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US 2011/0218177 A1Published application
Prodrugs of oxazolidinone cetp inhibitors
AssigneeMerck Sharp & Dohme Corp.
InventorsSander G. Mills, Amjad Ali, Cameron Smith
Life of this patent
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Abstract
The compounds of Formula I are pro-drugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.
Claims18
A compound of formula I, or a pharmaceutically acceptable salt thereof:
- wherein R1 is selected from H and C1-4alkyl, which is optionally substituted with 1-5 F groups;
- Each R2 is independently selected from the group consisting of halogen, —CN, C1-4alkyl, and —OC1-4alkyl, wherein C1-4alkyl and —OC1-4alkyl are optionally substituted with 1-5 halogens;
- R3 is selected from the group consisting of H, halogen, C1-4alkyl, and —OC1-4alkyl, wherein C1-4alkyl and —OC1-4alkyl are optionally substituted with 1-5 halogens;
- R4 and R5 are each independently selected from the group consisting of halogen, C1-4alkyl, and —OC1-4alkyl, wherein C1-4alkyl and —OC1-4alkyl are optionally substituted with 1-5 halogens;
- R6 is selected from H and C1-C5 alkyl optionally substituted with 1-5 halogens and optionally substituted with 1-2 phenyl groups, wherein phenyl is optionally substituted with 1-3 groups independently selected from halogen, C1-C3 alkyl, —OC1-C3 alkyl, CF3, and —OCF3;
- R7 is selected from H and C1-C3 alkyl optionally substituted with 1-3 F;
- X is selected from —OZ and —SZ, wherein Z is selected from:
- (a) C1-C5 alkyl which optionally includes an —O— atom between 2 adjacent carbon atoms, wherein C1-C5 alkyl is optionally substituted with 1-5 halogens and is optionally substituted with 1-2 substituent groups independently selected from phenyl, —C(═O)OR6, —OP(═O)(OR7)2, and —P(═O)(OR7)2, wherein phenyl is optionally substituted with 1-3 groups independently selected from halogen, —C(═O)OR7, and C1-C3alkyl optionally substituted with 1-3 halogens;
- and
- (b) phenyl, wherein phenyl is optionally substituted with 1-3 groups independently selected from halogen;
- C1-C5alkyl;
- —OC1-C5alkyl;
- —C(═O)OR7;
- and C5-C7cycloalkyl optionally substituted with 1-2 groups independently selected from halogen, C1-C3alkyl, —OC1-C3alkyl, CF3, and —OCF3;
- wherein C1-C5alkyl and —OC1-C5alkyl are optionally substituted with 1-5 F and are optionally substituted with 1-2 groups independently selected from —C(═O)OR7, —N(R7)2, —OP(═O)(OR7)2, and —P(═O)(OR7)2;
- a and b are integers independently selected from 0-4;
- and
- c is an integer from 0-2.
15 more elements
(canceled)
Dependencies are inferred from the claim text.