SK286055B6 - Indenoindolónové zlúčeniny, spôsob ich prípravy afarmaceutické kompozície s ich obsahom - Google Patents
Indenoindolónové zlúčeniny, spôsob ich prípravy afarmaceutické kompozície s ich obsahom Download PDFInfo
- Publication number
- SK286055B6 SK286055B6 SK834-2002A SK8342002A SK286055B6 SK 286055 B6 SK286055 B6 SK 286055B6 SK 8342002 A SK8342002 A SK 8342002A SK 286055 B6 SK286055 B6 SK 286055B6
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- branched
- formula
- linear
- indol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 118
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- DTLGNCPQVLQJRC-UHFFFAOYSA-N C1=C2C=CC=CC2=C2C1=C1NC(=O)C=C1C=C2 Chemical class C1=C2C=CC=CC2=C2C1=C1NC(=O)C=C1C=C2 DTLGNCPQVLQJRC-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- -1 amino, carboxy Chemical group 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 16
- 150000002923 oximes Chemical class 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 7
- 150000002431 hydrogen Chemical group 0.000 abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 134
- 238000004452 microanalysis Methods 0.000 description 84
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- CEFBXYRCGUITCZ-UHFFFAOYSA-N o-prop-2-ynylhydroxylamine;hydrochloride Chemical compound Cl.NOCC#C CEFBXYRCGUITCZ-UHFFFAOYSA-N 0.000 description 10
- XLYPHUGUKGMURE-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C(C=O)=C1 XLYPHUGUKGMURE-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- LJKJXQLWGBIHIU-UHFFFAOYSA-N o-(1-phenylprop-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C1=CC=CC=C1 LJKJXQLWGBIHIU-UHFFFAOYSA-N 0.000 description 6
- LWTQNCDTQLWMOU-UHFFFAOYSA-N o-[1-(furan-3-yl)prop-2-ynyl]hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C=1C=COC=1 LWTQNCDTQLWMOU-UHFFFAOYSA-N 0.000 description 6
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 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 4
- 241000699670 Mus sp. Species 0.000 description 4
- XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 4
- NRXXPMKETMJSSI-UHFFFAOYSA-N o-but-3-yn-2-ylhydroxylamine;hydrochloride Chemical compound Cl.NOC(C)C#C NRXXPMKETMJSSI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 206010009944 Colon cancer Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- FRNGIUXKDJKDSJ-UHFFFAOYSA-N o-[2-(dimethylamino)ethyl]hydroxylamine;hydrochloride Chemical compound Cl.CN(C)CCON FRNGIUXKDJKDSJ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WRDPKTWOJAESII-KGYDJYTLSA-N (10Z)-2,3-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-ol hydrochloride Chemical compound Cl.C1=C(O)C=C2C(C(=N\OCC#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 WRDPKTWOJAESII-KGYDJYTLSA-N 0.000 description 2
- SDRGVHRTRWKQQA-FSKGQQLBSA-N (nz)-n-[2,3-dimethoxy-5-methyl-8-(2-piperidin-1-ylethoxy)indeno[1,2-b]indol-10-ylidene]hydroxylamine;hydrochloride Chemical compound Cl.C1=2C=C(OC)C(OC)=CC=2\C(=N\O)C(C2=C3)=C1N(C)C2=CC=C3OCCN1CCCCC1 SDRGVHRTRWKQQA-FSKGQQLBSA-N 0.000 description 2
- XKNPLBJNKGTMIY-LNVKXUELSA-N (z)-2,3,8-trimethoxy-5-methyl-n-prop-2-ynoxyindeno[1,2-b]indol-10-imine Chemical compound C12=CC(OC)=C(OC)C=C2\C(=N\OCC#C)C2=C1N(C)C1=CC=C(OC)C=C12 XKNPLBJNKGTMIY-LNVKXUELSA-N 0.000 description 2
- ZYGLYAZYIZBURJ-VZXGSGAOSA-N 2-[(Z)-(2,3-dimethoxy-5H-indeno[1,2-b]indol-10-ylidene)amino]oxy-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=CC=C2C(C(=N\OCCN(C)C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 ZYGLYAZYIZBURJ-VZXGSGAOSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 2
- FJPMLTZXTKBVKX-UHFFFAOYSA-N 4,6-Dimethoxy-phthalide Chemical compound COC1=CC(OC)=CC2=C1COC2=O FJPMLTZXTKBVKX-UHFFFAOYSA-N 0.000 description 2
- ABFJCCZUMNBAAI-UHFFFAOYSA-N 4,7-dimethoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C(OC)C2=C1COC2=O ABFJCCZUMNBAAI-UHFFFAOYSA-N 0.000 description 2
- ODHPXVGFARBBSK-UHFFFAOYSA-N 5,7-dimethoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC(OC)=CC2=C1C(=O)OC2 ODHPXVGFARBBSK-UHFFFAOYSA-N 0.000 description 2
- BNTDDWPHSMILHQ-UHFFFAOYSA-N 5-methoxy-2-nitrobenzaldehyde Chemical compound COC1=CC=C([N+]([O-])=O)C(C=O)=C1 BNTDDWPHSMILHQ-UHFFFAOYSA-N 0.000 description 2
- JEGVXFVQGOOSLC-PLUDUZGDSA-N Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JEGVXFVQGOOSLC-PLUDUZGDSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- HDPKLKMNNDGHLC-UHFFFAOYSA-N o-(1-cyclopropylprop-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C1CC1 HDPKLKMNNDGHLC-UHFFFAOYSA-N 0.000 description 2
- XLFJVRPMJOHGLH-UHFFFAOYSA-N o-(1-phenylbut-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.CC#CC(ON)C1=CC=CC=C1 XLFJVRPMJOHGLH-UHFFFAOYSA-N 0.000 description 2
- GDPFLEFIPBINCB-UHFFFAOYSA-N o-(1-thiophen-2-ylprop-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C1=CC=CS1 GDPFLEFIPBINCB-UHFFFAOYSA-N 0.000 description 2
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material 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
- 239000003826 tablet Substances 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OLGIFSIEAFKIGJ-KGYDJYTLSA-N (10E)-1,3-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-ol hydrochloride Chemical compound Cl.N1C2=CC=C(O)C=C2C\2=C1C(C=C(C=C1OC)OC)=C1C/2=N/OCC#C OLGIFSIEAFKIGJ-KGYDJYTLSA-N 0.000 description 1
- RFCPCFFUPJZVEB-LSDHQDQOSA-N (10E)-1,4-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-ol Chemical compound N1C2=CC=C(O)C=C2C\2=C1C(C(OC)=CC=C1OC)=C1C/2=N/OCC#C RFCPCFFUPJZVEB-LSDHQDQOSA-N 0.000 description 1
- GCRLCNYWVHYVMS-QOCHGBHMSA-N (10Z)-2,4-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-ol Chemical compound C1=C(O)C=C2C(C(=N\OCC#C)/C=3C=C(C=C(OC)C=33)OC)=C3NC2=C1 GCRLCNYWVHYVMS-QOCHGBHMSA-N 0.000 description 1
- ABZKNVCKNIUXSR-SGEDCAFJSA-N (10z)-2,3-dimethoxy-5-methyl-10-(1-phenylprop-2-ynoxyimino)indeno[1,2-b]indol-8-ol Chemical compound CN1C2=CC=C(O)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C#C)C1=CC=CC=C1 ABZKNVCKNIUXSR-SGEDCAFJSA-N 0.000 description 1
- FQHCPFMTXFJZJS-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine;hydrochloride Chemical compound Cl.COC1=CC=C(NN)C=C1 FQHCPFMTXFJZJS-UHFFFAOYSA-N 0.000 description 1
- AIFAWXWFXVGQRW-UHFFFAOYSA-M (5,6-dimethoxy-3-oxo-1h-2-benzofuran-1-yl)-triphenylphosphanium;bromide Chemical compound [Br-].O1C(=O)C=2C=C(OC)C(OC)=CC=2C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AIFAWXWFXVGQRW-UHFFFAOYSA-M 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OTZXKUICIHQPQD-VZXGSGAOSA-N (NZ)-N-[8-[2-(dimethylamino)ethoxy]-2,3-dimethoxy-5H-indeno[1,2-b]indol-10-ylidene]hydroxylamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\O)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 OTZXKUICIHQPQD-VZXGSGAOSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- LNZYHIITQXDLFY-OHYPFYFLSA-N (Z)-2,3,8-trimethoxy-N-(1-phenylprop-2-ynoxy)-5H-indeno[1,2-b]indol-10-imine Chemical compound C1=2C3=CC(OC)=CC=C3NC=2C2=CC(OC)=C(OC)C=C2\C1=N\OC(C#C)C1=CC=CC=C1 LNZYHIITQXDLFY-OHYPFYFLSA-N 0.000 description 1
- FKHPMQJSEAEJNL-LNVKXUELSA-N (Z)-2,3,8-trimethoxy-N-prop-2-ynoxy-5H-indeno[1,2-b]indol-10-imine Chemical compound C12=CC(OC)=C(OC)C=C2\C(=N\OCC#C)C2=C1NC1=CC=C(OC)C=C12 FKHPMQJSEAEJNL-LNVKXUELSA-N 0.000 description 1
- LGCCPEUIBZORGR-WCTVFOPTSA-N (Z)-2,3-dimethoxy-N-[(2-methylpropan-2-yl)oxy]-8-(2-pyrrolidin-1-ylethoxy)-5H-indeno[1,2-b]indol-10-imine Chemical compound C1=2C=C(OC)C(OC)=CC=2\C(=N\OC(C)(C)C)C(C2=C3)=C1NC2=CC=C3OCCN1CCCC1 LGCCPEUIBZORGR-WCTVFOPTSA-N 0.000 description 1
- PLJSFLAPGQRMCU-OHYPFYFLSA-N (z)-2,3,8-trimethoxy-5-methyl-n-(1-phenylprop-2-ynoxy)indeno[1,2-b]indol-10-imine Chemical compound C1=2C3=CC(OC)=CC=C3N(C)C=2C2=CC(OC)=C(OC)C=C2\C1=N\OC(C#C)C1=CC=CC=C1 PLJSFLAPGQRMCU-OHYPFYFLSA-N 0.000 description 1
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 1
- VZWIQRAVCKIZRS-UHFFFAOYSA-N 1-chloro-1-ethynylcyclopentane Chemical compound C#CC1(Cl)CCCC1 VZWIQRAVCKIZRS-UHFFFAOYSA-N 0.000 description 1
- KHVHHKNFFYUOMU-UHFFFAOYSA-N 2,3-dimethoxy-5-methyl-8-(2-piperidin-1-ylethoxy)indeno[1,2-b]indol-10-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(=O)C(C2=C3)=C1N(C)C2=CC=C3OCCN1CCCCC1 KHVHHKNFFYUOMU-UHFFFAOYSA-N 0.000 description 1
- NYRREOIMJTVMCI-UHFFFAOYSA-N 2,3-dimethoxy-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 NYRREOIMJTVMCI-UHFFFAOYSA-N 0.000 description 1
- IOPFUSMCYUKKEA-UHFFFAOYSA-N 2,3-dimethoxy-8-(2-piperidin-1-ylethoxy)-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.C1=2C=C(OC)C(OC)=CC=2C(=O)C(C2=C3)=C1NC2=CC=C3OCCN1CCCCC1 IOPFUSMCYUKKEA-UHFFFAOYSA-N 0.000 description 1
- MCGRHMJQSBGSLL-UHFFFAOYSA-N 2,3-dimethoxy-8-(2-pyrrolidin-1-ylethoxy)-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.C1=2C=C(OC)C(OC)=CC=2C(=O)C(C2=C3)=C1NC2=CC=C3OCCN1CCCC1 MCGRHMJQSBGSLL-UHFFFAOYSA-N 0.000 description 1
- RSPHLCUQBXWJQM-NYIQPMNJSA-N 2-[(Z)-[8-[2-(dimethylamino)ethoxy]-2,3-dimethoxy-5H-indeno[1,2-b]indol-10-ylidene]amino]oxyacetonitrile hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OCC#N)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 RSPHLCUQBXWJQM-NYIQPMNJSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- OAMYVWWCBVRFMV-FSKGQQLBSA-N 2-[[(10E)-1,3-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C\2=C1C(C=C(C=C1OC)OC)=C1C/2=N/OCC#C OAMYVWWCBVRFMV-FSKGQQLBSA-N 0.000 description 1
- KCVOGQMYVMZTKZ-LIIBIFOCSA-N 2-[[(10E)-1,4-dimethoxy-10-(1-phenylprop-2-ynoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=2C(OC)=CC=C(OC)C=2C=2NC3=CC=C(OCCN(C)C)C=C3C=2\C1=N/OC(C#C)C1=CC=CC=C1 KCVOGQMYVMZTKZ-LIIBIFOCSA-N 0.000 description 1
- ZKMKYPLJOVPKRF-JOTHOCIUSA-N 2-[[(10E)-1,4-dimethoxy-10-phenylmethoxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=2C(OC)=CC=C(OC)C=2C=2NC3=CC=C(OCCN(C)C)C=C3C=2\C1=N/OCC1=CC=CC=C1 ZKMKYPLJOVPKRF-JOTHOCIUSA-N 0.000 description 1
- DKKYYGATPUOYEZ-YCNYHXFESA-N 2-[[(10Z)-10-(1,3-benzodioxol-5-ylmethoxyimino)-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound C1=C(OCCN(C)C)C=C2C(C(=N\OCC=3C=C4OCOC4=CC=3)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 DKKYYGATPUOYEZ-YCNYHXFESA-N 0.000 description 1
- NCELQEYOBFSSMW-NHUYCKTKSA-N 2-[[(10Z)-10-(1-ethynylcyclopentyl)oxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC1(C#C)CCCC1 NCELQEYOBFSSMW-NHUYCKTKSA-N 0.000 description 1
- PEDSCBWITKWKSU-QIXZSFSWSA-N 2-[[(10Z)-10-(3,5-dimethoxyphenoxy)imino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(O\N=C\2C=3C4=CC(OCCN(C)C)=CC=C4NC=3C3=CC(OC)=C(OC)C=C3/2)=C1 PEDSCBWITKWKSU-QIXZSFSWSA-N 0.000 description 1
- OPMFQTGWBYRYAK-SCWNGGFCSA-N 2-[[(10Z)-10-[(2R)-but-3-yn-2-yl]oxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\O[C@H](C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 OPMFQTGWBYRYAK-SCWNGGFCSA-N 0.000 description 1
- RIKKNIVZEUMGOY-OLGSEDKOSA-N 2-[[(10Z)-10-[(2S)-but-3-yn-2-yl]oxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine 2,3-dihydroxybutanedioic acid Chemical compound OC(C(O)C(O)=O)C(O)=O.COc1cc2\C(=N\O[C@@H](C)C#C)c3c([nH]c4ccc(OCCN(C)C)cc34)-c2cc1OC RIKKNIVZEUMGOY-OLGSEDKOSA-N 0.000 description 1
- OPMFQTGWBYRYAK-OLGSEDKOSA-N 2-[[(10Z)-10-[(2S)-but-3-yn-2-yl]oxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\O[C@@H](C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 OPMFQTGWBYRYAK-OLGSEDKOSA-N 0.000 description 1
- GPFSYMCESZFOQG-UBBMEQGGSA-N 2-[[(10Z)-10-[(2S)-but-3-yn-2-yl]oxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.C1=C(OCCN(C)C)C=C2C(C(=N\O[C@@H](C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 GPFSYMCESZFOQG-UBBMEQGGSA-N 0.000 description 1
- OCKVEKWUDWZINS-GCUVURNUSA-N 2-[[(10Z)-10-[(3,5-dimethylphenyl)methoxyimino]-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC(C)=CC(C)=C1 OCKVEKWUDWZINS-GCUVURNUSA-N 0.000 description 1
- CPLQNSZFGQZVMD-GIBMLHLSSA-N 2-[[(10Z)-10-[(4-fluorophenyl)methoxyimino]-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC=C(F)C=C1 CPLQNSZFGQZVMD-GIBMLHLSSA-N 0.000 description 1
- SFSDOHVWGOZPPU-QIRPVNSRSA-N 2-[[(10Z)-10-[1-(furan-3-yl)prop-2-ynoxyimino]-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C#C)C=1C=COC=1 SFSDOHVWGOZPPU-QIRPVNSRSA-N 0.000 description 1
- BPNMJOMUEHEVGK-QVLVYXDLSA-N 2-[[(10Z)-10-[1-(furan-3-yl)prop-2-ynoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=2C3=CC(OCCN(C)C)=CC=C3NC=2C2=CC=CC=C2\C1=N\OC(C#C)C=1C=COC=1 BPNMJOMUEHEVGK-QVLVYXDLSA-N 0.000 description 1
- CLJCJOXDQCIISX-NECWGFRUSA-N 2-[[(10Z)-10-benzhydryloxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)O\N=C/1\C2=CC(=C(C=C2C=2NC=3C=CC(=CC=3C=2\1)OCCN(C)C)OC)OC CLJCJOXDQCIISX-NECWGFRUSA-N 0.000 description 1
- CCOIOFSSIHFRAA-WZRSSYQVSA-N 2-[[(10Z)-10-but-2-ynoxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OCC#CC)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 CCOIOFSSIHFRAA-WZRSSYQVSA-N 0.000 description 1
- AAIQESZVXKKKGL-QFOGJQNBSA-N 2-[[(10Z)-10-but-3-yn-2-yloxyimino-2,3-diethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OC(C)C#C)/C=3C=C(C(=CC=33)OCC)OCC)=C3NC2=C1 AAIQESZVXKKKGL-QFOGJQNBSA-N 0.000 description 1
- OPMFQTGWBYRYAK-WZRSSYQVSA-N 2-[[(10Z)-10-but-3-yn-2-yloxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OC(C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 OPMFQTGWBYRYAK-WZRSSYQVSA-N 0.000 description 1
- QPNUAWJNIKBOCH-ADYMNVQMSA-N 2-[[(10Z)-10-but-3-yn-2-yloxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC=CC=C1/C2=N/OC(C)C#C QPNUAWJNIKBOCH-ADYMNVQMSA-N 0.000 description 1
- MXERGPPJNQHATQ-RFBIWTDZSA-N 2-[[(10Z)-10-but-3-ynoxyimino-2,3-dimethoxy-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound C1=C(OCCN(C)C)C=C2C(C(=N\OCCC#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 MXERGPPJNQHATQ-RFBIWTDZSA-N 0.000 description 1
- VGTBVCZPWWCNTL-FPODKLOTSA-N 2-[[(10Z)-2,3-dimethoxy-10-(1-phenylbut-2-ynoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C#CC)C1=CC=CC=C1 VGTBVCZPWWCNTL-FPODKLOTSA-N 0.000 description 1
- VKQBXEIZBTZRCK-GWLNUVCFSA-N 2-[[(10Z)-2,3-dimethoxy-10-(1-phenylprop-2-ynoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C#C)C1=CC=CC=C1 VKQBXEIZBTZRCK-GWLNUVCFSA-N 0.000 description 1
- HNSRANXPEFITDZ-WLNXZIBISA-N 2-[[(10Z)-2,3-dimethoxy-10-(2-methylbut-3-yn-2-yloxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OC(C)(C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 HNSRANXPEFITDZ-WLNXZIBISA-N 0.000 description 1
- SVMXAMLFASTGCU-DJUUNRNFSA-N 2-[[(10Z)-2,3-dimethoxy-10-(3-methylpent-1-yn-3-yloxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC(OC)=C(OC)C=C1/C2=N/OC(C)(CC)C#C SVMXAMLFASTGCU-DJUUNRNFSA-N 0.000 description 1
- RHVSKUVVOLXFKE-GCUVURNUSA-N 2-[[(10Z)-2,3-dimethoxy-10-(3-phenylprop-2-ynoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC#CC1=CC=CC=C1 RHVSKUVVOLXFKE-GCUVURNUSA-N 0.000 description 1
- MYDDZWCDVGWPIK-QFOGJQNBSA-N 2-[[(10Z)-2,3-dimethoxy-10-(4-methylpent-1-yn-3-yloxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OC(C#C)C(C)C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 MYDDZWCDVGWPIK-QFOGJQNBSA-N 0.000 description 1
- VOUZFOFSPZCZOG-QIRPVNSRSA-N 2-[[(10Z)-2,3-dimethoxy-10-(4-methylphenoxy)imino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC1=CC=C(C)C=C1 VOUZFOFSPZCZOG-QIRPVNSRSA-N 0.000 description 1
- CPVDMVOZIQVCGJ-QIRPVNSRSA-N 2-[[(10Z)-2,3-dimethoxy-10-(5-methylhex-1-yn-3-yloxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OC(CC(C)C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 CPVDMVOZIQVCGJ-QIRPVNSRSA-N 0.000 description 1
- JKXVTYRKQVEVCI-YJKCNMNRSA-N 2-[[(10Z)-2,3-dimethoxy-10-(naphthalen-1-ylmethoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound C1=C(OCCN(C)C)C=C2C(C(=N\OCC=3C4=CC=CC=C4C=CC=3)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 JKXVTYRKQVEVCI-YJKCNMNRSA-N 0.000 description 1
- SNDJRYBHLRYOAH-NHUYCKTKSA-N 2-[[(10Z)-2,3-dimethoxy-10-(pyridin-2-ylmethoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC=CC=N1 SNDJRYBHLRYOAH-NHUYCKTKSA-N 0.000 description 1
- PRWRPAYDJWZXGX-SGEDCAFJSA-N 2-[[(10Z)-2,3-dimethoxy-10-(thiophen-2-ylmethoxyimino)-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC=CS1 PRWRPAYDJWZXGX-SGEDCAFJSA-N 0.000 description 1
- VKQBXEIZBTZRCK-JPPYSEFESA-N 2-[[(10Z)-2,3-dimethoxy-10-[(1S)-1-phenylprop-2-ynoxy]imino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1([C@H](C#C)O/N=C2/C=3C=C(C(=CC=3C3=C2C2=CC(OCCN(C)C)=CC=C2N3)OC)OC)=CC=CC=C1 VKQBXEIZBTZRCK-JPPYSEFESA-N 0.000 description 1
- XMQVKOFLZXVUCU-MEIHLTSWSA-N 2-[[(10Z)-2,3-dimethoxy-10-[(3,4,5-trimethoxyphenyl)methoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC(OC)=C(OC)C(OC)=C1 XMQVKOFLZXVUCU-MEIHLTSWSA-N 0.000 description 1
- QJLXLKUAUHGKGF-VGYQCLJVSA-N 2-[[(10Z)-2,3-dimethoxy-10-[(3R)-oct-1-yn-3-yl]oxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC(OC)=C(OC)C=C1/C2=N/O[C@H](CCCCC)C#C QJLXLKUAUHGKGF-VGYQCLJVSA-N 0.000 description 1
- QJLXLKUAUHGKGF-XJJUMWIZSA-N 2-[[(10Z)-2,3-dimethoxy-10-[(3S)-oct-1-yn-3-yl]oxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC(OC)=C(OC)C=C1/C2=N/O[C@@H](CCCCC)C#C QJLXLKUAUHGKGF-XJJUMWIZSA-N 0.000 description 1
- YTQOJJFMBQOBHR-YCNYHXFESA-N 2-[[(10Z)-2,3-dimethoxy-10-[(4-methoxyphenyl)methoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound C1=CC(OC)=CC=C1CO\N=C\1C(C2=CC(OCCN(C)C)=CC=C2N2)=C2C2=CC(OC)=C(OC)C=C2/1 YTQOJJFMBQOBHR-YCNYHXFESA-N 0.000 description 1
- IEJQNYCDVRIRIA-HYOGKJQXSA-N 2-[[(10Z)-2,3-dimethoxy-10-[(4-nitrophenyl)methoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC=C([N+]([O-])=O)C=C1 IEJQNYCDVRIRIA-HYOGKJQXSA-N 0.000 description 1
- JYDFYFDIJLHRLQ-ZSWXBHCYSA-N 2-[[(10Z)-2,3-dimethoxy-10-[(4-phenoxyphenyl)methoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC(C=C1)=CC=C1OC1=CC=CC=C1 JYDFYFDIJLHRLQ-ZSWXBHCYSA-N 0.000 description 1
- CZBALQJWXGUEIQ-OGWVPCEVSA-N 2-[[(10Z)-2,3-dimethoxy-10-[(4-phenylphenyl)methoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC(C=C1)=CC=C1C1=CC=CC=C1 CZBALQJWXGUEIQ-OGWVPCEVSA-N 0.000 description 1
- PLWDRDDLAVYTRX-NFEWNITESA-N 2-[[(10Z)-2,3-dimethoxy-10-[(E)-5-phenylpent-2-en-4-ynoxy]imino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound COc1cc2\C(=N\OC\C=C\C#Cc3ccccc3)c3c([nH]c4ccc(OCCN(C)C)cc34)-c2cc1OC PLWDRDDLAVYTRX-NFEWNITESA-N 0.000 description 1
- VYVQGVWUXDDCBS-YJKCNMNRSA-N 2-[[(10Z)-2,3-dimethoxy-10-[1-(4-methoxyphenyl)but-3-enoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound C1=CC(OC)=CC=C1C(CC=C)O\N=C\1C(C2=CC(OCCN(C)C)=CC=C2N2)=C2C2=CC(OC)=C(OC)C=C2/1 VYVQGVWUXDDCBS-YJKCNMNRSA-N 0.000 description 1
- GZSGABHNMQJUCM-FPODKLOTSA-N 2-[[(10Z)-2,3-dimethoxy-10-[1-(4-methylphenyl)prop-2-ynoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C#C)C1=CC=C(C)C=C1 GZSGABHNMQJUCM-FPODKLOTSA-N 0.000 description 1
- KMZQSHSABRRGOP-MORHETIJSA-N 2-[[(10Z)-2,3-dimethoxy-10-[[4-[(E)-2-phenylethenyl]phenyl]methoxyimino]-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC(C=C1)=CC=C1\C=C\C1=CC=CC=C1 KMZQSHSABRRGOP-MORHETIJSA-N 0.000 description 1
- AUDUEEPPVNPIRU-WKKHQKTCSA-N 2-[[(10Z)-2,3-dimethoxy-10-methoxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC(OC)=C(OC)C=C1/C2=N/OC AUDUEEPPVNPIRU-WKKHQKTCSA-N 0.000 description 1
- QJLXLKUAUHGKGF-QIXZSFSWSA-N 2-[[(10Z)-2,3-dimethoxy-10-oct-1-yn-3-yloxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC(OC)=C(OC)C=C1/C2=N/OC(CCCCC)C#C QJLXLKUAUHGKGF-QIXZSFSWSA-N 0.000 description 1
- WYUBREQRQJZFLQ-QVLVYXDLSA-N 2-[[(10Z)-2,3-dimethoxy-10-penta-1,4-diyn-3-yloxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OC(C#C)C#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 WYUBREQRQJZFLQ-QVLVYXDLSA-N 0.000 description 1
- NMZNYIGLOBVWFU-OHYPFYFLSA-N 2-[[(10Z)-2,3-dimethoxy-10-phenoxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC1=CC=CC=C1 NMZNYIGLOBVWFU-OHYPFYFLSA-N 0.000 description 1
- BINCJJQQLZUHNN-HYOGKJQXSA-N 2-[[(10Z)-2,3-dimethoxy-10-phenylmethoxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine Chemical compound N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OCC1=CC=CC=C1 BINCJJQQLZUHNN-HYOGKJQXSA-N 0.000 description 1
- SLJVKQGABMIOEM-FSKGQQLBSA-N 2-[[(10Z)-2,3-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=N\OCC#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 SLJVKQGABMIOEM-FSKGQQLBSA-N 0.000 description 1
- CRJFDXQOAUUWQE-QIRPVNSRSA-N 2-[[(11Z)-11-[1-(furan-3-yl)prop-2-ynoxyimino]-15,18-dioxa-3-azapentacyclo[10.8.0.02,10.04,9.014,19]icosa-1(20),2(10),4(9),5,7,12,14(19)-heptaen-7-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.C1=2C3=CC(OCCN(C)C)=CC=C3NC=2C2=CC=3OCCOC=3C=C2\C1=N\OC(C#C)C=1C=COC=1 CRJFDXQOAUUWQE-QIRPVNSRSA-N 0.000 description 1
- YVEFKMLLGBYCRK-WZRSSYQVSA-N 2-[[(11Z)-11-but-3-yn-2-yloxyimino-15,18-dioxa-3-azapentacyclo[10.8.0.02,10.04,9.014,19]icosa-1(20),2(10),4(9),5,7,12,14(19)-heptaen-7-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C1=CC(OCCO3)=C3C=C1/C2=N/OC(C)C#C YVEFKMLLGBYCRK-WZRSSYQVSA-N 0.000 description 1
- XAPPBYYNDUPKMW-UHFFFAOYSA-N 2-aminooxyacetonitrile;hydrochloride Chemical compound Cl.NOCC#N XAPPBYYNDUPKMW-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical group CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- SJNVDRMYNJDFHS-UHFFFAOYSA-N 2-nitro-5-(2-piperidin-1-ylethoxy)benzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC=C1OCCN1CCCCC1 SJNVDRMYNJDFHS-UHFFFAOYSA-N 0.000 description 1
- LGQHNVLFBLMLMI-UHFFFAOYSA-N 2-nitro-5-(2-pyrrolidin-1-ylethoxy)benzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC=C1OCCN1CCCC1 LGQHNVLFBLMLMI-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MVMUJCKCZKQGNB-UHFFFAOYSA-N 3,8-dihydro-2h-furo[3,4-g][1,4]benzodioxin-6-one Chemical compound O1CCOC2=C1C=C1COC(=O)C1=C2 MVMUJCKCZKQGNB-UHFFFAOYSA-N 0.000 description 1
- CRNIEXJWYHGTGR-UHFFFAOYSA-N 3-bromo-5,6-dimethoxy-3h-2-benzofuran-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2Br CRNIEXJWYHGTGR-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- VHXTWGRCYCYOGR-UHFFFAOYSA-N 4-(1-aminooxyprop-2-ynyl)benzonitrile;hydrochloride Chemical compound Cl.NOC(C#C)C1=CC=C(C#N)C=C1 VHXTWGRCYCYOGR-UHFFFAOYSA-N 0.000 description 1
- BZZZUJPHNFZWDG-SSKLNZFYSA-N 4-[1-[(Z)-[8-[2-(dimethylamino)ethoxy]-2,3-dimethoxy-5H-indeno[1,2-b]indol-10-ylidene]amino]oxyprop-2-ynyl]benzonitrile hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\OC(C#C)C1=CC=C(C#N)C=C1 BZZZUJPHNFZWDG-SSKLNZFYSA-N 0.000 description 1
- HDJRNMVQLGESEX-UHFFFAOYSA-N 4-chlorothiadiazole Chemical compound ClC1=CSN=N1 HDJRNMVQLGESEX-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- XGSTZLKGNYGAMW-UHFFFAOYSA-N 5,6-diethoxy-3h-2-benzofuran-1-one Chemical compound C1=C(OCC)C(OCC)=CC2=C1C(=O)OC2 XGSTZLKGNYGAMW-UHFFFAOYSA-N 0.000 description 1
- FUNZYPBDGLATMV-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-2-nitrobenzaldehyde Chemical compound CCN(CC)CCOC1=CC=C([N+]([O-])=O)C(C=O)=C1 FUNZYPBDGLATMV-UHFFFAOYSA-N 0.000 description 1
- USLPRYCBDKMZGO-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-2-nitrobenzaldehyde Chemical compound CN(C)CCOC1=CC=C([N+]([O-])=O)C(C=O)=C1 USLPRYCBDKMZGO-UHFFFAOYSA-N 0.000 description 1
- CIONPRVYNFDTHL-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl-methylamino]-2-nitrobenzaldehyde Chemical compound CN(C)CCN(C)C1=CC=C([N+]([O-])=O)C(C=O)=C1 CIONPRVYNFDTHL-UHFFFAOYSA-N 0.000 description 1
- FBXHJIQSXYECCM-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-1,3-dimethoxy-10-(1-phenylprop-2-ynoxyimino)indeno[1,2-b]indol-8-ol Chemical compound COC1=CC(OC)=CC(C2=C3C4=CC(O)=CC=C4N2CCN(C)C)=C1C3=NOC(C#C)C1=CC=CC=C1 FBXHJIQSXYECCM-UHFFFAOYSA-N 0.000 description 1
- ORSSDSSTEISWMM-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-8-hydroxy-1,3-dimethoxyindeno[1,2-b]indol-10-one Chemical compound CN(C)CCN1C2=CC=C(O)C=C2C2=C1C(C=C(C=C1OC)OC)=C1C2=O ORSSDSSTEISWMM-UHFFFAOYSA-N 0.000 description 1
- ONUYTYDJSPRVSW-UHFFFAOYSA-N 5-amino-2-nitrobenzaldehyde Chemical compound NC1=CC=C([N+]([O-])=O)C(C=O)=C1 ONUYTYDJSPRVSW-UHFFFAOYSA-N 0.000 description 1
- QIYDTIMMZOUCGL-UHFFFAOYSA-N 5h-furo[3,4-f][1,3]benzodioxol-7-one Chemical compound C1=C2C(=O)OCC2=CC2=C1OCO2 QIYDTIMMZOUCGL-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- FEMVJRNUEUCDBA-UHFFFAOYSA-N 8-[2-(dimethylamino)ethoxy]-1,4-dimethoxy-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C(C(OC)=CC=C1OC)=C1C2=O FEMVJRNUEUCDBA-UHFFFAOYSA-N 0.000 description 1
- XTQLJSVJCKXGPD-UHFFFAOYSA-N 8-[2-(dimethylamino)ethoxy]-2,3-diethoxy-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.C1=C(OCCN(C)C)C=C2C(C(=O)C=3C=C(C(=CC=33)OCC)OCC)=C3NC2=C1 XTQLJSVJCKXGPD-UHFFFAOYSA-N 0.000 description 1
- ICNUAWWNUIGZBP-UHFFFAOYSA-N 8-[2-(dimethylamino)ethoxy]-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(=O)C2=C1NC1=CC=C(OCCN(C)C)C=C12 ICNUAWWNUIGZBP-UHFFFAOYSA-N 0.000 description 1
- FGAGRGRSELCXHQ-UHFFFAOYSA-N 8-hydroxy-1,3-dimethoxy-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.N1C2=CC=C(O)C=C2C2=C1C(C=C(C=C1OC)OC)=C1C2=O FGAGRGRSELCXHQ-UHFFFAOYSA-N 0.000 description 1
- XMKLYZWXUVIWDB-UHFFFAOYSA-N 8-hydroxy-2,3-dimethoxy-5h-indeno[1,2-b]indol-10-one;hydrochloride Chemical compound Cl.C1=C(O)C=C2C(C(=O)C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 XMKLYZWXUVIWDB-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- TVFJOQRKRONAMZ-LNVKXUELSA-N C(CC#C)O\N=C/1\C2=CC(=C(C=C2C=2N(C=3C=CC=CC3C21)C)OC)OC Chemical compound C(CC#C)O\N=C/1\C2=CC(=C(C=C2C=2N(C=3C=CC=CC3C21)C)OC)OC TVFJOQRKRONAMZ-LNVKXUELSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- DXOLOIOZDPFDSV-UHFFFAOYSA-N Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1C2=NOC(C#C)C1=CC=C(F)C=C1 Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1C2=NOC(C#C)C1=CC=C(F)C=C1 DXOLOIOZDPFDSV-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZRIDZNVFZPGCGB-XONOVKDISA-N N'-[(10Z)-2,3-dimethoxy-10-prop-2-ynoxyimino-5H-indeno[1,2-b]indol-8-yl]-N,N,N'-trimethylethane-1,2-diamine dihydrochloride Chemical compound Cl.Cl.C1=C(N(C)CCN(C)C)C=C2C(C(=N\OCC#C)/C=3C=C(C(=CC=33)OC)OC)=C3NC2=C1 ZRIDZNVFZPGCGB-XONOVKDISA-N 0.000 description 1
- KAZWEEFWNCUSAK-PYMCRZDISA-N N,N-dimethyl-2-[(Z)-(2,3,8-trimethoxy-5H-indeno[1,2-b]indol-10-ylidene)amino]oxyethanamine dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2\C(=N\OCCN(C)C)C2=C1NC1=CC=C(OC)C=C12 KAZWEEFWNCUSAK-PYMCRZDISA-N 0.000 description 1
- HFGNIWZHPBPULV-ADYMNVQMSA-N N,N-dimethyl-2-[[(11Z)-11-prop-2-ynoxyimino-5,7-dioxa-19-azapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-1(12),2,4(8),9,13(18),14,16-heptaen-15-yl]oxy]ethanamine hydrochloride Chemical compound Cl.C12=CC=3OCOC=3C=C2\C(=N\OCC#C)C2=C1NC1=CC=C(OCCN(C)C)C=C12 HFGNIWZHPBPULV-ADYMNVQMSA-N 0.000 description 1
- AQBWSEZWAVBMGR-GIBMLHLSSA-N N-[(Z)-[8-[2-(dimethylamino)ethoxy]-2,3-dimethoxy-5H-indeno[1,2-b]indol-10-ylidene]amino]-4-methoxyaniline hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N\N=C\1C(C2=CC(OCCN(C)C)=CC=C2N2)=C2C2=CC(OC)=C(OC)C=C2/1 AQBWSEZWAVBMGR-GIBMLHLSSA-N 0.000 description 1
- JSWXJZUVAXCNIC-NHUYCKTKSA-N N-[(Z)-[8-[2-(dimethylamino)ethoxy]-2,3-dimethoxy-5H-indeno[1,2-b]indol-10-ylidene]amino]aniline hydrochloride Chemical compound Cl.N1C2=CC=C(OCCN(C)C)C=C2C2=C1C=1C=C(OC)C(OC)=CC=1\C2=N\NC1=CC=CC=C1 JSWXJZUVAXCNIC-NHUYCKTKSA-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
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000011970 concomitant therapy Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 238000000684 flow cytometry Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule 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
- 239000001963 growth medium Substances 0.000 description 1
- DHEZQYZJFCIQQA-UHFFFAOYSA-N hydron;o-[(4-methoxyphenyl)methyl]hydroxylamine;chloride Chemical compound Cl.COC1=CC=C(CON)C=C1 DHEZQYZJFCIQQA-UHFFFAOYSA-N 0.000 description 1
- LKCAFSOYOMFQSL-UHFFFAOYSA-N hydron;o-[(4-nitrophenyl)methyl]hydroxylamine;chloride Chemical compound Cl.NOCC1=CC=C([N+]([O-])=O)C=C1 LKCAFSOYOMFQSL-UHFFFAOYSA-N 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical class C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- SRQVQLMWUIADDC-UHFFFAOYSA-N o-(1,3-benzodioxol-5-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=C2OCOC2=C1 SRQVQLMWUIADDC-UHFFFAOYSA-N 0.000 description 1
- UZOAJSRELVPONZ-UHFFFAOYSA-N o-(1-phenylbut-3-enyl)hydroxylamine;hydrochloride Chemical compound Cl.C=CCC(ON)C1=CC=CC=C1 UZOAJSRELVPONZ-UHFFFAOYSA-N 0.000 description 1
- KIXXEHQNJVYEIJ-UHFFFAOYSA-N o-(1-phenylhexa-1,4-diyn-3-yl)hydroxylamine;hydrochloride Chemical compound Cl.CC#CC(ON)C#CC1=CC=CC=C1 KIXXEHQNJVYEIJ-UHFFFAOYSA-N 0.000 description 1
- QAVLDRVQPLDPCZ-UHFFFAOYSA-N o-(1-pyridin-3-ylprop-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C1=CC=CN=C1 QAVLDRVQPLDPCZ-UHFFFAOYSA-N 0.000 description 1
- JHCRNARYVLGMON-UHFFFAOYSA-N o-(1-thiophen-3-ylprop-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C=1C=CSC=1 JHCRNARYVLGMON-UHFFFAOYSA-N 0.000 description 1
- STTQFJGUKMUBFH-UHFFFAOYSA-N o-(3,5-dimethoxyphenyl)hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(ON)=C1 STTQFJGUKMUBFH-UHFFFAOYSA-N 0.000 description 1
- AGASWYKEXLOTGY-UHFFFAOYSA-N o-(3-phenylprop-2-ynyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC#CC1=CC=CC=C1 AGASWYKEXLOTGY-UHFFFAOYSA-N 0.000 description 1
- AUOJYSFSYBIZKH-UHFFFAOYSA-N o-(4-methylpent-1-yn-3-yl)hydroxylamine;hydrochloride Chemical compound Cl.CC(C)C(ON)C#C AUOJYSFSYBIZKH-UHFFFAOYSA-N 0.000 description 1
- MUDUEUZSAGAOBK-UHFFFAOYSA-N o-(4-methylphenyl)hydroxylamine;hydrochloride Chemical compound Cl.CC1=CC=C(ON)C=C1 MUDUEUZSAGAOBK-UHFFFAOYSA-N 0.000 description 1
- PRTMTMPPGQACCX-UHFFFAOYSA-N o-(5-methylhex-1-yn-3-yl)hydroxylamine;hydrochloride Chemical compound Cl.CC(C)CC(ON)C#C PRTMTMPPGQACCX-UHFFFAOYSA-N 0.000 description 1
- RUGDBRVEODTQSD-UHFFFAOYSA-N o-(naphthalen-1-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.C1=CC=C2C(CON)=CC=CC2=C1 RUGDBRVEODTQSD-UHFFFAOYSA-N 0.000 description 1
- PMPPBLLDPIXDRE-UHFFFAOYSA-N o-(pyridin-2-ylmethyl)hydroxylamine Chemical class NOCC1=CC=CC=N1 PMPPBLLDPIXDRE-UHFFFAOYSA-N 0.000 description 1
- HHQRMKABZGABRY-UHFFFAOYSA-N o-(thiophen-2-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=CS1 HHQRMKABZGABRY-UHFFFAOYSA-N 0.000 description 1
- PHICPCOXDOICNG-RRABGKBLSA-N o-[(1e)-1-phenylhexa-1,5-dien-3-yl]hydroxylamine;hydrochloride Chemical compound Cl.C=CCC(ON)\C=C\C1=CC=CC=C1 PHICPCOXDOICNG-RRABGKBLSA-N 0.000 description 1
- LJKJXQLWGBIHIU-FVGYRXGTSA-N o-[(1s)-1-phenylprop-2-ynyl]hydroxylamine;hydrochloride Chemical compound Cl.NO[C@@H](C#C)C1=CC=CC=C1 LJKJXQLWGBIHIU-FVGYRXGTSA-N 0.000 description 1
- NRXXPMKETMJSSI-WCCKRBBISA-N o-[(2s)-but-3-yn-2-yl]hydroxylamine;hydrochloride Chemical compound Cl.NO[C@@H](C)C#C NRXXPMKETMJSSI-WCCKRBBISA-N 0.000 description 1
- WDIYOALRWSMTRN-UHFFFAOYSA-N o-[(3,4,5-trimethoxyphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC(CON)=CC(OC)=C1OC WDIYOALRWSMTRN-UHFFFAOYSA-N 0.000 description 1
- QMDOJLTWDMPNPQ-UHFFFAOYSA-N o-[(3,5-dimethylphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.CC1=CC(C)=CC(CON)=C1 QMDOJLTWDMPNPQ-UHFFFAOYSA-N 0.000 description 1
- NZRRAPGOFAFOHD-DDWIOCJRSA-N o-[(3s)-oct-1-yn-3-yl]hydroxylamine;hydrochloride Chemical compound Cl.CCCCC[C@H](ON)C#C NZRRAPGOFAFOHD-DDWIOCJRSA-N 0.000 description 1
- UQUFXQSAVIBISI-UHFFFAOYSA-N o-[(4-chlorothiadiazol-5-yl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.NOCC=1SN=NC=1Cl UQUFXQSAVIBISI-UHFFFAOYSA-N 0.000 description 1
- YZNDOVGYWWHJBB-UHFFFAOYSA-N o-[(4-fluorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=C(F)C=C1 YZNDOVGYWWHJBB-UHFFFAOYSA-N 0.000 description 1
- OHLAMDIJRIHQQH-UHFFFAOYSA-N o-[(4-phenoxyphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.C1=CC(CON)=CC=C1OC1=CC=CC=C1 OHLAMDIJRIHQQH-UHFFFAOYSA-N 0.000 description 1
- DSBWIXKKLSGJFJ-UHFFFAOYSA-N o-[(4-phenylphenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.C1=CC(CON)=CC=C1C1=CC=CC=C1 DSBWIXKKLSGJFJ-UHFFFAOYSA-N 0.000 description 1
- GYTXCPCWZUISRG-LKZNWTOYSA-N o-[(e)-5-phenylpent-2-en-4-ynyl]hydroxylamine;hydrochloride Chemical compound Cl.NOC\C=C\C#CC1=CC=CC=C1 GYTXCPCWZUISRG-LKZNWTOYSA-N 0.000 description 1
- XZNJHYWXUCCQBV-UHFFFAOYSA-N o-[1-(4-fluorophenyl)prop-2-ynyl]hydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C1=CC=C(F)C=C1 XZNJHYWXUCCQBV-UHFFFAOYSA-N 0.000 description 1
- VLDIMDNXXSWRIC-UHFFFAOYSA-N o-[1-(4-methoxyphenyl)but-3-enyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC=C(C(CC=C)ON)C=C1 VLDIMDNXXSWRIC-UHFFFAOYSA-N 0.000 description 1
- KBWBXOYQJJQBMK-UHFFFAOYSA-N o-[1-(4-methylphenyl)prop-2-ynyl]hydroxylamine;hydrochloride Chemical compound Cl.CC1=CC=C(C(ON)C#C)C=C1 KBWBXOYQJJQBMK-UHFFFAOYSA-N 0.000 description 1
- UPUKXGDHNAVCRA-UHFFFAOYSA-N o-[3-(4-methoxyphenyl)prop-2-ynyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC=C(C#CCON)C=C1 UPUKXGDHNAVCRA-UHFFFAOYSA-N 0.000 description 1
- SSSSINDKBMJSEV-UHDJGPCESA-N o-[[4-[(e)-2-phenylethenyl]phenyl]methyl]hydroxylamine;hydrochloride Chemical compound Cl.C1=CC(CON)=CC=C1\C=C\C1=CC=CC=C1 SSSSINDKBMJSEV-UHDJGPCESA-N 0.000 description 1
- JCKSWNFJWVXHBU-UHFFFAOYSA-N o-[bis(4-fluorophenyl)methyl]hydroxylamine;hydrochloride Chemical compound Cl.C=1C=C(F)C=CC=1C(ON)C1=CC=C(F)C=C1 JCKSWNFJWVXHBU-UHFFFAOYSA-N 0.000 description 1
- XEAXGNOKDYLPHD-UHFFFAOYSA-N o-benzhydrylhydroxylamine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(ON)C1=CC=CC=C1 XEAXGNOKDYLPHD-UHFFFAOYSA-N 0.000 description 1
- GVWGKAHAWPUVFM-UHFFFAOYSA-N o-but-2-ynylhydroxylamine;hydrochloride Chemical compound Cl.CC#CCON GVWGKAHAWPUVFM-UHFFFAOYSA-N 0.000 description 1
- HAMXDHAZNVTEDN-UHFFFAOYSA-N o-but-3-ynylhydroxylamine;hydrochloride Chemical compound Cl.NOCCC#C HAMXDHAZNVTEDN-UHFFFAOYSA-N 0.000 description 1
- TXSFSGZYQWSOEX-UHFFFAOYSA-N o-butan-2-ylhydroxylamine;hydrochloride Chemical compound Cl.CCC(C)ON TXSFSGZYQWSOEX-UHFFFAOYSA-N 0.000 description 1
- NZRRAPGOFAFOHD-UHFFFAOYSA-N o-oct-1-yn-3-ylhydroxylamine;hydrochloride Chemical compound Cl.CCCCCC(ON)C#C NZRRAPGOFAFOHD-UHFFFAOYSA-N 0.000 description 1
- VFZXTKGYOQIIEK-UHFFFAOYSA-N o-pent-1-yn-3-ylhydroxylamine;hydrochloride Chemical compound Cl.CCC(ON)C#C VFZXTKGYOQIIEK-UHFFFAOYSA-N 0.000 description 1
- YUSMKADHMUVMNC-UHFFFAOYSA-N o-penta-1,4-diyn-3-ylhydroxylamine;hydrochloride Chemical compound Cl.NOC(C#C)C#C YUSMKADHMUVMNC-UHFFFAOYSA-N 0.000 description 1
- DBTXKJJSFWZJNS-UHFFFAOYSA-N o-phenylhydroxylamine;hydrochloride Chemical compound Cl.NOC1=CC=CC=C1 DBTXKJJSFWZJNS-UHFFFAOYSA-N 0.000 description 1
- FOFBPRRSRZLRBW-UHFFFAOYSA-N o-propan-2-ylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)ON FOFBPRRSRZLRBW-UHFFFAOYSA-N 0.000 description 1
- ZBDXGNXNXXPKJI-UHFFFAOYSA-N o-tert-butylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)(C)ON ZBDXGNXNXXPKJI-UHFFFAOYSA-N 0.000 description 1
- IABDFISGZTWKLL-UHFFFAOYSA-N o-tritylhydroxylamine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(ON)C1=CC=CC=C1 IABDFISGZTWKLL-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0107718A FR2826009B1 (fr) | 2001-06-13 | 2001-06-13 | Nouveaux derives d'indenoindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK8342002A3 SK8342002A3 (en) | 2003-01-09 |
| SK286055B6 true SK286055B6 (sk) | 2008-02-05 |
Family
ID=8864253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK834-2002A SK286055B6 (sk) | 2001-06-13 | 2002-06-11 | Indenoindolónové zlúčeniny, spôsob ich prípravy afarmaceutické kompozície s ich obsahom |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6627650B2 (cs) |
| EP (1) | EP1266887B1 (cs) |
| JP (1) | JP3837090B2 (cs) |
| KR (1) | KR100466068B1 (cs) |
| CN (1) | CN1156446C (cs) |
| AR (1) | AR034471A1 (cs) |
| AT (1) | ATE302183T1 (cs) |
| AU (1) | AU781768B2 (cs) |
| BR (1) | BR0202279A (cs) |
| CA (1) | CA2389766C (cs) |
| CZ (1) | CZ20022083A3 (cs) |
| DE (1) | DE60205538T2 (cs) |
| DK (1) | DK1266887T3 (cs) |
| EA (1) | EA004571B1 (cs) |
| ES (1) | ES2247282T3 (cs) |
| FR (1) | FR2826009B1 (cs) |
| HU (1) | HUP0201992A3 (cs) |
| MX (1) | MXPA02005808A (cs) |
| NO (1) | NO322709B1 (cs) |
| NZ (1) | NZ519522A (cs) |
| PL (1) | PL354472A1 (cs) |
| PT (1) | PT1266887E (cs) |
| SI (1) | SI1266887T1 (cs) |
| SK (1) | SK286055B6 (cs) |
| ZA (1) | ZA200204757B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006047231B4 (de) * | 2006-10-04 | 2009-02-12 | Hemmerling, Hans-Jörg, Dr. | Substituierte Indeno[1,2-b]indolderivate als neue Hemmstoffe der Protein Kinase CK2 und ihre Verwendung als Tumor Therapeutika, Cytostatika und Diagnostika |
| EP3147323B2 (de) | 2015-09-28 | 2022-12-28 | Henkel AG & Co. KGaA | Thermisch expandierbare zusammensetzungen mit polysaccharid |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6256471A (ja) * | 1985-09-05 | 1987-03-12 | Teikoku Hormone Mfg Co Ltd | 含窒素四環式化合物 |
| SE8902273D0 (sv) * | 1989-06-22 | 1989-06-22 | Univ Cincinnati | Indenoindole compounds i |
| SE8902274D0 (sv) * | 1989-06-22 | 1989-06-22 | Univ Cincinnati | Indenoidole compounds ii |
| SE9302431D0 (sv) * | 1993-07-16 | 1993-07-16 | Ab Astra | Use of indenoindole compounds |
| US6069153A (en) * | 1998-05-12 | 2000-05-30 | American Home Products Corporation | Indenoindoles and benzocarbazoles as estrogenic agents |
| FR2821843B1 (fr) * | 2001-03-12 | 2003-05-09 | Servier Lab | Nouveaux derives d'isoindoloindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2001
- 2001-06-13 FR FR0107718A patent/FR2826009B1/fr not_active Expired - Fee Related
-
2002
- 2002-06-11 MX MXPA02005808A patent/MXPA02005808A/es active IP Right Grant
- 2002-06-11 SK SK834-2002A patent/SK286055B6/sk not_active IP Right Cessation
- 2002-06-11 AU AU45903/02A patent/AU781768B2/en not_active Ceased
- 2002-06-12 DK DK02291463T patent/DK1266887T3/da active
- 2002-06-12 AR ARP020102206A patent/AR034471A1/es not_active Application Discontinuation
- 2002-06-12 EP EP02291463A patent/EP1266887B1/fr not_active Expired - Lifetime
- 2002-06-12 JP JP2002171000A patent/JP3837090B2/ja not_active Expired - Fee Related
- 2002-06-12 SI SI200230176T patent/SI1266887T1/sl unknown
- 2002-06-12 ES ES02291463T patent/ES2247282T3/es not_active Expired - Lifetime
- 2002-06-12 NZ NZ519522A patent/NZ519522A/en unknown
- 2002-06-12 AT AT02291463T patent/ATE302183T1/de not_active IP Right Cessation
- 2002-06-12 NO NO20022794A patent/NO322709B1/no unknown
- 2002-06-12 PT PT02291463T patent/PT1266887E/pt unknown
- 2002-06-12 DE DE60205538T patent/DE60205538T2/de not_active Expired - Fee Related
- 2002-06-12 KR KR10-2002-0032814A patent/KR100466068B1/ko not_active Expired - Fee Related
- 2002-06-13 ZA ZA200204757A patent/ZA200204757B/xx unknown
- 2002-06-13 EA EA200200563A patent/EA004571B1/ru not_active IP Right Cessation
- 2002-06-13 US US10/171,191 patent/US6627650B2/en not_active Expired - Fee Related
- 2002-06-13 CA CA002389766A patent/CA2389766C/fr not_active Expired - Fee Related
- 2002-06-13 HU HU0201992A patent/HUP0201992A3/hu unknown
- 2002-06-13 BR BR0202279-6A patent/BR0202279A/pt not_active IP Right Cessation
- 2002-06-13 CZ CZ20022083A patent/CZ20022083A3/cs unknown
- 2002-06-13 PL PL02354472A patent/PL354472A1/xx not_active Application Discontinuation
- 2002-06-13 CN CNB021213054A patent/CN1156446C/zh not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2016317521B2 (en) | Novel pyrazolo[3,4-d]pyrimidine compound or salt thereof | |
| KR100256707B1 (ko) | 데아자푸린 유도체; 새로운 부류의 crf1 특이 리간드 | |
| US9828342B2 (en) | Isatin derivatives, pharmaceutical compositions thereof, and methods of use thereof | |
| RU2191176C2 (ru) | Трициклические производные пиразола, фармацевтическая композиция | |
| HU191643B (en) | Process for preparing new n-phenyl-n'-cycloalkyl-alkanoyl-piperazine derivatives | |
| WO2007129111A1 (en) | Diazepine derivatives as 5-ht2a antagonists | |
| EP1799640A2 (en) | Indole compounds useful as serotonin selective agents | |
| NL9002366A (nl) | Nieuwe isoindoolderivaten en zouten daarvan, werkwijze voor de bereiding ervan en antitumorpreparaten die deze derivaten bevatten. | |
| CN116789671A (zh) | 作为Toll样受体激动剂的嘧啶并哒嗪酮类化合物 | |
| CN114149424A (zh) | 用于治疗疾病的杂环化合物 | |
| NZ225808A (en) | Imidazo(1,2-b)pyridazin-2yl carbamate derivatives, preparation thereof, intermediates and pharmaceutical compositions | |
| KR20010015787A (ko) | 테트라히드로피리도피리미디논의 제3 위치 치환 유도체,그의 제조 방법 및 용도 | |
| BG104151A (bg) | 3-ЗАМЕСТЕНИ 3,4,5,7-ТЕТРАХИДРОПИРОЛО [3,4,:4,5] ТИЕНО [2,39г] ПИРИМИДИНОВИ ПРОИЗВОДНИ, ТЯХНОТО ПОЛУЧАВАНЕ И ИЗПОЛЗВАНЕ | |
| JP2909151B2 (ja) | ピリドベンゾインドール、その製造方法及びそれを含有する組成物 | |
| SK286055B6 (sk) | Indenoindolónové zlúčeniny, spôsob ich prípravy afarmaceutické kompozície s ich obsahom | |
| CN103910643B (zh) | 一种抗癌活性甲酮衍生物、合成方法及其用途 | |
| SK175298A3 (en) | Indoline derivatives useful as 5-ht-2c receptor antagonists | |
| WO2015127878A1 (zh) | 稠合吖啶衍生物及其药物组合物、制备方法及应用 | |
| WO2019149128A1 (zh) | 作为抗肿瘤药物的5-氯-2,4-嘧啶衍生物 | |
| FI65244B (fi) | Foerfarande foer framstaellning av 9-(3-(3,5-cis-dimetylpiperazin)propyl)-karbazol anvaendbar saosom ett psykotropiskt medel | |
| CN120112529A (zh) | 一种含吡啶的化合物及其制备方法和用途 | |
| CN116963733A (zh) | 作为enpp1抑制剂的咪唑化合物 | |
| HK1257146B (en) | Novel pyrazolo[3, 4-d] pyrimidine compound or salt thereof | |
| CZ20001436A3 (cs) | Disubstituované deriváty 1,2-benzisotiazolu a jejich použití | |
| NZ621325B2 (en) | Cyclopropaneamine compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20090611 |