CA1072009A - Medicaments potentialises contenant des agents antimicrobiens - Google Patents

Medicaments potentialises contenant des agents antimicrobiens

Info

Publication number: CA1072009A
Authority: CA; Canada
Prior art keywords: cyclohexyl; group; propanol; potentiator; composition
Prior art date: 1976-11-12
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

Application number

CA265,435A

Other languages

English (en)

Inventor

Tibor Sipos

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.)

Johnson and Johnson

Original Assignee

Johnson and Johnson

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.)

1976-11-12

Filing date

1976-11-12

Publication date

1980-02-19

1976-11-12 Application filed by Johnson and Johnson filed Critical Johnson and Johnson

1976-11-12 Priority to CA265,435A priority Critical patent/CA1072009A/fr

1980-02-19 Application granted granted Critical

1980-02-19 Publication of CA1072009A publication Critical patent/CA1072009A/fr

Status Expired legal-status Critical Current

Links

239000004599 antimicrobial Substances 0.000 title claims abstract description 51
239000003814 drug Substances 0.000 title claims description 15
239000000203 mixture Substances 0.000 claims abstract description 83
230000000845 anti-microbial effect Effects 0.000 claims abstract description 31
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 15
150000001298 alcohols Chemical class 0.000 claims abstract description 12
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 8
239000003242 anti bacterial agent Substances 0.000 claims abstract description 7
229940121375 antifungal agent Drugs 0.000 claims abstract description 7
239000003429 antifungal agent Substances 0.000 claims abstract description 7
MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 claims abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
229940088710 antibiotic agent Drugs 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 5
239000004094 surface-active agent Substances 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
230000002421 anti-septic effect Effects 0.000 claims abstract description 4
229940064004 antiseptic throat preparations Drugs 0.000 claims abstract description 4
150000002989 phenols Chemical class 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 71
230000000699 topical effect Effects 0.000 claims description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 18
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 16
239000003193 general anesthetic agent Substances 0.000 claims description 16
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
-1 aliphatic alcohols Chemical class 0.000 claims description 14
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
229960000629 domiphen Drugs 0.000 claims description 9
YXUPZGKORWTXID-UHFFFAOYSA-N domiphen Chemical compound CCCCCCCCCCCC[N+](C)(C)CCOC1=CC=CC=C1 YXUPZGKORWTXID-UHFFFAOYSA-N 0.000 claims description 9
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 8
CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 claims description 8
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound 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 claims description 8
RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 claims description 8
DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 8
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 8
229960001859 domiphen bromide Drugs 0.000 claims description 8
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 8
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 8
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 7
229930193140 Neomycin Natural products 0.000 claims description 7
229960004927 neomycin Drugs 0.000 claims description 7
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical group OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 claims description 6
YVBCULSIZWMTFY-UHFFFAOYSA-N 4-Heptanol Natural products CCCC(O)CCC YVBCULSIZWMTFY-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 6
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
229960005274 benzocaine Drugs 0.000 claims description 6
229960004194 lidocaine Drugs 0.000 claims description 6
230000003389 potentiating effect Effects 0.000 claims description 6
BFKOEFFCVFMWPF-UHFFFAOYSA-N 2,3-dimethylhexan-2-ol Chemical compound CCCC(C)C(C)(C)O BFKOEFFCVFMWPF-UHFFFAOYSA-N 0.000 claims description 5
239000004098 Tetracycline Substances 0.000 claims description 5
229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 claims description 5
INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
229960002180 tetracycline Drugs 0.000 claims description 5
229930101283 tetracycline Natural products 0.000 claims description 5
235000019364 tetracycline Nutrition 0.000 claims description 5
150000003522 tetracyclines Chemical class 0.000 claims description 5
NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 4
QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 claims description 4
IRIVQXLOJHCXIE-UHFFFAOYSA-N 2-cyclohexylpropan-1-ol Chemical compound OCC(C)C1CCCCC1 IRIVQXLOJHCXIE-UHFFFAOYSA-N 0.000 claims description 4
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
KFVBFLFHJJMEPR-UHFFFAOYSA-N 3-cyclohexyl-2-methylbutan-1-ol Chemical compound OCC(C)C(C)C1CCCCC1 KFVBFLFHJJMEPR-UHFFFAOYSA-N 0.000 claims description 4
IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 claims description 4
UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 claims description 4
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 4
239000004100 Oxytetracycline Substances 0.000 claims description 4
239000000443 aerosol Substances 0.000 claims description 4
QQOBRRFOVWGIMD-OJAKKHQRSA-N azaribine Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=N1 QQOBRRFOVWGIMD-OJAKKHQRSA-N 0.000 claims description 4
229950010054 azaribine Drugs 0.000 claims description 4
229940105270 carbocaine Drugs 0.000 claims description 4
239000006071 cream Substances 0.000 claims description 4
229960001378 dequalinium chloride Drugs 0.000 claims description 4
LTNZEXKYNRNOGT-UHFFFAOYSA-N dequalinium chloride Chemical compound [Cl-].[Cl-].C1=CC=C2[N+](CCCCCCCCCC[N+]3=C4C=CC=CC4=C(N)C=C3C)=C(C)C=C(N)C2=C1 LTNZEXKYNRNOGT-UHFFFAOYSA-N 0.000 claims description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
229960003276 erythromycin Drugs 0.000 claims description 4
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 4
DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 4
229960002867 griseofulvin Drugs 0.000 claims description 4
229940049018 mycostatin Drugs 0.000 claims description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 4
125000002524 organometallic group Chemical group 0.000 claims description 4
229960000625 oxytetracycline Drugs 0.000 claims description 4
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims description 4
235000019366 oxytetracycline Nutrition 0.000 claims description 4
229960005322 streptomycin Drugs 0.000 claims description 4
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims description 4
JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 claims description 3
WYTRYIUQUDTGSX-UHFFFAOYSA-N 1-phenylpropan-2-ol Chemical compound CC(O)CC1=CC=CC=C1 WYTRYIUQUDTGSX-UHFFFAOYSA-N 0.000 claims description 3
JPUIYNHIEXIFMV-UHFFFAOYSA-N 2,5-dimethylhexan-2-ol Chemical compound CC(C)CCC(C)(C)O JPUIYNHIEXIFMV-UHFFFAOYSA-N 0.000 claims description 3
YVJDFHXFDFYOME-UHFFFAOYSA-N 2-(4-propan-2-ylcyclohexyl)propan-2-ol Chemical compound CC(C)C1CCC(C(C)(C)O)CC1 YVJDFHXFDFYOME-UHFFFAOYSA-N 0.000 claims description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 3
SSZWOQANOUHNLV-UHFFFAOYSA-N 2-cyclohexylpropan-2-ol Chemical compound CC(C)(O)C1CCCCC1 SSZWOQANOUHNLV-UHFFFAOYSA-N 0.000 claims description 3
RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 claims description 3
LTZKHYYXQWNXPU-UHFFFAOYSA-N 2-methyl-3-phenylpropan-1-ol Chemical compound OCC(C)CC1=CC=CC=C1 LTZKHYYXQWNXPU-UHFFFAOYSA-N 0.000 claims description 3
RGRUUTLDBCWYBL-UHFFFAOYSA-N 2-methylhexan-3-ol Chemical compound CCCC(O)C(C)C RGRUUTLDBCWYBL-UHFFFAOYSA-N 0.000 claims description 3
ICLIXBRUSBYXEV-ZBFHGGJFSA-N 3-[(4ar,7as)-2,3,4,4a,5,6,7,7a-octahydrocyclopenta[b]pyridin-1-yl]-n-(2-chloro-6-methylphenyl)propanamide Chemical compound CC1=CC=CC(Cl)=C1NC(=O)CCN1[C@H]2CCC[C@@H]2CCC1 ICLIXBRUSBYXEV-ZBFHGGJFSA-N 0.000 claims description 3
FROCGBFQIWUEGD-UHFFFAOYSA-N 3-cyclohexyl-2-methylpropan-1-ol Chemical compound OCC(C)CC1CCCCC1 FROCGBFQIWUEGD-UHFFFAOYSA-N 0.000 claims description 3
XHKHXJPTSALKON-UHFFFAOYSA-N 3-cyclohexylbutan-1-ol Chemical compound OCCC(C)C1CCCCC1 XHKHXJPTSALKON-UHFFFAOYSA-N 0.000 claims description 3
CLYAQFSQLQTVNO-UHFFFAOYSA-N 3-cyclohexylpropan-1-ol Chemical compound OCCCC1CCCCC1 CLYAQFSQLQTVNO-UHFFFAOYSA-N 0.000 claims description 3
ZBLQQRZVKHLRBF-UHFFFAOYSA-N 4-cyclohexylbutan-2-ol Chemical compound CC(O)CCC1CCCCC1 ZBLQQRZVKHLRBF-UHFFFAOYSA-N 0.000 claims description 3
108010001478 Bacitracin Proteins 0.000 claims description 3
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 claims description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 3
229960003071 bacitracin Drugs 0.000 claims description 3
229930184125 bacitracin Natural products 0.000 claims description 3
CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 claims description 3
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 3
229960001927 cetylpyridinium chloride Drugs 0.000 claims description 3
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 3
229940097572 chloromycetin Drugs 0.000 claims description 3
CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims description 3
CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=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)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims description 3
ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical group OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
229960000318 kanamycin Drugs 0.000 claims description 3
229930027917 kanamycin Natural products 0.000 claims description 3
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 3
229930182823 kanamycin A Natural products 0.000 claims description 3
239000006210 lotion Substances 0.000 claims description 3
229960002509 miconazole Drugs 0.000 claims description 3
VGEBLZDDRJDVDP-RRKRAGSPSA-N n-demethylrifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H](C(OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC2=C(O)C=3C(O)=C4C)C)OC)C4=C1C=3C(=O)\C2=C\NN1CCNCC1 VGEBLZDDRJDVDP-RRKRAGSPSA-N 0.000 claims description 3
230000001105 regulatory effect Effects 0.000 claims description 3
229960001225 rifampicin Drugs 0.000 claims description 3
JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims description 3
229960002372 tetracaine Drugs 0.000 claims description 3
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims description 3
229940043810 zinc pyrithione Drugs 0.000 claims description 3
PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims description 3
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NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229940074928 isopropyl myristate Drugs 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
229940063718 lodine Drugs 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229960002409 mepivacaine Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA265,435A 1976-11-12 1976-11-12 Medicaments potentialises contenant des agents antimicrobiens Expired CA1072009A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA265,435A CA1072009A (fr)	1976-11-12	1976-11-12	Medicaments potentialises contenant des agents antimicrobiens

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA265,435A CA1072009A (fr)	1976-11-12	1976-11-12	Medicaments potentialises contenant des agents antimicrobiens

Publications (1)

Publication Number	Publication Date
CA1072009A true CA1072009A (fr)	1980-02-19

Family

ID=4107245

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA265,435A Expired CA1072009A (fr)	1976-11-12	1976-11-12	Medicaments potentialises contenant des agents antimicrobiens

Country Status (1)

Country	Link
CA (1)	CA1072009A (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0129284A2 (fr)	1983-06-21	1984-12-27	THE PROCTER & GAMBLE COMPANY	Compositions pharmaceutiques topiques à pénétration améliorée contenant de la 1-dodécyl-azacycloheptan-2-one
US4537776A (en) *	1983-06-21	1985-08-27	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing N-(2-hydroxyethyl) pyrrolidone
US4552872A (en) *	1983-06-21	1985-11-12	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing corticosteroids
US4663077A (en) *	1984-06-11	1987-05-05	Morton Thiokol Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4683080A (en) *	1984-06-11	1987-07-28	Morton Thiokol, Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4711914A (en) *	1985-04-22	1987-12-08	Morton Thiokol, Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4895877A (en) *	1984-06-11	1990-01-23	Morton Thiokol, Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4954487A (en) *	1979-01-08	1990-09-04	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions
WO2005018585A1 (fr) *	2003-08-25	2005-03-03	Bioequal Ag	Formulations pharmaceutiques et cosmetiques pour le traitement des ongles

1976
- 1976-11-12 CA CA265,435A patent/CA1072009A/fr not_active Expired

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4954487A (en) *	1979-01-08	1990-09-04	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions
EP0129284A2 (fr)	1983-06-21	1984-12-27	THE PROCTER & GAMBLE COMPANY	Compositions pharmaceutiques topiques à pénétration améliorée contenant de la 1-dodécyl-azacycloheptan-2-one
US4537776A (en) *	1983-06-21	1985-08-27	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing N-(2-hydroxyethyl) pyrrolidone
US4552872A (en) *	1983-06-21	1985-11-12	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing corticosteroids
US4557934A (en) *	1983-06-21	1985-12-10	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one
US4663077A (en) *	1984-06-11	1987-05-05	Morton Thiokol Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4683080A (en) *	1984-06-11	1987-07-28	Morton Thiokol, Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4895877A (en) *	1984-06-11	1990-01-23	Morton Thiokol, Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4711914A (en) *	1985-04-22	1987-12-08	Morton Thiokol, Inc.	Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
WO2005018585A1 (fr) *	2003-08-25	2005-03-03	Bioequal Ag	Formulations pharmaceutiques et cosmetiques pour le traitement des ongles
AU2004266053B2 (en) *	2003-08-25	2011-06-09	Bioequal Ag	Pharmaceutical and cosmetic formulations for treating fingernails

Legal Events

Date	Code	Title	Description
1997-02-19	MKEX	Expiry

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US4197318A (en)	1980-04-08	Potentiated antimicrobial medicaments
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