(19)
(11) EP 1 720 881 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:
16.01.2013 Bulletin 2013/03

(45) Mention of the grant of the patent:
12.12.2012 Bulletin 2012/50

(21) Application number: 05717846.9

(22) Date of filing: 01.03.2005
(51) International Patent Classification (IPC): 
C07D 487/04(2006.01)
A61K 31/5517(2006.01)
 C07D 519/00(2006.01)
A61P 35/00(2006.01)
(86) International application number:
PCT/GB2005/000768
(87) International publication number:
WO 2005/085251 (15.09.2005 Gazette 2005/37)

(54)

11-HYDROXY-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPIN-5-ONE DERIVATIVES AS KEY INTERMEDIATES FOR THE PREPARATION OF C2 SUBSTITUTED PYRROLOBENZODIAZEPINS

11-HYDROXY-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPIN-5-ONDERIVATE ALS SCHLÜSSELZWISCHENPRODUKTE ZUR HERSTELLUNG C2-SUBSTITUIERTER PYRROLOBENZODIAZEPINE

DERIVES DE 11-HYDROXY-5H-PYRROLO[2,1-C][1,4] BENZODIAZEPINE-5-ONE EN TANT QU'INTERMEDIAIRES CLES POUR LA PREPARATION DE PYRROLOBENZODIAZEPINES SUBSTITUEES C2

(84) Designated Contracting States:
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

(30) Priority: 01.03.2004 GB 0404575
01.12.2004 GB 0426392

(43) Date of publication of application:
15.11.2006 Bulletin 2006/46

(60) Divisional application:
10174003.3 / 2270010

(73) Proprietor: Spirogen Sàrl
St-Légier-La Chiésaz (CH)

(72) Inventors:
  • HOWARD, Philip Wilson
    St Albans Hertfordshire AL1 1LS (GB)
  • GREGSON, Stephen John
    London Greater London SE28 0HJ (GB)

(74) Representative: Watson, Robert James et al
Mewburn Ellis LLP 33 Gutter Lane
London EC2V 8AS
London EC2V 8AS (GB)


(56) References cited: : 
WO-A-00/12508
 WO-A-2004/043963
   
  • CHEN ET AL: "A novel approach to the synthesis of cytotoxic C2?C3 unsaturated pyrrolo[2,1-c][ and ]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 6, 27 February 2004 (2004-02-27), pages 1547-1549, XP002329273
  • KANG ET AL: "Synthesis of a novel C2-aryl substituted 1,2-unsaturated pyrrolobenzodiazepine" CHEMICAL COMMUNICATIONS, vol. 14, 11 June 2003 (2003-06-11), pages 1688-1689, XP002329274
  • GREGSON ET AL: "Synthesis of the first examples of A-C8/C-C2 amide-Linked pyrrolo[2,1-c][1,4]benzodiazepine dimers" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 13, no. 14, 31 March 2003 (2003-03-31), pages 2277-2280, XP002329063
  • COOPER ET AL: "Synthesis of novel C2-aryl pyrrolobenzodiazepines (PBDs) as potential antitumour agents" CHEMICAL COMMUNICATIONS, vol. 16, 5 July 2002 (2002-07-05), pages 1764-1765, XP002329275
  • GREGSON ET AL: "Synthesis of the first example of a c2-C3/C2?-C3?-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 11, no. 21, 27 August 2001 (2001-08-27), pages 2859-2862, XP002329276
  • GREGSON ET AL: "Effect of C2/C3-endo unsaturation on the cytotoxicity and dna-binding reactivity of pyrrolo[2,1-c][1,4]benzodiazepines" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 10, no. 16, 14 April 2000 (2000-04-14), pages 1849-1852, XP004216014
  • FUKUYAMA ET AL: "Total synthesis of (+)-porothramycin B" TETRAHEDRON LETTERS, vol. 34, no. 16, 16 April 1993 (1993-04-16), pages 2577-2580, XP002135999
  • TIBERGHIEN ET AL: "Application of the Stille coupling reaction to the synthesis of C2-substituted endo-exo unsaturated pyrrolo[2,1-c][1,4]benzodiazepines (PBDs)" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 20, 1 September 2004 (2004-09-01), pages 5041-5044, XP002329277
 
Remarks:
The file contains technical information submitted after the application was filed and not included in this specification
 
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).