WO2014173904A1 - Composé à activité antibactérienne - Google Patents

Composé à activité antibactérienne Download PDF

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WO2014173904A1
WO2014173904A1 PCT/EP2014/058149 EP2014058149W WO2014173904A1 WO 2014173904 A1 WO2014173904 A1 WO 2014173904A1 EP 2014058149 W EP2014058149 W EP 2014058149W WO 2014173904 A1 WO2014173904 A1 WO 2014173904A1
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group
optionally substituted
membered
alkyl
aryl
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PCT/EP2014/058149
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Han REMAUT
Alvin Lo
Gabriel Waksman
David Selwood
Paul Gane
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Vib Vzw
Vrije Universiteit Brussel
Ucl Business Plc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to compounds and their uses.
  • it concerns heterocyclic compounds that inhibit the biogenesis of adhesive pili in Gram- negative bacteria, and their use in the prevention or treatment of conditions arising from colonisation by bacterial pathogens.
  • Gram-negative bacteria possess a wide variety of proteinaceous structures on their surfaces. These include flagella, responsible for cell motility; injectosomes, thin needles that inject effector molecules into host cells; curli, involved in adhesion to surfaces and bio film formation; and pili (or fimbriae), a broad category which encompasses a range of different structures and functions (Fronzes et al, EMBO J 2008, 27:2271-2280; Erhardt et al, Cold Spring Harb Perspect Biol 2010, 2:a000299; Epstein et al, Cell Microbiol 2008, 10: 1413-1420; Ayers et al, Future Microbiol 2010, 5: 1203-1218; and Craig et al, Curr Opin Struct Biol 2008, 18:267- 277).
  • flagella responsible for cell motility
  • injectosomes thin needles that inject effector molecules into host cells
  • curli involved in adhesion to surfaces and bio film formation
  • pili or fimbria
  • pili In pathogenic bacterial species, pili are often crucial virulence factors, determining establishment and persistence of infection. Pili mediate bacterial attachment and invasion of host cells and tissues, and are involved in evasion of host immune systems and/or in biofilm formation. In these pathogenic bacteria, the genetic disruption of pilus formation seriously compromises or abolishes their ability to cause infection. As a result, there is great interest in understanding their structure and mechanism of assembly, since they represent an attractive target for the development of new therapeutics (Durand et al, Infect Disord Drug Targets 2009, 9:518-547; and Cusumano et al, IDrugs 2009, 12:699-705).
  • Pili can be categorised into five major classes depending on the biosynthetic pathway involved: (i) chaperone-usher pili (CU pili), (ii) curli, (iii) type IV pili, (iv) the type III secretion needle, and (v) type IV secretion pili. Of these five classes, CU pili are the most common and most well characterised. CU pili are assembled at the outer membrane by two proteins, a periplasmic chaperone and an outer-membrane, pore-forming protein called the usher (Sauer et al, Biochim Biophys Acta 2004, 1694:259-267).
  • the chaperone facilitates folding of pilus subunits (Barnhart et al, Proc Natl Acad Sci 2000, 97:7709-7714), prevents them from polymerising in the periplasm, and targets them to the usher (Dodson et al, Proc Natl Acad Sci 1993, 90:3670- 3674; and Thanassi et al., Proc Natl Acad Sci 1998, 95:3146-3151).
  • the usher acts as an assembly platform, recruiting chaperone-subunit complexes from the periplasm and coordinating their assembly into a non-covalent polymer that is translocated to the extracellular surface of the bacterium through the usher pore.
  • type 1 pili are implicated in bacterial adherence to the human bladder epithelium and the gastrointestinal tract by binding terminal D-mannose residues on high mannose glycoprotein receptors.
  • type 1 pili are known to mediate bio film formation on non- biological materials such as plastics and steel. As such, they have been proven to be a prime virulence factor in the establishment and persistence of E. co //-caused urinary tract infections (UTIs).
  • UTIs E. co //-caused urinary tract infections
  • target type 1 pili (i) D-mannosides which function as inhibitory receptor analogs (e.g., Han et al., J Med Chem 2012, 55:3945-3959), and (ii) pilicides which work by inhibiting subunit recruitment from the periplasm to the pilus assembly platform in the outer membrane (Aberg et al., Org Biomol Chem 2007, 5: 1827-1834; Pinkner et al, Proc Natl Acad Sci USA 2006, 103: 17897-902).
  • D-mannosides which function as inhibitory receptor analogs
  • pilicides which work by inhibiting subunit recruitment from the periplasm to the pilus assembly platform in the outer membrane
  • D-mannosides have been most extensively studied, including the evaluation of orally delivered D-mannosides by means of in vivo mouse trials (Klein et al., J Med Chem 2010, 53:8627-8641; Cusumano et al., Sci Transl Med 2011, 3: 109ral l5) and in the prevention of catheter-associated UTIs (Guiton et al., Antimicrob Agents Chemother 2012, 56:4738-45).
  • D-mannosides and pilicides due to their mode of action, there are significant limitations to the use of D-mannosides and pilicides.
  • D-mannosides function by preventing the adhesion of uropathogenic E. coli (UPEC) to urothelial cell surfaces by means of the lectin FimH, which is located at the tip of bacterial type 1 pili. Therefore, since D-mannosides are potential ligands for all mannose receptors of the human host system, the lack of target selectivity of these antagonists poses a significant concern. Given that mammalian mannose receptors are present on many tissues throughout the body and are involved in a number of important biological processes, non-selective interactions of such antagonists could potentially have a major impact on these processes and could cause harmful side-effects.
  • UPEC uropathogenic E. coli
  • one provision of current applications is the inclusion of the disclosed pilus biogenesis inhibitors in catheter plastics for the prevention of catheter- associated UTIs.
  • D-mannosides when incorporated in catheter plastic, lead to the risk of opposing effects such as enrichment of type-1 piliated bacteria.
  • pilicides target the interaction between chaperone-subunit complexes and the N- terminal domain of the usher at the periplasmic side of the outer membrane.
  • Pilicides by blocking chaperone and usher functions, therefore have the potential to inhibit pili formation in a broad spectrum of pathogenic bacteria, and thus prevent critical host-pathogen interactions necessary for many diseases.
  • pilicides have not been described to dissociate preformed pili. Instead, they only prevent pilus formation (Pinkner et al., Proc Natl Acad Sci USA 2006, 103: 17897-902).
  • pilicides have shown apparently pleiotropic effects in non-related biosynthesis pathways (Cegelski et al, Nat Chem Biol 2009, 5:913-9), suggesting a poor target specificity and potential problems with toxicity.
  • CU pili-mediated bacterial infections Such therapeutics have the potential to prevent or treat medical conditions associated with CU pili-mediated bacterial infections, either by direct therapeutic treatment (e.g. drug administration), or by their use to prevent adherence and/or colonisation of bacterial pathogens on medical devices employed in a number of medical procedures.
  • the present inventors have found a set of structurally distinct compounds that exhibit a novel mode of action in targeting CU pilus assembly.
  • the result of this new targeting mechanism is that the biogenesis of new pili is prevented, or pre-existing pili are removed from the bacterial surface.
  • these compounds are proposed to function by inhibiting the pilus subunit polymerization step during type 1 pilus assembly, thereby preventing the formation of type 1 pili on the bacterial surface.
  • they have been found to potentially efface pre-assembled pili from the bacterial cell surface.
  • the prospective utility of such compounds is particularly wide-ranging and includes, but is by no means limited to, (i) the non-antibiotic treatment and prophylaxis of human urinary tract infections caused by bacterial pathogens such as E. coli (e.g. in a hospital environment: catheterised patients who are susceptible to recurrent infections), (ii) the prevention of bacterial biofilm formation on medical devices, primarily urinary catheters, as a means to reduce the risk of catheter-associated infections, and (iii) the inhibition of type 1 pilus formation in adherent invasive bacterial strains, for example those associated with Peyer's patch attachment in colitis.
  • bacterial pathogens such as E. coli
  • the prevention of bacterial biofilm formation on medical devices primarily urinary catheters, as a means to reduce the risk of catheter-associated infections
  • the inhibition of type 1 pilus formation in adherent invasive bacterial strains for example those associated with Peyer's patch attachment in colitis.
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6- or 5- membered aryl, heterocyclyl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl or heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted
  • Ci_6 alkyl group an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or -N(R-i)-.
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6- membered cycloalkenyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • the molecular target of the disclosed compounds is believed to be a defined hydrophobic pocket on the chaperone:subunit complexes, referred to as the P5 pocket (Remaut et al., Mol Cell 2006, 2:831-42). Accessibility of this pocket may be a determining factor in the initiation and progression of subunit polymerisation during pilus assembly (Remaut et al., Mol Cell 2006, 2:831-42; Verger et al, EMBO Rep 2006, 7: 1228-32; Verger et al, Structure 2008, 16: 1724- 31).
  • This principle may be conserved throughout chaperone-usher pilus systems such that compounds targeting accessibility of the pocket can be expected to have an inhibitory effect in pilus biogenesis of chaperone-usher pili other than the type 1 pilus system.
  • the molecular principle is conserved, the detailed 3-dimensional structural landscape of the pocket can differ between different subunits and chaperone-usher pilus systems. Specificity and tuning towards different chaperone-usher pilus systems can be attained by chemical modification of the specific chemical entity.
  • the compounds of formula (I) have been found to represent novel, virulence-targeted inhibitors that target CU pilus subunits, thereby inhibiting pilus subunit polymerisation during a process called 'donor-strand exchange' (DSE).
  • DSE 'donor-strand exchange'
  • the structure and mechanism of chaperone- assisted pilus assembly via DSE is well-known in the art, and reference is made, for example, to Sauer et al, Cell 2002, 111 :543-51 and Remaut et al, Mol Cell 2006, 22:831-42.
  • Anti-virulence drugs disarm pathogens rather than killing them. In this way, these drugs prevent a disease by neutralising virulence factors, the specific proteins or toxins that a pathogen uses to establish an infection.
  • Anti-virulence therapy is a particularly advantageous strategy since it minimises selective pressure that perpetuates drug resistance through horizontal gene transfer, resulting in slowing down the rate of resistance evolution.
  • anti-virulence therapeutics leave the commensal microbiota untouched, unlike the broad-acting bacteriostatic or bacteriolytic antibiotics commonly in use.
  • Ci_ 6 alkyl refers to a linear or branched saturated hydrocarbon group containing from 1 to 6 carbon atoms.
  • Examples of Ci_ 6 alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n- pentyl, isopentyl, neopentyl, hexyl, and isohexyl.
  • Ci_ 6 alkylene groups include methylene, ethylene, propylene, butylene, pentylene, and hexylene.
  • C 2 _ 6 alkenyl groups include ethenyl, 1-propenyl, 2-propenyl, 2-methyl-l-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 4-methyl-3-pentenyl, 1-hexenyl, 3-hexenyl, and 5-hexenyl.
  • C x _ y alkynyl' refers to a divalent hydrocarbon group containing one or more carbon-carbon triple bonds and having from x to y carbon atoms.
  • Examples of C 2 _ 6 alkynyl groups include ethynyl, propynyl, butynyl and pentynyl.
  • Ci_ 6 alkoxy groups include methoxy, ethoxy, propoxy, iso- propoxy, butoxy, tert-butoxy, pentoxy and hexoxy.
  • 'x- to y-membered cycloalkyl' refers to a saturated monocyclic hydrocarbon ring of x to y carbon atoms.
  • 3- to 6-membered cycloalkyl refers to a saturated monocyclic hydrocarbon ring of 3 to 6 carbon atoms.
  • 3- to 6-membered cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • 'x- to y-membered cycloalkenyl' refers to a monocyclic hydrocarbon ring containing one or more carbon-carbon double bonds of x to y carbon atoms.
  • C 3 _6 cycloalkenyl refers to an unsaturated monocyclic hydrocarbon ring of 3- to 6-carbon atoms.
  • Examples of C 3 _ 6 cycloalkenyl groups include 2-cyclopenten-l-yl, 3-cyclopenten-l-yl, 2- cyclohexen- 1 -yl, and 3-cyclohexen- 1 -yl.
  • 'aryl' refers to a 5- to 6-membered monocyclic hydrocarbon ring containing x to y carbon atoms, wherein the ring is aromatic.
  • An example of such an aryl group is phenyl.
  • the term 'C x _ y aryl' as used herein refers to a monocyclic or bicyclic ring containing from x to y carbon atoms, wherein at least one ring is aromatic.
  • C 6 -i4 aryl groups include phenyl, naphthyl, tetrahydronaphthalenyl, anthryl, phenanthryl, acenaphthylenyl, biphenylyl, anthracenyl, phenanthrenyl, and phenalenyl.
  • heteroaryl' refers to a 5- to 6-membered monocyclic aromatic ring in which the monocyclic ring contains 1 to 4 heteroatoms selected from oxygen, nitrogen, and sulphur.
  • monocyclic aromatic rings include thienyl, furyl, furazanyl, pyrrolyl, triazolyl, tetrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyranyl, pyrazolyl, pyrimidyl, pyridazinyl, pyrazinyl, pyridyl, triazinyl, and tetrazinyl.
  • heterocyclyl refers to a 5- to 6-membered monocyclic ring which may be saturated or partially unsaturated, in which the monocyclic ring contains 1 to 4 heteroatoms selected from oxygen, nitrogen, and sulphur.
  • Examples of such monocyclic rings include aziridinyl, oxiranyl, pyrrolidinyl, azetidinyl, pyrazolidinyl, oxazolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, hydantoinyl, valerolactamyl, oxiranyl, oxetanyl, dioxolanyl, dioxanyl, oxathiolanyl, oxathianyl, dithianyl, dihydrofuranyl, tetrahydrofuranyl, dihydropyranyl, tetrahydropyranyl, tetrahydropyridinyl, tetrahydropyrimidinyl, tetrahydrothiophenyl, tetrahydrothiopyranyl, diazepanyl and azepanyl.
  • 'amino' refers to an organonitrogen compound with the connectivity - N(R')(R"), where R' and R" are each independently a hydrogen or an optional substituent as defined below in relation to formula (I).
  • Ci_ 6 alkyl carbonyl groups examples include ethanoyl, propanoyl, butanoyl, pentanoyl, and hexanoyl.
  • Ci_ 6 alkyl carbonyl groups include ethyl oxycarbonyl, propyl oxycarbonyl, butyl oxycarbonyl, pentyl oxycarbonyl, and hexyl oxycarbonyl.
  • 'oxycarbonyl' as used herein refers to a single oxycarbonyl group of the formula: -OC(O)-.
  • Ci_ 6 alkyl carbonyloxy groups include ethanoate, propanoate, butanoate, pentanoate, and hexanoate.
  • 'carbonyloxy' as used herein refers to a single carbonyloxy group of the formula: -C0 2 -.
  • C x _ y alkyl carbamoyl' refers to an alkyl group wherein C x _ y alkyl is as defined herein and at least one methylene group (i.e. -CH 2 -) is replaced with an amide group (e.g. -C(0)NR-, where R is a hydrogen atom, a 5- or 6-membered heterocyclyl group, a 5- or 6- membered heteroaryl group, a 3- to 6-membered cycloalkyl group, a Ci_ 6 alkyl group, a Ci_ 6 alkoxy group, or a C 6-14 aryl group, preferably a hydrogen atom).
  • amide group e.g. -C(0)NR-, where R is a hydrogen atom, a 5- or 6-membered heterocyclyl group, a 5- or 6- membered heteroaryl group, a 3- to 6-membered cycloalkyl group, a Ci_ 6 alkyl group, a Ci_
  • Ci_ 6 alkyl carbamoyl groups include ethyl carbamoyl, propyl carbamoyl, butyl carbamoyl, pentyl carbamoyl, and hexyl carbamoyl.
  • the term 'carbamoyl' as used herein refers to a single carbamoyl group of the formula: -C(0)NR-, where R is as defined above.
  • C x _ y alkyl carbamate' refers to an alkyl group wherein C x _ y alkyl is as defined herein and at least one methylene group (i.e. -CH 2 -) is replaced with a carbamate group (e.g. -OC(0)NR-, where R is a hydrogen atom, a 5- or 6-membered heterocyclyl group, a 5- or 6-membered heteroaryl group, a 3- to 6-membered cycloalkyl group, a Ci_ 6 alkyl group, a Ci_ 6 alkoxy group, or a C 6-14 aryl group, preferably a hydrogen atom).
  • a carbamate group e.g. -OC(0)NR-, where R is a hydrogen atom, a 5- or 6-membered heterocyclyl group, a 5- or 6-membered heteroaryl group, a 3- to 6-membered cycloalkyl group, a Ci_ 6 alkyl group,
  • Ci_ 6 alkyl carbamate groups include ethyl carbamate, propyl carbamate, butyl carbamate, pentyl carbamate, and hexyl carbamate.
  • the term 'carbamate' as used herein refers to a single carbamate group of the formula: -OC(0)NR-, where R is as defined above.
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -0-, -N(R 3 )-, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_ 6 alkyl carbamoyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6-membered heterocyclyl or aryl group.
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S.
  • Xi, X 2 , and X 3 are each independently selected from CR 5 R 5 , CR 5 , O, N, NR7, and S, and at least one is selected from O, N, NR7, and S, the possibility of CR 5 R 5 or CR 5 , and NR7 or N depending on the degree of saturation of ring B,
  • R 5 , 5, and R7 are each independently a hydrogen atom, an optionally substituted Ci_6 alkyl group, or an optionally substituted Ci_ 6 alkyl carbonyloxy group.
  • Xi is selected from O, N, and S, and X 2 and X 3 are both N.
  • V is -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group.
  • W is a bond, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, or a carbamoyl group.
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group.
  • ring A is an optionally substituted 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing 3 heteroatoms selected from O, N, and S;
  • Y is a -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond
  • Y is -S-
  • Z is a Ci_6 alkyl carbamoyl group
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group;
  • ring A is an optionally substituted 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing from 3 heteroatoms selected from O, N, and S;
  • Y is a -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6 -i4 aryl group;
  • W is a carbamoyl group
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group;
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a pharmaceutical composition comprising a compound of the formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R4 , or -S-,
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a pharmaceutically acceptable diluent, excipient or carrier a pharmaceutically acceptable diluent, excipient or carrier.
  • a pharmaceutical composition according to statement 16 further comprising one or more antimicrobial agents.
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a C 1 .3 alkylene group, a C 1 .3 alkyl carbonyl group, a carbonyl group, a C 1 .3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a method of preventing or treating bacterial infections comprising administering to a subject in need thereof a therapeutically effective amount of a compound according to formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a method of preventing or inhibiting biofilm formation on a surface comprising the treatment of the surface, or a device bearing the surface, with a compound according to formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R4 , or -S-, wherein R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered aryl group, an optionally substituted 5- or 6-membered heteroaryl group, or an optionally substituted 5- or 6-membered cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S; or is an optionally substituted 5- or 6-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R4 , or -S-,
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 - 6 alkenyl group, an optionally substituted C 2 - 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • V is a -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6- membered cycloalkenyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group.
  • ring A is an optionally substituted 6- or 5- membered aryl group, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, or an optionally substituted 5- or 6-membered cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S; or is an optionally substituted 5-membered heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or -N(R-i)-.
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6- membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6- or 5- membered aryl, heterocyclyl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl or heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or -N(R-i)-.
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6- membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6 or 5- or membered aryl, heterocyclyl, or heteroaryl group;
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -SO2-, -N(R 3 )-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6- 14 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6-membered aryl or heterocyclyl group.
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S.
  • Xi, X 2 , and X 3 are each independently selected from CR 5 R 5 , CR 5 , O, N, NR 7 , and S, and at least one is selected from O, N, NR 7 , and S, the possibility of CR 5 R 5 or CR 5 , and NR 7 or N depending on the degree of saturation of ring B,
  • R 5 , 5, and R 7 are each independently a hydrogen atom, an optionally substituted Ci_6 alkyl group, or an optionally substituted Ci_ 6 alkyl carbonyloxy group.
  • Xi is selected from O, N, and S, and X 2 and X 3 are both N.
  • V is -SO2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group.
  • W is a bond, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, or a carbamoyl group.
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group.
  • Y is -S-, a bond, -O- .
  • ring A is an optionally substituted 6-membered aryl, heterocyclyl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing 3 heteroatoms selected from O, N, and S;
  • Y is a -S0 2 -, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6-14 aryl group;
  • W is a bond
  • Y is -S-
  • Z is a Ci_6 alkyl carbamoyl group
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • ring A is an optionally substituted 6-membered aryl, heterocyclyl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing from 3 heteroatoms selected from O, N, and S;
  • V is a -S0 2 -,-N(R3)S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6-14 aryl group;
  • W is a carbamoyl group
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • ring A is an optionally substituted 6- or 5-membered aryl, heterocyclyl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl heterocyclyl or group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or -N(R 4 )-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6- membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6- or 5-membered aryl, heterocyclyl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl or heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or -N(R4 ,
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6 -i4 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6- membered cycloalkenyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a pharmaceutical composition comprising a compound of the formula (I):
  • ring A is an optionally substituted 6- or 5-membered aryl, heterocyclyl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl or heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or -N(R4 , wherein R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6- membered cycloalkenyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a pharmaceutical composition according to statement 43 further comprising one or more antimicrobial agents.
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a medical device according to statement 45 wherein the device is for in vivo implantation.
  • a medical device according to statement 45 or statement 46, wherein the device is a catheter, cannula, stent, shunt, or hypodermic needle.
  • a method of preventing or treating bacterial infections comprising administering to a subject in need thereof a therapeutically effective amount of a compound according to formula (I):
  • ring A is an optionally substituted 6- or 5-membered aryl, heterocyclyl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heteroaryl or heterocyclyl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -SO2-, -N(R 3 )-, -CH2-, -N(R 3 )S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • W is a bond, a C 1 .3 alkylene group, a C 1 .3 alkyl carbonyl group, a carbonyl group, a Ci_3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is -S-, a bond, -0-, or-N(R4 ,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a Ci_6 alkyl carbamoyl group, a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_6 alkoxy carbonyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6- membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted C 6-14 aryl group, an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • a method of prevention or treatment according to statement 50 wherein the compound of formula (I) is administered prior to, concurrent with, or following administration of at least one antibiotic.
  • a method of preventing or inhibiting bio film formation on a surface comprising the treatment of the surface, or a device bearing the surface, with a compound according to formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R4 , or -S-,
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 - 6 alkenyl group, an optionally substituted C 2 - 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 5- or 6- membered heterocyclyl, an optionally substituted 5- or 6-membered aryl, an optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 5- or 6-membered cycloalkyl group.
  • ring A is an optionally substituted 6-membered heterocyclyl or an optionally substituted 6-membered aryl group. Even more preferably, ring A is an optionally substituted 6-membered aryl group.
  • ring B is an optionally substituted 5- membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S.
  • ring B is a 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S.
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, - N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group.
  • V is -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group.
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalky
  • V is -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is as defined above.
  • R 3 is a hydrogen atom, an optionally substituted 3- to 6-membered cycloalkyl group, or an optionally substituted Ci_ 6 alkyl group.
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group.
  • W is a bond, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, or a carbamoyl group.
  • R 4 is a hydrogen atom, an optionally substituted 3- to 6-membered cycloalkyl group, or an optionally substituted Ci_ 6 alkyl group.
  • Y is a bond, -O- , or -S-. Most preferably, Y is a bond or -S-.
  • Z is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a Ci_ 3 alkoxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a Ci_ 3 alkyl carbamate group. Even more preferably, Z is a bond, a Ci_ 3 alkyl carbonyl group, a Ci_ 3 alkyl carbonyloxy group, or a Ci_ 3 alkyl carbamoyl group.
  • Ri is an optionally substituted 5- or 6- membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group.
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkenyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group.
  • Xi, X 2 , and X 3 are each independently selected from CR 5 R 5 , CR 5 , O, N, NR 7 , and S, and at least one is selected from O, N, NR 7 , and S, the possibility of CR 5 R 5 or CR 5 , and NR 7 or N depending on the degree of saturation of ring B,
  • R5, R ⁇ , and R 7 are each independently a hydrogen atom, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted Ci_ 6 alkyl carbonyloxy group, and each of the other groups is as defined above in relation to formula (I).
  • Xi is selected from O, N, and S, and X 2 and X 3 are both N,
  • heteroaryl rings include triazolyl, oxadiazolyl, and thiadiazolyl (preferably oxadiazolyl).
  • each of the optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted cycloalkenyl, optionally substituted hydroxy, and optionally substituted amino groups may be substituted by:
  • Ci_6 alkyl preferably methyl, ethyl or isopropyl
  • Ci_6 alkenyl preferably propenyl
  • Ci_6 alkynyl preferably ethynyl or propynyl
  • Ci_6 alkoxy (preferably methoxy)
  • Ci_6 alkyl carbonyl including ketones and derivatives thereof such as ketals and hemiketals, and aldehydes (e.g. formyl) and derivatives thereof such as acetals and hemiacetals (preferably acetyl),
  • Ci_6 alkyl carbamoyl including carbamoyl
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -N(R 3 )-, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 _ 14 aryl group;
  • Z is a bond, a Ci_ 6 alkylene carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_ 6 alkyl carbamoyl group, a Ci_ 6 alkyl carbonyloxy group, or a Ci_ 6 alkyl carbamate group;
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing 3 heteroatoms selected from O, N, and S;
  • V is a -N(R3)S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6-14 aryl group;
  • W is a bond
  • Y is -S-
  • Z is a Ci_6 alkyl carbamoyl group
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group; or a pharmaceutically acceptable salt thereof.
  • ring A is an optionally substituted 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing from 3 heteroatoms selected from O, N, and S
  • V is a -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6- membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6-14 aryl group;
  • W is a carbamoyl group
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group; or a pharmaceutically acceptable salt thereof.
  • each of the optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted cycloalkenyl, optionally substituted hydroxy, and optionally substituted amino groups, may be substituted by:
  • a group selected from -J-aryl, -J- heteroaryl, -J-heterocyclyl and -J-C 3 _ 6 cycloalkyl wherein J represents a bond or Ci_ 3 alkylene, and said aryl is selected from phenyl, said heteroaryl is selected from triazolyl, thiazolyl, thienyl, pyrazolyl, pyrimidyl, pyridazinyl, pyrazinyl, and pyridyl, said heterocyclyl is selected from pyrrolidinyl, azetidinyl, pyrazolidinyl, oxazolidinyl, piperidinyl, piperazinyl, morpholinyl, and thiazolidinyl, and said C 3 _6 cycloalkyl is selected from cyclopropyl, cyclopentyl and cyclohexyl; or
  • Ci_6 alkyl preferably methyl, ethyl or isopropyl
  • Ci_ 3 alkenyl preferably propenyl
  • Ci_6 alkyl carbonyl preferably acetyl
  • Ri is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group; and
  • each of the optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted cycloalkenyl, optionally substituted hydroxy, and optionally substituted amino groups may be substituted by:
  • Ci_6 alkyl preferably methyl, ethyl or isopropyl
  • Ci_6 alkenyl preferably propenyl
  • Ci_6 alkynyl preferably ethynyl or propynyl
  • halogen preferably CI or Br
  • haloCi_6 alkyl preferably trifluoromethyl
  • Ci_6 alkoxy (preferably methoxy)
  • Ci_6 alkyl carbonyl including ketones and derivatives thereof such as ketals and hemiketals, and aldehydes (e.g. formyl) and derivatives thereof such as acetals and hemiacetals (preferably acetyl),
  • Ci_6 alkyl carbamoyl including carbamoyl
  • R 2 is an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group; preferably R 2 is an optionally substituted 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6- membered cycloalkenyl group, an optionally substituted C 2 _ 6 alkenyl
  • Ci_6 alkyl preferably methyl, ethyl or isopropyl
  • Ci_6 alkenyl preferably propenyl
  • Ci_6 alkynyl preferably ethynyl or propynyl
  • Ci_6 alkoxy (preferably methoxy)
  • Ci_6 alkyl carbonyl including ketones and derivatives thereof such as ketals and hemiketals, and aldehydes (e.g. formyl) and derivatives thereof such as acetals and hemiacetals (preferably acetyl),
  • Ci_6 alkyl carbamoyl including carbamoyl
  • heteroaryl refers to a 5- to 6-membered monocyclic aromatic ring in which the monocyclic ring contains 1 to 4 heteroatoms selected from oxygen, nitrogen, and sulphur.
  • heteroaryl is selected from the group comprising thienyl, furyl, furazanyl, pyrrolyl, triazolyl, tetrazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyranyl, pyrazolyl, pyrimidyl, pyridazinyl, pyrazinyl, pyridyl, triazinyl, and tetrazinyl.
  • heterocyclyl refers to a 5- to 6- membered monocyclic ring which may be saturated or partially unsaturated, in which the monocyclic ring contains 1 to 4 heteroatoms selected from oxygen, nitrogen, and sulphur.
  • heterocyclyl is selected from the group comprising aziridinyl, oxiranyl, pyrrolidinyl, azetidinyl, pyrazolidinyl, oxazolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, hydantoinyl, valerolactamyl, oxiranyl, oxetanyl, dioxolanyl, dioxanyl, oxathiolanyl, oxathianyl, dithianyl, dihydrofuranyl, tetrahydrofuranyl, dihydropyranyl, tetrahydropyranyl, tetrahydropyridinyl, tetrahydropyrimi
  • the compound is selected from the group of N-(4-chlorophenyl)-2-((5-(4-(N-cyclopentylsulfamoyl)phenyl)-l,3,4-oxadiazol-2- yl)thio)acetamide, N-(4-chlorophenyl)-2-((5-(4-(N-cyclohexylsulfamoyl)phenyl)-l,3,4- oxadiazol-2-yl)thio)acetamide, N-(4-chlorophenyl)-2-[[5-[4-(4- phenylcyclohexyl)sulfonylphenyl]-l,3,4-oxadiazol-2-yl]sulfanyl]acetamide, 2-[[5-[4-(4- benzylcyclohexyl)sulfonylphenyl]-l,3,4-oxadiazol-2-yl]
  • Ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group.
  • ring A is an optionally substituted 6-membered heterocyclyl or aryl group. Even more preferably, ring A is an optionally substituted 6- membered aryl group.
  • Ring B is an optionally substituted 5 -membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S.
  • ring B is a 5- membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S. It is believed that when ring B is a 5 -membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S, binding of the compound in the P5 pocket of the CU pili subunit is further enhanced.
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group.
  • V is -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is as defined above.
  • R 3 is a hydrogen atom, an optionally substituted 3- to 6-membered cycloalkyl group, or an optionally substituted Ci_ 6 alkyl group.
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group.
  • W is a bond, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, or a carbamoyl group.
  • Y is a bond, -0-, - ⁇ ( ⁇ )-, or -S-, wherein R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group.
  • R4 is a hydrogen atom, an optionally substituted 3- to 6-membered cycloalkyl group, or an optionally substituted Ci_ 6 alkyl group.
  • Y is a bond, -0-, or -S-. Most preferably, Y is a bond or -S-.
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group.
  • Z is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a Ci_ 3 alkoxy carbonyl group, a Ci_ 3 alkyl carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a Ci_ 3 alkyl carbamate group. Even more preferably, Z is a bond, a Ci_ 3 alkyl carbonyl group, a Ci_ 3 alkyl carbonyloxy group, or a Ci_ 3 alkyl carbamoyl group.
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 - 6 alkenyl group, an optionally substituted C 2 - 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group.
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkenyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6-14 aryl group.
  • Xi, X 2 , and X 3 are each independently selected from CR 5 R 5 , CR 5 , O, N, NR 7 , and S, and at least one is selected from O, N, NR 7 , and S, the possibility of CR 5 R 5 or CR 5 , and NR 7 or N depending on the degree of saturation of ring B, wherein R 5 , 5, and R 7 are each independently a hydrogen atom, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted Ci_ 6 alkyl carbonyloxy group,
  • each of the other groups is as defined above in relation to formula (I).
  • Xi, X 2 , and X 3 form saturated bonds with neighbouring atoms, they may be selected from CR 5 R 0 , O, NR 7 , and S.
  • Xi, X 2 , and X 3 form unsaturated bonds with neighbouring atoms, they may be selected from CR 5 and N.
  • Xi is selected from O, N, and S, and X 2 and X 3 are both N,
  • heteroaryl rings include triazolyl, oxadiazolyl, and thiadiazolyl (preferably oxadiazolyl).
  • Each of the optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted cycloalkenyl, optionally substituted hydroxy, and optionally substituted amino groups, may be substituted by:
  • Ci_6 alkyl preferably methyl, ethyl or isopropyl
  • Ci_6 alkenyl preferably propenyl
  • Ci_6 alkynyl preferably ethynyl or propynyl
  • Ci_6 alkoxy (preferably methoxy)
  • Ci_6 alkyl carbonyl including ketones and derivatives thereof such as ketals and hemiketals, and aldehydes (e.g. formyl) and derivatives thereof such as acetals and hemiacetals (preferably acetyl),
  • Ci_6 alkyl carbamoyl including carbamoyl
  • 'halogen' refers to a fluorine, chlorine, bromine or iodine atom, and any radioactive isotope thereof, including fluorine-18, iodine-123, iodine-124, iodine-125, iodine- 131, and astatine-211, unless otherwise specified.
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is an optionally substituted 5-membered heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is -0-, -N(R 3 )-, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 _ 14 aryl group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted Ci_6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • ring A is an optionally substituted 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing 3 heteroatoms selected from O, N, and S;
  • V is a -N(R3)S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6-14 aryl group;
  • W is a bond
  • Y is -S-
  • Z is a Ci_6 alkyl carbamoyl group
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • ring A is an optionally substituted 6-membered heterocyclyl, aryl, or heteroaryl group
  • ring B is a 5-membered heteroaryl group containing from 3 heteroatoms selected from O, N, and S;
  • V is a -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-, wherein R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, or an optionally substituted C 6-14 aryl group; W is a carbamoyl group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group;
  • each of the optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted cycloalkenyl, optionally substituted hydroxy, and optionally substituted amino groups may be substituted by:
  • a group selected from -J-aryl, -J- heteroaryl, -J-heterocyclyl and -J-C3-6 cycloalkyl wherein J represents a bond or Ci_ 3 alkylene, and said aryl is selected from phenyl, said heteroaryl is selected from triazolyl, thiazolyl, thienyl, pyrazolyl, pyrimidyl, pyridazinyl, pyrazinyl, and pyridyl, said heterocyclyl is selected from pyrrolidinyl, azetidinyl, pyrazolidinyl, oxazolidinyl, piperidinyl, piperazinyl, morpholinyl, and thiazolidinyl, and said C3-6 cycloalkyl is selected from cyclopropyl, cyclopentyl and cyclohexyl; or
  • Ci_6 alkyl preferably methyl, ethyl or isopropyl
  • Ci_3 alkenyl preferably propenyl
  • Ci_3 alkoxy (preferably methoxy)
  • Ci_6 alkyl carbonyl preferably acetyl
  • Ci_3 alkyl carbonyloxy including carboxyl
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • the compounds of the present invention are believed to function by inhibiting the pilus subunit polymerization step during type 1 pilus assembly, thereby preventing the formation of type 1 pili on the bacterial surface.
  • they have been found to efface pre-assembled pili from the bacterial cell surface. As such, they are potentially effective for the prophylaxis or treatment of medical conditions associated with bacterial infections.
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R4 , or -S-, wherein R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 -6 alkenyl group, an optionally substituted C 2 -6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a
  • Ci_6 alkyl carbonyloxy group a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 - 6 alkenyl group, an optionally substituted C 2 - 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • the compounds of the present invention are for use in the prophylaxis or treatment of a bacterial infection caused by pathogenic bacteria, preferably pathogenic bacteria of the family of Enterobacteriaceae, including the genera Escherichia, Enterobacter Klebsiella, Salmonella, Shigella, and Yersinia. More preferably, the compounds of the present invention are for use in the prophylaxis or treatment of uropathogenic bacteria, such as Escherichia coli.
  • the bacterial infection may be hospital acquired or community acquired.
  • a bacterial infection may be a urinary tract infection, including cystitis (infection of the bladder), pyelonephritis (infection of the kidney), and bacteriuria (infection of the urine), as well as infectious complications thereof, such as those resulting in acute renal failure.
  • a bacterial infection may be an infection of the gastrointestinal tract, in particular the gastrointestinal mucosa. Infections of the gastrointestinal tract include, but are by no means not limited to, inflammatory bowel disease (IBD), such as Crohn's disease or ulcerative colitis, as well as infectious complications thereof, such as colorectal cancer and irritable bowel syndrome.
  • IBD inflammatory bowel disease
  • infectious complications thereof such as colorectal cancer and irritable bowel syndrome.
  • the compound of formula (I) may be used as the sole therapeutic agent, or may be employed in conjunction with at least one further pharmacologically active agent, such as anti- infectives (e.g. disinfectants, antiseptics, antibacterials, antifungals, and antivirals) or anti-virulence agents.
  • anti- infectives e.g. disinfectants, antiseptics, antibacterials, antifungals, and antivirals
  • anti-virulence agents e.g., anti-virulence agents.
  • antimicrobial agents include, but are by no means limited to, amikacin, gentamicin, tobramycin, amoxicillin, amoxicillin/clavulanate, amphotericin B, ampicillin, ampicillin/sulbactam, atovaquone, azithromycin, cefazolin, cefepime, cefotaxime, cefotetan, cefpodoxime, ceftazidime, ceftizoxime, ceftriaxone, cefuroxime, cephalexin, chloramphenicol, clotrimazole, ciprofloxacin, clarithromycin, clindamycin, cicloxacillin, coxycycline, echincandins, erythromycin (including estolate, ethylsuccinate, gluceptate, lactobionate, and stearate), fluconazole, foscarnet, imipenem/cilastatin (Primaxin), isoniazid, it
  • Suitable pharmacologically active agents which can be used in combination with the compound of formula (I) include one or more other anti- virulence drugs, such as pilicides and D-mannosides (see Background section), one or more anti-viral drugs, such as famciclovir and ganciclovir, one or more anti-inflammatory drugs, such as steroid anti-inflammatory drugs (e.g.
  • glucocorticoids and non-steroid anti-inflammatory drugs (for example, aspirin, ibuprofen, naproxen, and mesalazine), one or more immunosuppressants (for example, prednisone, TNF inhibition, azathioprine, methotrexate, 6-mercaptopurine), or one or more chemotherapeutic drugs (for example, fluorouracil, capecitabine, UFT (tegafur-uracil), leucovorin, irinotecan, oxaliplatin, and paclitaxel), amongst others.
  • immunosuppressants for example, prednisone, TNF inhibition, azathioprine, methotrexate, 6-mercaptopurine
  • chemotherapeutic drugs for example, fluorouracil, capecitabine, UFT (tegafur-uracil), leucovorin, irinotecan, oxaliplatin, and paclitaxel
  • the present invention also relates to a pharmaceutical composition
  • a pharmaceutical composition comprising a compound according to formula (I), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent, excipient or carrier.
  • the pharmaceutical composition may further comprise one or more other pharmacologically active agents (as above), such as one or more antimicrobial agents.
  • the composition may contain one or more antibiotics (as above).
  • compositions include, but are not limited to, ion exchangers, alumina, aluminium stearate, lecithin, serum proteins, such as human serum albumin, buffer substances such as phosphates, glycine, sorbic acid, potassium sorbate, partial glyceride mixtures of saturated vegetable fatty acids, water, salts or electrolytes, such as protamine sulphate, disodium hydrogen phosphate, potassium hydrogen phosphate, sodium chloride, zinc salts, colloidal silica, magnesium trisilicate, polyvinyl pyrrolidone, cellulose-based substances, polyethylene glycol, sodium carboxymethylcellulose, polyacrylates, waxes, polyethylene- polyoxypropylene-block polymers, polyethylene glycol and wool fat.
  • ion exchangers alumina, aluminium stearate, lecithin
  • serum proteins such as human serum albumin
  • buffer substances such as phosphates, glycine, sorbic acid, potassium sorbate, partial g
  • a pharmaceutical composition can be administered to a subject by various routes including, for example, oral administration; intramuscular administration; intravenous administration; anal administration; vaginal administration; parenteral administration; nasal administration; intraperitoneal administration; subcutaneous administration; (intra)urethral administration and topical administration.
  • routes including, for example, oral administration; intramuscular administration; intravenous administration; anal administration; vaginal administration; parenteral administration; nasal administration; intraperitoneal administration; subcutaneous administration; (intra)urethral administration and topical administration.
  • One skilled in the art would select an effective dose and administration regimen taking into consideration factors such as the patient's weight and general health, and the particular condition being treated, etc.
  • compositions of this invention may be administered orally, parenterally, topically, rectally, buccally, urethrally or via an implanted reservoir.
  • the pharmaceutical compositions are administered orally, rectally, urethrally or by injection.
  • the pharmaceutical compositions may contain any conventional non-toxic pharmaceutically- acceptable carriers, adjuvants or vehicles.
  • parenteral as used herein includes subcutaneous, intracutaneous, intravenous, intramuscular, intravaginal, intraurethral, intra- articular, intrasynovial, intrasternal, intrathecal, intraocular, intralesional and intracranial injection or infusion techniques.
  • the route of administration of the composition is oral or rectal administration.
  • the pharmaceutical composition could be in the form of a liquid, gel, lotion, tablet, capsule, or ointment, etc.
  • the following compounds are:
  • a compound of formula (I) may be incorporated in a medical device, or an article on which bacterial colonisation may occur, in order to reduce or prevent the colonisation of bacterial pathogens on the device or article before or whilst it is being used.
  • the present compounds inhibit the formation of biofilms by either preventing the formation of adhesive pili or removing adhesive pili, the means by which Gram-negative bacteria adhere to biological or non-biological surfaces and cause infection.
  • biofilm is known in the art.
  • a biofilm is an aggregate of microorganisms in which cells adhere to each other and/or to a surface. These adherent cells are frequently embedded within a self-produced matrix generally composed of extracellular DNA, proteins, and polysaccharides in various configurations.
  • Biofilms can contain many different types of microorganism, e.g. bacteria, archaea, protozoa, fungi and algae. However, monospecies biofilms occur as well.
  • Microorganisms living in a biofilm usually have significantly different properties from free-floating (planktonic) microorganisms of the same species, as a result of the dense and protected environment of the film.
  • the present invention also concerns a medical device, laboratory apparatus, food preparation surface-bearing device, nanoparticle material, or packaging material, incorporating a compound of the formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Z is a bond, a Ci_ 6 alkylene group, a Ci_ 6 alkyl carbonyl group, a Ci_ 6 alkoxy carbonyl group, a Ci_6 alkyl carbonyloxy group, a Ci_ 6 alkyl carbamoyl group, or a Ci_ 6 alkyl carbamate group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6-14 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • the device is preferably for in vivo implantation.
  • the claimed compounds mitigate the likelihood of bacterial infections being introduced by, or resulting from, medical procedures involving medical devices.
  • medical devices include, for example, catheters, cannulas, stents, shunts, or hypodermic needles.
  • the present compounds show distinct utility when applied to or incorporated in a catheter, since they can efficiently reduce the occurrence of UTIs (especially hospital-associated UTIs).
  • the compound of formula (I) may be incorporated in the medical device, laboratory apparatus, food preparation surface-bearing device, nanoparticle material, or packaging material as a component of the material making up the body of the article, or may be disposed as a coating or outer layer thereon. Incorporation may include absorption of the compound into the matrix of the medical device, laboratory apparatus, food preparation surface-bearing device, nanoparticle material, or packaging material, or covalent chemical attachment of the compound thereto.
  • the compound according to formula (I) is disposed as a coating on a surface of the medical device, laboratory apparatus, food preparation surface-bearing device, nanoparticle material, or packaging material, which preferably, in use, comes into contact with a biological material or a subject to be treated with the device.
  • a method of preventing or treating bacterial infections, cystitis, inflammatory bowel diseases, or irritable bowel syndrome comprising administering to a subject in need thereof a therapeutically effective amount of a compound according to formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R 4 , or -S-,
  • R 4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted C 2 _ 6 alkenyl group, an optionally substituted C 2 _ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino
  • a subject may be a human or an animal patient.
  • An animal may be a horse, cow, dog, cat, sheep, rat, mouse, pig, or bird, etc.
  • a subject is a human patient.
  • this method of prevention or treatment is for use in bacterial infections, as mentioned above.
  • the compound of formula (I) may be used as the sole therapeutic agent, or may be employed in conjunction with at least one further pharmacologically active agent (as above).
  • the present compounds exhibit a particular synergy when used in combination with one or more antibiotics, and may be administered prior to, concurrently with, or following administration of at least one antibiotic.
  • antibiotics include, but are by no means limited to, those listed above.
  • a method of preventing or inhibiting biofilm formation on a surface comprising the treatment of the surface, or a device bearing the surface, with a compound according to formula (I):
  • ring A is an optionally substituted 5- or 6-membered heterocyclyl, aryl, heteroaryl, or cycloalkyl group;
  • ring B is an optionally substituted 5-membered heterocyclyl or heteroaryl group containing from 1 to 3 heteroatoms selected from O, N, and S;
  • V is a bond, -0-, -N(R 3 )-, -CH 2 -, -N(R 3 )S0 2 -, -S0 2 -, or -S0 2 N(R 3 )-,
  • R 3 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkenyl group, an optionally substituted Ci_ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • W is a bond, a Ci_ 3 alkylene group, a Ci_ 3 alkyl carbonyl group, a carbonyl group, a Ci_ 3 alkoxy carbonyl group, an oxycarbonyl group, a Ci_ 3 alkyl carbonyloxy group, a carbonyloxy group, a Ci_ 3 alkyl carbamoyl group, or a carbamoyl group;
  • Y is a bond, -0-, -N(R4 , or -S-,
  • R4 is a hydrogen atom, an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkenyl group, an optionally substituted Ci_ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, or an optionally substituted C 6 -i4 aryl group;
  • Ri and R 2 are each independently an optionally substituted 5- or 6-membered heterocyclyl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 3- to 6-membered cycloalkyl group, an optionally substituted 5- or 6-membered cycloalkenyl group, an optionally substituted Ci_ 6 alkyl group, an optionally substituted Ci_ 6 alkenyl group, an optionally substituted Ci_ 6 alkynyl group, an optionally substituted Ci_ 6 alkoxy group, an optionally substituted C 6 -i4 aryl group, an optionally substituted hydroxy group, or an optionally substituted amino group;
  • any of the structural variants mentioned above in relation to formula (I) also represent preferred aspects of this embodiment, which may be employed in this method.
  • the surface may be treated, for example, by immersion in a solution comprising the compound of formula (I), or by spraying a solution comprising the compound of formula (I) thereon.
  • the compound of formula (I) may be covalently attached to the surface, either directly or via a suitable linker moiety.
  • the invention provides a method of functionalising a surface, or a device bearing the surface, the method comprising covalently attaching the compound of formula (I) to the surface, directly or via a suitable linker moiety.
  • DSE progression is presented as adjusted volume of pixels of the DSE product (FimH: FimGNte) normalised over the adjusted volume of pixels of the total protein (FimC + FimH + FimH:FimGNte) and shown as a function of compound 1 concentration.
  • the N-terminal extension on an incoming subunit displaces the chaperone bound to the subunit at the base of the fibre, (b) X-ray structures the FimH pilin domain (residues 158-279; shown as molecular surface) in complex with the FimC chaperone (left; taken from PDB: 1ZE3; shown in ribbon representation) or FimG Nte (right; taken from PDB:3JWN; shown in ribbon representation).
  • CU pilus subunits are characterised by an incomplete Ig-fold, lacking the C-terminal ⁇ -strand, and by the presence of a disordered 10-20 residues extension at the N-terminus (Choudhury, et al. Science 1999, 285: 1061-1066; Sauer, et al. Science 1999, 285: 1058-1061).
  • pilus subunits are stabilised by the chaperone, which donates an extended ⁇ -strand (strand Gl) to complement the missing structural information in the subunit Ig-fold (Choudhury, et al. Science 1999, 285: 1061-1066; Sauer, et al. Science 1999, 285: 1058-1061).
  • Nte N-terminal extension peptide
  • DSE 'donor-strand exchange'
  • FimH constitutes the first subunit to be incorporated, is present in a single copy and is crucial to activate the FimD usher for pilus assembly (Nishiyama, et al. Science 2008, 320: 376-379).
  • FIG. 2b Representative electron micrographs showed peritrichous piliation of bacteria in DMSO-control, whereas treatment with 200 ⁇ and 50 ⁇ of compound 1 resulted in non- and pauci-piliated bacteria, respectively (Fig. 2c). Moreover, the few pili that were present on the bacteria at 50 ⁇ of compound 1 were aberrantly long (Fig.2c). A similar phenotype is observed in fimH mutant strains, where the accumulated periplasmic pool of FimA pilus subunits is directed to those few pilus assembly platforms in the outer membrane that non-specifically become activated for pilus assembly in absence of FimH (Ronald, et al.
  • l,3,4-Oxadiazole-2-thiols can be accessed from the corresponding hydrazides by refluxing in ethanol with a base such as potassium hydroxide, triethylamine or 4-methyl morpholine in the presence of carbon disulfide. Treatment with a suitable acid, such as hydrochloric acid, gives the l,3,4-oxadiazole-2-thiol.
  • a base such as potassium hydroxide, triethylamine or 4-methyl morpholine in the presence of carbon disulfide.
  • a suitable acid such as hydrochloric acid
  • the hydrazides required for the cyclisation step can be formed from the coupling of t-butyl carbazate with a carboxylic acid using a suitable coupling reagent such as l-[3- (dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (EDC), benzotriazol-l-yl- oxytripyrrolidinophosphonium hexafluorophosphate (PyBop) or O-(Benzotriazol-l-yl)- A .A .N'.N'-tetramethyluronium hexafluorophosphate (HBTU).
  • EDC benzotriazol-l-yl- oxytripyrrolidinophosphonium hexafluorophosphate
  • HBTU O-(Benzotriazol-l-yl)- A .A .N'.N'-tetramethyluronium hexafluorophosphat
  • An alternative strategy to synthesise hydrazides is by refluxing an ester with hydrazine hydrate in a suitable solvent, such as ethanol or methanol.
  • the l,3,4-oxadiazole-2-thiol core can be functionalised by, for example, alkylation. This can be achieved by using an alkylating agent, such as bromoacetic acid, in the presence of a suitable base, such as sodium hydroxide, potassium hydroxide or 4-methyl morpholine.
  • alkylating agent such as bromoacetic acid
  • a suitable base such as sodium hydroxide, potassium hydroxide or 4-methyl morpholine.
  • the synthesis may be completed by a final amide coupling reaction with a suitable amine coupling partner and a coupling reagent such as EDC, PyBOP or HBTU.
  • Sulfonamide side-chains can be introduced at an early stage in the synthesis by the reaction of a suitable amine with a sulfonyl chloride, in the presence of a base, such as sodium hydroxide or pyridine.
  • a base such as sodium hydroxide or pyridine.
  • sulphonamides having a reversed configuration can be synthesised with the appropriate reaction partners and using a suitable base, such as sodium hydroxide or pyridine.
  • l,3,4-oxadiazole-2-amino analogues can be accessed by reacting the corresponding hydrazide with cyanogen bromide in methanol in the presence of a suitable base, such as potassium carbonate, potassium h drogen carbonate or sodium hydro en carbonate.
  • a suitable base such as potassium carbonate, potassium h drogen carbonate or sodium hydro en carbonate.
  • the l,3,4-oxadiazole-2-amino core can then be reacted with a carboxylic acid coupling partner in the presence of a suitable amide coupling reagent, such as EDC, PyBop or HBTU, to give access to l,3,4-oxadiazole-2-amino analogues.
  • a suitable amide coupling reagent such as EDC, PyBop or HBTU
  • l,3,4-thiadiazole-2-thiol analogues can be synthesised from the corresponding hydrazide by refluxing with carbon disulfide in ethanolic base, such as potassium carbonate or potassium hydroxide followed by treatment with cone, sulphuric acid.
  • 1 ,3,4-thiadiazole-2-thiol analogues The l,3,4-thiadiazole-2-thiol can then be alkylated using an alkylating agent, such as bromoacetic acid, in the presence of a base, such as sodium hydroxide, to give access to 1,3,4- thiadiazole-2-thiol analogues. This is then followed by amide bond formation with a suitable amine in the presence of a amide coupling reagent, such as EDC, PyBop or HBTU, to give 1 ,3,4-thiadiazole-2-thiol analogues. l,2,4-triazole-3-thiol analo ues
  • l,2,4-triazole-3-thiol analogues can be synthesised from the corresponding thiosemicarbazide, which can be prepared from the reaction of an acid chloride with thiosemicarbazide in the presence of a base such as pyridine.
  • a base such as pyridine.
  • This benzothiosemicarbazide can then be cyclised to the l,2,4-triazole-3-thiol by refluxing in ethanol in the presence of a base, such as sodium hydroxide or potassium hydroxide.
  • Alkylation of this thiol can be achieved by reaction with a suitable alkylating agent such as bromoacetic acid, in the presence of a base. This is then followed by amide bond formation with a suitable amine in the presence of an amide coupling reagent, such as EDC, PyBop or HBTU to give l,2,4-triazole-3-thiol analogues.
  • a suitable alkylating agent such as bromoacetic acid
  • the l,2,4-triazole-3-thiol core can be synthesised by refluxing the hydrazide compound with trimethylsilyl isothiocyanate in ethanol, followed by cyclisation in the presence of base to give the l,2,4-triazole-3-thiol core.
  • NMR spectra were measured with a Bruker DRX 500 or 600 MHz spectrometer; chemical shifts are expressed in ppm relative to TMS as an internal standard and coupling constants (J) in Hz.
  • Mass spectra were obtained using a Waters ZQ2000 single quadrupole mass spectrometer with electrospray ionisation (ESI). High resolution mass spectra were acquired on a Waters LCT time of flight mass spectrometer with electrospray ionisation (ESI) or chemical ionization (CI).
  • N-cyclopentyl-4-(5-mercapto-l,3,4-oxadiazol-2-yl)benzenesulfonamide 80 mg, 0.25 mmol
  • ethanol 8.0 mL
  • N-methylmorpholine 35 ⁇ , 0.32 mmol
  • bromoacetic acid 38 mg, 0.27 mmol
  • the reaction was stirred at RT for 72 h before being evaporated in vacuo and the residue dissolved in DCM (25 mL) and washed with HC1 (1 M aq., 20 mL).
  • N-cyclopentyl-4-(5-mercapto-l,3,4-oxadiazol-2-yl)benzenesulfonamide 100 mg, 0.29 mmol
  • ethanol 7.7 mL
  • N-methylmorpholine 42 ⁇ L, 0.38 mmol
  • bromoacetic acid 45 mg, 0.32 mmol
  • the reaction was stirred at RT for 72 h before being evaporated in vacuo and the residue dissolved in DCM (25 mL) and washed with HC1 (1 M aq., 20 mL).
  • Morpholine (793 ⁇ , 9.07 mmol) was added to a stirred solution of 4-(chlorosulfonyl)benzoic acid (1.00 g, 4.53 mmol) in NaOH (10 mL, 10% aq.). The reaction was stirred at RT for 16 h before being acidified with cone. HCl. The resulting white precipitate was filtered, washed with HCl (1M aq.) and dried to give 4-(morpholinosulfonyl)benzoic acid as a white solid (650 mg, 53%>) which was used without further purification.
  • tert-Butylpiperidine hydrochloride (1.00 g, 7.08 mmol) was added to a stirred solution of 4-(chlorosulfonyl)benzoic acid (1.56 g, 7.08 mmol) and triethylamine (1.09 mL, 7.79 mmol) in DCM (45 mL). The reaction was stirred at RT for 16 h before being washed with HC1 (1M aq.) and dried (MgS0 4 ) to give 4-(piperidin-l-ylsulfonyl)benzoic acid as a white solid which was used without further purification.
  • tert-Eutyl 2-(4-((4-(tert-butyl)piperidin- 1 -yl)sulfonyl)benzoyl)hydrazine- 1 -carboxylate (6.50 mmol) was cooled to 0°C and trifluoroacetic acid (13.0 mL) was added dropwise. The mixture was allowed to warm to RT over 1 h before being quenched with NaOH (10% aq.) until effervescence ceased.
  • N,N-dibutyl-4-(5-mercapto-l,3,4-oxadiazol-2-yl)benzenesulfonamide (1.35 g, 3.66 mmol) in ethanol (100 mL) was added N-methylmorpholine (523 ⁇ , 4.76 mmol) and bromoacetic acid (559 mg, 4.02 mmol).
  • N-methylmorpholine 523 ⁇ , 4.76 mmol
  • bromoacetic acid 559 mg, 4.02 mmol

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Abstract

La présente invention concerne des composés de formule (I) et leurs utilisations. En particulier, bien que cela soit pas exclusif, elle concerne des composés hétérocycliques inhibant la biogenèse des pili adhésifs dans les bactéries à Gram négatif, ainsi que leur utilisation dans le traitement prophylactique ou thérapeutique d'états pathologiques issus de la colonisation par des agents pathogènes bactériens.
PCT/EP2014/058149 2013-04-22 2014-04-22 Composé à activité antibactérienne WO2014173904A1 (fr)

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EP3210469A1 (fr) 2016-02-23 2017-08-30 Bayer Cropscience AG Utilisation des thio-1,2,4-triazoles substitués pour augmenter le tolerance de stress dans des plants
WO2019076931A1 (fr) 2017-10-16 2019-04-25 Enterome Nouveaux outils pour évaluer l'efficacité thérapeutique des bloqueurs fimh
CN111511723A (zh) * 2017-08-21 2020-08-07 米可如比奥提克斯有限公司 用作抗菌剂的代谢稳定的n-酰基氨基噁二唑
CN112898222A (zh) * 2021-02-01 2021-06-04 长沙理工大学 噁二唑类化合物及其制备方法与应用
US11091447B2 (en) 2020-01-03 2021-08-17 Berg Llc UBE2K modulators and methods for their use
WO2021214020A1 (fr) 2020-04-24 2021-10-28 Bayer Aktiengesellschaft Aminothiazoles substitués utilisés comme inhibiteurs de la dgk zêta pour l'activation immunitaire
CN111166743B (zh) * 2020-01-02 2022-03-22 中国医学科学院医药生物技术研究所 一类含噻唑结构化合物的抗感染用途

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WO2010150927A1 (fr) * 2009-06-25 2010-12-29 Sk Holdings Co., Ltd. Composition pharmaceutique pour la prévention et le traitement de maladies cancéreuses, comprenant des dérivés de benzamide
EP2365091A1 (fr) * 2010-03-12 2011-09-14 Paul-Ehrlich-Institut Procédé de criblage pour inhibiteurs de protéase HtrA utiles pour la prophylaxie et thérapie pour infection bactérienne
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3210469A1 (fr) 2016-02-23 2017-08-30 Bayer Cropscience AG Utilisation des thio-1,2,4-triazoles substitués pour augmenter le tolerance de stress dans des plants
CN111511723A (zh) * 2017-08-21 2020-08-07 米可如比奥提克斯有限公司 用作抗菌剂的代谢稳定的n-酰基氨基噁二唑
WO2019076931A1 (fr) 2017-10-16 2019-04-25 Enterome Nouveaux outils pour évaluer l'efficacité thérapeutique des bloqueurs fimh
CN111166743B (zh) * 2020-01-02 2022-03-22 中国医学科学院医药生物技术研究所 一类含噻唑结构化合物的抗感染用途
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