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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/64—One oxygen atom attached in position 2 or 6
  • C07D213/643—2-Phenoxypyridines; Derivatives thereof
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  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
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  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
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  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
  • A61P33/06—Antimalarials
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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  • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
  • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
  • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
  • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
  • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
  • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
  • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
  • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
  • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
  • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
  • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
  • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
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  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
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  • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
  • C07C309/63—Esters of sulfonic acids
  • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
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  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
  • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
  • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
  • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
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  • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
  • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
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  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
  • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
  • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
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  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
  • C07D209/50—Iso-indoles; Hydrogenated iso-indoles with oxygen and nitrogen atoms in positions 1 and 3
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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/62—Oxygen or sulfur atoms
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  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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  • C07D213/72—Nitrogen atoms
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  • C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
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Definitions

• the invention relates to hydroxyphenyl derivatives and a process for making the same. It also relates to the biological applications thereof, particularly as anti-bacterial and/or anti-parasites agents.
• Triclosan (TCL) 5-chloro-2- (2, 4-dichloro-phenoxy) - phenol (A) is a broad-spectrum biocide that has been in use for over 30 years, mainly as a component of antimicrobial wash products in health-care settings, of formula (A)
• Triclosan has found extensive use in consumer products such as toothpaste, mouthwashes, deodorants, hand soaps, and lotions. It is also incorporated in children's toys, cutting boards, and the plastic film used to wrap meat products. Until recently, it was thought that Triclosan, being a small hydrophobic molecule, was absorbed via diffusion into the bacterial cell wall and that unspecific disruption of the cell wall was the mechanism by which Triclosan exhibited its antibacterial activity. However, the first evidence that Triclosan inhibits fatty acid biosynthesis came when a strain of E.coli resistant to Triclosan was isolated, and the resistance was mapped to the fabl gene which codes for the E.coli trans enoyl-acyl carrier protein reductase (ENR).
• ETR E.coli trans enoyl-acyl carrier protein reductase
• Fatty acid biosynthesis in bacteria is essential to the production of a number of lipid-containing components including the cell membrane.
• the bacterial fatty acid synthase system utilizes discrete monofunctional enzymes that operate in conjunction with acyl carrier protein (ACP) -associated substrates.
• ACP acyl carrier protein
• Mammalian fatty acid synthase (FASI) differs from FASII in that lipid biosynthesis is mediated by a single multifunctional enzyme-ACP complex.
• the differences in prokaryote and eukaryote fatty acid biosynthesis offer an attractive opportunity for selective FASII inhibition.
• Fabl is an enoyl-ACP reductase that catalyzes the ultimate and rate- limiting step of the chain elongation process of FASII.
• the reaction involves the conjugate reduction of an enoyl-ACP to the corresponding acyl- ACP using the cofactor NAD(P)H as a hydride source.
• Triclosan As a specific E.coli Fabl inhibitor.
• Two ENR isoforms, FabK and FabL have been discovered in the gram-positive bacteria, Streptococcus pneumoniae and Bacillus subtilis, respectively.
• FabK is resistant to Triclosan, whereas FabL is reversibly inhibited by Triclosan.
• Triclosan also directly inhibits the Fabl from Staphylococcus aureus, Haemophilus influenzae, the ENR from Mycobacterium tuberculosis, InhA, and the ENR from Plasmodium falciparum, the malarial parasite.
• Triclosan itself has been described in separate chemo-enzymatic studies of the Triclosan mode of action against Fabl. Especially, the antibacterial activity of several 2-hydroxydiphenyl ethers hexachlorophene and 2- hydroxydiphenylmethanes as well as 5-alkylated, -fluorinated or -formylated derivatives have been determined. On the other hand, before the discovery of the potent inhibition of Fabl by TCL, some modifications of the dichlorophenol part of TCL were also reported. For instance broad spectrum, but non specific antibacterial and antifungal derivatives were reported by introducing a pyridine instead of a phenyl ring.
• TCL which displays a broad spectrum biocidal effect with no distinction between microorganisms
• new TCL derivatives that would target only the microorganisms which carry the Fabl enzyme such as S. aureus or E.coli would be selective antibacterial or antiparasitic agents of interest with no antibacterial effect or selective pressure against other bacterial species.
• the inventors have found that specific substitutions of hydroxyphenyl derivatives having triclosan basic structure lead to derivatives that surprisingly display a selective and narrow spectrum of activity against relevant pathogens, particularly bacteria or parasites.
• An object of the invention is then to provide new substituted hydroxyphenyl derivatives which selectively inhibit the growth of bacteria carrying Fab enzymes such as Fabl, FabL, FabK, InhA.
• Another object of the invention is to provide a process for the synthesis of said derivatives.
• Still another object is to take advantage of the biological properties of said molecules to provide means, i.e. pharmaceutical compositions and methods, particularly useful for treating microbial infections.
• R 3 ,R b and R c identical or different, being H or as above defined with respect to R,
• - Y represents C(O)R, CO(O)R, C(S)R, C(S)OR, C(O)NR 3 , R b , phosphate, P(O) (OR) 2 , CH 2 OR, or any labile group which may act as a prodrug to regenerate the free phenol,
• Tl and T5 are independently N or C-R, R being H, methyl, ethyl, halo, then
• T2 or T4 are different from CH or N, • or
• T3 is different from N or C-R, wherein R represent H, methyl, ethyl, halo, nitro, hydroxy, amino, amido or a methyl or an ethyl group substituted with halo, nitro, hydroxy, amino, amido; if T2 and T4 are independently CH or N, then
• Tl or T5 are different from N or C-R, R being H, Me, ethyl, halo,
• T3 is different from N or C-R, wherein R represent H, methyl, ethyl, halo, nitro, hydroxy, amino, amido or a methyl or an ethyl group substituted with halo, nitro, hydroxy, amino, amido; if T3 represent N or C-R, wherein R represent H, methyl, ethyl, halo, nitro, hydroxy, amino, amido or a methyl or an ethyl group substituted with halo, nitro, hydroxy, amino, amido; then.
• Tl or T5 are different from N or C-R, R being H, Me, ethyl, halo, • or
• T2 or T4 are different from CH or N.
• Rl is an heterocycle and more specifically a pyridine
• the invention also includes the N-oxide form.
• Alkyl as applied herein means an optionally substituted alkyl group and preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and t-butyl, pentyl, n-pentyl, isopentyl, neopentyl, hexyl and octyl.
• Alkoxy and thioalkyl mean any 0 or S atom substituted by a substituted or not alkyl group.
• Aryloxy, “thioaryl”, “NH-aryl” mean any 0, S, N substituted by a substituted or not aryl, or heterocyclic group.
• Aryl (or “Ar”) means phenyl or naphtyl optionally substituted by R.
• Halogen or halo means F, Cl, Br, and I.
• Aliphatic heterocycle indicates an optionally substituted five or six membered monocyclic ring, or a nine or ten-membered bicyclic ring containing one to three heteroatoms chosen from the group of nitrogen, oxygen and sulfur, which are stable and available by conventional chemical synthesis.
• Illustrative heterocycles are for example selected in the group comprising benzofuryl, benzimidazolyl, benzopyranyl, benzothienyl, furyl, imidazolyl, indolinyl, morpholinyl, piperidinyl, piperazinyl, pyrrolyl, pyrrolidinyl, tetrahydropyridinyl, pyridinyl, thiazolyl, thienyl, quinolinyl, isoquinolinyl, and tetra- and perhydro-quinolinyl and isoquinolinyl, pyrazinyl, pyrazidinyl, triazinyl, purine, indolyl, indazolyl, pyrimidinyl, pyridonyl, oxazolyl, tetrahydropyranyl, tetrahydrofuranyl .
• the invention more particularly relates to hydroxyphenyl derivatives
• Rl is phenyl or a 6 membered monocyclic nitrogenous heteroaryl of formula
• R2 is phenyl, Ci-C 8 alkyl, C 2 -C 8 alkenyl , C 2 -C 8 alkynyl, Ci- C 4 fluoro-alkyl, C 2 -C 4 fluoro-alkenyl , 0R a , SR 3 , all being possibly substituted by 1 to 3 identical or different R 1 ,
• R a ,R b and R c are selected from the group consisting of H, Ci-C 8 alkyl , C 2 -C 8 alkenyl , C 2 - C 8 alkynyl , phenyl, heteroaryl and aliphatic heterocycle as defined above for R2, the heteroaryl and the heterocycle being possibly formed with the carbon and nitrogen atoms to which R a , R b and R c are linked,
• R' is selected from the group comprising heteroaryl and aliphatic heterocycle as defined above for R2, Ci-C 8 alkyl, CH 2 CO 2 R", CO 2 R", COR", CONR"R"' , OCOR", OR", NR"R"' , NR"COR”' , NR"C00R"' , 0C0NR"R”', NR"C0NR”R'” , NR"SO 2 R"' , SO 2 R", NR"SO 2 R"' , halogen and CN, R" and R"' , identical or different, are H, C 1 -C 8 alkyl or form together a 4 to 6 membered heterocycle with 1 to 3 heteroatoms selected from N, 0 and S,
• - Y represents H or a labile chemical group able to regenerate in vivo the free phenol selected from the group consisting of C(O)R 3 , C(O)OR 3 , C(O) NR 3 , R b , P(O) (OH) 2 , and C0CHR a NR b R c , - Zl and Z3, identical or different, are halogen or H,
• - Z2 is fluor or H
• - or Z6 is a carbon atom substituted by R as defined above, R being different from H, alkyl, halogen, NH 2 , OH, CONH 2 or fluoro alkyl and all the other definitions are as defined above, - or Z4 or Z5 , or Z7 or Z8 are carbon atoms substituted by NR 3 R b or 0R a being different from H and all the other definitions are as defined above,
• Ci-C 8 alkyl as applied herein means linear, branched or cyclic hydrocarbon groups having 1 to 8 carbon atoms preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and t-butyl, pentyl, n-pentyl, isopentyl, neopentyl, hexyl, octyl, cyclopropyl cyclobutyl, , cyclopentyl, cyclohexyl;
• C 2 -C 8 alkenyl and “C 2 -C 8 alkynyl” as applied herein means linear, branched or cyclic hydrocarbon groups of 2 to 8 carbon atoms, having at least one double bond or one triple bond and preferably, ethenyl, propenyl, butenyl, cyclohexenyl, ethynyl, propargyl, butynyl;
• C ⁇ -C 4 fluoro alkyl and C 2 -C 4 alkenyl means a Ci-C 4 alkyl or C 2 -C 4 alkenyl group substituted by 1 to 7 fluorine atoms.
• Halogen means F, Cl, Br, and I
• Heteroaryl and “Aliphatic Heterocycle” as applied herein means a 5-10 membered aromatic or non-aromatic mono or bicyclic ring, containing at least one heteroatom selected from N, 0 and S.
• Illustrative heterocycles are for example selected in the group comprising benzofuryl, benzimidazolyl, benzopyranyl, benzothienyl, furyl, imidazolyl, indolinyl, azetidinyl, morpholinyl, piperidinyl, piperazinyl, oxazolidinyl, pyrrolyl, pyrrolidinyl, pyrazolyl, tetrahydropyridinyl, pyridinyl, thiazolyl, thienyl, quinolinyl, isoquinolinyl, and tetra- and perhydro-quinolinyl and isoquinolinyl, pyrazinyl, pyr
• C x -Cg alkyl-heteroaryl means a Ci-Cs alkyl such as above defined substituted with one heteroaryl group such as above defined.
• Ci-Cg alkyl-ORa means a Ci-C 8 alkyl such as above defined substituted with one OR a group such as above defined, 0R a being different from OH.
• the invention particularly relates to derivatives of formula (I) wherein Rl is a
• the nitrogeneous heteroaryl with one or 3 nitrogen atoms is selected in the group comprising a pyridine, a pyrimidine, a pyridazine, a pyrazine or a triazine.
• Rl is a substituted heteroaryl group such as above defined.
• the invention particularly relates to derivatives of formula (I) wherein Rl is a phenyl group.
• Z2 is fluor.
• Z6 is a carbon atom substituted by R as defined above, R being different from H, alkyl, halogen, NH 2 , OH, CONH 2 , or fluoro alkyl and all the other definitions are as defined with respect to formula (I) .
• Z4 or Z5, or Z7 or Z8, are carbon atoms substituted by NR a R b or 0R a , OR 3 being different from OH and all the other definitions are as defined with respect to formula (I) .
• Z5 or Z7 is a carbon atom substituted by R, R being different from H and all the other definitions are as defined with respect to formula (I).
• the invention particularly relates to derivatives of formula (I) wherein, R2 is a Ci-Cealkyl-heteroaryl or a Ci-C 8 alkyl-0R 3 , OR 3 being different from OH.
• Y represents H.
• compounds in which Y is different from H Y being a labile chemical group able to regenerate in vivo the free phenol compounds of formula I with Y being H such C(O)R a , C(O)OR 3 , C(O)NR 3 , C(O) NR 3 , R b , P(O) (OH) 2 , COCHR a NR b R c
• the invention also relates to a process for making the above defined derivatives.
• said process comprises the steps of
• R3 represents an alkyl group
• A is a reactive group such as an halogen or a nitro capable of reacting with the OH group of (II) under basic conditions known to the one skilled in the art to give a derivative of formula (III)
• Y H advantageously by methods known by one skilled of the art into a compound in which Y is C(O)R 3 , CO(O)R 3 , C(O) NR 3 , R b , P(O) (OH) 2 , and COCHR a NR b R c .
• the above disclosed phenol derivatives of the invention have valuable biological properties.
• the derivatives of the present invention show a high activity against bacteria carrying Fab enzymes such as Fabl, FabL, FabK, InhA.
• Fab enzymes such as Fabl, FabL, FabK, InhA.
• Staphyloccus aureus including multiresistant strains, Escherichia coli, Helicobacter pylori and also bacteria such as Mycobacterium tuberculosis carrying homologous Fab enzymes such as InhA or other organisms such as Plasmodium falciparum.
• Said derivatives are then particularly suitable as active principle of drugs.
• the invention thus also relates to compositions comprising a phenol derivative of formula (I) such as above defined for use as drug.
• compositions comprising a phenol derivative of formula (I) such as above defined in combination with a pharmaceutically acceptable carrier.
• Said pharmaceutical compositions are formulated to be administered under oral, injectable, parental routes, with doses appropriate for the patient to be treated.
• compositions of the invention may conveniently be presented in unit dosage form and may be prepared by any methods well known in the art of pharmacy.
• the amount of active ingredient which can be combined with a carrier material to produce a single dosage form will generally be that amount of the compound which produces a therapeutic effect.
• a suitable daily dose of the compounds of the invention will be that amount of the compound that is the lowest dose effective to produce a therapeutic effect.
• topical, intravenous and subcutaneous doses of the compositions of this invention for a patient, when used for the indicated effects will range from about 0.0001 to about 100 mg per kilogram of body weight per day, given in one or several doses administered separately at appropriate intervals throughout the day, optionally, in unit dosage forms.
• compositions are particularly useful to treat human or animal infections by microbial pathogens such as E. coli, H. pylori or S. aureus or M. tuberculosis and parasites such as Plasmodium falciparum.
• microbial pathogens such as E. coli, H. pylori or S. aureus or M. tuberculosis and parasites such as Plasmodium falciparum.
• compositions are also useful in multitherapy, in combination with other drugs, for example with antibiotics.
• the invention also relates to a method of treatment of microbial infections which comprises administering to a patient in need thereof an efficient amount of a pharmaceutical composition such as above defined.
• CDCI 3 is deuteriochloroform
• DMSO-d 6 is hexadeuteriodimethylsulfoxide
• CD 3 OD is tetradeuteriomethanol .
• Mass spectra were obtained using either electrospray (ESI) or atmospheric pressure photoionization (APPI) techniques.
• ESI electrospray
• APPI atmospheric pressure photoionization
• Analtech Silica Gel GF and E. Merck Silica Gel 60 F-254 thin layer plates were used for thin layer chromatography. Flash chromatography was carried out on Flashsmartpack cartridge, irregular silica 40-60 ⁇ m or spherical silica 20-40 ⁇ m
• TLC thin layer chromatography
• MS mass spectra
• HPLC high pressure liquid chromatography
• NMR nuclear magnetic resonance
• APT attached proton test
• HSQC heteronuclear single quantum correlation
• NOESY nuclear Overhauser enhancement spectroscopy.
• t-Bu refers to the tertiary butyl radical
• Boc refers to the t-butyloxycarbonyl radical
• Ph refers to the phenyl radical
• Cbz refers to the benzyloxycarbonyl radical
• Bn refers to the benzyl radical
• Me refers to methyl
• Et refers to ethyl
• Ac refers to acetyl
• Nph refers to 1- or 2-naphthyl
• cHex refers to cyclohexyl.
• DCC refers to dicyclohexylcarbodiimide
• DMAP refers to 4- dimethylaminopyridine
• EDC refers to 1- (3-dimethylaminopropyl) - 3-ethylcarbodiimide
• hydrochloride HOBt refers to 1- hydroxybenzotriazole
• THF refers to tetrahydrofuran
• DIEA refers to diisopropylethylamine
• DEAD refers to diethyl azodicarboxylate
• PPh 3 refers to triphenylphosphine
• DIAD refers to diisopropyl azodicarboxylate
• DME refers to dimethoxyethane
• DMF refers to dimethylformamide
• NBS refers to N- bromosuccinimide
• Pd/C refers to a palladium on carbon catalyst
• PPA refers to polyphosphoric acid
• DPPA diphenylphosphoryl azide
• reaction mixture was allowed to stir for 6 hr, with gradual warming to -20 0 C.
• reaction was hydrolysed with saturated NH 4 Cl (30 mL) , extracted with dichoromethane (2*10 mL) .
• Combined organic phases were washed with 100 mL of satured NaHCO 3 , dried over Na 2 SO 4 , concentrated in vacuo, the title compound (1.97 g; 41%) was obtained as a colourless oil, after purification on silica gel (dichloromethane/cyclohexane : gradient) .
• Aletrnatively compound of example 5 can be synthesized starting from the 2- (benzyloxy) -4-propylphenol instead of -methoxy-4- propylphenol using the same protocol as example 3 step f) and g ) .
• Example 25 2- [ (4 , 6-difluoropyridin-2-yl) oxy] -5-propylphenol (25A) and2- [ (2 , 6-difluoropyridin-4-yl) oxy] -5-propylphenol (25B)
• reaction mixture was stirred at rt for 3h, then washed with brine (2x) , dried over MgSO 4 , concentrated and purified by preparative TLC on silica gel (ethyl acetate/cyclohexane - 30/70) to yield the title compound (101 mg ; 0.21 mmol ; 41 %) .
• Example 38 2- ⁇ 3- [4- (4-Ethyl-2-hydroxy-phenoxy) -3-fluoro- phenoxy] -propyl ⁇ -isoindole-1 , 3-dione
• Example 40 [1- [4- (4-Eth ⁇ l-2-hydroxy-phenoxy) -3-fluoro-phenyl] - eth- (E) -ylideneaminooxy] -acetic acid ethyl ester
• Example 41 [ ( ⁇ (IE) -1- [4- (4-ethyl-2-hydroxyphenoxy) -3- fluorophenyl] ethylidene ⁇ amino) oxy] acetic acid
• Example 42 3-Morpholin-4-yl-propane-l-sulfonic acid [4- (4- ethyl-2-hydroxy-phenoxy ) -3-fluoro-phenyl] -amide
• Trifluoroethanesulfonyl chloride (0.46 iranol; 84 mg) , the title compound was prepared (177 mg; quantitative yield) as a brown oil used without further purification.
• Example 65 4- (4-ethyl-2-hydroxyphenoxy) -3-fluorobenzene sulfonamide
• Example 70 N- ⁇ 2- [4- (4-Ethyl-2-hydroxy-phenoxy) -3-fluoro- benzenesulfonylamino] -ethyl ⁇ -acetamide
• N-Acetylethylenediamine (1.1 mmol; 0.10 mL) was slowly added to a solution of 4- (4-ethyl-2-methoxyphenoxy) -3- fluorobenzenesulfonyl chloride (0.94 mmol ; 325 mg) and TEA (2.8 mmol ; 0.40 mL) in anhydrous THF (5 mL) , under argon at 0 0 C. The reaction was stirred overnight with progressive warming to room temperature. Concentrated, the mixture was purified by chromatography (dichloromethane/methanol/ami ⁇ ionia gradient) to yield the title compound as a yellow oil (142 mg; 0.35 mmol ; 37%) used as such in the following reaction.
• Example 75 4- (4-Ethyl-2-hydroxy-phenoxy) -3-fluoro-N- (2- pyridin-2-yl-ethyl) -benzenesulfonamide
• the aqueous layer was extracted with dichloromethane and the combined dichloromethane fraction was washed with water, dried over anhydrous Na 2 SC> 4 and concentrated.
• the crude residue obtained was combined with the crude obtained from an earlier 20mg batch and column purified over silica gel using 2% methanol in dichloromethane as eluant to get 90mg, 68.3% of title compound.
• Example 80 N-acetyl-N 1 - [4- (4-ethyl-2-hydroxyphenoxy) -3-fluoro phenyl]propan-1 , 3-diamine

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