WO2014165226A2 - Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar - Google Patents

Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar Download PDF

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Publication number
WO2014165226A2
WO2014165226A2 PCT/US2014/024864 US2014024864W WO2014165226A2 WO 2014165226 A2 WO2014165226 A2 WO 2014165226A2 US 2014024864 W US2014024864 W US 2014024864W WO 2014165226 A2 WO2014165226 A2 WO 2014165226A2
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WO
WIPO (PCT)
Prior art keywords
composition
paag
amount
oil
present
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.)
Ceased
Application number
PCT/US2014/024864
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English (en)
French (fr)
Other versions
WO2014165226A3 (en
Inventor
Stacy M. TOWNSEND
Shenda Baker
William P. Wiesmann
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.)
Synedgen Inc
Original Assignee
Synedgen Inc
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
Application filed by Synedgen Inc filed Critical Synedgen Inc
Priority to US14/775,679 priority Critical patent/US20160022564A1/en
Priority to EP14779111.5A priority patent/EP2968080B1/en
Priority to AU2014248562A priority patent/AU2014248562B2/en
Priority to CA2905404A priority patent/CA2905404C/en
Priority to JP2016501663A priority patent/JP6842916B2/ja
Publication of WO2014165226A2 publication Critical patent/WO2014165226A2/en
Publication of WO2014165226A3 publication Critical patent/WO2014165226A3/en
Anticipated expiration legal-status Critical
Priority to US15/948,446 priority patent/US10765616B2/en
Priority to AU2019202092A priority patent/AU2019202092A1/en
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C17/00—Devices for cleaning, polishing, rinsing or drying teeth, teeth cavities or prostheses; Saliva removers; Dental appliances for receiving spittle
    • A61C17/16—Power-driven cleaning or polishing devices
    • A61C17/20—Power-driven cleaning or polishing devices using ultrasonics
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • 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
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A61K31/722—Chitin, chitosan
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A61Q17/005—Antimicrobial preparations

Definitions

  • the PAAG is present in the composition at an amount of at least 0.003% to about 0.01% w/v of PAAG. In some aspects of these embodiments, the PAAG is present in the composition at an amount of at least 0.01% w/v of PAAG.
  • the preservative is benzoic acid.
  • the benzoic acid is present in the composition at an amount of about 0.01% to about 4% by weight.
  • the composition comprises an anti-caries agent.
  • the anti-caries agent is a fluoride, e.g., sodium fluoride.
  • the sodium fluoride is present in the composition at an amount of 0% to about 0.1 % by weight.
  • the PAAG is present in the composition at an amount of at least 0.004% to about 0.05% w/v of PAAG. In some aspects of these embodiments, the PAAG is present in the composition at an amount of at least 0.004% to about 0.02% w/v of PAAG. In some aspects of these embodiments, the PAAG is present in the composition at an amount of at least 0.01 % w/v of PAAG. In some aspects of these embodiments, the PAAG is present in the composition at an amount of at least 0.01% to about 0.05% w/v of PAAG. In some aspects of these embodiments, the PAAG is present in the composition at an amount of at least 0.01 % to about 0.02% w/v of PAAG.
  • the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.0 and 2.5. In some embodiments, the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.2 and 2.5. In some embodiments, the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.5 and 2.0.
  • polyglucosamine is soluble in aqueous solution (e.g., prepared in aqueous solution) between pH 2 and 10. In some embodiments, the derivatized polyglucosamine is soluble in aqueous solution (e.g., prepared in aqueous solution) between pH 5 and 9. In some embodiments, the derivatized polyglucosamine is soluble in aqueous solution (e.g., prepared in aqueous solution) between pH 6 and pH 8. In some embodiments, the derivatized polyglucosamine is soluble in aqueous solution (e.g., prepared in aqueous solution) between pH 6.5 and pH 8. In some embodiments, the derivatized polyglucosamine is soluble in aqueous solution (e.g., prepared in aqueous solution) between pH 7 and pH 8.
  • aqueous solution e.g., prepared in aqueous solution
  • the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.0 and 2.5. In some embodiments, the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.2 and 2.5. In some embodiments, the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.5 and 2.0.
  • the invention features an oral care composition
  • a plurality non- fermentable sugars e.g., sorbitol and xylitol
  • glycerin in an amount of about 12.5% w/v
  • polysorbate 20 in an amount of about 1 % w/v
  • peppermint oil in an amount of about 0.18% w/v
  • benzoic acid in an amount of about 0.1 % w/v
  • PAAG in an amount of about 0.004% w/v.
  • the composition comprises an anti-caries agent.
  • the anti-caries agent is a fluoride, e.g., sodium fluoride.
  • the sodium fluoride is present in the composition at an amount of 0% to about 0.1 % by weight.
  • the composition further comprises sodium hydroxide.
  • the sodium hydroxide is present in the composition at an amount of less than 0.25% by weight (e.g. , less than 0.1 %).
  • PAAG comprises the following formula (I):
  • the polyglucosamine is functionalized at between 18% and 30%.
  • the degree of deacetylation ( DDA) of the derivatized polyglucosamine is between 75% and 99%.
  • the degree of deacetylation (%DDA) of the derivatized polyglucosamine is between 80% and 98%.
  • polyglucosamine is between 1.2 and 2.5. In some embodiments, the polydispersity index (PDI) of the derivatized polyglucosamine is between 1.5 and 2.0.
  • the method further comprises a step of administering an antibiotic or antiseptic to a subject, in a dosage to achieve a synergistic effect.
  • the antibiotic or antiseptic is metronidazole, hydrogen peroxide, cetylpryridinium chloride, hypochlorite, chlorine dioxide, xylitol, or chlorhexidine.
  • compositions comprising a soluble polyglucosamine or a derivatized polyglucosamine.
  • the composition is a liquid, solid, or semisolid composition, in some embodiments, the composition is an oral rinse (i.e., a mouth rise, mouth wash or oral wash).
  • compositions and components described herein can be provided in the form of an oral rinse.
  • Soluble poly glucosamines and poly glucosamines derivatives Compounds and compositions containing a soluble polyglucosamine or a derivatized polyglucosamine for treating or preventing a disease or symptom of a disease described herein, e.g., an oral disease or a symptom of an oral disease, e.g,. gingivitis, dental caries, dental plaque, halitosis.
  • a disease or symptom of a disease described herein e.g., an oral disease or a symptom of an oral disease, e.g,. gingivitis, dental caries, dental plaque, halitosis.
  • R 3 is an unnatural amino acid side chain, and wherein at least 25% of R 1 substituents are H, at least 1% are acetyl, and at least 2% are a group of the formula shown above.
  • administered in combination or a combined administration of two agents means that two or more agents (e.g., compounds described herein) are administered to a subject at the same time or within an interval such that there is overlap of an effect of each agent on the patient. Preferably they are administered within 15, 10, 5, or 1 minute of one another. Preferably the administrations of the agents are spaced sufficiently close together such that a combinatorial (e.g., a synergistic) effect is achieved.
  • a combinatorial e.g., a synergistic
  • Exemplary combinations of a derivatized polyglucosamine described herein and one or more of antimicrobial agent(s) such as an antibiotic are described, e.g., in US Publication US20100130443, which is incorporated by reference herein by its entirety.
  • quinolones include Ciprofloxacin, Cipro, Ciproxin, Ciprobay, Enoxacin, Gatifloxacin, Tequin, Levofloxacin, Levaquin, Lomefloxacin, Moxifloxacin, Avelox, Norfloxacin, Noroxin, Ofloxacin, Ocuflox, Trovafloxacin, and Trovan.
  • compositions and compounds described herein can be used alone or in combination with one or more anti-inflammatory drugs, e.g., steroidal anti-inflammatory drugs and non-steroidal anti-inflammatory drugs (NSAIDs), to reduce bacteria in the mouth, or to treat or prevent an oral disease or condition, e.g., dental plaque, gingivitis, dental caries, or halitosis.
  • anti-inflammatory drugs e.g., steroidal anti-inflammatory drugs and non-steroidal anti-inflammatory drugs (NSAIDs)
  • NSAIDs non-steroidal anti-inflammatory drugs
  • the administrations of a combination of agents and therapeutics are spaced sufficiently close together such that a synergistic effect is achieved.
  • FIG. 11 Exemplary MBEC peg biofilm reduction assay of PAAG-based oral rinse compared to other products (twice daily treatment).
  • FIG. 15 Exemplary bactericidal activity of combinations of PAAG and xylitol demonstrating synergy.
  • FIG. 20 Optimization studies of antibacterial activity and mouth feel and taste.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Molecular Biology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dentistry (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
PCT/US2014/024864 2013-03-12 2014-03-12 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar Ceased WO2014165226A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US14/775,679 US20160022564A1 (en) 2013-03-12 2014-03-12 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
EP14779111.5A EP2968080B1 (en) 2013-03-12 2014-03-12 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
AU2014248562A AU2014248562B2 (en) 2013-03-12 2014-03-12 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
CA2905404A CA2905404C (en) 2013-03-12 2014-03-12 Oral formulations of polyglucosamine derivatives in combination with a non-fermentable sugar
JP2016501663A JP6842916B2 (ja) 2013-03-12 2014-03-12 非発酵性糖と組み合わせたポリグルコサミン誘導体の経口製剤
US15/948,446 US10765616B2 (en) 2013-03-12 2018-04-09 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
AU2019202092A AU2019202092A1 (en) 2013-03-12 2019-03-26 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361778077P 2013-03-12 2013-03-12
US61/778,077 2013-03-12

Related Child Applications (2)

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US14/775,679 A-371-Of-International US20160022564A1 (en) 2013-03-12 2014-03-12 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar
US15/948,446 Continuation US10765616B2 (en) 2013-03-12 2018-04-09 Oral formulation of polyglucosamine derivatives in combination with a non-fermentable sugar

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WO2014165226A2 true WO2014165226A2 (en) 2014-10-09
WO2014165226A3 WO2014165226A3 (en) 2014-12-31

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US (2) US20160022564A1 (enExample)
EP (1) EP2968080B1 (enExample)
JP (2) JP6842916B2 (enExample)
AU (2) AU2014248562B2 (enExample)
CA (1) CA2905404C (enExample)
WO (1) WO2014165226A2 (enExample)

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WO2014165226A3 (en) 2014-12-31
AU2014248562A1 (en) 2015-10-01
JP2016512545A (ja) 2016-04-28
JP2019137702A (ja) 2019-08-22
US10765616B2 (en) 2020-09-08
CA2905404C (en) 2021-07-20
US20180289609A1 (en) 2018-10-11
US20160022564A1 (en) 2016-01-28
EP2968080A2 (en) 2016-01-20
AU2014248562B2 (en) 2019-01-03
AU2019202092A1 (en) 2019-04-18
CA2905404A1 (en) 2014-10-09
EP2968080B1 (en) 2023-05-10
EP2968080A4 (en) 2016-08-31

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