IP Library Granted Patent US 9,550,988
Granted Patent B2
US 9,550,988 · App. 12/445,851 · Granted Jan 24, 2017

Antisense compounds

Inventor: Eric E. Swayze (Encinitas, CA)
Assignee: Ionis Pharmaceuticals, Inc.
C12N15/111C12N15/113C12N2310/11C12N2310/315C12N2310/321C12N2310/3231C12N2310/3341C12N2310/341C12N2310/346C12N2310/351C12N2320/53
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Quick Facts
Patent No.
US 9,550,988
App. No.
12/445,851
Granted
Jan 24, 2017
Kind
B2
Abstract

Provided herein are gapmer oligomeric compounds for reduction of target RNA in vivo comprising different nucleotide modifications within one or both wing regions. Also provided are methods of using such oligomeric compounds, including use in animals. In certain embodiments, such compound have desirable potency and toxicity characteristics.

Claims (42)

1. A gapmer oligonucleotide consisting of 10 to 24 linked nucleosides wherein the gapmer oligonucleotide consists of three regions:

a gap region consisting of 6 to 10 linked deoxynucleosides;

a 5′ wing region positioned at the 5′ end of the gap region and consisting of 1 to 7 linked nucleosides, wherein each nucleoside of the 5′ wing region comprises a modified sugar, and wherein at least one nucleoside of the 5′ wing region is a 2′-O(CH 2 ) 2 OCH 3 modified nucleoside; and

a 3′ wing region positioned at the 3′ end of the gap region and consisting of 1 to 7 linked nucleosides, wherein each nucleoside of the 3′ wing region comprises a modified sugar, and wherein at least one nucleoside of the 3′ wing region is a 4′ to 2′ bicyclic nucleoside; and

wherein a plurality of the internucleoside linkages of the gapmer oligonucleotide are phosphorothioate internucleoside linkages;

or a pharmaceutically acceptable salt thereof.

2. The gapmer oligonucleotide of claim 1 , wherein at least one 4′ to 2′ bicyclic nucleoside is a methyleneoxy (4′-CH 2 -O-2′) bicyclic nucleoside or ethyleneoxy (4′-CH 2 CH 2 -O-2′) bicyclic nucleoside.

3. The gapmer oligonucleotide of claim 1 , wherein at least one 4′ to 2′ bicyclic nucleoside is a methyleneoxy (4′-CH 2 -O-2′) bicyclic nucleoside.

4. The gapmer oligonucleotide of claim 1 , wherein each of the wing regions consists of 1 to 3 linked nucleosides.

5. The gapmer oligonucleotide of claim 1 , wherein at least one nucleoside of the 5′ wing region is a 4′ to 2′ bicyclic nucleoside.

6. The gapmer oligonucleotide of claim 5 , wherein at least one nucleoside of the 3′ wing region is a non-bicyclic 2′ modified nucleoside.

7. The gapmer oligonucleotide of claim 6 , wherein the at least one 4′ to 2′ bicyclic nucleoside of the 5′ wing region is a methyleneoxy (4′-CH 2 -O-2′) bicyclic nucleoside or ethyleneoxy (4′-CH 2 CH 2 -O-2′) bicyclic nucleoside.

8. The gapmer oligonucleotide of claim 6 , wherein the at least one non-bicyclic 2′-modified nucleoside is substituted at the 2′ position with a substituted or unsubstituted —O-alkyl or substituted or unsubstituted —O-(2-acetylamide).

9. The gapmer oligonucleotide of claim 8 , wherein the substitution of the 2′ position is 2′-OCH 3 , 2′-O(CH 2 ) 2 OCH 3 , or 2′-OCH 2 C(O)—NR 1 R 2 , wherein R 1 and R 2 are independently hydrogen or substituted or unsubstituted alkyl or, in the alternative, are taken together to make a heterocyclic moiety.

10. The gapmer oligonucleotide claim 1 , wherein each internucleoside linkage is a phosphorothioate internucleoside linkage.

11. The gapmer oligonucleotide claim 2 , wherein each internucleoside linkage is a phosphorothioate internucleoside linkage.

12. The gapmer oligonucleotide claim 3 , wherein each internucleoside linkage is a phosphorothioate internucleoside linkage.

13. The gapmer oligonucleotide of claim 1 , wherein the gapmer oligonucleotide consists of 15-20 linked nucleosides.

14. The gapmer oligonucleotide of claim 1 , wherein the gapmer oligonucleotide consists of 16-18 linked nucleosides.

15. The gapmer oligonucleotide of claim 1 , wherein the gapmer oligonucleotide consists of 15 linked nucleosides.

16. The gapmer oligonucleotide of claim 1 , wherein the gapmer oligonucleotide consists of 16 linked nucleosides.

17. The gapmer oligonucleotide of claim 1 , wherein the gapmer oligonucleotide consists of 17 linked nucleosides.

18. The gapmer oligonucleotide of claim 1 , wherein the gapmer oligonucleotide consists of 18 linked nucleosides.

19. The gapmer oligonucleotide of claim 1 , wherein the 5′ wing region consists of 1 to 5 linked nucleosides.

20. The gapmer oligonucleotide of claim 1 , wherein the 5′ wing region consists of 1 to 4 linked nucleosides.

21. The gapmer oligonucleotide of claim 1 , wherein the 5′ wing region consists of 1 to 3 linked nucleosides.

22. The gapmer oligonucleotide of claim 1 , wherein the 5′ wing region consists of 4 linked nucleosides.

23. The gapmer oligonucleotide of claim 1 , wherein the 5′ wing region consists of 3 linked nucleosides.

24. The gapmer oligonucleotide of claim 1 , wherein the 3′ wing region consists of 1 to 5 linked nucleosides.

25. The gapmer oligonucleotide of claim 1 , wherein the 3′ wing region consists of 1 to 4 linked nucleosides.

26. The gapmer oligonucleotide of claim 1 , wherein the 3′ wing region consists of 1 to 3 linked nucleosides.

27. The gapmer oligonucleotide of claim 1 , wherein the 3′ wing region consists of 4 linked nucleosides.

28. The gapmer oligonucleotide of claim 1 , wherein the 3′ wing region consists of 3 linked nucleosides.

29. The gapmer oligonucleotide of claim 16 , wherein the 5′ wing region consists of 4 linked nucleosides.

30. The gapmer oligonucleotide of claim 29 , wherein the 3′ wing region consists of 4 linked nucleosides.

31. The gapmer oligonucleotide of claim 17 , wherein the 5′ wing region consists of 4 linked nucleosides.

32. The gapmer oligonucleotide of claim 31 , wherein the 3′ wing region consists of 4 linked nucleosides.

33. The gapmer oligonucleotide of claim 18 , wherein the 5′ wing region consists of 4 linked nucleosides.

34. The gapmer oligonucleotide of claim 33 , wherein the 3′ wing region consists of 4 linked nucleosides.

35. A conjugate comprising the gapmer oligonucleotide of claim 1 and a conjugate group.

36. The conjugate of claim 35 , wherein the conjugate group comprises a linking group.

37. A pharmaceutical composition comprising the gapmer oligonucleotide of claim 1 and a pharmaceutically acceptable diluent or carrier.

Assignments (2)
CHANGE OF NAME Recorded Dec 30, 2015
From: ISIS PHARMACEUTICALS, INC.
To: IONIS PHARMACEUTICALS, INC.
Reel/Frame 037405/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2009
From: SWAYZE, ERIC E.
To: ISIS PHARMACEUTICALS, INC.
Reel/Frame 023090/0288 →
Continuity (2)
Provisional Application 60852894 · Oct 18, 2006
Related Publication 20100197762A1 · Aug 5, 2010