# US 10,499,637 B2 · Compositions comprising flavonoid-containing extracts from plants of the genus citrus and/or isolated citrus flavonoids and specific cationic surface active agents, and said composition for use as an agent for treating infestations with head lice

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- Number: US 10,499,637 B2
- Document ID: US10499637B2
- Status: Granted
- Kind: B2
- Application number: 15/361,090
- Filed: 2016-11-25
- Published: 2017-03-16
- Granted: 2019-12-10
- Earliest claimed: 2016-11-25
- Assignees: Meda AB
- Applicants: Meda AB
- Inventors: Heinz Mehlhorn; Guenter Schmahl; Juergen Schmidt; Fathy Abdel Ghaffar; Khaled Al Rasheid; Saleh Quraishi; Ahmad Al-Farhan
- Web page: https://patentgrep.com/patent/US10499637B2

## CPC

- A01N 43/16: with oxygen as the ring hetero atom
- A01N 33/12: Quaternary ammonium compounds
- A61K 8/416: {Quaternary ammonium compounds (A61K8/35 takes precedence)}
- A61K 8/498: {having 6-membered rings or their condensed derivatives, e.g. coumarin}
- A61K 8/9789: Magnoliopsida [dicotyledons]
- A61K 31/352: condensed with carbocyclic rings, e.g. methantheline {(cannabinoids A61K31/658)}
- A61K 31/353: 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61Q 17/02: containing insect repellants
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

A method for treating an infestation of head lice in a patient in need thereof by killing the head lice and preventing a final development and a hatching of larvae from lice eggs. The method includes applying an effective amount of a composition on the hair of the patient. The composition includes about 0.1 to 1 wt.-% of at least one isolated Citrus flavonoid and 2 to 7 wt.-% of at least one cationic surface-active agent. The cationic surface-active agent is selected from a quaternary ammonium salt having one or two linear saturated C8-26 alkyl chain(s), wherein the remaining alkyl residues are C1-6 alkyl groups, and palmitamidopropyltrimonium chloride.

## Claims

### Claim 1

A method for treating an infestation of head lice in a patient in need thereof by killing the head lice and preventing a final development and a hatching of larvae from lice eggs, the method comprising:
applying an effective amount of a composition on the hair of the patient, the composition comprising:
about 0.1 to 1 wt.-% of at least one isolated Citrus flavonoid selected from the group consisting of naringin, naringenin, hesperetin, and hesperidin; and
2 to 7 wt.-% of at least one cationic surface-active agent selected from the group consisting of
palmitamidopropyltrimonium chloride and behentrimonium chloride.

### Claim 2 (depends on 1)

The method as recited in claim 1, wherein the at least one cationic surface active agent is palmitamidopropyltrimonium chloride.

### Claim 3 (depends on 1)

The method as recited in claim 1, wherein the composition is formulated as a shampoo, a spray, an aerosol, a lotion, a hair conditioner, a gel, a mousse, or as a powder.

### Claim 4 (depends on 1)

The method of claim 1, wherein the composition further comprises 92 to 97.9 wt.-% of additives consisting of:
at least one surfactant selected from an ionic surfactant, an anionic amphoteric surfactant, a zwitterionic surfactant, and a cationic surfactant, which are each respectively not the at least one cationic surface-active agent,
at least one of an emulsifier and an emollient,
at least one vehicle,
at least one hair conditioning agent,
at least one preservative, and
optionally, at least one of an insect killing substance, an antioxidant, a pH adjusting agent, and an adjuvant,
wherein, the respective wt.-%'s add to 100 wt.-%.

### Claim 5 (depends on 1)

The method of claim 1, wherein the at least one isolated Citrus flavonoid comprises naringin and the at least one cationic surface active agent comprises palmitamidopropyltrimonium chloride.

### Claim 6 (depends on 1)

The method of claim 1, wherein the at least one isolated Citrus flavonoid comprises naringenin and the at least one cationic surface active agent comprises palmitamidopropyltrimonium chloride.

### Claim 7 (depends on 1)

The method of claim 1, wherein the at least one isolated Citrus flavonoid comprises hesperetin and the at least one cationic surface active agent comprises behentrimonium chloride.

### Claim 8 (depends on 1)

The method of claim 1, wherein the at least one isolated Citrus flavonoid comprises hesperidin and the at least one cationic surface active agent comprises behentrimonium chloride.

### Claim 9

A method for treating an infestation of head lice in a patient in need thereof by killing the head lice and preventing a final development and a hatching of larvae from lice eggs, the method comprising:
applying an effective amount of a composition on the hair of the patient, the composition comprising a Citrus flavonoid extract and 2 to 7 wt.-% of at least one cationic surface-active agent selected from the group consisting of palmitamidopropyltrimonium chloride and behentrimonium chloride,
wherein the Citrus flavonoid extract provides to the composition about 0.1 to 1 wt.-% of at least one isolated Citrus flavonoid selected from the group consisting of naringin, naringenin, hesperetin, and hesperidin.

### Claim 10 (depends on 9)

The method of claim 9, wherein the Citrus flavonoid extract is obtained by a process consisting of:
providing a plant material of the genus Citrus,
mixing the plant material with a first solvent to remove essential oils from the plant material,
separating the first solvent containing the essential oils from the plant material, drying the plant material,
mixing the plant material with a second solvent,
concentrating the plant material and the second solvent so as to obtain a syrup,
adding an acid to the syrup to precipitate at least one Citrus flavonoid,
washing the precipitated at least one Citrus flavonoid, and
drying the washed precipitated at least one Citrus flavonoid to obtain the Citrus flavonoid extract.

### Claim 11 (depends on 9)

The method of claim 9, wherein the composition further comprises 92 to 97.9 wt.-% of additives consisting of:
at least one surfactant selected from an ionic surfactant, an anionic amphoteric surfactant, a zwitterionic surfactant, and a cationic surfactant, which are each respectively not the at least one cationic surface-active agent,
at least one of an emulsifier and an emollient,
at least one vehicle,
at least one hair conditioning agent,
at least one preservative, and
optionally, at least one of an insect killing substance, an antioxidant, a pH adjusting agent, and an adjuvant,
wherein, the respective wt.-%'s add to 100 wt.-%.

### Claim 12 (depends on 9)

The method of claim 9, wherein the at least one cationic surface active agent is palmitamidopropyltrimonium chloride.

### Claim 13 (depends on 9)

The method of claim 9, wherein the composition is formulated as a shampoo, a spray, an aerosol, a lotion, a hair conditioner, a gel, a mousse, or as a powder.

### Claim 14 (depends on 9)

The method of claim 9, wherein the at least one isolated Citrus flavonoid comprises naringin and the at least one cationic surface active agent comprises palmitamidopropyltrimonium chloride.

### Claim 15 (depends on 9)

The method of claim 9, wherein the at least one isolated Citrus flavonoid comprises naringenin and the at least one cationic surface active agent comprises palmitamidopropyltrimonium chloride.

### Claim 16 (depends on 9)

The method of claim 9, wherein the at least one isolated Citrus flavonoid comprises hesperetin and the at least one cationic surface active agent comprises behentrimonium chloride.

### Claim 17 (depends on 9)

The method of claim 9, wherein the at least one isolated Citrus flavonoid comprises hesperidin and the at least one cationic surface active agent comprises behentrimonium chloride.
