Following is one of the patent documents most requested by researchers using CAS electronic products.
|
CAS indexed 261 chemical substances from this document.
CAS subject entries for this document include: Infection; Antibacterial agents; Tuberculostatics; and 18 additional concepts. | |
CAPLUS COPYRIGHT 2007 ACS on STN
| TITLE:
| Phenyl-substituted oxazolidinone derivatives and their preparation, pharmaceutical compositions, and use as antimicrobials |
| INVENTOR(S):
| Das, Biswajit; Ahmed, Shahadat; Yadav, Ajay Singh; Ghosh, Soma; Gujrati, Arti; Sharma, Pankaj; Rattan, Ashok |
| PATENT ASSIGNEE(S):
| Ranbaxy Laboratories Limited, India |
| SOURCE:
| PCT Int. Appl., 145 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- -------------------- --------
WO 2006038100 A1 20060413 WO 2005-IB2971 20051006
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH,
CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD,
GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ,
LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ,
NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG,
SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN,
YU, ZA, ZM, ZW
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE,
IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ,
CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH,
GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY,
KG, KZ, MD, RU, TJ, TM
ABSTRACT:
The invention relates to phenyl-substituted oxazolidinones I, or their pharmaceutically acceptable salts, solvates, esters, enantiomers, diastereomers, N-oxides, polymorphs, prodrugs, or metabolites, as well as processes for their synthesis. In compds. I: A is pyridine-2,5-diyl, pyrimidine-2,5-diyl, furan-2,5-diyl, thiophene-2,5-diyl, and analogs; U and V are independently selected from H (both U and V cannot be H), lower alkyl, or halo; R is CH:NORf, CH:NOC(O)Rf, CH:NOSORf, CH:NOC(O)NHRf, heterocyclyl, or heteroaryl; Rf is H, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, aralkyl, heteroaryl, heterocyclyl, heteroarylalkyl, or heterocyclylalkyl; R1 is azido, NCS, NHYRf, NRjC(:T)NRfRq, NRfRq, NRj(C:O)ORs; Y is (C:O), (C:S), or SO2; T is O, S, N(CN), N(NO2), CH(NO2); Rj is H, alkyl, alkenyl, cycloalkyl, aryl, aralkyl, heterocyclyl, heteroaryl, heteroarylalkyl, or heterocyclylalkyl; Rq is H, alkyl, cycloalkyl, aryl, aralkyl, heteroaryl, heterocyclyl, heteroarylalkyl or heterocyclylalkyl; Rs is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heteroarylalkyl or heterocyclylalkyl; with the proviso that: when U is H, V is F, R is NHCOCH3 and A is pyridine-2,5-diyl, then R is a 5-membered heteroaryl ring contg. two or four N atoms (wherein the 5-membered heteroaryl ring contg. four N atoms is linked through an N-atom to pyridine-2,5-diyl and is always substituted); when A is pyrimidine-2,5-diyl and U, V, and R1 are as defined above then R cannot be a 5-membered heterocyclyl ring contg. 2 hetero atoms. The invention also relates to pharmaceutical compns. contg. I as antimicrobials. I are useful antimicrobial agents (no data), effective against a no. of human and veterinary pathogens, including gram-pos. aerobic bacteria (for example, multiple-resistant staphylococci, streptococci, and enterococci), as well as anaerobic organisms (for example, Bacteroides spp. and Clostridia spp.), and acid fast organisms (for example, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.). Approx. 100 compds. I were prepd., and are claimed by name. The synthesis of most compds. I and a variety of intermediates is described. For instance, 5-bromopyridin-2-amine was (1) N-protected with BOC, followed by (2) conversion of the bromide to the boronic acid, (3) Pd-catalyzed coupling of the boronic acid with (S)-N-[[3-(4-iodo-3,5-difluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide, (4) N-deprotection with HCl, and (5) cyclization of the freed amine with 2,5-dimethoxytetrahydrofuran-3-carboxaldehyde, to give invention compd. II. I have good activity against multiply resistant Gram-pos. pathogens like methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococci (VRE), and Streptococcus pneumoniae. Some I have activity against multiple drug-resistant tuberculosis (MDR-TB) strain, while others have significant activity against important anaerobic bacteria. I are also active against MAI sirens and Gram-neg. pathogens like Moraxella catarrhalis and Haemophilus influenza.
Updated 5/15/2007 1:30:24 PM
