Cyclodextrin dimers and their uses thereof as chemical scavengers

Patent metadata

Field	Value
Publication number	US-12565575-B2
Application number	US-202017641294-A
Country	US
Kind code	B2
Filing date	Sep 9, 2020
Priority date	Sep 11, 2019
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

This invention concerns a compound having the following formula (1):wherein either R1 is a —Y-Nu group and R2 is H, or R1 is H and R2 is a —Y-Nu group and H, wherein Y is, inter alia, —O—(CH2)m—, and m is 1, 2, or 3.

First claim

The invention claimed is:

1 . A compound having the following formula (I):

wherein
either R 1 is a group of the formula —Y-Nu and R 2 is H;
or R 1 is H and R 2 is a group of the formula —Y-Nu;
Y is a linker selected from the group consisting of the following groups:
—O—(CH 2 ) m —, wherein m is 1, 2, or 3;

—(CH 2 ) p —NH—C(═O)—(CH 2 ) q —, wherein p is 0 or 1, and q is 0, 1, or 2;
—CONH—(CH 2 ) r —, wherein r is 1, 2, or 3;
—O—(CH 2 ) s —C≡C—(CH 2 ) t —, wherein s is 1, 2, 3, 4, 5, or 6, and t is 0, 1, 2, or 3;

Nu is selected from the following formulas: formula (II)

wherein
either R is COOH, and X is C—I═O, or formula (I-a):

or R is CH═N—OH, and X is N or N + —(C 1 -C 6 )alkyl,
or R is CO—NH—OH, and X is N.

2 . The compound according to claim 1 , wherein Y is the linker having the formula —O—(CH 2 ) m —, wherein m is 1, 2, or 3, or Y is the linker having the formula —(CH 2 ) p —NH—C(═O)—(CH 2 ) q —, wherein p is 0 or 1, and q is 0, 1, or 2.

3 . The compound according to claim 1 , wherein Nu has the formula (II) according to claim 1 , wherein either R is COOH and X is C—I═O, or R is CO—NH—OH and X is N.

4 . The compound according to claim 1 , wherein R 1 is H and R 2 is —Y-Nu, wherein Y is the linker having the formula —O—(CH 2 ) m —, and wherein m is 1, 2, or 3.

5 . The compound according to claim 1 , wherein R 1 is —Y-Nu, wherein Y is the linker having the formula —O—(CH 2 ) m —, wherein m is 1, 2, or 3, or a linker having the formula —(CH 2 ) p —NH—C(═O)—(CH 2 ) q —, wherein p is 0 or 1, q is 0, 1, or 2, and R 2 is H.

6 . The compound according to claim 1 , wherein —Y-Nu has any of the following formulae (III), (IV) (V), or (VI):

7 . The compound according to claim 6 , wherein R 1 is H, and R 2 has any of the formulae (III), (IV), or (V).

8 . The compound according to claim 6 , wherein R 1 has any of the formulae (III), (IV), or (V), and R 2 is H.

9 . A method for preparing a compound having formula (I) according to claim 1 , wherein the method comprises a step of reacting β-cyclodextrin with a reagent having the following formula (VII):

wherein
either R 4 is H and R 3 is selected from the group consisting of —O—CH 2 —CH═CH 2 , —CH 2 —N 3 , and COOR 5 , wherein R 5 is a (C 1 -C 6 )alkyl, trityl, or benzyl group; or
R 4 is H and R 3 is H;

to obtain a compound having the following formula (VIII):

10 . A compound having one of the formulae (X):

11 . A method for decontaminating surfaces of objects, skin, or mucous membranes contaminated by organophosphate neurotoxic agents, comprising applying the compound of formula (I) according to claim 1 as a chemical scavenger onto the surfaces of the objects, the skin, or the mucous membranes.

12 . A method for reducing the inhibition of acetylcholinesterase activity by organophosphate neurotoxic agents, comprising contacting the organophosphate neurotoxic agents with the compound of formula (I) according to claim 1 .

Assignees

• Centre Nat Rech Scient
• Institut Nat Des Sciences Appliquees De Rouen Normandie
• Univ Rouen Normandie
• Etat Francais Represente Par Le Delegue General Pour Larmement

Inventors

• Estour François
• Bosco Michaël

Classifications

• C11D3/222

  Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin · CPC title

• C08L5/16 Primary

  Cyclodextrin; Derivatives thereof · CPC title

• C08B37/0012 Primary

  Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof · CPC title