CA2259344A1 - Ionic polymers comprising an amino or ammonium group as anti-infective agents - Google Patents
Ionic polymers comprising an amino or ammonium group as anti-infective agents Download PDFInfo
- Publication number
- CA2259344A1 CA2259344A1 CA002259344A CA2259344A CA2259344A1 CA 2259344 A1 CA2259344 A1 CA 2259344A1 CA 002259344 A CA002259344 A CA 002259344A CA 2259344 A CA2259344 A CA 2259344A CA 2259344 A1 CA2259344 A1 CA 2259344A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- infection
- polymer
- monomer
- acrylamide
- 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.)
- Abandoned
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title claims abstract description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 5
- 239000004599 antimicrobial Substances 0.000 title description 3
- 229960005475 antiinfective agent Drugs 0.000 title description 2
- 229920000831 ionic polymer Polymers 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 131
- 239000000178 monomer Substances 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 75
- 229920001577 copolymer Polymers 0.000 claims abstract description 30
- 208000015181 infectious disease Diseases 0.000 claims abstract description 26
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 23
- 241000124008 Mammalia Species 0.000 claims abstract description 19
- 125000006852 aliphatic spacer Chemical group 0.000 claims abstract description 15
- 230000000813 microbial effect Effects 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 12
- 229920001519 homopolymer Polymers 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 117
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 44
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 35
- 229920001897 terpolymer Polymers 0.000 claims description 33
- -1 N-n-butylacrylame Chemical compound 0.000 claims description 25
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims description 17
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 16
- QQZXAODFGRZKJT-UHFFFAOYSA-N n-tert-butyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(C)(C)C QQZXAODFGRZKJT-UHFFFAOYSA-N 0.000 claims description 14
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 claims description 14
- 230000007935 neutral effect Effects 0.000 claims description 13
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 12
- AWDYCSUWSUENQK-UHFFFAOYSA-N n-decylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C=C AWDYCSUWSUENQK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 claims description 10
- LVJZCPNIJXVIAT-UHFFFAOYSA-N 1-ethenyl-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C=C)C(F)=C1F LVJZCPNIJXVIAT-UHFFFAOYSA-N 0.000 claims description 9
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 241000223936 Cryptosporidium parvum Species 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- PLXOUIVCSUBZIX-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)COC(=O)C=C PLXOUIVCSUBZIX-UHFFFAOYSA-N 0.000 claims description 6
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 206010017533 Fungal infection Diseases 0.000 claims description 5
- 208000031888 Mycoses Diseases 0.000 claims description 5
- 208000030852 Parasitic disease Diseases 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 claims description 4
- 241000589876 Campylobacter Species 0.000 claims description 3
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 3
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical group CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 claims description 3
- 241000193163 Clostridioides difficile Species 0.000 claims description 2
- 241000588724 Escherichia coli Species 0.000 claims description 2
- 241000224467 Giardia intestinalis Species 0.000 claims description 2
- 241000233870 Pneumocystis Species 0.000 claims description 2
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 241000607142 Salmonella Species 0.000 claims description 2
- 241000607768 Shigella Species 0.000 claims description 2
- 241000194017 Streptococcus Species 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229940085435 giardia lamblia Drugs 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 201000000317 pneumocystosis Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 5
- 208000028172 protozoa infectious disease Diseases 0.000 claims 4
- 206010001981 Amoebic infections Diseases 0.000 claims 3
- 206010017964 Gastrointestinal infection Diseases 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 208000019836 digestive system infectious disease Diseases 0.000 claims 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- RUACIFFMSHZUKZ-UHFFFAOYSA-O 3-Acrylamidopropyl trimethylammonium Chemical compound C[N+](C)(C)CCCNC(=O)C=C RUACIFFMSHZUKZ-UHFFFAOYSA-O 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- VZTGWJFIMGVKSN-UHFFFAOYSA-O trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium Chemical compound CC(=C)C(=O)NCCC[N+](C)(C)C VZTGWJFIMGVKSN-UHFFFAOYSA-O 0.000 claims 2
- WAFHGEHGNQDTGU-UHFFFAOYSA-O trimethyl-[6-(prop-2-enoylamino)hexyl]azanium Chemical compound C[N+](C)(C)CCCCCCNC(=O)C=C WAFHGEHGNQDTGU-UHFFFAOYSA-O 0.000 claims 2
- HYECVEPWZDUMKP-UHFFFAOYSA-N 2-[(trimethylazaniumyl)methyl]prop-2-enoate Chemical compound C[N+](C)(C)CC(=C)C([O-])=O HYECVEPWZDUMKP-UHFFFAOYSA-N 0.000 claims 1
- AIUAMYPYEUQVEM-UHFFFAOYSA-N trimethyl(2-prop-2-enoyloxyethyl)azanium Chemical compound C[N+](C)(C)CCOC(=O)C=C AIUAMYPYEUQVEM-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 108
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 104
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 35
- 239000000843 powder Substances 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- 229940093499 ethyl acetate Drugs 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- 108090000765 processed proteins & peptides Proteins 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 102000004196 processed proteins & peptides Human genes 0.000 description 13
- 238000003828 vacuum filtration Methods 0.000 description 12
- 239000006228 supernatant Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920002401 polyacrylamide Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- WCCVMVPVUAVUFI-UHFFFAOYSA-N 2-methylprop-2-enamide;hydrochloride Chemical compound Cl.CC(=C)C(N)=O WCCVMVPVUAVUFI-UHFFFAOYSA-N 0.000 description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 231100000433 cytotoxic Toxicity 0.000 description 4
- 230000001472 cytotoxic effect Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000002196 fr. b Anatomy 0.000 description 4
- 210000003918 fraction a Anatomy 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- YXMISKNUHHOXFT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) prop-2-enoate Chemical compound C=CC(=O)ON1C(=O)CCC1=O YXMISKNUHHOXFT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000010166 immunofluorescence Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- VQGWOOIHSXNRPW-UHFFFAOYSA-N n-butyl-2-methylprop-2-enamide Chemical compound CCCCNC(=O)C(C)=C VQGWOOIHSXNRPW-UHFFFAOYSA-N 0.000 description 3
- 229920000083 poly(allylamine) Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 2
- UABZBFJRDPRXJR-UHFFFAOYSA-N 2-methylidenebutanoate;trimethylazanium Chemical compound C[NH+](C)C.CCC(=C)C([O-])=O UABZBFJRDPRXJR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZAFFWOKULJCCSA-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;trimethylazanium;chloride Chemical compound [Cl-].C[NH+](C)C.CCOC(=O)C(C)=C ZAFFWOKULJCCSA-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SNPAMTGUOWHTMN-UHFFFAOYSA-N n-decyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C(C)=C SNPAMTGUOWHTMN-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 description 2
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- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- 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 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000588878 Eikenella corrodens Species 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
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- 241000605986 Fusobacterium nucleatum Species 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
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Classifications
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- 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
- A61K31/785—Polymers containing nitrogen
-
- 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
- A61P31/10—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
- A61P33/04—Amoebicides
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (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)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/670,764 | 1996-06-24 | ||
| US08/670,764 US6034129A (en) | 1996-06-24 | 1996-06-24 | Ionic polymers as anti-infective agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2259344A1 true CA2259344A1 (en) | 1997-12-31 |
Family
ID=24691770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002259344A Abandoned CA2259344A1 (en) | 1996-06-24 | 1997-06-05 | Ionic polymers comprising an amino or ammonium group as anti-infective agents |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US6034129A (enExample) |
| EP (1) | EP0915705B1 (enExample) |
| JP (1) | JP4293382B2 (enExample) |
| AU (1) | AU727732B2 (enExample) |
| BR (1) | BR9710984A (enExample) |
| CA (1) | CA2259344A1 (enExample) |
| DE (1) | DE69737232T2 (enExample) |
| WO (1) | WO1997049413A1 (enExample) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6034129A (en) * | 1996-06-24 | 2000-03-07 | Geltex Pharmaceuticals, Inc. | Ionic polymers as anti-infective agents |
| AUPO104396A0 (en) | 1996-07-17 | 1996-08-08 | Biomolecular Research Institute Limited | Antiviral linear polymers |
| US6290947B1 (en) | 1997-09-19 | 2001-09-18 | Geltex Pharmaceuticals, Inc. | Ionic polymers as toxin-binding agents |
| WO2000066175A2 (en) * | 1999-04-30 | 2000-11-09 | Slil Biomedical Corporation | Conjugates as therapies for cancer and prostate diseases |
| EP1177197B1 (en) * | 1999-04-30 | 2006-08-09 | Cellgate, Inc. | Polyamines and their use in therapy |
| WO2002038105A2 (en) * | 2000-11-08 | 2002-05-16 | Slil Biomedical Corporation | Novel polyamine analog-amino acid conjugates useful as anticancer agents |
| US6482402B1 (en) | 1999-05-13 | 2002-11-19 | Geltex Pharmaceuticals, Inc. | Antimicrobial compositions and methods |
| US6290946B1 (en) * | 1999-05-13 | 2001-09-18 | Geltex Pharmaceuticals, Inc. | Anionic polymers as toxin binders and antibacterial agents |
| US20080281041A1 (en) | 1999-06-07 | 2008-11-13 | Rozema David B | Reversibly Masked Polymers |
| US6733780B1 (en) | 1999-10-19 | 2004-05-11 | Genzyme Corporation | Direct compression polymer tablet core |
| US20020054903A1 (en) * | 1999-10-19 | 2002-05-09 | Joseph Tyler | Direct compression polymer tablet core |
| CA2434693A1 (en) * | 2001-01-18 | 2002-10-17 | Genzyme Corporation | Ionene polymers and their use as antimicrobial agents |
| CN102295744B (zh) * | 2001-03-08 | 2014-07-02 | 宾夕法尼亚州大学理事会 | 作为抗感染药的表面两亲聚合物 |
| JP2004526778A (ja) * | 2001-04-18 | 2004-09-02 | ジェンザイム コーポレーション | 脂肪族ポリアミンを用いるｘ症候群の処置方法 |
| US7041280B2 (en) * | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
| JP2003099614A (ja) * | 2001-09-21 | 2003-04-04 | Daiwa Securities Group Inc | 保有口数内売却処理装置、保有口数内売却処理システム及びプログラム |
| WO2003027674A1 (fr) * | 2001-09-21 | 2003-04-03 | Takara Bio Inc. | Support pour l'immobilisation des ligands |
| AU2002340224B2 (en) * | 2001-10-16 | 2008-11-27 | Progen Pharmaceuticals, Inc | Oligoamine compounds and derivatives thereof for cancer therapy |
| US7147873B2 (en) | 2002-01-16 | 2006-12-12 | 3M Innovative Properties Company | Antiseptic compositions and methods |
| US6838078B2 (en) | 2002-01-16 | 2005-01-04 | 3M Innovative Properties Company | Film-forming compositions and methods |
| US7005031B2 (en) * | 2002-01-16 | 2006-02-28 | 3M Innovative Properties Company | Pressure sensitive adhesives having quaternary ammonium functionality, articles, and methods |
| US20040166753A1 (en) * | 2002-06-10 | 2004-08-26 | Millward Dan B. | Modification of fabric fibers |
| JP4476807B2 (ja) * | 2002-07-22 | 2010-06-09 | ジェンザイム、コーポレーション | ポリ（カリウムおよびスチレンスルホン酸ナトリウム）、その製造およびその使用 |
| US20040044220A1 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| WO2004044305A1 (en) * | 2002-11-05 | 2004-05-27 | Nano-Tex, Llc | Odor-absorbing cellulosic fibrous substrates |
| WO2004046109A2 (en) * | 2002-11-19 | 2004-06-03 | Genzyme Corporation | Ionene oligomers and polymers |
| US8926997B1 (en) * | 2003-02-06 | 2015-01-06 | Richard F. Stockel | Polymeric biocidal salts |
| CA2519023C (en) | 2003-03-17 | 2014-05-20 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers and uses thereof |
| US7459502B2 (en) * | 2003-11-03 | 2008-12-02 | Ilypsa, Inc. | Pharmaceutical compositions comprising crosslinked polyamine polymers |
| US7608674B2 (en) * | 2003-11-03 | 2009-10-27 | Ilypsa, Inc. | Pharmaceutical compositions comprising cross-linked small molecule amine polymers |
| US7335795B2 (en) * | 2004-03-22 | 2008-02-26 | Ilypsa, Inc. | Crosslinked amine polymers |
| US7767768B2 (en) * | 2003-11-03 | 2010-08-03 | Ilypsa, Inc. | Crosslinked amine polymers |
| US7385012B2 (en) | 2003-11-03 | 2008-06-10 | Ilypsa, Inc. | Polyamine polymers |
| US7449605B2 (en) * | 2003-11-03 | 2008-11-11 | Ilypsa, Inc. | Crosslinked amine polymers |
| EP1711455A4 (en) | 2004-01-23 | 2007-11-07 | Univ Pennsylvania | FAZIAL AMPHIPHILE POLYARYL AND POLYARYL ALKINYL POLYMERS AND OLIGOMERS AND ITS APPLICATIONS |
| EP1771183B1 (en) * | 2004-07-23 | 2014-09-03 | The Trustees of The University of Pennsylvania | Antimicrobial copolymers and uses thereof |
| CN101027066B (zh) * | 2004-08-18 | 2011-05-18 | 宝利麦迪克斯股份有限公司 | 两亲聚降冰片烯衍生物及其使用方法 |
| WO2006044577A1 (en) * | 2004-10-13 | 2006-04-27 | Ilypsa, Inc. | Pharmaceutical compositions comprising a toxin-binding oligosaccharide and a polymeric particle |
| US7985418B2 (en) | 2004-11-01 | 2011-07-26 | Genzyme Corporation | Aliphatic amine polymer salts for tableting |
| US20060177415A1 (en) * | 2004-11-01 | 2006-08-10 | Burke Steven K | Once a day formulation for phosphate binders |
| KR20080004475A (ko) * | 2005-02-25 | 2008-01-09 | 유니버시티 오브 매사추세츠 | 표면적으로 양친매성인 중합체 및 올리고머, 그 조성물 및암치료방법으로서의 그 용도 |
| WO2007024973A1 (en) * | 2005-08-22 | 2007-03-01 | Quick-Med Technologies, Inc. | Disinfectant with quaternary ammonium polymers and copolymers |
| US8986669B2 (en) * | 2005-09-02 | 2015-03-24 | Genzyme Corporation | Method for removing phosphate and polymer used therefore |
| JP5595660B2 (ja) | 2005-09-15 | 2014-09-24 | ジェンザイム コーポレーション | アミンポリマー用サシェ製剤 |
| EP2016114A2 (en) * | 2006-05-05 | 2009-01-21 | Genzyme Corporation | Amine condensation polymers as phosphate sequestrants |
| MX2008016341A (es) * | 2006-06-26 | 2009-01-16 | Novartis Ag | Polimeros con actividad antimicrobiana conteniendo grupos de amonio cuaternario. |
| US20100124542A1 (en) * | 2006-07-18 | 2010-05-20 | Genzyme Corporation | Amine dendrimers |
| US8017109B2 (en) * | 2006-08-18 | 2011-09-13 | Roche Madison Inc. | Endosomolytic poly(acrylate) polymers |
| EP2066293A2 (en) | 2006-09-29 | 2009-06-10 | Genzyme Corporation | Amide dendrimer compositions |
| BRPI0720234A2 (pt) | 2006-12-14 | 2013-12-24 | Genzyme Corp | Composição farmacêutica |
| US20100129309A1 (en) * | 2007-02-23 | 2010-05-27 | Dhal Pradeep K | Amine polymer compositions |
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-
1996
- 1996-06-24 US US08/670,764 patent/US6034129A/en not_active Expired - Lifetime
-
1997
- 1997-06-05 EP EP97927985A patent/EP0915705B1/en not_active Expired - Lifetime
- 1997-06-05 JP JP50305098A patent/JP4293382B2/ja not_active Expired - Lifetime
- 1997-06-05 WO PCT/US1997/009733 patent/WO1997049413A1/en not_active Ceased
- 1997-06-05 BR BR9710984-3A patent/BR9710984A/pt not_active IP Right Cessation
- 1997-06-05 CA CA002259344A patent/CA2259344A1/en not_active Abandoned
- 1997-06-05 DE DE69737232T patent/DE69737232T2/de not_active Expired - Lifetime
- 1997-06-05 AU AU32311/97A patent/AU727732B2/en not_active Expired
-
2000
- 2000-01-28 US US09/493,639 patent/US6395777B2/en not_active Expired - Lifetime
-
2002
- 2002-02-21 US US10/081,022 patent/US6593366B2/en not_active Expired - Lifetime
-
2003
- 2003-02-25 US US10/374,014 patent/US6767549B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6593366B2 (en) | 2003-07-15 |
| JP2002515039A (ja) | 2002-05-21 |
| WO1997049413A1 (en) | 1997-12-31 |
| US6767549B2 (en) | 2004-07-27 |
| US20040022759A1 (en) | 2004-02-05 |
| EP0915705A1 (en) | 1999-05-19 |
| AU3231197A (en) | 1998-01-14 |
| DE69737232D1 (de) | 2007-02-22 |
| DE69737232T2 (de) | 2007-10-11 |
| BR9710984A (pt) | 2002-01-08 |
| US6034129A (en) | 2000-03-07 |
| US20020114777A1 (en) | 2002-08-22 |
| JP4293382B2 (ja) | 2009-07-08 |
| EP0915705B1 (en) | 2007-01-10 |
| US20010053794A1 (en) | 2001-12-20 |
| AU727732B2 (en) | 2000-12-21 |
| US6395777B2 (en) | 2002-05-28 |
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