Patent ID: 6271357
Filing Date: 2001-08-07
Classification: A61K,A61P,C07D,C07F,C07H,C08G,C12N,C12Q,C12Y

Abstract:
A method for forming a covalent linkage comprising the steps of(a) providing synthons having structures: ##STR5##(b) contacting said synthons for a time and under reaction conditions effective to form a covalent linkage having formula --CH=N--;wherein:R.sub.N1 and R.sub.N2 are, independently, amine protecting groups, or together form an amine protecting group; andR.sub.A1 and R.sub.A2 are, independently, hydrogen, aryl, a protected carbonyl, or a group having the formula: {N(R.sub.N)--O--A--CH.sub.2 }.sub.r where r is 1-100;each A is, independently, R.sub.S --X(T--L)--R.sub.S ; N--R.sub.N ; C(O); a single bond; or (CH.sub.2).sub.m where m is 1-5;each R.sub.N is, independently, H, an amine protecting group or T--L;each R.sub.S is, independently, a single bond or alkyl having 1 to about 12 carbon atoms;each T is, independently, a single bond, a methylene group or a group having structure II:--[CR.sup.1 R.sup.2 ].sub.n --B--[CR.sub.1 R.sub.2 ].sub.o --[D].sub.p --[N(R.sub.N)].sub.q --IIwhere:D is C(O), C(S), C(Se), C(R.sup.1)(N.sup.3 R.sup.4), CH.sub.2 R.sup.1, CHR.sup.1 R.sup.2, or NR.sup.3 R.sup.4 ;B is a single bond, CH=CH, C.ident.C, O, S or NR.sup.4 ;each R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, alkyl or alkenyl having 1 to about 12 carbon atoms, hydroxy- or alkoxy- or alkylthio-substituted alkyl or alkenyl having 1 to about 12 carbon atoms, hydroxy, alkoxy, alkylthio, amino and halogen;R.sup.3 and R.sup.4, independently, are H, --T--L, alkyl having I to about 10 carbon atoms; alkenyl having 2 to about 10 carbon atoms; alkynyl having 2 to about 10 carbon atoms; aryl having 7 to about 14 carbon atoms; heterocyclic; a reporter molecule; or an RNA cleaving group; orR.sup.3 and R.sup.4, together, are cycloalkyl having 3 to about 10 carbon atoms or cycloalkenyl having 4 to about 10 carbon atoms;n and o, independently, are zero to 5;q is zero or 1;p is zero to about 10;each L is, independently, a nucleosidic base, an amino acid side chain, an aromatic hydrocarbon, a heterocycle moiety containing nitrogen, sulfur, and/or oxygen; a carbohydrate, a drug, a reporter molecule; an RNA cleaving group; andeach X is, independently, N or CH, orX and T, together, form an aromatic moiety, a pentose, a hexose, or a deoxy derivative of a pentose or a hexose.