Cyclodextrins preferentially substituted on their primary face by acid or amine functions

• US 6,524,595 B1
• Filed: 07/11/2000
• Issued: 02/25/2003
• Est. Priority Date: 05/12/2000
• Status: Expired due to Term

• Current Assignee: BASF BEAUTY Care Solutions France S.A.S. (BASF SE)
• Original Assignee: Coletica Company
• Inventors: Perrier, Eric, Terry, Nicolas, Rival, Delphine, Coleman, Anthony William
• Primary Examiner(s): Padmanabhan, Sreeni
• Assistant Examiner(s): Willis, Michael A.
• Application Number:
  US09/613,773
• Time in Patent Office: 959 Days
• Field of Search: 424/401, 424/499, 424/184.1, 514/58, 536/18.7
• US Class Current: 424/401
• CPC Class Codes: A61K 2800/413 Nanosized, i.e. having sizes below 100 nm
• CPC Class Codes: A61K 47/40 Cyclodextrins; Derivatives thereof
• CPC Class Codes: A61K 8/738 Cyclodextrins
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/5161 Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61Q 1/06 Lipsticks
• CPC Class Codes: A61Q 1/10 for eyes, e.g. eyeliner, mascara
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C08B 37/0012 Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof

Abstract

Non-hydroxyalkylated cyclodextrins are disclosed wherein at least one primary alcohol function (CH₂OH) is substituted, the —OH portion being replaced by a substituent with formula —O—CO—R or —NR₁R₂, where:

R, R₁ and R₂ independently represent a linear or cyclic, saturated or unsaturated, hydroxylated or non-hydroxylated alkyl group containing 1 to 30 carbon atoms, preferably 1 to 22 carbon atoms, more preferably a fatty chain containing 2 to 22 carbon atoms. These cyclodextrins are used as vectors for at least one active ingredient, in particular to encourage tissue penetration, in a cosmetic application, or for the production of pharmaceutical compositions, in particular dermopharmaceuticals.

Claims

1. A method of cosmetic care comprising topically delivering on skin zones to which said cosmetic care is sought at least one substituted cyclodextrin in the form of at least one nanoparticle or at least one micelle having the following chemical formula:

2. The method of claim 1, wherein R₁ and R₂ independently represent a linear or cyclic, saturated or unsaturated, hydroxylated or non-hydroxylated hydrocarbon radical containing 1 to 22 carbon atoms.

3. The method of claim 1, wherein R₁ and R₂ independently represent a fatty chain of 2 to 22 carbon atoms.

4. The method of claim 1, wherein when X represents NR₁R₂, 1% to 100% of the primary cyclodextrin hydroxyl groups are substituted by the amino group NR₁R₂.

5. The method of claim 1, wherein R represents a linear or cyclic, saturated or unsaturated, hydroxylated or non-hydroxylated hydrocarbon radical containing 1 to 22 carbon atoms.

6. The method of claim 1, wherein R represents a fatty chain that contains 2 to 22 carbon atoms.

7. The method of claim 1, wherein when X represents —

O—

COR, 1 to 100% of the primary hydroxyl groups of the cyclodextrins are substituted by the ester group —

O—

COR.

8. The method of claim 1, wherein the substituted cyclodextrin is in the form of nanoparticles.

9. The method of claim 1, wherein the substituted cyclodextrin is in the form of micelles.

10. The method of claim 1, wherein the substituted cyclodextrin comprises a cavity containing an active ingredient that is cosmetically acceptable, wherein the active ingredient is encapsulated therein, is covalently bonded therewith, or a combination thereof.

11. The method of claim 10, wherein the active ingredient is selected from the group consisting of at least one sugar, a polyol, an oligosaccharide, a polysaccharide, an amino acid, a peptide, a protein, a nucleotide, a nucleoside, an oligonucleotide, an oligonucleoside, a chromophore, a polymer, a sterol, a steroid, a hormone, a flavonoid, a terpene, caffeine, theophylline and their derivatives, nicotine and its derivatives, a vitamin, a vitamin ester, cholesterol, a phospholipid, a glycolipid, a sphingolipid, a ceramid, a triglyceride, a natural polyphenol, a synthetic polyphenol, an essential oil, a flavoring, a fragrance, and a dye, said substance being optionally admixed with a cosmetically acceptable excipient.

12. The method of claim 1, where the cyclodextrin is an α

-cyclodextrin that is substituted by 1 to 18 lauric chains or 1 to 18 hexanoic chains or N,N-dipentylamine, at least one of said substituents being on at least one hydroxyl function of the primary base of the cyclodextrin.

13. The method of claim 1, wherein the cyclodextrin is a β

-cyclodextrin that is substituted by 1 to 21 lauric chains or 1 to 21 hexanoic chains or N,N-dipentylamine, at least one of said substituents being on at least one hydroxyl function of the primary base of the cyclodextrin.

14. The method of claim 1, wherein the cyclodextrin is a γ

-cyclodextrin that is substituted by 1 to 24 lauric chains or 1 to 24 hexanoic chains or N,N-dipentylamine, at least one of said substituents being on at least one hydroxyl function of the primary base of the cyclodextrin.

15. The method of claim 1, wherein the substituted cyclodextrin is further substituted by at least one substituent selected from the group consisting of 4-nitrophenylformate;

ethyloxalate, chloroacetate, succinate, oxalate, sulfonate, and N-(2-aminoethyl)lactonamide.

16. The method of claim 1, wherein the substituted cyclodextrin is heptakis (6-deoxy-6-(N,N-dipentylamino))-β

-cyclodextrin.

17. The method of claim 1, wherein the substituted cyclodextrin is a lauroate β

-cyclodextrin.