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1. WO2010028487 - BIDESMOSIDIC BETULIN AND BETULINIC ACID DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS

Publication Number WO/2010/028487
Publication Date 18.03.2010
International Application No. PCT/CA2009/001255
International Filing Date 10.09.2009
IPC
C07J 53/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
JSTEROIDS
53Steroids in which the cyclopentahydrophenanthrene skeleton has been modified by condensation with carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms
A61K 31/704 2006.01
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
70Carbohydrates; Sugars; Derivatives thereof
7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
7034attached to a carbocyclic compound, e.g. phloridzin
704attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin, digitoxin
A61P 35/00 2006.01
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
G01N 33/50 2006.01
GPHYSICS
01MEASURING; TESTING
NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
33Investigating or analysing materials by specific methods not covered by groups G01N1/-G01N31/131
48Biological material, e.g. blood, urine; Haemocytometers
50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
C07H 15/256 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
15Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
20Carbocyclic rings
24Condensed ring systems having three or more rings
256Polyterpene radicals
CPC
A61K 31/704
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
70Carbohydrates; Sugars; Derivatives thereof
7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
7034attached to a carbocyclic compound, e.g. phloridzin
704attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
A61P 35/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
C07J 63/008
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
JSTEROIDS
63Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
008Expansion of ring D by one atom, e.g. D homo steroids
G01N 33/5091
GPHYSICS
01MEASURING; TESTING
NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
33Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
48Biological material, e.g. blood, urine
50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
5005involving human or animal cells
5091for testing the pathological state of an organism
G01N 33/57415
GPHYSICS
01MEASURING; TESTING
NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
33Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
48Biological material, e.g. blood, urine
50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
53Immunoassay; Biospecific binding assay; Materials therefor
574for cancer
57407Specifically defined cancers
57415of breast
G01N 33/57419
GPHYSICS
01MEASURING; TESTING
NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
33Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
48Biological material, e.g. blood, urine
50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
53Immunoassay; Biospecific binding assay; Materials therefor
574for cancer
57407Specifically defined cancers
57419of colon
Applicants
  • UNIVERSITÉ DU QUÉBEC À CHICOUTIMI [CA]/[CA] (AllExceptUS)
  • PICHETTE, André [CA]/[CA] (UsOnly)
  • LEGAULT, Jean [CA]/[CA] (UsOnly)
  • GAUTHIER, Charles [CA]/[CA] (UsOnly)
Inventors
  • PICHETTE, André
  • LEGAULT, Jean
  • GAUTHIER, Charles
Agents
  • GOUDREAU GAGE DUBUC
Priority Data
61/095,81510.09.2008US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) BIDESMOSIDIC BETULIN AND BETULINIC ACID DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS
(FR) DÉRIVÉS DE BÉTULINE BIDESMOSIDIQUE ET D'ACIDE BÉTULINIQUE, ET LEURS UTILISATIONS EN TANT QU'AGENTS ANTICANCÉREUX
Abstract
(EN)
The instant application is directed to bidesmosidic betulin and betulinic acid saponin derivatives of formula (I), and use thereof as antitumor agents. In particular, said compounds are effective in treating lung carcinomas, colorectal adenocarcinomas, breast adenocarcinomas, and prostate adenocarcinomas. Methods of synthesizing said compounds through selective glycosylation of the C-28 and C-3 position, and diagnostic methods for identifying tumours suitable for treatment by said compounds are also disclosed.
(FR)
La présente invention porte sur des dérivés de bétuline bidesmosidique et de saponines d'acide bétulinique de la formule (I) et sur leur utilisation en tant qu'agents anticancéreux. En particulier, lesdits composés sont efficaces pour le traitement des carcinomes du poumon, des adénocarcinomes colorectaux, des adénocarcinomes du sein et des adénocarcinomes de la prostate. L'invention porte également sur des procédés de synthèse desdits composés par la glycosylation sélective des positions C-28 et C-3 et sur des méthodes de diagnostic pour l'identification de tumeurs se prêtant à un traitement par lesdits composés.
Also published as
Latest bibliographic data on file with the International Bureau