Patent ID: 6335434
Filing Date: 2002-01-01
Classification: C07D,C07H

Abstract:
a compound having formula XVIA, XVIB, XVIC or XVID: wherein:W14 has the formula: wherein:X4 is â€”CH(X4â€²) or a group of formula: X4â€² is the side chain of a naturally-occuning amino acid or analog thereof, or a protected side chain of a naturally-occurring amino acid or analog thereof; t is 1 or 2; X5 is â€”N(X6â€²)C(O)â€”, â€”C(O)NHâ€”, â€”NHC(O)â€”, â€”OC(O)NHâ€”, â€”C(S)NHâ€”, â€”SC(S)NHâ€”, â€”SC(O)NHâ€”, â€”OC(S)NHâ€”, â€”C(O)Oâ€”, â€”C(O)(CH2)nâ€” or a bond; n is an integer from 1 to 50; each X6, X6â€² and X9 is, independently, a bond, hydrogen or a hydrocarbyl group selected from C1-C10 alkyl, C2-C10 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C6-C14 aralkyl, C3-C14 cycloalkyl, C5-C14 fused cycloalkyl, C4-C14 heterocycle, C4-C14 heterocyclylalkyl, C4-C14 heteroaryl and C4-C14 heteroarylalkyl; wherein said hydrocarbyl group is substituted with at least two hydroxyl groups, and is optionally substituted with oxo, acyl, alkoxy, alkoxycarbonyl, alkyl, alkenyl, alkynyl, amino, amido, azido, aryl, heteroaryl, carboxylic acid, cyano, guanidino, halo, haloalkyl, haloalkoxy, hydrazino, ODMT, alkylsulfonyl, nitro, sulfide, disulfide, sulfone, sulfonate, sulfonamide, thiol, and thioalkoxy; provided that each X6 and X9 is not hydrogen and X6â€² is not a bond; R1 is hydrogen or a hydroxyl protecting group; R4 is a hydroxyl group or a protected hydroxyl group; each R5â€² and R40 is, independently, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C20 alkynyl, C6-C14 aryl or an amino-protecting group R5â€³ is hydrogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C6-C14 aralkyl, C3-C14 cycloalkyl, formyl, aminoalkyl or hydroxymethyl; R6 is hydrogen or an amino protecting group; R20 is hydrogen or a group of formula: R2 is â€”N(R7)2, or a heterocycloalkyl or heterocycloalkenyl ring containing from 4 to 7 atoms, and having up to 3 heteroatoms selected from nitrogen, sulfur, and oxygen; R7 is straight or branched chain alkyl having from 1 to 10 carbons; R3 is a phosphorus protecting group; R21 is hydrogen, hydroxyl, fluoro or a group of formula Zâ€”R22â€”(R23)v; Z is O, S, NH or Nâ€”R22â€”(R23)v; R22 is C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl; R23 is hydrogen, amino, halogen, hydroxyl, thiol, keto, carboxyl, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aryl, S-aryl, NH-aryl, O-aralkyl, S-aralkyl, NH-aralkyl, amino, N-phthalimido, imidazole, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, aryl, heterocycle, carbocycle, intercalator, reporter molecule, conjugate, polyamine, polyamide, polyalkylene glycol, or a polyether; or R21 has one of the formulas: wherein:y1 is 0 or 1; each y2 is, independently, 0 to 10; y3 is 1 to 10; E is N(R41)(R42) or N&boxH;C(R41)(R42); each R41 and each R42 is independently H, C1-C10 alkyl, a nitogen protecting group, or R41 and R42 taken together form a nitrogen protecting group; or R41 and R42 taken together with the N or C atom to which they are attached form a ring structure that can include at least one heterotom selected from N and O; B is a nucleobase; M is an optionally protected internucleoside linkage; q is from zero to about 50; and v is from zero to about 10; provided that when said compound has formula XVIC, at least one R21 is a group other than hydrogen, and when said compound has formula XVIC or XVID, q is at least 1.