CA2094874C - Compositions de tetracycline non-antibacteriennes possedant des proprietes anti-plaque - Google Patents

Compositions de tetracycline non-antibacteriennes possedant des proprietes anti-plaque Download PDF

Info

Publication number: CA2094874C
Authority: CA; Canada
Prior art keywords: tetracycline; antimicrobial; dedimethylaminotetracycline; confection; amount
Prior art date: 1992-04-27
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.): Expired - Fee Related

Application number

CA 2094874

Other languages

English (en)

Other versions

CA2094874A1 (fr

Inventor

Thomas F. Mcnamara

Lorne M. Golub

Nangavarum S. Ramamurthy

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.)

Research Foundation of the State University of New York

Original Assignee

Research Foundation of the State University of New York

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.)

1992-04-27

Filing date

1993-04-26

Publication date

2003-02-11

1993-04-26 Application filed by Research Foundation of the State University of New York filed Critical Research Foundation of the State University of New York

1993-10-28 Publication of CA2094874A1 publication Critical patent/CA2094874A1/fr

2003-02-11 Application granted granted Critical

2003-02-11 Publication of CA2094874C publication Critical patent/CA2094874C/fr

2013-04-26 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004098 Tetracycline Substances 0.000 title claims abstract description 101
235000019364 tetracycline Nutrition 0.000 title claims abstract description 99
150000003522 tetracyclines Chemical class 0.000 title claims abstract description 97
229960002180 tetracycline Drugs 0.000 title claims abstract description 68
229930101283 tetracycline Natural products 0.000 title claims abstract description 66
230000002882 anti-plaque Effects 0.000 title description 3
239000000551 dentifrice Substances 0.000 claims abstract description 6
235000015218 chewing gum Nutrition 0.000 claims abstract description 3
239000007937 lozenge Substances 0.000 claims abstract description 3
230000000845 anti-microbial effect Effects 0.000 claims description 68
235000009508 confectionery Nutrition 0.000 claims description 21
XCCHQGIGHCRZOS-KBKZQPOHSA-N (4as,5as,6s,12ar)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@@](C)(O)[C@@H](C[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)C3)(O)C3=O)C3=C(O)C2=C1O XCCHQGIGHCRZOS-KBKZQPOHSA-N 0.000 claims description 15
208000008655 root caries Diseases 0.000 claims description 14
239000004099 Chlortetracycline Substances 0.000 claims description 5
239000004100 Oxytetracycline Substances 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
229960004475 chlortetracycline Drugs 0.000 claims description 5
229960000625 oxytetracycline Drugs 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
239000002324 mouth wash Substances 0.000 claims description 4
229940051866 mouthwash Drugs 0.000 claims description 4
MWUTTXATIMURBN-VSAOOKSHSA-N (4aS,5aS,6S,12aR)-3,6,10,11-tetrahydroxy-6-methyl-1,12-dioxo-4a,5,5a,12a-tetrahydro-4H-tetracene-2-carboxamide Chemical compound C[C@]1(O)[C@H]2C[C@H]3CC(O)=C(C(N)=O)C(=O)[C@H]3C(=O)C2=C(O)c2c(O)cccc12 MWUTTXATIMURBN-VSAOOKSHSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
229940112822 chewing gum Drugs 0.000 claims 1
229940040944 tetracyclines Drugs 0.000 abstract description 33
208000002925 dental caries Diseases 0.000 abstract description 31
230000007505 plaque formation Effects 0.000 abstract description 17
238000000034 method Methods 0.000 abstract description 16
230000000844 anti-bacterial effect Effects 0.000 abstract description 13
230000002401 inhibitory effect Effects 0.000 abstract description 6
241000700159 Rattus Species 0.000 description 35
206010012601 diabetes mellitus Diseases 0.000 description 22
244000005706 microflora Species 0.000 description 16
230000000694 effects Effects 0.000 description 15
210000004283 incisor Anatomy 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 10
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 10
241000894006 Bacteria Species 0.000 description 8
210000000214 mouth Anatomy 0.000 description 8
210000003298 dental enamel Anatomy 0.000 description 7
239000000243 solution Substances 0.000 description 7
208000002064 Dental Plaque Diseases 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
230000007406 plaque accumulation Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000001580 bacterial effect Effects 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
239000011775 sodium fluoride Substances 0.000 description 5
235000013024 sodium fluoride Nutrition 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
229960003722 doxycycline Drugs 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
235000019634 flavors Nutrition 0.000 description 4
AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
230000002949 hemolytic effect Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
235000012054 meals Nutrition 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
230000002265 prevention Effects 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
239000000176 sodium gluconate Substances 0.000 description 3
235000012207 sodium gluconate Nutrition 0.000 description 3
229940005574 sodium gluconate Drugs 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
241000606125 Bacteroides Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
102000029816 Collagenase Human genes 0.000 description 2
108060005980 Collagenase Proteins 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
208000012868 Overgrowth Diseases 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
238000011203 antimicrobial therapy Methods 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
230000001680 brushing effect Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000003366 colagenolytic effect Effects 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
229960002424 collagenase Drugs 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
238000005115 demineralization Methods 0.000 description 2
230000002328 demineralizing effect Effects 0.000 description 2
210000004268 dentin Anatomy 0.000 description 2
238000011161 development Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
210000004195 gingiva Anatomy 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
208000028169 periodontal disease Diseases 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
229960001052 streptozocin Drugs 0.000 description 2
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
229960004989 tetracycline hydrochloride Drugs 0.000 description 2
NNRXCKZMQLFUPL-WBMZRJHASA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;(2r,3 Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 NNRXCKZMQLFUPL-WBMZRJHASA-N 0.000 description 1
NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 1
PPJYSSNKSXAVDB-UHFFFAOYSA-N 3,3',5,5'-tetraiodothyroacetic acid Chemical compound IC1=CC(CC(=O)O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 PPJYSSNKSXAVDB-UHFFFAOYSA-N 0.000 description 1
RHAXKFFKGZJUOE-UHFFFAOYSA-N 7-acetyl-6-ethyl-3,5,8-trihydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid Chemical compound O=C1C2=CC(O)=C(C(O)=O)C(C(O)=O)=C2C(=O)C2=C1C(O)=C(CC)C(C(C)=O)=C2O RHAXKFFKGZJUOE-UHFFFAOYSA-N 0.000 description 1
241000186046 Actinomyces Species 0.000 description 1
108010011485 Aspartame Proteins 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000186000 Bifidobacterium Species 0.000 description 1
208000006386 Bone Resorption Diseases 0.000 description 1
JUQPZRLQQYSMEQ-UHFFFAOYSA-N CI Basic red 9 Chemical compound [Cl-].C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)=C1C=CC(=[NH2+])C=C1 JUQPZRLQQYSMEQ-UHFFFAOYSA-N 0.000 description 1
241000581364 Clinitrachus argentatus Species 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Natural products O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000186660 Lactobacillus Species 0.000 description 1
241001453171 Leptotrichia Species 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000194019 Streptococcus mutans Species 0.000 description 1
208000008312 Tooth Loss Diseases 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
101710151579 Zinc metalloproteinase Proteins 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
230000035508 accumulation Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
230000000675 anti-caries Effects 0.000 description 1
239000000605 aspartame Substances 0.000 description 1
235000010357 aspartame Nutrition 0.000 description 1
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
229960003438 aspartame Drugs 0.000 description 1
229940052223 basic fuchsin Drugs 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000024279 bone resorption Effects 0.000 description 1
239000004075 cariostatic agent Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
235000021316 daily nutritional intake Nutrition 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
230000001904 diabetogenic effect Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
201000010840 enamel caries Diseases 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
230000008029 eradication Effects 0.000 description 1
229940098008 erythrocin Drugs 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
210000001508 eye Anatomy 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
229960003132 halothane Drugs 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229940039696 lactobacillus Drugs 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229960000282 metronidazole Drugs 0.000 description 1
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000009054 pathological process Effects 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940048109 sodium methyl cocoyl taurate Drugs 0.000 description 1
238000010186 staining Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
210000001258 synovial membrane Anatomy 0.000 description 1
210000002435 tendon Anatomy 0.000 description 1
-1 tetracycline compound Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
210000004746 tooth root Anatomy 0.000 description 1
229940034610 toothpaste Drugs 0.000 description 1
239000000606 toothpaste Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000013022 venting Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1

Landscapes

Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA 2094874 1992-04-27 1993-04-26 Compositions de tetracycline non-antibacteriennes possedant des proprietes anti-plaque Expired - Fee Related CA2094874C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US87436992A	1992-04-27	1992-04-27
US874,369		1992-04-27

Publications (2)

Publication Number	Publication Date
CA2094874A1 CA2094874A1 (fr)	1993-10-28
CA2094874C true CA2094874C (fr)	2003-02-11

Family

ID=25363587

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2094874 Expired - Fee Related CA2094874C (fr)	1992-04-27	1993-04-26	Compositions de tetracycline non-antibacteriennes possedant des proprietes anti-plaque

Country Status (2)

Country	Link
AU (1)	AU665249B2 (fr)
CA (1)	CA2094874C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT102160B (pt) *	1998-05-26	2001-04-30	Hovione Sociedade Quimica S A	Processo para a preparacao de 4-(des-dimetilamino)-tetraciclinas

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4704383A (en) *	1983-12-29	1987-11-03	The Research Foundation Of State University Of New York	Non-antibacterial tetracycline compositions possessing anti-collagenolytic properties and methods of preparing and using same

1993
- 1993-04-26 CA CA 2094874 patent/CA2094874C/fr not_active Expired - Fee Related
- 1993-04-27 AU AU38201/93A patent/AU665249B2/en not_active Ceased

Also Published As

Publication number	Publication date
CA2094874A1 (fr)	1993-10-28
AU3820193A (en)	1993-10-28
AU665249B2 (en)	1995-12-21

Legal Events

Date	Code	Title	Description
2000-01-05	EEER	Examination request
2007-04-26	MKLA	Lapsed

Publication	Publication Date	Title
CA2103801C (fr)	2002-11-19	Compositions non antibacteriennes a base de tetracyclines ayant des prorietes anti-plaque dentaire
US5770588A (en)	1998-06-23	Non-antibacterial tetracycline compositions of the prevention and treatment of root caries
US5104644A (en)	1992-04-14	Mouthrinse composition
US4883534A (en)	1989-11-28	Benzoin antimicrobial dental varnishes
US4664906A (en)	1987-05-12	Oral compositions
EP0128655B1 (fr)	1991-01-23	Vernis dentaires antimicrobiens contenant de la benzoine
Prasanna et al.	2016	Characteristics, uses and side effects of chlorhexidine-A review
CA1126163A (fr)	1982-06-22	Compose antimicrobien en administration orale
US4661342A (en)	1987-04-28	Oral compositions comprising hydroxamic acids and salts thereof
JPS6216923B2 (fr)	1987-04-15
CA2094874C (fr)	2003-02-11	Compositions de tetracycline non-antibacteriennes possedant des proprietes anti-plaque
US5827503A (en)	1998-10-27	Method and composition for treating periodontitis
US5500206A (en)	1996-03-19	Oral compositions comprising actinomyces viscosus fimbriae
KR100230710B1 (ko)	1999-11-15	잇몸질환의 예방 및 치료용 조성물
Ciancio	1980	Chemotherapeutics in periodontics
US4965262A (en)	1990-10-23	Method for treating or preventing locally periodontal disease
AU2011309832B2 (en)	2015-01-15	Antimicrobial dental care preparation
CA2547654A1 (fr)	2005-06-16	Utilisation de l'osteopontine dans des preparations dentaires
WO1990010434A1 (fr)	1990-09-20	Preparation dentaire
JPH1059832A (ja)	1998-03-03	口腔用抗菌剤及び口腔用組成物
WO1991015189A1 (fr)	1991-10-17	Procede et composition servant a prevenir les stomatites chez les utilisateurs de dentiers
JPH0560444B2 (fr)	1993-09-02
KR20220122137A (ko)	2022-09-02	아세트산을 포함하는 구강질환 예방 또는 치료용 조성물
Chung et al.	2000	Inhibition of Plaque Formation on the Titanium Surface by Anti-bacterial Varnish
Bercy et al.	1994	Effectiveness of Bromochlorophene on Gingival Health