CN101312766A - Treatment of sub-gingival pocket infections - Google Patents

Treatment of sub-gingival pocket infections Download PDF

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CN101312766A
CN101312766A CNA2006800435276A CN200680043527A CN101312766A CN 101312766 A CN101312766 A CN 101312766A CN A2006800435276 A CNA2006800435276 A CN A2006800435276A CN 200680043527 A CN200680043527 A CN 200680043527A CN 101312766 A CN101312766 A CN 101312766A
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gingival pocket
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G·R·珀森
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Sinclair Pharmaceuticals Ltd
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    • 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
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0063—Periodont
    • 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

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  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
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Abstract

Use of a morpholino compound having the general formula (I) wherein R1 is a straight or branched alkyl group containing (8) to (16) carbon atoms at the 2- or 3- position of the morpholino ring, and R2 is a straight or branched alkyl group containing (2) to (10) carbon atoms, substituted with a hydroxy group except in the alpha-position, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of an infected sub-gingival pocket.

Description

The treatment of sub-gingival pocket infections
Technical field
The present invention relates to the treatment that sub-gingival pocket (sub-gingival pocket) infects.
Background technology
Gum disease is the interior unsound main cause of world wide and can causes dental caries usually.Two kinds of principal modes---gingivitis and periodontitis---of gum disease come from the formation of bacterial plaque in the oral cavity, particularly are positioned at along the formation of the dental plaque of gingival edge.
Antibacterial on tooth-gingiva interface causes that gingiva tissue (being gingiva) separates with tooth, and when forming sub-gingival pocket, infection has just begun under the gum.Antibacterial assembles in periodontal pocket, causes swelling and aching of gum, and this can be enclosed in antibacterial in the sub-gingival pocket.Further the inflammation meeting increases the weight of to infect and final gingiva tissue and the bone of destroying.Because inaccessible bacterial infection and be difficult to use antibacterial at infection site, thereby the treatment gum infects especially trouble down.In addition, think and from sub-gingival pocket, can flow out gingiva liquid that this can stop any treatment reagent to enter infection site.
It is the feature of a lot of oral cavity infections that gum infects down, and described oral cavity infection comprises adult and child's chronic periodontitis, early onset periodontitis, downright bad ulcer periodontal and acute periodontitis.
Use anti-bacterial agent chlorhexidine treatment oral cavity infection at present.When chlorhexidine is used for the treatment of sub-gingival pocket infections, can cause the ugly dyeing and the sense of taste to disappear, also the zest that can make us unhappy owing to using feels to cause patient's compliance lower.This may be extremely painful.
The common feature of sub-gingival pocket infections is the combination that has the various antibacterials that are known as " red complex ".Described " red complex " comprises good fortune match stainer bacterium (Tannerellaforsythensis), porphyromonas gingivalis (Porphyromonas gingivalis) and treponema denticola (Treponema denticola), and each component that it is believed that red complex has synergism, and (for example see Holt and Ebersole, Periodontol 2000.2005; 38:72-122).Actinomyces species (Actinomyces species) such as actinobacillus actinomycetem comitans (Actinobacillus actinomycetemcomitans) also infects relevant with oral cavity (under the gum).
It is believed that the interaction between the variation of bacterium colony and the not generic antibacterial can influence the development of oral disease, and (for example referring to Socransky and Haffajee, Periodontol 2000.2005; 38:135-87).
Actinobacillus actinomycetem comitans is a kind of non-motile, gram-negative, capnophilic, fermentable coccobacillus, has been found that its nosetiology and pathogeny with child and adult periodontitis and systemic infection is relevant.Actinobacillus actinomycetem comitans has serotype a-e.The Y4 strain is serotype b.Have been found that relevant (the Califano J.V.et al of reduction to attachment loss degree in actinobacillus actinomycetem comitans serotype b (being the Y4 strain) the activated antibody of lipopolysaccharide and general the property early onset patients with periodontitis, Infection and Immunity, Sept.1996, p.3908-3910).Most of is 1gG2 (Lu et al, Infect Immun 1993 Jun to the activated antibody of actinobacillus actinomycetem comitans serotype b LPS; 61 (6): 2400-7), and also IgG2 level reduction in smoker's serum (Quinn, S.et al, Infect.Immun.64:2500-2505).It should be noted that actinobacillus actinomycetem comitans is known as Aggregatibacter actinomycetemcomitans sometimes in the art.
Except that periodontal infection, actinobacillus actinomycetem comitans also can be separated (Van Winkelhoff A.J.and Slots J.Periodontol.20001999 sometimes from serious systemic infection; 20:122-135).
Treponema denticola and periodontal such as early onset periodontitis, downright bad ulcer gingivitis and acute periodontitis be closely related (Chan EC, McLaughlin R.OralMicrobiol Immunol 200 have been proved; 15:1-9; Takeuchi Y, Umeda M, Sakamoto M, et al.J Periodontol 2001; 72:1354-1363).
Especially notice the clinical importance of periodontal bacteria pathogen coinfection recently.Porphyromonas gingivalis, actinobacillus actinomycetem comitans and treponema denticola and other gingiva lower bacteria form mixed infection, and this can cause that the periodontal more serious than single infection destroys (Langendijk-GenevauxPS et al.J Clin Periodontol 2001; 28:1151-1157; Shiloah J, etal.J Periodontol 2000; 71:562-567).
The part that the known morpholine kind compound that is commonly called delmopinol can be used as conventional oral cavity health be used for the treatment of with prophylaxis of teeth bacterial plaque and gingival plaque (for example referring to collaert etal, Sacnd J Dent Res 1994; 102:17-25).
At present the treatment gum infects down, and for example chronic periodontitis generally including operation and getting involved, and removes tissue and the bacterial plaque that infects and reduce the degree of depth of periodontal pocket from sub-gingival pocket.Even do not use open surgery, scrape under the gum that to control with root planing also be the Therapeutic Method of standard; Also can in sub-gingival pocket, insert local send antibacterial such as the liner that is soaked with antibacterial passed (for example referring to Etiene, Oral Dis.2003; 9 Suppl1:45-50).These Therapeutic Method costlinesses, consuming time, inconvenient and painful.Up to now, also not having simple antimicrobial therapy can successfully treat under the gum infects.A kind of improved method that infects of from sub-gingival pocket, removing of significant need.
Summary of the invention
The present invention is based on a surprising discovery, promptly the chemical compound of formula (I) can effectively be treated sub-gingival pocket infections.Infection is present in a lot of periodontals usually under the gum, and the chemical compound of formula (I) can be used for the treatment of these diseases.This discovery is surprising, because the chemical compound of known formula (I) only has weak anti-microbial properties and thereby can not expect that it can effectively treat tangible infection.
According to a first aspect of the invention, a kind of morpholine kind compound with general formula (I) or the purposes of its officinal salt in the medicine of the infected sub-gingival pocket of preparation treatment:
Figure A20068004352700061
R wherein 1Be the straight or branched alkyl that contains 8 to 16 carbon atoms that is positioned at morpholine ring 2 or 3, R 2It is the straight or branched alkyl that contains 2 to 10 carbon atoms.Described R 2Except that the α position, all replaced by hydroxyl.
According to a second aspect of the invention, a kind of test kit that is used for the treatment of sub-gingival pocket infections comprises a kind of chemical compound with general formula (I), also comprises the description of using the described infection of this compounds for treating.
Description of drawings
Describe the present invention with reference to following accompanying drawing, wherein:
Fig. 1 shows in four selected sub-gingival pockets, after gargling 14 days with delmopinol (once a day), and the decline of gingiva lower bacteria carrying capacity; With
Fig. 2 shows and uses the delmopinol treatment after 14 days, the decline of treponema denticola and actinobacillus actinomycetem comitans level.
The specific embodiment
The morpholine kind compound of a kind of formula (I) can be used for the treatment of the sub-gingival pocket of bacterial infection.
Morpholine kind compound of the present invention or its officinal salt have general formula (I):
Figure A20068004352700071
R wherein 1Be the straight or branched alkyl that contains 8 to 16 carbon atoms that is positioned at morpholine ring 2 or 3, R 2It is the straight or branched alkyl that contains 2 to 10 carbon atoms.Described R 2Except that the α position, all replaced by hydroxyl.In a preferred embodiment, the radicals R of described morpholine kind compound 1And R 2The summation of middle carbon number is at least 10, preferably between 10 to 20.In another preferred embodiment, R 2The end of group has hydroxyl.
Claimed morpholine kind compound itself is known and can be according to any known method preparation, US5 for example, 082,653 and WO90/14342 in disclosed method, these two pieces of documents are included this description in the form of quoting.
Preferred morpholine kind compound is 3-(4-propyl group-heptyl)-4-(2-ethoxy) morpholine among the present invention, so-called delmopinol (CAS No.79874-76-3).
Morpholine kind compound can be used with the form of its free radical or officinal salt.The example of officinal salt is a hydrochlorate, and described acid is acetic acid, phosphoric acid, boric acid, hydrochloric acid, maleic acid, benzoic acid, citric acid, malic acid, oxalic acid, tartaric acid, succinic acid, 1,3-propanedicarboxylic acid, gentisic acid, valeric acid, gallic acid, beta-resorcylic acid, aspirin, salicylic acid, perchloric acid, barbiturates, p-anilinesulfonic acid., phytic acid, Nitrodracylic acid, stearic acid, Palmic acid, oleic acid, myristic acid, lauric acid etc. for example.Most preferred salt is hydrochlorate.A kind of preferred chemical compound is hydrochloric acid delmopinol (CAS No.98092-92-3).
The used term " infection " of this description is endowed the implication commonly used in this area, and promptly the alien species harmfulness is grown surely in cell, tissue, organ or health.According to the present invention, described alien species are antibacterials.
The position of infecting is " sub-gingival pocket ".Known term " sub-gingival pocket " is meant depression or the hole that forms in this area between tooth and the gingiva tissue relevant with this tooth.Sub-gingival pocket is the symptom of carrying out property, chronic or serious gingivitis normally.Described periodontal pocket normally forms owing to gingiva tissue separates with tooth, and described separation is the reaction to initial mild bacterial infection on tooth-gingiva interface.Little---for example the degree of depth is less than 1mm's---periodontal pocket (measuring to the edge of gingiva tissue from the summit of periodontal pocket) may need not the antibacterial treatment, because common conventional oral cavity health may be just enough, for example brush teeth and may remove antibacterial.But sub-gingival pocket can develop into 12mm or darker.More serious periodontal pocket (for example be deeper than 3mm or darker, for example 4,5,6,7 or 8mm or darker) may need antibacterial treatment.Though can by with the bacterial infection of the sub-gingival pocket of any size of chemical compound contact treatment of formula (I), preferably treat darker periodontal pocket according to the present invention, for example be deeper than 3mm, preferred at least 4,5,6,7 or 8mm or darker periodontal pocket.These dark periodontal pockets may be caused by chronic periodontal infection.If the use conventional method does not get involved the infection that may be difficult to treat in the described dark periodontal pocket by operation.
Another advantage that the compounds for treating gum of surprisingly, use formula (I) infects down is that administration is painless substantially.
According to the present invention, the chemical compound of formula (I) is used for the treatment of infection under the existing gum.Described application is different from previous known use delmopinol as prevention reagent prevention infection, and the previous application of described delmopinol comes from the ability that it prevents to form supragingival plaque and gingival plaque.The patient who this chemical compound is suffered from sub-gingival pocket infections.With the chemical compound of a kind of formula (I) contact oral cavity, thereby the contact sub-gingival pocket can reduce in the infected periodontal pocket number of bacteria and make the gingiva tissue recovery.In a preferred embodiment, need not further treatment, thereby promptly gingival tissue grows is returned acceptable level " sealing " periodontal pocket.The chemical compound of formula (I) is applied to the intervention that infection site need not the doctor or the dentist (for example dental hygiene expert or periodontist) of qualification.
The present invention is equally applicable to human and animal's field of medicaments, i.e. veterinary's application also within the scope of the invention.In veterinary's embodiment, embodiment preferred is that the treatment house pet comprises that cat and Canis familiaris L. and treatment domestic animal comprise cattle and pig.
The chemical compound of formula (I) can be used for treating under the gum and to infect, and surprisingly, and it can touch position under the gum of infection.The chemical compound that has been found that a kind of formula (I) makes the level of treponema denticola significantly reduce (referring to embodiment 1).Therefore the chemical compound of formula (I) has surprising efficient reducing aspect the antibacterial of " red complex " component horizontal, and this is the feature that microbial bacteria makes a decision and grows under the gum.
The chemical compound that also has been found that a kind of formula (I) has almost been removed actinobacillus actinomycetem comitans (referring to embodiment 1).This antibacterial is relevant with the development of described red complex also to be present in the infected sub-gingival pocket usually.
The chemical compound of a kind of formula (I) can be used to change the level of specific bacteria, treponema denticola and/or actinobacillus actinomycetem comitans (also actinobacillus actinomycetem comitans being called Aggregatibacter.actinomycetemcoitans sometimes in this area) in the preferred oral cavity are preferably placed at position under the infected gum.
Do not wish to be bound by theory, think that described red complex especially bothers, because the various antibacterials in this complex interact and cause obstinate infection (for example, referring to Langendijk-Genevaux et al, above).Therefore the level that reduces at least a antibacterial in the red complex will reduce the pathogenic of this antibacterial complex, infects thereby treat effectively under the gum.
Sub-gingival pocket infections betides in the periodontal usually, for example adult and child's chronic periodontitis, early onset periodontitis, downright bad ulcer periodontal and acute periodontitis.Use routine techniques may treat other symptom of described disease, for example infection of (on the gum) dental surface and tongue.Even this class conventional therapy is successful, sub-gingival pocket infections also may keep a lower level.Therefore, when described problematic symptom is when infecting under the gum, can use the described disease of compounds for treating of formula (I).Preferably, treat chronic periodontitis with the chemical compound formula of formula (I) by the infected gum lower area of contact.
Infection also has the benefit of beauty treatment under the compounds for treating gum of use formula (I), and promptly FFI gingiva tissue is considered to pleasant aesthetically.
Can make the chemical compound of formula (I) in the mode of routine, contact with the oral cavity can reach any suitable form of required effect (promptly reducing the infection of sub-gingival pocket) or amount.Preferably, the form of the chemical compound of formula (I) is collutory, toothpaste, gutta-percha, chewing gum, dentifrice or other conspicuous for a person skilled in the art similar formulations.Most preferably, the form of described chemical compound is an aqueous mouthwash.The patient can be applied to described aqueous mouthwash in the oral cavity and need not medical advice.The chemical compound of formula (I) has the surprising ability that enters sub-gingival pocket and treatment infection.Preferably, described collutory was kept in the mouth 5 seconds at least, preferably surpass 10 seconds (for example one minute or longer), so that the chemical compound of formula (I) arrives infection site.
The chemical compound of formula (I) can be added in existing toothpaste, chewing gum, gutta-percha or the collutory prescription.The chemical compound of formula (I) can---preferred antimicrobial agents---add with at least a antimicrobial.The reagent that is fit to comprises antibiotic tetracycline, deoxycycline hydrochloride and ampicillin.Other reagent that is applicable to the treatment oral cavity infection is conspicuous for those of ordinary skills.Perhaps, the reagent of unique treatment sub-gingival pocket infections in the preparation that chemical compound is with the oral cavity contacts of formula (I).
The chemical compound of formula (I) can add with at least a antiinflammatory.Antiinflammatory is well known in the art and may uses any antiinflammatory.Preferably, described antiinflammatory is nonsteroid anti-inflammatory drugs (NSAID), for example aspirin (aspirin) or ibuprofen.In an optional embodiment, may use the steroid antiinflammatory, for example cortisone.The chemical compound of formula (I) may add with at least a antiinflammatory and at least a antimicrobial.
For avoiding query, can also in being used for the treatment of the compositions that infects under the gum, add the reagent except that the chemical compound of formula (I), for example can comprise above disclosed reagent.But, extra reagent not necessarily and in a preferred embodiment, does not comprise the additional agents with antibiotic, treatment or other pharmacotoxicological effect in the compositions, do not promote the additional agents of infection effect of the chemical compound of formula (I), for example chelating agen yet.A kind of preferred compositions by or form by the chemical compound of formula (I) and component such as the solvent of non-activity (for example water and/or alcohol), coloring agent, flavouring agent and sweeting agent substantially.
In a preferred embodiment, the level that contains alcohol in the compound compositions of formula (I) is low, preferably is lower than 25%w/v, more preferably less than 20%w/v, more preferably less than 10%w/v, for example is lower than 5%w/v, 3%w/v or 1%w/v.In another preferred embodiment, contain in the compound compositions of formula (I) and do not have alcohol.The used term " alcohol " of this explanation is meant any alcohol that can be used for oral formulations, preferred alcohol.
The chemical compound of formula (I) can use with suitable concentration, and described concentration is apparent to those skilled in the art.In one embodiment, the debita spissitudo of the chemical compound of formula (I) between 0.01% (w/v) between 10% (w/v), preferably between 0.1% (w/v) between 5% (w/v), more preferably between 1% (w/v) between 3% (w/v), 2% (w/v) for example.The most preferable concentrations of the chemical compound of formula (I) is 0.2% (w/v).
In one embodiment of the invention, every 100kg compositions contains ethanol and the 0.003kg sodium hydroxide of 98.267kg deionized water, 0.2kg hydrochloric acid delmopinol, 0.01kg sodium saccharate, 0.02kg draft flavouring agent COD76634-34,1.5kg 99.5%.
Can the oral cavity with in the short time, preferably carry out mechanical vibration immediately when the chemical compound of formula (I) contacts or after the oral cavity contacts with the chemical compound of formula (I), preferably brush or friction comprise the zone of infected sub-gingival pocket.
The present invention includes a test kit or pack, described test kit or pack contain the chemical compound of formula (I) and the description that the treatment gum infects down, also contain the description that guides user uses described compounds for treating to infect.
The present invention obtains further instruction with reference to following limiting examples.
Embodiment 1
In the present embodiment, use delmopinol to treat the patient who has accepted treatments in 2 years as collutory.She is suffered from Morbus Crohn (crohn) and oral cavity syndrome by diagnosis, and described oral cavity syndrome shows as the serious gingiva damage and the gingiva of swelling.Previously, she has accepted the treatment of antibiotic (Zithromax) to control her oral cavity infection, and she also regularly uses 0.12% chlorhexidine mouthwash solution growing surely again with the control pathogen.Regularly using chlorhexidine is the supplementary means of other oral hygiene measures with control gingival infection/inflammation.But chlorhexidine has side effect, i.e. tooth dyeing, hypogeusia and scorching hot sensation.Alcohol in the chlorhexidine may also can cause some patients' problem.Potential burning sensation is a trouble in this situation, and the patient can not comply with chlorhexidine and gargles.
Changed conventional treatment and allowed her gargle once with 0.2%w/v delmopinol (instead of chlorhexidine) every day in 14 days.She has accepted professional cleaning of teeth but has not left the prescription of systemic antibiotic before using delmopinol to gargle.Before this treatment, used azithromycin 6 months.
Below be clinical findings:
1. in time fortnight, the patient does not report the side effect of dyeing or burning sensation, and described patient reports that to the clinicist she prefers gargling with delmopinol.
2. hemorrhage less when detecting, swelling and aching of gum alleviates and the ulcer disappearance during visual examination, and the degree of described situation proof various focusing depths represented has reduced clinically.
Compare with the sample that extracts before the use delmopinol, in the sample that uses delmopinol to extract after 2 weeks, see, in the sample, total bacterial loads significantly reduces (see figure 1) under the gum of choosing in four selected sub-gingival pockets (periodontal pocket numbering 13,23,37 and 42).
In addition, find that some keystone pathogens reduce.Though porphyromonas gingivalis and Fu Sai stainer bacterium do not reduce, the level of treponema denticola and actinobacillus actinomycetem comitans significantly reduces (in fact actinobacillus actinomycetem comitans has been eliminated).Referring to Fig. 2.
In a word, infect down and as if having superiority with the delmopinol treatment gum of gargling than chlorhexidine.Do not dye and do not have burning sensation to improve compliance gargling.Secondly, gargle with delmopinol and as if microbiota under the gum is had positive role generally.Therefore delmopinol is used in to prevent and treat clinically under the gum and infects.

Claims (14)

1. the morpholine kind compound with general formula (I) or its officinal salt purposes in the medicine of the infected sub-gingival pocket of preparation treatment:
Figure A2006800435270002C1
R wherein 1Be the straight or branched alkyl that contains 8 to 16 carbon atoms that is positioned at morpholine ring 2 or 3, R 2Be the straight or branched alkyl that contains 2 to 10 carbon atoms, described R 2Except that the α position, all replaced by hydroxyl.
2. according to the purposes of claim 1, the radicals R of wherein said morpholine kind compound 1And R 2The summation of middle carbon number is at least 10, preferably between 10 to 20.
3. according to the purposes of claim 1 or 2, the R of wherein said morpholine kind compound 2End has hydroxyl.
4. according to each purposes of aforementioned claim, wherein said morpholine kind compound is 3-(4-propyl group-heptyl)-4-(2-ethoxy) morpholine.
5. according to each purposes of aforementioned claim, wherein said sub-gingival pocket be 4mm deeply or darker.
6. according to each purposes of aforementioned claim, wherein said infected sub-gingival pocket is that the antibacterial complex that is subjected to be defined as red complex in this description infects.
7. according to each purposes of aforementioned claim, wherein said infected sub-gingival pocket contains any one in blissful match stainer bacterium (Tannerella forsythensis), porphyromonas gingivalis (Porphyromonas gingivalis), treponema denticola (Treponema denticola) or the actinobacillus actinomycetem comitans (Actinobacillus actinomycetemcomitans).
8. according to each purposes of aforementioned claim, wherein said gum infects down is characterized as periodontitis.
9. according to each purposes of aforementioned claim, wherein said gum infects down is characterized as chronic periodontitis.
10. according to each purposes of aforementioned claim, also contain a kind of antimicrobial in the wherein said medicine.
11., also contain a kind of antiinflammatory in the wherein said medicine according to each purposes of aforementioned claim.
12. according to each purposes of aforementioned claim, wherein said medicine is an aqueous.
13. according to each purposes of aforementioned claim, the form of wherein said medicine is collutory, toothpaste, gutta-percha or chewing gum.
14. a test kit that is used for the treatment of sub-gingival pocket infections comprises each described chemical compound of claim 1 to 4 and the description of using described compounds for treating to infect.
CNA2006800435276A 2005-11-22 2006-11-22 Treatment of sub-gingival pocket infections Pending CN101312766A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102958566A (en) * 2010-06-30 2013-03-06 高露洁-棕榄公司 Oral health index

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102958566A (en) * 2010-06-30 2013-03-06 高露洁-棕榄公司 Oral health index

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Marder et al. Chemotherapy and periodontal disease—A review
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