DE69937059T2 - Antibiotische oder antiparasitäre zusammenstellungen aus anionischen oder kationischen dendrimeren - Google Patents
Antibiotische oder antiparasitäre zusammenstellungen aus anionischen oder kationischen dendrimeren Download PDFInfo
- Publication number
- DE69937059T2 DE69937059T2 DE69937059T DE69937059T DE69937059T2 DE 69937059 T2 DE69937059 T2 DE 69937059T2 DE 69937059 T DE69937059 T DE 69937059T DE 69937059 T DE69937059 T DE 69937059T DE 69937059 T2 DE69937059 T2 DE 69937059T2
- Authority
- DE
- Germany
- Prior art keywords
- terminated dendrimers
- dendrimer
- acid
- dendrimers
- solution
- 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.)
- Expired - Lifetime
Links
- 239000000412 dendrimer Substances 0.000 title claims abstract description 208
- 239000000203 mixture Substances 0.000 title description 68
- 230000002141 anti-parasite Effects 0.000 title description 2
- 239000003096 antiparasitic agent Substances 0.000 title description 2
- 230000003115 biocidal effect Effects 0.000 title 1
- 229920000736 dendritic polymer Polymers 0.000 claims abstract description 207
- 125000000129 anionic group Chemical group 0.000 claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 230000003071 parasitic effect Effects 0.000 claims abstract description 14
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims abstract description 10
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims abstract description 9
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 230000001580 bacterial effect Effects 0.000 claims abstract description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 3
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- 229920000962 poly(amidoamine) Polymers 0.000 claims description 174
- -1 2-sulfoethyl Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000002091 cationic group Chemical group 0.000 claims description 15
- 230000005764 inhibitory process Effects 0.000 claims description 11
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 7
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- 229940079593 drug Drugs 0.000 claims description 7
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
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- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000000909 amidinium group Chemical group 0.000 claims description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229920000333 poly(propyleneimine) Polymers 0.000 claims description 3
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 claims description 2
- BCFOOQRXUXKJCL-UHFFFAOYSA-N 4-amino-4-oxo-2-sulfobutanoic acid Chemical compound NC(=O)CC(C(O)=O)S(O)(=O)=O BCFOOQRXUXKJCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003916 ethylene diamine group Chemical group 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- CERZMXAJYMMUDR-QBTAGHCHSA-N 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Chemical compound N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO CERZMXAJYMMUDR-QBTAGHCHSA-N 0.000 claims 2
- OOEZTTCJYIGGPQ-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl] dihydrogen phosphate Chemical compound NC(=S)NC1=CC=C(OP(O)(O)=O)C=C1 OOEZTTCJYIGGPQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- VHHHYFRIANJFAT-UHFFFAOYSA-N 5-(carbamothioylamino)benzene-1,3-dicarboxylic acid Chemical compound NC(=S)NC1=CC(C(O)=O)=CC(C(O)=O)=C1 VHHHYFRIANJFAT-UHFFFAOYSA-N 0.000 claims 1
- MSMXAJVUGSDTNQ-UHFFFAOYSA-N [4-(carbamothioylamino)-7-phosphononaphthalen-1-yl]phosphonic acid Chemical compound OP(=O)(O)C1=CC=C2C(NC(=S)N)=CC=C(P(O)(O)=O)C2=C1 MSMXAJVUGSDTNQ-UHFFFAOYSA-N 0.000 claims 1
- JDFHYYZTUNBHCA-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]methylphosphonic acid Chemical compound NC(=S)NC1=CC=C(CP(O)(O)=O)C=C1 JDFHYYZTUNBHCA-UHFFFAOYSA-N 0.000 claims 1
- GDBQRUMLUQFAPB-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]phosphonic acid Chemical compound NC(=S)NC1=CC=C(P(O)(O)=O)C=C1 GDBQRUMLUQFAPB-UHFFFAOYSA-N 0.000 claims 1
- JRROFPKPQONCSD-UHFFFAOYSA-N [4-[carbamothioyl(ethyl)amino]phenyl]methylphosphonic acid Chemical compound CCN(C(N)=S)C1=CC=C(CP(O)(O)=O)C=C1 JRROFPKPQONCSD-UHFFFAOYSA-N 0.000 claims 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 abstract description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract description 2
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- 150000002016 disaccharides Chemical class 0.000 abstract 1
- 150000002482 oligosaccharides Polymers 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 198
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 145
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
- 239000007787 solid Substances 0.000 description 96
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 238000002360 preparation method Methods 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- 238000002523 gelfiltration Methods 0.000 description 41
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- 239000011734 sodium Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
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- 238000005481 NMR spectroscopy Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
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- 0 CC(Ns1ccc(*)cc1)=S Chemical compound CC(Ns1ccc(*)cc1)=S 0.000 description 14
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- 210000003743 erythrocyte Anatomy 0.000 description 14
- 244000045947 parasite Species 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 230000012010 growth Effects 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 238000004108 freeze drying Methods 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
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- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 8
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- DMXCRDDZLQVVPL-UHFFFAOYSA-N 2-[(4-amino-4-oxobutanoyl)amino]ethanesulfonic acid;sodium Chemical compound [Na].NC(=O)CCC(=O)NCCS(O)(=O)=O DMXCRDDZLQVVPL-UHFFFAOYSA-N 0.000 description 6
- BCYXJQPCUFSMMK-UHFFFAOYSA-N 4-(carbamothioylamino)naphthalene-2,7-disulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=C2C(NC(=S)N)=CC(S(O)(=O)=O)=CC2=C1 BCYXJQPCUFSMMK-UHFFFAOYSA-N 0.000 description 6
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- IAHXTXSDUKSVCL-UHFFFAOYSA-N [4-[carbamothioyl(ethyl)amino]phenyl]methylphosphonic acid;sodium Chemical compound [Na].CCN(C(N)=S)C1=CC=C(CP(O)(O)=O)C=C1 IAHXTXSDUKSVCL-UHFFFAOYSA-N 0.000 description 1
- NOHGBDNLMMVZPY-UHFFFAOYSA-N [Na].CCC1=CC(CP(O)(O)=O)=CC=C1N=C=S Chemical compound [Na].CCC1=CC(CP(O)(O)=O)=CC=C1N=C=S NOHGBDNLMMVZPY-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 150000008064 anhydrides Chemical class 0.000 description 1
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- 239000006286 aqueous extract Substances 0.000 description 1
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- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- WPCXDBCEDWUSOU-UHFFFAOYSA-N benzoyl iodide Chemical compound IC(=O)C1=CC=CC=C1 WPCXDBCEDWUSOU-UHFFFAOYSA-N 0.000 description 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- BNNQNALSLWKHIV-UHFFFAOYSA-N butanoic acid;1-hydroxypyrrolidine-2,5-dione Chemical compound CCCC(O)=O.ON1C(=O)CCC1=O BNNQNALSLWKHIV-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- DOMNIPGGSWBJPW-UHFFFAOYSA-N dodecanoyl bromide pyridine Chemical compound C1=CC=NC=C1.CCCCCCCCCCCC(Br)=O DOMNIPGGSWBJPW-UHFFFAOYSA-N 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000009650 gentamicin protection assay Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 235000020130 leben Nutrition 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical class NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 231100000255 pathogenic effect Toxicity 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- VYQLXFDWYFQLHL-UHFFFAOYSA-M potassium;2-thiophen-2-ylacetate Chemical compound [K+].[O-]C(=O)CC1=CC=CS1 VYQLXFDWYFQLHL-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000005629 sialic acid group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/04—Amoebicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/16—Dendrimers and dendritic polymers
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPP5842A AUPP584298A0 (en) | 1998-09-14 | 1998-09-14 | Antimicrobial and antiparasitic agents |
| AUPP584298 | 1998-09-14 | ||
| PCT/AU1999/000763 WO2000015240A1 (en) | 1998-09-14 | 1999-09-13 | Anionic or cationic dendrimer antimicrobial or antiparasitic compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69937059D1 DE69937059D1 (de) | 2007-10-18 |
| DE69937059T2 true DE69937059T2 (de) | 2008-05-29 |
Family
ID=3810064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69937059T Expired - Lifetime DE69937059T2 (de) | 1998-09-14 | 1999-09-13 | Antibiotische oder antiparasitäre zusammenstellungen aus anionischen oder kationischen dendrimeren |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6464971B1 (https=) |
| EP (1) | EP1113806B1 (https=) |
| JP (1) | JP4979848B2 (https=) |
| KR (1) | KR100720905B1 (https=) |
| CN (2) | CN101352451A (https=) |
| AT (1) | ATE372123T1 (https=) |
| AU (1) | AUPP584298A0 (https=) |
| BR (1) | BR9913712A (https=) |
| CA (1) | CA2343113C (https=) |
| DE (1) | DE69937059T2 (https=) |
| NZ (1) | NZ510289A (https=) |
| WO (1) | WO2000015240A1 (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7572459B2 (en) * | 1998-09-14 | 2009-08-11 | Starpharma Pty Ltd. | Anionic or cationic dendrimer antimicrobial or antiparasitic compositions |
| KR100413532B1 (ko) * | 2001-02-14 | 2003-12-31 | 학교법인 포항공과대학교 | 폴리아민이 말단에 치환된 덴드리머 및 그 제조방법 |
| AUPR412901A0 (en) * | 2001-03-30 | 2001-05-03 | Starpharma Limited | Agents for the prevention and treatment of sexually transmitted disease s - II |
| AUPR412801A0 (en) * | 2001-03-30 | 2001-05-03 | Starpharma Limited | Agent for the prevention and treatment of sexually transmitted disease s - I |
| WO2003049772A2 (en) * | 2001-12-11 | 2003-06-19 | The Board Of Trustees Of The Leland Stanford Junior University | Guanidinium transport reagents and conjugates |
| AU2003256038A1 (en) * | 2002-08-30 | 2004-03-19 | Ramot At Tel Aviv University Ltd. | Self-immolative dendrimers releasing many active moieties upon a single activating event |
| US20040234496A1 (en) * | 2003-02-06 | 2004-11-25 | Stockel Richard F. | Biocidal compositions |
| US7074459B2 (en) * | 2003-05-23 | 2006-07-11 | Stockel Richard F | Method for preserving wood |
| FR2862650B1 (fr) * | 2003-11-24 | 2007-04-20 | Rhodia Cons Spec Ltd | Nouveaux dendrimeres a terminaisons monophosphoniques, leur procede de preparation et leur utilisation |
| FR2862651B1 (fr) * | 2003-11-24 | 2006-03-31 | Rhodia Cons Spec Ltd | Nouveaux dendrimeres a terminaisons bisphosphoniques et derives, leur procede de preparation et leur utilisation |
| CN1296711C (zh) * | 2004-05-14 | 2007-01-24 | 沈阳迈迪生物医学技术有限公司 | 乳腺癌的Her－2免疫组织化学诊断试剂盒 |
| JP4553354B2 (ja) | 2004-10-04 | 2010-09-29 | 正隆 井原 | 抗トリパノソーマ剤 |
| US8790672B2 (en) * | 2005-02-22 | 2014-07-29 | Nina M. Lamba-Kohli | Generation of antimicrobial surfaces using dendrimer biocides |
| US20060269480A1 (en) * | 2005-05-31 | 2006-11-30 | Ramot At Tel Aviv University Ltd. | Multi-triggered self-immolative dendritic compounds |
| WO2007006700A1 (en) * | 2005-07-08 | 2007-01-18 | Janssen Pharmaceutica N.V. | Modified poly(propylene-imine) dendrimers and their use as transfection agents for anionic bioactive factors |
| PL1937284T3 (pl) * | 2005-10-18 | 2016-05-31 | Starpharma Pty Ltd | System podawania kompozycji bakteriobójczego dendymeru |
| WO2007045010A1 (en) * | 2005-10-21 | 2007-04-26 | Starpharma Pty Limited | Inhibitory compounds |
| US8067402B2 (en) * | 2005-12-12 | 2011-11-29 | Allaccem, Inc. | Methods and systems for coating an oral surface |
| JP5989294B2 (ja) | 2006-01-20 | 2016-09-07 | スターファーマ・プロプライエタリー・リミテッドＳｔａｒｐｈａｒｍａ Ｐｔｙ Ｌｔｄ | 修飾高分子 |
| EP1996209B1 (en) * | 2006-03-22 | 2015-11-04 | Starpharma Pty Limited | Contraceptive composition |
| CA2683383C (en) | 2007-02-21 | 2016-01-05 | Allaccem, Incorporated | Bridged polycyclic compound based compositions for the inhibition and amelioration of disease |
| US20080282480A1 (en) * | 2007-05-15 | 2008-11-20 | The Hong Kong Polytechnic University | Multifunction Finishing Liquids Containing Dendrimers and the Application of the Liquids in Textile Finishing |
| WO2009045237A1 (en) * | 2007-05-21 | 2009-04-09 | California Institute Of Technology | Extraction of actinides from mixtures and ores using dendritic macromolecules |
| US8153617B2 (en) * | 2007-08-10 | 2012-04-10 | Allaccem, Inc. | Bridged polycyclic compound based compositions for coating oral surfaces in humans |
| US8188068B2 (en) * | 2007-08-10 | 2012-05-29 | Allaccem, Inc. | Bridged polycyclic compound based compositions for coating oral surfaces in pets |
| US8153618B2 (en) * | 2007-08-10 | 2012-04-10 | Allaccem, Inc. | Bridged polycyclic compound based compositions for topical applications for pets |
| US20090074833A1 (en) * | 2007-08-17 | 2009-03-19 | Whiteford Jeffery A | Bridged polycyclic compound based compositions for controlling bone resorption |
| US20100016270A1 (en) * | 2008-06-20 | 2010-01-21 | Whiteford Jeffery A | Bridged polycyclic compound based compositions for controlling cholesterol levels |
| US20100004218A1 (en) * | 2008-06-20 | 2010-01-07 | Whiteford Jeffery A | Bridged polycyclic compound based compositions for renal therapy |
| US20100008864A1 (en) * | 2008-07-10 | 2010-01-14 | Andreas Meijer | Aromatic multimers |
| US9815712B2 (en) | 2008-10-03 | 2017-11-14 | California Institute Of Technology | High capacity perchlorate-selective resins from hyperbranched macromolecules |
| WO2010040117A2 (en) * | 2008-10-03 | 2010-04-08 | California Institute Of Technology | Extraction of anions from solutions and mixtures using hyperbranched macromolecules |
| US20120101041A1 (en) | 2009-07-01 | 2012-04-26 | Japan Science And Technology Agency | Polyionic dendrimer and hydrogel comprising same |
| JP5212656B2 (ja) * | 2009-09-02 | 2013-06-19 | 日産化学工業株式会社 | イソチオシアナト化合物の製造方法 |
| US8658702B2 (en) | 2009-12-17 | 2014-02-25 | Mamadou Diallo | Soluble anion exchangers from hyperbranched macromolecules |
| CN103179855B (zh) * | 2010-06-30 | 2015-07-08 | 刘慧文 | 抗菌化合物 |
| RU2478106C2 (ru) * | 2010-11-25 | 2013-03-27 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Казанский (Приволжский) Федеральный Университет" (ФГАОУ ВПО КФУ) | СОЕДИНЕНИЯ НА ОСНОВЕ КОМПЛЕКСОВ ГИПЕРРАЗВЕТВЛЕННЫХ ПОЛИМЕРОВ Boltorn H, ОБЛАДАЮЩИЕ АНТИКАНДИДОЗНОЙ АКТИВНОСТЬЮ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| US9102602B2 (en) | 2010-11-29 | 2015-08-11 | Nissan Chemical Industries, Ltd. | Method for producing isothiocyanate compound |
| KR20180126621A (ko) * | 2011-05-16 | 2018-11-27 | 스타파마 피티와이 리미티드 | 세균성 질염의 치료 또는 예방 방법 |
| WO2013074526A2 (en) | 2011-11-15 | 2013-05-23 | Byocoat Enterprises, Inc. | Antimicrobial compositions and methods of use thereof |
| JP6419701B2 (ja) * | 2012-09-13 | 2018-11-07 | スターファーマ・ピーティーワイ・リミテッド | 眼の感染症の治療または予防方法 |
| EP2958429A4 (en) * | 2013-02-20 | 2016-10-05 | Biolog Inc | COMPOSITIONS AND METHODS FOR INACTIVATION AND / OR REDUCTION OF MICROBIAL TOXIN PRODUCTION |
| ES2835382T3 (es) * | 2013-03-15 | 2021-06-22 | Boehringer Ingelheim Animal Health Usa Inc | Composiciones de poliamidas antimicrobianas y tratamiento de la mastitis |
| GB201405660D0 (en) * | 2014-03-28 | 2014-05-14 | Gama Healthcare Ltd | A liquid disinfecting composition |
| CN103999853B (zh) * | 2014-06-11 | 2015-07-22 | 中国农业大学 | 荧光树枝状纳米大分子在制备药物载体中的应用 |
| US9854806B2 (en) | 2015-05-19 | 2018-01-02 | International Business Machines Corporation | Antimicrobial guanidinium and thiouronium functionalized polymers |
| MX379091B (es) * | 2016-04-14 | 2025-03-10 | Boehringer Ingelheim Animal Health Usa Inc | Composiciones de múltiples dosis que contienen un conservador de poliamida antimicrobiana u octenidina. |
| WO2018081861A1 (en) * | 2016-11-02 | 2018-05-11 | The University Of Melbourne | Antimicrobial composition combinations comprising star shaped peptide polymers |
| WO2018081845A1 (en) | 2016-11-02 | 2018-05-11 | The University Of Melbourne | Antibacterial compositions and methods |
| US10953039B2 (en) | 2018-09-27 | 2021-03-23 | International Business Machines Corporation | Utilizing polymers and antibiotics to enhance antimicrobial activity and inhibit antibiotic resistance |
| CN110041523B (zh) * | 2019-04-15 | 2021-04-30 | 同济大学 | 低代树枝状聚赖氨酸类抗菌肽及其制备方法 |
| CN114053392B (zh) * | 2020-07-30 | 2024-06-21 | 广州朗圣药业有限公司 | 新型化合物在制备预防和/或治疗hpv感染的药物中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPM623994A0 (en) * | 1994-06-15 | 1994-07-07 | Biomolecular Research Institute Limited | Antiviral dendrimers |
| US5736533A (en) * | 1995-06-07 | 1998-04-07 | Neose Technologies, Inc. | Bacterial inhibition with an oligosaccharide compound |
| US5658574A (en) | 1995-10-13 | 1997-08-19 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Cleansing compositions with dendrimers as mildness agents |
| DE19624705A1 (de) * | 1996-06-20 | 1998-01-08 | Deutsches Krebsforsch | Dendrimere auf Saccharid-Basis |
| AUPO104496A0 (en) * | 1996-07-17 | 1996-08-08 | Biomolecular Research Institute Limited | Angiogenic inhibitory compounds |
| WO1998026662A1 (en) | 1996-12-19 | 1998-06-25 | The Penn State Research Foundation | Compounds and methods for treating and preventing bacterial and viral disease |
| AUPP584398A0 (en) * | 1998-09-14 | 1998-10-08 | Starpharma Limited | Inhibition of toxic materials or substances |
-
1998
- 1998-09-14 AU AUPP5842A patent/AUPP584298A0/en not_active Abandoned
-
1999
- 1999-09-13 NZ NZ510289A patent/NZ510289A/xx not_active IP Right Cessation
- 1999-09-13 JP JP2000569824A patent/JP4979848B2/ja not_active Expired - Lifetime
- 1999-09-13 DE DE69937059T patent/DE69937059T2/de not_active Expired - Lifetime
- 1999-09-13 EP EP99945773A patent/EP1113806B1/en not_active Expired - Lifetime
- 1999-09-13 CN CNA2008100874448A patent/CN101352451A/zh active Pending
- 1999-09-13 WO PCT/AU1999/000763 patent/WO2000015240A1/en not_active Ceased
- 1999-09-13 KR KR1020017003211A patent/KR100720905B1/ko not_active Expired - Lifetime
- 1999-09-13 AT AT99945773T patent/ATE372123T1/de not_active IP Right Cessation
- 1999-09-13 CN CN99812270A patent/CN1323214A/zh active Pending
- 1999-09-13 US US09/786,913 patent/US6464971B1/en not_active Expired - Lifetime
- 1999-09-13 BR BR9913712-7A patent/BR9913712A/pt not_active Application Discontinuation
- 1999-09-13 CA CA002343113A patent/CA2343113C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000015240A1 (en) | 2000-03-23 |
| DE69937059D1 (de) | 2007-10-18 |
| CA2343113A1 (en) | 2000-03-23 |
| AUPP584298A0 (en) | 1998-10-08 |
| JP2002524524A (ja) | 2002-08-06 |
| JP4979848B2 (ja) | 2012-07-18 |
| BR9913712A (pt) | 2001-05-29 |
| NZ510289A (en) | 2002-10-25 |
| KR20010075066A (ko) | 2001-08-09 |
| EP1113806B1 (en) | 2007-09-05 |
| EP1113806A1 (en) | 2001-07-11 |
| EP1113806A4 (en) | 2003-06-25 |
| ATE372123T1 (de) | 2007-09-15 |
| CN101352451A (zh) | 2009-01-28 |
| US6464971B1 (en) | 2002-10-15 |
| KR100720905B1 (ko) | 2007-05-25 |
| CN1323214A (zh) | 2001-11-21 |
| CA2343113C (en) | 2009-11-24 |
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