US 12,358,868 B2 · Chemical derivatives and methods for synthesizing and compounding chemical derivatives related to capsaicin palmitate and capsaicin prodrugs

Abstract

Capsaicin compositions and methods for enhancing hydrophobicity of a molecule useful for pharmaceutical applications, including: (1) a prodrug using a linker such as a carbamate between capsaicin with other structures in order to optimize kinetic control of capsaicin cleavage; (2) a prodrug using a linker such as an unsaturated carboxylic ester between capsaicin with other structures in order to optimize kinetic control of capsaicin cleavage; (3) esters of long-chain fatty acids and capsaicin where hydroxyl groups provide handles for attachment of additional capsaicin molecules; and (4) the use of carboxylic acid diesters to increase overall hydrophobicity of two or more covalently-linked capsaicin molecules. Formulations of palmitated esters of capsaicin are also described, which are designed to enhance hydrophobicity of a molecule useful for pharmaceutical applications, for example to provide compounded mixtures designed to optimize analgesic efficacy.

Claims15

Dependent claims

A prodrug of formula (I), (II) or (III):

wherein:
Cpsn represents a capsaicinoid which is joined at a free phenolic hydroxyl group via an ester-containing linkage of formula (I), (II) or (III);
R in formula (I), (II) and (III) is a C1-20 branched, cyclized, saturated or unsaturated hydrocarbon, a molecule with analgesic properties, or a molecule with pharmacological properties;
and
the unsaturated hydrocarbon moiety in formula (I) is a non-cyclic moiety having two carbon atoms, or
the unsaturated hydrocarbon moiety in formula (I) is a benzene moiety that is optionally substituted with up to four substituents selected from the group consisting of a straight, branched or cyclic C1-6 hydrocarbon, a halogen, a hydroxyl, an alkoxyl, a nitrogen-containing substituent, and any combination thereof, such that two adjacent substituents may be joined to form a fused heterocyclic ring;
the saturated hydrocarbon moiety in formula (II) is a branched or cyclic C1-C20 hydrocarbon moiety;
and
n is 6 to 20.

6 more elements

Dependencies are inferred from the claim text.

Facts

Application

18/454,685Filed 23 Aug 2023 · division

Priority

19 Aug 2019

Published

US 2023/0406816 A121 Dec 2023

Granted

15 Jul 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07C 271/40
Esters of carbamic acids: having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
A61K 31/12
Medicinal preparations containing organic active ingredients: ketones
A61K 31/165
Amides, e.g. hydroxamic acids: having aromatic rings, e.g. colchicine, atenolol, progabide
A61K 31/455
Non condensed pyridines; Hydrogenated derivatives thereof: nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides

Family

Application62/889,002Us provisional application · filed 19 Aug 2019

PCT/US2020/046861Parent of this continuation · filed 18 Aug 2020

Application17/673,381Parent of this division · filed 16 Feb 2022

US 2023/0406816 A1Pre-grant publication · published 21 Dec 2023

US 11,773,055 B2Parent of this division

Application17/673,381Parent of this continuation

US 2022/0168259 A1Published application

US 12,358,868 B2This patent

From the US filing history. Foreign family members aren’t listed.

Chemical derivatives and methods for synthesizing and compounding chemical derivatives related to capsaicin palmitate and capsaicin prodrugs

Life of this patent

Chemical derivatives and methods for synthesizing and compounding chemical derivatives related to capsaicin palmitate and capsaicin prodrugs

Life of this patent

Abstract

Claims15