AP340A - Heterocyclic anathracyclinone and anathracycline analogs - Google Patents

Info

Publication number

AP340A

AP340A APAP/P/1991/000278A AP9100278A AP340A AP 340 A AP340 A AP 340A AP 9100278 A AP9100278 A AP 9100278A AP 340 A AP340 A AP 340A

Authority

AP

ARIPO

Prior art keywords

compound

formula

group

pyran

bad original

Prior art date

1990-06-11

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• 238000000034 method Methods 0.000 claims abstract description 82
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 230000008569 process Effects 0.000 claims abstract description 15
• 150000001875 compounds Chemical class 0.000 claims description 450
• 239000000203 mixture Substances 0.000 claims description 162
• -1 trifluoroacyl Chemical group 0.000 claims description 151
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
• 229910052739 hydrogen Inorganic materials 0.000 claims description 100
• 239000001257 hydrogen Substances 0.000 claims description 98
• 125000003118 aryl group Chemical group 0.000 claims description 96
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• 125000000217 alkyl group Chemical group 0.000 claims description 92
• 239000002904 solvent Substances 0.000 claims description 75
• 150000002431 hydrogen Chemical group 0.000 claims description 71
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 69
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 66
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
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• 206010028980 Neoplasm Diseases 0.000 claims description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
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• 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
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• 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 27
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• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
• 239000004472 Lysine Substances 0.000 claims description 6
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
• 235000004279 alanine Nutrition 0.000 claims description 6
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 6
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• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
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• 229920001542 oligosaccharide Polymers 0.000 claims description 6
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• 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
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