Derivatives and analogues of 2- deoxy-2.3-didehydro-n-acetyl neuraminic acid and their use as antiviral agents

• Main Authors: VAN PHAN THO, BETTY JIN, MARK ITZSTEIN VON LAURENCE, WEN-YANG WU, BASIL DANYLEC, MALCOLM COLMAN PETER, NOOZHUMURRY VARGHESE JOSEPH
• Format: Patent
• Language: English
• Published: 06.11.1998
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; DERIVATIVES THEREOF; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS; SUGARS

Neuraminic acid derivs. of formula (I) and (Ia) and their salts are new. A = O, S or C in (I) and N or C in (Ia). R1 = COOH, P(O)(OH)2, NO2, SOOH, SO3H, tetrazol, CH2CHO, CHO or CH(CHO)2. R2 = H, OR6, F, Cl, Br, CN, NHR6, SR6 or CH2X. X = NHR6, halo or OR6. R6 = H, 1-4C acyl, linear or cyclic 1-6C alkyl (or a halo substd. analogue), allyl or aryl (opt. substd. by halo, OH, NO2, NH2 or COOH. R3, R3' = independently H, CN, NH(R6)2, N3, SR6, =N-OR6, OR6, guanidino, N(OR6)R6, NR6 -NHR6-N(R6)2, NR6-O, pyrimidino or pyrimidinomethyl. R4 = NHR6, SR6, OR6, COOR6, NO2, C(R6)3, CH2COOR6, CH2NO2 or CH2NHR6. R5 = CH2-YR6, CH(YR6)-CH2-YR6 or CH(YR6)CH(YR6)CH2-YR6. Y = O, S, NH or H, provided that (i) when R3 or R3' is OR6 or H, and A is O or S, then (I) cannot have both (a) R2 as H and (b) R4 as NH-acyl. (ii) R6 is a covalent bond when Y is H. In (Ia), when R3 or R3' is OR6 or H, and A is N, then (Ia) cannot have both (a) R2 as H and (b) R4 as NH-acyl, and (ii) R6 is a covalent bond when Y is H. 14 compounds are specifically claimed including sodium 5-acetamido -4-azido-2,3,4,5-tetradeoxy -D-galacto-non-2-enopyransonate.