JPH039915B2 - - Google Patents
Info
- Publication number
- JPH039915B2 JPH039915B2 JP58195126A JP19512683A JPH039915B2 JP H039915 B2 JPH039915 B2 JP H039915B2 JP 58195126 A JP58195126 A JP 58195126A JP 19512683 A JP19512683 A JP 19512683A JP H039915 B2 JPH039915 B2 JP H039915B2
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- quinoxaline
- chloro
- ethyl
- mol
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- -1 piperazino Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- JQHGLMJLABTXOL-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound NC1=NC2=CC=CC=C2N2C1=NN=C2 JQHGLMJLABTXOL-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 89
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
- 238000004519 manufacturing process Methods 0.000 description 68
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 62
- 239000000047 product Substances 0.000 description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 238000001819 mass spectrum Methods 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000002244 precipitate Substances 0.000 description 50
- 238000003756 stirring Methods 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- PDOPFYRTIVSUKL-UHFFFAOYSA-N 4-(azepan-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1CCCCCN1C1=NC2=CC=CC=C2N2C1=NN=C2 PDOPFYRTIVSUKL-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- 238000000921 elemental analysis Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 229910001873 dinitrogen Inorganic materials 0.000 description 20
- 239000005457 ice water Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000000354 decomposition reaction Methods 0.000 description 15
- 239000002274 desiccant Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000002002 slurry Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- DYAHQFWOVKZOOW-UHFFFAOYSA-N Sarin Chemical class CC(C)OP(C)(F)=O DYAHQFWOVKZOOW-UHFFFAOYSA-N 0.000 description 11
- QNSRYVDGWDXBHV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=CC=C2N3C=NN=C3C=NC2=C1 QNSRYVDGWDXBHV-UHFFFAOYSA-N 0.000 description 11
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 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 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 7
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
- UMIBNTAMBAHQPV-UHFFFAOYSA-N (3,7-dichloroquinoxalin-2-yl)hydrazine Chemical compound ClC1=CC=C2N=C(Cl)C(NN)=NC2=C1 UMIBNTAMBAHQPV-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000007605 air drying Methods 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- 230000002929 anti-fatigue Effects 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- GULVDPYLWVXKGC-UHFFFAOYSA-N quinoxalin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=CN=C21 GULVDPYLWVXKGC-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RBMLIYRGDQDESW-UHFFFAOYSA-N (3,6-dimethoxyquinoxalin-2-yl)hydrazine Chemical compound N1=C(NN)C(OC)=NC2=CC(OC)=CC=C21 RBMLIYRGDQDESW-UHFFFAOYSA-N 0.000 description 3
- OCIBVLGWPDAOAZ-UHFFFAOYSA-N 1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound C1=CC=C2N3C(CC)=NN=C3C(N)=NC2=C1 OCIBVLGWPDAOAZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OXIFSRBTDOYQIK-UHFFFAOYSA-N 2h-quinoxalin-1-amine Chemical class C1=CC=C2N(N)CC=NC2=C1 OXIFSRBTDOYQIK-UHFFFAOYSA-N 0.000 description 3
- AYXRADUSDDFHBN-UHFFFAOYSA-N 4,8-dichloro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C(Cl)C=C2N3C(C(F)(F)F)=NN=C3C(Cl)=NC2=C1 AYXRADUSDDFHBN-UHFFFAOYSA-N 0.000 description 3
- PMNAZOMHAPSTJO-UHFFFAOYSA-N 4-chloro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=CC=C2N3C(C(F)(F)F)=NN=C3C(Cl)=NC2=C1 PMNAZOMHAPSTJO-UHFFFAOYSA-N 0.000 description 3
- NLAAGSHTVZHFTR-UHFFFAOYSA-N 4-chloro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound ClC1=NC2=CC=CC=C2N2C1=NN=C2 NLAAGSHTVZHFTR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- ZHJDHVKDTHCGPR-UHFFFAOYSA-N n,n-diethyl-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=CC=C2N2C1=NN=C2C(F)(F)F ZHJDHVKDTHCGPR-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- QJLVLKDXBTZABD-UHFFFAOYSA-N (3,6,7-trichloroquinoxalin-2-yl)hydrazine Chemical compound ClC1=C(Cl)C=C2N=C(Cl)C(NN)=NC2=C1 QJLVLKDXBTZABD-UHFFFAOYSA-N 0.000 description 2
- XLQWUSFUQFVYQP-UHFFFAOYSA-N (3-chloro-6,7-difluoroquinoxalin-2-yl)hydrazine Chemical compound FC1=C(F)C=C2N=C(Cl)C(NN)=NC2=C1 XLQWUSFUQFVYQP-UHFFFAOYSA-N 0.000 description 2
- FQJMHCIJFGVJAA-UHFFFAOYSA-N 1,1,1-triethoxy-2-methylpropane Chemical compound CCOC(OCC)(OCC)C(C)C FQJMHCIJFGVJAA-UHFFFAOYSA-N 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KPGXUNLNBAAWFY-UHFFFAOYSA-N 1-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound C1=CC=C2NC(=O)C3=NN=C(C(F)(F)F)N3C2=C1 KPGXUNLNBAAWFY-UHFFFAOYSA-N 0.000 description 2
- GZEGFNCRZUGIOB-UHFFFAOYSA-N 2,3,6-trichloroquinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(Cl)=CC=C21 GZEGFNCRZUGIOB-UHFFFAOYSA-N 0.000 description 2
- CMQLMJCICYOHDE-UHFFFAOYSA-N 2,3-dichloro-6,7-difluoroquinoxaline Chemical compound ClC1=C(Cl)N=C2C=C(F)C(F)=CC2=N1 CMQLMJCICYOHDE-UHFFFAOYSA-N 0.000 description 2
- VVVJWGDOTVMBNA-UHFFFAOYSA-N 2,3-dichloro-6-fluoroquinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(F)=CC=C21 VVVJWGDOTVMBNA-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
- SMYNGJONKCPXLP-UHFFFAOYSA-N 4,7-dichloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound ClC1=CC=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 SMYNGJONKCPXLP-UHFFFAOYSA-N 0.000 description 2
- VESVPUZXKHKXCJ-UHFFFAOYSA-N 4,8-dichloro-1-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C(Cl)C=C2N3C(C)=NN=C3C(Cl)=NC2=C1 VESVPUZXKHKXCJ-UHFFFAOYSA-N 0.000 description 2
- CLFGEIPOLXYYSE-UHFFFAOYSA-N 4-chloro-1-ethyl-6,7-difluoro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound FC1=CC=C2N3C(CC)=NN=C3C(Cl)=NC2=C1F CLFGEIPOLXYYSE-UHFFFAOYSA-N 0.000 description 2
- WDDWDHLLDLGVEC-UHFFFAOYSA-N 4-chloro-1-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=CC=C2N3C(C(C)C)=NN=C3C(Cl)=NC2=C1 WDDWDHLLDLGVEC-UHFFFAOYSA-N 0.000 description 2
- KMFGPKLOIQOHIJ-UHFFFAOYSA-N 4-chloro-7,8-difluoro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(Cl)C2=NN=CN2C2=C1C=C(F)C(F)=C2 KMFGPKLOIQOHIJ-UHFFFAOYSA-N 0.000 description 2
- KFUMSIBOUBHLIJ-UHFFFAOYSA-N 6,7-difluoro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C(F)C(F)=C2 KFUMSIBOUBHLIJ-UHFFFAOYSA-N 0.000 description 2
- ATHBTKQTEBOPJM-UHFFFAOYSA-N 7-chloro-1-ethyl-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound ClC1=CC=C2N3C(CC)=NN=C3C(O)=NC2=C1 ATHBTKQTEBOPJM-UHFFFAOYSA-N 0.000 description 2
- FMTFOUJZYXMZBR-UHFFFAOYSA-N 8-chloro-1-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound OC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2C(F)(F)F FMTFOUJZYXMZBR-UHFFFAOYSA-N 0.000 description 2
- ARSLYVWGUXVWSB-UHFFFAOYSA-N 8-chloro-n,n,1-triethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=C(Cl)C=C2N2C1=NN=C2CC ARSLYVWGUXVWSB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000277269 Oncorhynchus masou Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052776 Thorium Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
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- MVBLAVHZYWVUAZ-UHFFFAOYSA-N n-(7,8-dichloro-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-3-methylbutanamide Chemical compound CC(C)CC(=O)NC1=NC2=CC(Cl)=C(Cl)C=C2N2C1=NN=C2 MVBLAVHZYWVUAZ-UHFFFAOYSA-N 0.000 description 1
- HWXCHJLCJWXJNR-UHFFFAOYSA-N n-(7-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound ClC1=CC=C2N3C(CC)=NN=C3C(NC(C)=O)=NC2=C1 HWXCHJLCJWXJNR-UHFFFAOYSA-N 0.000 description 1
- XJWNFVBLLNYYOS-UHFFFAOYSA-N n-(7-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound CC(=O)NC1=NC2=CC(F)=CC=C2N2C1=NN=C2 XJWNFVBLLNYYOS-UHFFFAOYSA-N 0.000 description 1
- RBSIHXDBNRTXHC-UHFFFAOYSA-N n-(8-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-2,2-dimethylpropanamide Chemical compound C1=C(Cl)C=C2N3C(CC)=NN=C3C(NC(=O)C(C)(C)C)=NC2=C1 RBSIHXDBNRTXHC-UHFFFAOYSA-N 0.000 description 1
- NPQVPYJZBQUEFE-UHFFFAOYSA-N n-(8-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-3-methylbutanamide Chemical compound C1=C(Cl)C=C2N3C(CC)=NN=C3C(NC(=O)CC(C)C)=NC2=C1 NPQVPYJZBQUEFE-UHFFFAOYSA-N 0.000 description 1
- IUMQLSKNEMATAI-UHFFFAOYSA-N n-(8-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound C1=C(Cl)C=C2N3C(CC)=NN=C3C(NC(C)=O)=NC2=C1 IUMQLSKNEMATAI-UHFFFAOYSA-N 0.000 description 1
- PAPBNDDSCARHKA-UHFFFAOYSA-N n-(8-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound CC(=O)NC1=NC2=CC=C(F)C=C2N2C1=NN=C2 PAPBNDDSCARHKA-UHFFFAOYSA-N 0.000 description 1
- BFUPXJQVBNCMKU-UHFFFAOYSA-N n-([1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound CC(=O)NC1=NC2=CC=CC=C2N2C1=NN=C2 BFUPXJQVBNCMKU-UHFFFAOYSA-N 0.000 description 1
- KVBPPOHPVSAROZ-UHFFFAOYSA-N n-[8-fluoro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl]acetamide Chemical compound CC(=O)NC1=NC2=CC=C(F)C=C2N2C1=NN=C2C(F)(F)F KVBPPOHPVSAROZ-UHFFFAOYSA-N 0.000 description 1
- OKUWPQGMPZHRPE-UHFFFAOYSA-N n-acetyl-n-(1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound C1=CC=C2N3C(CC)=NN=C3C(N(C(C)=O)C(C)=O)=NC2=C1 OKUWPQGMPZHRPE-UHFFFAOYSA-N 0.000 description 1
- ZEFJRDDTEDKDEF-UHFFFAOYSA-N n-acetyl-n-(8-chloro-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound CC(=O)N(C(C)=O)C1=NC2=CC=C(Cl)C=C2N2C1=NN=C2 ZEFJRDDTEDKDEF-UHFFFAOYSA-N 0.000 description 1
- RMZSPVYHYHHOEK-UHFFFAOYSA-N n-acetyl-n-([1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound CC(=O)N(C(C)=O)C1=NC2=CC=CC=C2N2C1=NN=C2 RMZSPVYHYHHOEK-UHFFFAOYSA-N 0.000 description 1
- PJIFJXDDWQAHHI-UHFFFAOYSA-N n-ethyl-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC=CC=C2N2C1=NN=C2C(F)(F)F PJIFJXDDWQAHHI-UHFFFAOYSA-N 0.000 description 1
- PAVUHVZVXZTBMF-UHFFFAOYSA-N n-ethyl-7,8-difluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC(F)=C(F)C=C2N2C1=NN=C2 PAVUHVZVXZTBMF-UHFFFAOYSA-N 0.000 description 1
- JTEYUGLETIGCPG-UHFFFAOYSA-N n-ethyl-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-1-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.FC1=CC=C2N3C(NCC)=NN=C3C=NC2=C1 JTEYUGLETIGCPG-UHFFFAOYSA-N 0.000 description 1
- JVJVGCABFXRDGV-UHFFFAOYSA-N n-ethyl-8-fluoro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCNC1=NC2=CC=C(F)C=C2N2C1=NN=C2C(F)(F)F JVJVGCABFXRDGV-UHFFFAOYSA-N 0.000 description 1
- NMEPWMIPMVMUJJ-UHFFFAOYSA-N n-ethyl-8-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC=C(F)C=C2N2C1=NN=C2 NMEPWMIPMVMUJJ-UHFFFAOYSA-N 0.000 description 1
- WSZKZAMHPZUCTA-UHFFFAOYSA-N n-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC=CC=C2N2C1=NN=C2 WSZKZAMHPZUCTA-UHFFFAOYSA-N 0.000 description 1
- NNPIEVCZQHMEDQ-UHFFFAOYSA-N n-propan-2-yl-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CC(C)NC1=NC2=CC=CC=C2N2C1=NN=C2C(F)(F)F NNPIEVCZQHMEDQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- SXBRULKJHUOQCD-UHFFFAOYSA-N propanoic acid Chemical compound CCC(O)=O.CCC(O)=O SXBRULKJHUOQCD-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000008096 xylene Substances 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43477182A | 1982-10-18 | 1982-10-18 | |
| US434789 | 1982-10-18 | ||
| US434771 | 1982-10-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5989684A JPS5989684A (ja) | 1984-05-23 |
| JPH039915B2 true JPH039915B2 (zh) | 1991-02-12 |
Family
ID=23725622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58195126A Granted JPS5989684A (ja) | 1982-10-18 | 1983-10-18 | 〔１，２，４〕トリアゾロ〔４，３―ａ〕キノキサリン―４―アミン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5989684A (zh) |
| KR (1) | KR860001493B1 (zh) |
| CA (1) | CA1207772A (zh) |
| CS (1) | CS248711B2 (zh) |
| DD (1) | DD215545A5 (zh) |
| ES (1) | ES526533A0 (zh) |
| FI (1) | FI74011C (zh) |
| GR (1) | GR78952B (zh) |
| IN (1) | IN160956B (zh) |
| NO (1) | NO160142C (zh) |
| NZ (1) | NZ205986A (zh) |
| PH (1) | PH19080A (zh) |
| PL (1) | PL141382B1 (zh) |
| PT (1) | PT77507B (zh) |
| SU (1) | SU1246895A3 (zh) |
| YU (1) | YU43331B (zh) |
| ZA (1) | ZA837691B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012502067A (ja) * | 2008-09-10 | 2012-01-26 | カリプシス・インコーポレーテッド | 疾患の治療のためのヒスタミン受容体の複素環阻害剤 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4707261B2 (ja) * | 2001-05-15 | 2011-06-22 | 日本エンバイロケミカルズ株式会社 | キノキサリン系化合物および工業用殺菌組成物 |
| JP4529535B2 (ja) * | 2004-04-30 | 2010-08-25 | 住友化学株式会社 | ４−アミノ［１，２，４］トリアゾロ［４，３−ａ］キノキサリン化合物の殺菌用途 |
| EP2103613B1 (en) * | 2006-12-13 | 2016-02-17 | ASKA Pharmaceutical Co., Ltd. | Quinoxaline derivative |
| KR20130087020A (ko) * | 2010-09-16 | 2013-08-05 | 허치슨 메디파르마 리미티드 | 축합 헤테로아릴 및 그 용도 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51151327A (en) * | 1975-06-10 | 1976-12-25 | Lilly Co Eli | Agricultural and horticultural antibacterial agent containing triasoroquinoxarine as effective ingredient |
-
1983
- 1983-09-21 IN IN653/DEL/83A patent/IN160956B/en unknown
- 1983-10-13 CS CS837528A patent/CS248711B2/cs unknown
- 1983-10-13 GR GR72683A patent/GR78952B/el unknown
- 1983-10-14 CA CA000439039A patent/CA1207772A/en not_active Expired
- 1983-10-14 YU YU2074/83A patent/YU43331B/xx unknown
- 1983-10-14 PT PT77507A patent/PT77507B/pt not_active IP Right Cessation
- 1983-10-17 NO NO833770A patent/NO160142C/no unknown
- 1983-10-17 NZ NZ205986A patent/NZ205986A/en unknown
- 1983-10-17 DD DD83255716A patent/DD215545A5/de not_active IP Right Cessation
- 1983-10-17 SU SU833653375A patent/SU1246895A3/ru active
- 1983-10-17 FI FI833781A patent/FI74011C/fi not_active IP Right Cessation
- 1983-10-17 ES ES526533A patent/ES526533A0/es active Granted
- 1983-10-17 PH PH29702A patent/PH19080A/en unknown
- 1983-10-17 ZA ZA837691A patent/ZA837691B/xx unknown
- 1983-10-18 KR KR1019830004929A patent/KR860001493B1/ko not_active IP Right Cessation
- 1983-10-18 PL PL1983244194A patent/PL141382B1/pl unknown
- 1983-10-18 JP JP58195126A patent/JPS5989684A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51151327A (en) * | 1975-06-10 | 1976-12-25 | Lilly Co Eli | Agricultural and horticultural antibacterial agent containing triasoroquinoxarine as effective ingredient |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012502067A (ja) * | 2008-09-10 | 2012-01-26 | カリプシス・インコーポレーテッド | 疾患の治療のためのヒスタミン受容体の複素環阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| YU43331B (en) | 1989-06-30 |
| FI833781A0 (fi) | 1983-10-17 |
| KR860001493B1 (ko) | 1986-09-27 |
| FI833781A (fi) | 1984-04-19 |
| DD215545A5 (de) | 1984-11-14 |
| ES8504197A1 (es) | 1985-04-01 |
| GR78952B (zh) | 1984-10-02 |
| PL244194A1 (en) | 1985-03-26 |
| FI74011B (fi) | 1987-08-31 |
| JPS5989684A (ja) | 1984-05-23 |
| NO833770L (no) | 1984-04-24 |
| ES526533A0 (es) | 1985-04-01 |
| ZA837691B (en) | 1985-05-29 |
| YU207483A (en) | 1986-02-28 |
| FI74011C (fi) | 1987-12-10 |
| NZ205986A (en) | 1986-06-11 |
| PL141382B1 (en) | 1987-07-31 |
| PT77507B (en) | 1986-05-28 |
| IN160956B (zh) | 1987-08-22 |
| PT77507A (en) | 1983-11-01 |
| PH19080A (en) | 1985-12-19 |
| CA1207772A (en) | 1986-07-15 |
| NO160142B (no) | 1988-12-05 |
| CS248711B2 (en) | 1987-02-12 |
| SU1246895A3 (ru) | 1986-07-23 |
| NO160142C (no) | 1989-03-15 |
| KR840006485A (ko) | 1984-11-30 |
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