AU653348B2 - Heterocyclic anthracyclinone and anthracycline analogs - Google Patents

Info

Publication number

AU653348B2

AU653348B2 AU80973/91A AU8097391A AU653348B2 AU 653348 B2 AU653348 B2 AU 653348B2 AU 80973/91 A AU80973/91 A AU 80973/91A AU 8097391 A AU8097391 A AU 8097391A AU 653348 B2 AU653348 B2 AU 653348B2

Authority

AU

Australia

Prior art keywords

compound

formula

group

dioxo

hydrogen

Prior art date

1990-06-11

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 229940045799 anthracyclines and related substance Drugs 0.000 title claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 442
• 239000000203 mixture Substances 0.000 claims description 163
• -1 trifluoroacyl Chemical group 0.000 claims description 139
• 238000000034 method Methods 0.000 claims description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 239000001257 hydrogen Substances 0.000 claims description 101
• 125000003118 aryl group Chemical group 0.000 claims description 98
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 85
• 206010028980 Neoplasm Diseases 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
• 239000002904 solvent Substances 0.000 claims description 76
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 72
• 150000002431 hydrogen Chemical class 0.000 claims description 64
• 125000002252 acyl group Chemical group 0.000 claims description 60
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 58
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
• 238000011282 treatment Methods 0.000 claims description 44
• XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims description 40
• 229910052760 oxygen Inorganic materials 0.000 claims description 38
• 239000000460 chlorine Substances 0.000 claims description 37
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 36
• 239000001301 oxygen Substances 0.000 claims description 36
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 201000011510 cancer Diseases 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 230000008569 process Effects 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 26
• 150000002576 ketones Chemical class 0.000 claims description 26
• LZPBKINTWROMEA-UHFFFAOYSA-N tetracene-5,12-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C(=O)C3=CC2=C1 LZPBKINTWROMEA-UHFFFAOYSA-N 0.000 claims description 25
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
• AKHSBAVQPIRVAG-UHFFFAOYSA-N 4h-isochromene-1,3-dione Chemical compound C1=CC=C2C(=O)OC(=O)CC2=C1 AKHSBAVQPIRVAG-UHFFFAOYSA-N 0.000 claims description 21
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 21
• 239000003795 chemical substances by application Substances 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 21
• 230000000694 effects Effects 0.000 claims description 20
• 238000003786 synthesis reaction Methods 0.000 claims description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 150000001413 amino acids Chemical class 0.000 claims description 18
• 230000000259 anti-tumor effect Effects 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 16
• 150000001241 acetals Chemical class 0.000 claims description 16
• 150000002338 glycosides Chemical class 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 230000015572 biosynthetic process Effects 0.000 claims description 15
• 229930182470 glycoside Natural products 0.000 claims description 15
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
• 230000001590 oxidative effect Effects 0.000 claims description 14
• 241000282414 Homo sapiens Species 0.000 claims description 13
• 230000001093 anti-cancer Effects 0.000 claims description 13
• 150000001720 carbohydrates Chemical class 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 12
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 241000124008 Mammalia Species 0.000 claims description 10
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 230000002378 acidificating effect Effects 0.000 claims description 8
• 230000000844 anti-bacterial effect Effects 0.000 claims description 8
• 229940121375 antifungal agent Drugs 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 239000011593 sulfur Substances 0.000 claims description 8
• 229940124597 therapeutic agent Drugs 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 230000000843 anti-fungal effect Effects 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 150000004053 quinones Chemical class 0.000 claims description 7
• OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 claims description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 6
• 230000000840 anti-viral effect Effects 0.000 claims description 6
• 125000003435 aroyl group Chemical group 0.000 claims description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
• 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 239000012039 electrophile Substances 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 150000002772 monosaccharides Chemical class 0.000 claims description 5
• 229920001542 oligosaccharide Polymers 0.000 claims description 5
• 150000002482 oligosaccharides Chemical class 0.000 claims description 5
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
• 238000011160 research Methods 0.000 claims description 5
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
• YCFAGKLOINRREV-UHFFFAOYSA-N 5,8-dimethoxy-3,4-dihydro-1h-isochromene-3-carboxylic acid Chemical compound C1C(C(O)=O)OCC2=C1C(OC)=CC=C2OC YCFAGKLOINRREV-UHFFFAOYSA-N 0.000 claims description 4
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 4
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 238000007363 ring formation reaction Methods 0.000 claims description 4
• 230000008685 targeting Effects 0.000 claims description 4
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
• NYJBTJMNTNCTCP-UHFFFAOYSA-N 2,5-dimethoxybenzoic acid Chemical compound COC1=CC=C(OC)C(C(O)=O)=C1 NYJBTJMNTNCTCP-UHFFFAOYSA-N 0.000 claims description 3
• 239000002841 Lewis acid Substances 0.000 claims description 3
• 239000003242 anti bacterial agent Substances 0.000 claims description 3
• 239000013522 chelant Substances 0.000 claims description 3
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
• 239000003112 inhibitor Substances 0.000 claims description 3
• 150000007517 lewis acids Chemical class 0.000 claims description 3
• 229910052751 metal Inorganic materials 0.000 claims description 3
• 239000002184 metal Substances 0.000 claims description 3
• 102000004169 proteins and genes Human genes 0.000 claims description 3
• 108090000623 proteins and genes Proteins 0.000 claims description 3
• 230000001131 transforming effect Effects 0.000 claims description 3
• ZGZKKXMMRZAVCJ-UHFFFAOYSA-N 1,1-dimethoxy-3,4-dihydroisothiochromene Chemical compound C1=CC=C2C(OC)(OC)SCCC2=C1 ZGZKKXMMRZAVCJ-UHFFFAOYSA-N 0.000 claims description 2
• JVFLPIRHJLSPNT-UHFFFAOYSA-N 3-ethenyl-1-methoxy-3,4-dihydro-1h-isochromene-5,8-dione Chemical compound O=C1C=CC(=O)C2=C1C(OC)OC(C=C)C2 JVFLPIRHJLSPNT-UHFFFAOYSA-N 0.000 claims description 2
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 229940088710 antibiotic agent Drugs 0.000 claims description 2
• 125000005251 aryl acyl group Chemical group 0.000 claims description 2
• 230000001419 dependent effect Effects 0.000 claims description 2
• 238000011156 evaluation Methods 0.000 claims description 2
• 150000004678 hydrides Chemical class 0.000 claims description 2
• 229960000908 idarubicin Drugs 0.000 claims description 2
• 238000001149 thermolysis Methods 0.000 claims description 2
• 229940044170 formate Drugs 0.000 claims 40
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 8
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 4
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
• IRTOOLQOINXNHY-UHFFFAOYSA-N 1-(2-aminoethylamino)ethanol Chemical compound CC(O)NCCN IRTOOLQOINXNHY-UHFFFAOYSA-N 0.000 claims 2
• 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims 2
• 230000003301 hydrolyzing effect Effects 0.000 claims 2
• 239000002502 liposome Substances 0.000 claims 2
• 125000004001 thioalkyl group Chemical group 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• HHZHOOXEMGLCJA-UHFFFAOYSA-N 1-(1-hydroxy-5,8-dimethoxy-3,4-dihydro-1h-isochromen-3-yl)ethanone Chemical compound OC1OC(C(C)=O)CC2=C1C(OC)=CC=C2OC HHZHOOXEMGLCJA-UHFFFAOYSA-N 0.000 claims 1
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
• DGJQWDOLPJWEGM-UHFFFAOYSA-N 3,4-dihydro-1H-isochromene-5,8-dione Chemical class O=C1C=CC(=O)C2=C1CCOC2 DGJQWDOLPJWEGM-UHFFFAOYSA-N 0.000 claims 1
• REQPMBUAVWEKEQ-UHFFFAOYSA-N 3-acetyl-3,4-dihydro-1h-isochromene-5,8-dione Chemical compound O=C1C=CC(=O)C2=C1COC(C(=O)C)C2 REQPMBUAVWEKEQ-UHFFFAOYSA-N 0.000 claims 1
• MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 claims 1
• FNNPIPQJIJEIHE-UHFFFAOYSA-N 4h-isothiochromene-1,3-dione Chemical compound C1=CC=C2C(=O)SC(=O)CC2=C1 FNNPIPQJIJEIHE-UHFFFAOYSA-N 0.000 claims 1
• WFPUBEDBBOGGIQ-UHFFFAOYSA-N 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=C(Cl)C(Cl)=CC=C21 WFPUBEDBBOGGIQ-UHFFFAOYSA-N 0.000 claims 1
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