Cell internalizing compounds

Patent metadata

Field	Value
Publication number	US-10925968-B2
Application number	US-201916455184-A
Country	US
Kind code	B2
Filing date	Jun 27, 2019
Priority date	Jan 4, 2017
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

Provided herein are cell penetrating compounds having the Formula I:

where, generally, each T is a thiol reactive group (e.g., a phosphorothioate), each L is a linker (e.g., a linear alkyl), and Y is a biologic (e.g., an antibody). Also provided are pharmaceutical compositions including the cell penetrating compounds, and methods of delivering the compound into a cell.

First claim

What is claimed is:

1. A compound having the Formula II:

or a pharmaceutically acceptable salt thereof, wherein:
each R is CH 3 or H;
each L is independently a polyethylene glycol (PEG), a linear alkyl, or a cyclic alkyl;
Y is a protein, an antibody, a peptide, or a nucleic acid; and
n is an integer from 5 to 25.

2. The compound of claim 1 , wherein n is an integer from 12 to 20.

3. The compound of claim 1 , wherein n is 15, 16 or 17.

4. The compound claim 1 , wherein each L is a linear alkyl.

5. The compound of claim 1 , wherein each L is independently a linear (C 2 -C 6 )alkyl, or a cyclic (C 5 -C 6 )alkyl, or —(O—CH 2 —CH 2 ) p —, wherein p is an integer from 1 to 5.

6. The compound of claim 1 , wherein each L is —CH 2 —.

7. The compound of claim 1 , wherein each L is —(O—CH 2 —CH 2 ) p —, wherein p is an integer from 1 to 5.

8. The compound of claim 1 , wherein each R is H, each L is —CH 2 —, n is 15, 16 or 17, and Y is an antibody.

9. The compound of claim 8 , wherein n is 16.

10. The compound of claim 1 , wherein Y is an antibody or antibody fragment.

11. The compound of claim 1 , wherein Y is a peptide.

12. The compound of claim 1 , wherein Y is a protein.

13. The compound of claim 1 , wherein Y is a nucleic acid.

14. A pharmaceutical composition comprising the compound of claim 1 , or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.

15. A method of delivering a therapeutic agent into a cell comprising contacting a cell with a compound of claim 1 or a pharmaceutical composition comprising the compound or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, wherein the compound is internalized into the cell.

16. A pharmaceutical composition comprising the compound of claim 12 , or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.

17. A method of delivering a therapeutic agent into a cell comprising contacting a cell with a compound of claim 1 or a pharmaceutical composition comprising the compound or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, wherein the compound is internalized into the cell.

Assignees

• Sorrento Therapeutics Inc

Inventors

• Fu Yanwen
• Kaufmann Gunnar F
• Lee Heehyoung
• Zhu Tong
• Ji Henry Hongjun

Classifications

• C07K16/18

  against material from animals or humans · CPC title

• C07H21/00

  Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids · CPC title

• C07H19/207

  the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide · CPC title

• C07H19/10

  with the saccharide radical esterified by phosphoric or polyphosphoric acids · CPC title

• A61K39/44

  Antibodies bound to carriers · CPC title