DE69737232T2 - Ionische polymere als anti-infektiöse mittel - Google Patents
Ionische polymere als anti-infektiöse mittel Download PDFInfo
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- DE69737232T2 DE69737232T2 DE69737232T DE69737232T DE69737232T2 DE 69737232 T2 DE69737232 T2 DE 69737232T2 DE 69737232 T DE69737232 T DE 69737232T DE 69737232 T DE69737232 T DE 69737232T DE 69737232 T2 DE69737232 T2 DE 69737232T2
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- solution
- polymer
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- acrylamide
- Prior art date
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- 230000002924 anti-infective effect Effects 0.000 title 1
- 229920000831 ionic polymer Polymers 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 116
- 229920000642 polymer Polymers 0.000 claims description 111
- 239000000178 monomer Substances 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 37
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 36
- 229920001577 copolymer Polymers 0.000 claims description 32
- 230000002209 hydrophobic effect Effects 0.000 claims description 17
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 13
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 claims description 12
- 125000006852 aliphatic spacer Chemical group 0.000 claims description 11
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims description 11
- 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 11
- AWDYCSUWSUENQK-UHFFFAOYSA-N n-decylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C=C AWDYCSUWSUENQK-UHFFFAOYSA-N 0.000 claims description 10
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 10
- -1 N-n-decylallylamine Chemical compound 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
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- 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 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 2
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
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- 206010017533 Fungal infection Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 claims 1
- 230000036281 parasite infection Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 108
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- 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 66
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- 239000006228 supernatant Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 125000006850 spacer group Chemical group 0.000 description 7
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920002401 polyacrylamide Polymers 0.000 description 6
- 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 5
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
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- 229940085435 giardia lamblia Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- 235000013336 milk Nutrition 0.000 description 1
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- BVWUEIUNONATML-UHFFFAOYSA-N n-benzylethenamine Chemical compound C=CNCC1=CC=CC=C1 BVWUEIUNONATML-UHFFFAOYSA-N 0.000 description 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
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- 229960001914 paromomycin Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
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- 229920001184 polypeptide Polymers 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 230000000135 prohibitive effect Effects 0.000 description 1
- 210000001236 prokaryotic cell Anatomy 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- 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)
- Communicable Diseases (AREA)
- Oncology (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US670764 | 1996-06-24 | ||
| US08/670,764 US6034129A (en) | 1996-06-24 | 1996-06-24 | Ionic polymers as anti-infective agents |
| PCT/US1997/009733 WO1997049413A1 (en) | 1996-06-24 | 1997-06-05 | Ionic polymers as anti-infective agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69737232D1 DE69737232D1 (de) | 2007-02-22 |
| DE69737232T2 true DE69737232T2 (de) | 2007-10-11 |
Family
ID=24691770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69737232T Expired - Lifetime DE69737232T2 (de) | 1996-06-24 | 1997-06-05 | Ionische polymere als anti-infektiöse mittel |
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) |
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| 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 |
| CA2368801A1 (en) * | 1999-04-30 | 2000-11-09 | Slil Biomedical Corporation | Conjugates as therapies for cancer and prostate diseases |
| MXPA01011000A (es) * | 1999-04-30 | 2003-06-30 | Slil Biomedical Corp | Analogos de poliaminas conformacionalmente restringidos como terapias para enfermedades. |
| 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 |
| US20020054903A1 (en) * | 1999-10-19 | 2002-05-09 | Joseph Tyler | Direct compression polymer tablet core |
| US6733780B1 (en) | 1999-10-19 | 2004-05-11 | Genzyme Corporation | Direct compression polymer tablet core |
| JP2004513136A (ja) * | 2000-11-08 | 2004-04-30 | スリル バイオメディカル コーポレーション | 抗癌剤として有用な新規ポリアミンアナログ−アミノ酸結合体 |
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| DK1372551T3 (da) * | 2001-03-08 | 2009-01-12 | Univ Pennsylvania | Faciale amphifile polymerer som anti-infektionsmidler |
| KR20040018359A (ko) * | 2001-04-18 | 2004-03-03 | 젠자임 코포레이션 | 지방족 폴리아민으로 ｘ 증후군을 치료하는 방법 |
| US7041280B2 (en) * | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
| WO2003027674A1 (fr) * | 2001-09-21 | 2003-04-03 | Takara Bio Inc. | Support pour l'immobilisation des ligands |
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| US7147873B2 (en) * | 2002-01-16 | 2006-12-12 | 3M Innovative Properties Company | Antiseptic compositions and methods |
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| US20040044220A1 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| AU2003286779A1 (en) * | 2002-11-05 | 2004-06-03 | Nano-Tex, Llc | Odor-absorbing cellulosic fibrous substrates |
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| US8926997B1 (en) * | 2003-02-06 | 2015-01-06 | Richard F. Stockel | Polymeric biocidal salts |
| US9241917B2 (en) | 2003-03-17 | 2016-01-26 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers and uses thereof |
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| CA2599205A1 (en) * | 2005-02-25 | 2006-09-08 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers, compositions thereof, and use thereof in methods of treating cancer |
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-
1996
- 1996-06-24 US US08/670,764 patent/US6034129A/en not_active Expired - Lifetime
-
1997
- 1997-06-05 AU AU32311/97A patent/AU727732B2/en not_active Expired
- 1997-06-05 DE DE69737232T patent/DE69737232T2/de not_active Expired - Lifetime
- 1997-06-05 WO PCT/US1997/009733 patent/WO1997049413A1/en not_active Ceased
- 1997-06-05 EP EP97927985A patent/EP0915705B1/en not_active Expired - Lifetime
- 1997-06-05 CA CA002259344A patent/CA2259344A1/en not_active Abandoned
- 1997-06-05 JP JP50305098A patent/JP4293382B2/ja not_active Expired - Lifetime
- 1997-06-05 BR BR9710984-3A patent/BR9710984A/pt not_active IP Right Cessation
-
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 |
|---|---|
| US6767549B2 (en) | 2004-07-27 |
| AU727732B2 (en) | 2000-12-21 |
| JP4293382B2 (ja) | 2009-07-08 |
| US20040022759A1 (en) | 2004-02-05 |
| US20010053794A1 (en) | 2001-12-20 |
| EP0915705B1 (en) | 2007-01-10 |
| US6034129A (en) | 2000-03-07 |
| US6593366B2 (en) | 2003-07-15 |
| US6395777B2 (en) | 2002-05-28 |
| AU3231197A (en) | 1998-01-14 |
| EP0915705A1 (en) | 1999-05-19 |
| BR9710984A (pt) | 2002-01-08 |
| DE69737232D1 (de) | 2007-02-22 |
| JP2002515039A (ja) | 2002-05-21 |
| WO1997049413A1 (en) | 1997-12-31 |
| US20020114777A1 (en) | 2002-08-22 |
| CA2259344A1 (en) | 1997-12-31 |
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