DE69933890T2 - Antimykotische wirkung von dikationischen molekülen - Google Patents
Antimykotische wirkung von dikationischen molekülen Download PDFInfo
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- DE69933890T2 DE69933890T2 DE69933890T DE69933890T DE69933890T2 DE 69933890 T2 DE69933890 T2 DE 69933890T2 DE 69933890 T DE69933890 T DE 69933890T DE 69933890 T DE69933890 T DE 69933890T DE 69933890 T2 DE69933890 T2 DE 69933890T2
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- Prior art keywords
- alkyl
- branched
- group
- linear
- aryl
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- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QXIHQDOUUDXWFX-UHFFFAOYSA-N ethyl 3-bromo-2-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(=O)C(Br)C1=CC=CC=C1 QXIHQDOUUDXWFX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
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- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229960004130 itraconazole Drugs 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
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- 238000012153 long-term therapy Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- NIMFJRWUPRWDNW-UHFFFAOYSA-N n'-propan-2-yl-3-[5-[3-(n'-propan-2-ylcarbamimidoyl)phenyl]furan-2-yl]benzenecarboximidamide;dihydrochloride Chemical compound Cl.Cl.CC(C)N=C(N)C1=CC=CC(C=2OC(=CC=2)C=2C=C(C=CC=2)C(N)=NC(C)C)=C1 NIMFJRWUPRWDNW-UHFFFAOYSA-N 0.000 description 1
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- 229960000988 nystatin Drugs 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- 238000010626 work up procedure Methods 0.000 description 1
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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10092898P | 1998-09-17 | 1998-09-17 | |
| US100928P | 1998-09-17 | ||
| PCT/US1999/021383 WO2000015212A2 (en) | 1998-09-17 | 1999-09-15 | Antifungal activity of dicationic molecules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69933890D1 DE69933890D1 (de) | 2006-12-14 |
| DE69933890T2 true DE69933890T2 (de) | 2007-03-15 |
Family
ID=22282251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69933890T Expired - Fee Related DE69933890T2 (de) | 1998-09-17 | 1999-09-15 | Antimykotische wirkung von dikationischen molekülen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6326395B1 (enExample) |
| EP (1) | EP1143959B1 (enExample) |
| JP (1) | JP2002524503A (enExample) |
| AT (1) | ATE344028T1 (enExample) |
| AU (2) | AU770656B2 (enExample) |
| CA (1) | CA2344445A1 (enExample) |
| DE (1) | DE69933890T2 (enExample) |
| ES (1) | ES2275362T3 (enExample) |
| WO (1) | WO2000015212A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0016565A (pt) * | 1999-12-20 | 2002-09-17 | Univ North Carolina | Compostos diamidina como ligantes de pequeno sulco de dna |
| US6569853B1 (en) * | 2000-11-06 | 2003-05-27 | Combinatorx, Incorporated | Combinations of chlorpromazine and pentamidine for the treatment of neoplastic disorders |
| CA2455497A1 (en) * | 2001-08-31 | 2003-03-06 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
| AU2003302218A1 (en) | 2002-05-16 | 2004-06-18 | Genelabs Technologies, Inc | Aryl and heteroaryl compounds as antibacterial and antifungal agents |
| CA2504742A1 (en) * | 2002-11-27 | 2004-06-17 | University Of North Carolina At Chapel Hill | Process for synthesis bis-aryl diamidoxime compounds |
| US20050054708A1 (en) * | 2003-07-28 | 2005-03-10 | Nichols Matthew James | Combinations of drugs for the treatment of neoplasms |
| US20050080075A1 (en) * | 2003-08-25 | 2005-04-14 | Nichols M. James | Formulations, conjugates, and combinations of drugs for the treatment of neoplasms |
| US20050100508A1 (en) * | 2003-11-12 | 2005-05-12 | Nichols M. J. | Methods for identifying drug combinations for the treatment of proliferative diseases |
| US20050158320A1 (en) * | 2003-11-12 | 2005-07-21 | Nichols M. J. | Combinations for the treatment of proliferative diseases |
| JP2007513175A (ja) * | 2003-12-05 | 2007-05-24 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 抗菌剤としてのカチオンで置換されたベンゾフラン |
| US7262223B2 (en) * | 2004-01-23 | 2007-08-28 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
| WO2005086754A2 (en) * | 2004-03-08 | 2005-09-22 | Georgia State University Research Foundation, Inc. | Dicationic compounds for activity against trichomonas vaginalis |
| US7994225B2 (en) * | 2004-03-17 | 2011-08-09 | Rempex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors for the treatment of ophthalmic and otic infections |
| EP1732527A2 (en) * | 2004-03-17 | 2006-12-20 | Mpex Pharmaceuticals, Inc. | Use and administration of bacterial efflux pump inhibitors |
| AU2005233632A1 (en) | 2004-04-13 | 2005-10-27 | Icagen, Inc. | Polycyclic pyridines as potassium ion channel modulators |
| DE102004031656A1 (de) * | 2004-06-30 | 2006-01-19 | Merck Patent Gmbh | Tetrahydrochinoline |
| GB0619325D0 (en) * | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| DE102007013854A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Tetrahydrochinoline |
| DE102007013856A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydropyrrolochinoline |
| DE102007013855A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydrochinoline |
| EP2194981B1 (en) * | 2007-10-05 | 2011-11-23 | Université de Mons-Hainaut | Bisbenzimidazoles as antimalarial agents |
| WO2009084544A1 (ja) * | 2007-12-27 | 2009-07-09 | Idemitsu Kosan Co., Ltd. | 含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
| EP3159033B1 (en) | 2008-05-01 | 2019-02-27 | Bayer Intellectual Property GmbH | Catheter balloon drug adherence techniques and methods |
| EP2328910B1 (en) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US11141752B2 (en) | 2012-12-27 | 2021-10-12 | Kateeva, Inc. | Techniques for arrayed printing of a permanent layer with improved speed and accuracy |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2122208A1 (en) | 1971-05-05 | 1972-11-23 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | Diamidino-benzimidazole derivs - with fungistatic activity |
| JPS51110531A (en) | 1975-03-26 | 1976-09-30 | Eisai Co Ltd | Amijinokagobutsuno seizoho |
| JPS5922697B2 (ja) | 1976-01-13 | 1984-05-28 | エーザイ株式会社 | ビス−（メタ−アミジノフエノキシ）−化合物 |
| DE2833135A1 (de) | 1978-07-28 | 1980-02-07 | Henkel Kgaa | Verwendung von substituierten oligocarbamidinen als mikrobistatika sowie diese enthaltende antimikrobielle mittel |
| US4397863A (en) | 1980-08-26 | 1983-08-09 | Research Triangle Institute | Inhibition of respiratory syncytial virus-induced cell fusion by amidino compounds |
| US4324794A (en) | 1980-08-26 | 1982-04-13 | Research Triangle Institute | Inhibition of respiratory syncytial virus-induced cell fusion by amidino compounds |
| US4619942A (en) | 1982-04-08 | 1986-10-28 | University Of North Carolina | Inhibition of Respiratory Syncytial virus-induced cell fusion by amidino compounds |
| US4940723A (en) | 1988-10-20 | 1990-07-10 | University Of North Carolina, Chapel Hill | Use of bis-(5-amidino-2-benzimidazolyl) methane (BABIM) to treat arthritis |
| US4963589A (en) | 1988-10-25 | 1990-10-16 | The University Of North Carolina At Chapel Hill | Methods for treating Giardia lamblia |
| US5202320A (en) | 1989-04-06 | 1993-04-13 | Tidwell Richard R | Method for treating leishmaniasis |
| US4933347A (en) | 1988-10-25 | 1990-06-12 | University Of North Carolina At Chapel Hill | Diamidines and bis(imidazolines) for the treatment of and prophylaxis against pneumocystis carinii pneumonia |
| US5206236A (en) | 1989-04-06 | 1993-04-27 | Tidwell Richard R | Method for the treatment of malaria |
| US5428051A (en) | 1992-10-13 | 1995-06-27 | University Of North Carolina | Methods of combating pneumocystis carinii pneumonia and compounds useful therefor |
| US5723288A (en) | 1994-05-06 | 1998-03-03 | The University Of North Carolina At Chapel Hill | Method of fluorescent detection of nucleic acids and cytoskeleton elements using bis-dicationic aryl furans, and kits useful therefor |
| US5602172A (en) | 1994-05-06 | 1997-02-11 | The University Of North Carolina At Chapel Hill | Methods of inhibiting Pneumocystis carinii pneumonia, Giardia lamblia, and Cryptosporidium and compounds useful therefor |
| US5667975A (en) | 1994-05-06 | 1997-09-16 | The University Of North Carolina | Method of fluorescent detection of nucleic acids and cytoskeleton elements using bis-dicationic aryl furans |
| US5521189A (en) | 1994-05-06 | 1996-05-28 | The University Of Nc At Ch | Methods of treating pneumocystis carinii pneumonia |
| US5643935A (en) | 1995-06-07 | 1997-07-01 | The University Of North Carolina At Chapel Hill | Method of combatting infectious diseases using dicationic bis-benzimidazoles |
| US5668166A (en) | 1995-06-07 | 1997-09-16 | Georgia State University Research Foundation, Inc. | Methods of inhibiting pneumocystis carinii pneumonia and compounds useful therefor |
| US5723495A (en) | 1995-11-16 | 1998-03-03 | The University Of North Carolina At Chapel Hill | Benzamidoxime prodrugs as antipneumocystic agents |
-
1999
- 1999-09-15 DE DE69933890T patent/DE69933890T2/de not_active Expired - Fee Related
- 1999-09-15 ES ES99969025T patent/ES2275362T3/es not_active Expired - Lifetime
- 1999-09-15 CA CA002344445A patent/CA2344445A1/en not_active Abandoned
- 1999-09-15 AT AT99969025T patent/ATE344028T1/de not_active IP Right Cessation
- 1999-09-15 WO PCT/US1999/021383 patent/WO2000015212A2/en not_active Ceased
- 1999-09-15 EP EP99969025A patent/EP1143959B1/en not_active Expired - Lifetime
- 1999-09-15 US US09/396,836 patent/US6326395B1/en not_active Expired - Lifetime
- 1999-09-15 AU AU60450/99A patent/AU770656B2/en not_active Ceased
- 1999-09-15 JP JP2000569796A patent/JP2002524503A/ja not_active Withdrawn
-
2004
- 2004-05-26 AU AU2004202311A patent/AU2004202311A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU770656B2 (en) | 2004-02-26 |
| WO2000015212A3 (en) | 2001-08-16 |
| ATE344028T1 (de) | 2006-11-15 |
| US6326395B1 (en) | 2001-12-04 |
| JP2002524503A (ja) | 2002-08-06 |
| DE69933890D1 (de) | 2006-12-14 |
| WO2000015212A2 (en) | 2000-03-23 |
| EP1143959B1 (en) | 2006-11-02 |
| EP1143959A2 (en) | 2001-10-17 |
| AU2004202311A1 (en) | 2004-06-24 |
| ES2275362T3 (es) | 2007-06-01 |
| AU6045099A (en) | 2000-04-03 |
| CA2344445A1 (en) | 2000-03-23 |
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