[go: up one dir, main page]

WO2012164074A1 - Dérivés de mannose phosphate en tant qu'antagonistes de l'adhésion bactérienne - Google Patents

Dérivés de mannose phosphate en tant qu'antagonistes de l'adhésion bactérienne Download PDF

Info

Publication number
WO2012164074A1
WO2012164074A1 PCT/EP2012/060397 EP2012060397W WO2012164074A1 WO 2012164074 A1 WO2012164074 A1 WO 2012164074A1 EP 2012060397 W EP2012060397 W EP 2012060397W WO 2012164074 A1 WO2012164074 A1 WO 2012164074A1
Authority
WO
WIPO (PCT)
Prior art keywords
lower alkoxy
lower alkyl
optionally substituted
formula
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.)
Ceased
Application number
PCT/EP2012/060397
Other languages
English (en)
Inventor
Beat Ernst
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universitaet Basel
Original Assignee
Universitaet Basel
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Universitaet Basel filed Critical Universitaet Basel
Publication of WO2012164074A1 publication Critical patent/WO2012164074A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings

Definitions

  • Urinary tract infection is an inflammatory, pathogen-caused disease that occurs in any part of the urinary tract.
  • UTI is characterized by a wide spectrum of symptoms ranging from mild irritative voiding (dysuria), frequent voiding (polakisuria) or suprapubic tenderness to invasion of bacteria into the kidney (acute pyelonephritis) or blood circulation (urosepsis) with potential local and distant bacterial seeding (abscess), multiorgan failure or even death (B. Foxman, Dis. Mon. 2003, 49, 53-70).
  • the prefix “lower” denotes a radical having up to and including a maximum of 7, especially up to and including a maximum of 4 carbon atoms, the radicals in question being either linear or branched with single or multiple branching.
  • Any asymmetric carbon atoms may be present in the (R)-, (S)- or (R,S)-configuration, preferably in the (R)- or (S)-configuration.
  • the compounds may thus be present as mixtures of isomers or as pure isomers, preferably as enantiomer-pure diastereomers.
  • the invention relates also to possible tautomers of the compounds of formula (I).
  • Alkyl has from 1 to 12, preferably from 1 to 7 carbon atoms, and is linear or branched. Alkyl is preferably lower alkyl.
  • Aryl stands for a mono- or bicyclic fused ring aromatic group with 5 to 10 carbon atoms optionally carrying substituents, such as phenyl, 1-naphthyl or 2-naphthyl, or also a partially saturated bicyclic fused ring comprising a phenyl group, such as indanyl, dihydro- or tetrahydronaphthyl, all optionally substitued.
  • aryl is phenyl or indanyl or tetrahydronaphthyl, in particular phenyl.
  • substituents are preferably lower alkyl, lower alkoxy, halo, optionally substituted aryl or optionally substituted heteroaryl, and are connected with a saturated or unsaturated carbon atom of alkenyl or alkinyl.
  • Cyanoalkyl designates preferably cyanomethyl and cyanoethyl.
  • Haloalkyl is preferably fluoroalkyl, especially trifluoromethyl, 3,3,3-trifluoroethyl or pentafluoroethyl.
  • ArylalkyI includes aryl and alkyl as defined hereinbefore, and is e.g. benzyl, 1 -phenethyl or 2-phenethyl.
  • Particular salts considered are those replacing one or two hydrogen atoms of the phosphate group, and optionally of a further acidic function, e.g. of a carboxylic acid function.
  • Suitable cations are, e.g., sodium, potassium, calcium, magnesium or ammonium cations, or also cations derived by protonation from primary, secondary or tertiary amines containing, for example, lower alkyl, hydroxy-lower alkyl or hydroxy-lower alkoxy-lower alkyl groups, e.g., 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl- dimethylammonium, diethylammonium, di(2-hydroxyethyl)ammonium, trimethyl- ammonium, triethylammonium, 2-hydroxyethyldimethylammonium, or di(2-hydroxyethyl)- methylammonium, also from correspondingly substituted cyclic secondary and terti
  • Suitable inorganic acids are, for example, halogen acids, such as hydrochloric acid, sulfuric acid, or phosphoric acid.
  • the compounds of formula (I) have valuable pharmacological properties.
  • the invention also relates to compounds of formula (I) and salts as defined hereinbefore for use as medicaments.
  • a compound of formula (I) according to the invention shows prophylactic and therapeutic efficacy especially against bacterial infections, in particular against infective diseases caused by Escherichia coli (£. coli), a Gram negative bacterium commonly found in the lower intestine of warm-blooded organisms. Most E. coli strains are harmless and part of the normal flora of the gut, however, the compounds of the invention are useful in the treatment of infective diseases caused by virulent strains of £.
  • coli in particular in the treatment of gastroenteritis, diarrhea, food poisoning, urinary tract infections, pyelonephritis, and neonatal meningitis caused by £ coli strains, also in the treatment of unusual infective diseases caused by virulent £ coli strains, in particular in the treatment of haemolytic-uremic syndrome (HUS), peritonitis, mastitis, sepsis, and pneumonia caused by £ coli.
  • HUS haemolytic-uremic syndrome
  • the invention refers to compounds of formula (I), wherein R 1 is pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, benzimidazolyl, benzofuryl, pyridopyrrolyl, pyridoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, or purinyl, all optionally substituted.
  • R 1 is pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, is
  • Preferred substituents considered for R 1 with the meaning of the mentioned heteroaryl groups are alkyl, halo-lower alkyl, cycloalkyl-lower alkyl, lower alkoxy-lower alkyl, lower alkoxy-lower alkoxy-lower alkyl, optionally substituted alkenyl, optionally substituted alkinyl, cycloalkyl, aryl, heteroaryl, hydroxy, lower alkoxy, cycloalkyloxy, alkenyloxy, alkinyloxy, hydroxysulfonyloxy, lower alkylmercapto, hydroxysulfinyl, lower alkylsulfinyl, halo-lower alkylsulfinyl, hydroxysulfonyl, lower alkylsulfonyl, arylsulfonyl; amino optionally substituted by one or two substitutents selected from lower alkyl, cycloalkyl-lower alkyl,
  • R 9 is carboxy or lower alkoxycarbonyl
  • a carboxy group in a carboxy-substituted aryl or heteroaryl group may be amidated under conditions used for amide formation known per se in peptide chemistry, e.g. with the corresponding amine and an activating agent for the carboxy group, such as 1 -hydroxy- benzotriazole, optionally in the presence of suitable catalysts or co-reagents.
  • Salts can usually be converted to free compounds, e.g. by treating with suitable acids. It should be emphasized that reactions analogous to the conversions mentioned in this chapter may also take place at the level of appropriate intermediates.
  • All process steps described here can be carried out under known reaction conditions, preferably under those specifically mentioned, in the absence of or usually in the presence of solvents or diluents, preferably such as are inert to the reagents used and able to dissolve these, in the absence or presence of catalysts, condensing agents or neutralising agents, for example ion exchangers, typically cation exchangers, for example in the H + form, depending on the type of reaction and/or reactants at reduced, normal, or elevated temperature, for example in the range from -100°C to about 190°C, preferably from about -80°C to about 150°C, for example at -80 to +60°C, at -20 to +40°C, at room temperature, or at the boiling point of the solvent used, under atmospheric pressure or in a closed vessel, where appropriate under pressure, and/or in an inert atmosphere, for example under argon or nitrogen.
  • solvents or diluents preferably such as are inert to the reagents
  • isomeric mixtures that occur can be separated into their individual isomers, e.g. diastereomers or enantiomers, or into any mixtures of isomers, e.g.
  • New starting materials and/or intermediates, as well as processes for the preparation thereof, are likewise the subject of this invention.
  • such starting materials are used and reaction conditions so selected as to enable the preferred compounds to be obtained.
  • compositions for oral administration also include hard capsules consisting of gelatin, and also soft, sealed capsules consisting of gelatin and a plasticizer, such as glycerol or sorbitol.
  • the hard capsules may contain the active ingredient in the form of granules, for example in admixture with fillers, such as corn starch, binders, and/or glidants, such as talc or magnesium stearate, and optionally stabilizers.
  • the active ingredient is preferably dissolved or suspended in suitable liquid excipients, such as fatty oils, paraffin oil or liquid polyethylene glycols or fatty acid esters of ethylene or propylene glycol, to which stabilizers and detergents, for example of the polyoxy- ethylene sorbitan fatty acid ester type, may also be added.
  • suitable liquid excipients such as fatty oils, paraffin oil or liquid polyethylene glycols or fatty acid esters of ethylene or propylene glycol, to which stabilizers and detergents, for example of the polyoxy- ethylene sorbitan fatty acid ester type, may also be added.
  • Example 28 (Biphenyl-4-yl 2,3-O-dibenzoyl-a-D-mannopyranoside) 4-phosphate (33)
  • a solution of 32 (80 mg, 0.09 mmol) in EtOAc (4.0 mL) was hydrogenated (1 atm H 2 ) in the presence of 10% Pd(OH) 2 (12 mg) at rt overnight.
  • the reaction suspension was filtered through celite and the filtrate was concentrated under vacuo to provide 33 (quant.), which was used in the next step without further purification.
  • the filtrates Prior to concentration determination by LC/MS/MS, the filtrates were diluted (1 :1 , 1 :10, and 1 :100 or, if the results were outside of the calibration range, 1 :1000 and 1 :10000).
  • the calibration was based on six values ranging from 0.1 to 10 ⁇ g mL.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des composés de la formule (I) (I) où n est 0, 1 ou 2, R1 est aryle, hétéroaryle ou hétérocyclyle, et R2 et R3 sont, indépendamment l'un de l'autre, hydrogène ou un substituant tel que décrit dans la description et l'un parmi RA, RB, RC et RD est PO2(OH)2 et les autres sont hydrogène ; qui sont des médicaments disponibles par voie orale utile pour la prévention et le traitement d'infections bactériennes, en particulier d'infections urinaires provoquées par E. coli.
PCT/EP2012/060397 2011-06-03 2012-06-01 Dérivés de mannose phosphate en tant qu'antagonistes de l'adhésion bactérienne Ceased WO2012164074A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11168630 2011-06-03
EP11168630.9 2011-06-03

Publications (1)

Publication Number Publication Date
WO2012164074A1 true WO2012164074A1 (fr) 2012-12-06

Family

ID=44763685

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/060397 Ceased WO2012164074A1 (fr) 2011-06-03 2012-06-01 Dérivés de mannose phosphate en tant qu'antagonistes de l'adhésion bactérienne

Country Status (1)

Country Link
WO (1) WO2012164074A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014165107A3 (fr) * 2013-03-12 2015-02-26 Vertex Pharmaceuticals Incorporated Dérivés du mannose pour le traitement d'infections bactériennes
JP2016520618A (ja) * 2013-05-30 2016-07-14 ワシントン・ユニバーシティＷａｓｈｉｎｇｔｏｎ Ｕｎｉｖｅｒｓｉｔｙ 細菌感染症を治療するための化合物及び方法
US9598454B2 (en) 2012-12-18 2017-03-21 Vertex Pharmaceuticals Incorporated Mannose derivatives for treating bacterial infections
US9745253B2 (en) 2015-03-13 2017-08-29 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
WO2019076931A1 (fr) 2017-10-16 2019-04-25 Enterome Nouveaux outils pour évaluer l'efficacité thérapeutique des bloqueurs fimh
US10273260B2 (en) 2009-10-22 2019-04-30 Washington University Compounds and methods for treating bacterial infections
US10738070B2 (en) 2016-03-23 2020-08-11 Fimbrion Therapeutics, Inc. Mannose-derived antagonists of FimH useful for treating disease
US11111262B2 (en) 2018-07-10 2021-09-07 Glaxosmithkline Intellectual Property Development Limited C-mannoside compounds useful for the treatment of urinary tract infections
WO2024246474A1 (fr) * 2023-05-31 2024-12-05 Nanomedsyn Pro-ligands analogues du mannose-6-phosphate ou du mannose, conjugués comprenant lesdits pro-ligands et leurs utilisations pour des applications thérapeutiques
US12297223B2 (en) 2019-05-07 2025-05-13 Glaxosmithkline Intellectual Property Development Limited Compounds
US12351597B2 (en) 2019-06-19 2025-07-08 Glaxosmithkline Intellectual Property Development Limited Substituted biphenyl or phenylheteroaryl-mannosides as antagonists of FimH

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998021220A2 (fr) 1996-11-14 1998-05-22 Synsorb Biotech, Inc. Derives de saccharide
WO2005089733A2 (fr) 2004-03-23 2005-09-29 Vib Vzw Composes anti-adhesifs destines a la prevention et au traitement d'infections bacteriennes
WO2011050323A1 (fr) * 2009-10-22 2011-04-28 The Washington University Composés et méthodes pour le traitement d'infections bactériennes
WO2011073112A2 (fr) * 2009-12-14 2011-06-23 University Of Basel Dérivés de mannose utilisés en tant qu'antagonistes de l'adhésion bactérienne

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998021220A2 (fr) 1996-11-14 1998-05-22 Synsorb Biotech, Inc. Derives de saccharide
WO2005089733A2 (fr) 2004-03-23 2005-09-29 Vib Vzw Composes anti-adhesifs destines a la prevention et au traitement d'infections bacteriennes
WO2011050323A1 (fr) * 2009-10-22 2011-04-28 The Washington University Composés et méthodes pour le traitement d'infections bactériennes
WO2011073112A2 (fr) * 2009-12-14 2011-06-23 University Of Basel Dérivés de mannose utilisés en tant qu'antagonistes de l'adhésion bactérienne

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
A. IMBERTY; Y.M. CHABRE; R. ROY, CHEM. EUR J ., vol. 14, 2008, pages 7490 - 7499
B. FOXMAN, DIS. MON., vol. 49, 2003, pages 53 - 70
H. CONNELL; M. HEDLUND; W. AGACE; C. SVANBORG, ADV. DENT. RES., vol. 11, 1997, pages 50 - 58
HAODAN YUAN; NA LI; YURONG LAI, DRUG METABOLISM AND DISPOSITION, vol. 37, 2009, pages 1443 - 1447
I. OFEK; D.L. HASTY; N. SHARON, FEMS IMMUNOL MED MICROBIOL, vol. 38, 2003, pages 181 - 191
M. RUBENS; S.L. BUCHWALD, ACCOUNTS CHEM. RES., vol. 41, 2008, pages 1461 - 1473
N.A. BOKACH; V.Y. KUKUSHKIN, RUSS. CHEM. BULL., vol. 55, 2006, pages 1869 - 1882
P. CHOWDHURY; S.H. SACKS; N.S. SHEERIN, KIDNEY INT., vol. 66, 2004, pages 1334 - 1344
T. KLEIN ET AL., J. MED. CHEM., vol. 53, 2010, pages 8627 - 8641
T.W. GREENE; P.G.M. WUTS: "Protective Groups in Organic Synthesis", 1999, WILEY
TOBIAS KLEIN ET AL: "FimH Antagonists for the Oral Treatment of Urinary Tract Infections: From Design and Synthesis to in Vitro and in Vivo Evaluation", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 53, no. 24, 23 December 2010 (2010-12-23), pages 8627 - 8641, XP002620404, ISSN: 0022-2623, [retrieved on 20101124], DOI: 10.1021/JM101011Y *

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10273260B2 (en) 2009-10-22 2019-04-30 Washington University Compounds and methods for treating bacterial infections
TWI626247B (zh) * 2012-12-18 2018-06-11 維泰克斯製藥公司 用於治療細菌感染之甘露糖衍生物
US11634447B2 (en) 2012-12-18 2023-04-25 Vertex Pharmaceuticals Incorporated Mannose derivatives for treating bacterial infections
US9598454B2 (en) 2012-12-18 2017-03-21 Vertex Pharmaceuticals Incorporated Mannose derivatives for treating bacterial infections
US9963478B2 (en) 2012-12-18 2018-05-08 Vertex Pharmaceuticals Incorporated Mannose derivatives for treating bacterial infections
US10913761B2 (en) 2012-12-18 2021-02-09 Vertex Pharmaceuticals Incorporated 2,7-dibromospiro[fluorene-9,4′-piperidine] compounds
US10669298B2 (en) 2012-12-18 2020-06-02 Vertex Pharmaceuticals Incorporated Mannose derivatives for treating bacterial infections
CN105164142A (zh) * 2013-03-12 2015-12-16 沃泰克斯药物股份有限公司 用于治疗细菌感染的甘露糖衍生物
KR102249702B1 (ko) 2013-03-12 2021-05-10 버텍스 파마슈티칼스 인코포레이티드 세균 감염 치료용 만노스 유도체
US9890176B2 (en) 2013-03-12 2018-02-13 Vertex Pharmaceuticals Incorporated Mannose derivatives for treating bacterial infections
WO2014165107A3 (fr) * 2013-03-12 2015-02-26 Vertex Pharmaceuticals Incorporated Dérivés du mannose pour le traitement d'infections bactériennes
KR20150126692A (ko) * 2013-03-12 2015-11-12 버텍스 파마슈티칼스 인코포레이티드 세균 감염 치료용 만노스 유도체
RU2678327C2 (ru) * 2013-03-12 2019-01-28 Вертекс Фармасьютикалз Инкорпорейтед Производные маннозы для лечения бактериальных инфекций
CN105164142B (zh) * 2013-03-12 2019-03-08 沃泰克斯药物股份有限公司 用于治疗细菌感染的甘露糖衍生物
US9957289B2 (en) 2013-05-30 2018-05-01 Washington University Compounds and methods for treating bacterial infections
JP2016520618A (ja) * 2013-05-30 2016-07-14 ワシントン・ユニバーシティＷａｓｈｉｎｇｔｏｎ Ｕｎｉｖｅｒｓｉｔｙ 細菌感染症を治療するための化合物及び方法
US11919839B2 (en) 2015-03-13 2024-03-05 Valo Health, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
US10266487B2 (en) 2015-03-13 2019-04-23 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
US10988441B2 (en) 2015-03-13 2021-04-27 Valo Early Discovery, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
US9745253B2 (en) 2015-03-13 2017-08-29 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
US10508077B2 (en) 2015-03-13 2019-12-17 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
US10738070B2 (en) 2016-03-23 2020-08-11 Fimbrion Therapeutics, Inc. Mannose-derived antagonists of FimH useful for treating disease
WO2019076931A1 (fr) 2017-10-16 2019-04-25 Enterome Nouveaux outils pour évaluer l'efficacité thérapeutique des bloqueurs fimh
US11111262B2 (en) 2018-07-10 2021-09-07 Glaxosmithkline Intellectual Property Development Limited C-mannoside compounds useful for the treatment of urinary tract infections
US11697665B2 (en) 2018-07-10 2023-07-11 Fimbrion Therapeutics, Inc. C-mannoside compounds useful for the treatment of urinary tract infections
US12297223B2 (en) 2019-05-07 2025-05-13 Glaxosmithkline Intellectual Property Development Limited Compounds
US12351597B2 (en) 2019-06-19 2025-07-08 Glaxosmithkline Intellectual Property Development Limited Substituted biphenyl or phenylheteroaryl-mannosides as antagonists of FimH
WO2024246474A1 (fr) * 2023-05-31 2024-12-05 Nanomedsyn Pro-ligands analogues du mannose-6-phosphate ou du mannose, conjugués comprenant lesdits pro-ligands et leurs utilisations pour des applications thérapeutiques
FR3149188A1 (fr) * 2023-05-31 2024-12-06 Nanomedsyn Pro-ligands, conjugués comprenant lesdits pro-ligands et leurs utilisations pour des applications thérapeutiques

Similar Documents

Publication Publication Date Title
WO2012164074A1 (fr) Dérivés de mannose phosphate en tant qu'antagonistes de l'adhésion bactérienne
AU2010333017B2 (en) Mannose derivatives as antagonists of bacterial adhesion
US8343936B2 (en) Antibacterial agents
AU2004260760B2 (en) Novel compounds
US9890176B2 (en) Mannose derivatives for treating bacterial infections
JP7405752B2 (ja) グルコピラノシル誘導体及びその使用
WO2013038429A2 (fr) Nouveaux inhibiteurs de sglt
JP2008524162A (ja) グルコピラノシル置換ベンゼン誘導体、該化合物を含む薬物、その使用及びその製造方法
WO2014055474A1 (fr) Dérivés de mannose pour traiter les infections bactériennes
CA2869416A1 (fr) Derives de mannose pour le traitement d'infections bacteriennes
EP2717689A2 (fr) Nouveaux inhibiteurs sglt
ITMI20080846A1 (it) Composti a struttura glicosidica attivi nella terapia di stati infiammatori locali e sistemici
CN103270033B (zh) C-芳基葡糖苷衍生物及其制备方法和应用
CN106674245A (zh) 吡喃葡萄糖基衍生物的制备及医药上的应用
CN110467646A (zh) 双核苷酸前体药物
HK1174926B (en) Mannose derivatives as antagonists of bacterial adhesion
JP2006232825A (ja) 医薬組成物
HK1209755A1 (en) Mannose derivatives for treating bacterial infections

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12725040

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12725040

Country of ref document: EP

Kind code of ref document: A1