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US 2024/0199663 A1Published application
Cyclopolyphosphazenes, Related Methods of Preparation and Methods of Use
OwnerSamuel Attah-Poku, George Mutwiri +4inventors
InventorsSamuel Attah-Poku, George Mutwiri, Sylvia Van Den Hurk, Jan Van Den Hurk, John Klaehn, Volker Gerdts
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Abstract
Disclosed herein are cyclopolyphosphazenes of formula I: methods for the preparation thereof and uses thereof in adjuvant compositions.
Claims62
A compound of formula I:
- a tautomer, stereoisomer, polymorph, hydrate, solvate, or pharmaceutically acceptable salt thereof, wherein:
- each of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13, Z14, Z15, Z16, Z17, Z18, Z19, Z20, Z21, Z22, Z23, Z24, Z25, Z26, Z27, Z28, Z29, and Z30 are independently selected from H or formula (II):
- wherein at least one of Z1-30 is represented by formula II, and each of Z1-30 is identical or non-identical;
- and wherein:
- A, if present, is selected from C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, O, S, and N,
- wherein C1-C7 alkyl, C2-C7 alkenyl, and/or C2-C7 alkynyl are straight or branched and optionally substituted by one or more substituents selected from:
- 1° amino, 2° amino, 3° amino, 4° amino, acetal, acyl halide, acyl, aldehyde, alkoxy, amide, aryl, azide, carbamimidoyl, carboxylic acid, cyano, disulfide, epoxide, ester, ether, hydroxyl, imide, imine, ketone, nitrile, nitro, oxime, peroxide, sulfonic acid, sulphonamidyl, thioester, thioether, thiol, amino fluorenylmethyloxycarbonyl (NH-Fmoc), tert-butyloxycarbonyl (Boc), and amino tert-butyloxycarbonyl (—NH—Boc),
- B is selected from C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, H, O, S, and N,
- wherein C1-C7 alkyl, C2-C7 alkenyl, and/or C2-C7 alkynyl are straight or branched and optionally substituted by one or more substituents selected from:
- 1° amino, 2° amino, 3° amino, 4° amino, acetal, acyl halide, acyl, aldehyde, alkoxy, amide, aryl, azide, carbamimidoyl, carboxylic acid, cyano, disulfide, epoxide, ester, ether, hydroxyl, imide, imine, ketone, nitrile, nitro, oxime, peroxide, sulfonic acid, sulphonamidyl, thioester, thioether, thiol, amino fluorenylmethyloxycarbonyl (NH-Fmoc), tert-butyloxycarbonyl (Boc), and amino tert-butyloxycarbonyl (—NH—Boc),
- R, if present, is selected from H, C1-C45 alkyl, C2-C45 alkenyl, and C2-C45 alkynyl,
- wherein C1-C45 alkyl, C2-C45 alkenyl, and/or C2-C45 alkynyl are straight or branched and optionally substituted by one or more substituents selected from:
- 1° amino, 2° amino, 3° amino, 4° amino, acetal, acyl halide, acyl, aldehyde, alkoxy, amide, aryl, azide, carbamimidoyl, carboxylic acid, cyano, disulfide, epoxide, ester, ether, hydroxyl, imide, imine, ketone, nitrile, nitro, oxime, peroxide, sulfonic acid, sulphonamidyl, thioester, thioether, thiol, amino fluorenylmethyloxycarbonyl (NH-Fmoc), tert-butyloxycarbonyl (Boc), and amino tert-butyloxycarbonyl (—NH—Boc).
10 more elements
A compound having formula 37:
- a tautomer, stereoisomer, polymorph, hydrate, solvate, or pharmaceutically acceptable salt thereof.
A compound having formula 6:
- a tautomer, stereoisomer, polymorph, hydrate, solvate, or pharmaceutically acceptable salt thereof.
A compound of formula 11:
- a tautomer, stereoisomer, polymorph, hydrate, solvate, or pharmaceutically acceptable salt thereof.
A compound of formula 9:
- a tautomer, stereoisomer, polymorph, hydrate, solvate, or pharmaceutically acceptable salt thereof.
A compound of formula 39:
- a tautomer, stereoisomer, a polymorph, hydrate, solvate, or pharmaceutically acceptable salt thereof.
A method of producing a compound of formula X:
- the method comprising:
- providing a reactant of formula VIII:
- performing a substitution reaction with formula IX:
- to the reactant, and a base.
1 more element
A method of producing a compound of formula XI:
- the method comprising:
- providing a reactant of formula X:
- performing a hydrolysis reaction with a hydroxide salt and the reactant.
A method of producing a compound of formula VI:
- the method comprising:
- providing a reactant of formula XI:
- performing a substitution reaction with N-hydroxysuccinimide, N,N′-Diisopropylcarbodiimide (DIPCDI) and the reactant.
A method of producing a compound of formula 5:
- the method comprising:
- providing a reactant of formula 3:
- performing a substitution reaction with formula 4:
- the reactant and a base.
1 more element
A method of producing a compound of formula 6:
- the method comprising:
- providing a reactant of formula 5:
- and
- performing a hydrolysis reaction with sodium hydroxide and the reactant.
1 more element
A method of producing a compound of formula 7:
- the method comprising:
- providing a reactant of formula 6:
- performing a substitution reaction with N-hydroxysuccinimide, N,N′-Diisopropylcarbodiimide (DIPCDI) and the reactant.
A method of producing a compound of formula 37:
- the method comprising:
- providing a first reactant of formula 7:
- performing a substitution reaction with a second reactant of formula 19:
- and
- removing the t-butyl carbamate group with acid.
2 more elements
Dependencies are inferred from the claim text.