JP2008531479A5 - - Google Patents
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- JP2008531479A5 JP2008531479A5 JP2007553252A JP2007553252A JP2008531479A5 JP 2008531479 A5 JP2008531479 A5 JP 2008531479A5 JP 2007553252 A JP2007553252 A JP 2007553252A JP 2007553252 A JP2007553252 A JP 2007553252A JP 2008531479 A5 JP2008531479 A5 JP 2008531479A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- chloro
- amino
- group
- hydrogen
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- -1 N-chloroaminoethylphosphonic acid diester Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 8
- VAUDXPRANUFYEC-UHFFFAOYSA-N 2-(chloroamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(NCl)CCCP(O)(O)=O VAUDXPRANUFYEC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 4
- DQSLXKNCNPPTSN-UHFFFAOYSA-N 1-(chloroamino)propylphosphonic acid Chemical compound CCC(NCl)P(O)(O)=O DQSLXKNCNPPTSN-UHFFFAOYSA-N 0.000 claims description 3
- XIGJZYVHLIRSFU-UHFFFAOYSA-N 2-(bromoamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(NBr)CCCP(O)(O)=O XIGJZYVHLIRSFU-UHFFFAOYSA-N 0.000 claims description 3
- KBINJLBTMJFAPH-UHFFFAOYSA-N 2-(chloroamino)-2-methylpropane-1-sulfonic acid Chemical compound ClNC(C)(C)CS(O)(=O)=O KBINJLBTMJFAPH-UHFFFAOYSA-N 0.000 claims description 3
- SCFWQPHRDQRQIW-UHFFFAOYSA-N 2-(chloroamino)-8-phosphonooctanoic acid Chemical compound OC(=O)C(NCl)CCCCCCP(O)(O)=O SCFWQPHRDQRQIW-UHFFFAOYSA-N 0.000 claims description 3
- BASCKKRUKJKATL-UHFFFAOYSA-N CC(C)C(NCl)P(O)(O)=O Chemical compound CC(C)C(NCl)P(O)(O)=O BASCKKRUKJKATL-UHFFFAOYSA-N 0.000 claims description 3
- DARKVQOMVNRQNZ-JEDNCBNOSA-N OBO.CC(C)C[C@H](NCl)C(O)=O Chemical compound OBO.CC(C)C[C@H](NCl)C(O)=O DARKVQOMVNRQNZ-JEDNCBNOSA-N 0.000 claims description 3
- 235000004279 alanine Nutrition 0.000 claims description 3
- BCRSJKZAODSYFK-UHFFFAOYSA-N 2-(chloroamino)-3-phosphonopropanoic acid Chemical compound OC(=O)C(NCl)CP(O)(O)=O BCRSJKZAODSYFK-UHFFFAOYSA-N 0.000 claims description 2
- IPWWLXWYFSGQFM-UHFFFAOYSA-N 2-(chloroamino)propane-1-sulfonic acid Chemical compound ClNC(C)CS(O)(=O)=O IPWWLXWYFSGQFM-UHFFFAOYSA-N 0.000 claims description 2
- GDVDLFHXJBBZOE-UHFFFAOYSA-N 3-(chloroamino)-2,2,3-trimethylbutanoic acid Chemical compound ClNC(C)(C)C(C)(C)C(O)=O GDVDLFHXJBBZOE-UHFFFAOYSA-N 0.000 claims description 2
- CEWZMYBSKUHYMS-UHFFFAOYSA-N 4-(chloroamino)-4-phosphonobutanoic acid Chemical compound OC(=O)CCC(NCl)P(O)(O)=O CEWZMYBSKUHYMS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 208000015181 infectious disease Diseases 0.000 claims 5
- 239000004599 antimicrobial Substances 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229940121375 antifungal agent Drugs 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 244000052769 pathogen Species 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 206010052428 Wound Diseases 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 230000000844 anti-bacterial effect Effects 0.000 claims 2
- 239000003429 antifungal agent Substances 0.000 claims 2
- 229960005475 antiinfective agent Drugs 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 239000003899 bactericide agent Substances 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 238000005202 decontamination Methods 0.000 claims 2
- 230000003588 decontaminative effect Effects 0.000 claims 2
- 239000000645 desinfectant Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 235000013305 food Nutrition 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 230000007774 longterm Effects 0.000 claims 2
- 230000003330 sporicidal effect Effects 0.000 claims 2
- 238000004659 sterilization and disinfection Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 230000017423 tissue regeneration Effects 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 230000000843 anti-fungal effect Effects 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- QYNRGGHZWCUZLK-UHFFFAOYSA-N 2-(dichloroamino)-2-methylpropane-1-sulfonic acid Chemical compound ClN(Cl)C(C)(C)CS(O)(=O)=O QYNRGGHZWCUZLK-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- DRNNATGSBCVJBN-UHFFFAOYSA-N 2-amino-2-methylpropane-1-sulfonic acid Chemical compound CC(C)(N)CS(O)(=O)=O DRNNATGSBCVJBN-UHFFFAOYSA-N 0.000 description 5
- VOROEQBFPPIACJ-UHFFFAOYSA-N 5-Phosphononorvaline Chemical compound OC(=O)C(N)CCCP(O)(O)=O VOROEQBFPPIACJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- COIDHHVBAVTJFV-UHFFFAOYSA-N 2-(dichloroamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(N(Cl)Cl)CCCP(O)(O)=O COIDHHVBAVTJFV-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 229940000635 beta-alanine Drugs 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
- DGSLPJDIFKVSIB-UHFFFAOYSA-N (1-azaniumyl-2-methylpropyl)-hydroxyphosphinate Chemical compound CC(C)C(N)P(O)(O)=O DGSLPJDIFKVSIB-UHFFFAOYSA-N 0.000 description 2
- YIBKSASUZFBMOU-UHFFFAOYSA-N 1-(dichloroamino)propane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)CN(Cl)Cl YIBKSASUZFBMOU-UHFFFAOYSA-N 0.000 description 2
- DELJNDWGTWHHFA-UHFFFAOYSA-N 1-azaniumylpropyl(hydroxy)phosphinate Chemical compound CCC(N)P(O)(O)=O DELJNDWGTWHHFA-UHFFFAOYSA-N 0.000 description 2
- BAUYKXPDNLWGGL-UHFFFAOYSA-N 2-(chloroamino)propan-2-ylphosphonic acid Chemical compound ClNC(C)(C)P(O)(O)=O BAUYKXPDNLWGGL-UHFFFAOYSA-N 0.000 description 2
- JJQITYDTBUXIDS-UHFFFAOYSA-N 2-(dibromoamino)-2-methylpropane-1-sulfonic acid Chemical compound BrN(Br)C(C)(C)CS(O)(=O)=O JJQITYDTBUXIDS-UHFFFAOYSA-N 0.000 description 2
- IHEFYJCAHPMNNZ-UHFFFAOYSA-N 2-(dichloroamino)-8-phosphonooctanoic acid Chemical compound OC(=O)C(N(Cl)Cl)CCCCCCP(O)(O)=O IHEFYJCAHPMNNZ-UHFFFAOYSA-N 0.000 description 2
- LDSLVJUAHMPZBB-UHFFFAOYSA-N 2-(diiodoamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(I)I LDSLVJUAHMPZBB-UHFFFAOYSA-N 0.000 description 2
- XUGMGYUIGNYMJQ-UHFFFAOYSA-N 2-(iodoamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNI XUGMGYUIGNYMJQ-UHFFFAOYSA-N 0.000 description 2
- IAZCXYBRDWVPNV-UHFFFAOYSA-N 2-amino-3-methyl-3-sulfobutanoic acid Chemical compound OS(=O)(=O)C(C)(C)C(N)C(O)=O IAZCXYBRDWVPNV-UHFFFAOYSA-N 0.000 description 2
- LBTABPSJONFLPO-UHFFFAOYSA-N 2-amino-3-phosphonopropanoic acid Chemical compound OC(=O)C(N)CP(O)(O)=O LBTABPSJONFLPO-UHFFFAOYSA-N 0.000 description 2
- DYGRPJWAYXRMQZ-UHFFFAOYSA-N 2-aminopropan-2-ylphosphonic acid Chemical compound CC(C)(N)P(O)(O)=O DYGRPJWAYXRMQZ-UHFFFAOYSA-N 0.000 description 2
- NETIXPOFUYPXNI-UHFFFAOYSA-N 2-aminopropane-2-sulfonic acid Chemical compound CC(C)(N)S(O)(=O)=O NETIXPOFUYPXNI-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- OXIWSCWSIBBUDO-UHFFFAOYSA-N 3-(dichloroamino)-2,2,3-trimethylbutanoic acid Chemical compound ClN(Cl)C(C)(C)C(C)(C)C(O)=O OXIWSCWSIBBUDO-UHFFFAOYSA-N 0.000 description 2
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 2
- DWYLYZGWBIVRGV-UHFFFAOYSA-N 4-(dichloroamino)-4-phosphonobutanoic acid Chemical compound OC(=O)CCC(N(Cl)Cl)P(O)(O)=O DWYLYZGWBIVRGV-UHFFFAOYSA-N 0.000 description 2
- SODXFOVXZATGPJ-UHFFFAOYSA-N 4-amino-4-phosphonobutanoic acid Chemical compound OP(=O)(O)C(N)CCC(O)=O SODXFOVXZATGPJ-UHFFFAOYSA-N 0.000 description 2
- OPIXQPCOZBIRMY-UHFFFAOYSA-N CC(C)CC(N)(C(O)=O)P(O)(O)=O Chemical compound CC(C)CC(N)(C(O)=O)P(O)(O)=O OPIXQPCOZBIRMY-UHFFFAOYSA-N 0.000 description 2
- 241001135569 Human adenovirus 5 Species 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- YKTCVYHHAFHLHL-JEDNCBNOSA-N OBO.CC(C)C[C@H](N(Cl)Cl)C(O)=O Chemical compound OBO.CC(C)C[C@H](N(Cl)Cl)C(O)=O YKTCVYHHAFHLHL-JEDNCBNOSA-N 0.000 description 2
- KXCDENIMXRKIPT-UHFFFAOYSA-N OBO.OC(=O)CCNCl Chemical compound OBO.OC(=O)CCNCl KXCDENIMXRKIPT-UHFFFAOYSA-N 0.000 description 2
- GBUDGXDEROGHBY-JEDNCBNOSA-N OP(O)=O.CC(C)C[C@H](N(Cl)Cl)C(O)=O Chemical compound OP(O)=O.CC(C)C[C@H](N(Cl)Cl)C(O)=O GBUDGXDEROGHBY-JEDNCBNOSA-N 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- LDCBEAIUZPYSBX-JEDNCBNOSA-N P(O)(O)=O.ClN[C@@H](CC(C)C)C(=O)O Chemical compound P(O)(O)=O.ClN[C@@H](CC(C)C)C(=O)O LDCBEAIUZPYSBX-JEDNCBNOSA-N 0.000 description 2
- UEQTVRUQHVQHSW-UHFFFAOYSA-N [1-(dichloroamino)-2-methylpropyl]phosphonic acid Chemical compound CC(C)C(N(Cl)Cl)P(O)(O)=O UEQTVRUQHVQHSW-UHFFFAOYSA-N 0.000 description 2
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 239000013580 millipore water Substances 0.000 description 2
- 229960003104 ornithine Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- MEGHVKHOSRPKFB-REOHCLBHSA-N (2s)-2-(dichloroamino)propanoic acid Chemical compound ClN(Cl)[C@@H](C)C(O)=O MEGHVKHOSRPKFB-REOHCLBHSA-N 0.000 description 1
- QUOIXMXPWCACSF-UHFFFAOYSA-N 1-(dichloroamino)propylphosphonic acid Chemical compound CCC(N(Cl)Cl)P(O)(O)=O QUOIXMXPWCACSF-UHFFFAOYSA-N 0.000 description 1
- ZFJWYAYBWZHPGT-UHFFFAOYSA-N 1-amino-2-methylpropane-2-sulfonic acid Chemical compound NCC(C)(C)S(O)(=O)=O ZFJWYAYBWZHPGT-UHFFFAOYSA-N 0.000 description 1
- GBYFFQSMDBOMCX-UHFFFAOYSA-N 2-(dibromoamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(N(Br)Br)CCCP(O)(O)=O GBYFFQSMDBOMCX-UHFFFAOYSA-N 0.000 description 1
- YDRDBSJEDQYEFJ-UHFFFAOYSA-N 2-(dichloroamino)-3-phosphonopropanoic acid Chemical compound OC(=O)C(N(Cl)Cl)CP(O)(O)=O YDRDBSJEDQYEFJ-UHFFFAOYSA-N 0.000 description 1
- FWACYDHVHFBQHS-UHFFFAOYSA-N 2-(dichloroamino)propan-2-ylphosphonic acid Chemical compound ClN(Cl)C(C)(C)P(O)(O)=O FWACYDHVHFBQHS-UHFFFAOYSA-N 0.000 description 1
- WYRXPDKKQWTPKX-UHFFFAOYSA-N 2-(dichloroamino)propane-1-sulfonic acid Chemical compound ClN(Cl)C(C)CS(O)(=O)=O WYRXPDKKQWTPKX-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- KGGCRFYWXLVUQQ-UHFFFAOYSA-N 2-amino-8-phosphonooctanoic acid Chemical compound OC(=O)C(N)CCCCCCP(O)(O)=O KGGCRFYWXLVUQQ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- YFXICVBBMRYJMK-UHFFFAOYSA-N OBO.NCCC(O)=O Chemical compound OBO.NCCC(O)=O YFXICVBBMRYJMK-UHFFFAOYSA-N 0.000 description 1
- DXDZUCBULNMIIX-UHFFFAOYSA-N OBO.OC(=O)CCN(Cl)Cl Chemical compound OBO.OC(=O)CCN(Cl)Cl DXDZUCBULNMIIX-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- BMGMQYRPZOGZFU-YFKPBYRVSA-N [(1r)-1-amino-3-methylbutyl]boronic acid Chemical compound CC(C)C[C@H](N)B(O)O BMGMQYRPZOGZFU-YFKPBYRVSA-N 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- YMDXZJFXQJVXBF-STHAYSLISA-N fosfomycin Chemical class C[C@@H]1O[C@@H]1P(O)(O)=O YMDXZJFXQJVXBF-STHAYSLISA-N 0.000 description 1
- 229960000308 fosfomycin Drugs 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000003328 mesylation reaction Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64736605P | 2005-01-25 | 2005-01-25 | |
| US60/647,366 | 2005-01-25 | ||
| PCT/US2006/002875 WO2006081392A1 (en) | 2005-01-25 | 2006-01-25 | N-halogenated amino acids and n, n-dihalogenated amino acids in combination with hypohalous acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008531479A JP2008531479A (ja) | 2008-08-14 |
| JP2008531479A5 true JP2008531479A5 (OSRAM) | 2009-03-05 |
| JP5329095B2 JP5329095B2 (ja) | 2013-10-30 |
Family
ID=36441417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007553252A Expired - Fee Related JP5329095B2 (ja) | 2005-01-25 | 2006-01-25 | 次亜ハロゲン酸と組み合わせる、ｎ−ハロゲン化アミノ酸およびｎ，ｎ−ジハロゲン化アミノ酸 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7846971B2 (OSRAM) |
| EP (1) | EP1896001B1 (OSRAM) |
| JP (1) | JP5329095B2 (OSRAM) |
| KR (1) | KR20070098947A (OSRAM) |
| CN (1) | CN101132785A (OSRAM) |
| AU (1) | AU2006208046B2 (OSRAM) |
| BR (1) | BRPI0607302A2 (OSRAM) |
| CA (1) | CA2595889C (OSRAM) |
| ES (1) | ES2421157T3 (OSRAM) |
| IL (1) | IL184771A (OSRAM) |
| MX (1) | MX2007008928A (OSRAM) |
| TW (1) | TWI386201B (OSRAM) |
| WO (1) | WO2006081392A1 (OSRAM) |
| ZA (1) | ZA200706402B (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ545654A (en) | 2003-08-18 | 2009-12-24 | Novabay Pharmaceuticals Inc | N,N-dihalogenated amino acids and derivatives |
| US8747882B2 (en) * | 2005-04-21 | 2014-06-10 | Astra Tech Ab | Catheter assembly with bactericidal effect |
| CA2623576A1 (en) * | 2005-09-21 | 2007-03-29 | Novabay Pharmaceuticals, Inc. | System and method for the prevention and treatment of bacterial and fungal infections including urinary tract infections (uti) using a hypohalous acid compositions |
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-
2006
- 2006-01-24 TW TW095102567A patent/TWI386201B/zh not_active IP Right Cessation
- 2006-01-25 AU AU2006208046A patent/AU2006208046B2/en not_active Ceased
- 2006-01-25 CN CNA2006800070563A patent/CN101132785A/zh active Pending
- 2006-01-25 US US11/339,987 patent/US7846971B2/en active Active
- 2006-01-25 CA CA2595889A patent/CA2595889C/en not_active Expired - Fee Related
- 2006-01-25 BR BRPI0607302-6A patent/BRPI0607302A2/pt not_active Application Discontinuation
- 2006-01-25 WO PCT/US2006/002875 patent/WO2006081392A1/en not_active Ceased
- 2006-01-25 MX MX2007008928A patent/MX2007008928A/es active IP Right Grant
- 2006-01-25 ES ES06733945T patent/ES2421157T3/es not_active Expired - Lifetime
- 2006-01-25 KR KR1020077019438A patent/KR20070098947A/ko not_active Ceased
- 2006-01-25 EP EP06733945.7A patent/EP1896001B1/en not_active Expired - Lifetime
- 2006-01-25 JP JP2007553252A patent/JP5329095B2/ja not_active Expired - Fee Related
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2007
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