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
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: 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