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US 6,441,189 B1Granted
Process for the preparation of matrix metalloproteinase inhibitors
AssigneeAbbott Laboratories
InventorsAnne E. Bailey, David R. Hill, Chi-nung W. Hsiao, Ravi Kurukulasuriya, Steve Wittenberger, Todd McDermott, Maureen A. McLaughlin
Life of this patent
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Abstract
The instant invention provides a process for the synthesis of matrix metalloproteinase inhibitors.
Claims4
A process for preparing a compound of formula (5-a)
- wherein
- X is O or S;
- R1 is selected from the group consiting of hydrogen, an amino protecting group, and —OR2;
- R2 is hydrogen protecting group;
- L1 is —O— or —N(R3)—, wherein R3 is hydrogen or an amino protecting group;
- L2 is —O— or —S—;
- and
- Q1 is selected from the group consisting of halide, methanesulfonate, and trifluoromethanesulfonate;
- the process comprising:
- (a) activating the hydroxyl of the compound of formula (3)
- wherein X, R1 and L1 are as defined above,
- (b) reacting the product of step (a), a compound of formula (4)
- wherein L2 and Q1 are as defined above, and base to provide the compound of formula (5-a)
10 more elements
A process for preparing a compound of formula (5-b)
- wherein
- X is O or S;
- R1 is selected from the group consisting of hydrogen, an amino protecting group, and —OR2;
- R2 is hydrogen or a hydroxy protecting group;
- L1 is —O— or —N(R3)—, wherein R3 is hydrogen or an amino protecting group;
- L2 is —O— or —S—;
- Y is C(H);
- R6 is selected from the group consisting of alkoxy, alkoxyalkyl, alkyl, aminosulfonyl, aminosulfonylalkyl, aryl, arylalkyl, cyano, cyanoalkyl, halo, haloalkyl, (heterocycle)oxy, (heterocycle)oxyalkyl, hydroxy, hydroxyalkyl, phenylalkoxy, phenylalkoxyalkyl phenoxy, phenoxyalkyl, perfluoroalkoxy, perfluoroalkoxyalkyl, perfluorothioalkoxy, perfluorothioalkoxyalkyl, sulfinyl, sulfinylalkylsulfonyl, sulfonylalkyl, thioalkoxy, and thioalkoxyalkyl;
- the process comprising:
- reacting a compound of formula (5-a)
- wherein X, R1, L1, L2 and Q1 are as defined above, and a compound of formula (6)
- wherein
- R6 and Y are as defined above;
- and
- Q2 is selected from the group consisting of trialkylstannanes, boronic acid, boronic esters, magnesium halides, zinc halides, and silyl(alkyl)cyclobutanes,
- and a coupling catalyst.
13 more elements
Dependencies are inferred from the claim text.