(19)
(11) EP 2 511 273 B8

(12) CORRECTED EUROPEAN PATENT SPECIFICATION
Note: Bibliography reflects the latest situation

(15) Correction information:
Corrected version no 1 (W1 B1)

(48) Corrigendum issued on:
26.06.2019 Bulletin 2019/26

(45) Mention of the grant of the patent:
15.05.2019 Bulletin 2019/20

(21) Application number: 11305458.9

(22) Date of filing: 15.04.2011
(51) International Patent Classification (IPC): 
C07D 311/58(2006.01)
C07D 407/04(2006.01)
C07D 215/14(2006.01)
A61K 31/352(2006.01)
 C07D 405/04(2006.01)
C07C 59/66(2006.01)
A61K 31/192(2006.01)
A61K 31/473(2006.01)

(54)

Inhibitors of viral replication, their process of preparation and their therapeutical uses

Inhibitoren der Virenreplikation, Verfahren zu deren Herstellung und deren therapeutische Verwendung

Inhibiteurs de la réplication virale, leur procédé de préparation et leurs utilisations thérapeutiques

(84) Designated Contracting States:
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

(43) Date of publication of application:
17.10.2012 Bulletin 2012/42

(73) Proprietor: HIVIH
93230 Romainville (FR)

(72) Inventors:
  • Chasset, Sophie
    77176 NANDY (FR)
  • Chevreuil, Francis
    60500 CHANTILLY (FR)
  • Ledoussal, Benoit
    77580 BOULEURS (FR)
  • Le Strat, Frédéric
    93220 GAGNY (FR)

(74) Representative: Lavoix 
62, rue de Bonnel
69448 Lyon Cedex 03
69448 Lyon Cedex 03 (FR)


(56) References cited: : 
WO-A1-2007/131350
WO-A1-2009/062285
WO-A1-2009/062289
WO-A1-2010/007120
WO-A1-2010/130034
WO-A1-2011/015641
WO-A1-2012/003498
US-A- 4 736 057
 WO-A1-2008/128344
WO-A1-2009/062288
WO-A1-2009/062308
WO-A1-2010/055911
WO-A1-2010/130842
WO-A1-2012/003497
WO-A2-2007/106469
US-A- 4 872 918
   
  • PARMAR V S ET AL: "SYNTHESIS, ANTIMICROBIAL AND ANTIVIRAL ACTIVITIES OF NOVEL POLYPHENOLIC COMPOUNDS", INDIAN JOURNAL OF CHEMISTRY, vol. 35B, no. 3, 1 March 1996 (1996-03-01) , pages 220-232, XP001022822, JODHPUR, IN
  • DATABASE MEDLINE [Online] US NATIONAL LIBRARY OF MEDICINE (NLM), BETHESDA, MD, US; July 1998 (1998-07), GORDON Y J ET AL: "The effects of topical nonsteroidal anti-inflammatory drugs on adenoviral replication.", XP002663374, Database accession no. NLM9682703 & GORDON Y J ET AL: "The effects of topical nonsteroidal anti-inflammatory drugs on adenoviral replication.", ARCHIVES OF OPHTHALMOLOGY JUL 1998 LNKD- PUBMED:9682703, vol. 116, no. 7, July 1998 (1998-07), pages 900-905, ISSN: 0003-9950
  • DATABASE WPI Week 200602 Thomson Scientific, London, GB; AN 2006-013202 XP002663375, & IN DEL 200500540 A1 (SINGH G) 26 August 2005 (2005-08-26)
  • DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1966, LUTSENKO, V. V.: "Some .alpha.-methozyacetic acids of cyclohexane and 3-cyclohexane series", XP002663376, retrieved from STN Database accession no. 1967:411258 & LUTSENKO, V. V.: "Some .alpha.-methozyacetic acids of cyclohexane and 3-cyclohexane series", LIETUVOS TSR MOKSLU AKADEMIJOS DARBAI, SERIJA B: CHEMIJA, TECHNIKA, FIZINE GEOGRAFIJA , (3), 69-76 CODEN: LMDBAL; ISSN: 0132-2729, 1966,
  • DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1973, BERLIN, YU. A. ET AL: "Olivomycin and related antibiotics. XXVI. Absolute configuration of olivin and chromomycinone", XP002663377, retrieved from STN Database accession no. 1973:4473 & BERLIN, YU. A. ET AL: "Olivomycin and related antibiotics. XXVI. Absolute configuration of olivin and chromomycinone", KHIMIYA PRIRODNYKH SOEDINENII , 8(4), 526-34 CODEN: KPSUAR; ISSN: 0023-1150, 1972,
  • DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1974, BERLIN, YU. A. ET AL: "Olivomycin and related antibiotics. XXXI. Stereochemistry of chromocycline", XP002663378, retrieved from STN Database accession no. 1974:3304 & BERLIN, YU. A. ET AL: "Olivomycin and related antibiotics. XXXI. Stereochemistry of chromocycline", KHIMIYA PRIRODNYKH SOEDINENII , 9(4), 532-9 CODEN: KPSUAR; ISSN: 0023-1150, 1973,
  • J. M. SAYER ETAL.: "Conformational effects in the hydrolyses of rigid benzylic epoxides:", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 104, no. 7, 1982, pages 1972-1978, XP002663379, USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. ISSN: 0002-7863
  • EMIL BUCHTA ET AL: "Über tri-, tetra- und pentacyclische Verbindungen,", LIEBIGS ANNALEN DER CHEMIE, vol. 674, 1964, pages 129-152, XP002663380,
  • P. DOSTERT ET AL.: "Synthèse d'analogues partiellement saturés des neuroleptiques tricycliques...", HELVETICA CHIMICA ACTA., vol. 53, no. 211, 1970, pages 1813-1827, XP002663381, CHVERLAG HELVETICA CHIMICA ACTA, BASEL. ISSN: 0018-019X
  • RICHARD B. TURNER ET AL.: "The structure and total synthesis of cassaic acid", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 88, no. 8, April 1966 (1966-04), pages 1766-1775, XP002663382, USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. ISSN: 0002-7863
  • D. L. TURNER: "Cyclized products from the Stobbe condensation...", JOURNAL OF THE CHEMICAL SOCIETY., vol. 73, March 1951 (1951-03), pages 1284-1287, XP002663383, GBCHEMICAL SOCIETY. LETCHWORTH. ISSN: 0368-1769
  • C. DAVID GUTSCHE: "The stereochemistry of the 2-phenylcyclohexanecarboxylic acids and...", JOURNAL OF THE CHEMICAL SOCIETY, SECTION C: ORGANIC CHEMISTRY., vol. 70, December 1948 (1948-12), pages 4150-4154, XP002663384, GBCHEMICAL SOCIETY. LETCHWORTH. ISSN: 0022-4952
  • YOSHIAKI IIDA ET AL.: "Stereochemical studies of alkyl methylcyclohexaneacetates...", AGRICULTURAL AND BIOLOGICAL CHEMISTRY., vol. 45, no. 7, 1981, pages 1553-1559, XP002663385, JAPAN SOC. FOR BIOSCIENCE, BIOTECHNOLOGY AND AGROCHEM ISSN: 0002-1369
  • DATABASE MEDLINE [Online] US NATIONAL LIBRARY OF MEDICINE (NLM), BETHESDA, MD, US; 2002, ZHANG GUO-GANG ET AL: "A new compound from Forsythia suspensa (Thunb.) Vahl with antiviral effect on RSV.", XP002663386, Database accession no. NLM15277088 & ZHANG GUO-GANG ET AL: "A new compound from Forsythia suspensa (Thunb.) Vahl with antiviral effect on RSV.", JOURNAL OF HERBAL PHARMACOTHERAPY 2002 LNKD- PUBMED:15277088, vol. 2, no. 3, 2002, pages 35-40, ISSN: 1522-8940
  • ANNE MARIE TOUZIN: "RSACTION D'BYDIIDXYALXYLATION DES ENOLATRS D'ESTSR a EiSTSROSUSSTITUSS.SYNTEFSE D'ETSRRS D'ENOL D'a CETCESTERS ET DE B CEIOESTERS a AUCOXYLSS", TETRAHEDRON LETTERS., no. 18, 1975, pages 1477-1480, XP002669320, NL ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM. ISSN: 0040-4039
  • HIROSHI SUGINOME ET AL.: "Photoinduced transformations. Part 38. Photoreactions of 17-ethoxycarbonylmethylene-etiojerva-5,13( 17)- and -5,16-diene-3beta,11beta,20xi-triol 3,20-Diacetate 11-Nitrites-", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1., no. 6, 1978, pages 612-618, XP002669321, GB CHEMICAL SOCIETY. LETCHWORTH. ISSN: 0300-922X
  • M MEDARDE ET AL.: "Synthesis and evaluation of cardiotonic activity of simple butenolides II", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 28, 1993, pages 887-892, XP002669322, ED. SCIENTIFIQUE ELSEVIER, PARIS, FR
  • JOHN BUTERA ET AL.: "Computer-assisted design and synthesis of novel aldose reductase inhibitors", JOURNAL OF MEDICINAL CHEMISTRY., vol. 32, no. 4, April 1989 (1989-04), pages 757-765, XP002669323, USAMERICAN CHEMICAL SOCIETY. WASHINGTON. ISSN: 0022-2623
  • MELVIN S. NEWMAN: "The synthesis of 5-methylchrysene and related compounds", JOURNAL OF THE CHEMICAL SOCIETY., vol. 62, no. 4, April 1940 (1940-04), pages 870-874, XP002669324, GBCHEMICAL SOCIETY. LETCHWORTH. ISSN: 0368-1769
  • BRADSHER, CHARLES ET AL.: "Aromatic Cyclodehydration. XXVIII. 9,10-Dialkylphenanthrenes by Cyclization of Ketones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 76, no. 16, August 1954 (1954-08), pages 4140-4143, XP002669325, US AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. ISSN: 0002-7863
  • WANG, DONG-HUI ET AL.: "Versatile Pd(II)-Catalyzed C-H Activation/Aryl-Aryl Coupling of Benzoic and Phenyl Acetic Acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 130, no. 52, 2008, pages 17676-17677, XP002669326, USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. ISSN: 0002-7863
  • RYABUKHIN, SERGEY ET AL.: "Chlorotrimethylsilane-Mediated Friedländer Synthesis of PolysubstitutedQuinolines", SYNTHESIS., no. 8, P14706SS, 2007, pages 1214-1224, XP002669327, DEGEORG THIEME VERLAG, STUTTGART. ISSN: 0039-7881
  • DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1995, ASSY, M. G. ET AL: "The synthesis of pyridazine and fused pyridazine", XP002669328, retrieved from STN Database accession no. 1995:769330
  • NICOLAOU, K. ET AL.: "Total synthesis of Sporolide B and 9-epi-Sporolide B", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 132, no. 32, 2010, pages 11350-11363, XP002669329, USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. ISSN: 0002-7863
  • DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 24 January 2010 (2010-01-24), XP002669330, retrieved from STN
  • DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 29 July 2009 (2009-07-29), XP002669331, retrieved from STN
  • DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 23 April 2008 (2008-04-23), XP002669332, retrieved from STN
  • DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 3 February 2011 (2011-02-03), XP002669333, retrieved from STN
  • DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2 February 2011 (2011-02-02), XP002669334, retrieved from STN
   
Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).