IP Library Granted Patent US 11,857,515
Granted Patent B2
US 11,857,515 · App. 17/373,707 · Granted Jan 2, 2024

Branched amino acid surfactants for use in healthcare products

Inventor: Edward Asirvatham (Chatham, NJ)
Assignee: AdvanSix Resins & Chemicals LLC
A61K47/183A61K9/0019A61K9/08A61K9/107A61K31/5377A61K31/55A61K47/186A61K47/20
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Quick Facts
Patent No.
US 11,857,515
App. No.
17/373,707
Granted
Jan 2, 2024
Kind
B2
Abstract

Healthcare formulations, including, inventive surfactants, Active ingredient formulated as solids, liquids, or emulsions. The present disclosure provides formulations of healthcare products, such as: prescription drugs, over the counter drugs; minerals, herbal, and/or vitamin supplements; drugs administered in hospitals, clinics, physician's office, and places of palliative care; vaccines, tissue, organ, and cell transplants and/or grafts and/or infusions; and wound care formulations including topical ointments, lotions, cleaners, wipes, bandages, and dressings. The Active may be included in the formulations as a solute, a solvent, a particle, or an oil immiscible component of the formulation. The Active may be included in tablets, capsules, tinctures, liquids, or emulsions. Inventive healthcare formulations include formulations suitable for administration orally, topically, and/or by injection.

Claims (63)

1. A solid healthcare formulation, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates; and an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate; and

at least one Active ingredient.

2. The formulation of claim 1 , wherein the at least one Active ingredient is selected from the group consisting of: a drug, a protein, a cell, a tissue, a vitamin, a supplement, and a mineral.

3. The formulation of claim 1 , further including one or more excipients selected from the group consisting of: binders, fillers, disintegrants, salts, colorants, sweeteners, and flavorants.

4. The formulation of claim 1 , wherein the formulation is configured as a powder, a tablet, or a capsule.

5. The formulation of claim 1 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6. A liquid formulation for healthcare, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates; and an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

at least one Active ingredient; and

an aqueous component.

7. The formulation of claim 6 , further including a buffer.

8. The formulation of claim 6 , further including one or more of the following: a sweetener, a flavorant, a colorant, and/or a preservative.

9. The formulation of claim 6 , further including a thickener.

10. The formulation of claim 6 , wherein the formulation is one of the following; a drop, a paste, a salve, a lotion, or an ointment.

11. The formulation of claim 6 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

12. An emulsion for healthcare, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates; and an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate; and

at least one Active ingredient;

an aqueous phase; and

a non-aqueous phase.

13. The emulsion of claim 12 , further including a buffer.

14. The emulsion of claim 12 , further including one or more of the following: a sweeter, a flavorant, a colorant, and/or a preservative.

15. The emulsion of claim 12 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2021
From: ASIRVATHAM, EDWARD
To: ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 057103/0782 →
Continuity (2)
Provisional Application 63051190 · Jul 13, 2020
Related Publication 20220016248A1 · Jan 20, 2022