EP2560977A1 - Nouveaux composés de ag(i) avec ligands chélatants et leur emploi dans des compositions pharmaceutiques - Google Patents

Nouveaux composés de ag(i) avec ligands chélatants et leur emploi dans des compositions pharmaceutiques

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Publication number
EP2560977A1
EP2560977A1 EP11772330A EP11772330A EP2560977A1 EP 2560977 A1 EP2560977 A1 EP 2560977A1 EP 11772330 A EP11772330 A EP 11772330A EP 11772330 A EP11772330 A EP 11772330A EP 2560977 A1 EP2560977 A1 EP 2560977A1
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EP
European Patent Office
Prior art keywords
present
formula
compound
independently
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP11772330A
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German (de)
English (en)
Other versions
EP2560977A4 (fr
Inventor
Vratislav Langer
Morsy Abu-Youssef
Gohar Yousry
Massoud Alshima A
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Ohrstrom Lars
Original Assignee
Ohrstrom Lars
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Application filed by Ohrstrom Lars filed Critical Ohrstrom Lars
Publication of EP2560977A1 publication Critical patent/EP2560977A1/fr
Publication of EP2560977A4 publication Critical patent/EP2560977A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/38—Silver; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the present invention relates to new Ag(I) complexes with (E)-picolinaldehyde oxime, 4,5-diazafluorenone and their derivatives and related chelating pyridine based ligands, and their use in antimicrobial compositions.
  • Silver is recognised as a therapeutic agent used in the prevention of infection, and dilute solutions of silver nitrate and silver sulphadiazine have been among the most common preventive treatment for burns.
  • the interest in silver is largely attributed to its bactericidal efficacy at low concentration and its relatively limited toxicity to human cells.
  • Recently progress has led to an interest in dressings containing silver, which arises from advances in impregnation techniques and polymer technologies coupled with the increase in prevalence of bacterial resistance to antibiotics.
  • silver-based dressings on the market that aim to improve healing primarily by controlling the wound bioburden.
  • Kitamura, K. and Kondo, Y. JP 2000016906 describe a number of Ag(I) carboxylate complexes of nicotinic acid and related anionic ligands and their antibacterial properties.
  • Navarro describes l,10-phenanthroline-5,6-dione Ag(I) complexes and their effects on Leishmania parasites (Navarro, 2006) and McCann (McCann 2004) reported on Ag(l,10- phenanthroline-5,6-dione) 2 C10 4 and its effects on fungal and mammalian cells.
  • Yilmaz (Yilmaz 2008) reported antimicrobial activity studies on 5,5-Diethylbarbiturate complexes of silver with 2,2'-bipyridine and 3-(2-pyridyl)propanol and Zhu, (Zhu 2001) on the cytotoxicities of silver(I) complexes of 2,2'-bipyridines and 1,10-phenanthroline.
  • Onuegbu (Onuegbu 2007, Onuegbu 2008, Onuegbu 2009,) has reported a number of X-ray crystal structures of l,10-phenanthroline-5,6-dione Ag(I) complexes and Biju (Biju 2008) has reported on the structure of a 4,5-diazafluorenone silver(I) complex
  • Chen Chen (Chen, C-H, 2002) described the crystal structures of certain nicontinamide and nicotinic acid Ag(I) complexes with sulfonates counter anions
  • Balakrishna (Balakrishna, 2004) described the crystal structure of two Ag(I) isonicotinamide complexes. No biological data of any of these compounds were presented.
  • the present strategy to overcome the problems with solubility and photoinstability of Ag(I) compound is to investigate complexes having ligands that bind strongly to Ag(I), preventing premature release of "naked” Ag(I) and loss of efficiency as state above.
  • As the preferred coordination geometry of Ag (I) is linear two-coordinated and as it is known that ammonia dissolves precipitated AgCl(s) by forming a linear Ag(NH 3 ) 2 + complex, one should look at strongly binding nitrogen ligands enabling a linear coordination.
  • Pyridine is the most well known such example, but of course the toxicity of this ligand makes it unsuitable.
  • the Ag(I) complexes according to the invention are preferably complexes with neutral ligands, which are structurally and chemically different than the Ag(I) complexes described e.g. in (JP 2000016906), and are to have important advantages in terms of solubility, biological activity, bioavailability, and pharmacokinetics.
  • the present invention provides new Ag(I) complexes with (E)-picolinaldehyde oxime, 4,5- diazafluorenone and their derivatives and related chelating pyridine based ligands.
  • the present invention further provides methods for the use of Ag(I) complexes with these derivatives and related chelating pyridine ligands in the treatment, prevention and prophylaxis of infections.
  • the present invention provides a pharmaceutical preparation comprising, as an active ingredient, a compound according to Formula (I) or a pharmaceutical acceptable salt thereof together with a pharmaceutical acceptable carrier for the use in the treatment, prophylaxis and prevention of infections,
  • Rc and R D if present is or CH 2 CN
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen,
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the present invention provides a pharmaceutical preparation comprising, as an active ingredient, a compound comprising an ionic specie according to Formula (la) or a pharmaceutical acceptable salt thereof together with a pharmaceutical acceptable carrier for the use in the treatment, prophylaxis and prevention of infections,
  • Rc if present is or CH 2 CN
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen,
  • the compound is selected from:
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2” , H 3 COO “ , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the compound is selected from
  • the present invention provides a pharmaceutical preparation comprising, as an active ingredient, a compound according to Formula (lb) or a pharmaceutical acceptable salt thereof together with a pharmaceutical acceptable carrier for the use in the treatment, prophylaxis and prevention of infections,
  • n 1 or 2
  • R c if present, independently are ,
  • R 2 and R3 independently are H, NO 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen.
  • the compound is selected from:
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the present further provides a method for treatment, prophylaxis, or prevention of infection comprising administering to a mammal, including a human, in need thereof, a pharmaceutical effective amount of a compound according to Formula (I) or a
  • Rc and R D if present is or CH 2 CN
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen,
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the present invention provides a method for treatment, prophylaxis, or prevention of infection comprising administering to a mammal, including a human, in need thereof, a pharmaceutical effective amount of a compound comprising an ionic specie according to Formula (la) or a pharmaceutical acceptable salt thereof, Formula (la)
  • Rc if present is or CH 2 CN
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen,
  • the compound is selected from:
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the compound is selected from
  • the present invention provides a method for treatment, prophylaxis, or prevention of infection comprising administering to a mammal, including human, in need thereof, a pharmaceutical effective amount of a compound according to Formula (lb) or a pharmaceutical acceptable salt thereof, Formula (lb)
  • n 1 or 2 wherein Rc, if present, independently are ,
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen.
  • the compound is selected from:
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the present invention further provides use of a compound according to Formula (I) in the manufacture of a medicament for the use in the treatment, prophylaxis and prevention of infections,
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen,
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the present invention provides use of a compound comprising an ionic specie according to Formula (la) in the manufacture of a medicament for the use in the treatment prophylaxis and prevention of infections,
  • Rc if present is or CH 2 CN
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen, [Ag(4,5-diazaflourenone)2]X,
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the compound is selected from
  • the present invention provides use of a compound according to Formula (lb) in the manufacture of a medicament for the use in the treatment, prophylaxis and prevention of infections,
  • n 1 or 2
  • R c if present, independently are ,
  • R 2 and R 3 independently are H, NO 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen.
  • the compound is selected from:
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2” , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the compound is
  • the present invention further provides novel compounds according to Formula (II),
  • Rc if present is or CH 2 CN
  • R 2 and R 3 independently are H, N0 2 , alkyl, alkenyl, alkylcarbonyl, each optionally substituted with halogen,
  • X can be selected from N0 3 " , HS0 4 “ , S0 4 2” , HC0 3 “ , C0 3 2 , H 3 COO , CI “ , Br “ , ⁇ , BF 4 “ , H 3 P0 4 “ , H 2 P0 4 2” , and P0 4 3” .
  • the compounds of the present invention show strong antimicrobial activity and are useful in the treatment, prophylaxis and prevention of infections.
  • the infections to be treated or prevented are exemplified by, but not limited to, infections caused by bacteria, fungi, yeasts, or viruses, such as candidiasis, acne, herpes, and papilloma viral diseases.
  • the compounds of the present invention can be used in connection with treatment and prevention of pathological conditions of epithelial and dermal tissues, both intact and after lesion characterised by potential or acute infections sustained by pathogens., such as pathological conditions of the skin, of the mucosa and of the oral cavity, and external and internal genitals and ocular epithelia both intact and lesioned.
  • pathological conditions of epithelial and dermal tissues both intact and after lesion characterised by potential or acute infections sustained by pathogens.
  • pathological conditions of the skin, of the mucosa and of the oral cavity, and external and internal genitals and ocular epithelia both intact and lesioned can be used as therapeutic agents with disinfectant activity for the prevention, prophylaxis and treatment of the following pathological conditions:
  • Vascular tropic lesions ischemic ulcers, vascular ulcers, diabetic ulcers, stasis
  • the compounds of the present invention can have useful applications in paraphysiological conditions and for preventive purposes in dermoprotective, lenitive and cosmetic parapharmaceutical preparations.
  • compositions According to the pathology and the degree of seriousness the compounds of the present invention can be used in Ag(I) concentrations of 2 ⁇ 10 "6 to 1 - 10 "1 mol/dm 3 in topical formulations and in combination with appropriate diluents and helping substances compatible with the planned usage.
  • the compounds of the present invention can be present encapsulated in nanospheres or microspheres, be in the form of liquids, semi-solids, solids, containing excipients or diluents of pharmaceutical or cosmetic grade (for example solutions and aqueous, non-aqueous, hydroalcoholic suspensions, drops, gels, emulsions, creams, ovules, powder sprays, sprays with or without propellants, foams), be these new or known materials.
  • pharmaceutical or cosmetic grade for example solutions and aqueous, non-aqueous, hydroalcoholic suspensions, drops, gels, emulsions, creams, ovules, powder sprays, sprays with or without propellants, foams
  • the compounds of the present invention can be supported, as they are or in any form mentioned above, upon inter biomaterials such as films, membranes, patches and dressings, also with slow release, or can be incorporated into biomaterials or into materials dissolving slowly or rapidly in aqueous environment.
  • alkyl as used herein, means a straight or branched chain hydrocarbon containing from 1 to 6 carbon atoms. Representative examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n- pentyl, isopentyl, neopentyl, n-hexyl.
  • alkylcarbonyl as used herein, means an alkyl group, as defined herein, appended to the parent molecular moiety through a carbonyl group, as defined herein.
  • alkylcarbonyl include, but are not limited to, acetyl, 1- oxopropyl, 2,2-dimethyl-l-oxopropyl, 1-oxobutyl, and 1-oxopentyl.
  • alkenyl as used herein, means a straight or branched chain hydrocarbon containing from 2 to 6 carbons and containing at least one carbon-carbon double bond formed by the removal of two hydrogens.
  • Representative examples of alkenyl include, but are not limited to, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5- hexenyl.
  • halogen as used herein, means -CI, -Br, -I or -F.
  • the present compounds can exist as pharmaceutical acceptable salts.
  • “pharmaceutical acceptable salt” refers to salts or zwitterions of the compounds which are water or oil-soluble or dispersible, suitable for treatment of disorders without undue toxicity, irritation, and allergic response, commensurate with a reasonable benefit/risk ratio, and effective for their intended use.
  • the salts can be prepared during the final isolation and purification of the compounds or separately by reacting an amino group of the compounds with a suitable acid.
  • Representative salts include acetate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, glycerophosphate, hemisulfate, heptanoate, hexanoate, formate, isethionate, fumarate, lactate, maleate, methanesulfonate, naphthylenesulfonate, nicotinate, oxalate, pamoate, pectinate, persulfate, 3-phenylpropionate, picrate, oxalate, maleate, pivalate, propionate, succinate, tartrate, trichloroacetic, trifluoroacetic, glutamate, para- toluenesulfonate, undecanoate, hydrochloric, hydrobromic, sulfuric, phosphoric, and the like.
  • the compounds (1) [Ag(4,5-diazaflourenone)2]N03 and (2) [Ag((E)-picolinaldehyde oxime)](N0 3 )., were prepared from an aqueous silver nitrate solution and the
  • Crystal 2 357 vs, 370 m, 391 m, 405 w, 412 w, 430 w, 517 m, 550 w, 620 m, 668 m, 684 m,716 s, 758 vs, 824 m, 833 m, 915 s, 1029 m, 1081 m, 1099 s, 1 149 m, 1260 s, 1271 s, 1384 vs, 1402 vs sh, 1462 s, 1559 vs, 1588 s, 1596 s, 1717 vs, 1831h w,2342 s, 2360 s, 2426 m, 2983 s, 3033 s, 3062 m.
  • Example 2 Antimicrobial activity
  • MICs Minimum inhibitory concentrations
  • the test materials were dissolved in DMSO. The highest concentration used was 256 ⁇ g/ml.
  • the inoculum was 10 5 CFU/ml for bacteria and 10 4 CFU/ml for the yeast.
  • Bacteria were cultured in Mueller Hinton Broth (MHB) for 24 h at 35 °C and the yeast in Glucose Peptone Broth (GPB) for 48 h at 30°C.
  • MIC value was corresponding to the lowest concentration that inhibited the bacterial growth. S pyogenes.
  • MICs values were determine Kd. and the antimicrobial activity is inversely proportional to this value.
  • Concentrations us i e pneumonaed in this screening were: 1, 2, 4, 8, 16, 32, 64, 128 and 256 ( ⁇ / ⁇ ). 1 ⁇ g/ml corresponds to a 10 "4 % solution and an b l P iii mras.
  • compound (1) was also found to have antifungal activity, measured as the ability to inhibit growth of Candida albicans.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne de nouveaux complexes de Ag(I) avec la (E)-picolinaldéhyde oxime, la 4,5-diazafluorénone et leurs dérivés ainsi que les ligands chélatants à base de pyridine apparentés, et leur emploi dans des compositions antimicrobiennes.
EP11772330.4A 2010-04-22 2011-04-21 Nouveaux composés de ag(i) avec ligands chélatants et leur emploi dans des compositions pharmaceutiques Withdrawn EP2560977A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE1000411 2010-04-22
PCT/SE2011/050492 WO2011133104A1 (fr) 2010-04-22 2011-04-21 Nouveaux composés de ag(i) avec ligands chélatants et leur emploi dans des compositions pharmaceutiques

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EP2560977A1 true EP2560977A1 (fr) 2013-02-27
EP2560977A4 EP2560977A4 (fr) 2013-11-27

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Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005023760A2 (fr) * 2003-09-05 2005-03-17 The University Of Akron Complexes metalliques de carbenes n-heterocycliques utiles comme produits radiopharmaceutiques et antibiotiques
EP2167087A1 (fr) * 2007-05-31 2010-03-31 CSE Incubation AB Nouveaux composés d'ag(i) et utilisation de ceux-ci dans des compositions pharmaceutiques destinées au traitement et à la prévention d'infections

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
A OYA ET AL: "Preparation of an antibacterial ceramic filter from montmorillonite supporting silver chelate of 2,2'-dipyridyl", APPLIED CLAY SCIENCE, vol. 8, no. 5, 1 January 1994 (1994-01-01) , pages 365-371, XP055082703, ISSN: 0169-1317, DOI: 10.1016/0169-1317(94)90025-6 *
ANNA BELLUSCI ET AL: "Anion dependent mesomorphism in coordination networks based on 2,2'-bipyridine silver(i) complexes", DALTON TRANSACTIONS, no. 36, 1 January 2009 (2009-01-01), page 7381, XP055082691, ISSN: 1477-9226, DOI: 10.1039/b906178a *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ESHWIKA, AHMED ET AL: "Metal complexes of 1,10-phenanthroline-5,6-dione alter the susceptibility of the yeast Candida albicans to amphotericin B and miconazole", XP002714384, retrieved from STN Database accession no. 2004:438748 & ESHWIKA, AHMED ET AL: "Metal complexes of 1,10-phenanthroline-5,6-dione alter the susceptibility of the yeast Candida albicans to amphotericin B and miconazole", BIOMETALS , 17(4), 415-422 CODEN: BOMEEH; ISSN: 0966-0844, 2004, *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ONUEGBU, JONATHAN ET AL: "Acetato(1,10-phenanthroline-5,6-dione)sil ver(I) trihydrate", XP002714383, retrieved from STN Database accession no. 2008:148784 & ONUEGBU, JONATHAN ET AL: "Acetato(1,10-phenanthroline-5,6-dione)sil ver(I) trihydrate", ACTA CRYSTALLOGRAPHICA, SECTION E: STRUCTURE REPORTS ONLINE , 64(2), M403-M404, M403/1-M403/9 CODEN: ACSEBH; ISSN: 1600-5368 URL: HTTP://JOURNALS.IUCR.ORG/E/ISSUES/2008/02/ 00/CI2544/CI2544.PDF, 2008, *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; WANG, YOUXIANG ET AL: "Syntheses and Electrochemical, Photophysical, and Photochemical Properties of Ruthenium(II) 4,5-Diazafluorenone Complexes and Their Ketal Derivatives", XP002714382, retrieved from STN Database accession no. 1998:229743 & YOUXIANG WANG ET AL: "Syntheses and Electrochemical, Photophysical, and Photochemical Properties of Ruthenium(II) 4,5-Diazafluorenone Complexes and Their Ketal Derivatives", INORGANIC CHEMISTRY, vol. 37, no. 8, 1 April 1998 (1998-04-01), pages 2051-2059, XP055082682, ISSN: 0020-1669, DOI: 10.1021/ic970987e *
F YILMAZ: "5,5-Diethylbarbiturate Complexes of Silver with 2,2'-Bipyridine and 3-(2-Pyridyl)propanol: Syntheses, Crystal Structures, Spectroscopic, Thermal and Antimicrobial Activity Studies", ZEITSCHRIFT FUER NATURFORSCHUNG, TEIL B: CHEMICAL SCIENCES, vol. 63b, 1 January 2008 (2008-01-01), pages 134-138, XP055082684, *
FUMIHIKO OHASHI ET AL: "Antimicrobial and antifungal agents derived from clay minerals (II): properties of montmorillonite supported by silver chelates of 1,10-phenanthroline and 2,2'-dipyridyl", APPLIED CLAY SCIENCE, vol. 6, no. 4, 1 January 1992 (1992-01-01) , pages 301-310, XP055082704, ISSN: 0169-1317, DOI: 10.1016/S0169-1317(09)90005-9 *
MORSY A. M. ABU-YOUSSEF ET AL: "Synthesis, Crystal Structure, Quantum Chemical Calculations, DNA Interactions, and Antimicrobial Activity of [Ag(2-amino-3-methylpyridine) 2 ]NO 3 and [Ag(pyridine-2-carboxaldoxime)NO 3 ]", INORGANIC CHEMISTRY, vol. 49, no. 21, 1 November 2010 (2010-11-01), pages 9788-9797, XP055082683, ISSN: 0020-1669, DOI: 10.1021/ic100581k *
RODNEY P. FEAZELL ET AL: "Variability in the Structures of Luminescent [2-(Aminomethyl)pyridine]silver(I) Complexes: Effect of Ligand Ratio, Anion, Hydrogen Bonding, and [pi]-Stacking", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 2005, no. 16, 1 August 2005 (2005-08-01), pages 3287-3297, XP055082688, ISSN: 1434-1948, DOI: 10.1002/ejic.200500215 *
See also references of WO2011133104A1 *

Also Published As

Publication number Publication date
EP2560977A4 (fr) 2013-11-27
WO2011133104A1 (fr) 2011-10-27

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