US2008090816A1PendingUtilityA1
Anti-infective biaryl compounds
Assignee: GENESOFT PHARMACEUTICALS INCPriority: Oct 25, 2002Filed: Aug 2, 2007Published: Apr 17, 2008
Est. expiryOct 25, 2022(expired)· nominal 20-yr term from priority
C07D 473/00C07D 487/04C07D 409/14C07D 403/14A61P 31/04C07D 401/14C07D 471/04
60
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Claims
Abstract
Compounds represented by the formula where R 1 , R 2 , R 3 , R 4 , R 5 , and Q are as defined herein, exhibit activity against infectious pathogens.
Claims
exact text as granted — not AI-modified1 . A compound according to formula (I)
and the solvates, prodrugs, and pharmaceutically acceptable salts thereof, wherein
Ar is an unsubstituted or substituted phenyl group, 5-member heteroaryl group, 6-member heteroaryl group, 6,6-condensed ring aryl or heteroaryl group, or 6,5-condensed ring heteroaryl group;
each Q is independently N, CH, C(R 6 ), where R 6 is as defined hereinbelow, with the proviso that no more than two Q's are N;
each of R 1 , R 2 , R 3 , and R 4 independently is H or a (C 1 -C 5 ) alkyl group;
each R 5 is independently H, a substituted or unsubstituted (C 1 -C 12 )alkyl group, or a substituted or unsubstituted (C 1 -C 12 ) heteroalkyl group; and
each R 6 is independently a substituted or unsubstituted (C 1 -C 12 ) alkyl, OR 5 , N(R 5 ) 2 , O(CO)R 5 , N(CO)R 5 , Cl, F, or Br.
2 . A compound according to claim 1 , represented by the formula (II)
3 . A compound according to claim 1 , wherein Ar is an unsubstituted or substituted phenyl, imidazolyl, pyrrolyl, pyrazolyl, furanyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, furazanyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, thienyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, quinolyl, isoquinolyl, benzothienyl, indolyl, or benzofuranyl group.
4 . A compound according to claim 1 , wherein Ar is selected from the group consisting of
5 . A compound according to claim 1 , wherein the 6,5-condensed ring system
is selected from the group consisting of
6 . A compound according to claim 1 , wherein in the 6,5-condensed ring system
at least one Q is N
7 . A compound according to claim 1 , represented by the formula (III):
8 . A compound according to claim 1 , represented by the formula (IV):
9 . A compound according to claim 1 , represented by the formula (V):
10 . A compound according to claim 1 , represented by the formula (VI):
11 . A compound according to claim 1 , represented by the formula (VII):
12 . A compound according to claim 1 , wherein each of R 1 , R 2 , and R 3 is H.
13 . A compound according to claim 1 , wherein R 4 is methyl.
14 . A compound according to claim 1 , wherein R 5 is methyl, ethyl, propyl, isopropyl, (CH 2 ) n (Am), or (CH 2 ) n (OH), where n is 2, 3, 4, or 5 and Am is an alkyl amine group or a quaternary ammonium group.
15 . A compound according to claim 14 , wherein R 5 is (CH 2 ) 3 (Am).
16 . A compound according to claim 14 , wherein R 5 is selected from the group consisting of
17 . A compound according to claim 1 , wherein R 5 is methyl, Ar is
and in the condensed 6,5 ring system
at least one Q is N and the remaining Q's are CH.
18 . A compound according to claim 1 , wherein Ar is selected from the group consisting of
and R 5 is (CH 2 ) 3 N(CH 3 ) 2 .
19 . A compound according to claim 1 , wherein R 6 is methyl, ethyl, propyl, isopropyl, OR 5 , NH(CO)R 5 , O(CO)R 5 , N(R 5 ), or Cl.
20 . A compound according to claim 1 , wherein R 6 is selected from the group consisting of:
21 . A compound according to claim 1 , having a minimum inhibitory concentration of 4 μg/mL or less against at least one of Staphylococcus aureus (ATCC 27660), Streptococcus pneumoniae (ATCC 51422), and Enterococcus faecium (ATCC 51559).
22 . A method of treating a bacterial infection in a mammal, comprising administering to a patient in need of such treatment an effective amount of a compound according to claim 1 .
23 . A method according to claim 22 , wherein the bacterial infection is an infection by drug resistant bacteria.
24 . A method according to claim 23 , wherein the drug resistant bacteria is MRSA, PRSP, or VRE.
25 . The use of a compound according to claim 1 for the preparation of a medicament for the treatment of a bacterial infection in a mammal.Cited by (0)
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