHFFFAOYSA-N 0.000 description 1
- APCMNEJXAOJEBB-UHFFFAOYSA-N 3-propan-2-ylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(SC(C)C)N21 APCMNEJXAOJEBB-UHFFFAOYSA-N 0.000 description 1
- SJELUGWJSXYYJG-UHFFFAOYSA-N 3-propan-2-ylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C(C)C)=NN=C2CC2=CC=CC=C21 SJELUGWJSXYYJG-UHFFFAOYSA-N 0.000 description 1
- HFBVWSSGTFQTED-UHFFFAOYSA-N 3-propan-2-ylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(S(=O)C(C)C)N21 HFBVWSSGTFQTED-UHFFFAOYSA-N 0.000 description 1
- SOXNWXVHDNPUQL-UHFFFAOYSA-N 3-propan-2-ylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C(C)C)=NN=C2CC2=CC=CC=C21 SOXNWXVHDNPUQL-UHFFFAOYSA-N 0.000 description 1
- IGMBQAVEFMTTSZ-UHFFFAOYSA-N 3-propan-2-ylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=NN=C(S(=O)(=O)C(C)C)N21 IGMBQAVEFMTTSZ-UHFFFAOYSA-N 0.000 description 1
- YSBOCPYPWFPOOU-UHFFFAOYSA-N 3-propoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCCC)=NN=C2CC2=CC=CC=C21 YSBOCPYPWFPOOU-UHFFFAOYSA-N 0.000 description 1
- AXHRBDZLEWFUQP-UHFFFAOYSA-N 3-propylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SCCC)=NN=C2CC2=CC=CC=C21 AXHRBDZLEWFUQP-UHFFFAOYSA-N 0.000 description 1
- ZNYIGLLOPCQEQY-UHFFFAOYSA-N 3-propylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)CCC)=NN=C2CC2=CC=CC=C21 ZNYIGLLOPCQEQY-UHFFFAOYSA-N 0.000 description 1
- JBYYBLDXWWQEHB-UHFFFAOYSA-N 3-propylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)CCC)=NN=C2CC2=CC=CC=C21 JBYYBLDXWWQEHB-UHFFFAOYSA-N 0.000 description 1
- CSFFXWTVLPAKSE-UHFFFAOYSA-N 4-(2,2-diethoxyethyl)-3-[(3-methoxyphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OCC)OCC)C(CC=2C=C(OC)C=CC=2)=N1 CSFFXWTVLPAKSE-UHFFFAOYSA-N 0.000 description 1
- TZVKIWHRWPDDQG-UHFFFAOYSA-N 4-(2,2-diethoxyethyl)-3-[(4-methoxyphenyl)methyl]-5-methylsulfanyl-1,2,4-triazole Chemical compound N1=C(SC)N(CC(OCC)OCC)C(CC=2C=CC(OC)=CC=2)=N1 TZVKIWHRWPDDQG-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- BWQVEPQXHCHRKE-UHFFFAOYSA-N 5,11,11-trimethyl-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2C(C)(C)C2=NN=C(SC)N21 BWQVEPQXHCHRKE-UHFFFAOYSA-N 0.000 description 1
- JOQTUTXEBSUXSR-UHFFFAOYSA-N 5,11,11-trimethyl-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2C(C)(C)C2=NN=C(S(C)=O)N12 JOQTUTXEBSUXSR-UHFFFAOYSA-N 0.000 description 1
- OQTLQHWGMKMJLC-UHFFFAOYSA-N 5,11,11-trimethyl-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2C(C)(C)C2=NN=C(S(C)(=O)=O)N12 OQTLQHWGMKMJLC-UHFFFAOYSA-N 0.000 description 1
- ASPISOOBBHWDQY-UHFFFAOYSA-N 5,11-dimethyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=C(C)N2C(SC)=NN=C2C(C)C2=CC=CC=C21 ASPISOOBBHWDQY-UHFFFAOYSA-N 0.000 description 1
- KKMDSQSYEJTQBG-UHFFFAOYSA-N 5,11-dimethyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2C(C)C2=NN=C(S(C)=O)N21 KKMDSQSYEJTQBG-UHFFFAOYSA-N 0.000 description 1
- QAQKIXXFHQMKIZ-UHFFFAOYSA-N 5,11-dimethyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2C(C)C2=NN=C(S(C)(=O)=O)N21 QAQKIXXFHQMKIZ-UHFFFAOYSA-N 0.000 description 1
- IJBRTRIZUCEIEN-UHFFFAOYSA-N 5-ethyl-3-methoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CCC1=CC2=CC=CC=C2CC2=NN=C(OC)N12 IJBRTRIZUCEIEN-UHFFFAOYSA-N 0.000 description 1
- SBBMZBJNRSCTQY-UHFFFAOYSA-N 5-ethyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CCC1=CC2=CC=CC=C2CC2=NN=C(SC)N12 SBBMZBJNRSCTQY-UHFFFAOYSA-N 0.000 description 1
- PASJNUZWMHRUJN-UHFFFAOYSA-N 5-ethyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CCC1=CC2=CC=CC=C2CC2=NN=C(S(C)=O)N12 PASJNUZWMHRUJN-UHFFFAOYSA-N 0.000 description 1
- MNWOAXBMZSKDPO-UHFFFAOYSA-N 5-ethyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CCC1=CC2=CC=CC=C2CC2=NN=C(S(C)(=O)=O)N12 MNWOAXBMZSKDPO-UHFFFAOYSA-N 0.000 description 1
- NOFMWVQJRUMSNJ-UHFFFAOYSA-N 5-methyl-3-methylsulfanyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=CC=CC=C2C=C(C)N2C(SC)=NN=C2C1C1=CC=CC=C1 NOFMWVQJRUMSNJ-UHFFFAOYSA-N 0.000 description 1
- MMKCQWLQNFGYFV-UHFFFAOYSA-N 5-methyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=C(C)N2C(SC)=NN=C2CC2=CC=CC=C21 MMKCQWLQNFGYFV-UHFFFAOYSA-N 0.000 description 1
- VLSSCQACQRBWMO-UHFFFAOYSA-N 5-methyl-3-methylsulfinyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=NN=C(S(C)=O)N2C(C)=CC2=CC=CC=C2C1C1=CC=CC=C1 VLSSCQACQRBWMO-UHFFFAOYSA-N 0.000 description 1
- BUYIRERHCFTWLC-UHFFFAOYSA-N 5-methyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2CC2=NN=C(S(C)=O)N12 BUYIRERHCFTWLC-UHFFFAOYSA-N 0.000 description 1
- RJKXRNUHYKDTOR-UHFFFAOYSA-N 5-methyl-3-methylsulfonyl-11-phenyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C12=NN=C(S(C)(=O)=O)N2C(C)=CC2=CC=CC=C2C1C1=CC=CC=C1 RJKXRNUHYKDTOR-UHFFFAOYSA-N 0.000 description 1
- LWOZBBCSPMMQBH-UHFFFAOYSA-N 5-methyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CC2=CC=CC=C2CC2=NN=C(S(C)(=O)=O)N12 LWOZBBCSPMMQBH-UHFFFAOYSA-N 0.000 description 1
- DTWBWORHUGHLET-UHFFFAOYSA-N 6-ethyl-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CCC1=CN2C(SC)=NN=C2CC2=CC=CC=C12 DTWBWORHUGHLET-UHFFFAOYSA-N 0.000 description 1
- KRQIEBRHDPQWTH-UHFFFAOYSA-N 6-methyl-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CN2C(S(C)=O)=NN=C2CC2=CC=CC=C12 KRQIEBRHDPQWTH-UHFFFAOYSA-N 0.000 description 1
- XZJGBNDMTOPMAD-UHFFFAOYSA-N 6-methyl-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound CC1=CN2C(S(C)(=O)=O)=NN=C2CC2=CC=CC=C12 XZJGBNDMTOPMAD-UHFFFAOYSA-N 0.000 description 1
- MAIVOPNJGDASAS-UHFFFAOYSA-N 8,9-dimethoxy-11-methylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=C)C2=C1C=C(OC)C(OC)=C2 MAIVOPNJGDASAS-UHFFFAOYSA-N 0.000 description 1
- FHTSYNRYKMTJRY-UHFFFAOYSA-N 8,9-dimethoxy-11-methylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=C)C2=C1C=C(OC)C(OC)=C2 FHTSYNRYKMTJRY-UHFFFAOYSA-N 0.000 description 1
- JGQHEUGGKLVTKS-UHFFFAOYSA-N 8,9-dimethoxy-11-methylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=C)C2=C1C=C(OC)C(OC)=C2 JGQHEUGGKLVTKS-UHFFFAOYSA-N 0.000 description 1
- QTWUQNUYJKQRPE-UHFFFAOYSA-N 8,9-dimethoxy-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1C2=NN=C(SC)N2C=CC2=C1C=C(OC)C(OC)=C2 QTWUQNUYJKQRPE-UHFFFAOYSA-N 0.000 description 1
- VEWJLBXBYVDZNZ-UHFFFAOYSA-N 8,9-dimethoxy-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1C2=NN=C(S(C)=O)N2C=CC2=C1C=C(OC)C(OC)=C2 VEWJLBXBYVDZNZ-UHFFFAOYSA-N 0.000 description 1
- QCBTXXQNCBGAAB-UHFFFAOYSA-N 8,9-dimethoxy-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1C2=NN=C(S(C)(=O)=O)N2C=CC2=C1C=C(OC)C(OC)=C2 QCBTXXQNCBGAAB-UHFFFAOYSA-N 0.000 description 1
- LTSFLDNMSCEMQB-UHFFFAOYSA-N 8-bromo-3-ethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical class C1=CN2C(OCC)=NN=C2CC2=CC=C(Br)C=C21 LTSFLDNMSCEMQB-UHFFFAOYSA-N 0.000 description 1
- BWIWIJPDUOXZLR-UHFFFAOYSA-N 8-bromo-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical class C1=CN2C(SC)=NN=C2CC2=CC=C(Br)C=C21 BWIWIJPDUOXZLR-UHFFFAOYSA-N 0.000 description 1
- YQVJGZFOAUNBKH-UHFFFAOYSA-N 8-bromo-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2CC2=CC=C(Br)C=C21 YQVJGZFOAUNBKH-UHFFFAOYSA-N 0.000 description 1
- HYOZVPROAZVPRV-UHFFFAOYSA-N 8-bromo-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2CC2=CC=C(Br)C=C21 HYOZVPROAZVPRV-UHFFFAOYSA-N 0.000 description 1
- BROONUYTPJWMAB-UHFFFAOYSA-N 8-chloro-11-ethylidene-3-methoxy-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=CC)C2=CC=C(Cl)C=C21 BROONUYTPJWMAB-UHFFFAOYSA-N 0.000 description 1
- ZPJXWMLXDCOTGG-UHFFFAOYSA-N 8-chloro-11-methylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=C)C2=CC=C(Cl)C=C21 ZPJXWMLXDCOTGG-UHFFFAOYSA-N 0.000 description 1
- WCCKWJNGVRJQIE-UHFFFAOYSA-N 8-chloro-11-methylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2C(=C)C2=CC=C(Cl)C=C21 WCCKWJNGVRJQIE-UHFFFAOYSA-N 0.000 description 1
- SJHOOTONJRQNFV-UHFFFAOYSA-N 8-chloro-11-methylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2C(=C)C2=CC=C(Cl)C=C21 SJHOOTONJRQNFV-UHFFFAOYSA-N 0.000 description 1
- QJTHVGDSOCKPRG-UHFFFAOYSA-N 8-chloro-2,11-dihydro-[1,2,4]triazolo[3,4-b][3]benzazepin-3-one Chemical compound C1=CC2=CC(Cl)=CC=C2CC2=NNC(=O)N21 QJTHVGDSOCKPRG-UHFFFAOYSA-N 0.000 description 1
- LWGUVZZAXFVWKY-UHFFFAOYSA-N 8-chloro-3-ethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC=C(Cl)C=C21 LWGUVZZAXFVWKY-UHFFFAOYSA-N 0.000 description 1
- DVRXBZOJSLACEL-UHFFFAOYSA-N 8-chloro-3-ethoxy-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(Cl)=CC=C2C(=O)C2=NN=C(OCC)N21 DVRXBZOJSLACEL-UHFFFAOYSA-N 0.000 description 1
- CVYXYHRODPNJMT-UHFFFAOYSA-N 8-chloro-3-methoxy-11-methylidene-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OC)=NN=C2C(=C)C2=CC=C(Cl)C=C21 CVYXYHRODPNJMT-UHFFFAOYSA-N 0.000 description 1
- HYXXYUVLTKEMMY-UHFFFAOYSA-N 8-chloro-3-methoxy-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(Cl)=CC=C2C(=O)C2=NN=C(OC)N21 HYXXYUVLTKEMMY-UHFFFAOYSA-N 0.000 description 1
- KMYMGZWXPHJROQ-UHFFFAOYSA-N 8-chloro-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(Cl)=CC=C2C(=O)C2=NN=C(S(=O)C)N21 KMYMGZWXPHJROQ-UHFFFAOYSA-N 0.000 description 1
- IGXMLOUQBYIAJR-UHFFFAOYSA-N 8-chloro-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CC2=CC(Cl)=CC=C2C(=O)C2=NN=C(S(=O)(=O)C)N21 IGXMLOUQBYIAJR-UHFFFAOYSA-N 0.000 description 1
- KOXWYSDCSHYVHF-UHFFFAOYSA-N 8-methoxy-11-methylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=C)C2=CC=C(OC)C=C21 KOXWYSDCSHYVHF-UHFFFAOYSA-N 0.000 description 1
- MXLOZZRJTBTTLP-UHFFFAOYSA-N 8-methoxy-11-methylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=C)C2=CC=C(OC)C=C21 MXLOZZRJTBTTLP-UHFFFAOYSA-N 0.000 description 1
- JTXZQOLKPNKNQN-UHFFFAOYSA-N 8-methoxy-11-methylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=C)C2=CC=C(OC)C=C21 JTXZQOLKPNKNQN-UHFFFAOYSA-N 0.000 description 1
- POQSSEBLWSUJAI-UHFFFAOYSA-N 8-methoxy-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(SC)=NN=C2C(=O)C2=CC=C(OC)C=C21 POQSSEBLWSUJAI-UHFFFAOYSA-N 0.000 description 1
- WWCUHENWDXVEBT-UHFFFAOYSA-N 8-methoxy-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=O)C2=CC=C(OC)C=C21 WWCUHENWDXVEBT-UHFFFAOYSA-N 0.000 description 1
- HSDAWRQMRSIMOD-UHFFFAOYSA-N 8-methoxy-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=O)C2=CC=C(OC)C=C21 HSDAWRQMRSIMOD-UHFFFAOYSA-N 0.000 description 1
- NXFNWOREOIBWHP-UHFFFAOYSA-N 8-methyl-11-methylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=C)C2=CC=C(C)C=C21 NXFNWOREOIBWHP-UHFFFAOYSA-N 0.000 description 1
- NCCYQRHEPUZDCF-UHFFFAOYSA-N 8-methyl-11-methylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=C)C2=CC=C(C)C=C21 NCCYQRHEPUZDCF-UHFFFAOYSA-N 0.000 description 1
- ZUEOFRJHBDOZRS-UHFFFAOYSA-N 8-methyl-11-methylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=C)C2=CC=C(C)C=C21 ZUEOFRJHBDOZRS-UHFFFAOYSA-N 0.000 description 1
- LAEODTNSJPSGBH-UHFFFAOYSA-N 8-methyl-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=O)C2=CC=C(C)C=C21 LAEODTNSJPSGBH-UHFFFAOYSA-N 0.000 description 1
- WKIYUYAAHVBJHL-UHFFFAOYSA-N 8-methyl-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=O)C2=CC=C(C)C=C21 WKIYUYAAHVBJHL-UHFFFAOYSA-N 0.000 description 1
- RFUQGXDDHKKOBN-UHFFFAOYSA-N 9-chloro-3-ethoxy-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(OCC)=NN=C2CC2=CC(Cl)=CC=C21 RFUQGXDDHKKOBN-UHFFFAOYSA-N 0.000 description 1
- JUPCPGBPCNLYBD-UHFFFAOYSA-N 9-chloro-3-methylsulfanyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2CC2=CC(Cl)=CC=C21 JUPCPGBPCNLYBD-UHFFFAOYSA-N 0.000 description 1
- XSMWEJRWDPKVAP-UHFFFAOYSA-N 9-chloro-3-methylsulfinyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)C)=NN=C2CC2=CC(Cl)=CC=C21 XSMWEJRWDPKVAP-UHFFFAOYSA-N 0.000 description 1
- HCTXNMLBWGTHNV-UHFFFAOYSA-N 9-chloro-3-methylsulfonyl-11h-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(=O)(=O)C)=NN=C2CC2=CC(Cl)=CC=C21 HCTXNMLBWGTHNV-UHFFFAOYSA-N 0.000 description 1
- JAGHAVRRBCFMOB-UHFFFAOYSA-N 9-methoxy-11-methylidene-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(SC)=NN=C2C(=C)C2=CC(OC)=CC=C21 JAGHAVRRBCFMOB-UHFFFAOYSA-N 0.000 description 1
- OSLLMTHQWKVOCC-UHFFFAOYSA-N 9-methoxy-11-methylidene-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=C)C2=CC(OC)=CC=C21 OSLLMTHQWKVOCC-UHFFFAOYSA-N 0.000 description 1
- XDSQKKPXRZWWMQ-UHFFFAOYSA-N 9-methoxy-11-methylidene-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepine Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=C)C2=CC(OC)=CC=C21 XDSQKKPXRZWWMQ-UHFFFAOYSA-N 0.000 description 1
- GLQGGHZAXASADV-UHFFFAOYSA-N 9-methoxy-3-methylsulfanyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(SC)=NN=C2C(=O)C2=CC(OC)=CC=C21 GLQGGHZAXASADV-UHFFFAOYSA-N 0.000 description 1
- WZNGJGDOOVXNIZ-UHFFFAOYSA-N 9-methoxy-3-methylsulfinyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(S(C)=O)=NN=C2C(=O)C2=CC(OC)=CC=C21 WZNGJGDOOVXNIZ-UHFFFAOYSA-N 0.000 description 1
- ANBCAHBAMMPXCX-UHFFFAOYSA-N 9-methoxy-3-methylsulfonyl-[1,2,4]triazolo[3,4-b][3]benzazepin-11-one Chemical compound C1=CN2C(S(C)(=O)=O)=NN=C2C(=O)C2=CC(OC)=CC=C21 ANBCAHBAMMPXCX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical compound Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9418376A JPS5328194A (en) | 1976-08-06 | 1976-08-06 | Heterocyclic compounds and their preparation |
| JP1749977A JPS53103496A (en) | 1977-02-18 | 1977-02-18 | Heterocyclic compounds and process for their preparation |
| JP1750077A JPS53103492A (en) | 1977-02-18 | 1977-02-18 | Heterocylic compounds and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2735158A1 true DE2735158A1 (de) | 1978-02-09 |
Family
ID=27281857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772735158 Withdrawn DE2735158A1 (de) | 1976-08-06 | 1977-08-04 | Triazolbenzazepinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4150139A (OSRAM) |
| AU (1) | AU505150B2 (OSRAM) |
| CA (1) | CA1084491A (OSRAM) |
| DE (1) | DE2735158A1 (OSRAM) |
| DK (1) | DK351377A (OSRAM) |
| FR (1) | FR2360593A1 (OSRAM) |
| GB (1) | GB1567825A (OSRAM) |
| NL (1) | NL7708725A (OSRAM) |
| SE (1) | SE7708894L (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4243589A (en) * | 1979-11-30 | 1981-01-06 | Hoffmann-La Roche Inc. | Triazolobenzazepines and processes for their production |
| US4621046A (en) * | 1983-03-18 | 1986-11-04 | Fuji Photo Film Co., Ltd. | Pyrazolo(1,5-B)-1,2,4-triazole derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2442987A1 (de) | 1973-09-14 | 1975-03-20 | Takeda Chemical Industries Ltd | Benzazepinderivate und verfahren zu deren herstellung sowie sie enthaltende pharmazeutische zusammensetzungen |
-
1977
- 1977-07-26 AU AU27325/77A patent/AU505150B2/en not_active Expired
- 1977-08-03 FR FR7723964A patent/FR2360593A1/fr active Granted
- 1977-08-03 US US05/821,623 patent/US4150139A/en not_active Expired - Lifetime
- 1977-08-04 DE DE19772735158 patent/DE2735158A1/de not_active Withdrawn
- 1977-08-04 SE SE7708894A patent/SE7708894L/xx unknown
- 1977-08-05 DK DK351377A patent/DK351377A/da unknown
- 1977-08-05 CA CA284,171A patent/CA1084491A/en not_active Expired
- 1977-08-05 GB GB32900/77A patent/GB1567825A/en not_active Expired
- 1977-08-05 NL NL7708725A patent/NL7708725A/xx not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2442987A1 (de) | 1973-09-14 | 1975-03-20 | Takeda Chemical Industries Ltd | Benzazepinderivate und verfahren zu deren herstellung sowie sie enthaltende pharmazeutische zusammensetzungen |
Also Published As
| Publication number | Publication date |
|---|---|
| DK351377A (da) | 1978-02-07 |
| SE7708894L (sv) | 1978-02-07 |
| GB1567825A (en) | 1980-05-21 |
| NL7708725A (nl) | 1978-02-08 |
| CA1084491A (en) | 1980-08-26 |
| US4150139A (en) | 1979-04-17 |
| AU505150B2 (en) | 1979-11-08 |
| AU2732577A (en) | 1979-02-01 |
| FR2360593A1 (fr) | 1978-03-03 |
| FR2360593B1 (OSRAM) | 1981-06-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1967325C2 (de) | Isomere 3,4-Dihydro-2H-1,2-benzothiazin-1,1-dioxide | |
| US4140789A (en) | Etherified hydroxy-benzodiheterocyclic compounds | |
| DE3784401T2 (de) | Karbostyril-derivate und ihre salze, verfahren zu ihrer herstellung und diese enthaltende kardiotonische zusammensetzung. | |
| DE2037693A1 (de) | Chinazolinderivate,verfahren zu ihrer herstellung und ihre verwendung | |
| EP0612731B1 (de) | Neue Chinolon- und Naphthyridoncarbonsäurederivate | |
| CH641757A5 (en) | O-Alkylated hydroxylamines and process for the preparation thereof | |
| DE2138031C3 (de) | Verfahren zur Herstellung von 1.2.4-Triazin-5-onen | |
| DE2828293A1 (de) | N-dichloracetyl-1,2,3,4-tetrahydro- chinaldin, verfahren zu dessen herstellung und dessen verwendung zur verhuetung von herbizidschaeden an kulturpflanzen | |
| DE3739882A1 (de) | Substituierte hydroxylamine | |
| EP0323799B1 (de) | Imidazolderivate II | |
| DE2658806A1 (de) | Cyclische derivate von 1,4-benzoxazin und 1,4-benzothiazin, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel | |
| DE3209304C2 (OSRAM) | ||
| DE2735158A1 (de) | Triazolbenzazepinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen | |
| EP0298921B1 (de) | 1,2-Benzisoxazole und 1,2-Benzisothiazole | |
| US3992397A (en) | (1-Alkyl-5-nitro-imidazolyl-2-alkyl)-heteroaryl compounds and process for their manufacture | |
| DE1695189A1 (de) | Verfahren zur Herstellung von Imidazolderivaten | |
| DE2509843A1 (de) | Verfahren zur herstellung von s-triazolo eckige klammer auf 3,4-b eckige klammer zu benzothiazolen | |
| EP0006542A2 (de) | Verwendung des N-Dichloracetyl-1,2,3,4-tetrahydroisochinolins als Gegenmittel zum Schutz von Kulturpflanzen vor Schädigungen durch herbizid-wirksame Acetanilide; die so erhaltenen Kombinationen und Verfahren zu deren Herstellung | |
| CH637654A5 (en) | Triazolobenzazepine derivatives, process for their preparation and pharmaceutical preparations containing them | |
| EP0108908B1 (de) | Neue Benzotriazole, ihre Herstellung und ihre Verwendung als biozide Wirkstoffe | |
| DE3839170A1 (de) | Cyclopropyl-substituierte azolylmethylcarbinole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE2233682A1 (de) | 2- eckige klammer auf 3-(subst. aminomethyl)-4-h-1,2,4-triazol-4-yl eckige klammer zu -benzophenone, ein verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel | |
| DE2921001A1 (de) | Tetrahydrothiopyrano eckige klammer auf 2,3-b eckige klammer zu indolderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel | |
| EP0006541A2 (de) | Verwendung von N,N-Diallyl-dichloracetamid zur Verbesserung der Kulturpflanzen-Verträglichkeit von herbizid wirksamen Acetaniliden | |
| EP0075167B1 (de) | N-(1-Alkenyl)-carbonsäureanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |