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US 7,795,260 B2Granted
Synthesis of naturally occurring ecteinascidins and related compounds
AssigneePharma Mar, S.A.
InventorsValentin Martinez Barrasa, Pilar Gallego, Carmen Cuevas, Simon Munt, Ignacio Manzanares, Roberto Menchaca, Natividad Rodriguez, Alberto Rodriguez
Life of this patent
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Abstract
Ecteinascidin compounds with a quinone ring for ring E are active as anti-cancer agents. Related processes and compounds are provided.
Claims22
A compound of formula:
- wherein
- Ra and Rb together with the carbon to which they are attached form a group of formula:
- where Rd is a substituted or unsubstituted R′, OR′, —(C═O)R′, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl;
- wherein R′ is selected from the group consisting of OH, NO2, NH2, SH, CN, halogen, C(═O)H, C(═O)CH3, CO2H, CO2CH3, C1-C6 alkyl, alkenyl, alkynyl, aryl, aralkyl and heterocyclic;
- each X1 in:
- is independently selected from hydrogen or substituted or unsubstituted R′, OR′, —(C═O)R′, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted aralkyl;
- wherein R′ is selected from the group consisting of H, OH, NO2, NH2, SH, CN, halogen, C(═O)H, C(═O)CH3, CO2H, CO2CH3, C1-C6 alkyl, alkenyl, alkynyl, aryl, aralkyl and heterocyclic;
- R7 is —OCH3 and R8 is —OH or R7 and R8 together form a group —O—CH2—O—;
- R12a is hydrogen, acyl, alkenyl, or alkyl-O—CO—;
- R21 is —H, OH or CN;
- X is —O— or —NH—;
- R5 and R18 are each —OX1, wherein each X1 is independently selected from hydrogen, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, or —C(═O)R′ wherein R′ is selected from hydrogen, OH, NO2, NH2, SH, CN, halogen, C1-C6 alkyl, alkenyl, alkynyl, aryl, aralkyl, and heterocyclic.
9 more elements
Dependencies are inferred from the claim text.