Carboxylic acid derivatives and use thereof in the preparation of prodrugs
AssigneeQingeng Li
InventorsQingeng Li, Tao Wang, Gang Chen, Yuanzhong Wang, Wei Mao, Tong Wu, Lingguo Zeng
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Abstract
The present invention discloses a class of carboxylic acid derivatives and use thereof in preparation of prodrugs. The carboxylic acid derivatives have the general formula (I), wherein R1 is H or alkyl; X is H or F; Y is F or fluoroalkyl; n is 0, 1, 2, 3, 4, 5, or 6; W is W1 or W2; W1 is NR2R3, NR2R3.A, R2 and R3 are each independently H, alkyl, cycloalkyl, or a protecting group for amino; m is 0, 1, 2, or 3; A is an acid; W2 is COOR4, OPO(OR4)2, or PO(OR)2; R4 is H, or a protecting group for carboxyl or hydroxyl in phosphoric acid.
Claims13
A carboxylic acid derivative of general formula (I), (II) or (III):
- wherein,
- R1 is H, methyl, ethyl, n-propyl, or isopropyl;
- X is F;
- Y is H or F;
- n is 1, 2, 3, 4, 5 or 6;
- W is W1;
- W1 is .NR2R3.A or
- R2 is H, C1-C6 alkyl, cyclopentyl, or cyclohexyl;
- R3 is C1-C6 alkyl, cyclopentyl, cyclohexyl, or benzyl;
- m is 0, 1, 2 or 3;
- A is an acid;
- M is a metal ion;
- q is the charge number of M;
- and
- G is Cl, Br or benzenesulfonyloxy optionally substituted with alkyl.
A compound that is selected from the group consisting of:
- 4-N,N-dimethylamino-2(R)-fluorobutyric acid hydrochloride;
- 4-N-isopropylamino-2(R,S)-fluorobutyric acid hydrochloride;
- 4-N,N-diethyl amino-2(R,S)-trifluoromethylbutyric acid hydrochloride;
- 4-N-benzylamino-2,2-difluorobutyric acid hydrochloride;
- 4-N-isobutylamino-2(R,S)-difluoromethylbutyric acid hydrochloride;
- 4-N-(aziridin-1-yl)-2(R,S)-difluoromethylbutyric acid hydrochloride;
- 4-N-(pyrrolidin-1-yl)-2(R,S)-fluorobutyric acid hydrochloride;
- 3-N-benzylamino-2(R,S)-(1,1-difluoromethyl)propionic acid hydrochloride;
- 6-N-cyclohexylamino-2(R,S)-trifluoromethylhexanoic acid hydrochloride;
- 4-benzyloxy-4-oxo-2(R,S)-fluorobutyric acid;
- 5-benzyloxy-5-oxo-2(R)-fluoropentanoic acid;
- 6-benzyloxy-6-oxo-2(S)-fluorohexanoic acid;
- dibenzyl [1-(3-(R,S)-fluoro-3-carboxy)propyl] phosphate triester;
- dibenzyl [1-(5-(S)-fluoro-5-carboxy)pentyl] phosphate triester;
- 4-(dibenzyloxy)phosphoryl-2(R,S)-fluorobutyric acid;
- 5-(dibenzyloxy)phosphoryl-2(R)-fluoropentanoic acid;
- 4-benzyloxy-4-oxo-2(R,S)-fluorobutyryl chloride;
- sodium 5-benzyloxy-5-oxo-2(R)-fluorovalerate;
- dibenzyl [1-(3-(R,S)-fluoro-4-oxo-4-chloro)butyl] phosphate triester;
- dibenzyl [potassium 1-(4-(S)-fluoro-5-carboxylate)pentyl] phosphate triester;
- 4-(dibenzyloxy)phosphoryl-2(R,S)-fluorobutyryl chloride;
- sodium 4-N,N-dimethylamino-2(R,S)-fluorobutyrate;
- calcium 4-N,N-diethyl amino-2(R,S)-fluorobutyrate;
- aluminum 3-N-b enzylamino-2(R,S)-benzyloxypropionate;
- 4-N,N-dimethylamino-2(R,S)-fluorobutyryl chloride hydrochloride;
- 4-N-benzylamino-2,2-difluorobutyryl chloride hydrochloride;
- 4-N,N-dimethylamino-2(R,S)-fluorobutyric acid;
- and
- 4-N,N-dimethylamino-2(S)-fluorobutyric acid hydrochloride.
Dependencies are inferred from the claim text.