AU2006239546B2

AU2006239546B2 - Imidazo(1,2-A)pyridine derivatives useful as peptide deformylase (PDF) inhibitors

Info

Publication number: AU2006239546B2
Application number: AU2006239546A
Authority: AU
Inventors: Michael Thormann
Original assignee: Novartis AG
Current assignee: Novartis AG
Priority date: 2005-04-25
Filing date: 2006-04-24
Publication date: 2010-04-15
Anticipated expiration: 2026-04-24
Also published as: AU2006239546A1; RU2409575C2; EP1877407A1; WO2006114261A1; KR20080002866A; CA2606251A1; JP2008538776A; MX2007013237A; BRPI0610842A2; CN101166740A; CN101166740B; RU2007143501A

Description

1 IMIDAZO [1,2-Al PYRIDINE DERIVATIVES USEFUL AS PEPTIDE DBFORMYIASE (PDF) INHIBITORS Peptide deformylase (PDF) Inhibitors 2 The present invention relates to new Inhbitors of peptide deformylase (PDF). These compounds are of great interest in particular as antibiOtics. 5 Peptide deformylase Is a bacteidal metaoenzyme which contains Iron. It is detectable In all bacteria and plays a vital role In bacterial metaboism. During protein synthesis, peptide deformylase catalyses the removal of the formyl group from the N-terminus of bacterial proteins. Without the enzyme, bacteria cannot produce any functioning proteins. 10 POptlde deoanylase Is the point of application of a new dass of antibiotics, which are catted peptide deformylase inhibitors. The present Invention advantageously prepares new Inhibitors of peptide deformylase that are obtainable synthetically in a simple manner. 15 The present invention relates to compounds of formula (I), R1.

R

2 N -1 (I) R Rr wherein 20 the radicas RR', ', Raand R', IndePenldentY of one another, a a hydrogen atom a halogen atom, a hydroxy, amino, nitro or thiole group, an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cloalky alkyCycloalkyt. hateralkylcydoalkyl, heterocycloikyi, aralkyl or a heterarlky1 radical, whereby each of these radicalsn lndpenfldly of one another, may be substituted, or two of the radicals R', R, R 3 and 25 R* together may be part of a cycloalkyt, heterocycloalkyl, aryl or hetemaryl ring, whereby each of these rings may optionally be substituted; R Is a hydrogen atom, a halogen atom, a hydroxy, amino, nitro or ihole group. an aIkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, C:IdRPrDCCWZfl742M-. DOC-2/25/20 -2 heteroalkylcycloakyl, heterocycloalkyl, aralkyl or heteroaralkyl radical, whereby each of these radicals may optionally be substituted; the radicals Re and R', Independently of one another, are a hydrogen atom, or an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalky kyoai, heterocycloalkyl, aralkyl or heteroaralkyl radical, whereby each of these radicals, independently of one another, may optionally be substituted; and X is a group of formula -CS-NHOH, -CHrCO-CHrOH, -CO-CHrOH, -CO-NHOH, -CNH-NHOH, -CH-NOH-CHS, -NOHCHS, -NOH-CHO, -CHrNOH-CHO, -CHrCHOH-CHO, -CHOH-CHO, -CHOH-COOH, -CH(CHrOH)-COOH. -COOH or -CH 2 COOH, or Is selected from the following formulae: H .. V D-G whereby U Is a bond, CH 2 , NH, 0 or S, V Is 0, S, AH or CH 2 , W Is 0, S, NH or CH 2 , and Y is OH or NH 2 , E is a bond, CH 2 , NH, 0 or S arid the groups D,.G and M, independently of one another, are N or CH, or a pharmaceutically acceptable salt, solvate, hydrate or a pharmaceutically acceptable formulation thereof. In another aspect, the present invention relates to compounds of formula (1) R, R N

R

C:\NRoCC\K727429.IDOC-2 2 6/IO -2A wherein the radicals R', R 2 , R 3 and R 4 , independently of one another, are a hydrogen atom, a halogen atom, a hydroxy, amino, nitro or thiole group, an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, hetero 5 alkylcycloalkyl, heterocycloalkyl, aralkyl or a heteroaralkyl radical, whereby each of these radicals, independently of one another, may be substituted, or two of the radicals R', R 2 , R 3 and R 4 together may be part of a cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring, whereby each of these rings may optionally be substituted;

R

5 is a hydrogen atom, an alkyl, alkenyl, heteroalkyl, or cycloalkyl, whereby each 10 of these radicals may optionally be substituted; the radicals R' and R', independently of one another, are a hydrogen atom, or an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroaralkyl radical, whereby each of these radicals, independently of one another, may optionally be 15 substituted; and X is a group of formula -CO-NHOH, or a pharmaceutically acceptable salt, solvate, hydrate or a pharmaceutically acceptable formulation thereof. The expression alkyl refers to a saturated, straight-chained or branched hydrocarbon group, which has in particular 1 to 20 carbon atoms, preferably I to 12 carbon atoms, 20 most preferably 1 to 6 carbon atoms, e.g. the methyl, ethyl, propyl, Isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, n-hexyl, 2,2-dimethylbutyl or n-octyl group. The expressions alkenyl and alkynyl refer to at least partly unsaturated, straight-chained or branched hydrocarbon groups, which have in particular 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, most preferably 2 to 6 carbon atoms, e.g. the ethenyl, allyl, acetylenyl, propargyl, isoprenyl or hex-2-enyl group. Alkenyl groups preferably have one or two (most preferably one) double bond(s) and the alkynyl groups have one or two (most preferably one) triple bond(s).

3 In addition, the expressions alkyl, alkenyl and alkynyl refer to groups, in which e.g. one or more hydrogen atoms are replaced by a halogen atom (preferably F or CI), -COOH, -OH, -SH, -NH 2 , -NO 2 , =0, =S, =NH, such as the 2,2,2-trichloroethyl or the 5 trifluoromethyl group. The expression heteroalkyl refers to an alkyl, alkenyl or alkynyl group, in which one or more (preferably 1, 2 or 3) carbon atoms are replaced by an oxygen, nitrogen, phosphorus, boron, selenium, silicon or sulfur atom (preferably oxygen, sulfur or 10 nitrogen). The expression heteroalkyl refers furthermore to a carboxylic acid or a group delved from a carboxylic acid, such as acyl, acylalkyl, alkoxycarbony, acyloxy, acyloxyalkyl, carboxyalkylamide or alkoxycarbonyloxy. Examples of heteroalkyl groups are groups of formulae R-O-Y-, R"-S-YO, R-N(Rb)-Y"-, 15 R"-CO-Y*-, R"-O-CO-Y"-, R-CO-O-Y"-, R-CO-N(R)-Y"-, R"-N(R)-CO-Y"-, R"-O-CO-N(R)-Y"-, R"-N(R)-CO-0-Y"-, R"-N(R)-CO-N(R"-Y"-, R"-0-CO-O-Y"-, R" -N(R)-C(=NR')-N(R")-Y"-, R-CS-Y"-, R"-O-CS-Y"-, R-CS-O-Y"-, R"-CS-N(R')-Y"-, R"-N(R')-CS-Y"-, R"-OCS-N(Rb)Y"B-, R"-N(R')-CS-0-Y"-, R"-N(R')-CS-N(R")-Y"-, R-O-CS-O-Y-, R"-S-CO-Y'-, R"-CO-S-Y-, R"-S-CO-N(R)-Y"-, R-N(Rb)CO-S-Y"-, 20 R"-S-CO-O-Y"-, R"O- CO-S-YR-, R-S-CO-S-Y"-, R-S-CS-Y"-, R"CS-S-Y"-, R-S-CS-N(R)-Y"-, R"-N(Rb)-CS-S-Y"-, R"-S-CS-O-Y"-, R"-O-CS-S-Y"-, whereby R" is a hydrogen atom, a C-C 6 -alkyl-, a C 2

-C

6 -alkenyl- or a C 2

-C

6 -alkynyl group; Rb is a hydrogen atom, a C-C 6 -alkyl-, a CrC 6 -alkenyl- or a C 2 -C6-alkynyl group; Rc is a hydrogen atom, a C-C 6 -alkyl-, a C 2

-C

6 -alkenyl- or a C 2

-C

8 -alkynyl group; Rd is a 25 hydrogen atom, a C-C 6 -alkyl-, a C 2 -Cs-alkenyl- or a C 2 -Ce-alkynyl group; and Ya is a direct bond, a C-Ce-alkylene, a C 2 -Cealkenylene or a C 2

-C

6 -alkynylene group, whereby each heteroalkyl group contains at least one carbon atom and one or more hydrogen atoms can be replaced by fluorine or chlorine atoms. Specific examples of heteroalkyl groups are methoxy, trifluoromethoxy, ethoxy, n-propyloxy, isopropyloxy, tert-butyloxy, 30 methoxymethyl, ethoxymethyl, methoxyethyl, methylamino, ethylamino, dimethylamino, diethylamino, iso-propylethylamino, methyl-aminomethyl, ethylaminomethyl, di-Iso propylaminoethyl, enolether, dimethylaminomethyl, dimethylaminoethyl, acetyl, propionyl, butyryloxy, acetyloxy, methoxycarbonyl, ethoxy-carbonyl, N-ethyl-N-methylcarbamoyl or N-methylcarbamoyl. Further examples of heteroalkyl groups are nitrile, isonitrile, 35 cyanate, thiocyanate, isocyanate, isothiocyanate and alkylnitrile groups.

4 The expression cycloalkyl refers to a saturated or partially unsaturated (e.g. cycloalkenyl: cyclic group, which contains one or more rings (preferably 1 or 2), with in particular 3 to 14 ring carbon atoms, preferably 3 to 10 (especially 3, 4, 5, 6 or 7) ring carbon atoms. The expression cycloalkyl further refers to groups in which one or more hydrogen atoms 5 are replaced by fluorine, chlorine, bromine or iodine atoms or -COOH, -OH, =0, -SH, =S, -NH 2 , =NH or -NO 2 groups, that is, for example, cyclic ketones such as cyclohexanone, 2-cyclohexenone or cyclopentanone. Further specific examples of cycloalkyl groups are the cyclopropyl, cyclobutyl, cyclopentyl, spiro[4,5]decanyl, norbomyl, cyclohexyl, cyclopentenyl, cyclohexadienyl, decalinyl, cubanyl, 10 bicyclo[4.3.0]nonyl, tetraline, cyclopentylcyclohexyl, fluorocyclohexyl or the cyclohex-2 enyl group. The expression heterocycloalkyl refers to a cycloalkyl group as defined above, in which one or more (preferably 1, 2 or 3) ring carbon atoms are replaced by an oxygen, 15 nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably oxygen, sulfur or nitrogen). A heterocycloalkyl group preferably possesses 1 or 2 rings with 3 to 10 (especially 3, 4, 5, 6 or 7) ring atoms. The expression heterocycloalkyl further refers to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine atoms or -COOH, -OH, =0, -SH, =S, -NH 2 , =NH or -NO 2 groups. Examples are 20 the piperidyl, morpholinyl, urotropinyt, pyrrolidiny, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydro-furyl, oxacyclopropyl, azacyclopropyl or 2-pyrazolinyl group, as well as lactams, lactones, cyclic imides and cyclic anhydrides. The expression alkylcycloalkyl refers to groups which, in accordance with the above 25 definitions, contain both cycloalkyl and alkyl, alkenyl or alkynyl groups, e.g. alkylcycloalkyl, alkylcycloalkenyl, alkenylcycloalkyl and alkynylcycloalkyl groups. An . alkylcycloalkyl group preferably contains a cycloalkyl group which has one or two rings with 3 to 10 (especially 3. 4, 5, 6 or 7) ring carbon atoms, and one or two alkyl, alkenyl or alkynyl groups with 1 or 2 to 6 carbon atoms. 30 The expression heteroalkylcycloalkyl refers to alkylcycloalkyl groups as defined above, in which one or more (preferably 1, 2 or 3) ring carbon atoms and/or carbon atoms are replaced by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably oxygen, sulfur or nitrogen). A heteroalkylcycloalkyl group preferably possesses 1 or 2 35 rings with 3 to 10 (especially 3, 4, 5, 6 or 7) ring atoms and one or two alkyl, alkenyl, alkynyl or heteroalkyl groups with 1 or 2 to 6 carbon atoms. Examples of such groups are 5 alkylheterocycloalkyl, alkytheterocycloalkeny, alkenylheterocycloalkyl, alkynylheterocycloalkyl, heteroalkylcycloalkyl, heteroalkylheterocycloalkyl and hetero alkylheterocycloalkenyl, whereby the cyclic groups are saturated or are mono-, di- or tri unsaturated. 5 The expression aryl or Ar refers to an aromatic group, which has one or more rings with in particular 6 to 14 ring carbon atoms, preferably 6 to 10 (especially B) ring carbon atoms. The expression aryl (or Ar) further refers to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine atoms or -COOH, 10 -OH, -SH, -NH 2 ,or -NO 2 groups. Examples are the phenyl, naphthyl, biphenyl, 2-fluorophenyl, anilinyl, 3-nitrophenyl or 4-hydroxyphenyl group. The expression heteroaryl refers to an aromatic group which contains one or more rings with in particular 5 to 14 ring atoms, preferably 5 to 10 (especially 5 or 6) ring atoms, and 15 one or more (preferably 1, 2,3 or 4) oxygen, nitrogen, phosphorus or sulfur ring atoms (preferably 0, S or N). The expression heteroaryl further refers to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine atoms or -COOH, -OH, -SH, -NH 2 or -NO 2 groups. Examples are 4-pyridyl, 2-imidazolyl, 3-phenylpyrrolyl, thiazolyt, oxazolyl, triazolyl, tetrazolyl, isoxazolyl, indazolyl, indolyl, 20 benzimidazolyl, pyridazinyl, quinolinyl, purnyl, carbazolyl, acridinyl, pyrimidyl. 2,3'-bifuryl, 3-pyrazolyl and isoquinolinyl groups. The expression aralkyl refers to groups which, in accordance with the above definitions, contain both aryl and alkyl, alkenyl, alkynyl and/or cycloalkyl groups, such as arylalkyl, 25 alkylaryl, arylalkenyl, arylalkynyl, arylcycloalkyl, arylcycloalkenyl, alkylarylcycloalkyl and alkylaryicycloalkenyl groups. Specific examples of aralkyls are toluene, xylene, mesitylene, styrene, benzyl chloride, o-fluorotoluene, 1H-indene, tetraline, dihydronaphthalene, indanone, phenylcyclopentyl, cumene, cyclohexylphenyl, fluorine and indane. An aralkyl group preferably contains one or two aromatic rings with 6 to 10 30 ring carbon atoms and one or two alkyl, alkenyl and/or alkynyl groups with 1 or 2 to 6 carbon atoms and/or a cycloalkyl group with 5 or 6 ring carbon atoms. The expression heteroaralkyl refers to an aralkyl group as defined above, in which one or more (preferably 1, 2, 3 or 4) ring carbon atoms and/or carbon atoms are replaced by an 35 oxygen, nitrogen, silicon, selenium, phosphorus, boron or sulfur atom (preferably oxygen, sulfur or nitrogen), i.e. it refers to groups which, in accordance with the above definitions, 6 contain both aryl or heteroaryl, and alkyl, alkenyl, alkynyl and/or heteroalkyl and/or cycloalkyl and/or heterocycloalkyl groups. A heteroaralkyl group preferably contains one or two aromatic rings with 5 or 6 to 10 ring carbon atoms and one or two alkyl, alkenyl and/or alkynyl groups with 1 or 2 to 6 carbon atoms and/or a cycloalkyl group with 5 or 6 5 ring carbon atoms, whereby 1, 2, 3 or 4 of these carbon atoms are replaced by oxygen, sulfur or.nitrogen atoms. Examples are arylheteroalkyi, arylheterocycloalkyl, arylheterocycloalkenyl, arylalkylheterocycloalkyl, arylalkenylheterocycloalkyl, arylalkynylheterocycloalkyl, aryl 10 alkylheterocycloalkenyl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl heteroarytheteroalkyl, heteroarylcycloalkyl, heteroarylcycloalkenyl, heteroarylhetero cycloalkyl, heteroarylheterocycloalkenyl, heteroaryalkylcycloalkyl, heteroarylakyheterocycloalkenyl, heteroarylheteroalkylcycloalkyl, heteroaryiheteroalkyl cycloalkenyl and heteroarylheteroalkylheterocydoalkyl groups, whereby the cyclic groups 15 are saturated or are mono- di- or tr-unsaturated. Specific examples are the tetrahydro .isoquinolinyl, benzoyl, 2- or 3-ethylindolyl, 4-methylpyridino, 2-, 3- or 4-methoxyphenyl, 4-ethoxyphenyl, 2-, 3- or 4-carboxyphenylalkyl group. The expressions cycloalkyl, hereocycloalkyl, alkylcyclo-alkyl, heteroalkylcycloalkyl, aryl, 20 heteroaryl, aralkyl and heteroaralkyl further refer to groups In which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine atoms or OH, =0, SH, =S, NH 2 , =NH or NO 2 groups. The expression "optionally substituted" refers to groups in which one or more hydrogen 25 atoms are replaced e.g. by fluorine, chlorine, bromine or Iodine atoms or -COOH, -OH, =0, -SH, =S, -NH 2 , =NH or -NO 2 groups. This expression further refers to groups that are substituted by unsubstituted C-Ce alkyl, C 2- Ce alkeny, CrCe alkynyl, C-C 6 heteroalkyl, CrCo cycloalkyl, C 2 -C, heterocycloalkyl, Cg-C 10 aryl, C-C, heteroaryl, CrC,2 aralkyl or CrCjj heteroaralkyl groups. 30 Compounds of formula (I) may contain one or more centres of chirality depending on their substitution. The present invention therefore Includes both all pure enantiomers and all pure diastereoisomers, and their mixtures in any ratio. In addition, the present invention also includes all cis/trans isomers of the compounds of the general formula (I) 35 as well as mixtures thereof. In addition, the present invention includes all tautomeric forms of the compounds of formula (I).

WO 2006/114261 PCT/EP2006/003765 7 Preference is given to compounds of formula (1), whereby W is NH and V is 0, S or NH, Further preference is given to compounds of formula (I), whereby one, two or three of 5 groups D, G and M are nitrogen atoms. Particular preference is given to compounds of formula (1), whereby X is a group of formula -CH 2 -CO-NHOH, -CO-NHOH, -CH 2 -NOH-CHS, -NOH-CHS, -CHrNOH-CHO, -NOH-CHO, -CHrCO-CH 2 OH, -CO-CH 2 OH, -CHrCHOH-CHO, -CHOH-CHO or a group 10 having one of the following formulae: H H N NN N-N N-N X is most preferably a group of formula -CO-N HOH. 15 In addition, R' is preferably a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group or an ethyl group; especially a hydrogen atom or an amino group.

R

2 is more preferably a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or an ethyl group; especially a hydrogen atom. 20 Furthermore, R 3 and R 4 are preferably not hydrogen atoms at the same time.

R

3 is more preferably a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group, an ethyl group or a propyl group, especially a chlorine atom, a 25 bromine atom or an amino group.

R

4 is, in turn, preferably a chlorine atom, a bromine atom, a methyl group, an ethyl group or a propyl group; especially a chlorine atom or a bromine atom. 30 Compounds of formula (1), in which R 3 is a bromine atom and R 4 is a methyl group, or in which R 3 is a hydrogen atom and R 4 is a chlorine atom or a bromine atom, are especially preferred.

8 More preferably, two of radicals R', R 2 , R and R4 together are part of a cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring, whereby each of these rings may optionally be substituted. 5 Rs is, in tum, preferably a tert.-butyl group, an Isopropyl group, a neopentyl group or a n-hexyl group; especially a tert-butyl, neopentyl or n-hexyl group. More preferably, the groups Re and R', independently of one another, are hydrogen 10 atoms, hydroxymethyl or methyl groups. Examples of pharmacologically acceptable salts of compounds of formula (1) are salts of physiologically acceptable mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid; or salts of organic acids, such as methanesulfonlc acid, p-toluene 15 sulfonic acid, lactic acid, formic acid, acetic acid, trifluoroacetic acid, citric acid, succinic acid, fumaric acid, maleic acid and salicylic acid. Compounds of formula (I) may be solvated, in particular hydrated. Hydration may arise e.g. during the preparation process or as a consequence of the hygroscopic nature of the Initially water-free compounds of formula (I). 20 The pharmaceutical compositions according to the present invention contain at least one compound of formula (1) as active ingredient and optionally carriers and/or adjuvants. The prodrugs (for definition and examples see e.g. R. B. Silverman, Medizinische 25 Chemie, VCH Weinheim, 1995, chapter 8, pp 381ff), which are likewise an object of the present invention, consist of a compound of formula (1) and at least one pharmacologically acceptable protecting group, which is cleaved under physiological conditions, e.g. a hydroxy, alkoxy, aralkyloxy, acyl or acyloxy group, such as a methoxy, ethoxy, benzyloxy, acetyl or acetyloxy group. 30 The therapeutical usage of the compounds of formula (I), their pharmacologically acceptable salts or solvates and hydrates, as well as formulations and pharmaceutical compositions, is likewise an aspect of the present invention. 35 Compounds of formula (1) are of great interest especially as inhibitors of metalloproteinases (in particular PDF). The usage of these active ingredients in the CfIatDCCKZL.N742WI DOfC-ZMS210 -9 production of medicaments to prevent and/or treat diseases, especially those conveyed by PDF, is also an aspect of the present invention. In general, compounds of formula (I) are administered using known, acceptable methods, either singly or in combination with any other therapeutic agent. Administration may be effected e.g. In one of the following ways: orally, e.g. as drag6es, coated tablets, pills, semi-solids, soft or hard capsules, solutions, emulsions or suspensions; parenterally, e.g. as an injectable solution; rectally as suppositories; by Inhalation, e.g. as a powder formulation or pray, transdermally or Intra-nasally. To produce such tablets, pills, semi-solids, coated tablets, dragees and hard gelatin capsules, the therapeutically employable product may be mixed with pharmacologically [nert, inorganic or organic carrers for medicaments, e.g. with lactose, sucrose, glucose, gelatin, malt, silica gel, starch or derivatives thereof, talc, stearic acid or salts thereof, dry skimmed milk and the like. To produce soft capsules, clriers for medicaments, such as vegetable oils, petroleum, animal or synthetic oils, wax, fat, polyols, may be used. To produce liquid solutions and syrups, carriers for medicaments, such as water, alcohols, aqueous salt solution, aqueous dextrose, polyols, glycerol, vegetable oils, petroleum, animal or synthetic oils, may-be used. For suppositories, cariers for medicaments, such as vegetable oils, petroleum, animal or synthetic oils, wax, fat and polyols, may be used. For aerosol formulations, compressed gases that are appropriate for this purpose may be used, such as oxygen, nitrogen and carbon dioxide. The pharmaceutically acceptable agents may also contain preserving and stabilizing additives, emulsifiers, sweeteners, aromatic, salts to modify the osmotic pressure, buffers, coating additives and antioxidants. In another aspect, the present Invention relates to a use of a compound of the present invention or a pharmaceutical composition of the present invention for the Inhibition of metalloproteinases. In a further aspect, the present invention relates to a use of a compound of the present invention or a pharmaceutical composition of the present invention for the inhibition of peptide deformylase (PDF). In another aspect, the present invention relates to a use of a compound of the present C\NRPofrtnDCC\KZL\274291 _DOC-2/25/2010 - 9A invention or a pharmaceutical composition of the present invention in the prevention and/or treatment of diseases conveyed by metalloproteinase activity. In a further aspect, the present invention relates to a use of a compound of the present 5 invention or a pharmaceutical composition of the present invention in the prevention and/or treatment of diseases conveyed by peptide deformylase (PDF) activity. In another aspect, the present invention relates to a use of a compound of the present invention or a pharmaceutical composition of the present invention as an antibiotic. 10 In a further aspect, the present invention relates to a use of a compound of the invention in the manufacture of a medicament for the treatment and/or prevention of diseases conveyed by metalloproteinase activity. 15 In another aspect, the present invention relates to a method of treating and/or preventing diseases conveyed by metalloproteinase activity, comprising administering to a subject in need thereof a compound of the present invention. In a further aspect, the present invention relates to a use of a compound of the present 20 invention in the manufacture of a medicament for the treatment and/or prevention of bacterial infections. In another aspect, the present invention relates to a method of treating and/or preventing bacterial infections, comprising administering to a subject in need thereof a compound of 25 the present invention. Compounds of formula (1) with X = -COOCH 3 may be produced by reacting compounds of formulae (II), (1II) and (IV.

C.%NRPo flCCJWZLU7429S0)2 DOC-2iSIMEIO - 9B NH 2 Ni;H'R

H

3 C ) NC

HRR

WO 2006/114261 PCT/EP2006/003765 10 By reacting the reaction product with hydroxylamine in methanol, compounds of formula (I) with X = -CO-NHOH may be produced. Examples 5 General procedure: 50 pl of a 0.2 M solution of amine (11) in methanol were dispensed onto a 96-well plate (amines that are insoluble in methanol were dispensed manually). 50 pl of a 0.2 M solution of the aldehyde (lli) in methanol were added. The plate was shaken for 2 h at 10 room temperature. Subsequently, 50 pl of a 0.2 M solution of the isocyanide (IV) in methanol and 50 pl of a 0.4 M acetic acid solution in methanol were dispensed. The plate was shaken over night at room temperature, the solvent evaporated, and the residue dissolved in 150 pl of a 0.5 M NH 2 OH solution in methanol. The plate was again shaken over night at room temperature. 15 The following compounds were produced in accordance with the general procedure, using appropriate starting materials, and were identified by mass spectrometry. All compounds were investigated for their activity as PDF inhibitors (for the assay, see D. Chen et al. Antimicrobial Agents and Chemotherapy, Jan. 2004, pp. 250-261) and had 20 IC 50 values ranging between I nmol and 50 pmol. found Examples calc. [M+HI (M+H] 2-(6-fluoro-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 225.09 225.08 2-(6-bromo-8-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 299.03 299.04 2-(6-bromo-3,5-dimethyl-imidazo[1,2-ajpyridin-2-ylamino)-N hydroxy-acetamide 313.05 313.08 N-hydroxy-2-(6-iodo-3-isobutyl-imidazo[1,2-a]pyridin-2-ylamino) acetamide 389.07 389.10 2-(6-bromo-3,5-dimethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-propionamide 327.07 . 327.10 2-(3-tert-butyl-6-iodo-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 389.07 389.11 WO 2006/114261 PCT/EP2006/003765 11 2-(6-bromo-3-ethyi-5-methy-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 327.07 327.10 -(6-chloro-3-cyclopropyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-propionamide 295.12 295.14 2-(6-chloro-3-isopropyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-propionamide 297.14 297.18 2-(6-bromo-3-ethyl-5-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-propionamide 341.09 341.12 -(6-bromo-3-isopropyl-5-methyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 341.09 341.12 2-[6-bromo-5-methyl-3-((E)-propenyl)-imidazo(1,2-a]pyridin-2 lamino]-N-hydroxy-acetamide 339.07 339.11 2-(6-chloro-3-isobutyl-imidazo[1,2-apyridin-2-ylamino)-N hydroxy-acetamide 297.14 297.17 2-(3-tert-butyl-6-chloro-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 297.14 297.16 2-(3-tert-butyl-6-chloro-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-propionamide 311.16 311.23 2-(3-tert-butyl-6-fluoro-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 281.17 281.15 2-(6-fuoro-3-isobutyl-imidazo(1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 281.17 281.19 N-hydroxy-2-(3-isobutyl-5-methyl-imidazo[1,2-alpyridin-2 lamino)-acetamide 277.20 277.21 -(6-bromo-5-methyl-3-propyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 341.09 341.12 2-(6-bromo-3-isobutyl-5-methyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 355.11 355.14 -(3-tert-butyl-6-methyl-imidazo[1,2-a]pyrdin-2-ylamino)-N hydroxy-acetamide 277.20 277.20 N-hydroxy-2-(6-iodo-3-isobutyl-imidazo(1,2-a]pyridin-2-ylamino) propionamide 403.09 403.12 2-(6-bromo-8-methyl-3-propyl-imidazol,2-a)pyridin-2-ylamino) N-hydroxy-propionamide 355.11 355.08 2-(6-bromo-3-tert-butyl-5-methyl-imidazo[1,2-a]pyridin-2- 355.11 355.13 WO 2006/114261 PCT/EP2006/003765 12 2-(6chloro-3-propy-imlidazo[l ,2-a~pyridin-2-ylamfiflo)-N-hydroxy proponaide297.14 297.16 hydroxy-propiolamlide 291.22 291.22 -(6-chloro-3-isobutyI-imidazoI1 ,2-a~pyrndin-2-ylamiflo)-N hydroxy-propionamide 311.16 311.17 2-(6-bromo-5-methy-3-propyI-imfidazo[l ,2-a]pyridil-2-ylailo) Whydroxy-propioflamide 355.11 355.13 ylaino-N-ydrxy-roponaide369,13 369.16 2-6boo3isbt 8mthliio 1 2-a~pyridin-2-ylamfiflo) N-hydroxy-propioflamide 369,13 369.15 2-(6-bromo-3-isobutyl-5-methyI-imidazo[l ,2-a~pyridifl-2-ylamiflo) N-hydroxy-propioflamlide 369.13 369.15 N-yrx--3hyrxmty -mty-mdz[,2-a]pyridin-2 Ilamino)-acetamide 251.14 251.15 2-(5-ethyl-3-hydroxymethyI-imidazo[l ,2-a]pyridin-2-yailo)-N hydroxy-acetamide 265.16 265.17 2-(5-ethyI-3-methy-imidazo[1 ,2-a]pyridin-2-ylamilo)-N-hydroxy- 24.6 491 cetamide24.6 491 N-hydroxy-2-[3-(1 H-imidazol-2-yI)-5-mlethy-imlidazo[l ,2 a]pyridin-2-ylamiflo]-acetamide 287.15 287.16 2-(3,5-diethyl-imidazoll ,2-a~pyridin-2-yamilo)-N-hydroxy-26.8 631 acetamide26.8 631 N-hdroy-aetaide301.16 301.18 2-(5-ethyI-3-hydroxymethyl-imidazo[l ,2-a]pyridin-2-ylamiflo)-N- 27.7 796 2-[5-ethyI-3-((E)-propel)-imfidazofl ,2-a]pyridin-2-ylamilo]-N- 27.8 00 hydroxy-acetamide 275.18__ 0.00__ N-hydroxy-acetamlide 301.16 301.18 r (3-furan-2-yl-5-methyl-imidazo[1 ,2-a~pyridin-2-ylaminlo)-N- 28.3 871 hydroxy-acetamide 287.13_ _____ WO 2006/114261 PCT/EP2006/003765 13 N-nydroxy-2-[8-methyl-3-( 1 H-pyrazol-3-yJ)-imidazo[1 .2-alpyridin 2-ylamino]-acetamide 287.15 287.16 2-(3-cyclopropyl-5-ethyl-imidazo[1 ,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 275.18 275.18 N-hydroxy-2-(8-hydmxy-3-methyl-imidazo[1 ,2-a]pyridin-2 Ifamino)-3-phenyl-propionamide 327.17 327.10 N-hydroxy-2-(5-methyl-3-pheny-imidazo[1 ,2-a]pyridin-2 Ilamino)-acetamide 297.16 297.17 N-hydroxy-2-(7-methyl-imidazo[1 ,2-a]pyridin-2-ylaminb)-3 phenyl-propionamide 311.18 311.15 2-(3-butyI-5-propyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 305.24 305.22 ..(3-ethyl-5-propyl-imidazo[1 ,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 277.20 277.19 N-hydroxy-2-(3-isobutyl-5-propyl-imidazo[1 ,2-a]pyridin-2 y!amino)-acetamide 305.24 305.14 N-hydroxy-2-(3-hydroxymethyl-5-propy-iidazo[1 1 2-a]pyridin-2 ylamino)-acetamide 279.17 279.17 2-(3-benzyl-5-propyl-imidazo[1 ,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 339.22 339.22 N-hydroxy-2-(3-pentyl-5-propy-imidazo[l ,2-a]pyridin-2-ylamino) acetamide 319.26 319.25 N-hydroxy-2-(3-methyl-5-propyl-imidazo[l,2-a]pyridin-2 Ifamino)-acetamide 263.18 263.17 3-[2-(hydroxycarbamoylmethyl-amino)-5-propy-iidazo[1 ,2 a]pyridin-3-yl]-propionic 32 1.19 321.18 2-(3,5-dipropyl-imidazoll ,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 291.22 291.21 N-hydroxy-2-[3-(2-methylsufany-ethy)-5-propy-imidazo[1 ,2 a]pyridin-2-ylamino]-acetamide 323.19 323.18 2-(3-tert-butyl-5-propyl-imidazo[1 ,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 305.24 305.22 2-(3-(2,2-dimethyl-propyl)-5-propy-imidazo[1 ,2-a]pyridin-2 lamino]-N-hydroxy-acetamide 319.26 319.25 -(3-hept-1 -inyl-5-propyl-imidazo[l 1 2-a]pyridin-2-ylamino)-N- 343.26 343.25 WO 2006/114261 PCT/EP2006/003765 14 hydroxy-acetamide N-hydroxy-2-(3-pentyl-6-trifluoromethyl-imidazo[1,2-a]pyridin-2 yiamino)-acetamide 345.18 345.20 -[3-(2,2-dimethyl-propyl)-6-trifluoromethyl-imidazo[,2-a]pyrdin 2-ylamino]-N-hydroxy-acetamide 345.18 345.20 2-(3-hept-1-inyl-6-trifluoromethyl-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 369.18 369.11 2-(6-fluoro-3-pentyl-imidazo[1,2-alpyridin-2-ylamino)-N-hydroxy acetamide 295.19 295.20 2-[32(2,2-dimethyl-propyl)-6-fluoro-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 295.19 295.19 2-(3-butyl-5-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 277.20 277.19 2-(3-benzyl-5-methyl-imidazo[l,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 311.18 311.19 N-hydroxy-2-(5-methyl-3-pentyl-imidazo[l,2-alpyrdin-2 ylamino)-acetamide 291.22 291.22 N-hydroxy-2-[5-methyl-3-(2-methylsulfanyl-ethyl)-imidazo[1,2 a]pyridin-2-ylamino]-acetamide 295.15 295.09 2-(3-tert-butyl-5-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 277.20 277.21 2-[3-(2,2-dimethyl-propyl)-5-methyl-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 291.22 291.22 -(3-hept-1-inyl-5-methyl-imidazo[1,2-a]pyridin-2-yamino)-N hydroxy-acetamide 315.22 315.23 2-(1 -butyl-imidazo[1,2-a]quinolin-2-ylamino)-N-hydroxy- 3 cetamide 313.20 313.21 2-(1 -benzyl-imidazoL 1,2-a]quinolin-2-ylamino)-N-hydroxy acetamide 347.18 347.20 N-hydroxy-2-(1-pentyl-imidazo[1,2-a]quinolin-2-yamino) acetamide 327.22 327.23 N-hydroxy-2-(1-propyl-imidazo[1,2-a]quinolin-2-ylamino) acetamide 299.18 299.21 N-hydroxy-2-[1-(2-methylsulfanyl-ethyl)-imidazo[1,2-a]quinolin-2 ylamino]-acetamide 331.15 331.18 WO 2006/114261 PCT/EP2006/003765 15 1 f 2-(1 -tert-butyl-imidazo[1,2-a]quinolin-2-ylamino)-N-hydroxy acetamide 313.20 313.21 2-[1-(2,2-dimethyl-propyl)-imidazo[1,2-a]quinolin-2-ylamino]-N hydroxy-acetamide 327.22 327.23 2-(1-hept-1-inyl-imidazo[1,2-a]quinolin-2-ylamino)-N-hydroxy acetamide 351.22 351.23 2-(6-bromo-3-isobutyl-8-methyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 355.11 355.03 2-[6-bromo-3-(2,2-dimethyl-propyl)-8-methyl-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 369.13 369.15 2-(6-bromo-3-hept-1-inyl-8-methyl-imidazo[1,2-a]pyridin-2 yIamino)-N-hydroxy-acetamide 393.13 393.14 2-(6-chloro-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 311.16 311.17 2-[6-chloro-3-(2,2-dimethyl-propyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 311.16 311.17 2-(6-chloro-3-hept-1-inyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 335.16 335.17 2-(3-butyl-6-nitro-irnidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 308.16 308.15 N-hydroxy-2-(3-isobutyl-6-nitro-imidazo[1,2-a]pyridin-2-ylamino) acetamide 308.16 308.11 2-(3-benzyl-6-nitro-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 342.14 342.17 N-hydroxy-2-(6-nitro-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino) acetamide 322.18 322.19 2-[3-(2,2-dimethyl-propyl)-6-nitro-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 322.18 322.20 2-(3-hept-1-inyl-6-nitro-imidazo(1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 346.18 346.20 2-(3-butyl-6-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 277.20 277.18 N-hydroxy-2-(6-methyl-3-pentyl-imidazo[1,2-a]pyridin-2 ylamino)-acetamide 291.22 291.22 2-[3-(2,2-dimethyl-propyl)-6-methyl-imidazo[1,2-a]pyridin-2- 291.22 291.22 WO 2006/114261 PCT/EP2006/003765 16 Iylamino)-N-hydroxy-acetamide 2-(3-hept-1-inyl-6-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 315.22 315.22 2-(3-butyl-5,7-dimethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 291.22 291.23 N-hydroxy-2-(3-isobutyl-5,7-dimethyl-imidazo[1,2-a]pyridin-2 ylamino)-acetamide 291.22 291.21 N-hydroxy-2-(3-hydroxymethyl-5,7-dimethyl-imidazo[1,2 a]pyridin-2-ylamino)-acetamide 265.16 265.16 2-(3-benzyI-5,7-dimethyl-imidazo[l,2-a)pyridin-2-ylamino)-N hydroxy-acetamide 325.20 325.21 2-(5,7-dimethyl-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 305.24 305.24 3-[2-(hydroxycarbamoylmethyl-amino)-5,7-dimethyl-imidazo[1,2 a]pyridin-3-y]-propionic 307.17 307.10 2-(5,7-dimethyl-3-propyl-imidazol,2-a]pyridin-2-yamino)-N hydroxy-acetamide 277.20 277.26 2-[5,7-dimethyl-3-(2-methylsulfanyl-ethyl)-imidazo[1,2-a]pyridin 2-ylamino]-N-hydroxy-acetamide 309.17 309.18 2-(3-tert-butyl-5,7-dimethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 291.22 291.22 2-[3-(2,2-dimethyl-propyl)-5,7-dimethyl-imidazo[1,2-a]pyridin-2 lamino]-N-hydroxy-acetamide 305.24 305.24 2-(3-hept-1-inyl-5,7-dimethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 329.24 329.24 2-(6,8-dibromo-3-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 419.00 419.03 2-(6,8-dibromo-3-isobutyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 419.00 419.03 2-(6,8-dibromo-3-hydroxymethyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 392.93 393.00 2-(3-benzyl-6,8-dibromo-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 452.97 453.02 2-(6,8-dibromo-3-pentyl-imidazo(1,2-alpyridin-2-ylamino)-N hydroxy-acetamide 433.02 433.05 WO 2006/114261 PCT/EP2006/003765 17 2-[6, -ibromo-3-(2-methylsulfanyl-ethyl)-imidazo[1,2-alpyridin 2-yiamino]-N-hydroxy-acetamide 436.95 436.97 -[6,8-dibromo-3-(2,2-dimethyl-propyl)-imidazo[1,2-a]pyridin-2 yiamino]-N-hydroxy-acetamide 433.02 433.02 2-(6,8-dibromo-3-hept-1-iny-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 457.01 457.03 2-(3-butyl-8-chloro-6-trifluoromethyl-imidazo[1,2-a]pyridin-2 yIamino)-N-hydroxy-acetamide 365.12 365.14 -(8-chloro-3-hydroxymethyl--trifluoromethyl-imidazo[1,2 a]pyridin-2-ylamino)-N-hydroxy-acetamide 339.06 339.03 2-(3-benzyl-8-chloro-6-trifluoromethyl-imidazo[1,2-alpyridin-2 lamino)-N-hydroxy-acetamide 399.10 399.15 2-(8-chloro-3-pentyl-6-trifluoromethyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 379.14 379.15 2-[8-chloro-3-(2,2-dimethyl-propyl)-6-trifluoromethyl-imidazo[1,2 a]pyrdin-2-ylamino]-N-hydroxy-acetamide 379.14 379.15 2-(8-chloro-3-hept-1-inyl-6trfluoromethyl-imidazo(1,2-a]pyridin 2-ylamino)-N-hydroxy-acetamide 403.14 403.14 2-(6-bromo-3-isobutyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 341.09 341.09 2-(6-bromo-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 355.11 355.10 2-(6-bromo-3-tert-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 341.09 341.09 2-[6bromo-3-(2,2-dimethyl-propyl)-imidazo[l,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 355.11 355.11 2-(6-bromo-3-hept-1-inyl-imidazo[1,2-a7pyridin-2-ylamino)-N hydroxy-acetamide 379.11 379.12 2-(1-butyl-9-hydroxy-imidazo[1,2-a]quinolin-2-ylamino)-N hydroxy-acetamide 329.19 329.19 2-(1-ethyl-9-hydroxy-imidazo[1,2-a]quinolin-2-ylamino)-N hydroxy-acetamide 301.15 301.16 N-hydroxy-2-(9-hydroxy-1-isobutyl-imidazo[1,2-a]quinolin-2 ylamino)-acetamide 329.19 329.19 2-(1-benzyi-9-hydroxy-imidazo[1,2-a]quinolin-2-ylamino)-N- 363.17 363.18 WO 2006/114261 PCT/EP2006/003765 18 hydroxy-acetamide N-hydroxy-2-(9-hydroxy-1 -pentyl-imidazo[1 ,2-alquinolin-2 ylamino)-acetamide 343.21 343.21 N-hydroxy-2-(9-hydroxy-1 -propyl-imidazo[1 ,2-ajquinolin-2 Ilamino)-acetamide 315.17 315.17 N-hydroxy-2-[9-hydroxy-1 -(2-methylsufany-ethyl)-imidazo[l ,2 a]quinolin-2-yamino]-acetamide 347.14 347.15 2-(1 -tert-butyl-9-hydroxy-imidazo[1 ,2-a]quinolin-2-ylamiflo)-N hydroxy-acetaniide 329.19 329.19 ylamno]N-hdroy-aetaide343.21 343.21 2-(8-bromo-3-buty-6-methy-iidazo[1 ,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 355.11 355.11 -(8-bromo-6-methyI-3-pelty-imidazo(l ,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 369.13 369.12 2-8boo3(,-iehl rpl-mty-mdz[,2 a]pyddin-2-ylamino]-N-hydroxy-aetamide 369.13 369.12 2-(8-bromo-3-hept-1 -inyl-6-methyl-imidazo[1 ,2-a]pyridin-2 ylamino)-N-hydroxy-acetamlide 393.13 393.13 -(3-butyl-5-chlor-o-imidazo[1 ,2-a]pyridin-2-ylamino)-N-hydroxy cetamide 297.14 297.14 2-(5-chloro-3-ethyl-ihidazo[1 ,2-ajpyridin-2-ylamilo)-N-hydroxy cetamide 269.10 269.14 2-(5-chloro-3-isobutyl-imidazo[1 ,2-a]pyridin-2-ylamiflo)-N hydroxy-acetamide 297.14 297.14 2-(5-chloro-3-hydroxymethyI-imidazo[1 ,2-alpyridin-2-ylamino)-N hydroxy-acetamide 271 .07 271.09 2-(3-benzy-5-chloro-imidazo[1 ,2-a]pyridin-2-ylamiflo)-N hydroxy-acetamide 33 1.12 331.13 2-(5-chloro-3-pentyl-imidazofl ,2-ajpyridin-2-ylamilo)-N-hydroxy acetamide 311.16 311.16 -(5-chloro-3-methy-imidazo[1 ,2-alpyridin-2-ylamilo)-N hydroxy-acetamide 255.08 255.09 3-[5-choro-2-(hydroxycarbamoylmethyI-amiflo)-imidazo[l ,2 r]pyridin-3-y]-propioflic 313.09 313.13 WO 2006/114261 PCT/EP2006/003765 19 2-(5-chloro-3-propyl-imidazo[1,2-a]pyrdin-2-ylamino)-N-hydroxy acetamide 283.12 283.18 2-[5-chloro-3-(2-methylsulfanyl-ethyl)-imidazo[1,2-a]pyridin-2 yIamino]-N-hydroxy-acetamide 315.09 315.10 2-(3-tert-butyl-5-chloro-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 297.14 297.14 2-[5-chloro-3-(2,2-dimethyl-propyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 311.16 311.16 2-(5-chloro-3-hept-1-iny-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 335.16 335.17 N-hydroxy-2-(5-methyl-6-nitro-3-propyl-imidazo[1,2-a]pyridin-2 ylamino)-acetamide 308.16 308.14 2-[3-(2,2-dimethyl-propyl)-5-methyl-6-nitro-imidazo[1,2-a]pyridin 2-ylamino]-N-hydroxy-acetamide 336.20 336.25 2-(5-bromo-3-propyl-imidazo[1,2-b]isoquinolin-2-ylamino)-N hydroxy-acetamide 377.09 377.13 2-[5-bromo-3-(2-methylsulfanyI-ethyl)-imidazo[l,2-b]isoquinolin 2-ylamino]-N-hydroxy-acetamide 409.06 409.08 2-(6,8-dibromo-3-butyl-5-lmethyl-imidazo[1,2-a]pyrdin-2 ylamino)-N-hydroxy-acetamide 433.02 433.05 2-(6,8-dibromo-3-ethyl-5-methyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 404.98 405.00 2-(6,8-dibromo-3-isobutyl-5-methyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 433.02 433.03 2-(6,8-dibromo-3-hydroxymethyl-5-methyl-imidazo[1,2-a]pyridin 2-ylamino)-N-hydroxy-acetamide 406.95 406.98 2-(3-benzyl-6,8-dibromo-5-methyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 466.99 466.96 2-(6,8-dibromo-5-methyl-3-pentyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 447.03 447.04 2-(6,8-dibromo-3,5-dimethyl-imidazo[1,2-a]pyridin-2-yamino)-N hydroxy-acetamide 390.96 390.98 2-(6,8-dibromo-5-methyl-3-propyl-imidazo[1,2-a]pyrdin-2 ylamino)-N-hydroxy-acetamide 419.00 419.01 2-[6,8-dibromo-5-methyl-3-(2-methylsulfanyl-ethyl)-imidazo[1,2- 450.97 451.02 WO 2006/114261 PCT/EP2006/003765 20 a]pyridin-2-ylamino]-N-hydroxy-acetamide 2-[6,8-dibromo-3-(2,2-dimethyl-propyl)-5-methyl-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 447.03 447.05 2-(6,8-dibromo-3-hept-1-inyl-5-methyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 471.03 471.08 -(1-butyl-5-hydroxy-imidazo[1,2-a]quinolin-2-ylamino)-N hydroxy-acetamide 329.19 329.20 N-hydroxy-2-(5-hydroxy-l-isobutyl-imidazo[1,2-a]quinolin-2 lamino)-acetamide 329.19 329.20 2-(1-benzyl-5-hydroxy-imidazo[1,2-a]quinolin-2-ylamino)-N hydroxy-acetamide 363.17 363.17 N-hydroxy-2-(5-hydroxy-l-pentyl-imidazo[1,2-a]quinolin-2 amino)-acetamide 343.21 343.19 N-hydroxy-2-(5-hydroxy--propyl-imidazo[1,2-a]quinolin-2 lamino)-acetamide 315.17 35.23 N-hydroxy-2-[5hydroxy-l-(2-methylsulfanyI-ethyl)-imidazo[1,2 ]quinolin-2-ylamino]-acetamide 347.14 347.15 2-[1-(2,2-dimethyl-propyl)-5-hydroxy-imidazol,2-a]quinolin-2 ylamino]-N-hydroxy-acetamide 343.21 343.21 2-(3-butyl-6,8-difluoro-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 299.16 299.16 -(6,8-difluoro-3-isobutyl-imidazo[1,2-a]pyridin-2-ylamino)-N nydroxy-acetamide 299.16 299.16 2-(6,8-difluoro-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 313.18 313.18 2-[6,8-difluoro-3-(2-methylsulfany-ethyl)-imidazo[1,2-a]pyridin-2 yiamino]-N-hydroxy-acetamide 317.11 317.12 2-[3-(2,2-dimethyl-propyl)-6,8-difluoro-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 313.18 313.18 2-(6-bromo-3-isobutyl- 7 ,8-dimethyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 369.13 369.13 2-(6-bromo-7,8-dimethyl-3-pentyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 383.15 383.14 2-[6-bromo-3-(2,2-dimethyl-propyl)-7,8-dimethyl-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 383.15 383.14 WO 2006/114261 PCT/EP2006/003765 21 2-(6-bromo-3-hept-i-inyi-7,8-dimethyl-irnidazo[1,2-alpyridin-2 yfamino)-N-hydroxy-acetamide 407.15 407.15 2-[3-(2,2-dimethyl-propyl)-7-methyl-6-nitro-imidazo[1,2-a]pyridin 2-ylamino)-N-hydroxy-acetamide 336.20 336.21 2-(5-bromo-3-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 341.09 341.09 2-(5-bromo-3-ethyl-imidazo[1,2-a]pyridin-2-yamino)-N-hydroxy acetamide 313.05 313.06 2-(5-bromo-3-isobutyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 341.09 341.10 2-(5-bromo-3-hydroxymethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 315.02 315.04 2-(3-benzyl-5-bromo-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 375.07 374.98 2-(5-bromo-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 355.11 355.06 2-(5-bromo-3-methyl-imidazo(1,2-alpyridin-2-ylamino)-N hydroxy-acetamide 299.03 299.04 3-[5-bromo-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 a]pyridin-3-yi]-propionic 357.04 357.06 2-(5-bromo-3-propyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 327.07 327.07 2-[5-bromo-3-(2-methylsulfanyl-ethyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 359.04 359.06 2-(5-bromo-3-tert-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 341.09 341.17 2-[5-bromo-3-(2,2-dimethyl-propyl)-imidazo[1,2-a]pyridin-2 yIamino]-N-hydroxy-acetamide 355.11 355.11 2-(5-bromo-3-hept-1-inyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 379.11 379.12 2-(3-butyl-8-ethyl-5-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 305.24 305.23 2-(8-ethyl-3-hydroxymethyl-5-methyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 279.17 279.18 2-(3-benzyl-8-ethyl-5-methyl-imidazo[1,2-a]pyridin-2-ylammno)-N- 339.22 339.22 WO 2006/114261 PCT/EP2006/003765 22 hydroxy-acetamide 2-(8-ethyl-5-methyl-3-pentyl-imidazo(1 ,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 319.26 319.25 2-[3-(2,2-dimethyl-propyl)-8-ethyl-5-methyl-imidazo[1,2-a]pyridin 2-ylamino]-N-hydroxy-acetamide 319.26 319.25 -(8-ethyl-3-hept-1-inyl-5-methyl-imidazo[1,2-a]pyrdin-2 ylamino)-N-hydroxy-acetamide 343.26 343.26 2-(6,8-dichloro-3-hydroxymethyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 305.03 305.06 2-(6,8-dichloro-3-pentyl-imidazo[l,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 345.12 345.12 2-(6-bromo-3-isobutyl-7-methyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 355.11 355.11 2-[6-bromo-3-(2,2-dimethyl-propyl)-7-methyl-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 369.13 369.12 2-(3-butyl-5-ethyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 291.22 291.22 2-(5-ethyl-3-isobutyi-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 291.22 291.21] 2-(5-ethyl-3-pentyl-imridazo[1,2-alpyridin-2-ylamino)-N-hydroxy acetamide 305.24 305.23 3-[5-ethyl-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 a]pyridin-3-y]-propionic 307.17 307.17 2-(5-ethyl-3-propyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 277.20 277.19 2-[5-ethyl-3-(2-methylsulfanyl-ethyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 309.17 309.18 2-(3-tert-butyl-5-ethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 291.22 291.22 2-[3-(2,2-dimethyl-propyl)-5-ethyl-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 305.24 305.24 2-(5-ethyl-3-hept-1-inyl-imidazo[1,2-a]pyrdin-2-ylamino)-N hydroxy-acetamide 329.24 329.24 S-(6-bromo-3-butyl-5-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N ydroxy-acetamide 355.11 355.11 WO 2006/114261 PCT/EP2006/003765 23 2-(3-benzy6-bromo-5-flmethyi-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 389.09 389.06 -(6-bromo-5-methyl-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 369.13 369.13 3-[6-bromo-2-(hydroxycarbamoylmethyl-amino)-5-methyl midazo[1,2-a]pyridin-3-yl]-propionic 371.06 371.10 2-[6-bromo-5-methyl-3-(2-methylsulfanyl-ethyl)-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 373.06 373.08 2-[6-bromo-3-(2,2-dimethyl-propyl)-5-methyl-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 369.13 369.14 2-(6-bromo-3-hept-1-inyl-5-methyl-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 393.13 393.03 2-(3,7-bis-hydroxymethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 267.13 267.13 N-hydroxy-2-(7-hydroxymethyl-3-propyl-imidazo[1,2-a]pyridin-2 lamino)-acetamide 279.17 279.17 2-(3-tert-butyl-7-hydroxymethyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 293.19 293.18 2-(3-cyclohexyl-7-hydroxymethyl-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 319.21 319.20 3-butyl-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 a]pyridine-6-carboxylic acid amide 306.19 306.18 2-(hydroxycarbamoymethyl-amino)-3-hydroxymethyl midazo[1,2-a]pyridine-6-carboxylic acid amide 280.12 280.14 3-tert-butyl-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 ]pyridine-6-carboxylic acid amide 306.19 306.18 2-(hydroxycarbamoylmethyl-amino)-3-(3,3,3-trifluoro-propyl) imidazo[1,2-a]pyridine-6-carboxylic acid amide 346.13 346.15 3-cyclohexyl-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 a]pyridine-6-carboxylic acid amide 332.21 332.20 2-(6,8-dibromo-3-butyl-5,7-dimethyl-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 447.03 447.05 2-(6,8-dibromo-3-ethyl-5,7-dimethyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 419.00 419.02 2-(3-benzyl-6,8-dibromo-5,7-dimethyl-imidazo[1,2-arpyidin-2- 481.01 481.05 WO 2006/114261 PCT/EP2006/003765 24 yamino)-N-hydroxy-acetamide 2-(6,8-dibromo-5,7-dimethyl-3-pentyl-imidazo(1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 461.05 461.08 3-[6,8-dibromo-2-(hydroxycarbamoylmethyl-amino)-5,7 dimethyl-imidazo[1,2-a]pyridin-3-yI]-propionic acid 462.98 463.01 2-[6,8-dibromo-3-(2,2-dimethyl-propyl)-5,7-dimethyl imidazo[1,2-a]pyrdin-2-ylamino]-N-hydroxy-acetamide 461.05 461.10 2-[6,8-dibromo-5,7-dimethyl-3-(3,3,3-trifluoro-propyl) midazo[1,2-a]pyridin-2-ylamino]-N-hydroxy-acetamide 486.98 487.04 2-(8-bromo-6-chloro-3-ethyl-imidazo(1,2-a]pyridin-2-yamino)-N hydroxy-acetamide 347.01 347.10 2-[8-bromo-6-chloro-3-(2,2-dimethyl-propyl)-imidazo[1,2 p 389.07 389.07 2-(8-bromo-6-chloro-3-cyclohexyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 401.07 401.08 2-(8-amino-3-butyl-6-chloro-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 312.15 312.16 2-(8-amino-6-chloro-3-ethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 284.11 284.12 2-(8-amino-6-chloro-3-hydroxymethyl-imidazo(1,2-a]pyridin-2 yIamino)-N-hydroxy-acetamide 286.09 286.02 2-(8-amino-3-benzyl-6-chloro-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 346.13 346.15 2-(8-amino-6-chloro-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 326.17 326.18 3-[8-amino-6-chloro-2-(hydroxycarbamoylmethyl-amino) imidazo[1,2-a]pyridin-3-yl]-propionic acid 328.10 328.12 2-(8-amino-6-chloro-3-propyl-imidazo[1,2-ajpyridin-2-ylamino) N-hydroxy-acetamide 298.13 298.06 2-(8-amino-3-tert-butyl-6-hloro-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 312.15 312.16 2-[8-amino-6-chloro-3-(2,2-dimethyl-propyl)-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 326.17 326.18 2-[8-amino-6-chloro-3-(3,3,3-trifluoro-propyl)-imidazo[1,2 a pyridin-2-ylamino]-N-hydroxy-acetamide 352.10 352.05 WO 2006/114261 PCT/EP2006/003765 25 2-(8-amino-6-chloro-3-cyclohexyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 338.17 338.18 2-(8-amino-6-bromo-3-butyl-imidazo[1,2-alpyridin-2-ylamino)-N hydroxy-acetamide 356.10 356.12 2-(8-amino-6-bromo-3-ethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 328.06 328.08 2-(8-amino-6-bromo-3-hydroxymethyl-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 330.04 330.06 2-(8-amino-3-benzyl-6-bromo-imidazo[1,2-a)pyridin-2-ylamino) N-hydroxy-acetamide 390.08 390.11 2-(8-amino-6-bromo-3-pentyl-imidazo(1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 370.12 370.13 2-(8-amino-6-bromo-3-propyl-imidazo[1,2-a]pyridin-2-ylamino) N-hydroxy-acetamide 342.08 342.10 2-(8-amino-6-bromo-3-tert-butyl-imidazo[1,2-a]pyridin-2 lamino)-N-hydroxy-acetamide 356.10 356.11 2-[8-amino-6-bromo-3-(2,2-dimethyl-propyl)-imidazo(1,2 ]pyridin-2-ylamino]-N-hydroxy-acetamide 370.12 370.13 2-[8-amino-6-bromo-3-(3,3,3-trifluoro-propyl)-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 396.04 396.05 2-[8-amino-6-bromo-3-(2,2,2-trifluoro-ethyl)-imidazo[1,2 a]pyridin-2-ylamino]-N-hydroxy-acetamide 382.03 382.06 2-(8-amino-6-bromo-3-cyclohexyl-imidazo[1,2-a]pyridin-2 ylamino)-N-hydroxy-acetamide 382.12 382.13 2-(6-amino-3-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy cetamide 278.19 278.19 2-(6-amino-3-ethyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 250.15 250.15 2-(6-amino-3-benzyl-imidazo[1,2-a]pydin-2-ylamino)-N- 312.17 312.25 hydroxy-acetamide31.7 125 2-(6-amino-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 292.21 292.20 hydroxy-acetamide29.1 9.0 3-[6-amino-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 a]pyridin-3-yl)-propionic acid 294.14 294.15 2-(6-amino-3- ropy-imidaz,2-alpyridin-2-ylaino)-N- 264.17 264.27 WO 2006/114261 PCT/EP2006/003765 26 hydroxy-aceta mide 2-(6-amino-3-tert-butyI-imidazo[l,2-a]pyridin-2-ylimino)-N- 278.19 278.18 hydroxy-acetamide 278.__ 28.1 2-[6-amino-3-(2,2-dimethyl-propyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 292.21 292.20 2-[6-amino-3-(3,3,3-trifluoro-propyl)-imidazo[1,2-a]pyridin-2 381 381 lamino]-N-hydroxy-acetamide 318.15 2-[6-amino-3-(2,2,2-trifluoro-ethyl)-imidazo[1,2-a]pyridin-2-30.2 041 ylamino-N-hydroxy-acetamide304.12 304.11 2-(6-amino-3-cyclohexyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 304.21 304.20 ydroxy-acetamide 2-(8-amino-3-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 278.19 278.19 2-(8-amino-3-benzyl-imidazo[1,2-ajpyridin-2-ylamino)-N- 312.17 312.18 hydroxy-acetamide 31.1_121 2-(8-amino-3-pentyl-imidazo[l,2-a]pyridin-2-ylamino)-N- 292.21 292.20 hydroxy-acetamide 292.1_ 22.2 2-(8-amino-3-propyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 264.17 264.20 hydroxy-acetamide 2-(8-amino-3-tert-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 278.19 278.19 ydroxy-acetamide 2[8-amino-3-(2,2-dimethyl-propyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 292.21 292.20 2-[8-amino-3-(3,3,3-trifluoro-propyl)-imidazo[1,2-a]pyridin-2 lamino]-N-hydroxy-acetamide 318.14 318.15 2-(5-amino-3-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 278.19 278.25 2-(5-amino-3-benzyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 312.17 312.19 hydroxy-acetamide 2-(5-amino-3-pentyl-imidazo[1,2-a]pyridin-2-yIamino)-N- 292.21 292.20 hydroxy-acetamide29.1 9.0 2-(5-amino-3-propyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 264.17 264.17 hydroxy-acetamide26.7 641 2-(5-amino-3-tert-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N- 278.19 278.19 hydroxy-acetamide 278.9_ 28.1 WO 2006/114261 PCT/EP2006/003765 27 2-[5-amino-3-(3,3,3-trifluoro-propyl)-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 318.14 318.16 2-[5-amino-3-(2,2,2-trifluoro-ethyl)-imidazo[1,2-a]pyridin-2 lamino]-N-hydroxy-acetamide 304.12 304.10 2-(5-amino-3-cyclohexyl-imidazo[1,2-ajpyridin-2-ylamino)-N hydroxy-acetamide 304.21 304.21 2-(3-butyl-8-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy cetamide 277.20 277.22 N-hydroxy-2-(3-hydroxymethyl-8-methyl-imidazo[1,2-a]pyridin 2-ylamino)-acetamide 251.14 251.13 2-(3-benzyl-8-methyl-imidazo[1 2-a]pyridin-2-ylamino)-N hydroxy-acetamide 311.18 311.11 N-hydroxy-2-(8-methyl-3-pentyl-imidazo[1,2-a]pyridin-2 lamino)-acetamide 291.22 291.21 2-[3-(2,2-dimethyl-propyl)-8-methyl-imidazo[1,2-a]pyridin-2 ylamino]-N-hydroxy-acetamide 291.22 291.21 N-hydroxy-2-[8-methyl-3-(3,3,3-trifluoro-propyl)-imidazo(1,2 a]pyridin-2-ylamino]-acetamide 317.14 317.15 2-(3-cyclohexyl-8-methyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 303.22 303.21 2-(3-butyl-7-ethyl-imidazo[1,2-a]pyridin-2-yamino)-N-hydroxy acetamide 291.22 291.21 2-(7-ethyl-3-hydroxymethyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 265.16 265.07 2-(3-benzyl-7-ethyl-imidazo[1,2-a]pyridin-2-ylamino)-N-hydroxy acetamide 325.20 325.20 2-(7-ethyl-3-pentyl-imidazo[1,2-a~pyridin-2-ylamino)-N-hydroxy acetamide 305.24 305.23 2-(3-cyclohexyl-7-ethyl-imidazo[1,2-alpyrdin-2-ylamino)-N hydroxy-acetamide 317.24 317.23 2-(3-butyl-8-hydroxy-imidazo[1,2-alpyridin-2-ylamino)-N hydroxy-acetamide 279.17 279.20 2-(3-ethyl-8-hydroxy-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 251.14 251.14 Nh ,2-a]pyridin- 253.11 253.12 WO 2006/114261 PCT/EP2006/003765 28 2-ylamino)-acetamide 2-(3-benzyl-8-hydroxy-imidazo[1,2-alpyridin-2-ylamino)-N hydroxy-acetamide 313.15 313.17 N-hydroxy-2-(8-hydroxy-3-pentyl-imidazo[1,2-a]pyridin-2 lamino)-acetamide 293.19 293.19 N-hydroxy-2-(8-hydroxy-3-propyl-imidazo[1,2-ajpy 2-aiinylamino)-acetamide 265.16 265.16 2-(3-tert-butyl-8-hydroxy-imidazo[1,2-alpyridin-2-ylamino)-N hydroxy-acetamide 279.17 279.17 2-[3-(2,2-dimethyl-propyl)-8-hydroxy-imidazo[1,2-alpyridin-2 lamino]-N-hydroxy-acetamide 293.19 293.19 N-hydroxy-2-[8-hydroxy-3-(3,3,3-trifluoro-propyl)-imidazo[1,2 a]pyridin-2-ylamino]-acetamide 319.12 319.13 2-(3-cyclohexyl-8-hydroxy-imidazo[1,2-ajpyridin-2-ylamino)-N hydroxy-acetamide 305.19 305.19 2-(3-butyl-imidazo[2, 1-a]isoquinolin-2-yarnino)-N-hydroxy- 313.20 313.20 acetamide 2-(3-benzyI-imidazo(2,1-aisoquinolin-2-ylamino)-N-hydroxy- 347.18 347.19 cetamide34.8 471 N-hydroxy-2-(3-pentyl-imidazo[ 2 ,1-a]isoquinolin-2-ylamino)- 327.22 327.22 acetamide 2-[3-(2,2-dimethyl-propyl)-imidazo[ 2 ,1-a]isoquinolin-2-ylamino] N-hydroxy-acetamide 327.22 327.22 2-(3-cyclohexyl-imidazo[2,1-a]isoquinolin-2-yiamino)-N-hydroxy acetamide 339.22 339.21 2-(8-benzyloxy-3-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 369.23 369.23 2-(8-benzyloxy-3-hydroxymethyl-imidazo[l,2-a]pyridin-2 amino)-N-hydroxy-acetamide 343.17 343.18 2-(8-benzyloxy-3-pentyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 383.25 383.23 2-(8-benzyloxy-3-propyl-imidazo[1,2-ajpyridin-2-ylamino)-N- 355.21 355.22 hydroxy-acetamide 355.21 355_22 2-(8-benzyloxy-3-tert-butyl-imidazo[1,2-a]pyridin-2-ylamino)-N hydroxy-acetamide 369.23 369.25 WO 2006/114261 PCT/EP2006/003765 29 2-[8-benzyloxy-3-(2,2-dimethyl-prop)-midazo[1,2-a]pyridin-2- 383.25 383.25 glamino-N-hydry-acetamide _3:_25 8 2-(8-benzyloxy-3-cycohexyl-imidazo[1,2-alpyridirn2-ylamino)-N- 395.25 395.25 ydroxy-acetamide 395.5_ 35.2 2-(hydroxycarbamoylmethy-amino)-3-pentyl-imidazo[1,2 a]pyridin-8-carboxylic acid 321.19 321.14 3-butyl-2-(hydroxycarbamoylmethiamino)imidazo[l,2 ]pyridin-8-caroxylic acid 307.17 307.20 2-(hydroxycarbamoylmethylamino)-3-pentyl-imidazo[1,2-32.9 217 a]pyridin-8-arboxylic acid 321.19 321.17 3-( 2

,

2 -dimethyl-propy-2-(hydroxycarbamoylmethyl-amino)- 321.19 321.19 imidazoll,2-a]pyrdin-8-carboxylic acid 3cyclohexyl-2-(hydroxycarbamoylmethyl-amino)-imidazo[1,2 ]pyridin-8-carboxylic acid 333.19 333.20 Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims

1. Compounds of formula (1) R, R N H SN RN Re R R R < R wherein the radicals R 1 , R 2 , R 3 and R 4 , independently of one another, are a hydrogen atom, a halogen atom, a hydroxy, amino, nitro or thiole group, an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, hetero alkylcycloalkyl, heterocycloalkyl, aralkyl or a heteroaralkyl radical, whereby each of these radicals, independently of one another, may be substituted, or two of the radicals R 1 , R 2 , R 3 and R 4 together may be part of a cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring, whereby each of these rings may optionally be substituted; R 5 is a hydrogen atom, an alkyl, alkenyl, heteroalkyl, or cycloalkyl, whereby each of these radicals may optionally be substituted; the radicals R* and R , independently of one another, are a hydrogen atom, or an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroaralkyl radical, whereby each of these radicals, independently of one another, may optionally be substituted; and X is a group of formula -CO-NHOH, or a pharmaceutically acceptable salt, solvate, hydrate or a pharmaceutically acceptable formulation thereof.

2. Compounds according to claim 1, whereby R 1 is a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group or an ethyl group. -31

3. Compounds according to claim 1, whereby R 2 is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or an ethyl group.

4. Compounds according to claim 1, whereby R 3 and R 4 are not hydrogen atoms at the same time.

5. Compounds according to claim 1, whereby R 3 is a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group, an ethyl group or a propyl group.

6. Compounds according to claim 1, whereby R 4 is a chlorine atom, a bromine atom, a methyl group, an ethyl group or a propyl group.

7. Compounds according to claim 1, in which R 3 is a bromine atom and R 4 is a methyl group, or in which R 3 is a hydrogen atom and R 4 is a chlorine atom or a bromine atom.

8. Compounds according to claim 1, in which R 5 is a tert-butyl group, an isopropyl group, a neopentyl group or a n-hexyl group.

9. Compounds according to claim 1, in which the groups R* and R , independently of one another, are hydrogen atoms, hydroxymethyl groups or methyl groups.

10. Pharmaceutical composition which contains a compound according to any one of claims 1 to 9 and optionally carriers and/or adjuvants.

11. Use of a compound according to any one of claims 1 to 9 or a pharmaceutical composition according to claim 10 for the inhibition of metalloproteinases.

12. Use of a compound according to any one of claims 1 to 9 or a pharmaceutical composition according to claim 10 for the inhibition of peptide deformylase (PDF).

13. Use of a compound according to any one of claims 1 to 9 or a pharmaceutical composition according to claim 10 in the prevention and/or treatment of diseases conveyed by metalloproteinase activity. -32

14. Use of a compound according to any one of claims 1 to 9 or a pharmaceutical composition according to claim 10 in the prevention and/or treatment of diseases conveyed by peptide deformylase (PDF) activity.

15. Use of a compound according to any one of claims 1 to 9 or a pharmaceutical composition according to claim 10 as an antibiotic.

16. Use of a compound according to any one of claims 1 to 9 in the manufacture of a medicament for the treatment and/or prevention of diseases conveyed by metalloproteinase activity.

17. A method of treating and/or preventing diseases conveyed by metalloproteinase activity, comprising administering to a subject in need thereof a compound according to any one of claims 1 to 9.

18. Use of a compound according to any one of claims 1 to 9 in the manufacture of a medicament for the treatment and/or prevention of bacterial infections.

19. A method of treating and/or preventing bacterial infections, comprising administering to a subject in need thereof a compound according to any one of claims 1 to 9.

20. Compounds according to claim 1, substantially as hereinbefore described with reference to any one of the examples.