Phosphoramidate and phosphorothioamidate oligomeric compounds
First Claim
Patent Images
1. A compound of the structure:
- ##STR3## wherein;
X0 and each Xm, independently, are O or S;
Y0 and each Ym, independently, are H, or [Q2 ]j --Z2 ;
T0 and each Tm, independently, are [Q1 ]k --Z1, or together Y and T are joined in a nitrogen heterocycle;
Q1, Q2, L0, Lm+1 and each Lm, independently, are C2 -C10 alkyl, C2 -C10 alkenyl, C2 -C10 alkynyl, C4 -C7 carbocylo alkyl or alkenyl, a heterocycle, a polyalkyl glycol, or C7 -C14 aralkyl;
E1 and E2, independently, are H, a hydroxyl protecting group, an activated solid support, a conjugate group, a reporter group, a polyethylene glycol, alkyl, oligonucleotide, peptide nucleic acid, a phosphate, a phosphite, an activated phosphate, or an activated phosphite;
j and k independently are 0 or 1;
m is 1 to about 50;
Z1 and Z2, independently, are H, C1 -C2 alkyl, C2 -C20 alkenyl, C2 -C20 alkynyl, C6 -C14 aryl, C7 -C15 aralkyl, CH═
O, OR1, SR2, NR3 R4, C(═
NH)NR3 R4, CH(NR3 R4), NHC(═
NH)NR3 R4, CH(NH2)C(═
O)OH, C(═
O)NR3 R4, C(═
O)OR5, a metal coordination group, a reporter group, a nitrogen-containing heterocycle, a purine, a pyrimidine, a phosphate group, a polyether group, or a polyethylene glycol group;
R1 is H, alkyl having 1 to about 6 carbon atoms, or a hydroxyl protecting group;
R2 is H, alkyl having 1 to about 6 carbon atoms, or a thiol protecting group;
R3 and R4 are, independently, H, alkyl having 1 to about 6 carbon atoms, or an amine protecting group; and
R5 is H, alkyl having 1 to about 6 carbon atoms, or an acid protecting group.
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Abstract
Compounds are provided having the structure: ##STR1## wherein the L groups are spanner or linker units, the Y and T group are functional groups for interacting with target molecules of interest, the X groups are oxygen or sulfur and the E groups are H, conjugate groups or intermediate groups used during the synthesis of the compounds are prepared using H phosphonate type chemistry wherein the functional groups are added during an oxidization step.
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Citations
21 Claims
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1. A compound of the structure:
- ##STR3## wherein;
X0 and each Xm, independently, are O or S;Y0 and each Ym, independently, are H, or [Q2 ]j --Z2 ; T0 and each Tm, independently, are [Q1 ]k --Z1, or together Y and T are joined in a nitrogen heterocycle; Q1, Q2, L0, Lm+1 and each Lm, independently, are C2 -C10 alkyl, C2 -C10 alkenyl, C2 -C10 alkynyl, C4 -C7 carbocylo alkyl or alkenyl, a heterocycle, a polyalkyl glycol, or C7 -C14 aralkyl; E1 and E2, independently, are H, a hydroxyl protecting group, an activated solid support, a conjugate group, a reporter group, a polyethylene glycol, alkyl, oligonucleotide, peptide nucleic acid, a phosphate, a phosphite, an activated phosphate, or an activated phosphite; j and k independently are 0 or 1; m is 1 to about 50; Z1 and Z2, independently, are H, C1 -C2 alkyl, C2 -C20 alkenyl, C2 -C20 alkynyl, C6 -C14 aryl, C7 -C15 aralkyl, CH═
O, OR1, SR2, NR3 R4, C(═
NH)NR3 R4, CH(NR3 R4), NHC(═
NH)NR3 R4, CH(NH2)C(═
O)OH, C(═
O)NR3 R4, C(═
O)OR5, a metal coordination group, a reporter group, a nitrogen-containing heterocycle, a purine, a pyrimidine, a phosphate group, a polyether group, or a polyethylene glycol group;R1 is H, alkyl having 1 to about 6 carbon atoms, or a hydroxyl protecting group; R2 is H, alkyl having 1 to about 6 carbon atoms, or a thiol protecting group; R3 and R4 are, independently, H, alkyl having 1 to about 6 carbon atoms, or an amine protecting group; and R5 is H, alkyl having 1 to about 6 carbon atoms, or an acid protecting group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20)
- ##STR3## wherein;
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21. A chimeric oligomeric compound having a first region comprising a phosphodiester or phosphorothioate oligonucleotide and a second region having the structure:
- ##STR6## wherein;
X0 and each Xm, independently, are O or S;
Q1, Q2, L0, Lm+1 and each Lm, independently, are C2 -C10 alkyl, C2 -C10 alkenyl, C2 -C10 alkynyl, C4 -C7 carbocylo alkyl or alkenyl, a heterocycle, an ether having 2 to 10 carbon atoms and 1 to 4 oxygen or sulfur atoms, a polyalkyl glycol, or C7 -C14 aralkyl;Y0 and each Ym, independently, are H, or [Q2 ]j --Z2 ; T0 and each Tm, independently, are [Q1 ]k --Z1, or together Y and T are joined in a nitrogen heterocycle; j and k independently are 0 or 1; m is 1 to about 50; Z1 and Z2, independently, are H, C1 -C2 alkyl, C2 -C20 alkenyl, C2 -C20 alkynyl, C6 -C14 aryl, C7 -C15 aralkyl, a halogen, CH═
O, OR1, SR2, NR3 R4, C(═
NH)NR3 R4, CH(NR3 R4), NHC(═
NH)NR3 R4, CH(NH2)C(═
O)OH, C(═
O)NR3 R4, C(═
O)OR5, a metal coordination group, a reporter group, a nitrogen-containing heterocycle, a purine, a pyrimidine, a phosphate group, a polyether group, or a polyethylene glycol group;R1 is H, alkyl having 1 to about 6 carbon atoms, or a hydroxyl protecting group; R2 is H, alkyl having 1 to about 6 carbon atoms, or a thiol protecting group; R3 and R4 are, independently, H, alkyl having 1 to about 6 carbon atoms, or an amine protecting group; R5 is H, alkyl having 1 to about 6 carbon atoms, or an acid protecting group; and where one of E1 and E2 comprises said phosphodiester or phosphorothioate oligonucleotide and the other of said E1 and E2 is H, a hydroxyl protecting group or a conjugate group.
- ##STR6## wherein;
Specification
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Current AssigneeISIS Pharmaceuticals Incorporated (Ionis Pharmaceuticals, Inc.)
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Original AssigneeISIS Pharmaceuticals Incorporated (Ionis Pharmaceuticals, Inc.)
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InventorsHebert, Normand, Cook, Phillip D., Acevedo, Oscar
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Primary Examiner(s)Elliott, George C.
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Assistant Examiner(s)LARSON, THOMAS GEORGE
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Application NumberUS08/200,638Time in Patent Office1,203 DaysField of Search536/22.1, 536/23.1, 536/24.1, 536/24.3, 536/24.5, 536/25.3, 514/44US Class Current536/23.1CPC Class CodesA61P 29/00 Non-central analgesic, anti...A61P 31/00 Antiinfectives, i.e. antibi...A61P 43/00 Drugs for specific purposes...C07F 9/091 with hydroxyalkyl compounds...C07H 21/00 Compounds containing two or...
