185381-95-7

Upstream product

• 171241-94-4 methyl 5-( tert-butoxycarbonyl)amino-4-azido-2,6-anhydro-3,4,5-trideoxydideoxy-D-glycero-D-galactonon-2-enonate 
• 27906-91-8 N-propyl-2-phenylethylamine 
• 343934-44-1 (4S,5R,6R)-5-Amino-4-azido-6-(phenethyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 185382-33-6 (2R,3R,4S)-4-Azido-3-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-methyl ester 

Relevant academic research and scientific papers

Sialidase inhibitors related to zanamivir. Further SAR studies of 4-amino-4H-pyran-2-carboxylic acid-6-propylamides

SAR investigations of the 4- and 5-positions of a series of 4-amino-4H-pyran-2-carboxylic acid 6-carboxamides are reported. Potent inhibitors of influenza A sialidase with marked selectivity over the influenza B enzyme were obtained when the basic 4-amino substituent was replaced by hydroxyl or even deleted. Modifications at the 5-position exhibited a tight steric requirement, with trifluoroacetamide being optimal.

6-Carboxamido dihydropyran derivatives

Compounds of formula (I), STR1 wherein R1 represents OR5, SR5, NR5 R6, N(OR5)R6 or N(NR5 R6)R6 ; X represents OH, N3, NR3 R4 or NR4 CO2 R15 ; Y represents H or NHR2 ; R2 represents a group SO2 R7 or COR7 ; R3 represents H, C1-6 alkyl or C(=NR8)NR9 R10 ; R4 represents H or C1-6 alkyl; R5 represents H, C1-20 alkyl, C3-8 cycloalkyl, C2-20 alkenyl, C2-20 alkynyl, CHR11 COR12 or C1-20 alkyl substituted by one or more groups selected from NR13 R14, NR13 COR14, CO2 R13, OR13, C3-8 cycloalkyl and optionally substituted aryl; each R6 independently represents H, C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-20 alkynyl, aryl or C1-4 alkyl substituted by one or more groups selected from NR13 R14, COR13, C3-8 cycloalkyl, CN, N3, OR13 and optionally substituted aryl; or R5 and R6 together form a C2-6 hydrocarbon chain which may optionally contain a group NR13 which chain is optionally substituted by 1, 2, 3 or 4 groups selected from oxo and C1-6 alkyl groups which groups may optionally be substituted by hydroxy or optionally substituted aryl; R7 represents C1-6 alkyl optionally substituted by one or more halogen atoms, C3-8 cycloalkyl or optionally substituted aryl; R8, R9 and R10 each independently represent H, C1-6 alkyl, amino, hydroxy, cyano or nitro; R11 represents the side chain of a D- or L-amino acid; R12 represents NR13 R14, OR13 or R13 ; each R13 and each R14 independently represents H, C1-6 alkyl or optionally substituted arylC1-4 alkyl; R15 represents C1-6 alkyl; and their pharmaceutically acceptable derivatives are neuraminidase inhibitors useful in the treatment of viral infections.