FI65063C - Nya piperidinderivat foer anvaendning som munvaordsmedel - Google Patents
Nya piperidinderivat foer anvaendning som munvaordsmedel Download PDFInfo
- Publication number
- FI65063C FI65063C FI770776A FI770776A FI65063C FI 65063 C FI65063 C FI 65063C FI 770776 A FI770776 A FI 770776A FI 770776 A FI770776 A FI 770776A FI 65063 C FI65063 C FI 65063C
- Authority
- FI
- Finland
- Prior art keywords
- compounds
- plaque
- nya
- piperidinderivat
- munvaordsmedel
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003053 piperidines Chemical class 0.000 claims description 5
- -1 dioxo-substituted piperidine Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 239000008375 oral care agent Substances 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 208000002064 Dental Plaque Diseases 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 210000000214 mouth Anatomy 0.000 description 5
- 230000007505 plaque formation Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000002882 anti-plaque Effects 0.000 description 4
- 208000002925 dental caries Diseases 0.000 description 4
- 239000000606 toothpaste Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 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
- 229930091371 Fructose Natural products 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000014151 Stomatognathic disease Diseases 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 229940112822 chewing gum Drugs 0.000 description 2
- 235000015218 chewing gum Nutrition 0.000 description 2
- 229960003260 chlorhexidine Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 210000003296 saliva Anatomy 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 229940034610 toothpaste Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical class CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- DBHODFSFBXJZNY-UHFFFAOYSA-N 2,4-dichlorobenzyl alcohol Chemical compound OCC1=CC=C(Cl)C=C1Cl DBHODFSFBXJZNY-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UWIMQALGFGLTLQ-UHFFFAOYSA-N 3-(3-hydroxypropyl)-3-azaspiro[5.11]heptadecane-2,4-dione Chemical compound C1C(=O)N(CCCO)C(=O)CC21CCCCCCCCCCC2 UWIMQALGFGLTLQ-UHFFFAOYSA-N 0.000 description 1
- GAWZVLXYYUOWSC-UHFFFAOYSA-N 3-azaspiro[5.11]heptadecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC21CCCCCCCCCCC2 GAWZVLXYYUOWSC-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 208000018035 Dental disease Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 102000045595 Phosphoprotein Phosphatases Human genes 0.000 description 1
- 108700019535 Phosphoprotein Phosphatases Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000194019 Streptococcus mutans Species 0.000 description 1
- 208000004509 Tooth Discoloration Diseases 0.000 description 1
- 208000008312 Tooth Loss Diseases 0.000 description 1
- 206010044032 Tooth discolouration Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- CKGWFZQGEQJZIL-UHFFFAOYSA-N amylmetacresol Chemical compound CCCCCC1=CC=C(C)C=C1O CKGWFZQGEQJZIL-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229940068682 chewable tablet Drugs 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- HWTXXVIQAIETAZ-UHFFFAOYSA-K dicalcium urea phosphate Chemical compound NC(=O)N.P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2] HWTXXVIQAIETAZ-UHFFFAOYSA-K 0.000 description 1
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000010794 food waste Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940041678 oral spray Drugs 0.000 description 1
- 239000000668 oral spray Substances 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000036367 tooth discoloration Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- 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
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10977/76A GB1524325A (en) | 1976-03-18 | 1976-03-18 | Piperidine derivatives |
| GB1097776 | 1976-03-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI770776A FI770776A (xx) | 1977-09-19 |
| FI65063B FI65063B (fi) | 1983-11-30 |
| FI65063C true FI65063C (fi) | 1984-03-12 |
Family
ID=9977805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI770776A FI65063C (fi) | 1976-03-18 | 1977-03-10 | Nya piperidinderivat foer anvaendning som munvaordsmedel |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4119711A (xx) |
| JP (1) | JPS52113978A (xx) |
| AT (1) | AT357159B (xx) |
| AU (1) | AU511267B2 (xx) |
| BE (1) | BE852578A (xx) |
| CA (1) | CA1100505A (xx) |
| CH (1) | CH631345A5 (xx) |
| DE (1) | DE2711087A1 (xx) |
| DK (1) | DK155307C (xx) |
| ES (1) | ES456987A1 (xx) |
| FI (1) | FI65063C (xx) |
| FR (1) | FR2344539A1 (xx) |
| GB (1) | GB1524325A (xx) |
| IT (1) | IT1075428B (xx) |
| NL (1) | NL179650C (xx) |
| NO (1) | NO145789C (xx) |
| NZ (1) | NZ183582A (xx) |
| SE (1) | SE431091B (xx) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357471A (en) | 1976-12-17 | 1982-11-02 | Rohm And Haas Company | Azaspiro compounds |
| US4400512A (en) * | 1976-12-17 | 1983-08-23 | Rohm And Haas Company | Azaspiro compounds |
| US4374991A (en) | 1976-12-17 | 1983-02-22 | Rohm And Haas Company | 2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea |
| SE439011B (sv) * | 1980-03-21 | 1985-05-28 | Ferrosan Ab | Morfolinoforeningar, kompositioner innehallande dessa och anvendning derav |
| US4405630A (en) * | 1980-12-29 | 1983-09-20 | Rohm And Haas Company | Arthropod repellent compositions and methods |
| US5082653A (en) * | 1990-10-31 | 1992-01-21 | Warner-Lambert Company | Anti-plaque compositions comprising a combination of morpholinoamino alcohol and antibiotic |
| US5147632A (en) * | 1990-10-31 | 1992-09-15 | Warner-Lambert Company | Anti-plaque compositions comprising a combination of morpholinoamino alcohol and chelating agent |
| US6610276B2 (en) | 2001-01-12 | 2003-08-26 | Steven A. Melman | Multi-functional dental composition |
| US8298516B2 (en) * | 2006-12-22 | 2012-10-30 | Douglas Anderson | Calculus dissolving dental composition and methods for using same |
| US11723852B2 (en) | 2011-10-31 | 2023-08-15 | Kane Biotech Inc. | Antimicrobial-antibiofilm compositions and methods of use thereof for personal care products |
| US11090366B2 (en) | 2011-10-31 | 2021-08-17 | Kane Biotech Inc. | Compositions and methods for reducing oral biofilm |
| PL3160234T3 (pl) | 2014-06-27 | 2022-02-21 | Kane Biotech Inc. | Kompozycie do stosowania w profilaktyce i leczeniu wzrostu biofilmu na oczach, na rękach lub stopach |
| WO2017106467A1 (en) | 2015-12-15 | 2017-06-22 | Gontarz John A | Oral care formulation and method for the removal of tartar and plaque from teeth |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3256277A (en) * | 1966-06-14 | Azaspiro alkanes | ||
| US3256276A (en) * | 1961-02-17 | 1966-06-14 | Geschickter Fund Med Res | Substituted spiroimides |
| US3432499A (en) * | 1965-04-02 | 1969-03-11 | Geschickter Fund Med Res | Trifluoromethylazaspiranes and azaspirane diones |
-
1976
- 1976-03-18 GB GB10977/76A patent/GB1524325A/en not_active Expired
-
1977
- 1977-03-10 FI FI770776A patent/FI65063C/fi not_active IP Right Cessation
- 1977-03-11 AU AU23192/77A patent/AU511267B2/en not_active Expired
- 1977-03-11 US US05/776,903 patent/US4119711A/en not_active Expired - Lifetime
- 1977-03-14 DE DE19772711087 patent/DE2711087A1/de active Granted
- 1977-03-14 NZ NZ183582A patent/NZ183582A/xx unknown
- 1977-03-15 FR FR7707658A patent/FR2344539A1/fr active Granted
- 1977-03-17 BE BE175878A patent/BE852578A/xx not_active IP Right Cessation
- 1977-03-17 CH CH335277A patent/CH631345A5/de not_active IP Right Cessation
- 1977-03-17 IT IT21353/77A patent/IT1075428B/it active
- 1977-03-17 SE SE7703083A patent/SE431091B/xx not_active IP Right Cessation
- 1977-03-17 CA CA274,192A patent/CA1100505A/en not_active Expired
- 1977-03-17 DK DK117677A patent/DK155307C/da not_active IP Right Cessation
- 1977-03-17 AT AT182577A patent/AT357159B/de not_active IP Right Cessation
- 1977-03-17 JP JP2972977A patent/JPS52113978A/ja active Granted
- 1977-03-17 NO NO77770957A patent/NO145789C/no unknown
- 1977-03-17 NL NLAANVRAGE7702897,A patent/NL179650C/xx not_active IP Right Cessation
- 1977-03-18 ES ES456987A patent/ES456987A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1075428B (it) | 1985-04-22 |
| DE2711087A1 (de) | 1977-09-22 |
| FI65063B (fi) | 1983-11-30 |
| BE852578A (fr) | 1977-07-18 |
| SE7703083L (sv) | 1977-09-19 |
| DK117677A (da) | 1977-09-19 |
| NO145789B (no) | 1982-02-22 |
| NL7702897A (nl) | 1977-09-20 |
| FR2344539A1 (fr) | 1977-10-14 |
| AU511267B2 (en) | 1980-08-07 |
| CA1100505A (en) | 1981-05-05 |
| AT357159B (de) | 1980-06-25 |
| JPS5744671B2 (xx) | 1982-09-22 |
| ES456987A1 (es) | 1978-02-16 |
| NL179650C (nl) | 1986-10-16 |
| FR2344539B1 (xx) | 1979-06-22 |
| ATA182577A (de) | 1979-11-15 |
| SE431091B (sv) | 1984-01-16 |
| FI770776A (xx) | 1977-09-19 |
| JPS52113978A (en) | 1977-09-24 |
| CH631345A5 (de) | 1982-08-13 |
| DK155307B (da) | 1989-03-28 |
| AU2319277A (en) | 1978-09-14 |
| NO770957L (no) | 1977-09-20 |
| NZ183582A (en) | 1978-07-28 |
| DE2711087C2 (xx) | 1991-06-06 |
| NO145789C (no) | 1982-06-02 |
| US4119711A (en) | 1978-10-10 |
| GB1524325A (en) | 1978-09-13 |
| DK155307C (da) | 1989-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: AB FERROSAN |