Back to results
US 2024/0124488 A1Published application
Aza-cryptophanes, processes for preparation thereof, and their uses
AssigneeUniversite De Caen Normandie
InventorsEmmanuelle DUBOST, Thomas CAILLY, Frédéric FABIS, Clément VIGIER, Aurélie MALZERT-FREON, Anne-Claire GROO
Life of this patent
Estimating the term…
Abstract
The present invention concerns aza-cryptophanes, processes for preparation thereof, and their uses, in particular as in vivo diagnostic tools when complexing a hyperpolarized noble element, or in nanoemulsions.
Claims14
Compound of following formula (I):
- Wherein:
- X1, X2 and X3 are independently selected from —CH2— and —NR—, at least one of X1, X2 and X3 representing —NR—;
- R is chosen from:
- H;
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a LZ group;
- an ad hoc protecting group, in particular a benzyl, p-methoxybenzyl, 2-tetrahydropyranyl, a carbamate, for example Boc, Fmoc, Troc, Cbz, a silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropylsilyl, triethylsilyl, tert-butyldiphenylsilyl, or 2-(trimethylsilyl)ethoxymethyl, or an acyl group, in particular an acetyl;
- Y1, Y2 and Y3 are independently selected from:
- H,
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a O—C1-C6 alkyl;
- a O—C2-C6 alkenyl;
- a O-L′Z′ group;
- OH or a O—P′ group, wherein P′ is an ad hoc protecting group, in particular a benzyl;
- p-methoxybenzyl;
- silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropylsilyl, triethylsilyl, tert-butyldiphenylsilyl;
- 2-(trimethylsilyl)ethoxymethyl;
- allyl;
- methoxymethyl;
- tetrahydropyran or an acyl group, in particular an acetyl;
- Z1, Z2 and Z3 are independently selected from:
- H,
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a O—C1-C6 alkyl;
- a O—C2-C6 alkenyl;
- a O-L″Z″ group;
- OH or a O—P″ group, wherein P″ is an ad hoc protecting group, in particular a benzyl;
- p-methoxybenzyl;
- silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropylsilyl, triethylsilyl, tert-butyldiphenylsilyl;
- 2-(trimethylsilyl)ethoxymethyl;
- allyl;
- methoxymethyl;
- tetrahydropyran or an acyl group, in particular an acetyl;
- n1, n2 and n3 are independently chosen from 0, 1, 2 and 3;
- L, L′ and L″ are independently from each other a linker;
- Z, Z′ and Z″ are independently from each other:
- a terminal reactive function or group, in particular able to form a covalent bond with a peptide, a protein, an antibody or a fragment thereof, a carrier, a solid support, a multivalent scaffold;
- an anchor;
- a dye or a fluorescent residue;
- or
- a peptide, a protein, an antibody or a fragment thereof, a carrier, a solid support, a multivalent scaffold;
- an anchor;
- a dye or a fluorescent residue;
- or a pharmaceutically acceptable salt thereof.
47 more elements
Compound of one of the following formulae:
- wherein:
- X1, X2 and X3 are independently selected from —CH2— and —NR—, at least one of X1, X2 and X3 representing —NR—;
- R is chosen from:
- H;
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- an ad hoc protecting group, in particular a benzyl, p-methoxybenzyl, 2-tetrahydropyranyl, a carbamate, for example Boc, Fmoc, Troc, Cbz, a silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropyl silyl, triethylsilyl, tert-butyldiphenylsilyl, or 2-(trimethylsilyl)ethoxymethyl, or an acyl group, in particular an acetyl;
- Y1, Y2 and Y3 are independently selected from:
- H,
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a O—C1-C6 alkyl;
- a O—C2-C6 alkenyl;
- optionally a O-L′Z′ group;
- a O—P′ group, wherein P′ is an ad hoc protecting group, in particular a benzyl;
- p-methoxybenzyl;
- silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropylsilyl, triethylsilyl, tert-butyldiphenylsilyl;
- 2-(trimethylsilyl)ethoxymethyl;
- allyl;
- methoxymethyl;
- tetrahydropyran or an acyl group, in particular an acetyl;
- Z1, Z2 and Z3 are independently selected from:
- H,
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a O—C1-C6 alkyl;
- a O—C2-C6 alkenyl;
- optionally a O-L″Z″ group;
- a O—P″ group, wherein P″ is an ad hoc protecting group, in particular a benzyl;
- p-methoxybenzyl;
- silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropylsilyl, triethylsily, tert-butyldiphenylsilyl;
- 2-(trimethylsilyl)ethoxymethyl;
- allyl;
- methoxymethyl;
- tetrahydropyran or an acyl group, in particular an acetyl;
- n1, n2 and n3 are independently chosen from 0, 1, 2 and 3.
36 more elements
Nanoemulsion oil-in-water comprising:
- An oil;
- An aqueous phase;
- Optionally, a surfactant;
- Optionally, a co-surfactant and/or a solubilizier;
- and
- A compound of following formula (Ia):
- Wherein:
- X1, X2 and X3 are independently selected from —CH2— and —NR—, at least one of X1, X2 and X3 representing —NR—;
- R is chosen from:
- H;
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- an ad hoc protecting group, in particular a benzyl, p-methoxybenzyl, 2-tetrahydropyranyl, a carbamate, for example Boc, Fmoc, Troc, Cbz, a silyl, in particular tert-butyldimethylsilyl, trimethylsilyl, triisopropylsilyl, triethylsilyl, tert-butyldiphenylsilyl, or 2-(trimethylsilyl)ethoxymethyl, or an acyl group, in particular an acetyl;
- Y1, Y2 and Y3 are independently selected from:
- H,
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a O—C1-C6 alkyl;
- a O—C2-C6 alkenyl;
- OH;
- Z1, Z2 and Z3 are independently selected from:
- H,
- a C1-C6 alkyl;
- a C2-C6 alkenyl;
- a C2-C6 alkynyl;
- a O—C1-C6 alkyl;
- a O—C2-C6 alkenyl;
- OH;
- n1, n2 and n3 are independently chosen from 0, 1, 2 and 3,
- said compound of formula (Ia) being optionally complexed with a hyperpolarized noble element, in particular Xe, more particularly 129Xe.
29 more elements
Dependencies are inferred from the claim text.