AU2007235751A1 - Substituted ring fused azines and their use in cancer therapy - Google Patents
Substituted ring fused azines and their use in cancer therapy Download PDFInfo
- Publication number
- AU2007235751A1 AU2007235751A1 AU2007235751A AU2007235751A AU2007235751A1 AU 2007235751 A1 AU2007235751 A1 AU 2007235751A1 AU 2007235751 A AU2007235751 A AU 2007235751A AU 2007235751 A AU2007235751 A AU 2007235751A AU 2007235751 A1 AU2007235751 A1 AU 2007235751A1
- Authority
- AU
- Australia
- Prior art keywords
- benzofuran
- dimethyl
- propanediamine
- quinazolinyl
- dihydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000011275 oncology therapy Methods 0.000 title claims description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 90
- -1 amino, hydroxyl Chemical group 0.000 claims description 87
- 239000000203 mixture Substances 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 56
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 56
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 53
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 52
- 210000004027 cell Anatomy 0.000 claims description 49
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 48
- 150000002148 esters Chemical class 0.000 claims description 44
- 206010028980 Neoplasm Diseases 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 32
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 31
- LMPHUKMENQIOSG-UHFFFAOYSA-N 3-N-methylbutane-1,3-diamine dihydrochloride Chemical compound Cl.Cl.CNC(C)CCN LMPHUKMENQIOSG-UHFFFAOYSA-N 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- JTYYWQRSEPVEHP-UHFFFAOYSA-N 3-n-methylbutane-1,3-diamine Chemical compound CNC(C)CCN JTYYWQRSEPVEHP-UHFFFAOYSA-N 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- BIDXGEXQRVWXMY-UHFFFAOYSA-N 1-azaniumylpropylazanium;dichloride Chemical compound Cl.Cl.CCC(N)N BIDXGEXQRVWXMY-UHFFFAOYSA-N 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 claims description 11
- 235000001014 amino acid Nutrition 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 238000002560 therapeutic procedure Methods 0.000 claims description 10
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 claims description 8
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 230000032823 cell division Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 229940127089 cytotoxic agent Drugs 0.000 claims description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- WNKYLTAYEAJWOI-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C=3NC(C4=CC=CC=C4N=3)=O)=CC2=C1 WNKYLTAYEAJWOI-UHFFFAOYSA-N 0.000 claims description 4
- FMICMUUWMQZMNB-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7-(trifluoromethyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4)C(F)(F)F)=CC2=C1 FMICMUUWMQZMNB-UHFFFAOYSA-N 0.000 claims description 4
- SOYNRQYJZDGFTK-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-n-(3-morpholin-4-ylpropyl)quinazolin-4-amine;dihydrochloride Chemical compound Cl.Cl.N=1C(C=2OC3=CC=CC=C3C=2)=NC2=CC=CC=C2C=1NCCCN1CCOCC1 SOYNRQYJZDGFTK-UHFFFAOYSA-N 0.000 claims description 4
- 108020004414 DNA Proteins 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
- 241000347391 Umbrina cirrosa Species 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000003556 assay Methods 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 210000004881 tumor cell Anatomy 0.000 claims description 4
- IUXJODWSMBJAMQ-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-benzo[g]quinazolin-4-one Chemical compound C1=CC=C2OC(C=3NC(C4=CC5=CC=CC=C5C=C4N=3)=O)=CC2=C1 IUXJODWSMBJAMQ-UHFFFAOYSA-N 0.000 claims description 3
- PDZBBMVDQPETHG-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-[3-(dimethylamino)propylamino]quinazoline-7-carbonitrile Chemical compound C1=CC=C2OC(C=3N=C(C4=CC=C(C=C4N=3)C#N)NCCCN(C)C)=CC2=C1 PDZBBMVDQPETHG-UHFFFAOYSA-N 0.000 claims description 3
- PDVPJSCNFLKENT-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-oxo-1h-quinazoline-6-carboxamide Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)C(=O)N)=CC2=C1 PDVPJSCNFLKENT-UHFFFAOYSA-N 0.000 claims description 3
- VXYABLYQCMPUIA-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-oxo-1h-quinazoline-8-carboxamide Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4C(=O)N)=CC2=C1 VXYABLYQCMPUIA-UHFFFAOYSA-N 0.000 claims description 3
- DUVMPUHFGZXNKW-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-5-nitro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C=CC=C(C=4C(=O)N3)[N+](=O)[O-])=CC2=C1 DUVMPUHFGZXNKW-UHFFFAOYSA-N 0.000 claims description 3
- UHZOGJNUZVKPHY-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6,7-dichloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C=C(C(=CC=4C(=O)N3)Cl)Cl)=CC2=C1 UHZOGJNUZVKPHY-UHFFFAOYSA-N 0.000 claims description 3
- HPAGANIUDPQSMV-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6,8-dibromo-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(Br)C=C(C=C4C(=O)N3)Br)=CC2=C1 HPAGANIUDPQSMV-UHFFFAOYSA-N 0.000 claims description 3
- BRRCSZLDAXAOBO-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6,8-dichloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(Cl)C=C(C=C4C(=O)N3)Cl)=CC2=C1 BRRCSZLDAXAOBO-UHFFFAOYSA-N 0.000 claims description 3
- JKXLFKLBAFWNLS-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6-(trifluoromethyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)C(F)(F)F)=CC2=C1 JKXLFKLBAFWNLS-UHFFFAOYSA-N 0.000 claims description 3
- KXVKLLCHKSMFTP-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6-bromo-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)Br)=CC2=C1 KXVKLLCHKSMFTP-UHFFFAOYSA-N 0.000 claims description 3
- ZYYLYOWLMBWDHE-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6-methoxy-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)OC)=CC2=C1 ZYYLYOWLMBWDHE-UHFFFAOYSA-N 0.000 claims description 3
- OZFDDSIXMRDFBG-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7,8-dimethyl-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4C)C)=CC2=C1 OZFDDSIXMRDFBG-UHFFFAOYSA-N 0.000 claims description 3
- TYVPOXDESVQYLO-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7,8-dimethyl-n-[2-(1-methylpyrrolidin-2-yl)ethyl]quinazolin-4-amine;dihydrochloride Chemical compound Cl.Cl.CN1CCCC1CCNC1=NC(C=2OC3=CC=CC=C3C=2)=NC2=C(C)C(C)=CC=C12 TYVPOXDESVQYLO-UHFFFAOYSA-N 0.000 claims description 3
- WXQOTITVYYIHBU-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-8-(trifluoromethyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4C(F)(F)F)=CC2=C1 WXQOTITVYYIHBU-UHFFFAOYSA-N 0.000 claims description 3
- VTXKDPZXWHWGLN-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2SC(C=3NC(C4=CC=CC=C4N=3)=O)=CC2=C1 VTXKDPZXWHWGLN-UHFFFAOYSA-N 0.000 claims description 3
- FLNYPVNCOHTBRP-UHFFFAOYSA-N 2-(1-methylindol-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(C=3N(C4=CC=CC=C4C=3)C)=NC2=C1 FLNYPVNCOHTBRP-UHFFFAOYSA-N 0.000 claims description 3
- UJEDGUGTAFQTDP-UHFFFAOYSA-N 2-(5-chloro-1-benzofuran-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(C=3OC4=CC=C(C=C4C=3)Cl)=NC2=C1 UJEDGUGTAFQTDP-UHFFFAOYSA-N 0.000 claims description 3
- WZTOJSPJLANIDA-UHFFFAOYSA-N 2-(5-methoxy-1-benzofuran-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(C=3OC4=CC=C(C=C4C=3)OC)=NC2=C1 WZTOJSPJLANIDA-UHFFFAOYSA-N 0.000 claims description 3
- BDVOURSEFUIUAE-UHFFFAOYSA-N 2-(5-methyl-1-benzofuran-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(C=3OC4=CC=C(C=C4C=3)C)=NC2=C1 BDVOURSEFUIUAE-UHFFFAOYSA-N 0.000 claims description 3
- VPSHXNCAFRFWMW-UHFFFAOYSA-N 2-(7-methyl-1-benzofuran-2-yl)-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(C3=CC=4C=CC=C(C=4O3)C)=NC2=C1 VPSHXNCAFRFWMW-UHFFFAOYSA-N 0.000 claims description 3
- XTMWMJDTSKFKCW-UHFFFAOYSA-N 2-naphthalen-2-yl-1h-quinazolin-4-one Chemical compound C1=CC=CC2=CC(C3=NC(C4=CC=CC=C4N3)=O)=CC=C21 XTMWMJDTSKFKCW-UHFFFAOYSA-N 0.000 claims description 3
- TWWOVQIRBPJXFD-UHFFFAOYSA-N 2-quinolin-3-yl-1h-quinazolin-4-one Chemical compound C1=CC=CC2=CC(C=3NC(C4=CC=CC=C4N=3)=O)=CN=C21 TWWOVQIRBPJXFD-UHFFFAOYSA-N 0.000 claims description 3
- 230000027311 M phase Effects 0.000 claims description 3
- 238000005576 amination reaction Methods 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- YPHAAVOFLUOLRC-UHFFFAOYSA-N butane-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.CC(N)CCN YPHAAVOFLUOLRC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000004113 cell culture Methods 0.000 claims description 3
- 108091092356 cellular DNA Proteins 0.000 claims description 3
- 239000001963 growth medium Substances 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
- 238000010254 subcutaneous injection Methods 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- HJVKEWLUFHALGQ-UHFFFAOYSA-N 1-[2-(1H-indol-2-yl)quinazolin-4-yl]-3-morpholin-4-ylpropan-1-amine dihydrochloride Chemical compound Cl.Cl.N=1C(C=2NC3=CC=CC=C3C=2)=NC2=CC=CC=C2C=1C(N)CCN1CCOCC1 HJVKEWLUFHALGQ-UHFFFAOYSA-N 0.000 claims description 2
- BLKKXBLAZSIVBX-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-pyrido[2,3-d]pyrimidin-4-one Chemical compound C1=CC=C2OC(C=3NC(C4=CC=CN=C4N=3)=O)=CC2=C1 BLKKXBLAZSIVBX-UHFFFAOYSA-N 0.000 claims description 2
- FKLIJXLRISBXJA-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-pyrido[4,3-d]pyrimidin-4-one Chemical compound C1=CC=C2OC(C=3NC(C4=CN=CC=C4N=3)=O)=CC2=C1 FKLIJXLRISBXJA-UHFFFAOYSA-N 0.000 claims description 2
- GODDQPRIGDDXEJ-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-[3-(dimethylamino)propylamino]quinazoline-8-carboxamide Chemical compound C1=CC=C2OC(C=3N=C(C4=CC=CC(=C4N=3)C(N)=O)NCCCN(C)C)=CC2=C1 GODDQPRIGDDXEJ-UHFFFAOYSA-N 0.000 claims description 2
- MXFRWJOHHXYTLE-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-oxo-1h-quinazoline-7-carboxamide Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4)C(=O)N)=CC2=C1 MXFRWJOHHXYTLE-UHFFFAOYSA-N 0.000 claims description 2
- ISSCYMWJYBQJML-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-5-chloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C=CC=C(C=4C(=O)N3)Cl)=CC2=C1 ISSCYMWJYBQJML-UHFFFAOYSA-N 0.000 claims description 2
- YESHNBBSPUZCRD-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-5-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C=CC=C(C=4C(=O)N3)C)=CC2=C1 YESHNBBSPUZCRD-UHFFFAOYSA-N 0.000 claims description 2
- NPGVRDCXLZOABS-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6-chloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)Cl)=CC2=C1 NPGVRDCXLZOABS-UHFFFAOYSA-N 0.000 claims description 2
- JYYTXEOHTNSCPT-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6-fluoro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)F)=CC2=C1 JYYTXEOHTNSCPT-UHFFFAOYSA-N 0.000 claims description 2
- GHJZOTLKKOVHCH-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)C)=CC2=C1 GHJZOTLKKOVHCH-UHFFFAOYSA-N 0.000 claims description 2
- YLFCNLZFLLSZMG-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7-bromo-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4)Br)=CC2=C1 YLFCNLZFLLSZMG-UHFFFAOYSA-N 0.000 claims description 2
- KTUCTFODTRINPS-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7-methoxy-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4)OC)=CC2=C1 KTUCTFODTRINPS-UHFFFAOYSA-N 0.000 claims description 2
- UUIVRLSVECJLIU-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4)C)=CC2=C1 UUIVRLSVECJLIU-UHFFFAOYSA-N 0.000 claims description 2
- QGMFYFNXVPOHEY-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-7-nitro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C(C(N3)=O)=CC=C(C=4)[N+](=O)[O-])=CC2=C1 QGMFYFNXVPOHEY-UHFFFAOYSA-N 0.000 claims description 2
- UVLPDDSEVJQGQA-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-8-chloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4Cl)=CC2=C1 UVLPDDSEVJQGQA-UHFFFAOYSA-N 0.000 claims description 2
- GNOMBDCSOYAOEV-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-8-methoxy-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4OC)=CC2=C1 GNOMBDCSOYAOEV-UHFFFAOYSA-N 0.000 claims description 2
- TUMRIXQBDDBVQE-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-8-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4C)=CC2=C1 TUMRIXQBDDBVQE-UHFFFAOYSA-N 0.000 claims description 2
- SQKCVVUYQSSKLD-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-8-nitro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4[N+](=O)[O-])=CC2=C1 SQKCVVUYQSSKLD-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5011—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics for testing antineoplastic activity
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Toxicology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Cell Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ546477A NZ546477A (en) | 2006-04-07 | 2006-04-07 | 4-Alkylamino-2-(heterocyclic)quinazolines and their use in cancer therapy |
| NZ546477 | 2006-04-07 | ||
| PCT/NZ2007/000077 WO2007117161A1 (en) | 2006-04-07 | 2007-04-04 | Substituted ring fused azines and their use in cancer therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2007235751A1 true AU2007235751A1 (en) | 2007-10-18 |
Family
ID=38581368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007235751A Abandoned AU2007235751A1 (en) | 2006-04-07 | 2007-04-04 | Substituted ring fused azines and their use in cancer therapy |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20090318479A1 (enExample) |
| EP (1) | EP2004637A4 (enExample) |
| JP (1) | JP2009533338A (enExample) |
| CN (1) | CN101460490A (enExample) |
| AU (1) | AU2007235751A1 (enExample) |
| CA (1) | CA2648323A1 (enExample) |
| NZ (1) | NZ546477A (enExample) |
| WO (1) | WO2007117161A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012046207A1 (en) * | 2010-10-08 | 2012-04-12 | Paraco Technology Limited | Anti-parasitic substituted ring fused azine compounds |
| US8710064B2 (en) * | 2011-10-20 | 2014-04-29 | China Medical University | 2-aryl-4-quinazolinones and their pharmaceutical compositions |
| WO2013182580A1 (en) | 2012-06-07 | 2013-12-12 | F. Hoffmann-La Roche Ag | Pyrrolopyrimidone and pyrrolopyridone inhibitors of tankyrase |
| BR112014030410A2 (pt) | 2012-06-07 | 2017-06-27 | Hoffmann La Roche | inibidores de pirazolopirimidona e pirazolopiridona de tanquirase |
| US9458133B2 (en) | 2013-03-11 | 2016-10-04 | Bristol-Myers Squibb Company | Isoquinolines as potassium ion channel inhibitors |
| WO2015077375A1 (en) | 2013-11-20 | 2015-05-28 | Signalchem Lifesciences Corp. | Quinazoline derivatives as tam family kinase inhibitors |
| US9834550B2 (en) | 2014-10-29 | 2017-12-05 | Dong-A St Co., Ltd. | Pyridopyrimidinone compounds for modulating the catalytic activity of histone lysine demethylases (KDMs) |
| US20170057955A1 (en) * | 2015-08-26 | 2017-03-02 | Dong-A Socio Holdings Co., Ltd. | Pyridopyrimidinone Compounds for Modulating the Catalytic Activity of Histone Lysine Demethylases (KDMs) |
| CN107721982B (zh) * | 2017-10-16 | 2019-12-03 | 中山大学 | 一种抗肥胖症化合物及其制备方法和应用 |
| CN110483394A (zh) * | 2019-09-02 | 2019-11-22 | 广东工业大学 | 一种化合物的应用 |
| CN113072543B (zh) * | 2020-01-03 | 2022-07-22 | 南方医科大学 | 一种2-芳杂环基喹唑啉酮类化合物及其制备方法和用途 |
| WO2021155426A1 (en) * | 2020-02-04 | 2021-08-12 | TroBio Therapeutics Pty Ltd | Quinazoline compounds and the use thereof in the treatment of cancer |
| US11548885B2 (en) | 2020-09-21 | 2023-01-10 | Landos Biopharma, Inc. | NLRX1 ligands |
| CN114044769B (zh) * | 2021-11-25 | 2023-12-12 | 中山大学 | 一种β-吲哚喹唑啉酮衍生物及其制备方法和应用 |
| CN117247374A (zh) * | 2022-06-10 | 2023-12-19 | 成都先导药物开发股份有限公司 | 一种bcl-xl抑制剂及其制药用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897432A (en) * | 1971-04-21 | 1975-07-29 | Merck & Co Inc | Substituted benzimidazole derivatives |
| YU35401A (sh) * | 1998-12-02 | 2005-07-19 | Pfizer Products Inc. | POSTUPCI I PREPARATI ZA USPOSTAVLJANJE UJEDNAČENE STABILNOSTI PROTEINA IZ p53 FAMILIJE |
| DK1088818T3 (da) * | 1999-10-01 | 2005-03-14 | Hoffmann La Roche | Quinolin-4-yl-derivater |
| ATE503743T1 (de) * | 2000-04-27 | 2011-04-15 | Astellas Pharma Inc | Kondensierte heteroarylderivate |
| WO2002062767A1 (en) * | 2001-02-07 | 2002-08-15 | Sumitomo Pharmaceuticals Company, Limited | Novel quinazoline derivatives |
-
2006
- 2006-04-07 NZ NZ546477A patent/NZ546477A/en not_active IP Right Cessation
-
2007
- 2007-04-04 WO PCT/NZ2007/000077 patent/WO2007117161A1/en not_active Ceased
- 2007-04-04 US US12/296,377 patent/US20090318479A1/en not_active Abandoned
- 2007-04-04 EP EP07747705A patent/EP2004637A4/en not_active Withdrawn
- 2007-04-04 CN CNA2007800204647A patent/CN101460490A/zh active Pending
- 2007-04-04 JP JP2009504144A patent/JP2009533338A/ja active Pending
- 2007-04-04 AU AU2007235751A patent/AU2007235751A1/en not_active Abandoned
- 2007-04-04 CA CA002648323A patent/CA2648323A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101460490A (zh) | 2009-06-17 |
| EP2004637A1 (en) | 2008-12-24 |
| EP2004637A4 (en) | 2010-11-03 |
| WO2007117161A1 (en) | 2007-10-18 |
| NZ546477A (en) | 2009-04-30 |
| CA2648323A1 (en) | 2007-10-18 |
| JP2009533338A (ja) | 2009-09-17 |
| US20090318479A1 (en) | 2009-12-24 |
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Legal Events
| Date | Code | Title | Description |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |