EA037119B1 - Замещенные 2,4-диаминохинолины в качестве новых противораковых средств - Google Patents

Info

Publication number

EA037119B1

EA037119B1 EA201790949A EA201790949A EA037119B1 EA 037119 B1 EA037119 B1 EA 037119B1 EA 201790949 A EA201790949 A EA 201790949A EA 201790949 A EA201790949 A EA 201790949A EA 037119 B1 EA037119 B1 EA 037119B1

Authority

EA

Eurasian Patent Office

Prior art keywords

leukemia

cell

inhibitor

optionally substituted

cancer

Prior art date

2014-10-31

Links

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 13
• NKXSJFUIFJMXED-UHFFFAOYSA-N quinoline-2,4-diamine Chemical class C1=CC=CC2=NC(N)=CC(N)=C21 NKXSJFUIFJMXED-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 106
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 30
• 201000010099 disease Diseases 0.000 claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 238000011282 treatment Methods 0.000 claims abstract description 13
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 11
• 230000002062 proliferating effect Effects 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 8
• 210000004027 cell Anatomy 0.000 claims description 147
• -1 linear or branched Chemical group 0.000 claims description 105
• 206010028980 Neoplasm Diseases 0.000 claims description 45
• 239000000203 mixture Substances 0.000 claims description 30
• 201000011510 cancer Diseases 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 239000003112 inhibitor Substances 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 206010009944 Colon cancer Diseases 0.000 claims description 18
• 241000282414 Homo sapiens Species 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 210000000130 stem cell Anatomy 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• JICRJOOPMADODM-UHFFFAOYSA-N 4-[4-(tert-butylamino)piperidin-1-yl]-N-(4-chlorophenyl)quinolin-2-amine Chemical compound ClC1=CC=C(C=C1)NC1=NC2=CC=CC=C2C(=C1)N1CCC(CC1)NC(C)(C)C JICRJOOPMADODM-UHFFFAOYSA-N 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• MWCBJXZYGHXXPA-UHFFFAOYSA-N 4-N-[4-[4-(tert-butylamino)piperidin-1-yl]quinolin-2-yl]-2-methyl-1-N-pyrimidin-2-ylbenzene-1,4-diamine Chemical compound CC=1C=C(C=CC=1NC1=NC=CC=N1)NC1=NC2=CC=CC=C2C(=C1)N1CCC(CC1)NC(C)(C)C MWCBJXZYGHXXPA-UHFFFAOYSA-N 0.000 claims description 10
• MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 10
• 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 10
• 239000005511 L01XE05 - Sorafenib Substances 0.000 claims description 10
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• WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 10
• QVXSJSXAVQJXOV-UHFFFAOYSA-N 4-[4-(tert-butylamino)piperidin-1-yl]-N-[(4-chlorophenyl)methyl]quinolin-2-amine Chemical compound ClC1=CC=C(CNC2=NC3=CC=CC=C3C(=C2)N2CCC(CC2)NC(C)(C)C)C=C1 QVXSJSXAVQJXOV-UHFFFAOYSA-N 0.000 claims description 9
• 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 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 8
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• 210000005102 tumor initiating cell Anatomy 0.000 claims description 8
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 7
• 229960000397 bevacizumab Drugs 0.000 claims description 7
• 230000012010 growth Effects 0.000 claims description 7
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• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
• 229940034982 antineoplastic agent Drugs 0.000 claims description 6
• RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 claims description 6
• 229960000452 diethylstilbestrol Drugs 0.000 claims description 6
• 229960004679 doxorubicin Drugs 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 229940079322 interferon Drugs 0.000 claims description 6
• CYOHGALHFOKKQC-UHFFFAOYSA-N selumetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl CYOHGALHFOKKQC-UHFFFAOYSA-N 0.000 claims description 6
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 6
• JTRFEMRCLWXABU-UHFFFAOYSA-N 4-N-[4-[4-(tert-butylamino)piperidin-1-yl]quinolin-2-yl]-2-methyl-1-N-pyrimidin-2-ylbenzene-1,4-diamine hydrochloride Chemical compound Cl.Cc1cc(Nc2cc(N3CCC(CC3)NC(C)(C)C)c3ccccc3n2)ccc1Nc1ncccn1 JTRFEMRCLWXABU-UHFFFAOYSA-N 0.000 claims description 5
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
• HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 claims description 5
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 208000029742 colonic neoplasm Diseases 0.000 claims description 5
• 229960000684 cytarabine Drugs 0.000 claims description 5
• 230000004069 differentiation Effects 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 238000012360 testing method Methods 0.000 claims description 5
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
• JICOGKJOQXTAIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 JICOGKJOQXTAIP-UHFFFAOYSA-N 0.000 claims description 4
• AXRCEOKUDYDWLF-UHFFFAOYSA-N 3-(1-methyl-3-indolyl)-4-[1-[1-(2-pyridinylmethyl)-4-piperidinyl]-3-indolyl]pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=CC=C11)=CN1C(CC1)CCN1CC1=CC=CC=N1 AXRCEOKUDYDWLF-UHFFFAOYSA-N 0.000 claims description 4
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 4
• 108010024976 Asparaginase Proteins 0.000 claims description 4
• 108010050904 Interferons Proteins 0.000 claims description 4
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• 241001465754 Metazoa Species 0.000 claims description 4
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 4
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• GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 claims description 4
• PIQCTGMSNWUMAF-UHFFFAOYSA-N chembl522892 Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C=3C(NC4=CC=CC(F)=C4C=3N)=O)C2=C1 PIQCTGMSNWUMAF-UHFFFAOYSA-N 0.000 claims description 4
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
• 229960004316 cisplatin Drugs 0.000 claims description 4
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 4
• 229960000975 daunorubicin Drugs 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims description 4
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• OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims description 4
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• KSOVGRCOLZZTPF-QMKUDKLTSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC(C=C1C)=CC=C1N1CCN(C)CC1 KSOVGRCOLZZTPF-QMKUDKLTSA-N 0.000 claims description 2
• PFJFPBDHCFMQPN-RGJAOAFDSA-N (1s,3s,7s,10r,11s,12s,16r)-3-[(e)-1-[2-(aminomethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-7,11-dihydroxy-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CN)=N1 PFJFPBDHCFMQPN-RGJAOAFDSA-N 0.000 claims description 2
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• MHFUWOIXNMZFIW-WNQIDUERSA-N (2s)-2-hydroxypropanoic acid;n-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide Chemical compound C[C@H](O)C(O)=O.C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 MHFUWOIXNMZFIW-WNQIDUERSA-N 0.000 claims description 2
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