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Publication Number
US-8492414-B2
Publication Date
2013-07-23
Expiration Date
Abstract
Compounds of formula (IA) or (IB) have antibacterial activity: wherein W is ═CH— or ═N—; Ri and R2 are independently selected from hydrogen, fluoro and chloro, provided that Ri and R2 are not each hydrogen when W is ═CH—; n is 0 or 1; X is —O—, —S—, or —CH2—; and Q is (i) a phenyl radical, a naphthyl radical, a monocyclic carbocyclic or heteroaryl radical having 3 to 6 ring atoms, or a bicyclic heteroaryl radical having 5 to 10 ring atoms, any of which radicals being optionally substituted; or (ii) an optionally substituted C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl radical, which may optionally be interrupted by —O—, —S—, —S(O)—, —S(O2)—, —NH—, —N(CH3)—, —N(CH2CH3)—, —C—K═Oh or —C(═O)—O—.
Core Innovation
The invention relates to substituted thiadiazolylmethoxybenzamide and thiadiazolylmethoxypyridylamide compounds of formula (IA) or formula (IB), and salts thereof. The compounds are defined by W being —CH— or —N—, with R1 and R2 independently selected from hydrogen, fluoro and chloro under the proviso that when W is —CH—, R1 and R2 are not each hydrogen. The compounds further include a parameter n being 0 or 1, and a linkage group X being —O—, —S—, or —CH2—.
In the compounds of formula (IA) or (IB), Q is defined broadly as either a phenyl radical, a naphthyl radical, a monocyclic carbocyclic or heteroaryl radical having 3 to 6 ring atoms, or a bicyclic heteroaryl radical having 5 to 10 ring atoms, any of which radicals being optionally substituted; or an optionally substituted C1–C6 alkyl, C2–C6 alkenyl, or C2–C6 alkynyl radical, which may optionally be interrupted by —O—, —S—, —S(O)—, —S(O2)—, —NH—, —N(CH3)—, —N(CH2CH3)—, —C(O)—, or —C(O)O—. The definition includes the use of salts for the claimed compounds.
The disclosed therapeutic concept is use of the antibacterial substituted thiadiazolylmethoxybenzamide/pyridylamide compounds for treating bacterial infection, including bacterial infection caused by Gram-positive pathogens. The document also states utility in connection with methods of treatment and antibacterial pharmaceutical compositions comprising the compounds and pharmaceutically acceptable carriers. The mechanism is described as inhibition of cell division machinery mediated by FtsZ.
Claims Coverage
The document provides one independent claim covering a family of substituted thiadiazolylmethoxybenzamide/thiadiazolylmethoxypyridylamide compounds (or salts) defined by a constrained structural formula with specific selectable substituent classes. The inventive coverage is supported by dependent claims that further narrow structural subsets and include a pharmaceutical composition embodiment.
Substituted thiadiazolylmethoxybenzamide or thiadiazolylmethoxypyridylamide compound of formula (IA)/(IB)
A compound which is a substituted thiadiazolylmethoxybenzamide or thiadiazolylmethoxypyridylamide of formula (IA) or a salt thereof, wherein W is —CH— or —N—; R1 and R2 are independently selected from hydrogen, fluoro and chloro, provided that R1 and R2 are not each hydrogen when W is —CH—; n is 0 or 1; X is —O—, —S—, or —CH2—; and Q is a phenyl radical, a naphthyl radical, a monocyclic carbocyclic or heteroaryl radical having 3 to 6 ring atoms, or a bicyclic heteroaryl radical having 5 to 10 ring atoms, any of which radicals being optionally substituted, or an optionally substituted C1–C6 alkyl, C2–C6 alkenyl, or C2–C6 alkynyl radical, which may optionally be interrupted by —O—, —S—, —S(O)—, —S(O2)—, —NH—, —N(CH3)—, —N(CH2CH3)—, —C(O)—, or —C(O)O—.
Overall claim coverage is concentrated in the structural formula definition for substituted thiadiazolylmethoxybenzamide or thiadiazolylmethoxypyridylamide compounds (including salts), with Q defined across aryl/heteroaryl or optionally substituted interrupted alkyl/alkenyl/alkynyl radicals. Dependent claims refine specific W and R1/R2 patterns, narrow Q to particular pyridyl positions and/or limit optional Q substituents, and also provide a pharmaceutical composition including a pharmaceutically acceptable carrier.
Stated Advantages
Treating bacterial infection.
Inhibiting cell division machinery mediated by FtsZ.
Providing antibacterial pharmaceutical compositions comprising the compounds and a pharmaceutically acceptable carrier.
Documented Applications
Use of the antibacterial substituted thiadiazolylmethoxybenzamide/pyridylamide compounds for treating bacterial infection, including infections by Gram-positive pathogens such as MRSA and resistant S. pneumoniae/Enterococcus faecium.
Methods of treatment are described for treating bacterial infection using the claimed compounds.
Treatment of bacterial contamination of substrates is described.
Antibacterial pharmaceutical compositions comprising the claimed compounds and pharmaceutically acceptable carriers.
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