CN101352451A - 阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 - Google Patents
阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 Download PDFInfo
- Publication number
- CN101352451A CN101352451A CNA2008100874448A CN200810087444A CN101352451A CN 101352451 A CN101352451 A CN 101352451A CN A2008100874448 A CNA2008100874448 A CN A2008100874448A CN 200810087444 A CN200810087444 A CN 200810087444A CN 101352451 A CN101352451 A CN 101352451A
- Authority
- CN
- China
- Prior art keywords
- dendritic
- end capped
- acid
- solution
- pamam
- 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.)
- Pending
Links
- 125000002091 cationic group Chemical group 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 title abstract description 80
- 239000000412 dendrimer Substances 0.000 title abstract description 14
- 229920000736 dendritic polymer Polymers 0.000 title abstract description 14
- 230000002141 anti-parasite Effects 0.000 title abstract description 4
- 239000003096 antiparasitic agent Substances 0.000 title abstract description 4
- 230000000845 anti-microbial effect Effects 0.000 title abstract description 3
- 125000000129 anionic group Chemical group 0.000 title description 4
- -1 polypropylen Polymers 0.000 claims abstract description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 150000001450 anions Chemical group 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 15
- 230000003071 parasitic effect Effects 0.000 claims abstract description 12
- 108010039918 Polylysine Proteins 0.000 claims abstract description 8
- 229920000656 polylysine Polymers 0.000 claims abstract description 8
- 241000233866 Fungi Species 0.000 claims abstract description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 244000052769 pathogen Species 0.000 claims abstract description 4
- 230000001717 pathogenic effect Effects 0.000 claims abstract description 4
- 150000002466 imines Chemical class 0.000 claims abstract 3
- 229920001155 polypropylene Polymers 0.000 claims abstract 3
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 165
- 238000002360 preparation method Methods 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 27
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 17
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- PIVQQUNOTICCSA-UHFFFAOYSA-N ANTU Chemical compound C1=CC=C2C(NC(=S)N)=CC=CC2=C1 PIVQQUNOTICCSA-UHFFFAOYSA-N 0.000 claims description 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000000844 anti-bacterial effect Effects 0.000 claims description 11
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 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 description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 208000030852 Parasitic disease Diseases 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 241000555268 Dendroides Species 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 229920000831 ionic polymer Polymers 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- JNZYADHPGVZMQK-UHFFFAOYSA-N 3-(aminomethyl)phenol Chemical compound NCC1=CC=CC(O)=C1 JNZYADHPGVZMQK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 3
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 244000053095 fungal pathogen Species 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 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
- 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 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- BXXDVVIXRUHQED-UHFFFAOYSA-N (3,5-diacetamido-2-hydroxyphenyl)arsonic acid Chemical compound CC(=O)Nc1cc(NC(C)=O)c(O)c(c1)[As](O)(O)=O BXXDVVIXRUHQED-UHFFFAOYSA-N 0.000 claims 1
- ITHZDEPTZVPHOV-UHFFFAOYSA-N C(CCC)(=O)NC1=CC(=C(C=C1NC(C)=O)[As](O)(O)=O)O Chemical compound C(CCC)(=O)NC1=CC(=C(C=C1NC(C)=O)[As](O)(O)=O)O ITHZDEPTZVPHOV-UHFFFAOYSA-N 0.000 claims 1
- ONYMMLUOJYMTCK-UHFFFAOYSA-N C1(=CC=C(C=C1)NC=1C(=C(C=C(C1)NC(C)=O)[As](O)(O)=O)O)C Chemical compound C1(=CC=C(C=C1)NC=1C(=C(C=C(C1)NC(C)=O)[As](O)(O)=O)O)C ONYMMLUOJYMTCK-UHFFFAOYSA-N 0.000 claims 1
- NGIPJYMCWXOYMZ-UHFFFAOYSA-N CCCCCCCCCCC(=O)NC=1C(=C(C=C(C1)NC(C)=O)[As](O)(O)=O)O Chemical compound CCCCCCCCCCC(=O)NC=1C(=C(C=C(C1)NC(C)=O)[As](O)(O)=O)O NGIPJYMCWXOYMZ-UHFFFAOYSA-N 0.000 claims 1
- 208000031888 Mycoses Diseases 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 244000000190 yeast pathogen Species 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 230000001580 bacterial effect Effects 0.000 abstract description 5
- 239000004952 Polyamide Substances 0.000 abstract description 3
- 229920002647 polyamide Polymers 0.000 abstract description 3
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 195
- 239000007787 solid Substances 0.000 description 97
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 238000000746 purification Methods 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- 238000002523 gelfiltration Methods 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 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 35
- 238000012360 testing method Methods 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- 239000012043 crude product Substances 0.000 description 26
- 239000011734 sodium Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 244000045947 parasite Species 0.000 description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 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
- 230000000694 effects Effects 0.000 description 16
- 210000003743 erythrocyte Anatomy 0.000 description 16
- 150000004702 methyl esters Chemical class 0.000 description 16
- 241000218636 Thuja Species 0.000 description 14
- 229920001429 chelating resin Polymers 0.000 description 14
- 150000003214 pyranose derivatives Chemical class 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000013459 approach Methods 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 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 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CRZIAMCADJKTOG-UHFFFAOYSA-N C(C)(=O)NC=1C=CC(=C(C1)[As](O)(O)=O)O Chemical compound C(C)(=O)NC=1C=CC(=C(C1)[As](O)(O)=O)O CRZIAMCADJKTOG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 244000005700 microbiome Species 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- SYRZNUUUCYEAMO-UHFFFAOYSA-N N(=[N+]=[N-])C1=CC(=C(C=C1NC(C)=O)[As](O)(O)=O)O Chemical compound N(=[N+]=[N-])C1=CC(=C(C=C1NC(C)=O)[As](O)(O)=O)O SYRZNUUUCYEAMO-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- ABZCGHUHIAPTJK-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)NC(=S)N Chemical compound [Na].C1(=CC=CC=C1)NC(=S)N ABZCGHUHIAPTJK-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000001963 growth medium Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 description 6
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000005096 rolling process Methods 0.000 description 6
- 238000001542 size-exclusion chromatography Methods 0.000 description 6
- 235000010265 sodium sulphite Nutrition 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 5
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 5
- FPCFPKWXJQIBQB-UHFFFAOYSA-N 4-amino-4-oxo-2-sulfobutanoic acid;sodium Chemical compound [Na].NC(=O)CC(C(O)=O)S(O)(=O)=O FPCFPKWXJQIBQB-UHFFFAOYSA-N 0.000 description 5
- 241000223960 Plasmodium falciparum Species 0.000 description 5
- 230000002152 alkylating effect Effects 0.000 description 5
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JCYZMTMYPZHVBF-UHFFFAOYSA-N Melarsoprol Chemical compound NC1=NC(N)=NC(NC=2C=CC(=CC=2)[As]2SC(CO)CS2)=N1 JCYZMTMYPZHVBF-UHFFFAOYSA-N 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- ZJCHELZXNQNSBF-UHFFFAOYSA-N [Na].C(CCC(=O)N)(=O)N Chemical compound [Na].C(CCC(=O)N)(=O)N ZJCHELZXNQNSBF-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 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 description 4
- 239000000872 buffer Substances 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229930182478 glucoside Natural products 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000002054 inoculum Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 201000004792 malaria Diseases 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 4
- 230000000505 pernicious effect Effects 0.000 description 4
- 210000001563 schizont Anatomy 0.000 description 4
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 description 3
- MFBPZROATHHERV-UHFFFAOYSA-N 4-(carbamothioylamino)naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(NC(=S)N)=CC(S(O)(=O)=O)=CC2=C1 MFBPZROATHHERV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PGDIIDLAIKTETC-UHFFFAOYSA-M CCCC[N+](CCCC)(CCCC)CCCC.C(CC(=O)[O-])C(=O)N Chemical compound CCCC[N+](CCCC)(CCCC)CCCC.C(CC(=O)[O-])C(=O)N PGDIIDLAIKTETC-UHFFFAOYSA-M 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 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 3
- 241001597008 Nomeidae Species 0.000 description 3
- 241000224016 Plasmodium Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- PJJOGZRCDLBXIG-UHFFFAOYSA-N [Na].NC(N)=S Chemical compound [Na].NC(N)=S PJJOGZRCDLBXIG-UHFFFAOYSA-N 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 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 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- 229960001728 melarsoprol Drugs 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 229920000333 poly(propyleneimine) Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- GWJGPQHULWCBNX-UHFFFAOYSA-M 4-oxo-4-(2-sulfoethylamino)butanoate tetrabutylazanium Chemical compound OS(=O)(=O)CCNC(=O)CCC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC GWJGPQHULWCBNX-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 108010026799 BRI 2999 Proteins 0.000 description 2
- 108010076839 BRI 6741 Proteins 0.000 description 2
- LYCBYAMNTODZIA-UHFFFAOYSA-N BrCC(=O)O.[N+](=O)([O-])C1=CC=C(C(=O)C2=CC=CC=C2)C=C1 Chemical compound BrCC(=O)O.[N+](=O)([O-])C1=CC=C(C(=O)C2=CC=CC=C2)C=C1 LYCBYAMNTODZIA-UHFFFAOYSA-N 0.000 description 2
- 229920003656 Daiamid® Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 208000009182 Parasitemia Diseases 0.000 description 2
- 241000233872 Pneumocystis carinii Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 241000223997 Toxoplasma gondii Species 0.000 description 2
- 241000223104 Trypanosoma Species 0.000 description 2
- RFUGMORVSDZBLC-UHFFFAOYSA-N [Na].CC(N)=O Chemical compound [Na].CC(N)=O RFUGMORVSDZBLC-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- UKYZWASSXSSTCI-UHFFFAOYSA-N c1cc[nH+]cc1.CCCCCCCCCCCCC([NH-])=O Chemical class c1cc[nH+]cc1.CCCCCCCCCCCCC([NH-])=O UKYZWASSXSSTCI-UHFFFAOYSA-N 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229940032049 enterococcus faecalis Drugs 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 210000003936 merozoite Anatomy 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 210000003812 trophozoite Anatomy 0.000 description 2
- 239000000273 veterinary drug Substances 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- ZJIFDEVVTPEXDL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) hydrogen carbonate Chemical compound OC(=O)ON1C(=O)CCC1=O ZJIFDEVVTPEXDL-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 description 1
- MSAUJABQNBNSCB-UHFFFAOYSA-N 2-(carbamothioylamino)benzene-1,4-disulfonic acid Chemical compound S(=O)(=O)(O)C=1C=C(C(=CC=1)S(=O)(=O)O)NC(=S)N MSAUJABQNBNSCB-UHFFFAOYSA-N 0.000 description 1
- UMMNJKHRUSCRJM-UHFFFAOYSA-N 2-(carbamoylamino)terephthalic acid Chemical compound NC(=O)NC1=CC(C(O)=O)=CC=C1C(O)=O UMMNJKHRUSCRJM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YWLHQBNWPCKZSB-UHFFFAOYSA-M 2-aminoethanesulfonate;tetrabutylazanium Chemical compound NCCS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC YWLHQBNWPCKZSB-UHFFFAOYSA-M 0.000 description 1
- RZRAKAPVDKRJKW-UHFFFAOYSA-N 2-isothiocyanatobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1N=C=S RZRAKAPVDKRJKW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- OVILZFVTUVWJTO-UHFFFAOYSA-N 4-(chloromethyl)benzamide Chemical compound NC(=O)C1=CC=C(CCl)C=C1 OVILZFVTUVWJTO-UHFFFAOYSA-N 0.000 description 1
- NCHUMJFHIHGJQD-UHFFFAOYSA-N 4-isothiocyanatobenzenesulfonic acid;sodium;hydrate Chemical compound O.[Na].OS(=O)(=O)C1=CC=C(N=C=S)C=C1 NCHUMJFHIHGJQD-UHFFFAOYSA-N 0.000 description 1
- RBEFRYQKJYMLCC-UHFFFAOYSA-N 4-isothiocyanatobenzoic acid Chemical compound OC(=O)C1=CC=C(N=C=S)C=C1 RBEFRYQKJYMLCC-UHFFFAOYSA-N 0.000 description 1
- KIQNQOQMGFSEMM-UHFFFAOYSA-N 5-(carbamothioylamino)benzene-1,3-disulfonic acid Chemical compound NC(=S)NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1 KIQNQOQMGFSEMM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010005098 Blastomycosis Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000389783 Bulbonaricus brucei Species 0.000 description 1
- BQGJSGZSBWFADD-UHFFFAOYSA-N C(=O)(O)C1=CC=C(C=C1)C1(C(=O)O)C(C(C(=O)O)=CC=C1)C Chemical compound C(=O)(O)C1=CC=C(C=C1)C1(C(=O)O)C(C(C(=O)O)=CC=C1)C BQGJSGZSBWFADD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 241000223936 Cryptosporidium parvum Species 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- 101100326341 Drosophila melanogaster brun gene Proteins 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 229930194076 Germanin Natural products 0.000 description 1
- 238000002738 Giemsa staining Methods 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 241000222722 Leishmania <genus> Species 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- MVEFMQOVKOHFMQ-UHFFFAOYSA-N N=C=S.OP(CC(C=C1)=CC=C1[Na])(O)=O Chemical compound N=C=S.OP(CC(C=C1)=CC=C1[Na])(O)=O MVEFMQOVKOHFMQ-UHFFFAOYSA-N 0.000 description 1
- MYIMBTKUXISSKX-UHFFFAOYSA-N NC(=O)NC1=CC=C(P(O)(O)=O)C=C1 Chemical compound NC(=O)NC1=CC=C(P(O)(O)=O)C=C1 MYIMBTKUXISSKX-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000223980 Plasmodium falciparum NF54 Species 0.000 description 1
- 206010035500 Plasmodium falciparum infection Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000190932 Rhodopseudomonas Species 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- IURSEHNPPMRYFP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]methylphosphonic acid;sodium Chemical compound [Na].NC(=S)NC1=CC=C(CP(O)(O)=O)C=C1 IURSEHNPPMRYFP-UHFFFAOYSA-N 0.000 description 1
- YLOCTQLBEOXFNG-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]phosphonic acid;sodium Chemical compound [Na].NC(=S)NC1=CC=C(P(O)(O)=O)C=C1 YLOCTQLBEOXFNG-UHFFFAOYSA-N 0.000 description 1
- 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
- FHZLKFQGLCUKOV-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)NC(=O)N Chemical compound [Na].C1(=CC=CC=C1)NC(=O)N FHZLKFQGLCUKOV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000909 amidinium group Chemical group 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 230000000680 avirulence Effects 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WPCXDBCEDWUSOU-UHFFFAOYSA-N benzoyl iodide Chemical compound IC(=O)C1=CC=CC=C1 WPCXDBCEDWUSOU-UHFFFAOYSA-N 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000011748 cell maturation Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 238000005497 microtitration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WZHFFMIYUIHVET-UHFFFAOYSA-N n,n-dicyclohexylformamide Chemical compound C1CCCCC1N(C=O)C1CCCCC1 WZHFFMIYUIHVET-UHFFFAOYSA-N 0.000 description 1
- RTMDKYIXNXHUDS-UHFFFAOYSA-N n-ethanethioylacetamide Chemical compound CC(=O)NC(C)=S RTMDKYIXNXHUDS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000002445 nipple Anatomy 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
- 150000004880 oxines Chemical class 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 230000037361 pathway Effects 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
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 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 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
- AOQGBYRBAGKHDC-UHFFFAOYSA-M sodium benzoylazanide Chemical compound [Na+].[NH-]C(=O)c1ccccc1 AOQGBYRBAGKHDC-UHFFFAOYSA-M 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- KSVSZLXDULFGDQ-UHFFFAOYSA-M sodium;4-aminobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1 KSVSZLXDULFGDQ-UHFFFAOYSA-M 0.000 description 1
- RROSXLCQOOGZBR-UHFFFAOYSA-N sodium;isothiocyanate Chemical compound [Na+].[N-]=C=S RROSXLCQOOGZBR-UHFFFAOYSA-N 0.000 description 1
- LPXFITACVAQQAL-UHFFFAOYSA-M sodium;prop-2-enoylazanide Chemical compound [Na+].[NH-]C(=O)C=C LPXFITACVAQQAL-UHFFFAOYSA-M 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000001360 synchronised effect Effects 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
- 238000012956 testing procedure Methods 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 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
- 229940044959 vaginal cream Drugs 0.000 description 1
- 239000000522 vaginal cream Substances 0.000 description 1
- 229940044952 vaginal foam Drugs 0.000 description 1
- 239000000259 vaginal foam Substances 0.000 description 1
- 229940120293 vaginal suppository Drugs 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Images
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPP5842A AUPP584298A0 (en) | 1998-09-14 | 1998-09-14 | Antimicrobial and antiparasitic agents |
| AUPP5842 | 1998-09-14 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99812270A Division CN1323214A (zh) | 1998-09-14 | 1999-09-13 | 阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101352451A true CN101352451A (zh) | 2009-01-28 |
Family
ID=3810064
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008100874448A Pending CN101352451A (zh) | 1998-09-14 | 1999-09-13 | 阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 |
| CN99812270A Pending CN1323214A (zh) | 1998-09-14 | 1999-09-13 | 阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99812270A Pending CN1323214A (zh) | 1998-09-14 | 1999-09-13 | 阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 |
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=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103179855A (zh) * | 2010-06-30 | 2013-06-26 | 刘慧文 | 抗菌化合物 |
| CN106255413A (zh) * | 2014-03-28 | 2016-12-21 | 伽马保健有限公司 | 液体抗微生物组合物 |
Families Citing this family (50)
| 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 |
| 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 |
| 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
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103179855A (zh) * | 2010-06-30 | 2013-06-26 | 刘慧文 | 抗菌化合物 |
| CN106255413A (zh) * | 2014-03-28 | 2016-12-21 | 伽马保健有限公司 | 液体抗微生物组合物 |
| CN106255413B (zh) * | 2014-03-28 | 2022-03-18 | 伽马保健有限公司 | 液体抗微生物组合物 |
| CN114588077A (zh) * | 2014-03-28 | 2022-06-07 | 伽马保健有限公司 | 液体抗微生物组合物 |
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 |
| DE69937059T2 (de) | 2008-05-29 |
| EP1113806A4 (en) | 2003-06-25 |
| ATE372123T1 (de) | 2007-09-15 |
| US6464971B1 (en) | 2002-10-15 |
| KR100720905B1 (ko) | 2007-05-25 |
| CN1323214A (zh) | 2001-11-21 |
| CA2343113C (en) | 2009-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101352451A (zh) | 阴离子型或阳离子型树枝状聚合物抗微生物或抗寄生物的组合物 | |
| EP0927217B1 (en) | Angiogenic inhibitory compounds | |
| DE69534686T2 (de) | Antivirale dendrimere | |
| DE69737658T2 (de) | Polyanionische polymere als adjuvantien zur mukosalen immunisierung | |
| US5693751A (en) | Water soluble high molecular weight polymerized drug preparation | |
| JP3310000B2 (ja) | 水溶性高分子抗癌剤及び薬物担持用担体 | |
| EP1383539B1 (en) | Anticancer drug-chitosan complex forming self-aggregates and preparation method thereof | |
| WO2000015239A1 (en) | Inhibition of toxic materials or substances using dendrimers | |
| US20030129158A1 (en) | Anionic or cationic dendrimer antimicrobial or antiparasitic compositions | |
| CN110152013B (zh) | 一种果胶-阿霉素轭合物及其制备方法和用途 | |
| JP3111099B2 (ja) | 水溶性高分子化薬剤の製造法 | |
| AU767970B2 (en) | Anionic or cationic dendrimer antimicrobial or antiparasitic compositions | |
| CN110418653B (zh) | 一种果胶-阿霉素轭合物及其制备方法和用途 | |
| CN115068624B (zh) | 一种肽类树形分子载药体系及其制备方法和应用 | |
| AU682970B2 (en) | Antiviral dendrimers | |
| MXPA01002667A (en) | Anionic or cationic dendrimer antimicrobial or antiparasitic compositions | |
| AU5841599A (en) | Inhibition of toxic materials or substances using dendrimers | |
| CN113368256A (zh) | 分枝葡萄糖和生物素介导的脑胶质瘤靶向智能脂质体材料 | |
| HK1002899B (en) | Antiviral dendrimers | |
| MXPA96006421A (en) | Dendrimeros antivira | |
| MXPA01002665A (en) | Inhibition of toxic materials or substances using dendrimers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20090128 |