US20090076084A1 - Wound and mucous membrane disinfectant - Google Patents

Wound and mucous membrane disinfectant Download PDF

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Publication number
US20090076084A1
US20090076084A1 US12/064,746 US6474606A US2009076084A1 US 20090076084 A1 US20090076084 A1 US 20090076084A1 US 6474606 A US6474606 A US 6474606A US 2009076084 A1 US2009076084 A1 US 2009076084A1
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US
United States
Prior art keywords
disinfectant
weight
propanol
glycerin
ethanol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US12/064,746
Other languages
English (en)
Inventor
Barbara Krug
Sven Dabek
Kai-Martin Mueller
Marco Rudolf
Hanns Pietsch
Hiltraut Pietsch
Christiane Ostermeyer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bode Chemie GmbH and Co KG
Original Assignee
Bode Chemie GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=37067642&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20090076084(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bode Chemie GmbH and Co KG filed Critical Bode Chemie GmbH and Co KG
Assigned to BODE CHEMIE GMBH & CO. KG reassignment BODE CHEMIE GMBH & CO. KG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RUDOLF, MARCO, DABEK, SVEN, KRUG, BARBARA, MUELLER, KAI-MARTIN, OSTERMEYER, CHRISTIANE
Assigned to BODE CHEMIE GMBH & CO. KG reassignment BODE CHEMIE GMBH & CO. KG DISTRICT COURT HAMBURG JOINT WILL WITH VERIFIED ENGLISH LANGUAGE TRANSLATION Assignors: PIETSCH, HILTRAUT AS LEGAL REPRESENTATIVE FOR THE DECEASED PIETSCH, HANNS
Publication of US20090076084A1 publication Critical patent/US20090076084A1/en
Assigned to BODE CHEMIE GMBH reassignment BODE CHEMIE GMBH CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: BODE CHEMIE GMBH & CO KG
Abandoned legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

Definitions

  • the present invention relates to an aqueous wound and mucous membrane disinfectant on the basis of octenidine dihydrochloride, which contains further ingredients from the group ethanol, propan-1-ol, propan-2-ol, undecylene amidopropyl trimonium methosulfate, sodium hydroxymethylglycinate, and 3-(4-chlorophenoxy)-1,2 propanediol.
  • the disinfectant according to the present invention has a pH value of from 5 to 7 and is free of phenoxyethanol, phenoxypropanol, phenoxyisopropanol and organic acids.
  • a wound and mucous membrane disinfectant should primarily meet certain microbiological requirements, which are described, for example, in F.-A. Pitten, H.-P. Werner, A. Kramer, “A standardized test to assess the impact of different organic challenges on the antimicrobial activity to antiseptics,” Journal of Hospital Infection (2003) 55, 108-115. However, increasing importance is also being attached to the wound, skin or mucous membrane tolerance of a corresponding disinfectant.
  • Iodine and PVP-iodine frequently trigger allergies with hypersensitivity, moreover, the skin is strongly colored and iodine, particularly from alcoholic solutions, penetrates through the skin and even more markedly through the mucous membrane, which can lead to hyperthyroidosis and even iodism in sensitive persons. Although these side effects are slighter with PVP-iodine, they are likewise manifest.
  • chlorhexidine and salts thereof are the most important active ingredients in antiseptics worldwide, although these compounds are viewed critically from a toxicological standpoint. Chlorhexidine is positive in the Ames Test and in the DNA Repair Test. Both results indicate a mutagenic potential.
  • the breakdown products 4-chloraniline and 4-chlorophenyl isocyanate have a great affinity to the skin and concentrate there with frequent use. Triclosan, a chlorinated phenol, penetrates through the skin to a great extent and is a potential dioxin former.
  • Octenidine dihydrochloride is known as an active ingredient in mucous membrane and wound antiseptics and can be described by the limiting structure formulae below:
  • the raw material octenidine dihydrochloride has a good microbicidal effectiveness with relatively good tolerance.
  • an aqueous mucous membrane antiseptic is described, which contains phenoxyethanol and/or phenoxypropanol in addition to octenidine dihydrochloride to increase effectiveness.
  • a preparation of this type is commercially available, e.g., under the name “Octenisept” and is often used in gynecology and andrology.
  • Octenisept e.g., under the name “Octenisept”
  • recent tests have shown that the combination of octenidine dihydrochloride and phenoxyethanol has a high cytotoxicity, so that considerable reservations are justified regarding use on open wounds.
  • wound and mucous membrane disinfectants which, in addition to octenidine dihydrochloride, now contain ethanol and a physiologically tolerated organic acid instead of the above-referenced combination.
  • organic acids lactic acid, glycolic acid, malonic acid, succinic acid, malic acid, tartaric acid, or citric acid.
  • the pH value of these solutions is 2.5 to 3.0. Acid preparations in this very low range can definitely be tolerated with infrequent use, but represent a noxa with longer-term application.
  • microbicidal active ingredients have a certain irritative potential, to which the mucous membranes react with particular sensitivity.
  • the object of the invention was therefore to develop a wound and mucous membrane disinfectant based on octenidine dihydrochloride, which on the one hand meets the microbicidal requirements—particularly with respect to the effectiveness regarding Candida albicans —but on the other hand has a more favorable pH value compared with the formulas of the prior art and thus a better wound, skin or mucous membrane tolerance.
  • Particularly preferred components according to the invention according to b) are 1-propanol and ethanol.
  • Particularly preferred ingredients according to the invention according to c) are glycerin, 1,2-propanediol, 1,2-butanediol, 1,2-pentanediol and/or 1,2-hexanediol.
  • the content of octenidine dihydrochloride is selected from the range of 0.05 to 0.2% by weight. Particularly preferably, the content of octenidine dihydrochloride is approx. 0.1% by weight, in order to achieve a very good microbicidal effectiveness with at the same time excellent skin tolerance.
  • the wound and mucous membrane disinfectant according to the invention contains
  • a wound and mucous membrane disinfectant according to the invention is particularly preferred which consists of:
  • a wound and mucous membrane disinfectant is particularly preferred according to the invention.
  • the wound and mucous membrane disinfectants according to the invention can in addition contain other substances such as dyestuffs, perfumes, emulsifiers, solubilizers, pH regulators, thickeners and/or surfactants.
  • substances such as dyestuffs, perfumes, emulsifiers, solubilizers, pH regulators, thickeners and/or surfactants.
  • dyestuffs perfumes, emulsifiers, solubilizers, pH regulators, thickeners and/or surfactants.
  • surfactants Preferably according to the invention, only those substances are taken into consideration for this purpose that have no or only a very low additional irritative potential.
  • Surfactants and emulsifiers are accordingly particularly suitable for an application for the purposes of the present invention which show no or only a very low irritative potential in the red blood cell test (RBC test) code 11035 and/or in the hen's egg test chorioaallantoic membrane code 11087 (HET-CAM test).
  • RBC test red blood cell test
  • HET-CAM test hen's egg test chorioaallantoic membrane code 11087
  • Surfactants that are suitable and accordingly advantageously to be used for the purpose of the present invention are, for example, ethoxylated glyceryl palmitate (INCI name: PEG-200 hydrogenated glyceryl palmate), ethoxylated sorbitan laurate (INCI: PEG-80 sorbitan laurate), ethoxylated glyceryl isostearate (INCI: PEG-90 glyceryl isostearate), ethoxylated lauryl alcohol (INCI: laureth-2) or also betaines such as, e.g., cocamidopropyl betaine (INCI), a concentration between 0 and 1.0% by weight having proven advantageous.
  • the emulsifiers reference is made by way of example to the ethoxylated fatty alcohols or also fatty acid esters (INCI: ceteareth-20, glyceryl stearate).
  • the wound and mucous membrane disinfectants according to the invention are clear solutions with a pH value of from 5 to 7.
  • This pH value results, for example, in the particularly preferred formula “by itself,” as it were. In other cases it may be necessary to adjust the pH value accordingly.
  • aqueous sodium hydroxide or phosphoric acid have proven useful for this purpose.
  • the wound and mucous membrane disinfectants can advantageously also contain thickeners for the purpose of the present invention.
  • Synthetic polymers on a polyacrylic acid basis or natural thickeners, such as xanthan gum or modified natural types of thickeners, such as, e.g., cellulose derivatives, are preferably to be used according to the invention.
  • wound and mucous membrane disinfectant according to the invention can be used in different application forms, e.g., per se (i.e., in the form of an aqueous solution), as a gel or as an impregnation solution for wipes and/or bandages.
  • the wound or mucous membrane disinfectant for the purpose of the present invention can furthermore preferably also represent the aqueous phase of an emulsion that furthermore contains as oil phase those lipids that are known to be particularly well tolerated by wounds and mucous membranes, such as, e.g., natural oils or modified oils and fats (e.g., almond oil, hydrogenated castor oil).
  • the subject of the present invention are therefore also O/W or W/O emulsions—e.g., in the form of a cream, lotion or a spray—which comprise the aqueous mucous membrane disinfectant.
  • O/W or W/O emulsions e.g., in the form of a cream, lotion or a spray—which comprise the aqueous mucous membrane disinfectant.
  • Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Phosphoric acid solution Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Var. Water ad ad ad ad ad ad ad ad ad ad ad ad 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Quantities in % by weight

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US12/064,746 2005-08-26 2006-07-31 Wound and mucous membrane disinfectant Abandoned US20090076084A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE102005041730 2005-08-26
DE102005041730.2 2005-08-26
DE102005058978.2 2005-12-09
DE102005058978A DE102005058978A1 (de) 2005-08-26 2005-12-09 Wund- und Schleimhautdesinfektionsmittel
PCT/EP2006/064836 WO2007023066A1 (de) 2005-08-26 2006-07-31 Wund- und schleimhautdesinfektionsmittel

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/064836 A-371-Of-International WO2007023066A1 (de) 2005-08-26 2006-07-31 Wund- und schleimhautdesinfektionsmittel

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/236,847 Continuation US8465766B2 (en) 2005-08-26 2011-09-20 Wound and mucous membrane disinfectant

Publications (1)

Publication Number Publication Date
US20090076084A1 true US20090076084A1 (en) 2009-03-19

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ID=37067642

Family Applications (2)

Application Number Title Priority Date Filing Date
US12/064,746 Abandoned US20090076084A1 (en) 2005-08-26 2006-07-31 Wound and mucous membrane disinfectant
US13/236,847 Expired - Fee Related US8465766B2 (en) 2005-08-26 2011-09-20 Wound and mucous membrane disinfectant

Family Applications After (1)

Application Number Title Priority Date Filing Date
US13/236,847 Expired - Fee Related US8465766B2 (en) 2005-08-26 2011-09-20 Wound and mucous membrane disinfectant

Country Status (5)

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US (2) US20090076084A1 (de)
EP (1) EP1924144B2 (de)
DE (1) DE102005058978A1 (de)
PL (1) PL1924144T5 (de)
WO (1) WO2007023066A1 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8541454B2 (en) 2010-07-02 2013-09-24 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Antiseptic based on bispyridinium alkanes
US8815912B2 (en) 2009-10-15 2014-08-26 L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Wound and mucosa antiseptic based on bispyridiniumalkanes
US8999399B2 (en) 2008-12-18 2015-04-07 Bose Chemie GmbH Combined disinfection and decontamination agent having increased effectiveness
US12295923B2 (en) 2018-12-27 2025-05-13 Solventum Intellectual Properties Company Antimicrobial compositions with 1,2-alkanediols
WO2025143692A1 (ko) * 2023-12-27 2025-07-03 장병모 상처 및 흉터 치료용 약학적 조성물

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006051891A1 (de) * 2006-10-31 2008-05-08 Schülke & Mayr GmbH Antimikrobiell wirksame Zusammensetzung mit einem Gehalt an Bispyridiniumalkan
EP2201951A1 (de) * 2008-11-14 2010-06-30 Ahmet Melih Aydinoglu Octenidin-Zusammensetzung
EP3111958A1 (de) 2015-06-30 2017-01-04 Pharmbridge Sp. z o.o. Aggregat von phosphatidylcholin und octenidin, formulierungen und verfahren zur erhaltung
DE102015113641A1 (de) 2015-08-18 2017-02-23 Bode Chemie Gmbh Desinfektionsmittel mit organischen Säuren
DE102015122276A1 (de) * 2015-12-18 2017-06-22 Schülke & Mayr GmbH Alkoholische Zusammensetzungen mit einem Gehalt an Octenidindihydrochlorid
DE102015122263A1 (de) * 2015-12-18 2017-06-22 Schülke & Mayr GmbH Alkoholisches Desinfektionsmittel für die Bekämpfung von Viren
US10264788B2 (en) * 2015-12-30 2019-04-23 Carefusion 2200, Inc. Antimicrobial wipe
ES2919723B2 (es) * 2021-11-05 2025-01-20 Bio Logic Crop Science S L Composicion con actividad virucida, su uso y metodo de aplicacion

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4542125A (en) * 1984-03-23 1985-09-17 Sterling Drug Inc. Antimicrobial surface degerming compositions and method of use thereof
US4839372A (en) * 1984-09-12 1989-06-13 Sterling Drug Inc. Antimicrobial N-[1-(alkyl or arylmethyl)-4(1H)-pyridinylidine]-alkanamines and acid addition salts thereof and methods of use and compositions thereof
US20010036963A1 (en) * 1996-11-05 2001-11-01 Air Liquide Sante (International) Washing disinfectant for hygienic and surgical hand disinfection
US20040092588A1 (en) * 2001-03-01 2004-05-13 Axel Kramer Antiseptic for wounds and mucous membranes
US20050119313A1 (en) * 2002-02-13 2005-06-02 Sabine Behrends Aqueous antiseptic based on bispyridiniumalkanes

Family Cites Families (9)

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US4206215A (en) † 1976-02-25 1980-06-03 Sterling Drug Inc. Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes
DE3925540C1 (de) * 1989-08-02 1990-08-30 Schuelke & Mayr Gmbh, 2000 Norderstedt, De
GB9204410D0 (en) * 1992-02-29 1992-04-15 Smithkline Beecham Plc Method of treatment
DE4240674C2 (de) * 1992-11-26 1999-06-24 Schuelke & Mayr Gmbh Desodorierende Wirkstoffe
AUPO690997A0 (en) * 1997-05-20 1997-06-12 Novapharm Research (Australia) Pty Ltd Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism
US6350438B1 (en) * 1998-02-27 2002-02-26 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
JP2004517038A (ja) * 2000-06-30 2004-06-10 ザ、プロクター、エンド、ギャンブル、カンパニー 全身の健康増進
DE102005002645A1 (de) * 2005-01-19 2006-07-20 Schülke & Mayr GmbH Alkoholische Zusammensetzungen für die Desinfektion
EP2497460A1 (de) * 2005-03-10 2012-09-12 3M Innovative Properties Co. Verfahren zur Reduktion von mikrobieller Kontamination

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4542125A (en) * 1984-03-23 1985-09-17 Sterling Drug Inc. Antimicrobial surface degerming compositions and method of use thereof
US4839372A (en) * 1984-09-12 1989-06-13 Sterling Drug Inc. Antimicrobial N-[1-(alkyl or arylmethyl)-4(1H)-pyridinylidine]-alkanamines and acid addition salts thereof and methods of use and compositions thereof
US20010036963A1 (en) * 1996-11-05 2001-11-01 Air Liquide Sante (International) Washing disinfectant for hygienic and surgical hand disinfection
US20040092588A1 (en) * 2001-03-01 2004-05-13 Axel Kramer Antiseptic for wounds and mucous membranes
US20050119313A1 (en) * 2002-02-13 2005-06-02 Sabine Behrends Aqueous antiseptic based on bispyridiniumalkanes

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8999399B2 (en) 2008-12-18 2015-04-07 Bose Chemie GmbH Combined disinfection and decontamination agent having increased effectiveness
US8815912B2 (en) 2009-10-15 2014-08-26 L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Wound and mucosa antiseptic based on bispyridiniumalkanes
US8541454B2 (en) 2010-07-02 2013-09-24 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Antiseptic based on bispyridinium alkanes
US12295923B2 (en) 2018-12-27 2025-05-13 Solventum Intellectual Properties Company Antimicrobial compositions with 1,2-alkanediols
WO2025143692A1 (ko) * 2023-12-27 2025-07-03 장병모 상처 및 흉터 치료용 약학적 조성물

Also Published As

Publication number Publication date
WO2007023066A8 (de) 2007-05-10
US8465766B2 (en) 2013-06-18
EP1924144B1 (de) 2014-04-09
DE102005058978A1 (de) 2007-03-29
PL1924144T3 (pl) 2014-10-31
PL1924144T5 (pl) 2018-05-30
US20120070510A1 (en) 2012-03-22
WO2007023066A1 (de) 2007-03-01
EP1924144B2 (de) 2017-10-11
EP1924144A1 (de) 2008-05-28

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Owner name: BODE CHEMIE GMBH & CO. KG, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KRUG, BARBARA;DABEK, SVEN;MUELLER, KAI-MARTIN;AND OTHERS;REEL/FRAME:021090/0629;SIGNING DATES FROM 20080416 TO 20080418

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Owner name: BODE CHEMIE GMBH & CO. KG, GERMANY

Free format text: DISTRICT COURT HAMBURG JOINT WILL WITH VERIFIED ENGLISH LANGUAGE TRANSLATION;ASSIGNOR:PIETSCH, HILTRAUT AS LEGAL REPRESENTATIVE FOR THE DECEASED PIETSCH, HANNS;REEL/FRAME:021391/0214

Effective date: 20080428

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