Putting chirality to work: The strategy of chiral switches

被引:498
作者
Agranat, I
Caner, H
Caldwell, A
机构
[1] Univ London Imperial Coll Sci Technol & Med, Fac Med, Div Biomed Sci, London SW7 2AZ, England
[2] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel
关键词
D O I
10.1038/nrd915
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Most of the new drugs reaching the market today are single enantiomers, rather than the racemic mixtures that dominated up to ten years ago. Many of the new single-enantiomer drugs were developed as such, but there are also important examples of new single-enantiomer drugs derived from 'chiral switches' of established racemates. Indeed, a well-timed chiral switch can offer enhanced therapy and further profitability as a 'line extension' of a major racemic drug with patents that are expiring.
引用
收藏
页码:753 / 768
页数:16
相关论文
共 134 条
[41]  
Eichelbaum M., 1996, ADV DRUG RES, V28, P1, DOI 10.1016/S0065-2490(96)80003-7
[42]  
Eliel E.L., 1994, Stereochemistry of Organic Compounds
[43]   STEREOSPECIFIC DETERMINATION, CHIRAL INVERSION IN-VITRO AND PHARMACOKINETICS IN HUMANS OF THE ENANTIOMERS OF THALIDOMIDE [J].
ERIKSSON, T ;
BJORKMAN, S ;
ROTH, B ;
FYGE, A ;
HOGLUND, P .
CHIRALITY, 1995, 7 (01) :44-52
[44]   RESOLUTION OF THE ENANTIOMERS OF OMEPRAZOLE AND SOME OF ITS ANALOGS BY LIQUID-CHROMATOGRAPHY ON A TRISPHENYLCARBAMOYLCELLULOSE-BASED STATIONARY PHASE - THE EFFECT OF THE ENANTIOMERS OF OMEPRAZOLE ON GASTRIC GLANDS [J].
ERLANDSSON, P ;
ISAKSSON, R ;
LORENTZON, P ;
LINDBERG, P .
JOURNAL OF CHROMATOGRAPHY-BIOMEDICAL APPLICATIONS, 1990, 532 (02) :305-319
[45]  
*EUR PAT OFF, 1977, EUR PAT CONV
[46]   TOXICITY AND TERATOGENICITY OF OPTICAL ISOMERS OF THALIDOMIDE [J].
FABRO, S ;
SMITH, RL ;
WILLIAMS, RT .
NATURE, 1967, 215 (5098) :296-&
[47]   ACID ACTIVATION OF (H+-K+)-ATPASE INHIBITING 2-(2-PYRIDYLMETHYL-SULPHINYL)BENZIMIDAZOLES - ISOLATION AND CHARACTERIZATION OF THE THIOPHILIC ACTIVE PRINCIPLE AND ITS REACTIONS [J].
FIGALA, V ;
KLEMM, K ;
KOHL, B ;
KRUGER, U ;
RAINER, G ;
SCHAEFER, H ;
SENNBILFINGER, J ;
STURM, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (02) :125-127
[48]   Aminorex to fen/phen - An epidemic foretold [J].
Fishman, AP .
CIRCULATION, 1999, 99 (01) :156-161
[49]  
FONTANA SA, 2001, Patent No. 6268385
[50]  
FULLER RW, 1993, Patent No. 5250571