IP Library Granted Patent US 8,541,599
Granted Patent B2
US 8,541,599 · App. 13/414,516 · Granted Sep 24, 2013

Supports for oligomer synthesis

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Quick Facts
Patent No.
US 8,541,599
App. No.
13/414,516
Granted
Sep 24, 2013
Kind
B2
Abstract

Universal linkers, their facile processes of manufacture and methods of using the same are provided.

Claims (49)

1. A compound having the formula:

wherein:

one of Q 1 and Q 2 is a protecting group, a phosphodiester linked nucleoside or a phosphodiester linked oligonucleotide and the other of Q 1 and Q 2 is a linkage attached to a support medium; and

A is hydrogen, a blocking group, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic ether.

2. The compound of claim 1 wherein A is an alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl or substituted alkynyl group.

3. The compound of claim 1 wherein A is methyl.

4. The compound of claim 1 wherein said linkage attached to a support medium has the formula:

—C(═O)—(CH 2 ) n —C(═O)—

wherein n is from about 2 to about 8.

5. The compound of claim 4 wherein n is 2.

6. The compound of claim 1 wherein Q 1 is a protecting group.

7. The compound of claim 1 wherein Q 2 is a protecting group.

8. The compound of claim 1 wherein one of Q 1 and Q 2 is an acid labile hydroxyl protecting group.

9. The compound of claim 8 wherein said acid labile hydroxyl protecting group is 4-methoxytriphenylmethyl, 4,4′-dimethoxytriphenylmethyl, 9-phenylxanthenyl or substituted 9-phenylxanthenyl.

10. The compound of claim 9 wherein said acid labile hydroxyl protecting group is 4,4′-dimethoxytriphenylmethyl.

11. The compound of claim 1 wherein one of Q 1 and Q 2 is a phosphodiester linked nucleoside or oligonucleotide.

12. The compound of claim 1 wherein said support medium is controlled pore glass, oxalyl-controlled pore glass, silica-containing particles, polystyrene, copolymers of polystyrene and divinylbenzene, copolymers of dimethylacrylamide and N,N-bisacryloylethylenediamine, a soluble support medium or PEPS.

13. The compound of claim 12 wherein said support medium is controlled pore glass, polystyrene or copolymers of polystyrene.

14. The compound of claim 13 wherein said support medium is controlled pore glass.

15. The compound of claim 1 wherein said support medium is HL30 Primer solid support, OligoPrep solid support, Nittomar 200 solid support or Nittomar 250 solid support.

16. The compound of claim 1 wherein said linkage is attached to said support medium through an amide linkage.

17. The compound of claim 1 having the formula:

wherein:

one of Q 1 and Q 2 is a protecting group, a phosphodiester linked nucleoside or a phosphodiester linked oligonucleotide and the other of Q 1 and Q 2 is a linkage attached to a support medium; and

A is hydrogen, a blocking group, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aliphatic ether.

18. The compound of claim 17 having the formula:

wherein:

SM is said support material;

A is hydrogen, a blocking group, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aliphatic ether; and

Pg is an acid labile hydroxyl protecting group.

19. The compound of claim 18 wherein:

A is alkyl; and

Pg is 4,4′-dimethoxytriphenylmethyl.

20. The compound of claim 19 wherein A is methyl.

21. The compound of claim 17 having the formula:

wherein:

SM is said support material;

A is hydrogen, a blocking group, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aliphatic ether; and

Pg is an acid labile hydroxyl protecting group.

22. The compound of claim 21 wherein:

A is alkyl; and

Pg is 4,4′-dimethoxytriphenylmethyl.

23. The compound of claim 22 wherein A is methyl.

24. A racemic mixture of compounds of the formula:

wherein:

A is alkyl or an aliphatic ether;

for the first percentage of the mixture Q 3 is a protecting group and Q 4 is SM-C(═O)—(CH 2 ) 2 —C(═O)— and for the second percentage of the mixture Q 3 is SM-C(═O)—(CH 2 ) 2 —C(═O)— and Q 4 is a protecting group and wherein the combined first and second percentages equal essentially 100 percent of the mixture.

25. The racemic mixture of claim 24 wherein A is methyl.

26. The racemic mixture of claim 25 wherein said protecting group is 4,4′-dimethoxytriphenylmethyl.

Assignments (1)
CHANGE OF NAME Recorded Jun 28, 2017
From: ISIS PHARMACEUTICALS, INC.
To: IONIS PHARMACEUTICALS, INC.
Reel/Frame 043029/0302 →