CA1207772A - Derives amines de la triazoloquinoxaline - Google Patents

Derives amines de la triazoloquinoxaline

Info

Publication number: CA1207772A
Authority: CA; Canada
Prior art keywords: triazolo; quinoxaline; chloro; ethyl; fluoro
Prior art date: 1982-10-18
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

Application number

CA000439039A

Other languages

English (en)

Inventor

Saul B. Kadin

Reinhard Sarges

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Ltd Great Britain

Original Assignee

Pfizer Ltd Great Britain

Priority date (The priority date 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 date listed.)

1982-10-18

Filing date

1983-10-14

Publication date

1986-07-15

1983-10-14 Application filed by Pfizer Ltd Great Britain filed Critical Pfizer Ltd Great Britain

1986-07-15 Application granted granted Critical

1986-07-15 Publication of CA1207772A publication Critical patent/CA1207772A/fr

Status Expired legal-status Critical Current

Links

-1 Triazoloquinoxaline amine Chemical class 0.000 title claims abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 50
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
239000000460 chlorine Chemical group 0.000 claims abstract description 11
125000001589 carboacyl group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
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 abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
239000011737 fluorine Substances 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 73
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
238000000034 method Methods 0.000 claims description 25
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 17
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 10
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 claims description 7
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 claims description 6
150000008065 acid anhydrides Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
CHGBCRZJIYWPIX-UHFFFAOYSA-N n,1-diethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC=CC=C2N2C1=NN=C2CC CHGBCRZJIYWPIX-UHFFFAOYSA-N 0.000 claims description 4
GCAZKZDIOGTMKL-UHFFFAOYSA-N 8-fluoro-n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CC(C)NC1=NC2=CC=C(F)C=C2N2C1=NN=C2 GCAZKZDIOGTMKL-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
230000007935 neutral effect Effects 0.000 claims 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 claims description 2
KVIBTFADRSQCPG-UHFFFAOYSA-N 4,8-dichloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C(Cl)C=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 KVIBTFADRSQCPG-UHFFFAOYSA-N 0.000 claims description 2
VIUAZVROTZOVGV-UHFFFAOYSA-N 4-chloro-8-fluoro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(Cl)C2=NN=C(C(F)(F)F)N2C2=CC(F)=CC=C21 VIUAZVROTZOVGV-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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 claims description 2
238000004519 manufacturing process Methods 0.000 claims 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
230000010933 acylation Effects 0.000 claims 3
238000005917 acylation reaction Methods 0.000 claims 3
229910021529 ammonia Inorganic materials 0.000 claims 3
238000005576 amination reaction Methods 0.000 claims 2
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims 2
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 claims 2
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical class FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
XSJMOLCRLLDSFM-UHFFFAOYSA-N 2h-triazolo[4,5-f]quinoxaline Chemical compound C1=CC2=NC=CN=C2C2=NNN=C21 XSJMOLCRLLDSFM-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
150000008282 halocarbons Chemical group 0.000 claims 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 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 5
208000024891 symptom Diseases 0.000 abstract description 3
125000001153 fluoro group Chemical group F* 0.000 abstract description 2
125000003277 amino group Chemical group 0.000 abstract 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
239000000203 mixture Substances 0.000 description 82
238000002360 preparation method Methods 0.000 description 71
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 66
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
238000001819 mass spectrum Methods 0.000 description 57
239000000047 product Substances 0.000 description 55
239000002244 precipitate Substances 0.000 description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000011541 reaction mixture Substances 0.000 description 44
238000001914 filtration Methods 0.000 description 40
PDOPFYRTIVSUKL-UHFFFAOYSA-N 4-(azepan-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical class C1CCCCCN1C1=NC2=CC=CC=C2N2C1=NN=C2 PDOPFYRTIVSUKL-UHFFFAOYSA-N 0.000 description 37
239000000243 solution Substances 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
229960001701 chloroform Drugs 0.000 description 30
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 27
239000007787 solid Substances 0.000 description 22
238000001953 recrystallisation Methods 0.000 description 19
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
238000001704 evaporation Methods 0.000 description 17
230000008020 evaporation Effects 0.000 description 17
239000012299 nitrogen atmosphere Substances 0.000 description 17
239000012265 solid product Substances 0.000 description 17
239000002274 desiccant Substances 0.000 description 16
238000010907 mechanical stirring Methods 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
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
239000002002 slurry Substances 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
238000000967 suction filtration Methods 0.000 description 10
238000003756 stirring Methods 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
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 8
239000007789 gas Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
239000000463 material Substances 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
150000003512 tertiary amines Chemical class 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
229960000583 acetic acid Drugs 0.000 description 5
230000001430 anti-depressive effect Effects 0.000 description 5
239000000935 antidepressant agent Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
229960005419 nitrogen Drugs 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 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
UVCAWLYCXOGQFU-UHFFFAOYSA-N (6-chloro-3-methoxyquinoxalin-2-yl)hydrazine Chemical compound ClC1=CC=C2N=C(NN)C(OC)=NC2=C1 UVCAWLYCXOGQFU-UHFFFAOYSA-N 0.000 description 4
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 4
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 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
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000002929 anti-fatigue Effects 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
150000003252 quinoxalines Chemical class 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
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 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
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 3
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 3
DORABZLBYMIEQT-UHFFFAOYSA-N 2,6-dichloro-3-methoxyquinoxaline Chemical compound ClC1=CC=C2N=C(Cl)C(OC)=NC2=C1 DORABZLBYMIEQT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
KUOHTIBWFUNFFJ-UHFFFAOYSA-N 2-chloro-6-fluoro-3-methoxyquinoxaline Chemical compound FC1=CC=C2N=C(Cl)C(OC)=NC2=C1 KUOHTIBWFUNFFJ-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
CHTYMWBYHAIEOF-UHFFFAOYSA-N 6-methoxy-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=CC(OC)=CC=C21 CHTYMWBYHAIEOF-UHFFFAOYSA-N 0.000 description 3
CLXSHMROIMQRIZ-UHFFFAOYSA-N 7-chloro-4-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=NC2=CC(Cl)=CC=C2N2C1=NN=C2 CLXSHMROIMQRIZ-UHFFFAOYSA-N 0.000 description 3
YSRIRSNQYYQFGX-UHFFFAOYSA-N 7-chloro-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound OC1=NC2=CC(Cl)=CC=C2N2C1=NN=C2 YSRIRSNQYYQFGX-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
XWUFWWOEPUVRDP-UHFFFAOYSA-N 7-methoxy-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound N1=C(O)C2=NN=CN2C2=CC=C(OC)C=C21 XWUFWWOEPUVRDP-UHFFFAOYSA-N 0.000 description 3
QEBKKQORZMWUIS-UHFFFAOYSA-N 8-fluoro-1-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound OC1=NC2=CC=C(F)C=C2N2C1=NN=C2C(F)(F)F QEBKKQORZMWUIS-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
238000007605 air drying Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
FLHYALNCDIJUPF-UHFFFAOYSA-N n,n,1-triethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=C(OC)C=C2N2C1=NN=C2CC FLHYALNCDIJUPF-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
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
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
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 2
NFJQDGNCJJPQNV-UHFFFAOYSA-N 2,3-dichloro-6-methoxyquinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(OC)=CC=C21 NFJQDGNCJJPQNV-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
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
SLRKJWIVACQHPF-UHFFFAOYSA-N 4,7-dimethoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(OC)C2=NN=CN2C2=CC=C(OC)C=C21 SLRKJWIVACQHPF-UHFFFAOYSA-N 0.000 description 2
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 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
UMVDJYCXBVQRFE-UHFFFAOYSA-N 4-chloro-1-ethyl-7-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 UMVDJYCXBVQRFE-UHFFFAOYSA-N 0.000 description 2
VHAHGJBWPVLYCF-UHFFFAOYSA-N 4-chloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(Cl)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1 VHAHGJBWPVLYCF-UHFFFAOYSA-N 0.000 description 2
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 2
RNOLFZACEWWIHP-UHFFFAOYSA-N 6-chloro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=CC(Cl)=CC=C21 RNOLFZACEWWIHP-UHFFFAOYSA-N 0.000 description 2
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 2
BURIFIXTNVTJJN-UHFFFAOYSA-N 6-methoxyquinoxaline Chemical compound N1=CC=NC2=CC(OC)=CC=C21 BURIFIXTNVTJJN-UHFFFAOYSA-N 0.000 description 2
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 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000193803 Therea Species 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
239000012458 free base Substances 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
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 2
XNECKOPNMFWEJN-UHFFFAOYSA-N n,n-diethyl-1-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=CC=C2N2C1=NN=C2C XNECKOPNMFWEJN-UHFFFAOYSA-N 0.000 description 2
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 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
GULVDPYLWVXKGC-UHFFFAOYSA-N quinoxalin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=CN=C21 GULVDPYLWVXKGC-UHFFFAOYSA-N 0.000 description 2
230000009182 swimming Effects 0.000 description 2
239000003826 tablet Substances 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
238000005406 washing Methods 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
SOHAVULMGIITDH-ZXPSTKSJSA-N (1S,9R,14E)-14-(1H-imidazol-5-ylmethylidene)-2,11-dimethoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7,10-tetraene-12,15-dione Chemical compound C([C@]1(C2=CC=CC=C2N([C@@]21NC1=O)OC)C(C)(C)C=C)=C(OC)C(=O)N2\C1=C\C1=CNC=N1 SOHAVULMGIITDH-ZXPSTKSJSA-N 0.000 description 1
GTNSFAOLXHSIRQ-UHFFFAOYSA-N (2,6-dichloro-5h-quinoxalin-6-yl)hydrazine Chemical compound C1=C(Cl)N=C2C=CC(NN)(Cl)CC2=N1 GTNSFAOLXHSIRQ-UHFFFAOYSA-N 0.000 description 1
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 1
ZDHGWFYCWYSLNG-UHFFFAOYSA-N (3-chloro-7-methoxyquinoxalin-2-yl)hydrazine 2,3-dichloro-6-methoxyquinoxaline Chemical compound ClC1=NC2=CC=C(C=C2N=C1Cl)OC.ClC1=NC2=CC=C(C=C2N=C1NN)OC ZDHGWFYCWYSLNG-UHFFFAOYSA-N 0.000 description 1
DJDCXKFNQNCXRQ-UHFFFAOYSA-N (3-methoxyquinoxalin-2-yl)hydrazine Chemical class C1=CC=C2N=C(NN)C(OC)=NC2=C1 DJDCXKFNQNCXRQ-UHFFFAOYSA-N 0.000 description 1
FQJMHCIJFGVJAA-UHFFFAOYSA-N 1,1,1-triethoxy-2-methylpropane Chemical compound CCOC(OCC)(OCC)C(C)C FQJMHCIJFGVJAA-UHFFFAOYSA-N 0.000 description 1
KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
ZNYWJFOJWHZDNV-UHFFFAOYSA-N 1-ethyl-7-fluoro-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound FC1=CC=C2N3C(CC)=NN=C3C(O)=NC2=C1 ZNYWJFOJWHZDNV-UHFFFAOYSA-N 0.000 description 1
XCOKDBGGIMCORR-UHFFFAOYSA-N 1-ethyl-7-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.COC1=CC=C2N3C(CC)=NN=C3C(N)=NC2=C1 XCOKDBGGIMCORR-UHFFFAOYSA-N 0.000 description 1
KXJJKKIOVZHZQY-UHFFFAOYSA-N 1-ethyl-n,n-dimethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound C1=CC=C2N3C(CC)=NN=C3C(N(C)C)=NC2=C1 KXJJKKIOVZHZQY-UHFFFAOYSA-N 0.000 description 1
LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
ATCBVQIAXQWBNG-UHFFFAOYSA-N 2,3,6,7-tetrachloroquinoxaline (3,6,7-trichloroquinoxalin-2-yl)hydrazine Chemical compound ClC1=NC2=CC(=C(C=C2N=C1Cl)Cl)Cl.ClC1=NC2=CC(=C(C=C2N=C1NN)Cl)Cl ATCBVQIAXQWBNG-UHFFFAOYSA-N 0.000 description 1
NGEVWMRKYXCRMF-UHFFFAOYSA-N 2,3-difluoroquinoxaline Chemical compound C1=CC=C2N=C(F)C(F)=NC2=C1 NGEVWMRKYXCRMF-UHFFFAOYSA-N 0.000 description 1
MXLKSKWDWYRBHD-UHFFFAOYSA-N 2-chloro-3,6-dimethoxyquinoxaline Chemical compound N1=C(Cl)C(OC)=NC2=CC(OC)=CC=C21 MXLKSKWDWYRBHD-UHFFFAOYSA-N 0.000 description 1
TTXKLKHPMYZIAE-UHFFFAOYSA-N 2-chloro-3-methoxyquinoxaline Chemical class C1=CC=C2N=C(Cl)C(OC)=NC2=C1 TTXKLKHPMYZIAE-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
BZVDLUPGFIHWRF-UHFFFAOYSA-N 4,7-dichloro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N1=C(Cl)C2=NN=CN2C2=CC=C(Cl)C=C21 BZVDLUPGFIHWRF-UHFFFAOYSA-N 0.000 description 1
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 1
BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
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 1
WXWMEEGJJIJVOK-UHFFFAOYSA-N 4-chloro-1-ethyl-8-fluoro-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C(F)C=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 WXWMEEGJJIJVOK-UHFFFAOYSA-N 0.000 description 1
WVRPYBUNBOEXLQ-UHFFFAOYSA-N 4-chloro-1-ethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C(OC)C=C2N3C(CC)=NN=C3C(Cl)=NC2=C1 WVRPYBUNBOEXLQ-UHFFFAOYSA-N 0.000 description 1
VUJDRJSOJVPGAL-UHFFFAOYSA-N 4-chloro-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline (3-chloroquinoxalin-2-yl)hydrazine Chemical compound ClC1=NC2=CC=CC=C2N=C1NN.ClC=1C=2N(C3=CC=CC=C3N1)C(=NN2)C2=CC=CC=C2 VUJDRJSOJVPGAL-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
KWEWNOOZQVJONF-UHFFFAOYSA-N 4-fluorobenzene-1,2-diamine Chemical compound NC1=CC=C(F)C=C1N KWEWNOOZQVJONF-UHFFFAOYSA-N 0.000 description 1
AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
UDVLWGZLJFQYGP-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine;hydrochloride Chemical compound Cl.COC1=CC=C(N)C(N)=C1 UDVLWGZLJFQYGP-UHFFFAOYSA-N 0.000 description 1
ZPWMPGZCEXPDAS-UHFFFAOYSA-N 5-methoxyquinoxaline Chemical compound C1=CN=C2C(OC)=CC=CC2=N1 ZPWMPGZCEXPDAS-UHFFFAOYSA-N 0.000 description 1
IQUVMOWIZMLZIA-VOTSOKGWSA-N 6-[(e)-2-phenylethenyl]pyrimidine-2,4,5-triamine Chemical compound NC1=NC(N)=C(N)C(\C=C\C=2C=CC=CC=2)=N1 IQUVMOWIZMLZIA-VOTSOKGWSA-N 0.000 description 1
FKKFICHINCMWRB-UHFFFAOYSA-N 7,8-dibromo-n,n-diethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC(Br)=C(Br)C=C2N2C1=NN=C2 FKKFICHINCMWRB-UHFFFAOYSA-N 0.000 description 1
VBQLSZNBNNIMKE-UHFFFAOYSA-N 7,8-dichloro-1-ethyl-n,n-dimethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound ClC1=C(Cl)C=C2N3C(CC)=NN=C3C(N(C)C)=NC2=C1 VBQLSZNBNNIMKE-UHFFFAOYSA-N 0.000 description 1
DSUJQNZJHHBYPV-UHFFFAOYSA-N 7,8-dichloro-1-ethyl-n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound ClC1=C(Cl)C=C2N3C(CC)=NN=C3C(NC(C)C)=NC2=C1 DSUJQNZJHHBYPV-UHFFFAOYSA-N 0.000 description 1
OVGXRVCCGHVHKU-UHFFFAOYSA-N 7,8-dichloro-n,n,1-triethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC(Cl)=C(Cl)C=C2N2C1=NN=C2CC OVGXRVCCGHVHKU-UHFFFAOYSA-N 0.000 description 1
HJNDUPABZVKTOL-UHFFFAOYSA-N 7-chloro-1-ethyl-4-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound ClC1=CC=C2N3C(CC)=NN=C3C(OC)=NC2=C1 HJNDUPABZVKTOL-UHFFFAOYSA-N 0.000 description 1
IIRJCZTUCVMLPE-UHFFFAOYSA-N 7-chloro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.NC1=NC2=CC(Cl)=CC=C2N2C1=NN=C2 IIRJCZTUCVMLPE-UHFFFAOYSA-N 0.000 description 1
PQDMOVHFEJISKE-UHFFFAOYSA-N 7-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound N1=C(N)C2=NN=CN2C2=CC=C(OC)C=C21 PQDMOVHFEJISKE-UHFFFAOYSA-N 0.000 description 1
ABXBWLHLNNKNIO-UHFFFAOYSA-N 8-chloro-1-(1,1,2,2,2-pentafluoroethyl)-n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CC(C)NC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2C(F)(F)C(F)(F)F ABXBWLHLNNKNIO-UHFFFAOYSA-N 0.000 description 1
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 1
JORCMIACBHYGGJ-UHFFFAOYSA-N 8-chloro-1-ethyl-n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound C1=C(Cl)C=C2N3C(CC)=NN=C3C(NC(C)C)=NC2=C1 JORCMIACBHYGGJ-UHFFFAOYSA-N 0.000 description 1
FCSAYHXPCNJZPC-UHFFFAOYSA-N 8-chloro-1-phenyl-n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound N=1N=C2C(NC(C)C)=NC3=CC=C(Cl)C=C3N2C=1C1=CC=CC=C1 FCSAYHXPCNJZPC-UHFFFAOYSA-N 0.000 description 1
GMXHWEQJELPOPD-UHFFFAOYSA-N 8-chloro-n-ethyl-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2C(F)(F)F GMXHWEQJELPOPD-UHFFFAOYSA-N 0.000 description 1
SPIXJGUPZUGTCJ-UHFFFAOYSA-N 8-chloro-n-propan-2-yl-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CC(C)NC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2C(F)(F)F SPIXJGUPZUGTCJ-UHFFFAOYSA-N 0.000 description 1
XZXVDBBPURDNMY-UHFFFAOYSA-N 8-chloro-n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CC(C)NC1=NC2=CC=C(Cl)C=C2N2C1=NN=C2 XZXVDBBPURDNMY-UHFFFAOYSA-N 0.000 description 1
UOCJHVTVJYSDBW-UHFFFAOYSA-N 8-fluoro-1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;hydrate Chemical compound O.NC1=NC2=CC=C(F)C=C2N2C1=NN=C2C(F)(F)F UOCJHVTVJYSDBW-UHFFFAOYSA-N 0.000 description 1
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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
JFWKAHHKBLUQCK-UHFFFAOYSA-N C(C)(C)N.C(C)(C)NC=1C=2N(C3=CC=CC=C3N1)C(=NN2)CC Chemical compound C(C)(C)N.C(C)(C)NC=1C=2N(C3=CC=CC=C3N1)C(=NN2)CC JFWKAHHKBLUQCK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
RZPBGPGWCIDWQV-UHFFFAOYSA-N ClC1=NC2=CC=C(C=C2N=C1NN)Cl.ClC=1C=2N(C3=CC(=CC=C3N1)Cl)C(=NN2)CC Chemical compound ClC1=NC2=CC=C(C=C2N=C1NN)Cl.ClC=1C=2N(C3=CC(=CC=C3N1)Cl)C(=NN2)CC RZPBGPGWCIDWQV-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
CJOLNRGADHRZLR-UHFFFAOYSA-N N1=CC=NC2=CC=CC=C12.CS(=O)(=O)O Chemical compound N1=CC=NC2=CC=CC=C12.CS(=O)(=O)O CJOLNRGADHRZLR-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
SOHAVULMGIITDH-UHFFFAOYSA-N Oxaline Natural products O=C1NC23N(OC)C4=CC=CC=C4C3(C(C)(C)C=C)C=C(OC)C(=O)N2C1=CC1=CN=CN1 SOHAVULMGIITDH-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
PIRYKGLQLCKQPG-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline Chemical class C1=CC=C2N3C=NN=C3C=CC2=C1 PIRYKGLQLCKQPG-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000001990 intravenous administration Methods 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
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
SKHKSKDLKNGGIZ-UHFFFAOYSA-N n,n-diethyl-1-propyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound C1=CC=C2N3C(CCC)=NN=C3C(N(CC)CC)=NC2=C1 SKHKSKDLKNGGIZ-UHFFFAOYSA-N 0.000 description 1
QVRRWWIJVINRMQ-UHFFFAOYSA-N n,n-diethyl-7,8-difluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCN(CC)C1=NC2=CC(F)=C(F)C=C2N2C1=NN=C2 QVRRWWIJVINRMQ-UHFFFAOYSA-N 0.000 description 1
TZGBMTDINFCZKO-UHFFFAOYSA-N n,n-diethyl-8-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCN(CC)C1=NC2=CC=C(OC)C=C2N2C1=NN=C2 TZGBMTDINFCZKO-UHFFFAOYSA-N 0.000 description 1
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 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
FCDVHOZOJKPZHZ-UHFFFAOYSA-N n-(1-ethyl-7-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)acetamide Chemical compound COC1=CC=C2N3C(CC)=NN=C3C(NC(C)=O)=NC2=C1 FCDVHOZOJKPZHZ-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
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
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
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
KCIVMWQULBVJRF-UHFFFAOYSA-N n-ethyl-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CCNC1=NC2=CC(F)=CC=C2N2C1=NN=C2 KCIVMWQULBVJRF-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
XFWPLYABTZBENI-UHFFFAOYSA-N n-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical compound CC(C)NC1=NC2=CC=CC=C2N2C1=NN=C2 XFWPLYABTZBENI-UHFFFAOYSA-N 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
238000007911 parenteral administration Methods 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000004986 phenylenediamines Chemical class 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus 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
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000012216 screening Methods 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
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
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
229940095064 tartrate Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration 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)

CA000439039A 1982-10-18 1983-10-14 Derives amines de la triazoloquinoxaline Expired CA1207772A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US43477182A	1982-10-18	1982-10-18
US434,771		1982-10-18

Publications (1)

Publication Number	Publication Date
CA1207772A true CA1207772A (fr)	1986-07-15

Family

ID=23725622

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000439039A Expired CA1207772A (fr)	1982-10-18	1983-10-14	Derives amines de la triazoloquinoxaline

Country Status (17)

Country	Link
JP (1)	JPS5989684A (fr)
KR (1)	KR860001493B1 (fr)
CA (1)	CA1207772A (fr)
CS (1)	CS248711B2 (fr)
DD (1)	DD215545A5 (fr)
ES (1)	ES8504197A1 (fr)
FI (1)	FI74011C (fr)
GR (1)	GR78952B (fr)
IN (1)	IN160956B (fr)
NO (1)	NO160142C (fr)
NZ (1)	NZ205986A (fr)
PH (1)	PH19080A (fr)
PL (1)	PL141382B1 (fr)
PT (1)	PT77507B (fr)
SU (1)	SU1246895A3 (fr)
YU (1)	YU43331B (fr)
ZA (1)	ZA837691B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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
EP2489667B1 (fr) *	2006-12-13	2015-04-15	ASKA Pharmaceutical Co., Ltd.	Dérivé de quinoxaline
UY32111A (es) *	2008-09-10	2010-04-30	Alcon Res Ltd	Inhibidores heterociclicos de los receptores de histamina para el tratamiento de una enfermedad
JP5634609B2 (ja) *	2010-09-16	2014-12-03	ハチソンメディファーマリミテッド	縮合ヘテロアリールおよびその使用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 PT PT77507A patent/PT77507B/pt not_active IP Right Cessation
- 1983-10-14 CA CA000439039A patent/CA1207772A/fr not_active Expired
- 1983-10-14 YU YU2074/83A patent/YU43331B/xx unknown
- 1983-10-17 NZ NZ205986A patent/NZ205986A/en unknown
- 1983-10-17 PH PH29702A patent/PH19080A/en unknown
- 1983-10-17 ES ES526533A patent/ES8504197A1/es not_active Expired
- 1983-10-17 SU SU833653375A patent/SU1246895A3/ru active
- 1983-10-17 NO NO833770A patent/NO160142C/no unknown
- 1983-10-17 ZA ZA837691A patent/ZA837691B/xx unknown
- 1983-10-17 DD DD83255716A patent/DD215545A5/de not_active IP Right Cessation
- 1983-10-17 FI FI833781A patent/FI74011C/fi not_active IP Right Cessation
- 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

Also Published As

Publication number	Publication date
FI74011C (fi)	1987-12-10
PH19080A (en)	1985-12-19
DD215545A5 (de)	1984-11-14
JPH039915B2 (fr)	1991-02-12
PT77507A (en)	1983-11-01
ES526533A0 (es)	1985-04-01
ZA837691B (en)	1985-05-29
CS248711B2 (en)	1987-02-12
KR840006485A (ko)	1984-11-30
NO833770L (no)	1984-04-24
JPS5989684A (ja)	1984-05-23
PL141382B1 (en)	1987-07-31
NO160142C (no)	1989-03-15
FI833781A0 (fi)	1983-10-17
YU43331B (en)	1989-06-30
NZ205986A (en)	1986-06-11
KR860001493B1 (ko)	1986-09-27
IN160956B (fr)	1987-08-22
FI833781A (fi)	1984-04-19
PL244194A1 (en)	1985-03-26
FI74011B (fi)	1987-08-31
PT77507B (en)	1986-05-28
YU207483A (en)	1986-02-28
ES8504197A1 (es)	1985-04-01
NO160142B (no)	1988-12-05
GR78952B (fr)	1984-10-02
SU1246895A3 (ru)	1986-07-23

Publication	Publication Date	Title
EP0025819B1 (fr)	1983-10-12	Pyrazolo (1,5-a) pyrimidines substituées et leur préparation
EP0029103B1 (fr)	1983-05-18	6- ou 8-Hétéroaryl-1,2,4-triazolo(4,3-b)pyridazines
AU772947B2 (en)	2004-05-13	Triazolo-pyridazine derivatives as ligands for GABA receptors
CA2258885A1 (fr)	1997-12-31	Les benzazepines: des antagonistes tricycliques de la vasopressine
CA1076572A (fr)	1980-04-29	Derives de la diazepine
AU1719901A (en)	2001-06-25	Pyrazolo-pyridine derivatives as ligands for gaba receptors
Molina et al.	1999	Iminophosphorane-mediated synthesis of the alkaloid cryptotackieine
CA2298522C (fr)	2008-07-15	Derives de 4-oxo-3,5-dihydro-4h-pyridazino[4,5-b] indole-1-acetamide, leur preparation et leur application en therapeutique
CZ291409B6 (cs)	2003-03-12	Substituovaný triazolopyridazinový derivát
CA1207772A (fr)	1986-07-15	Derives amines de la triazoloquinoxaline
EP0126970A2 (fr)	1984-12-05	Dérivés de thiénopyridine anxiolytiques et antidépresseurs
EP0107455B1 (fr)	1986-07-09	Triazoloquinoxalines comme agents antidépresseurs et antifatigue
US4623725A (en)	1986-11-18	[1,2,4]Triazolo[4,3-a]quinoxaline-4-amine derivatives
CA1106371A (fr)	1981-08-04	Quinazolines tricycliques; preparation et application
Biagi et al.	2002	New 1, 2, 3‐triazolo [4, 5‐d] 1, 2, 4‐triazolo [3, 4‐b] pyridazine derivatives II
CA2362400A1 (fr)	2000-08-17	Derives de la triazolo-pyridazine, liants des recepteurs du gaba
Mekheimer et al.	2001	Fused quinoline heterocycles IV: First synthesis of four heterocyclic ring systems of 1H-5-thia-1, 2, 3, 6-tetraazaacephenanthrylenes and 1H-5-thia-1, 3, 6-triazaacephenanthrylenes
Nitta et al.	1992	On the reaction of (vinylimino) phosphoranes and related compounds synthesis and properties of novel 1, 6-methanocyclodeca [b] cyclohepta [d] pyrrole
Giori et al.	1985	Synthesis of 4‐thiocarbamoyl‐5‐aminopyrazoles
Mekheimer et al.	2018	Naphthyridines part 4: unprecedented synthesis of polyfunctionally substituted benzo [c][2, 7] naphthyridines and benzo [c] pyrimido [4, 5, 6-ij][2, 7] naphthyridines with structural analogy to pyrido [4, 3, 2-mn] acridines present in the marine tetracyclic pyridoacridine alkaloids
FI63405C (fi)	1983-06-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara imdazo(1,5-a) (1,4)diazepin-foereningar
Vomero et al.	1990	Synthesis of 1, 2, 4‐triazolo [4′, 3′: 1, 6] pyridazino [4, 5‐b] quinoline derivatives
Riedl et al.	1992	Synthesis and ring transformation of novel tetracyclic fused as-triazines
Esser et al.	1990	Cyclic Guanidines; III1 Synthesis of Novel 8, 13, 15-Triazasteroids and Related Heterocycles
Mekheimer et al.	2001	FUSED QUINOLINE HETEROCYCLES IV. FIRST SYNTHESIS OF FOUR HETEROCYCLIC RING SYSTEMS OF lH-5-THIA-l, 2, 3, 6-TETRA-AZAACEPHENANTHRYLENES AND 1H-5-THIA-l, 3, 6-TRIAZAACEPHENANTHRYLENES

Legal Events

Date	Code	Title	Description
2003-10-14	MKEX	Expiry