US 11,390,641 B2 · 5′S-LNA nucleotides and oligonucleotides

Abstract

The invention relates to a compound of formula (I) wherein R2 and R4 are joined and together form a group, such a —CH2O—. The compound of formula (I) can be used in the manufacture of 5′S-LNA oligonucleotides as antisense drugs.

Claims30

Dependent claims

A compound of formula (I)

wherein
R1 is a phosphate protecting group;
R2 and R4 together form —CH2O—, —CH2NH—, —CH2S—, —CH2N(ORp)—, —CHCH3O—,C(CH3)2O, —CH2C(═CH2)—, —CHCH3C(═CH2)—, —CHCH3S—, —CH2NRp—, —CH2CH2O—, —CH2CH2CH2O—, —CH2OCH2—, —CH(CH2OCH3)O—, —CH(CH2CH3)O— or —CH2OCH2O—;
R3 is dialkylamino;
R5 is a thiohydroxyl protecting group;
each Rp is alkyl;
and
Nu is a nucleobase optionally comprising a protected primary amino group.

5 more elements

A process for the manufacture of a compound of formula (I),

comprising reacting a compound of formula (II)
with P(R3)2OR1 in the presence of an oligonucleotide synthesis activator, wherein
R1 is a phosphate protecting group;
R2 and R4 together form —CH2O—, —CH2NH—, —CH2S—, —CH2N(ORp)—, —CHCH3O—,C(CH3)2O, —CH2C(═CH2)—, —CHCH3C(═CH2)—, —CHCH3S—, —CH2NRp—, —CH2CH2O—, —CH2CH2CH2O—, —CH2OCH2—, —CH(CH2OCH3)O—, —CH(CH2CH3)O— or —CH2OCH2O—;
R3 is dialkylamino;
R5 is a thiohydroxyl protecting group;
Nu is a nucleobase optionally comprising a protected primary amino group;
and each Rp is independently alkyl.

5 more elements

Dependencies are inferred from the claim text.

Facts

Application

16/317,586Filed 24 Jul 2017

Priority

IN 20164102566927 Jul 2016

Published

US 2019/0292213 A126 Sep 2019

Granted

19 Jul 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07H 19/06
Heterocyclic radicals containing only nitrogen atoms as ring hetero atom: pyrimidine radicals
A61K 31/7088
Carbohydrates; Sugars; Derivatives thereof: compounds having three or more nucleosides or nucleotides
C07H 1/00
Processes for the preparation of sugar derivatives
C07H 5/10
To sulfur, selenium or tellurium: to sulfur

Abstract

Claims30

Dependent claims

A compound of formula (I)

wherein
R1 is a phosphate protecting group;
R2 and R4 together form —CH2O—, —CH2NH—, —CH2S—, —CH2N(ORp)—, —CHCH3O—,C(CH3)2O, —CH2C(═CH2)—, —CHCH3C(═CH2)—, —CHCH3S—, —CH2NRp—, —CH2CH2O—, —CH2CH2CH2O—, —CH2OCH2—, —CH(CH2OCH3)O—, —CH(CH2CH3)O— or —CH2OCH2O—;
R3 is dialkylamino;
R5 is a thiohydroxyl protecting group;
each Rp is alkyl;
and
Nu is a nucleobase optionally comprising a protected primary amino group.

5 more elements

A process for the manufacture of a compound of formula (I),

comprising reacting a compound of formula (II)
with P(R3)2OR1 in the presence of an oligonucleotide synthesis activator, wherein
R1 is a phosphate protecting group;
R2 and R4 together form —CH2O—, —CH2NH—, —CH2S—, —CH2N(ORp)—, —CHCH3O—,C(CH3)2O, —CH2C(═CH2)—, —CHCH3C(═CH2)—, —CHCH3S—, —CH2NRp—, —CH2CH2O—, —CH2CH2CH2O—, —CH2OCH2—, —CH(CH2OCH3)O—, —CH(CH2CH3)O— or —CH2OCH2O—;
R3 is dialkylamino;
R5 is a thiohydroxyl protecting group;
Nu is a nucleobase optionally comprising a protected primary amino group;
and each Rp is independently alkyl.

5 more elements

Dependencies are inferred from the claim text.

5′S-LNA nucleotides and oligonucleotides

Life of this patent

Abstract

Claims30

5′S-LNA nucleotides and oligonucleotides

Life of this patent

Abstract

Claims30