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US 12,715,885 B2Granted
Chiral synthons for the synthesis of chiral phosphorothioates
AssigneeBoehringer Ingelheim International GmbH
InventorsYongda Zhang, Linglin Wu
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Abstract
This invention relates to compounds of Formula (I) useful as synthons for a general synthetic method for making chiral phosphorothioates, to their preparation and to their use in a robust large scale process for making P-chiral phosphorothioates.
Claims16
A compound of formula (I)
- wherein
- n is 0, 1, 2, 3, 4, 5, or 6;
- each X is selected from the group consisting of a bond;
- —(CH2)m— optionally substituted with halogen, —CN, C1-3alkyl or —O—C1-3alkyl;
- O;
- NRN and S;
- wherein m is 1, 2, 3 or 4, and RN is H or C1-3alkyl;
- R1 is selected from the group consisting of H, C1-6alkyl, C3-6cycloalkyl, —CH2-C3-10cycloalkyl, aryl, —CH2-aryl, and heteroaryl,
- wherein each aryl and heteroaryl group is optionally substituted with 1-3 substituents selected from the group consisting of halogen, —CN, C1-3alkyl and —O—C1-3alkyl;
- R2 is selected from the group consisting of C1-4alkyl, —C(O)OR6, and aryl,
- wherein each alkyl group of R2 is optionally substituted with halogen, cyano, or trimethylsilyl, and wherein R6 is a C1-4alkyl;
- R3 is selected from the group consisting of H, C1-6alkyl, C3-6cycloalkyl,—CH2—C3-10cycloalkyl, aryl, —CH2-aryl, and heteroaryl,
- wherein each aryl and heteroaryl group is optionally substituted with 1-3 substituents selected from the group consisting of halogen,—CN, C1-3alkyl and —O—C1-3alkyl;
- and
- R4 and R5 are each independently of each other selected from the group consisting of H, C1-6alkyl, C3-6cycloalkyl, —CH2—C3-10cycloalkyl, aryl, —CH2-aryl, and heteroaryl,
- wherein each aryl and heteroaryl group is optionally substituted with 1-3 substituents selected from the group consisting of halogen,—CN, C1-3alkyl and —O-C1-3alkyl;
- or a tautomer, stereoisomer or salt thereof.
14 more elements
Dependencies are inferred from the claim text.