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US 6,284,789 B1Granted
Formation and composition of new optically active compounds
AssigneeThe Research Foundation of State University of New York
InventorsRobert T. LaLonde, Frank D. Ramdayal, Mianji Zhang
Life of this patent
Estimating the term…
Abstract
The present invention is directed to tetrahydronaphthalene derivatives of α-conindendrin, β-conindendrin, sikkimotoxin, and podophyllotoxin having at least one methyleneoxy bridge wherein the oxygen atom extends to the benzhydrylic carbon atom.
Claims13
A dioxatricyclodecane having two methyleneoxy bridges and comprising the formula:
- wherein
- R1 and R2 together with the atoms to which they are bonded form a substituted or unsubstituted homocyclic or heterocyclic saturated, unsaturated, or aromatic ring, or R1 and R2 are independently selected from the group consisting of hydrogen;
- hydroxy;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- substituted or unsubstituted aralkoxy;
- substituted or unsubstituted alkylthio;
- substituted or unsubstituted arylthio;
- substituted or unsubstituted aralkylthio;
- substituted or unsubstituted amino;
- a carboxylic acid group;
- a carboxylic acid ester group;
- a carbocylic acid amide group;
- and a group having the formula —OC(O)Ra, where Ra is selected from the group consisting of substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- R3, R4, and R7 are independently selected from the group consisting of hydrogen;
- hydroxy;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- substituted or unsubstituted aralkoxy;
- substituted or unsubstituted alkylthio;
- substituted or unsubstituted arylthio;
- substituted or unsubstituted aralkylthio;
- substituted or unsubstituted amino;
- a carboxylic acid group;
- a carboxylic acid ester group;
- a carbocylic acid amide group;
- and a group having the formula —OC(O)Rb, where Rb is selected from the group consisting of substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- R5 and R6 together with the atoms to which they are bonded form a substituted of unsubstituted, homocyclic or heterocyclic, saturated, unsaturated, or aromatic ring, or R5 and R6 are independently selected from the group consisting of hydrogen;
- hydroxy;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- substituted or unsubstituted aralkoxy;
- substituted or unsubstituted alkylthio;
- substituted or unsubstituted arylthio;
- substituted or unsubstituted aralkylthio;
- substituted or unsubstituted amino;
- a carboxylic acid group;
- a carboxylic acid ester group;
- a carbocylic acid amide group;
- and a group having the formula —OC(O)Rc, where Rc is selected from the group consisting of substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- R8 and R9 together with the atoms to which they are bonded form a substituted of unsubstituted, homocyclic or heterocyclic, saturated, unsaturated, or aromatic ring, or R8 and R9 are independently selected from the group consisting of hydrogen;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- substituted or unsubstituted aralkoxy;
- substituted or unsubstituted alkylthio;
- substituted or unsubstituted arylthio;
- substituted or unsubstituted aralkylthio;
- substituted or unsubstituted amino;
- a carboxylic acid group;
- a carboxylic acid ester group;
- a carbocylic acid amide group;
- and a group having the formula —OC(O)Rd, where Rd is selected from the group consisting of substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- R10 and R11 together with the atoms to which they are bonded form a substituted of unsubstituted, homocyclic or heterocyclic, saturated, unsaturated, or aromatic ring, or R10 and R11 are independently selected from the group consisting of hydrogen;
- hydroxy;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- substituted or unsubstituted aralkoxy;
- substituted or unsubstituted alkylthio;
- substituted or unsubstituted arylthio;
- substituted or unsubstituted aralkylthio;
- substituted or unsubstituted amino;
- a carboxylic acid group;
- a carboxylic acid ester group;
- a carbocylic acid amide group;
- and a group having the formula —OC(O)Re where Re is selected from the group consisting of substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- R12 is a group having the formula:
- R13, R14, R17, and R18 are independently selected from the group consisting of hydrogen;
- hydroxy;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- substituted or unsubstituted aralkoxy;
- substituted or unsubstituted alkylthio;
- substituted or unsubstituted arylthio;
- substituted or unsubstituted aralkylthio;
- substituted or unsubstituted amino;
- a carboxylic acid group;
- a carboxylic acid ester group;
- a carbocylic acid amide group;
- and a group having the formula —OC(O)Rf, where Rf is selected from the group consisting of substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted aryl;
- a substituted or unsubstituted saturated, unsaturated, or aromatic heterocyclic group;
- R15 and R16 are independently selected from the group consisting of hydroxy;
- substituted or unsubstituted alkoxy;
- substituted or unsubstituted arylxoxy;
- and substituted or unsubstituted aralkoxy;
- or R15 and R16, together, have the formula —O—Z—O— where Z is a substituted or unsubstituted alkylene moiety.
123 more elements
Dependencies are inferred from the claim text.