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US 6,486,324 B2Granted
Ring opening metathesis of alkenes
AssigneeSepracor Inc.
InventorsGregory D. Cuny, Jingrong Cao, James R. Hauske
Life of this patent
Estimating the term…
Abstract
Methods for performing ring-opening cross-metathesis reactions on solid support are disclosed. Substituted cyclic compounds, libraries of the compounds, and methods of using the compounds to treat bacterial infections are also disclosed.
Claims5
A compound represented by the formula (Formula II):
- in which
- X is CR′1R′2Q;
- Q is a direct bond:
- R1 and R2 are each independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heterocyclyl, amino, acylamino, hydroxy, alkoxy, aryloxy, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, aminocarbonyloxy, or alkylthio;
- or R1 and R2 taken together are O or S;
- R′1 and R′2 are each independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heterocyclyl, amino, acylamino, hydroxy, alkoxy, aryloxy, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, aminocarbonyloxy, or alkylthio;
- or R′1 and R′2 taken together are O or S;
- R3 and R4 are each independently hydrogen, halogen, cyano, nitro, boronato, stannyl, silyl, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocyclyl, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, or aminocarbonyloxy;
- R5 is hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl or heterocyclyl;
- Ra and Rb are each hydrogen, or Ra and Rb taken together are O;
- or a salt thereof.
8 more elements
A method for preparing a compound represented by the formula (Formula II):
- in which
- X is CR′1R′2Q;
- Q is a direct bond;
- R1 and R2 are each independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heterocyclyl, amino, acylamino, hydroxy, alkoxy, aryloxy, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, aminocarbonyloxy, or alkylthio;
- or R1 and R2 taken together are O or S;
- R′1 and R′2 are each independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heterocyclyl, amino, acylamino, hydroxy, alkoxy, aryloxy, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, aminocarbonyloxy, or alkylthio;
- or R′1 and R′2 taken together are O or S;
- R3 and R4 are each independently hydrogen, halogen, cyano, nitro, boronato, stannyl, silyl, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocyclyl, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, or aminocarbonyloxy;
- R5 is hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl or heterocyclyl;
- Ra and Rb are each hydrogen, or Ra and Rb taken together are O;
- or a salt thereof;
- the method comprising the steps of:
- reacting a compound represented by the formula (Formula V):
- in which
- X, R1, R2, R5, Ra and Rb are as defined above;
- and P is hydrogen or a protecting group;
- with a compound represented by the formula (Formula IV):
- in which
- R3 and R4 are as defined above;
- under ring opening cross-metathesis conditions, such that a cross-metathesis product is prepared;
- and
- cyclizing the cross-metathesis product, such that a compound of Formula II is prepared.
19 more elements
Dependencies are inferred from the claim text.