US2003171366A1PendingUtilityA1
Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods
Priority: Aug 12, 1999Filed: Jan 10, 2002Published: Sep 11, 2003
Est. expiryAug 12, 2019(expired)· nominal 20-yr term from priority
A61P 31/00A61P 31/04C07D 487/04C07D 471/04C07D 413/10
47
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Claims
Abstract
Bicyclic heterocyclic substituted phenyl oxazolidinone compounds of the formula: wherein Y is a radical of the formulae II or III: in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A compound of Formula I
wherein:
R is selected from the group consisting of OH, O-Aryl, O-Heteroaryl, N 3 , OR′, OSO 2 R″, —NR′″R″″, or
wherein:
(i) R′ is straight-chain or branched acyl having up to 6 carbon atoms or benzyl;
(ii) R″ is straight-chain or branched alkyl, having up to 5 carbon atoms, phenyl or tolyl; and
(iii) R′″ and R″″ are independently selected from the group consisting of H, cycloalkyl having 3 to 6 carbon atoms, phenyl or tert-butoxycarbonyl, fluorenyloxycarbonyl, benzyloxycarbonyl, straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by cyano or alkoxycarbonyl having up to 4 carbon atoms, —CO 2 —R 1 , —CO—R 1 , —CO—SR 1 , —CS—R 1 , P(O)(OR 2 )(OR 3 ), and —SO 2 —R 4 , in which
R 1 is selected from the group consisting of H, cycloalkyl having 3 to 6 carbon atoms, trifluoromethyl or phenyl, benzyl\ or acyl having up to 5 carbon atoms, straight-chain or branched alkyl having up to 6 carbon atoms, said alkyl optionally substituted by straight-chain or branched alkoxycarbonyl having up to 5 carbon atoms, OH, cyano, up to 3 halogen atoms, and —NR 5 R 6 in which R 5 and R 6 are identical or different and are selected from H, phenyl or straight-chain or branched alkyl having up to 4 carbon atoms;
R 2 and R 3 are identical or different and are selected from hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms; and
R 4 is selected from straight-chain or branched alkyl having up to 4 carbon atoms or phenyl and;
R 4a is CN, COR 4c , COOR 4c , CONHR 4c , CO—NR 4c R 4d , SO 2 R 4c , SO 2 NHR 4c , SO 2 —NR 4c R 4d , or NO 2 ;
R 4b is H, alkyl, OR 4c , SR 4c , amino, NHR 4c , NR 4c ,R 4d , (C1-C8), alkylaryl or mono-, di-, tri-, and per-halo(C1-C8) alkyl;
R 4c and R 4d are independently selected from H, alkyl, aryl, or in the case of any NR 4c R 4d group R 4c and R 4d taken together with the nitrogen atom to which they are attached form a unsubstituted or substituted pyrrolidinyl, piperidinyl or morpholinyl group;
X is 0 to 4 members independently selected from the group consisting of halogen, OH, mercapto, nitro, halo-C 1-8 -alkyl, C 1-8 alkoxy, thio-C 1-8 -alkyl, C 1-8 alkyl-amino, di(C 1-8 -alkyl-)amino, formyl, carboxy, alkoxycarbonyl, C 1-8 alkyl-CO—O—, C 1-8 alkyl-CO—NH—, carboxamide, aryl, substituted-aryl, heteroaryl, substituted-heteroaryl, CN, amine, C 3-6 cycloalkyl, C 1-8 alkyl optionally substituted with one or more members selected from the group consisting of F, Cl, OH, C 1-8 alkoxyl and C 1-8 acyloxy; and
Y is a radical of Formulae II or III:
wherein
R 5 , R 6 , R 7 , and R 8 are each independently H, alkyl, CN, nitro, C 1-8 alkyl, halo-C 1-8 -alkyl, formyl, carboxy, alkoxycarbonyl, carboxamide, aryl, substituted-aryl, heteroaryl, or substituted-heteroaryl, or R 5 and R 6 and/or R 7 and R 8 together form an oxo group;
R 9 , and R 10 are each independently H, halogen, alkyl, OH, CN, mercapto, nitro, C 1-8 alkyl, halo-C 1-8 -alkyl, C 1-8 alkoxyl, thio-C 1-8 -alkyl, amino, C 1-8 -alkyl-amino, di(C 1-8 -alkyl-)amino, formyl, carboxy, alkoxycarbonyl, C 1-8 -alkyl-CO—O—, C 1-8 -alkyl-CO—NH—, carboxamide, aryl, substituted-aryl, alkoxy, heteroaryl, substituted-heteroaryl, or amine;
A, B, C, and D are selected from C, S, O, and N to form any five to ten membered aromatic or heteroaromatic ring, said heteroaromatic ring having one to four members selected from the group consisting of S, O, and N;
Z is selected from halogen, alkyl, aryl, substituted-aryl, heteroaryl, substituted-heteroaryl, CN, CHO, COalkyl, amine, (dialkylamino)alkyl where dialkylamino is selected from dimethylamine, diethylamine, morpholinyl, thiomorpholinyl, pyrroidinyl, or piperidinyl, or, alkoxy, or NHCO—(C 1 -C 8 -alkyl); and
m is 0 or 1,
and the pharmaceutically acceptable salts and esters thereof.
2 . The compound of claim 1 wherein Y is selected from the group consisting of
3 . The compound of claim 1 wherein R is —NHCOCH 3 or is selected from the group consisting of
4 . A compound of claim 1 having the formula:
5 . A compound of claim 1 having the formula:
6 . A compound of claim 1 having the formula:
7 . A compound of claim 1 having the formula:
8 . A compound of claim 1 having the formula:
9 . A compound of claim 1 having the formula:
10 . A compound of claim 1 having the formula:
11 . A compound of claim 1 having the formula:
12 . A compound of claim 1 having the formula:
13 . A compound of claim 1 having the formula:
14 . A compound of claim 1 having the formula:
15 . A compound of claim 1 having the formula:
16 . A compound of claim 1 having the formula:
17 . A compound of claim 1 having the formula:
18 . A compound of claim 1 having the formula:
19 . A compound of claim 1 having the formula:
20 . A compound of claim 1 having the formula:
21 . A compound of claim 1 having the formula:
22 . A compound of claim 1 having the formula:
23 . A compound of claim 1 having the formula:
24 . A compound of claim 1 having the formula:
25 . A compound of claim 1 having the formula:
26 . A compound of claim 1 having the formula:
27 . A compound of claim 1 having the formula:
28 . A compound of claim 1 having the formula:
29 . A compound of claim 1 having the formula:
30 . A compound of claim 1 having the formula:
31 . A compound of claim 1 having the formula:
32 . A compound of claim 1 having the formula:
33 . A compound of claim 1 having the formula:
34 . A compound of claim 1 having the formula:
35 . A compound of claim 1 having the formula:
36 . A compound of claim 1 having the formula:
37 . A compound of claim 1 having the formula:
38 . A compound of claim 1 having the formula:
39 . A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.
40 . A method of treating a subject having a condition caused by or contributed to by bacterial infection, which comprises administering to said mammal a therapeutically effective amount of the compound according to claim 1 .
41 . A method of preventing a subject from suffering from a condition caused by or contributed to by bacterial infection, which comprises administering to the subject a prophylactically effective dose of the pharmaceutical composition of a compound according to claim 1 .
42 . The method of claim 40 or 41 wherein said condition is selected from the group consisting of community-acquired pneumonia, upper and lower respiratory tract infections, skin and soft tissue infections, bone and joint infections and hospital-acquired lung infections.
43 . The method of claim 40 or 41 wherein said bacterium is selected from the group consisting of S. aureus, S. epidermidis, S. pneumoniae, S. pyogenes, Enterococcus spp., Moraxella catarrhalis and H. influenzae.
44 . The method of claim 40 or 41 wherein said bacterium is a Gram-positive coccus.
45 . The method of claim 44 wherein said Gram-positive coccus is drug-resistant.Cited by (0)
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