CS248711B2 - Production method of the/l1,2,4/triazol/4,3-a/chinoxaline-4-amin derivatives - Google Patents
Production method of the/l1,2,4/triazol/4,3-a/chinoxaline-4-amin derivatives Download PDFInfo
- Publication number
- CS248711B2 CS248711B2 CS837528A CS752883A CS248711B2 CS 248711 B2 CS248711 B2 CS 248711B2 CS 837528 A CS837528 A CS 837528A CS 752883 A CS752883 A CS 752883A CS 248711 B2 CS248711 B2 CS 248711B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- triazolo
- quinoxaline
- chloro
- ethyl
- mol
- Prior art date
Links
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims description 77
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000460 chlorine Substances 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 22
- 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 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- JQHGLMJLABTXOL-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical class NC1=NC2=CC=CC=C2N2C1=NN=C2 JQHGLMJLABTXOL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 4
- 230000010933 acylation Effects 0.000 claims 3
- 238000005917 acylation reaction Methods 0.000 claims 3
- 150000008282 halocarbons Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 104
- 239000000203 mixture Substances 0.000 description 89
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
- 239000000047 product Substances 0.000 description 68
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- 238000001819 mass spectrum Methods 0.000 description 60
- 239000000243 solution Substances 0.000 description 55
- 239000002244 precipitate Substances 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 229910052757 nitrogen Inorganic materials 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 47
- 229910052799 carbon Inorganic materials 0.000 description 38
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 27
- 238000001953 recrystallisation Methods 0.000 description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 239000005457 ice water Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 16
- 238000005406 washing Methods 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 239000002274 desiccant Substances 0.000 description 15
- 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 14
- 241000700159 Rattus Species 0.000 description 14
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- -1 alkyl orthobenzoate Chemical compound 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- RODNZCIFRICALV-UHFFFAOYSA-N (3-chloroquinoxalin-2-yl)hydrazine Chemical compound C1=CC=C2N=C(Cl)C(NN)=NC2=C1 RODNZCIFRICALV-UHFFFAOYSA-N 0.000 description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000935 antidepressant agent Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- LFJRTFZMVFGBTB-UHFFFAOYSA-N 4-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=CC=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 LFJRTFZMVFGBTB-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 7
- 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
- 229940005513 antidepressants Drugs 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 6
- 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
- QNSRYVDGWDXBHV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxaline Chemical class C1=CC=C2N3C=NN=C3C=NC2=C1 QNSRYVDGWDXBHV-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 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 4
- 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 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002929 anti-fatigue Effects 0.000 description 4
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- KTRZFDUOUIVFLG-UHFFFAOYSA-N n,n-diethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=CC=C2N2C1=NN=C2 KTRZFDUOUIVFLG-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 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 3
- 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 3
- BSCJWJHKQIANRW-UHFFFAOYSA-N (6-fluoro-3-methoxyquinoxalin-2-yl)hydrazine Chemical compound FC1=CC=C2N=C(NN)C(OC)=NC2=C1 BSCJWJHKQIANRW-UHFFFAOYSA-N 0.000 description 3
- FWPZNTLMWXLYMI-UHFFFAOYSA-N 1-ethyl-7-methoxy-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound COC1=CC=C2N3C(CC)=NN=C3C(O)=NC2=C1 FWPZNTLMWXLYMI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 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
- PIOTUXYREAUWOA-UHFFFAOYSA-N 4-chloro-1-ethyl-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound FC1=CC=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 PIOTUXYREAUWOA-UHFFFAOYSA-N 0.000 description 3
- KJXIBZROUGENCF-UHFFFAOYSA-N 4-chloro-1-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=CC=C2N3C(C)=NN=C3C(Cl)=NC2=C1 KJXIBZROUGENCF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- KUIYXECVXAZBJL-UHFFFAOYSA-N 4-chloro-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(Cl)C2=NN=CN2C2=CC=C(F)C=C21 KUIYXECVXAZBJL-UHFFFAOYSA-N 0.000 description 3
- NARSIYNOVDKTQP-UHFFFAOYSA-N 4-chloro-7-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(Cl)C2=NN=CN2C2=CC=C(OC)C=C21 NARSIYNOVDKTQP-UHFFFAOYSA-N 0.000 description 3
- GOGPADJQISFPEG-UHFFFAOYSA-N 4-chloro-8-fluoro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(Cl)C2=NN=CN2C2=CC(F)=CC=C21 GOGPADJQISFPEG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HTMREOADNCVDJP-UHFFFAOYSA-N 6-fluoro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=CC(F)=CC=C21 HTMREOADNCVDJP-UHFFFAOYSA-N 0.000 description 3
- RYNIDJASIHSZHT-UHFFFAOYSA-N 7-fluoro-4-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=NC2=CC(F)=CC=C2N2C1=NN=C2 RYNIDJASIHSZHT-UHFFFAOYSA-N 0.000 description 3
- JZJJSZWHKWLMQF-UHFFFAOYSA-N 7-fluoro-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound OC1=NC2=CC(F)=CC=C2N2C1=NN=C2 JZJJSZWHKWLMQF-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
- 241000124008 Mammalia Species 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- QXQPFRTUGIOURR-UHFFFAOYSA-N (3-chloro-7-fluoroquinoxalin-2-yl)hydrazine Chemical compound FC1=CC=C2N=C(Cl)C(NN)=NC2=C1 QXQPFRTUGIOURR-UHFFFAOYSA-N 0.000 description 2
- MLOQHGOUXKABKH-UHFFFAOYSA-N (3-chloro-7-methoxyquinoxalin-2-yl)hydrazine Chemical compound N1=C(Cl)C(NN)=NC2=CC(OC)=CC=C21 MLOQHGOUXKABKH-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
- QJZCMVZDNFLZQE-UHFFFAOYSA-N 1-ethyl-4,7-dimethoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=C2N3C(CC)=NN=C3C(OC)=NC2=C1 QJZCMVZDNFLZQE-UHFFFAOYSA-N 0.000 description 2
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- HDGSSYSOPRHGDY-UHFFFAOYSA-N 8-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.NC1=NC2=CC=C(F)C=C2N2C1=NN=C2 HDGSSYSOPRHGDY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
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- 239000007937 lozenge Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GDFOCQDPSBIWSQ-UHFFFAOYSA-N methanesulfonic acid;7-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CS(O)(=O)=O.N1=C(N)C2=NN=CN2C2=CC=C(OC)C=C21 GDFOCQDPSBIWSQ-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GIKMCVOCNYIDII-UHFFFAOYSA-N n,n,1-triethyl-7,8-difluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC(F)=C(F)C=C2N2C1=NN=C2CC GIKMCVOCNYIDII-UHFFFAOYSA-N 0.000 description 1
- CCYLTMPHQCIOMN-UHFFFAOYSA-N n,n,1-triethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=CC=C2N2C1=NN=C2CC CCYLTMPHQCIOMN-UHFFFAOYSA-N 0.000 description 1
- SBHKDVWPQTVNJD-UHFFFAOYSA-N n,n-diethyl-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound N=1N=C2C(N(CC)CC)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1 SBHKDVWPQTVNJD-UHFFFAOYSA-N 0.000 description 1
- BPNFZXJZPZUXCU-UHFFFAOYSA-N n,n-diethyl-1-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=CC=C2N2C1=NN=C2C(C)C BPNFZXJZPZUXCU-UHFFFAOYSA-N 0.000 description 1
- RYAWKUBOYVCMCS-UHFFFAOYSA-N n,n-diethyl-8-fluoro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=C(F)C=C2N2C1=NN=C2C(F)(F)F RYAWKUBOYVCMCS-UHFFFAOYSA-N 0.000 description 1
- QSBXMSXWWDRENW-UHFFFAOYSA-N n,n-dipropyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCCN(CCC)C1=NC2=CC=CC=C2N2C1=NN=C2 QSBXMSXWWDRENW-UHFFFAOYSA-N 0.000 description 1
- HMZAZJHJTFZUHF-UHFFFAOYSA-N n-(1-ethyl-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound FC1=CC=C2N3C(CC)=NN=C3C(NC(C)=O)=NC2=C1 HMZAZJHJTFZUHF-UHFFFAOYSA-N 0.000 description 1
- SLFQMKXTMDIQBE-UHFFFAOYSA-N n-(1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound C1=CC=C2N3C(CC)=NN=C3C(NC(C)=O)=NC2=C1 SLFQMKXTMDIQBE-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
- FSGHWNVKFOQNJR-UHFFFAOYSA-N n-(8-chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)propanamide Chemical compound CCC(=O)NC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2CC FSGHWNVKFOQNJR-UHFFFAOYSA-N 0.000 description 1
- FICFEYANQBAWLA-UHFFFAOYSA-N n-(8-chloro-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-3-methylbutanamide Chemical compound CC(C)CC(=O)NC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2 FICFEYANQBAWLA-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
- 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
- LCOFECDNEBCJEP-UHFFFAOYSA-N n-ethyl-1-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC=CC=C2N2C1=NN=C2C(C)C LCOFECDNEBCJEP-UHFFFAOYSA-N 0.000 description 1
- HCROGYHWYATUKI-UHFFFAOYSA-N n-ethyl-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCNC1=NC2=CC(F)=CC=C2N2C1=NN=C2 HCROGYHWYATUKI-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 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
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000009182 swimming Effects 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000003867 tiredness Effects 0.000 description 1
- 208000016255 tiredness Diseases 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43477182A | 1982-10-18 | 1982-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS248711B2 true CS248711B2 (en) | 1987-02-12 |
Family
ID=23725622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS837528A CS248711B2 (en) | 1982-10-18 | 1983-10-13 | Production method of the/l1,2,4/triazol/4,3-a/chinoxaline-4-amin derivatives |
Country Status (17)
Families Citing this family (5)
| 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 |
| KR101555384B1 (ko) * | 2006-12-13 | 2015-09-23 | 아스카 세이야쿠 가부시키가이샤 | 퀴녹살린 유도체 |
| US20100120741A1 (en) * | 2008-09-10 | 2010-05-13 | Kalypsys, Inc. | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| CA2810708A1 (en) * | 2010-09-16 | 2012-03-22 | Hutchison Medipharma Limited | Fused heteroaryls and their uses |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008322A (en) * | 1975-06-10 | 1977-02-15 | Eli Lilly And Company | Triazolo(4,3-a)quinoxalines for control of rice |
-
1983
- 1983-09-21 IN IN653/DEL/83A patent/IN160956B/en unknown
- 1983-10-13 GR GR72683A patent/GR78952B/el unknown
- 1983-10-13 CS CS837528A patent/CS248711B2/cs 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 FI FI833781A patent/FI74011C/fi not_active IP Right Cessation
- 1983-10-17 SU SU833653375A patent/SU1246895A3/ru active
- 1983-10-17 DD DD83255716A patent/DD215545A5/de not_active IP Right Cessation
- 1983-10-17 ES ES526533A patent/ES8504197A1/es not_active Expired
- 1983-10-17 ZA ZA837691A patent/ZA837691B/xx unknown
- 1983-10-17 NO NO833770A patent/NO160142C/no unknown
- 1983-10-17 PH PH29702A patent/PH19080A/en unknown
- 1983-10-17 NZ NZ205986A patent/NZ205986A/en unknown
- 1983-10-18 JP JP58195126A patent/JPS5989684A/ja active Granted
- 1983-10-18 KR KR1019830004929A patent/KR860001493B1/ko not_active Expired
- 1983-10-18 PL PL1983244194A patent/PL141382B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL141382B1 (en) | 1987-07-31 |
| KR840006485A (ko) | 1984-11-30 |
| CA1207772A (en) | 1986-07-15 |
| NO160142B (no) | 1988-12-05 |
| PH19080A (en) | 1985-12-19 |
| ES526533A0 (es) | 1985-04-01 |
| YU43331B (en) | 1989-06-30 |
| SU1246895A3 (ru) | 1986-07-23 |
| FI74011C (fi) | 1987-12-10 |
| DD215545A5 (de) | 1984-11-14 |
| NZ205986A (en) | 1986-06-11 |
| JPH039915B2 (enrdf_load_stackoverflow) | 1991-02-12 |
| KR860001493B1 (ko) | 1986-09-27 |
| PL244194A1 (en) | 1985-03-26 |
| JPS5989684A (ja) | 1984-05-23 |
| PT77507A (en) | 1983-11-01 |
| YU207483A (en) | 1986-02-28 |
| FI833781A0 (fi) | 1983-10-17 |
| GR78952B (enrdf_load_stackoverflow) | 1984-10-02 |
| NO160142C (no) | 1989-03-15 |
| ES8504197A1 (es) | 1985-04-01 |
| FI74011B (fi) | 1987-08-31 |
| IN160956B (enrdf_load_stackoverflow) | 1987-08-22 |
| NO833770L (no) | 1984-04-24 |
| PT77507B (en) | 1986-05-28 |
| ZA837691B (en) | 1985-05-29 |
| FI833781L (fi) | 1984-04-19 |
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