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US 2024/0199677 A1Published application
Glycosyltransferase inhibitors
AssigneesCalifornia Institute of Technology, University of Tennessee Fresearch Foundation
InventorsWilliam M. Clemons, Michio Kurosu
Life of this patent
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Abstract
The present invention relates to methods of treating bacterial infections and cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of at least one compound provided herein.
Claims17
A compound of Formula I:
- or a pharmaceutically acceptable salt thereof;
- wherein
- R1 is piperazine-O-Ph-O-CF3, piperazine-O-Ph-CF3 or C7 alkyl;
- R2 is H or CH3;
- X is absent
- Y is absent or —(CH2)n—;
- and
- n is 1, 2, or 3.
5 more elements
A process for preparing a compound of Formula III:
- comprising reacting a compound of Formula II:
- with a copper reagent in the presence of a solvent and a base, and further reacting the compound of Formula II with a protecting group reagent;
- wherein
- R2 is H or CH3;
- PG is a protecting group selected from the group consisting of acetyl (Ac), benzyl (Bn), tert-butyloxycarbonyl (Boc), benzoyl (Bz), carboxybenzyl (Cbz), carbamoyl, 3,4-dimethoxy-benzyl (DMPM), 9-fluorenylmethyloxycarbonyl (Fmoc), p-methoxybenzyl carbonyl (Moz), 4-nitrobenzylsulfonyl (Nos), p-methoxybenzyl (PMB), p-methoxyphenyl (PMP), 4-toluenesulfonyl (Tos), and 2,2,2-trichloroethoxycarbonyl trichloroethyl chloroformyl (Troc);
- and
- the copper reagent is selected from the group consisting of CuSO4, Cu(OAc)2, and CuCl2.
4 more elements
The process for preparing a composition comprising a compound of Formula V:
- comprising reacting a compound of Formula III:
- with a compound of Formula IV:
- under basic conditions in a solvent;
- wherein
- R2 is H or CH3;
- PG is a protecting group selected from the group consisting of acetyl (Ac), benzyl (Bn), tert-butyloxycarbonyl (Boc), benzoyl (Bz), carboxybenzyl (Cbz), carbamoyl, 3,4-dimethoxy-benzyl (DMPM), 9-fluorenylmethyloxycarbonyl (Fmoc), p-methoxybenzyl carbonyl (Moz), 4-nitrobenzylsulfonyl (Nos), p-methoxybenzyl (PMB), p-methoxyphenyl (PMP), 4-toluenesulfonyl (Tos), and 2,2,2-trichloroethoxycarbonyl trichloroethyl chloroformyl (Troc);
- and
- R3 is selected from the group consisting of OC1-C4 alkyl, tosylate, mesylate, iodo, bromo, chloro, imidazolyl, and triflate.
5 more elements
The process for preparing a composition comprising a compound of Formula I:
- comprising treating a compound of Formula V:
- with an acid in a solvent;
- wherein:
- R1 is piperidinepiperidinyl-O-Ph, wherein Ph is optionally substituted with C1-C4 alkyl or OC1-C4 alkyl, wherein OC1-C4 alkyl is optionally further substituted with 1, 2, or 3 halo;
- R2 is H or CH3;
- X is absent;
- Y is —(CH2)n—;
- PG is a protecting group selected from the group consisting of acetyl (Ac), benzyl (Bn), tert-butyloxycarbonyl (Boc), benzoyl (Bz), carboxybenzyl (Cbz), carbamoyl, 3,4-dimethoxy-benzyl (DMPM), 9-fluorenylmethyloxycarbonyl (Fmoc), p-methoxybenzyl carbonyl (Moz), 4-nitrobenzylsulfonyl (Nos), p-methoxybenzyl (PMB), p-methoxyphenyl (PMP), 4-toluenesulfonyl (Tos), and 2,2,2-trichloroethoxycarbonyl trichloroethyl chloroformyl (Troc);
- and
- n is 1.
7 more elements
Dependencies are inferred from the claim text.