Patent number: 8394362
Abstract: The invention concerns a gem-difluorinated C-glycopeptide compound of formula (I) in which N is an integer between 1 and 5, R4=H, AA1, AA1-AA2 and R5=OH, AA1, AA1, AA2, with AA1, and AA2 are independents groups and represent amino acids with a non-functionalized side chain and R1, R2, R3 are independent groups and one of them is equal to formula (II), in which n is an integer between 3 and 4, Y, Y? are independent groups in which Y, Y?=H, OR, N3, NR?R?, SR??, where R=H, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, acetate group, R?, R???H, alkyl, allyl, benzyl, tosylate group, C(?O)-alkyl, C(?O)?Bn, R??=H, alkyl, acetate group, R6 is notably a group H, CH3, CH2OH, CH2-Glycoside group, CH2-OGP in which GP is a protector group such as an alkyl, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tertbutyldiphenylsilyl, acetate group,; and R7=OH, OGP?, NH2, N3, NHGP?, NGP?GP? in which GP? and GP? is or not a protector group such as an alkyl, benzyl, trimethylsilyl, tertbutyldimethyl
Type:
Grant
Filed:
December 2, 2005
Date of Patent:
March 12, 2013
Assignee:
Institut National des Sciences Appliquees de Rouen (INSA)
Inventors:
Jean-Charles Quirion, Géraldine Castelot-Deliencourt-Godefroy
Patent number: 8236935
Abstract: The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents II or a benzyl, acetyl, benzoyl alkyl group, R1 and R2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl protective group or an acetal group of the CR?R? type, where R? and R? may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R4 represents OR?, NGR?GR?, N3, or a phthalimide, where R? represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR? and GR? may be identical or different and represent II or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R5 represents a free or protected hydroxyl group or a halogen, R6 represents H or an alkyl, acetyl, benz
Type:
Grant
Filed:
April 24, 2007
Date of Patent:
August 7, 2012
Assignee:
Institut National des Sciences Appliquees de Rouen (INSA)
Inventors:
Jean-Charles Quirion, Geraldine Castle Deliencourt-Godefroy, Christophe Audouard
Publication number: 20120190648
Abstract: The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt, a stereoisomer or a mixture in all proportions of stereoisomers thereof, in particular a mixture of enantiomers, such as a racemic mixture, wherein R represents a (C1-C6)alkyl or (C1-C6)alkenyl group, optionally substituted by one or more groups chosen among an halogen atom, ORa, SRb, NRcRd, PO(ORe)(ORf), CO2Rg, SO2Rh SO3R1, P0(0H)(CH(0H)Rk), CN, N3 and NH—C(?NH)NH2, with Ra, Rb, Rc and Rd, representing, independently of each other, an hydrogen atom, a (C1-C6)alkyl group or a —CO—(C1-C6)alkyl group, Re, Rf, Rg, Rh and R1 representing, independently of each other, an hydrogen atom or a (C1-C6)alkyl group, and Rk representing an aryl or heteroaryl group, said group being optionally substituted by one or more groups selected from an halogen atom and NO2, as well as to the use thereof and to a process for preparing such a compound, to a pharmaceutical composition containing it and to synthesis intermediates.
Type:
Application
Filed:
July 23, 2010
Publication date:
July 26, 2012
Inventors:
Philippe Jubault, Jean-Charles Quirion, Gerald Lemonnier, Cedric Lion
Publication number: 20100041584
Abstract: The invention concerns a gem-difluorinated C-glycopeptide compound of formula (I) in which N is an integer between 1 and 5, R4=H, AA1, AA1-AA2 and R5=OH, AA1, AA1.AA2, with AA1, and AA2 are independents and representing amino acids with a non functionalised side chain and R1, R2, R3 are independent groups and one of them is egal to formula (II), in which n is an integer between 3 and 4, Y, Y? are independent groups in which Y, Y?=H, OR, N3, NR?R?, SR??, where R=H, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, acetate group, R?, R?=H, alkyl, allyl, benzyl, tosylate group, C(?O) alkyl, C(?O)Bn.
Type:
Application
Filed:
December 2, 2005
Publication date:
February 18, 2010
Applicant:
Institut National Des Science Appliquees de Rouen (INSA)
Inventors:
Jean-Charles Quirion, Géraldine Castelot-Deliencourt-Godefroy
Publication number: 20090318675
Abstract: The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents II or a benzyl, acetyl, benzoyl alkyl group, R1 and R2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl protective group or an acetal group of the CR?R? type, where R? and R? may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R4 represents OR?, NGR?GR?, N3, or a phthalimide, where R? represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR? and GR? may be identical or different and represent II or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R5 represents a free or protected hydroxyl group or a halogen, R6 represents H or an alkyl, acetyl, benz
Type:
Application
Filed:
April 24, 2007
Publication date:
December 24, 2009
Inventors:
Jean-Charles Quirion, Géraldine Lho-Ircof Castlot Deliencourt-Godefroy, Christophe Audouard
Publication number: 20090318678
Abstract: The invention concerns a C-glycoside compound of formula (I); wherein: n is equal to 1 or 2; Y represents H or halogen; X is an alkyl chain bearing at least one amino, amide, acid, ester, carbonyl, alcohol, aryl function or a carbonyl, ester amide, amino, alcohol group; the R's, identical or different, represent a OH or OR? group where R? is an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl group or one or more sugars; R1 represents OR?, NR?R??, N3, or a phthalamide with R? and R??, identical or different, represent H or an alkyl, aryl, benzyl, benzoyl, acetyl, alkoxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl group; R2 represents H or halogen or a OH, OR, NR?R?? or N3 group, as well as derivatives thereof in physiologically or pharmaceutically acceptable base, mineral or organic acid-addition salt, hydrate or solvate form.
Type:
Application
Filed:
April 23, 2007
Publication date:
December 24, 2009
Applicant:
TFCHEM
Inventors:
Géraldine Castelot-Deliencourt-Godefroy, Jean-Charles Quirion, Philippe Jubault, Ludivine Zoute
Publication number: 20090311203
Abstract: The invention relates to a gem-difluoride C-glycopeptide compound with formula I where n is an integer equal to 3 or 4, R represents a hydrogen atom, an alkyl, benzyl, acetyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl group, R? represents OR, NR?R?, N3, or a phthalimide, R? and R? represent a hydrogen atom or an alkyl, aryl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl group, R1 represents a hydrogen atom or an alkyl, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl group, R1 may consist of an amino acid if R2 represents only OR, R2 includes an amino acid if R1 represents a hydrogen atom or an alkyl, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl group, R2 represents OR when R1 represents an amino acid, R3 represents a hydrogen atom or a free or protected alcohol function.
Type:
Application
Filed:
April 26, 2007
Publication date:
December 17, 2009
Applicant:
INSTITUT NATIONAL DES SCIENCES APPLIQUEES DE ROUEN (INSA)
Inventors:
Géraldine Castelot Deliencourt-Godefroy, Jean-Charles Quirion