NO873945L - Substituerte kinoksaliner. - Google Patents
Substituerte kinoksaliner.Info
- Publication number
- NO873945L NO873945L NO873945A NO873945A NO873945L NO 873945 L NO873945 L NO 873945L NO 873945 A NO873945 A NO 873945A NO 873945 A NO873945 A NO 873945A NO 873945 L NO873945 L NO 873945L
- Authority
- NO
- Norway
- Prior art keywords
- group
- indolo
- lower alkyl
- quinoxaline
- iodine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- NXOVZLREWXNIDP-UHFFFAOYSA-N 7h-pyrazino[2,3-c]carbazole Chemical class N1=CC=NC2=C3C4=CC=CC=C4NC3=CC=C21 NXOVZLREWXNIDP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 6
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- OIVUHPTVQVCONM-UHFFFAOYSA-N 6-bromo-4-methyl-1h-indazole Chemical compound CC1=CC(Br)=CC2=C1C=NN2 OIVUHPTVQVCONM-UHFFFAOYSA-N 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 4
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 3
- 229960005102 foscarnet Drugs 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- GCPRBJCAJXSLFG-UHFFFAOYSA-N 2-(9-bromoindolo[3,2-b]quinoxalin-6-yl)-n,n-dimethylethanamine Chemical class C1=CC=C2N=C3N(CCN(C)C)C4=CC=C(Br)C=C4C3=NC2=C1 GCPRBJCAJXSLFG-UHFFFAOYSA-N 0.000 claims description 2
- 241000450599 DNA viruses Species 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims 4
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- BOPKXNNSPIBTKR-UHFFFAOYSA-N 2-(9-bromo-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)-n,n-dimethylethanamine Chemical compound CC1=C(C)C=C2N=C3N(CCN(C)C)C4=CC=C(Br)C=C4C3=NC2=C1 BOPKXNNSPIBTKR-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 18
- 241000700605 Viruses Species 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- LCKIWLDOHFUYDV-UHFFFAOYSA-N 6h-indolo[3,2-b]quinoxaline Chemical class C1=CC=C2N=C3C4=CC=CC=C4NC3=NC2=C1 LCKIWLDOHFUYDV-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- IMTJKSASESQALZ-UHFFFAOYSA-N 9-methyl-6h-indolo[3,2-b]quinoxaline Chemical compound C1=CC=C2N=C(C=3C(=CC=C(C=3)C)N3)C3=NC2=C1 IMTJKSASESQALZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- FPLSGFJELWCFTH-UHFFFAOYSA-N 2-(2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)-n,n-dimethylethanamine Chemical compound CC1=C(C)C=C2N=C3N(CCN(C)C)C4=CC=CC=C4C3=NC2=C1 FPLSGFJELWCFTH-UHFFFAOYSA-N 0.000 description 2
- LJHHJFAUMZLYRE-UHFFFAOYSA-N 2-(2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)ethyl-dimethylazanium;chloride Chemical compound Cl.CC1=C(C)C=C2N=C3N(CCN(C)C)C4=CC=CC=C4C3=NC2=C1 LJHHJFAUMZLYRE-UHFFFAOYSA-N 0.000 description 2
- IJDYPOSTBQMLKE-UHFFFAOYSA-N 2-(7,9-dichloroindolo[3,2-b]quinoxalin-6-yl)-n,n-dimethylethanamine Chemical compound ClC1=CC(Cl)=C2N(CCN(C)C)C3=NC4=CC=CC=C4N=C3C2=C1 IJDYPOSTBQMLKE-UHFFFAOYSA-N 0.000 description 2
- XLURJWBOXAXBIR-UHFFFAOYSA-N 2-(7h-pyrazino[2,3-c]carbazol-6-yl)acetonitrile Chemical class C12=CC=CC=C2NC2=C1C1=NC=CN=C1C=C2CC#N XLURJWBOXAXBIR-UHFFFAOYSA-N 0.000 description 2
- MBVCESWADCIXJN-UHFFFAOYSA-N 5-Bromoisatin Chemical compound BrC1=CC=C2NC(=O)C(=O)C2=C1 MBVCESWADCIXJN-UHFFFAOYSA-N 0.000 description 2
- YDUWMXJTLKWJGL-UHFFFAOYSA-N 7,9-dichloro-6h-indolo[3,2-b]quinoxaline Chemical compound C1=CC=C2N=C(C=3C(=C(Cl)C=C(C=3)Cl)N3)C3=NC2=C1 YDUWMXJTLKWJGL-UHFFFAOYSA-N 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 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 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960004716 idoxuridine Drugs 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- MPBRIXMSWIZWQZ-UHFFFAOYSA-N n,n-dimethyl-2-(9-methylindolo[3,2-b]quinoxalin-6-yl)ethanamine Chemical compound C1=CC=C2N=C3N(CCN(C)C)C4=CC=C(C)C=C4C3=NC2=C1 MPBRIXMSWIZWQZ-UHFFFAOYSA-N 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- SAEMKKTVBSCOFX-UHFFFAOYSA-N quinoxalin-1-ium;chloride Chemical compound Cl.N1=CC=NC2=CC=CC=C21 SAEMKKTVBSCOFX-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MKSGOPYONANXAX-UHFFFAOYSA-N 1-(7h-pyrazino[2,3-c]carbazol-6-yl)ethanone Chemical compound C12=CC=CC=C2NC2=C1C1=NC=CN=C1C=C2C(=O)C MKSGOPYONANXAX-UHFFFAOYSA-N 0.000 description 1
- RICDAKOKYPOJPN-UHFFFAOYSA-N 1-n,4-dimethylbenzene-1,2-diamine Chemical compound CNC1=CC=C(C)C=C1N RICDAKOKYPOJPN-UHFFFAOYSA-N 0.000 description 1
- YIAHNRWCBYVXCG-UHFFFAOYSA-N 2-(2,3,9-trichloroindolo[3,2-b]quinoxalin-6-yl)acetonitrile Chemical compound ClC1=C(Cl)C=C2N=C(C=3C(=CC=C(C=3)Cl)N3CC#N)C3=NC2=C1 YIAHNRWCBYVXCG-UHFFFAOYSA-N 0.000 description 1
- NPJHZYPWLNSFOT-UHFFFAOYSA-N 2-(2,3-dichloroindolo[3,2-b]quinoxalin-6-yl)acetonitrile Chemical compound N#CCN1C2=CC=CC=C2C2=C1N=C1C=C(Cl)C(Cl)=CC1=N2 NPJHZYPWLNSFOT-UHFFFAOYSA-N 0.000 description 1
- MKJOQTOVHKIEIJ-UHFFFAOYSA-N 2-(2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)acetonitrile Chemical compound N#CCN1C2=CC=CC=C2C2=C1N=C1C=C(C)C(C)=CC1=N2 MKJOQTOVHKIEIJ-UHFFFAOYSA-N 0.000 description 1
- HBZXFXUHGCXHGB-UHFFFAOYSA-N 2-(3-indolo[3,2-b]quinoxalin-6-ylpropyl)isoindole-1,3-dione;7h-pyrazino[2,3-c]carbazole Chemical compound N1=CC=NC2=C3C4=CC=CC=C4NC3=CC=C21.O=C1C2=CC=CC=C2C(=O)N1CCCN1C2=NC3=CC=CC=C3N=C2C2=CC=CC=C21 HBZXFXUHGCXHGB-UHFFFAOYSA-N 0.000 description 1
- GSFZNDDKJOYTBC-UHFFFAOYSA-N 2-(7,9-dichloroindolo[2,3-b]quinoxalin-5-yl)-n,n-dimethylethanamine Chemical compound C1=CC=C2N(CCN(C)C)C3=NC4=C(Cl)C=C(Cl)C=C4C3=NC2=C1 GSFZNDDKJOYTBC-UHFFFAOYSA-N 0.000 description 1
- PYQUUOYXHJSKOL-UHFFFAOYSA-N 2-(7h-pyrazino[2,3-c]carbazol-6-yl)ethanamine Chemical class C12=CC=CC=C2NC2=C1C1=NC=CN=C1C=C2CCN PYQUUOYXHJSKOL-UHFFFAOYSA-N 0.000 description 1
- XNBXZDGANFMQOF-UHFFFAOYSA-N 2-(9-bromoindolo[2,3-b]quinoxalin-5-yl)-n,n-dimethylethanamine Chemical compound C1=CC=C2N(CCN(C)C)C3=NC4=CC=C(Br)C=C4C3=NC2=C1 XNBXZDGANFMQOF-UHFFFAOYSA-N 0.000 description 1
- LWCDOTUUXBYEPN-UHFFFAOYSA-N 2-(9-chloro-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)acetonitrile Chemical compound N#CCN1C2=CC=C(Cl)C=C2C2=C1N=C1C=C(C)C(C)=CC1=N2 LWCDOTUUXBYEPN-UHFFFAOYSA-N 0.000 description 1
- QTHZSOCUYIEBFK-UHFFFAOYSA-N 2-(9-fluoroindolo[3,2-b]quinoxalin-6-yl)-n,n-dimethylethanamine Chemical compound C1=CC=C2N=C3N(CCN(C)C)C4=CC=C(F)C=C4C3=NC2=C1 QTHZSOCUYIEBFK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ASPCGJCAQYNHEN-UHFFFAOYSA-N 2-indolo[3,2-b]quinoxalin-6-yl-n,n-dimethylethanamine Chemical compound C1=CC=C2N=C3N(CCN(C)C)C4=CC=CC=C4C3=NC2=C1 ASPCGJCAQYNHEN-UHFFFAOYSA-N 0.000 description 1
- DLFBQGAOONYSEM-UHFFFAOYSA-N 2-indolo[3,2-b]quinoxalin-6-ylacetonitrile Chemical compound C1=CC=C2N=C3N(CC#N)C4=CC=CC=C4C3=NC2=C1 DLFBQGAOONYSEM-UHFFFAOYSA-N 0.000 description 1
- GDNBIYLDDMJRCC-UHFFFAOYSA-N 2-indolo[3,2-b]quinoxalin-6-ylethanamine Chemical compound C1=CC=C2N=C3N(CCN)C4=CC=CC=C4C3=NC2=C1 GDNBIYLDDMJRCC-UHFFFAOYSA-N 0.000 description 1
- YMYPZBOBAISUFL-UHFFFAOYSA-N 2-n-[2-(dimethylamino)ethyl]benzene-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC=C1N YMYPZBOBAISUFL-UHFFFAOYSA-N 0.000 description 1
- ASCFNMCAHFUBCO-UHFFFAOYSA-N 2-phosphoglycolic acid Chemical compound OC(=O)COP(O)(O)=O ASCFNMCAHFUBCO-UHFFFAOYSA-N 0.000 description 1
- PWSXRGRLZKVHLW-UHFFFAOYSA-N 2-phosphonobutanoic acid Chemical compound CCC(C(O)=O)P(O)(O)=O PWSXRGRLZKVHLW-UHFFFAOYSA-N 0.000 description 1
- GUXRZQZCNOHHDO-UHFFFAOYSA-N 2-phosphonopropanoic acid Chemical compound OC(=O)C(C)P(O)(O)=O GUXRZQZCNOHHDO-UHFFFAOYSA-N 0.000 description 1
- FGUQUQGDGYJKQE-UHFFFAOYSA-N 3-indolo[3,2-b]quinoxalin-6-ylpropan-1-amine Chemical compound C1=CC=C2N=C3N(CCCN)C4=CC=CC=C4C3=NC2=C1 FGUQUQGDGYJKQE-UHFFFAOYSA-N 0.000 description 1
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
- LXXBKUAERYNQSU-UHFFFAOYSA-N 4-(3-chloropropyl)isoindole-1,3-dione Chemical compound ClCCCC1=CC=CC2=C1C(=O)NC2=O LXXBKUAERYNQSU-UHFFFAOYSA-N 0.000 description 1
- GAJZZYYAWHQFJT-UHFFFAOYSA-N 4-[2-(9-bromo-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)ethyl]morpholine Chemical compound C12=CC=C(Br)C=C2C=2N=C3C=C(C)C(C)=CC3=NC=2N1CCN1CCOCC1 GAJZZYYAWHQFJT-UHFFFAOYSA-N 0.000 description 1
- MYTGFBZJLDLWQG-UHFFFAOYSA-N 5-chloro-1h-indole Chemical compound ClC1=CC=C2NC=CC2=C1 MYTGFBZJLDLWQG-UHFFFAOYSA-N 0.000 description 1
- VAJCSPZKMVQIAP-UHFFFAOYSA-N 5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1 VAJCSPZKMVQIAP-UHFFFAOYSA-N 0.000 description 1
- ZTSUWPSOFQDDNY-UHFFFAOYSA-N 6-methyl-6-nitrosocyclohexa-2,4-dien-1-amine Chemical class O=NC1(C)C=CC=CC1N ZTSUWPSOFQDDNY-UHFFFAOYSA-N 0.000 description 1
- NAWHWUNRWBYDAI-UHFFFAOYSA-N 9-bromo-2,3-dimethyl-6h-indolo[3,2-b]quinoxaline Chemical compound N1C2=CC=C(Br)C=C2C2=C1N=C1C=C(C)C(C)=CC1=N2 NAWHWUNRWBYDAI-UHFFFAOYSA-N 0.000 description 1
- XKYKUVXLRPWNLL-UHFFFAOYSA-N 9-bromo-2-methyl-6h-indolo[2,3-b]quinoxaline Chemical class C1=C(Br)C=C2C3=NC4=CC(C)=CC=C4N=C3NC2=C1 XKYKUVXLRPWNLL-UHFFFAOYSA-N 0.000 description 1
- PSLOAFHZTHDLHB-UHFFFAOYSA-N 9-chloro-6h-indolo[3,2-b]quinoxaline Chemical compound C1=CC=C2N=C(C=3C(=CC=C(C=3)Cl)N3)C3=NC2=C1 PSLOAFHZTHDLHB-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000011691 Burkitt lymphomas Diseases 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
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241001136003 Human T-lymphotropic virus 3 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- QXGOTKHNSYEDRC-HCWSKCQFSA-N O[C@@H]1[C@H](O)[C@@H](CO)O[C@@]1(OI)N1C(=O)NC(=O)C=C1 Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@@]1(OI)N1C(=O)NC(=O)C=C1 QXGOTKHNSYEDRC-HCWSKCQFSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 210000001691 amnion Anatomy 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003602 anti-herpes Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- MKRZFAUZBYXFCC-UHFFFAOYSA-N n,4-dimethyl-2-nitrosoaniline Chemical compound CNC1=CC=C(C)C=C1N=O MKRZFAUZBYXFCC-UHFFFAOYSA-N 0.000 description 1
- SZDCTEHAJRYQGF-UHFFFAOYSA-N n,n-dimethyl-2-(9-methylindolo[2,3-b]quinoxalin-5-yl)ethanamine Chemical compound C1=CC=C2N(CCN(C)C)C3=NC4=CC=C(C)C=C4C3=NC2=C1 SZDCTEHAJRYQGF-UHFFFAOYSA-N 0.000 description 1
- ALXPKWZTMGBJDI-UHFFFAOYSA-N n-[2-(9-bromo-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)ethyl]-n-propan-2-ylpropan-2-amine Chemical compound CC1=C(C)C=C2N=C3N(CCN(C(C)C)C(C)C)C4=CC=C(Br)C=C4C3=NC2=C1 ALXPKWZTMGBJDI-UHFFFAOYSA-N 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical class C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000005623 oxindoles Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JTFHKOYORZAXSV-UHFFFAOYSA-K trisodium phosphonoformate hexahydrate Chemical compound O.O.O.O.O.O.[Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O JTFHKOYORZAXSV-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 238000005406 washing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8600260A SE8600260D0 (sv) | 1986-01-21 | 1986-01-21 | Substituerade indolokinoxaliner |
| PCT/SE1987/000019 WO1987004436A1 (en) | 1986-01-21 | 1987-01-19 | Substituted indoloquinoxalines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO873945L true NO873945L (no) | 1987-09-21 |
| NO873945D0 NO873945D0 (no) | 1987-09-21 |
Family
ID=20363170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO873945A NO873945D0 (no) | 1986-01-21 | 1987-09-21 | Substituerte kinoksaliner. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4990510A (es) |
| EP (1) | EP0238459B1 (es) |
| JP (1) | JPH07107066B2 (es) |
| KR (1) | KR880700801A (es) |
| AP (1) | AP27A (es) |
| AT (1) | ATE74920T1 (es) |
| AU (1) | AU606047B2 (es) |
| CA (1) | CA1303613C (es) |
| DE (1) | DE3778190D1 (es) |
| DK (1) | DK492587D0 (es) |
| ES (1) | ES2037105T3 (es) |
| FI (1) | FI883373A (es) |
| HU (1) | HU201937B (es) |
| IL (1) | IL81209A (es) |
| NO (1) | NO873945D0 (es) |
| OA (1) | OA08744A (es) |
| RU (1) | RU1776259C (es) |
| SE (1) | SE8600260D0 (es) |
| WO (1) | WO1987004436A1 (es) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8600261D0 (sv) * | 1986-01-21 | 1986-01-21 | Lundblad Leif | Indolokinoxaliner med substituenter i 6-position som innehaller cykliska grupper |
| EP0695754A4 (en) * | 1993-04-22 | 1997-06-11 | Taisho Pharmaceutical Co Ltd | INDOLO [2,3-b] QUINOXALINE DERIVATIVES |
| US5700823A (en) * | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| SE504289C2 (sv) * | 1994-06-23 | 1996-12-23 | Leif J I Lundblad | Användning av vissa indolo-2,3b-kinoxaliner för framställning av ett läkemedel för inhibering av enzymet HIV-integras |
| SE504862C2 (sv) * | 1994-12-27 | 1997-05-20 | Leif J I Lundblad | Användning av vissa indolo-§2,3b¤-kinoxaliner för framställning av ett läkemedel för skydd av DNA i initieringsfasen och/eller promotionsfasen av karcinogenes och för förhindrande av oxidativ stress i patienter med sjukdomar relaterade till fria radikaler |
| US5721277A (en) * | 1995-04-21 | 1998-02-24 | Sugen, Inc. | Compounds and methods for inhibiting hyper-proliferative cell growth |
| US6331555B1 (en) | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| US6465466B1 (en) | 1995-12-22 | 2002-10-15 | Leif J. I. Lundblad | Uses of indolo-2 [2,3b] -quinoxalines |
| US6316479B1 (en) | 1997-05-19 | 2001-11-13 | Sugen, Inc. | Isoxazole-4-carboxamide compounds active against protein tryosine kinase related disorders |
| SE9704723D0 (sv) * | 1997-12-17 | 1997-12-17 | Leif J I Lundblad | Ligands |
| SE516067C2 (sv) * | 2000-02-18 | 2001-11-12 | Lundblad Leif J I | Användning av en förening för framställning av ett läkemedel |
| US6333327B2 (en) * | 2000-02-18 | 2001-12-25 | Leif J. I. Lundblad | Method for the treatment of Multiple Sclerosis |
| GB0022922D0 (en) * | 2000-09-19 | 2000-11-01 | Chapman Robert E | Compounds for use in medicine |
| SE529777C2 (sv) | 2006-01-23 | 2007-11-20 | Vironova Ab | Nya föreningar och användning därav |
| EP2128160B1 (en) | 2008-04-30 | 2010-07-14 | Universität Duisburg-Essen | Indolo[2,3-b]-, Indeno[1,2-b]- and Indeno[2,1-b]pyrido[2,3-f] quinoxaline-3-carboxylic acids and esters, processes for their preparation and their use as antiviral, antibiotic and antitumor agents |
| EP2489354A1 (en) | 2011-02-18 | 2012-08-22 | Vironova AB | Pharmaceutical formulation of B220 for topical treatment of herpes |
| CN105061432B (zh) * | 2015-07-16 | 2017-09-29 | 河北大学 | 6H‑吲哚[2,3‑b]喹喔啉衍生物、药物组合物及其制备和应用 |
| WO2022002898A1 (en) * | 2020-06-29 | 2022-01-06 | Vironova Medical Ab | 6h-indolo(2,3-b)quinoxaline derivatives useful in therapy in particular in a virus infection |
| US20230312578A1 (en) * | 2020-06-29 | 2023-10-05 | Vironova Medical Ab | 6h-indolo[2,3-b]quinoxaline derivatives useful in therapy |
-
1986
- 1986-01-21 SE SE8600260A patent/SE8600260D0/xx unknown
-
1987
- 1987-01-08 IL IL81209A patent/IL81209A/xx not_active IP Right Cessation
- 1987-01-09 AP APAP/P/1987/000055A patent/AP27A/en active
- 1987-01-19 JP JP62500757A patent/JPH07107066B2/ja not_active Expired - Fee Related
- 1987-01-19 AT AT87850012T patent/ATE74920T1/de not_active IP Right Cessation
- 1987-01-19 DE DE8787850012T patent/DE3778190D1/de not_active Expired - Lifetime
- 1987-01-19 AU AU68995/87A patent/AU606047B2/en not_active Ceased
- 1987-01-19 US US07/102,147 patent/US4990510A/en not_active Expired - Lifetime
- 1987-01-19 WO PCT/SE1987/000019 patent/WO1987004436A1/en active Application Filing
- 1987-01-19 HU HU847A patent/HU201937B/hu not_active IP Right Cessation
- 1987-01-19 EP EP87850012A patent/EP0238459B1/en not_active Expired - Lifetime
- 1987-01-19 ES ES198787850012T patent/ES2037105T3/es not_active Expired - Lifetime
- 1987-01-20 CA CA000527660A patent/CA1303613C/en not_active Expired - Lifetime
- 1987-09-18 DK DK492587A patent/DK492587D0/da not_active Application Discontinuation
- 1987-09-21 NO NO873945A patent/NO873945D0/no unknown
- 1987-09-21 KR KR870700852A patent/KR880700801A/ko not_active Application Discontinuation
-
1988
- 1988-07-15 FI FI883373A patent/FI883373A/fi not_active Application Discontinuation
- 1988-07-19 RU SU884356314A patent/RU1776259C/ru active
- 1988-07-21 OA OA59390A patent/OA08744A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI883373A0 (fi) | 1988-07-15 |
| WO1987004436A1 (en) | 1987-07-30 |
| DK492587A (da) | 1987-09-18 |
| DK492587D0 (da) | 1987-09-18 |
| KR880700801A (ko) | 1988-04-12 |
| AU606047B2 (en) | 1991-01-31 |
| RU1776259C (ru) | 1992-11-15 |
| HU201937B (en) | 1991-01-28 |
| CA1303613C (en) | 1992-06-16 |
| US4990510A (en) | 1991-02-05 |
| AP8700055A0 (en) | 1986-11-01 |
| EP0238459B1 (en) | 1992-04-15 |
| JPH07107066B2 (ja) | 1995-11-15 |
| JPS63502588A (ja) | 1988-09-29 |
| AU6899587A (en) | 1987-08-14 |
| ATE74920T1 (de) | 1992-05-15 |
| AP27A (en) | 1988-12-02 |
| ES2037105T3 (es) | 1993-06-16 |
| FI883373A (fi) | 1988-07-15 |
| HUT47937A (en) | 1989-04-28 |
| IL81209A (en) | 1991-04-15 |
| OA08744A (en) | 1989-03-31 |
| SE8600260D0 (sv) | 1986-01-21 |
| EP0238459A1 (en) | 1987-09-23 |
| IL81209A0 (en) | 1987-08-31 |
| DE3778190D1 (de) | 1992-05-21 |
| NO873945D0 (no) | 1987-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO873945L (no) | Substituerte kinoksaliner. | |
| AU713320B2 (en) | Improved antiviral compounds | |
| USRE42152E1 (en) | Aromatic-linked polyamine macrocyclic compounds with anti-HIV activity | |
| AU734871B2 (en) | New guanidine derivatives, methods of preparing them, and their use as drugs | |
| CA1257272A (en) | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives | |
| HU201773B (en) | Process for producing rebeccamycin analogs and pharmaceutical compositions comprising such active ingredient | |
| AU653024B2 (en) | Substituted diaminophthalimides and analogues | |
| JPS6225670B2 (es) | ||
| EP0031128A1 (en) | (E)-5-(2-halogenovinyl)-arabinofuranosyluracil, process for preparation thereof, and uses thereof | |
| US5491144A (en) | Substituted diaminophthalimides and analogues | |
| US4835160A (en) | Derivatives of pyridoindole, having anti-tumor properties | |
| AU663729B2 (en) | 6((2-hydroxyethyl)aminoalkyl)-5,11-dioxo-5,6-dihydro-11-H- indeno-(1,2-C)isoquinoline and their use as antineoplastic agents | |
| CA1131631A (en) | Quinazoline derivatives and pharmaceutical preparations | |
| FI61886C (fi) | Foerfarande foer framstaellning av i tumoerterapi anvaendbara 1-alkylkarbamoyl-5-fluoruraciler | |
| US4439619A (en) | Fluorinated pentene diamine derivatives | |
| EP0231159B1 (en) | Indoloquinoxalines with substituents in 6-position containing cyclic groups | |
| CA1204770A (en) | Fluorinated diaminoalkene derivatives | |
| JPS6289668A (ja) | ビス−ジオキソピペラジン誘導体及びそれからなる抗腫瘍剤 | |
| IE43095B1 (en) | Novel anthelmintic therapy | |
| JPH04108791A (ja) | チエノ〔３，２―ａ〕インドリジン誘導体 | |
| GB2037763A (en) | 1-amino-indoline derivatives, their preparation and pharmaceutical compositions containing them |