SYNTHESIS, IN-VITRO AND IN-VIVO ANTIBACTERIAL ACTIVITY OF 7-(7-METHYL-2,5-DIAZABICYCLO[2.2.1]HEPTANE)NAPHTHYRIDONE DERIVATIVES AS ANALOGS OF BMY 40062

被引:6
作者
REMUZON, P [1 ]
BOUZARD, D [1 ]
CLEMENCIN, C [1 ]
DUSSY, C [1 ]
JACQUET, JP [1 ]
FUNGTOMC, J [1 ]
KESSLER, RE [1 ]
机构
[1] BRISTOL MYERS SQUIBB PHARMACEUT RES & DEV DIV,WALLINGFORD,CT 06492
关键词
QUINOLONES; NAPHTHYRIDINES; ANTIBACTERIAL ACTIVITY; METHYL BRIDGED PIPERAZINES;
D O I
10.1016/0223-5234(93)90013-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis and the antimicrobial activities of chiral (1R,4R,7S)- and (1S,4S,7S)-[7-methyl-2,5-diazabicyclo[2.2.1]-heptan-2-yl] analogs of BMY 40062 are reported. The new derivatives have been found to be less active in vitro but as active in vivo (im) than BMY 40062. The IR,4R,7S substituent seems promising for the design of powerful new antibiotics.
引用
收藏
页码:455 / 461
页数:7
相关论文
共 10 条
[1]  
Andriole V., 1988, QUINOLONES
[2]   FLUORONAPHTHYRIDINES AND QUINOLONES AS ANTIBACTERIAL AGENTS .2. SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NEW 1-TERT-BUTYL 7-SUBSTITUTED DERIVATIVES [J].
BOUZARD, D ;
DICESARE, P ;
ESSIZ, M ;
JACQUET, JP ;
KIECHEL, JR ;
REMUZON, P ;
WEBER, A ;
OKI, T ;
MASUYOSHI, M ;
KESSLER, RE ;
FUNGTOMC, J ;
DESIDERIO, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1344-1352
[3]   FLUORONAPHTHYRIDINES AND QUINOLONES AS ANTIBACTERIAL AGENTS .1. SYNTHESIS AND STRUCTURE ACTIVITY RELATIONSHIPS OF NEW 1-SUBSTITUTED DERIVATIVES [J].
BOUZARD, D ;
DICESARE, P ;
ESSIZ, M ;
JACQUET, JP ;
REMUZON, P ;
WEBER, A ;
OKI, T ;
MASUYOSHI, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) :537-542
[4]  
FINNEY DJ, 1971, STATISTICAL METHODS, P524
[5]   INVITRO AND INVIVO ANTIBACTERIAL ACTIVITIES OF BMY-40062, A NEW FLUORONAPHTHYRIDONE [J].
FUNGTOMC, J ;
DESIDERIO, JV ;
TSAI, YH ;
WARR, G ;
KESSLER, RE .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1989, 33 (06) :906-914
[6]   SYNTHESIS OF 3,4-DIHYDROXYPROLINES .2. SYNTHESIS, STEREOCHEMISTRY AND REACTIVITY OF SOME 3,4-EPOXY-D,L-PROLINE DERIVATIVES [J].
HUDSON, CB ;
ROBERTSON, AV ;
SIMPSON, WRJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (11) :2479-2498
[7]  
JORDIS U, 1990, SYNTHESIS-STUTTGART, V10, P925
[8]   COMPARISON OF A NEW CEPHALOSPORIN, BMY 28142, WITH OTHER BROAD-SPECTRUM BETA-LACTAM ANTIBIOTICS [J].
KESSLER, RE ;
BIES, M ;
BUCK, RE ;
CHISHOLM, DR ;
PURSIANO, TA ;
TSAI, YH ;
MISIEK, M ;
PRICE, KE ;
LEITNER, F .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1985, 27 (02) :207-216
[9]   FLUORONAPHTHYRIDINES AS ANTIBACTERIAL AGENTS .6. SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NEW CHIRAL 7-(1, 3, 4, AND 6-METHYL-2,5-DIAZABICYCLO[2.2.1]HEPTAN-2-YL)NAPHTHYRIDINE ANALOGS OF 7-[(1R,4R)-2,5-DIAZABICYCLO[2.2.1]HEPTAN-2-YL]-1-(1,1-DIMETHYLETHYL)-6-FLUORO-1,4-DI-HYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID - INFLUENCE OF THE CONFIGURATION ON BLOOD-PRESSURE IN DOGS - A QUINOLONE-CLASS EFFECT [J].
REMUZON, P ;
BOUZARD, D ;
GUIOL, C ;
JACQUET, JP .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (15) :2898-2909
[10]  
REMUZON P, 1993, IN PRESS J HETEROCYC