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WO2013150993A1 - Agent pharmaceutique pour prévenir ou traiter la gingivite - Google Patents

Agent pharmaceutique pour prévenir ou traiter la gingivite Download PDF

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Publication number
WO2013150993A1
WO2013150993A1 PCT/JP2013/059824 JP2013059824W WO2013150993A1 WO 2013150993 A1 WO2013150993 A1 WO 2013150993A1 JP 2013059824 W JP2013059824 W JP 2013059824W WO 2013150993 A1 WO2013150993 A1 WO 2013150993A1
Authority
WO
WIPO (PCT)
Prior art keywords
gingivitis
plaque
gingival
medicament according
alkyl group
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/JP2013/059824
Other languages
English (en)
Japanese (ja)
Inventor
桂子 成瀬
達昭 松原
俊英 野口
紀和 大野
水谷 誠
西川 徹
千尋 日比
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.)
Sanwa Kagaku Kenkyusho Co Ltd
AICHI GAKUIN
Original Assignee
Sanwa Kagaku Kenkyusho Co Ltd
AICHI GAKUIN
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 Sanwa Kagaku Kenkyusho Co Ltd, AICHI GAKUIN filed Critical Sanwa Kagaku Kenkyusho Co Ltd
Publication of WO2013150993A1 publication Critical patent/WO2013150993A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic 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
    • A61K31/41641,3-Diazoles
    • A61K31/41881,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10Spiro-condensed systems
    • C07D491/107Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring

Definitions

  • the present invention relates to a medicament for preventing or treating gingivitis comprising a hydantoin derivative as an active ingredient.
  • Periodontal disease is a general term for all diseases that occur in periodontal tissues (gingiva, cementum, periodontal ligament and alveolar bone) represented by gingivitis, periodontitis and the like.
  • gingivitis develops due to the accumulation of plaque, etc., and a periodontal pocket is formed by leaving it alone, after which periodontopathic bacteria propagate in the periodontal pocket.
  • Periodonitis develops.
  • Gingivitis and periodontitis are related diseases, but can be distinguished by pathology, pathogenic bacteria, and the like.
  • gingivitis is a lesion limited to the gingiva with no attachment loss (loss of adhesion between the gingival epithelium and cementum), while periodontitis is inflammation in the deep periodontal tissue due to the destruction of gingival epithelial attachment. It is a disease that spreads and causes attachment loss and bone resorption.
  • gingivitis is an inflammatory disease of only gingiva, it can be reversibly cured by removing (treating) its cause, and periodontitis is an irreversible destruction of alveolar bone and periodontal ligament It can be regarded as a disease that is difficult and difficult to cure.
  • the pathogenic bacteria are also different.
  • Periodontitis is caused by supragingival plaque centered on Gram-positive cocci.
  • periodontitis is deeply related to periodontopathic bacteria such as Porphyromonas gingivalis, which is a Gram-negative anaerobic bacterium present under the gingival margin. That is, in gingivitis, inflammatory cytokine production is induced by bacterial infection, gingival capillaries are stimulated to cause vasodilation and / or increased vascular permeability, and neutrophils infiltrate into an inflammatory state.
  • gingivitis inflammatory cytokine production is induced by bacterial infection, gingival capillaries are stimulated to cause vasodilation and / or increased vascular permeability, and neutrophils infiltrate into an inflammatory state.
  • gingivitis inflammatory cytokine production is induced by bacterial infection, gingival capillaries are stimulated to cause vasodilation and / or increased vascular permeability, and neutrophils in
  • gingivitis treatment is based on plaque control and scaling (calculus removal), and is considered to improve if daily oral cleaning is done perfectly.
  • active drug treatment is being carried out because there are few drugs that have sufficient therapeutic effects for gingivitis.
  • (2S, 4S) -6-Fluoro-2 ', 5'-dioxospiro [chroman-4,4'-imidazolidine] -2-carboxamide (generic name Fidarestat) is an aldose reductase (AR) inhibitor are known.
  • aldose reductase inhibitors such as fidarestat have been reported to have pharmacological effects on various diseases, but there are reports on gingivitis and the effectiveness against gingivitis. There is no report example to do.
  • fidarestat because of the high prevalence of gingivitis due to incomplete plaque control, and from the viewpoint of preventing progression to more serious periodontitis and periodontal disease, development of a drug for the prevention or treatment of gingivitis is expected Has been.
  • an object of the present invention is to provide a preventive agent for gingivitis or a therapeutic agent having a therapeutic effect for gingivitis for reducing the incidence of gingivitis.
  • hydantoin derivatives represented by the following general formula (I) that are aldose reductase inhibitors, (2S, 4S) -6-Fluoro-2 ', 5'-dioxospiro [chroman-4,4'-imidazolidine] -2-carboxamide (fidarestat) has been found to have preventive or therapeutic effects on gingivitis
  • the present invention has been completed. That is, the main configuration of the present invention is as follows.
  • the hydantoin derivative represented by the general formula (I) is 6-fluoro-2 ′, 5′-dioxospiro [chroman-4,4′-imidazolidine] -2-carboxamide, Medicines.
  • the medicament according to (3), wherein the 6-fluoro-2 ′, 5′-dioxospiro [chroman-4,4′-imidazolidine] -2-carboxamide is a (2S, 4S) form.
  • H / E maxillary tissue section hematocillin / eosin staining results for a normal rat gingivitis onset model are shown.
  • A Control (normal + non-administration of fidarestat);
  • B Comparative example (gingivitis + non-administration of fidarestat);
  • C Example (gingivitis + administration of fidarestat).
  • the compound of the general formula (I) is a compound well known as a compound having aldose reductase inhibitory activity, and is described in JP-A-63-057588.
  • This compound can be easily produced according to the synthesis method described in JP-A-63-057588.
  • fidarestat can be synthesized by the synthesis method of Production Example 3 (production of d-form). it can.
  • the C1-6 alkyl group is preferably a C1-3 alkyl group, and more preferably a methyl group.
  • 6-fluoro-2 ′, 5′-dioxospiro [chroman-4,4′-imidazolidine] -2-carboxamide is preferable, and in particular, fidarestat as its (2S, 4S) form is Excellent in medicinal properties and safety.
  • Gingivitis is a multifactorial disease consisting of an action factor, an environmental factor and a host factor. Gingivitis is roughly classified into plaque gingivitis, non-plaque gingival lesions, and gingival proliferation. Plaque gingivitis includes plaque solitary gingivitis, systemic factor-related gingivitis, nutritional disorder-related gingivitis. Non-plaque gingival lesions include gingival lesions caused by infections other than plaque bacteria, mucocutaneous lesions, allergic gingival lesions, and traumatic gingival lesions.
  • drug-induced gingival hyperplasia including phenytoin, nifedipine, and cyclosporin A as a causative drug and hereditary gingival fibromatosis are known for gingival proliferation.
  • the medicament of the present invention can be used for all these gingivitis, but is effective for plaque gingivitis or non-plaque gingival lesions, and more effective for plaque gingivitis. ing.
  • the pharmaceutical preparation of the present invention is administered orally, for example, as a tablet, capsule, powder, granule, solution, or syrup, or parenterally as an injection, etc., by a conventional formulation technique. be able to.
  • a conventional formulation technique for example, as a tablet, capsule, powder, granule, solution, or syrup, or parenterally as an injection, etc.
  • a conventional formulation technique for example, as a tablet, capsule, powder, granule, solution, or syrup, or parenterally as an injection, etc.
  • a conventional formulation technique be able to.
  • an ointment preparation a toothpaste, a gel agent, a pasta agent, a mouthwash, a jelly preparation, a gum agent, a film agent, and the like are possible.
  • pharmacologically acceptable excipients for formulation such as starch, lactose, purified sucrose, glucose, crystalline cellulose, carboxycellulose, carboxymethylcellulose, carboxyethylcellulose, calcium phosphate, magnesium stearate, Arabic A rubber or the like can be used, and if necessary, a lubricant, a binder, a disintegrant, a coating agent, a colorant and the like can be blended.
  • a liquid agent a stabilizer, a dissolution aid, a suspending agent, an emulsifier, a buffering agent, a preservative, and the like can be used.
  • a pharmacologically acceptable binding agent and excipient are used for formulation.
  • Additives such as agents, disintegrants, lubricants, sweeteners, flavoring agents, preservatives, coloring agents and the like can be added to the drug layer and / or the non-drug layer.
  • the dosage of the hydantoin derivative represented by the general formula (I), particularly fidarestat varies depending on symptoms, age, administration method, dosage form, etc., but usually 0.1 to 2000 mg / day per adult patient (body weight 60 kg) Preferably, 1 to 1000 mg / day of sputum is administered once or in several divided doses every day.
  • the dose for oral administration is usually 0.1 to 2000 mg / day, preferably 0.5 to 1000 mg / day, more preferably 1 to 800 mg / day per adult patient (body weight 60 kg).
  • the medicament of the present invention can treat gingivitis when administered to a patient after the onset of gingivitis, but can prevent the onset of gingivitis when administered to a healthy person who has not developed gingivitis. .
  • the present invention will be described in more detail with reference to the following examples, but these are not intended to limit the present invention, and may be changed without departing from the scope of the present invention.
  • Nylon for suture (3-0 Surgilon, Tyco Healthcare, NJ) is wrapped around the circumference to avoid damaging the cervical gingiva of the maxillary right second molar (M2) under diethyl ether general anesthesia. Ligated with the palate and used as the experiment side. The second molar (M2) on the opposite side of the same part was not treated and was used as a control side.
  • Fidarestat administration Rats treated with suture nylon thread were divided into two groups, a fidarestat (32 mg / kg / day) administration group and a non-administration group. Fidarestat was dissolved in drinking water and administered from the same day as the suture nylon thread treatment.
  • Tissue sections were stained with hematoxylin and eosin (H ⁇ E) and then observed with an optical microscope. Gingivitis was evaluated by counting the number of inflammatory cells in each of the control, examples and comparative examples. All tissue section slides were encrypted and the condition was counted by the same examiner after the condition was unknown. The number of infiltrating inflammatory cells is less than 14 / mm 2 (-), 15-29 / mm 2 ( ⁇ ), 30-49 / mm 2 (+), 50-69 / mm 2 Was evaluated as (++), and 70 / mm 2 or more were evaluated as (++++).

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/JP2013/059824 2012-04-02 2013-04-01 Agent pharmaceutique pour prévenir ou traiter la gingivite Ceased WO2013150993A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012083439A JP2015110525A (ja) 2012-04-02 2012-04-02 歯肉炎の予防又は治療のための医薬
JP2012-083439 2012-04-02

Publications (1)

Publication Number Publication Date
WO2013150993A1 true WO2013150993A1 (fr) 2013-10-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/059824 Ceased WO2013150993A1 (fr) 2012-04-02 2013-04-01 Agent pharmaceutique pour prévenir ou traiter la gingivite

Country Status (3)

Country Link
JP (1) JP2015110525A (fr)
TW (1) TW201345523A (fr)
WO (1) WO2013150993A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005072066A2 (fr) * 2004-01-30 2005-08-11 Sanwa Kagaku Kenkyusho Co Agent pour la prevention ou le traitement de la maculopathie diabetique
WO2007069727A1 (fr) * 2005-12-16 2007-06-21 Sanwa Kagaku Kenkyusho Co., Ltd. Agent destine a la prevention et au traitement de l’insuffisance renale aigue
US20100292287A1 (en) * 2009-05-14 2010-11-18 Kador Peter F Periodontitis treatment

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005072066A2 (fr) * 2004-01-30 2005-08-11 Sanwa Kagaku Kenkyusho Co Agent pour la prevention ou le traitement de la maculopathie diabetique
WO2007069727A1 (fr) * 2005-12-16 2007-06-21 Sanwa Kagaku Kenkyusho Co., Ltd. Agent destine a la prevention et au traitement de l’insuffisance renale aigue
US20100292287A1 (en) * 2009-05-14 2010-11-18 Kador Peter F Periodontitis treatment

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
HIROSHI NITTA: "Dr. Nitta no 'Shishu Chiryo Debridement Koza' Dai 1 Kai Shishubyo ni Kansuru Kiso Chishiki", DENTARU EKO, vol. 147, March 2007 (2007-03-01), pages 8 - 17 *
KOICHI ITO: "Plaque-sei Shinikuen towa", THE NIPPON DENTAL REVIEW, vol. 70, no. 4, 11 April 2010 (2010-04-11), pages 108 - 112 *
NAKAO R ET AL.: "Glycosylation of the OMP85 homolog of Porphyromonas gingivalis and its involvement in biofilm formation", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 365, no. 4, 2008, pages 784 - 789, XP022384868, DOI: doi:10.1016/j.bbrc.2007.11.035 *
PETER F. KADOR ET AL.: "Efficacy of Structurally Diverse Aldose Reductase Inhibitors on Experimental Periodontitis in Rats", J. PERIODONTOL., vol. 82, no. 6, June 2011 (2011-06-01), pages 926 - 933 *
YOICHIRO MIYAKE ET AL.: "1. Oral Infections and Biofilm", ANTIBIOTICS & CHEMOTHERAPY, vol. 26, no. 9, 2010, pages 66 - 70 *

Also Published As

Publication number Publication date
TW201345523A (zh) 2013-11-16
JP2015110525A (ja) 2015-06-18

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