DK3212629T3 - Substituted 2,4 diamino-quinoline as new anticancer agents - Google Patents

Info

Publication number

DK3212629T3

DK3212629T3 DK15837091.6T DK15837091T DK3212629T3 DK 3212629 T3 DK3212629 T3 DK 3212629T3 DK 15837091 T DK15837091 T DK 15837091T DK 3212629 T3 DK3212629 T3 DK 3212629T3

Authority

DK

Denmark

Prior art keywords

optionally substituted

substituted

alkyl

inhibitor

pharmaceutical composition

Prior art date

2014-10-31

Links

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 12
• NKXSJFUIFJMXED-UHFFFAOYSA-N quinoline-2,4-diamine Chemical class C1=CC=CC2=NC(N)=CC(N)=C21 NKXSJFUIFJMXED-UHFFFAOYSA-N 0.000 title 1
• 210000004027 cell Anatomy 0.000 claims description 135
• -1 nitro, carboxy Chemical group 0.000 claims description 106
• 150000001875 compounds Chemical class 0.000 claims description 102
• 229910052757 nitrogen Inorganic materials 0.000 claims description 57
• 125000005842 heteroatom Chemical group 0.000 claims description 44
• 229910052760 oxygen Inorganic materials 0.000 claims description 42
• 229910052717 sulfur Inorganic materials 0.000 claims description 42
• 239000008194 pharmaceutical composition Substances 0.000 claims description 38
• 239000000203 mixture Substances 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 28
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 239000002105 nanoparticle Substances 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 22
• 239000003112 inhibitor Substances 0.000 claims description 21
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 201000011510 cancer Diseases 0.000 claims description 16
• 210000000130 stem cell Anatomy 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 206010009944 Colon cancer Diseases 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 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 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 210000004185 liver Anatomy 0.000 claims description 13
• 229920006395 saturated elastomer Polymers 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 208000032839 leukemia Diseases 0.000 claims description 11
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• 239000002202 Polyethylene glycol Substances 0.000 claims description 9
• 229920001223 polyethylene glycol Polymers 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
• 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 9
• 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 8
• 239000005511 L01XE05 - Sorafenib Substances 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 229960004679 doxorubicin Drugs 0.000 claims description 8
• 230000001613 neoplastic effect Effects 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
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• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
• 239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
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• 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 6
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• 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
• 229960004768 irinotecan Drugs 0.000 claims description 6
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 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
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 210000005102 tumor initiating cell Anatomy 0.000 claims description 6
• 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 5
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• 108010078049 Interferon alpha-2 Proteins 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 229960000452 diethylstilbestrol Drugs 0.000 claims description 5
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 claims description 5
• 125000006373 (C2-C10) alkyl 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
• 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 4
• 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 4
• DLXMKLHCUTYCGO-UHFFFAOYSA-N 4-[4-(tert-butylamino)piperidin-1-yl]-N-[(4-chlorophenyl)methyl]quinolin-2-amine hydrochloride Chemical compound Cl.CC(C)(C)NC1CCN(CC1)c1cc(NCc2ccc(Cl)cc2)nc2ccccc12 DLXMKLHCUTYCGO-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims description 4
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• 229950009003 cilengitide Drugs 0.000 claims description 4
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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