Use of film-forming hair care polymers from the group of polyurethanes and pharmaceutical preparations and patches that contain these polymers

• US 20070248658A1
• Filed: 12/22/2006
• Published: 10/25/2007
• Est. Priority Date: 12/23/2005
• Status: Active Grant

• Current Assignee: Epinamics Gmbh
• Original Assignee: Epinamics Gmbh
• Inventors: Franke, Patrick, Bracht, Stefan, Zurdo Schroeder, Ines
• Granted Patent: US 9,393,218 B2
• Time in Patent Office: Days
• US Class Current: 424/449
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/00 Medicinal preparations containing organic active ingredients
• CPC Class Codes: A61K 31/215 of carboxylic acids
• CPC Class Codes: A61K 31/34 having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
• CPC Class Codes: A61K 31/35 having six-membered rings with one oxygen as the only ring hetero atom
• CPC Class Codes: A61K 31/38 having sulfur as a ring hetero atom
• CPC Class Codes: A61K 31/40 having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
• CPC Class Codes: A61K 31/415 1,2-Diazoles
• CPC Class Codes: A61K 31/44 Non condensed pyridines; Hydrogenated derivatives thereof
• CPC Class Codes: A61K 31/445 Non condensed piperidines, e.g. piperocaine
• CPC Class Codes: A61K 31/495 having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazinesA61K31/48 takes precedence ; with three nitrogen atoms A61K31/53
• CPC Class Codes: A61K 31/517 ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
• CPC Class Codes: A61K 31/52 Purines, e.g. adenine
• CPC Class Codes: A61K 31/522 having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
• CPC Class Codes: A61K 31/54 having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
• CPC Class Codes: A61K 31/55 having seven-membered rings, e.g. azelastine, pentylenetetrazole
• CPC Class Codes: A61K 31/70 Carbohydrates; Sugars; Derivatives thereof sorbitol A61K31/047
• CPC Class Codes: A61K 36/00 Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines antigens from pollen A61K39/36
• CPC Class Codes: A61K 36/28 Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
• CPC Class Codes: A61K 36/82 Theaceae (Tea family), e.g. camellia
• CPC Class Codes: A61K 36/886 : Aloeaceae (Aloe family), e.g. aloe vera
• CPC Class Codes: A61K 38/28 : Insulins
• CPC Class Codes: A61K 38/29 : Parathyroid hormone, i.e. parathormone; Parathyroid hormone-related peptides
• CPC Class Codes: A61K 8/0208 : Tissues; Wipes; Patches
• CPC Class Codes: A61K 8/87 : Polyurethanes
• CPC Class Codes: A61K 9/7015 : Drug-containing film-forming compositions, e.g. spray-on
• CPC Class Codes: A61K 9/7069 : obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
• CPC Class Codes: A61Q 19/00 : Preparations for care of the skin

Abstract

The subject of this application is the use of film-forming polyurethanes that are used in hair care agents or mixtures of these polyurethanes with other polymers in pharmaceutical preparations for dermal or transdermal administration of active ingredients, as well as patches and pharmaceutical preparations that contain these hair care polyurethanes.

Claims

1. Use of a film-forming polyurethane that is used in hair care agents, a mixture of these polyurethanes with respect to one another or with other polymers or copolymers of urethanes and other monomers in pharmaceutical preparations for dermal or transdermal administration of active ingredients.

2. Use according to claim 1, characterized in that film-forming mixtures or copolymers that are used in hair care agents are mixtures or copolymers of polyurethanes and acrylates.

3. Use according to claim 1, wherein the film-forming polyurethanes that are used in hair care agents are selected from the group:

Polyurethane-1,

Polyurethane-14 and AMP-acrylate copolymers,

Polyurethane-2,

Polyurethane-4,

Polypropylene glycol-17/isophorone diisocyanate/dimethyl propionic acid copolymer,

Polyvinylpyrrolidone/polycarbamyl/polyglycol ester

Polyvinylpyrrolidone/dimethylaminoethylmethacrylate/polycarbamyl/polyglycol ester

Polyvinylpyrrolidone/dimethiconylacrylate/polycarbamyl/polyglycol ester

4. Use according to claim 1, wherein the film-forming polyurethane that is used in the hair care agents is an optionally neutralized, completely reacted carboxylated linear polyurethane, comprising the reaction product that consists of

(1) one or more 2,2-hydroxymethyl-substituted carboxylic acid(s), produced by the formula I, in which R means hydrogen or C₁-C₂₀-alkyl, present in an amount by weight that is sufficient to produce 0.35-2.25 milliequivalents of carboxyl functionality per gram of polyurethane,

(2) 10-90% by weight, relative to the weight of polyurethane, of one or more organic compound(s), which in each case do not have more than two active hydrogen atoms, and

(3) one or more organic diisocyanate(s), present in an amount that is sufficient to react with the active hydrogen atoms of the 2,2-hydroxymethyl-substituted carboxylic acid and the organic compounds, with the exception of hydrogen, to form the carboxylate of the 2,2-hydroxymethyl-substituted carboxylic acid.

5. Use according to claim 4, wherein the film-forming polyurethane that is used in hair care agents is a polyurethane-14-AMP-acrylate copolymer.

6. Use according to claim 5, wherein the film-forming polyurethane that is used in hair care agents is the polyurethane-14-AMP-acrylate-copolymer DynamX®

.

7. Use according to one of claims 1 to 6, wherein the polymer concentration in the solution is 0.01-40%, preferably 5-30%.

8. Liquid pharmaceutical preparation that, in addition to one or more of the hair care polyurethanes mentioned in claims 1 to 5, contains:

0.01-30% (w/w) of one or more active ingredients,

0.01-99.98% (w/w) of one or more solvents,

Optionally 0.01-20% (w/w) of one or more softeners,

Optionally 0.01-10% (w/w) of one or more moisturizers,

Optionally 0.01-10% (w/w) of one or more emulsifiers and/or

Optionally 0.01-15% (w/w) of one or more permeation enhancers.

9. Liquid pharmaceutical preparation according to claim 8 in the form of a solution, emulsion or suspension.

10. Liquid pharmaceutical preparation according to claim 8 or 9 for transdermal administration of an active ingredient.

11. Liquid pharmaceutical preparation according to claim 10 that contains one or more active ingredients that are selected from the group of:

The androgens testosterone and its esters (such as, for example, testosterone dipropionate), 7-methyl-1-fluoro-19-nortestosterone or 7-methyl-19-nortestosterone

The estrogens ethinyl estradiol, mestranol, quinestranol, estradiol, estrone, estrane, estriol, estetrol and conjugated equine estrogens,

The gestagens progesterone, hydroprogesterone caproate, levonorgestrel, norgestimate, norethisterone, drospirenone, dydrogesterone, norelgestromin, levonorgestrel, dienogest, danazol, lynestrenol, etonogestrel, medrogestone, nestorone and cyproterone acetate

The m-cholinoceptor antagonists scopolamine, trospium chloride, tiotropium and homatropine

The prostaglandins dinoprost, misoprostol, suiprostone, and gemeprost;

As well as Finasteride, raloxifene, nicotine, oxytocin, nitroglycerin, fentanyl, naloxone, bupropion, clonidine, propranolol, metoprolol, diltiazem, nicardipine, captopril, isosorbide dinitrate, dimethyl isosorbide, talinolol, lidocaine, propipocaine, diazepam, midazolam, methyl phenidate, parathormone, rotigotine, insulin, heparin, oxybutynin, sulfaguanidine and/or zidovudine,

including their chiral forms and pharmaceutically acceptable salts.

12. Liquid pharmaceutical preparation according to claim 8 or 9 for dermal administration of an active ingredient.

13. Liquid pharmaceutical preparation according to claim 12 that contains one or more active ingredients that are selected from the group of:

The oligomers of catechins that are included in the tanning materials, oligomers of gallotannins with flavan derivatives, phenocarboxylic acids, gallic acid and esterified sugars of its derivatives

The antiseptic agents chlorhexidine, triclosan and ethacridine

The antibiotics fusidic acid, erythromycin, roxithromycin, clarithromycin, spiramycin, minocycline, clindamycin, neomycin B, kanamycin, gentamycin, amikacin, tobramycin, netilmicin metronidazole, nimorazole, tinidazole polymyxin B, colistin, tyrothricin, bacitracin, mupirocin and cephalexin

The antifungal agents ketoconazole, itraconazole, amphotericin B, griseofulvin, fluconazole, amorolfine, flucytosine, terbinafine, naftifine, ciclopirox, natamycin, nystatin, undecenoic acid and isoconazole

The topical corticosteroids methylprednisolone aceponate, clobetasol propionate, mometasone fuorate, hydrocortisone, betamethasone-17-benzoate, prednicarbate, diflucortolone valerate, triamcinilone acetonide, amcinonide, desoxymethasone, fluocortolone and fluticasone

The topical immunomodulators (macrolides) tacrolimus and pimecrolimus

The antihistamines azelastine, fexofenadine, levocabastine, loratadine, mizolastine, clemastine, bamipine, cetirizine, dimetidine, ketotifen, and emedastine

The immunosuppressive agents cyclosporin, azathioprine and mycophenolate mofetil

The anthralins cignolin and dithranol

The vitamin D3 analogs calcipotriol and tacalcitol

The topical retinoids tretinoin, isotretinoin, acitretin, adapalene and tazarotene

The cytostatic agents methotrexate, 5-fluorouracil, 5-hydroxytamoxifen, zinc-pyrithione and fludarabin

The UV-protective stilbene derivatives

The plant extracts green tea extract, Centella asiatica extract, willow bark extract, birch extract, tea tree oil, olive leaf extract, aloe vera extract, marigold extract, passion blossom extract, witch hazel extract, chamomile extract, bearberry leaf extract and licorice root extract, for example as 18β

-glycyrrhetic acid (Zn combination) or mixtures thereof, as well as

Urea, lactic acid, fumaric acid ester, azelaic acid, hydroquinone, benzoyl peroxide, benzyl benzoate, ketoprofen, ibuprofen, salicylate, naproxen, diclofenac-Na and salts, ketorolac, indomethacin, piroxicam, nicotinamide, dipropyl phthalate, aminopyrine, flufenamic acid, ketotifen, polidocanol, oligonucleotides, si-RNA and ribozymes, RNA decoy nucleotides, aciclovir, penciclovir, idoxuridine, trifluridine, vidarabine, tromantadine, 5-aminolä

vulinic acid, lidocaine, procaine and cinchocaine,

including their chiral forms and pharmaceutically acceptable salts.

14. Liquid pharmaceutical preparation according to one of claims 8 to 13, wherein the solvent is compatible with the skin and is volatile.

15. Liquid pharmaceutical preparation according to claim 14 that contains one or more solvents that are selected from the group:

Ethanol,

Isopropanol,

Ethyl acetate,

Volatile silicones,

Acetone, or

Water.

16. Liquid pharmaceutical preparation according to claim 14 or 15, whereby the solvent is an aqueous solvent mixture whose proportion of water is below 50% (w/w).

17. Liquid pharmaceutical preparation according to one of claims 8 to 13 that contains one or more softeners that are selected from the group:

Triethyl citrate,

Tributyl citrate,

Acetyl triethyl citrate,

Acetyl tributyl citrate,

Triacetin,

Dibutyl phthalate,

Dibutyl sebacate,

Diethyl phthalate,

Propylene glycol,

Polyethylene glycol,

Glycerol or

Castor oil.

18. Liquid pharmaceutical preparation according to one of claims 8 to 13 that contains one or more moisturizers that are selected from the group:

Glycerol,

Sorbitol,

Propylene glycol,

Polyethylene glycol or

Polyvinyl pyrrolidone.

19. Liquid pharmaceutical preparation according to one of claims 8 to 13 that contains one or more emulsifiers that are selected from the group:

Na-Lauryl sulfate,

Na-Cetyl stearyl sulfate,

Glycerol fatty acid ester,

Lecithin,

Fatty alcohols,

Cholesterol,

Sorbitan fatty acid ester,

Polyoxyethylene fatty acid ester,

Polyoxyethylene fatty acid glycerides or

Polyoxyethylene fatty alcohol ether.

20. Liquid pharmaceutical preparation according to one of claims 8 to 13 that contains one or more permeation enhancers selected from the group:

Laurocaprams,

Sulfoxides,

Terpenes or ethereal oil,

Oleic acid,

Oleyl alcohol,

Lauryl acid,

Propylene glycol,

Propylene carbonate,

N-Methyl-pyrrolidone or

Isopropyl myristate.

21. Pharmaceutical preparation according to claim 20 that contains one or more permeation enhancers selected from the group:

Oleic acid,

R-(+)-Limonene,

Isopropyl myristate, in particular mono-isopropyl myristate,

Combination of oleic acid with propylene glycol, preferably in a 1;

1 ratio, or

R-(+)-Limonene with propylene glycol, preferably in a 1;

1 ratio, or

Isopropyl myristate with propylene glycol.

22. Liquid pharmaceutical preparation according to one of claims 8 to 21, wherein the latter can be sprayed and optionally in addition contains a propellant.

23. Applicator that contains a liquid pharmaceutical preparation according to one of claims 8 to 22, in particular in the form of a roller, a pump sprayer, a sprayer, a tube, a brush bottle or a pipette bottle.

24. Flexible, readily adhesive, non-sticky, cosmetically inconspicuous patches for dermal or transdermal administration of an active ingredient that can be obtained by applying a pharmaceutical preparation according to one of claims 7 to 21 on the skin and subsequent evaporation of the solvent.

25. Patch according to claim 24, wherein the water vapor permeability is above 0.05 g*cm⁻

2*24 h<sup>−

1</sup>.

26. Patch according to claim 24 that contains the hair care polymer DynamX®

.