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WO2001021148B1 - No-liberating topically applicable composition as biological agent, production and utilization thereof as dermatological and/or cosmetic product - Google Patents

No-liberating topically applicable composition as biological agent, production and utilization thereof as dermatological and/or cosmetic product

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Publication number
WO2001021148B1
WO2001021148B1 PCT/EP2000/008067 EP0008067W WO0121148B1 WO 2001021148 B1 WO2001021148 B1 WO 2001021148B1 EP 0008067 W EP0008067 W EP 0008067W WO 0121148 B1 WO0121148 B1 WO 0121148B1
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Prior art keywords
releasing compound
composition
effect
application
derivatives
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PCT/EP2000/008067
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German (de)
French (fr)
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WO2001021148A1 (en
Inventor
Victoria Kolb-Bachofen
Klaus-Dietrich Kroencke
Annegret Kuhn
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KROENCKE KLAUS DIETRICH
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KROENCKE KLAUS DIETRICH
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Priority to EP00958469A priority Critical patent/EP1216019A1/en
Priority to AU69972/00A priority patent/AU6997200A/en
Publication of WO2001021148A1 publication Critical patent/WO2001021148A1/en
Anticipated expiration legal-status Critical
Publication of WO2001021148B1 publication Critical patent/WO2001021148B1/en
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a composition containing at least one NO-liberating compound for use as a topically administered agent which is biologically active at the site of application. Said composition does not contain L-arginine, salts and derivatives thereof, and also NO-polyethylenimine cellulose used in the field of pharmacy and / or cosmetics. Said invention relates to the application of a composition containing at least one pharmacologically compatible NO-liberating compound for therapy and prophylaxis of skin damage produced by electromagnetic radiation having a wavelength between 1mm to 100 nm, preferably 400 nm - 200 nm, or photodermatoses or hyperproliferative dermatoses. Said invention also relates to a method for cosmetic treatment to protect the skin from damage by ultraviolet light, whereby prior to or during irradiation an active amount of a cosmetic composition of the aforementioned type containing at least one NO-liberating compound is applied to the surface of the skin.

Claims

GEÄNDERTE ANSPRÜCHE[beim Internationalen Büro am 3. April 2001 (03.04.01) eingegangen; ursprünglicher Anspruch 1 geändert; alle weiteren Ansprüche unverändert (3 Seiten)] CHANGED CLAIMS [received at the International Bureau on April 3, 2001 (April 3, 2001); original claim 1 amended; all other claims unchanged (3 pages)] 1. Zusammensetzung, enthaltend wenigstens eine NO-freisetzende Verbindung als topisch verabreichbares, am Ort der Applikation wirkendes Mittel mit biologischer Wirkung, wobei als NO-freisetzende Verbindung L-Arginin, seine Salze und Derivate, 7-Nitroindazol sowie NO-Polyethylenimin- cellulose ausgenommen sind.1. Composition containing at least one NO-releasing compound as a topically administrable agent which acts at the point of application and has a biological action, with the exception of L-arginine, its salts and derivatives, 7-nitroindazole and NO-polyethyleneimine cellulose as the NO-releasing compound are. 2. Zusammensetzung, insbesondere nach Anspruch 1 , enthaltend wenigstens eine NO-freisetzende Verbindung zur Verwendung als topisch verabreichbares Mittel mit kosmetischer Wirkung.2. Composition, in particular according to claim 1, containing at least one NO-releasing compound for use as a topically administrable agent with a cosmetic effect. 3. Zusammensetzung nach Anspruch 1 , enthaltend wenigstens eine pharmakologisch verträgliche NO-freisetzende Verbindung zur Verwendung als topisch verabreichbares Mittel mit pharmazeutischer Wirkung.3. Composition according to claim 1, comprising at least one pharmacologically acceptable NO-releasing compound for use as a topically administrable agent with pharmaceutical activity. 4. Zusammensetzung nach Anspruch 2, dadurch gekennzeichnet, daß sie4. Composition according to claim 2, characterized in that it 1 μmol bis 200 mmol, vorzugsweise 5 μmol bis 100 mmol, der NO- freisetzenden Verbindung bezogen auf 100 g der Gesamtzusammensetzung enthält.Contains 1 μmol to 200 mmol, preferably 5 μmol to 100 mmol, of the NO-releasing compound based on 100 g of the total composition. 5. Zusammensetzung nach Anspruch 3, dadurch gekennzeichnet, daß sie 1 μmol bis 200 mmol, vorzugsweise 10 μmol bis 100 mmol der NO- freisetzenden Verbindung, bezogen auf 100 g der Gesamtzusammensetzung enthält.5. Composition according to claim 3, characterized in that it contains 1 μmol to 200 mmol, preferably 10 μmol to 100 mmol, of the NO-releasing compound, based on 100 g of the total composition. 17 17 6. Zusammensetzung nach vorstehenden Ansprüchen, dadurch gekennzeichnet, daß es sich bei der NO-freisetzenden Verbindung um eine unter physiologischen Bedingungen spontan NO-freisetzende, biochemisch oder physikalisch NO-freisetzende Verbindung handelt.6. Composition according to the preceding claims, characterized in that the NO-releasing compound is a spontaneously NO-releasing, biochemically or physically NO-releasing compound under physiological conditions. 7. Zusammensetzung nach vorstehenden Ansprüchen, dadurch gekennzeichnet, daß die NO-freisetzende Verbindung ausgewählt ist aus anorganischen und/oder organischen Verbindungen, wobei die organischen Verbindungen ausgewählt sind aus der Klasse der S-Nitrosothiole sowie der Addukte von Stickstoffmonoxid mit einem Nucleophil (z.B. Diazeniumdiolate).7. Composition according to the preceding claims, characterized in that the NO-releasing compound is selected from inorganic and / or organic compounds, the organic compounds being selected from the class of S-nitrosothiols and the adducts of nitrogen monoxide with a nucleophile (for example diazenium diolates ). 8. Zusammensetzung nach Anspruch 2 oder 5 - 7, dadurch gekennzeichnet, daß sie weiterhin 0,5 Gew.-% bis 20 Gew.-% Lichtschutzmittel für UV- A und oder UV-B, bezogen auf die Gesamtzusammensetzung, enthalten, wobei das Lichtschutzmittel vorzugsweise ausgewählt ist aus der Klasse bestehend aus Benzylidencampferderivaten, Dibenzoylmethanderivaten, Benzotriazolderivaten, Triazinderivaten, p-Aminobenzoesäurederivaten, Zimtesterderivaten, Salicylsäuredehvaten, Anthranilsäurederivaten, Urocaninsäurederivaten, Benzophenonderivaten und/oder Benzimidazolsulfonsäurederivaten.8. Composition according to claim 2 or 5-7, characterized in that they further contain 0.5 wt .-% to 20 wt .-% light stabilizers for UV-A and or UV-B, based on the total composition, wherein the Light stabilizers are preferably selected from the class consisting of benzylidene camphor derivatives, dibenzoylmethane derivatives, benzotriazole derivatives, triazine derivatives, p-aminobenzoic acid derivatives, cinnamon ester derivatives, salicylic acid derivatives, anthranilic acid derivatives, urocanic acid derivatives and benzophenone derivative. 9. Zusammensetzung nach vorstehenden Ansprüchen, dadurch gekennzeichnet, daß sie weiterhin einen Träger enthält, der mindestens eine Fettphase auf Basis mineralischer, pflanzlicher oder tierischer Öle oder Wachse, Fettsäuren, Fettalkohole mit 6 bis 22 Kohlenstoffatomen aufweist.9. Composition according to the preceding claims, characterized in that it further contains a carrier which has at least one fat phase based on mineral, vegetable or animal oils or waxes, fatty acids, fatty alcohols having 6 to 22 carbon atoms. 10. Zusammensetzung nach vorstehenden Ansprüchen, dadurch gekennzeichnet, daß sie in Form einer Salbe, einer Creme, eines Gels, eingebettet in Liposomen, eines Öls, einer Milch, eines festen Stifts oder als Aerosols vorliegen.10. Composition according to the preceding claims, characterized in that they are in the form of an ointment, a cream, a gel, embedded in liposomes, an oil, a milk, a solid stick or as an aerosol. 18 18 11. Verwendung einer Zusammensetzung, enthaltend wenigstens eine pharmakologisch verträgliche NO-freisetzende Verbindung zur Behandlung und Prophylaxe von durch elektromagnetische Strahlen einer Wellenlänge von 1 mm bis 1 nm, vorzugsweise 400 nm - 200 nm, hervorgerufenen Hautschäden und Lichtdermatosen oder hyperproliferativen Dermatosen, wie z.B. Psoriasis vulgäre oder seborrhoische Keratosen.11. Use of a composition containing at least one pharmacologically acceptable NO-releasing compound for the treatment and prophylaxis of skin damage and light dermatoses or hyperproliferative dermatoses, such as e.g. Psoriasis vulgar or seborrheic keratosis. 12. Verwendung nach Anspruch 11 , dadurch gekennzeichnet, daß die durch elektromagnetische Strahlung hervorgerufenen Dermatosen ausgewählt sind aus Combustio, Erythema solare, Lichtdermatosen oder Kollagenosen wie z.B. cutanen oder systemischen Lupus erythematodes.12. Use according to claim 11, characterized in that the dermatoses caused by electromagnetic radiation are selected from combustio, erythema solar, light dermatoses or collagenoses such as e.g. cutaneous or systemic lupus erythematosus. 13. Verwendung einer Zusammensetzung, enthaltend wenigstens eine NO- freisetzende Verbindung als kosmetisches Produkt.13. Use of a composition containing at least one NO-releasing compound as a cosmetic product. 14. Verfahren zur kosmetischen Behandlung zum Schutz der Haut gegen durch ultraviolette Strahlen verursachte Schäden, dadurch gekennzeichnet, daß man vor oder während der Bestrahlung eine wirksame Menge wenigstens einer NO-freisetzenden Verbindung enthaltenden kosmetischen Zusammensetzung gemäß Anspruch 2 oder 5 - 10 mit der Hautoberfläche kontaktiert.14. A method of cosmetic treatment for protecting the skin against damage caused by ultraviolet rays, characterized in that an effective amount of at least one NO-releasing compound-containing cosmetic composition according to claim 2 or 5-10 is contacted with the skin surface before or during the irradiation , 19 IN ARTIKEL 19 (1) GENANNTE ERKLÄRUNG19 DECLARATION REFERRED TO IN ARTICLE 19 (1) Die DE 43 05 881 C1 betrifft gemäß Beschreibungseinleitung ein transdermales therapeutisches System zur systemischen und topischen Verabreichung von Wirkstoffen, welche geeignet sind, die Stickoxid (NO)-Konzentration im menschlichen Organismus zu erhöhen.According to the introduction to the description, DE 43 05 881 C1 relates to a transdermal therapeutic system for the systemic and topical administration of active substances which are suitable for increasing the nitrogen oxide (NO) concentration in the human organism. Hierbei handelt es sich insbesondere um ein Pflaster gemäß Anspruch 1 1 in Verbindung mit dem die Spalten 2 und 3 überbrückenden Absatz, welches zur Behandlung einer Reihe von Krankheiten, wie sie in den Ansprüchen 17 bis 23 definiert sind, verabreicht werden soll, die alle einen Wirkort entfernt von Epidermis und Dermis haben, also nicht wie im Sinne der vorliegenden Erfindung eine lokale kutane Wirkung. Diese wären auch bei einem System zur Durchschleusung durch Epidermis und Dermis nicht sinnvoll, wie es in diesem Stand der Technik gefordert wird. Insofern wird durch diesen Stand der Technik die vorliegende Erfindung, wie beansprucht, weder vorbeschrieben noch nahegelegt.This is in particular a plaster according to claim 1 1 in connection with the paragraph bridging columns 2 and 3, which is to be administered for the treatment of a number of diseases as defined in claims 17 to 23, all of them one Site of action distant from the epidermis and dermis, ie not as in the sense of the present invention a local cutaneous effect. These would not make sense even with a system for the passage through the epidermis and dermis, as is required in this prior art. In this respect, the present invention, as claimed, is neither described nor suggested by this prior art. Der Artikel von Ormerod et al aus dem JOURNAL OF INVESTIGATIVE DERMATOLOGY, Band 1 13, Nr. 3, September 1999, Seite 392ff berichtet über Befunde zu adversen, entzündungsfördernden Wirkungen einer NO-freisetzenden Creme, die nach Applikation einer angesäuerten Ascorbinsäure und Nitrit enthaltenden Formulierung unter Okklusion (gasdichter Verschluss) über 1 bis 2 Tage beobachtet worden (siehe Abschnitt MATERIALS AND METHODS „both Sites were then occluded with adhesive plastic and the procedure repeated every 8 h"). Bei den beobachteten adversen Reaktionen scheint die Okklusion das entscheidende Problem darzustellen. Die gleiche Gruppe hatte nach Anwendung genau dieser Creme ohne Okklusion zur Bekämpfung von Hautinfektionen keinerlei negative Wirkung, außer einer leichten temporären Braunfärbung. Wir verweisen beispielsweise auf : Davidson et al. A topical nitric oxide-generating therapy for cutaneous leishmaniasis, Trans. R. Soc. Trop. Med. Hyg. 94, 319-322 (2000) sowie: Ormerod et al., Molluscum contagiosum effectively treated with a topical acidified nitrite, nitric oxide liberating cream. Br. J. Dermatol. 141 , 1051 -1053 (1999) sowie: Weller et al. A randomized trial of acidified nitrite cream in theThe article by Ormerod et al from the JOURNAL OF INVESTIGATIVE DERMATOLOGY, Volume 1 13, No. 3, September 1999, page 392ff reports on findings on adverse, inflammation-promoting effects of a NO-releasing cream which, after application of a formulation containing acidified ascorbic acid and nitrite observed under occlusion (gastight closure) for 1 to 2 days (see section MATERIALS AND METHODS "both sites were then occluded with adhesive plastic and the procedure repeated every 8 h"). In the observed adverse reactions, occlusion seems to be the decisive problem The same group had no negative effects after application of exactly this cream without occlusion to combat skin infections, except for a slight temporary brown color. For example, we refer to: Davidson et al. A topical nitric oxide-generating therapy for cutaneous leishmaniasis, Trans. R. Soc. Trop. Med. Hyg. 94, 319-322 (2000) and: Orme rod et al., Molluscum contagiosum effectively treated with a topical acidified nitrite, nitric oxide liberating cream. Br. J. Dermatol. 141, 1051-1053 (1999) and: Weller et al. A randomized trial of acidified nitrite cream in the 20 treatment of tinea pedis. J. AmAcad. Dermatol. 38, 559-563 (1998). Insofern ist Gegenstand dieses Standes der Technik primär die Bekämpfung von Infektionen, allerdings nicht der Einsatz einer NO-freisetzenden Verbindung als topisch verabreichbares am Ort der Applikation wirkendes Mittel mit biologischer Wirkung, also einer primär pigmentierungsfördemden Wirkung.20 treatment of tinea pedis. J. AmAcad. Dermatol. 38, 559-563 (1998). In this respect, the subject of this prior art is primarily the control of infections, but not the use of an NO-releasing compound as a topically administrable agent at the site of application with a biological effect, that is to say a pigmentation-promoting effect. Die Publikation von Benrath et al. aus den Neuroscience letters, Band 200, Nr. 1 vom 10. November 1999, Seite 17 - 20 betrifft die Applikation eines NO-Synthase Inhibitors (L- NAME), wie er auf Seite 18, linke Spalte, Zeile 2 - 4 definiert ist, nach einer Breitband-UV- Bestrahlung von Ratten mit einer leichten Vergrößerung des nekrotischen Bereiches korreliert, sowie mit einer Reduktion eines Proliferationssignals (siehe Abstract i.V. mit Figur 2). Weiter wird in der Diskussion vermutet, dass diese nachteilige Wirkung von L-NAME auf eine Hemmung derAngiogenese und der Keratinozytenproliferation zurückzuführen sei (Seite 19, rechte Spalte, 1. vollständiger Absatz). Dazu ist anzumerken, dass von der Applikation eines Inhibitors mit präferentieller Wirkung auf endotheliale NO-Synthese keineswegs automatisch auf die entgegengesetzte Wirkung bei lokaler Applikation von NO-freisetzenden Substanzen geschlossen werden kann, und auch kann dieser Tierversuch nicht automatisch auf eine entsprechende Wirkung auf humaner Kutis übertragen werden. Die Schlussfolgerungen sind rein statistischer, also korrelativer Art und ohne jede Dosis- Wirkbeziehung. Schließlich ist auch noch zu berücksichtigen, dass in dieser Arbeit nur über eine kurative Wirkung, also eine Wundheilung, aber nicht über eine präventive Wirkung, also eine Vermeidung von Sonnenbrand berichtet wird.The publication by Benrath et al. from Neuroscience letters, Volume 200, No. 1 of November 10, 1999, pages 17-20, relates to the application of a NO synthase inhibitor (L-NAME) as defined on page 18, left column, lines 2-4 correlated with a slight enlargement of the necrotic area after broad-band UV radiation of rats, and with a reduction in a proliferation signal (see abstract in conjunction with FIG. 2). The discussion also suggests that this adverse effect of L-NAME is due to inhibition of angiogenesis and keratinocyte proliferation (page 19, right column, 1st full paragraph). It should be noted that the application of an inhibitor with a preferential effect on endothelial NO synthesis can in no way automatically infer the opposite effect when local application of NO-releasing substances occurs, and this animal experiment cannot automatically suggest a corresponding effect on human cuties be transmitted. The conclusions are purely statistical, that is to say correlative, and without any dose-effect relationship. Finally, it should also be taken into account that this work only reports on a curative effect, i.e. wound healing, but not on a preventive effect, i.e. avoidance of sunburn. Insofern legt auch dieses Papier den Gegenstand der vorliegenden Anmeldung wie beansprucht weder vorweg, noch legt sie ihn nahe.In this respect, this paper neither claims the subject of the present application as claimed, nor does it suggest it. Die FR 2 740 339 A1 betrifft die Anwendung wenigstens eines NO-Synthase Inhibitors in einer kosmetischen Zusammensetzung als Wirkstoff zur prophylaktischen oder therapeutischen Behandlung empfindlicher Haut (Anspruch 1). Ausführungsbeispiel 6 betrifft eine Öl-in-Wasser Emulsion einer Sonnenpflegecreme, die neben üblichen Kosmetika den NO-Synthase Inhibitor 7-Nitroindazol in einer Menge von 0,5 % enthält. Jegliche im Patent angeführte Substanzen, beispielsweise das N-Monomethyl-Arginin (NMMA), N-Dimethyl- Arginin (NDMA) sowie 7-Nitroindazol sind, wie im Fall der ersten beiden Substanzen, unspezifische Hemmstoffe für alle NO-Synthasen und bei der letzten Substanz ein relativ spezifischer Hemmstoff für neuronale NO-Synthase..FR 2 740 339 A1 relates to the use of at least one NO synthase inhibitor in a cosmetic composition as an active ingredient for the prophylactic or therapeutic treatment of sensitive skin (claim 1). Embodiment 6 relates to an oil-in-water emulsion of a sun care cream which, in addition to conventional cosmetics, contains the NO synthase inhibitor 7-nitroindazole in an amount of 0.5%. Any of the substances listed in the patent, such as N-monomethyl-arginine (NMMA), N-dimethyl-arginine (NDMA) and 7-nitroindazole, are, as in the case of the first two substances, non-specific inhibitors for all NO synthases and the last Substance a relatively specific inhibitor for neuronal NO synthase .. 21 Damit ist in dieser Patentanmeldung genau das entgegensetzte Prinzip beansprucht, wie in der vorliegenden Erfindung.21 Thus, the opposite principle is claimed in this patent application, as in the present invention. Insofern nimmt auch diese Offenlegungsschrift den Gegenstand der vorliegenden Erfindung weder in allen Aspekten vorweg, noch legt sie ihn nahe.In this respect, this published specification neither anticipates the subject matter of the present invention in all aspects, nor does it suggest it. Die US-A-6, 103,275 beansprucht gemäß Hauptanspruch ein Verfahren zur therapeutischen Anwendung von NO, wobei das Verfahren darin besteht, dass zunächst ein Nitritsalz und eine biokompatible Reduziersubstanz enthaltendes Gel und ein zweites Gel mit einer Säure mit einem pKa-Wert zwischen 1 und 4 auf den Körper in einer solchen Menge aufgetragen werden, dass der lokale Blutfluss erhöht wird. Dieses Verfahren entspricht im wesentlichen dem bereits vorstehend in der Publikation von OMEROD beschriebenen Feststellung.US-A-6, 103,275 claims according to the main claim a method for the therapeutic use of NO, the method consisting in first containing a nitrite salt and a biocompatible reducing substance and a second gel with an acid with a pKa value between 1 and 4 are applied to the body in such an amount that the local blood flow is increased. This procedure corresponds essentially to the statement already described above in the OMEROD publication. Auch hierdurch wird der Gegenstand der vorliegenden Erfindung, wie beansprucht, nicht vorweggenommen. Da diese Druckschrift nur voreingereicht, aber nachveröffentlicht ist, muss auf eine erfinderische Tätigkeit hier nicht eingegangen werden.This also does not anticipate the subject matter of the present invention as claimed. Since this publication is only pre-submitted but subsequently published, there is no need to go into inventive step here. 22 22
PCT/EP2000/008067 1999-09-22 2000-08-18 No-liberating topically applicable composition as biological agent, production and utilization thereof as dermatological and/or cosmetic product Ceased WO2001021148A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP00958469A EP1216019A1 (en) 1999-09-22 2000-08-18 No-liberating topically applicable composition as biological agent, production and utilization thereof as dermatological and/or cosmetic product
AU69972/00A AU6997200A (en) 1999-09-22 2000-08-18 No-liberating topically applicable composition as biological agent, production and utilization thereof as dermatological and/or cosmetic product

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DE19945484A DE19945484A1 (en) 1999-09-22 1999-09-22 NO-releasing topically applicable composition
DE19945484.1 1999-09-22

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