JP2015131821A - 抗菌性ビグアニド金属錯体 - Google Patents
抗菌性ビグアニド金属錯体 Download PDFInfo
- Publication number
- JP2015131821A JP2015131821A JP2015031988A JP2015031988A JP2015131821A JP 2015131821 A JP2015131821 A JP 2015131821A JP 2015031988 A JP2015031988 A JP 2015031988A JP 2015031988 A JP2015031988 A JP 2015031988A JP 2015131821 A JP2015131821 A JP 2015131821A
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- Prior art keywords
- silver
- biguanide
- compounds
- iii
- compositions
- 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.)
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- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 33
- 239000002184 metal Substances 0.000 title claims abstract description 33
- 229940123208 Biguanide Drugs 0.000 title description 39
- 230000000845 anti-microbial effect Effects 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000003446 ligand Substances 0.000 claims abstract description 40
- 230000003647 oxidation Effects 0.000 claims abstract description 21
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 abstract description 25
- 230000000813 microbial effect Effects 0.000 abstract description 17
- QWWUPSPHPYNVRP-UHFFFAOYSA-N [Ag+3] Chemical class [Ag+3] QWWUPSPHPYNVRP-UHFFFAOYSA-N 0.000 abstract description 16
- 208000015181 infectious disease Diseases 0.000 abstract description 16
- 238000011282 treatment Methods 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 10
- 230000001590 oxidative effect Effects 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 8
- 150000002736 metal compounds Chemical class 0.000 abstract description 6
- 229920002635 polyurethane Polymers 0.000 abstract description 6
- 239000004814 polyurethane Substances 0.000 abstract description 6
- 239000000758 substrate Substances 0.000 abstract description 5
- 230000001580 bacterial effect Effects 0.000 abstract 2
- 238000011321 prophylaxis Methods 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 229910052709 silver Inorganic materials 0.000 description 23
- 239000004332 silver Substances 0.000 description 23
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 21
- -1 silver halide Chemical class 0.000 description 20
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 20
- 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 17
- 150000004283 biguanides Chemical class 0.000 description 17
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 description 15
- 208000035143 Bacterial infection Diseases 0.000 description 14
- 208000022362 bacterial infectious disease Diseases 0.000 description 14
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 230000002265 prevention Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 229960003260 chlorhexidine Drugs 0.000 description 9
- 229910001961 silver nitrate Inorganic materials 0.000 description 9
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 9
- 241000894007 species Species 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 229910021645 metal ion Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229910001923 silver oxide Inorganic materials 0.000 description 8
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 description 7
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical class [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 7
- 206010052428 Wound Diseases 0.000 description 7
- 208000027418 Wounds and injury Diseases 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 6
- 229940100890 silver compound Drugs 0.000 description 6
- 150000003379 silver compounds Chemical class 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 239000000017 hydrogel Substances 0.000 description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 150000002500 ions Chemical group 0.000 description 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 3
- 229910000367 silver sulfate Inorganic materials 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 208000002847 Surgical Wound Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 229960004111 buformin Drugs 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- CBMIPXHVOVTTTL-UHFFFAOYSA-N gold(3+) Chemical compound [Au+3] CBMIPXHVOVTTTL-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229960003243 phenformin Drugs 0.000 description 2
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 description 2
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver;carbonate Chemical compound [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- VBICEVQOHHQRLY-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,3-dichlorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=CC(Cl)=C1Cl VBICEVQOHHQRLY-UHFFFAOYSA-N 0.000 description 1
- AKYXEMYENQTFQJ-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,4-difluorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(F)C=C1F AKYXEMYENQTFQJ-UHFFFAOYSA-N 0.000 description 1
- ISWYMEZLJNBVDA-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,5-dichlorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=CC(Cl)=CC=C1Cl ISWYMEZLJNBVDA-UHFFFAOYSA-N 0.000 description 1
- PZXIBLJRRIQYKP-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,6-dichlorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=C(Cl)C=CC=C1Cl PZXIBLJRRIQYKP-UHFFFAOYSA-N 0.000 description 1
- YSUCWSWKRIOILX-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-phenylethyl)guanidine;hydrochloride Chemical compound Cl.NC(N)=NC(N)=NCCC1=CC=CC=C1 YSUCWSWKRIOILX-UHFFFAOYSA-N 0.000 description 1
- NOLAUIXZGNESCX-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(4-fluorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(F)C=C1 NOLAUIXZGNESCX-UHFFFAOYSA-N 0.000 description 1
- BRGJGAOPCRWLMM-UHFFFAOYSA-N 1-(diaminomethylidene)-2-[4-(trifluoromethoxy)phenyl]guanidine Chemical class NC(N)=NC(N)=NC1=CC=C(OC(F)(F)F)C=C1 BRGJGAOPCRWLMM-UHFFFAOYSA-N 0.000 description 1
- YBEYVQONJZSGFJ-UHFFFAOYSA-N 1-(diaminomethylidene)-2-[4-(trifluoromethyl)phenyl]guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(C(F)(F)F)C=C1 YBEYVQONJZSGFJ-UHFFFAOYSA-N 0.000 description 1
- MKWFJPZMYHPQIA-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1Cl MKWFJPZMYHPQIA-UHFFFAOYSA-N 0.000 description 1
- WEVBBIBQCXPDKL-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(F)C(Cl)=C1 WEVBBIBQCXPDKL-UHFFFAOYSA-N 0.000 description 1
- ZVDJMZRPCBCFRP-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZVDJMZRPCBCFRP-UHFFFAOYSA-N 0.000 description 1
- USGCMNLQYSXCDU-UHFFFAOYSA-N 2-cyclohexyl-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1CCCCC1 USGCMNLQYSXCDU-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
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- RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 description 1
- RILOPSTZZRJOQI-UHFFFAOYSA-N 4-cyclohexylbutanoic acid;silver Chemical compound [Ag].OC(=O)CCCC1CCCCC1 RILOPSTZZRJOQI-UHFFFAOYSA-N 0.000 description 1
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- MRALEFCGSMITEY-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(=N)NC(=N)N.ClC1=CC=C(C=C1)NC(=N)NC(=N)N Chemical compound ClC1=CC=C(C=C1)NC(=N)NC(=N)N.ClC1=CC=C(C=C1)NC(=N)NC(=N)N MRALEFCGSMITEY-UHFFFAOYSA-N 0.000 description 1
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- DIHXJZHAIHGSAW-UHFFFAOYSA-N m-Chlorophenylbiguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC(Cl)=C1 DIHXJZHAIHGSAW-UHFFFAOYSA-N 0.000 description 1
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- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- DTPQZKZONQKKSU-UHFFFAOYSA-N silver azanide silver Chemical compound [NH2-].[Ag].[Ag].[Ag+] DTPQZKZONQKKSU-UHFFFAOYSA-N 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229940071575 silver citrate Drugs 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 description 1
- 229940019931 silver phosphate Drugs 0.000 description 1
- 229910000161 silver phosphate Inorganic materials 0.000 description 1
- 229960003600 silver sulfadiazine Drugs 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- RHUVFRWZKMEWNS-UHFFFAOYSA-M silver thiocyanate Chemical compound [Ag+].[S-]C#N RHUVFRWZKMEWNS-UHFFFAOYSA-M 0.000 description 1
- CHACQUSVOVNARW-LNKPDPKZSA-M silver;(z)-4-oxopent-2-en-2-olate Chemical compound [Ag+].C\C([O-])=C\C(C)=O CHACQUSVOVNARW-LNKPDPKZSA-M 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- QUTYHQJYVDNJJA-UHFFFAOYSA-K trisilver;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Ag+].[Ag+].[Ag+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QUTYHQJYVDNJJA-UHFFFAOYSA-K 0.000 description 1
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- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
- C07C279/265—X and Y being nitrogen atoms, i.e. biguanides containing two or more biguanide groups
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- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
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Abstract
【解決手段】金属種および生物学的に許容される配位子を含む化合物であって、生物学的に許容される配位子がビグアニド部分を含み、生物学的に許容される配位子が金属種と錯体を形成し、金属種が1+を上回る酸化状態で安定化されている化合物。この化合物を含む組成物および医療デバイス。このような化合物、組成物または医療デバイスの使用を含む、細菌感染を含む微生物感染の治療または予防のための方法。
【選択図】なし
Description
本発明の別の目的は、このような組成物またはデバイスで使用するためにこのような化合物の一部を提供することである。
ハロ、例えばクロロまたはフルオロによってフェニル基において任意選択で置換されたフェニル直鎖および分岐鎖C1〜6のアルキル、例えばフェネチル、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルキル、例えばメチル、例えばトリフルオロメチル、C5〜8のシクロアルキル、例えばシクロヘキシル、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルコキシル、例えばメトキシルおよびエトキシル、例えばトリフルオロメトキシル、C5〜8のシクロアルキル、例えばシクロヘキシル、ならびに/あるいはニトロなど、アリール基において任意選択で置換されたヘテロ芳香脂肪族ヒドロカルビル基を含む芳香脂肪族ヒドロカルビル基、
クロロやフルオロなどのハロによってフェニル基において任意選択で置換されたヘテロ芳香族ヒドロカルビル基、例えば、フェニル、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルキル、例えばメチル、例えばトリフルオロメチル、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルコキシル、例えばメトキシルまたはエトキシル、例えばトリフルオロメトキシル、ならびに/あるいはC5〜8のシクロアルキル、例えばシクロヘキシル、ならびに/あるいはニトロを含む任意選択で置換された芳香族ヒドロカルビル基が含まれる。
ハロ、例えばクロロまたはフルオロによってフェニレン基において任意選択で置換されたフェニレンC1〜6の直鎖および分岐鎖アルキレン、例えば1,4-フェニレンエタンジ-1,2-イルまたは1,4-ジメタンジイルベンゼン、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルキル、例えばメチル、例えばトリフルオロメチル、C5〜8のシクロアルキル、例えばシクロヘキシル、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルコキシル、例えばメトキシルおよびエトキシル、例えばトリフルオロメトキシル、C5〜8のシクロアルキル、例えばシクロヘキシル、ならびに/あるいはニトロなど、アリーレン基において任意選択で置換されたヘテロ芳香脂肪族ヒドロカルバジイル基を含む芳香脂肪族ヒドロカルバジイル基、
クロロやフルオロなどのハロによってフェニレン基において任意選択で置換されたヘテロ芳香族ヒドロカルバジイル基、例えばフェニレン、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルキル、例えばメチル、例えばトリフルオロメチル、ハロ、例えばクロロまたはフルオロによって任意選択で置換されたC1〜6のアルコキシル、例えばメトキシルまたはエトキシル、例えばトリフルオロメトキシル、ならびに/あるいはC5〜8のシクロアルキル、例えばシクロヘキシル、ならびに/あるいはニトロを含む任意選択で置換された芳香族ヒドロカルビル基が含まれる。
クロルヘキシジン(1,1'-ヘキサメチレンビス[5-(p-クロロフェニル)ビグアニド]と、硝酸銀と、過硫酸ナトリウムとの組合せ、
PHMBと、硝酸銀と、過硫酸ナトリウムとの組合せ、および
o-トリルビグアニドと、硫酸銀と、過硫酸ナトリウムとの組合せを含む。
クロルヘキシジン(1,1'-ヘキサメチレンビス[5-(p-クロロフェニル)ビグアニド](1.00g)を100mlの温かいメタノールに溶解させた。この撹拌した溶液に、5mlの蒸留水中で作製した硝酸銀(0.34g)の水溶液を滴下添加した。この後、5mlの蒸留水中で作製した過硫酸ナトリウム(0.94g)の水溶液を滴下した。この反応混合物を、橙褐色が十分に発現するまで温めた。沈殿物を真空下でブフナー(Buchner)ろ過し、温かいメタノールで3回洗浄し、周囲温度および周囲圧力で保存した。
PHMB(0.400g)を50mlのメタノールに溶解させた。この撹拌した溶液に、2mlの蒸留水中で作製した硝酸銀(0.185g)の水溶液を滴下添加した。この後、2mlの蒸留水中で作製した過硫酸ナトリウム(0.520g)の水溶液を滴下した。この反応混合物を、橙褐色が十分に発現するまで撹拌した。
o-トリルビグアニド(1.00g)を50mlのメタノールに溶解させた。この撹拌した溶液に、5mlの蒸留水中で作製した硝酸銀(0.44g)の水溶液を滴下添加した。この後、5mlの蒸留水中で作製した過硫酸ナトリウム(1.25g)の水溶液を滴下した。
Profore WCL (Smith & Nephew Medical Ltd)の5cm2の見本を、o-トリルビグアニドのメタノール溶液(50mg/ml)に5秒間浸した。この見本を取り出し、熱風銃を用いて温風乾燥した。硝酸銀水溶液(10mg/ml)に10秒間見本を浸漬し、取り出し、過剰な蒸留水ですすいだ。次いで、温めた過硫酸ナトリウム水溶液(10mg/ml)に、橙色が十分に発現するまで(約15秒)見本を浸漬した。見本を取り出し、過剰な蒸留水中ですすぎ、周囲温度および周囲圧力で保存するために風乾した。
5mgの銀(III)クロルヘキシジン錯体(実施例1)を、3gのIntraSite Gel (Smith & Nephew Medical Ltd)に機械的に混合することによって分散させた。24時間後、安定で均一に橙色のヒドロゲルが形成された。
5mgの銀(III)PHMB錯体(実施例2)を、3gのIntraSite Gel (Smith & Nephew Medical Ltd)に機械的に混合することによって分散させた。24時間後、安定で均一に橙色のヒドロゲルが形成された。
実施例5および6で調製したゲル調合物を、同様に調製した(3gのIntraSite Gel当たり5mgの銀種)代替銀源の調合物と比較した。代替銀源は、硝酸銀、炭酸銀、塩化銀、臭化銀、ヨウ化銀、酸化銀(I)(Ag2O)および酸化銀(I, III) (AgO)であった。各調合物を、24時間にわたる観察のために無菌の透明なプラスチック管(Sterilin Ltd)内に設置した。
緑膿菌(Pseudomonas aeruginosa)NCIMB 8626および黄色ブドウ球菌(Staphylococcus aureus)NCTC 10788を採取した。連続的な1:10希釈を行って、108細菌/mlの最終濃度を得た。接種数に向けて、10-8細菌/mlまでさらなる希釈を行った。1ml当たりの細菌の数(細菌/ml)は混釈平板法を用いて決定した。
Claims (1)
- 金属種および生物学的に許容される配位子を含む化合物であって、前記生物学的に許容される配位子がビグアニド部分を含み、前記生物学的に許容される配位子が前記金属種と錯体を形成し、前記金属種が1+を上回る酸化状態で安定化されている化合物。
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JP2017165760A (ja) * | 2005-06-27 | 2017-09-21 | スミス アンド ネフュー ピーエルシーSmith & Nephew Public Limited Company | 抗菌性ビグアニド金属錯体 |
JP2018012816A (ja) * | 2016-07-22 | 2018-01-25 | ライオン株式会社 | 浴室用洗浄剤組成物 |
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WO2007000590A8 (en) | 2008-05-02 |
JP6424111B2 (ja) | 2018-11-14 |
AU2006263606A1 (en) | 2007-01-04 |
KR101410587B1 (ko) | 2014-06-23 |
KR20140033248A (ko) | 2014-03-17 |
US20090123513A1 (en) | 2009-05-14 |
CA2613005A1 (en) | 2007-01-04 |
ZA200800070B (en) | 2010-12-29 |
CA2613005C (en) | 2017-01-17 |
WO2007000590A1 (en) | 2007-01-04 |
EP1902059B1 (en) | 2016-12-21 |
US9751833B2 (en) | 2017-09-05 |
JP2017165760A (ja) | 2017-09-21 |
ES2619630T3 (es) | 2017-06-26 |
KR20080021133A (ko) | 2008-03-06 |
EP1902059A1 (en) | 2008-03-26 |
JP2013075901A (ja) | 2013-04-25 |
JP2008546832A (ja) | 2008-12-25 |
AU2006263606B2 (en) | 2013-01-31 |
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