Back to results
US 5,684,148 AGranted
Nucleoside thiophosphoramidites
AssigneeCompetitive Technologies, Inc.
InventorsMarvin H. Caruthers, Wolfgang K. D. Brill, Eric Yau, Michael Ma, John Nielsen
Life of this patent
Estimating the term…
Abstract
The present invention relates to new and useful nucleoside thiophosphoroamidites and polynucleotide phosphorodithioate compounds as well as the processes whereby these compounds may be used for synthesizing new mononucleotides and polynucleotides having phosphorothioate and phosphorodithioate internucleotide linkages.
Claims29
A compound according to the formula:
- ##STR41## wherein B is a nucleoside or deoxynucleoside base;
- wherein A is OH, H, halogen, SH, NH.sub.2, azide, or KR.sub.2 wherein K is oxygen, sulfur, or nitrogen, and R.sub.2 is a blocking group;
- and
- wherein R.sub.1 is a blocking group.
1 more element
A compound according to the formula:
- ##STR44## wherein B is a nucleoside or deoxynucleoside base;
- wherein A is OH, H, halogen, SH, NH.sub.2, azide, or KR.sub.2 wherein K is oxygen, sulfur, or nitrogen and R.sub.2 is a blocking group;
- wherein R.sub.1 is a blocking group;
- and
- wherein R.sub.4 is a blocking group.
2 more elements
A compound according to the formula:
- ##STR47## wherein B is a nucleoside or deoxynucleoside base;
- wherein A is OH, H, halogen, SH, NH.sub.2, azide, or KR.sub.2 wherein K is oxygen, sulfur, or nitrogen and R.sub.2 is a blocking group;
- wherein R.sub.1 is a blocking group;
- and
- wherein R.sub.8 is a heteroatom substituted or unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, aralkenyl, alkynyl, aralkynyl, or cycloalkynyl.
2 more elements
A compound according to the formula:
- ##STR50## wherein B is a nucleoside or deoxynucleoside base;
- wherein A is OH, H, halogen, SH, NH.sub.2, azide, or KR.sub.2 wherein K is oxygen, sulfur, or nitrogen and R.sub.2 is a blocking group;
- wherein R.sub.1 is a blocking group;
- and
- wherein R.sub.9 is a heteroatom substituted or unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, aralkenyl, alkynyl, aralkynyl, or cycloalkynyl group.
2 more elements
A compound according to the formula:
- ##STR53## wherein B is a nucleoside or deoxynucleoside base;
- wherein A is OH, H, halogen, SH, NH.sub.2, azide, or DR.sub.2 wherein D is oxygen, sulfur or nitrogen, and R.sub.2 is a heteroatom blocking group;
- wherein R.sub.1 is a blocking group;
- X is an amino group of the formula NR.sub.6 R.sub.7
- (a) wherein R.sub.6 and R.sub.7 each taken separately is a heteroatom substituted or unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, aralkenyl, alkynyl, aralkynyl or cycloalkynyl,
- (b) when taken together with the nitrogen atom to which they are attached is a heterocyclic containing up to 5 carbon atoms in the cyclic structure which structure may contain up to an additional 5 carbon atoms pendant thereon,
- (c) when taken together with the nitrogen atom to which they are attached is a nitrogen heterocycle including at least one additional heteroatom selected from the group consisting of nitrogen, oxygen and sulfur;
- and
- wherein R.sub.5 is a heteroatom substituted or unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, aralkenyl, alkynyl, aralkynyl, or cycloalkynyl.
6 more elements
A compound according to the formula:
- ##STR56## wherein B is a nucleoside or deoxynucleoside base;
- wherein A is D or DR.sub.2 where D is OH, H, halogen, SH, NH.sub.2 or azide, and DR.sub.2 is oxygen, sulfur or nitrogen as D and R.sub.2 is a heteroatom substituted or unsubstituted blocking group;
- wherein R.sub.1 is a blocking group;
- wherein X is a secondary amino group of the formula NR.sub.6 R.sub.7,
- (a) wherein R.sub.6 and R.sub.7 each taken separately is a heteroatom substituted or unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, aralkenyl, alkynyl, aralkynyl or cycloalkynyl,
- (b) when taken together with the nitrogen atom to which they are attached is a heterocyclic containing up to 5 carbon atoms in the cyclic structure which structure may contain up to an additional 5 carbon atoms pendant thereon,
- (c) when taken together with the nitrogen atom to which they are attached is a nitrogen heterocycle including at least one additional heteroatom selected from the group consisting of nitrogen, oxygen and sulfur;
- wherein M is sulfur;
- and
- wherein R.sub.5 is a heteroatom substituted or unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, aralkenyl, alkynyl, aralkynyl or cycloalkynyl.
7 more elements
Dependencies are inferred from the claim text.