(19)
(11) EP 1 475 094 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:
12.01.2011 Bulletin 2011/02

(45) Mention of the grant of the patent:
28.07.2010 Bulletin 2010/30

(21) Application number: 03010184.4

(22) Date of filing: 06.05.2003
(51) International Patent Classification (IPC): 
A61K 31/505(2006.01)
 C07D 487/04(2006.01)

(54)

Pyrazolo[4,3-D]pyrimidines, process for their preparation and methods of use

Pyrazolo[4,3-D]pyrimidines, verfahren zur ihre herstellung und deren verwendung

Pyrazolo[4,3-D]pyrimidines, procede de preparation et d'utilisation

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

(43) Date of publication of application:
10.11.2004 Bulletin 2004/46

(73) Proprietors:
  • Ústav Experimentální Botaniky AV CR, v.v.i. (Institute of Experimental Botany Academy of Sciences of the Czech Republic, PRO)
    165 02 Praha 6 (CZ)
  • Universita Palackeho v Olomouci
    771 47 Olomouc (CZ)

(72) Inventors:
  • Moravcova, Daniela
    34101 Horzdovice (CZ)
  • Havlicek, Libor
    14104 Praha 4 (CZ)
  • Krystof, Vladimir
    70200 Ostrava (CZ)
  • Lenobel, Rene
    73802 Frydek Mistek (CZ)
  • Binarova, Pavla
    77200 Olomouc (CZ)
  • Mlejnek, Petra
    60200 Brno (CZ)
  • Vojtesek, Borek
    66442 Modrice (CZ)
  • Uldrijan, Stjepan
    62100 Brno (CZ)
  • Schmülling, Thomas
    14052 Berlin (DE)
  • Strnad, Miroslav
    77900 Olomouc (CZ)

(74) Representative: Grund, Martin 
GRUND Intellectual Property Group Postfach 44 05 16
80754 München
80754 München (DE)


(56) References cited: : 
WO-A-01/18170
US-A- 1 530 747
 DE-A- 10 060 388
US-A- 4 282 361
   
  • ELLAMES G J ET AL: "THE SYNTHESES OF ACYCLOFORMYCINS AND 5-AMINO-3-(2-HYDROXYETHOXY)-METH YLPYRAZOLO[4,3-D]PYRIMIDIN-7(6H)- ONE AN ANALOGUE OF THE ANTIVIRAL ACYCLOGUANOSINE" JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 10, 1 October 1985 (1985-10-01), pages 2087-2091, XP002047056 ISSN: 0300-922X
  • LONG ROBERT A ET AL: "Derivatives of the new ring system pyrazolo[4,3-d]-v-triazine and the synthesis of 5,7-disubstituted 3-methylpyrazolo[4,3- d]pyrimidines and 5,7-disubstituted 3-methylpyrazolo[4,3- d]pyrimidine 6-oxides which are structurally related to the nucleoside antibiotics formycin and formycin B" JOURNAL OF HETEROCYCLIC CHEMISTRY, HETEROCORPORATION. PROVO, US, vol. 7, no. 4, 1970, pages 863-869, XP002208252 ISSN: 0022-152X
  • HECHT SM ET AL: "cytokinins: development of a potent antagonist" PROCEEDING OF THE NATIONAL ACADEMIE OF SCIENCE USA, vol. 68, no. 10, 1971, pages 2608-2610, XP009015448 USA
  • HECHT SM ET AL: "question of the ribosyl moiety in the promotion of callus growth by exogenously added cytokinins" BIOCHEMISTRY, vol. 10, no. 23, 1971, pages 4224-4228, XP002250881 USA
  • HECHT SM ET AL: "on the activation of cytokinins" THE JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 250, no. 18, 1975, pages 7343-7351, XP002250882 USA
  • SKOOG F ET AL: "cytokinin antagonists: synthesis and physiological effects of 7-substituted 3-methylpyrazolo[4,3-d]pyrimidines" PHYTOCHEMISTRY, vol. 12, 1973, pages 25-37, XP009015452 UK
  • GREGORINI G ET AL: "biological effects of cytokinin antagonists 7-(pentylamino) and 7-(benzylamino)-3-methylpyrazolo[4,3-d]pyr imidines on suspension-cultured tobacco cells" PLANT PHYSIOLOGY, vol. 65, 1980, pages 363-367, XP001154399
  • HECHT SM ET AL: "competitive inhibition of beef heart cyclic AMP phosphodiesterase by cytokinins and related compounds" PROCEEDING OF THE NATIONAL ACADEMIE OF SCIENCES USA, vol. 71, no. 12, 1974, pages 4670-4674, XP009015447 USA
  • DIZENGREMEL P ET AL: "inhibition by adenine derivatives of the cyaninde insensitive electron transport pathway of plant mitochondria" PLANT PHYSIOLOGY, vol. 70, 1982, pages 585-589, XP001154398
  • BIANCO-COLOMANS J : "effect of a cytokinin antagonist on cytokinin and light-dependent amaranthin synthesis in amaranthus tricolor seedlings" JOURNAL OF PLANT GROWTH REGULATION, vol. 2, no. 4, 1984, pages 281-287, XP009015443 Germany
  • PARKER CW ET AL: "inhibitors of two enzymes which metabolize cytokinins" PHYTOCHEMISTRY, vol. 25, no. 2, 1986, pages 303-310, XP001154032 GB
  • AUNG LH: "Action of cytokinins and anticytokinins on cotyledonary bud growth of lycopersicon esculentum mill" BIOLOGIA PLANTARUM, vol. 28, no. 6, 1986, pages 407-411, XP009015451 praha
  • WIERZCHOWSKI J ET AL: "luminiscence studies on formycin, its aglycone, and thier N-methyl derivatives: tautomerism, sites of protonation and phototautomerism" PHOTOCHEMISTRY AND PHOTOBIOLOGY, vol. 35, 1982, pages 445-458, XP009015440 GB
  • ROBINS RK ET AL: "potential purine antagonists V. synthesis of some 3-methyl-5,7-substituted pyrazolo[4,3-d]pyrimidines" THE JOURNAL OF ORGANIC CHEMISTRY, vol. 21, no. 8, 1956, pages 833-836, XP002250883 USA
  • WIERZCHOWSKI J ET AL: "analogues of formycins A and B: synthesis and some properties of methyl derivatives of 7-amino and 7-keto pyrazolo[4,3-d]pyrimidines" ACTA BIOCHIMICA POLONICA, vol. 27, no. 1, 1980, pages 35-56, XP009015441 Poland
  • BUCHANAN JG ET AL: "C-nucleoside studies part 18 the synthesis of C-nucleoside analogues of the antiviral agent (S)-9-(2,3-dihydroxypropyl)adenine" JOURNAL OF THE CHEMICAL SOCIETY PERKIN TRANSACTIONS I, 1985, pages 1425-1430, XP009015442 GB
   
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).