AU2004292992A1 - Fused ring dicationic anti-protozoan agents and their prodrugs - Google Patents
Fused ring dicationic anti-protozoan agents and their prodrugs Download PDFInfo
- Publication number
- AU2004292992A1 AU2004292992A1 AU2004292992A AU2004292992A AU2004292992A1 AU 2004292992 A1 AU2004292992 A1 AU 2004292992A1 AU 2004292992 A AU2004292992 A AU 2004292992A AU 2004292992 A AU2004292992 A AU 2004292992A AU 2004292992 A1 AU2004292992 A1 AU 2004292992A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- aryl
- alkyl
- bis
- compound
- 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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- 239000000651 prodrug Substances 0.000 title description 12
- 229940002612 prodrug Drugs 0.000 title description 12
- 239000003795 chemical substances by application Substances 0.000 title description 9
- 230000000884 anti-protozoa Effects 0.000 title description 3
- 125000003118 aryl group Chemical group 0.000 claims description 194
- 125000000217 alkyl group Chemical group 0.000 claims description 193
- 229910052739 hydrogen Inorganic materials 0.000 claims description 170
- 150000001875 compounds Chemical class 0.000 claims description 154
- 238000000034 method Methods 0.000 claims description 82
- -1 alkoxycycloalkyl Chemical group 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 238000009472 formulation Methods 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 39
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000004423 acyloxy group Chemical group 0.000 claims description 33
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 33
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 31
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 31
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 8
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- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- FEWIOGITFAILBH-UHFFFAOYSA-N pyridin-2-yl-[7-(pyridin-2-yldiazenyl)-9h-fluoren-2-yl]diazene Chemical compound C1=C2CC3=CC(N=NC=4N=CC=CC=4)=CC=C3C2=CC=C1N=NC1=CC=CC=N1 FEWIOGITFAILBH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 201000002612 sleeping sickness Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YFNSYRCIQSAWDK-UHFFFAOYSA-N tert-butyl (ne)-n-[[[7-[[(e)-n,n'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-9,10-dioxoanthracen-2-yl]amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)C=C2C(=O)C3=CC(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)=CC=C3C(=O)C2=C1 YFNSYRCIQSAWDK-UHFFFAOYSA-N 0.000 description 1
- XXQJXCOVIGBXBF-UHFFFAOYSA-N tert-butyl (ne)-n-[[[7-[[(e)-n,n'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-9-oxofluoren-2-yl]amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)C=C2C(=O)C3=CC(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)=CC=C3C2=C1 XXQJXCOVIGBXBF-UHFFFAOYSA-N 0.000 description 1
- SUQARWSXULIXMI-UHFFFAOYSA-N tert-butyl (ne)-n-[[[7-[[(e)-n,n'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-9h-fluoren-2-yl]amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(=NC(=O)OC(C)(C)C)NC1=CC=C2C3=CC=C(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)C=C3CC2=C1 SUQARWSXULIXMI-UHFFFAOYSA-N 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
- UQJXXWHAJKRDKY-UHFFFAOYSA-N tert-butyl n-[[(2-methylpropan-2-yl)oxycarbonylamino]-methylsulfanylmethylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(SC)=NC(=O)OC(C)(C)C UQJXXWHAJKRDKY-UHFFFAOYSA-N 0.000 description 1
- BPFXWZSUKGHAQK-UHFFFAOYSA-N tert-butyl n-[[[6-[[n,n'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]acridin-3-yl]amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate Chemical compound C1=CC(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)=CC2=NC3=CC(NC(NC(=O)OC(C)(C)C)=NC(=O)OC(C)(C)C)=CC=C3C=C21 BPFXWZSUKGHAQK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- 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
- 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
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52501803P | 2003-11-24 | 2003-11-24 | |
| US60/525,018 | 2003-11-24 | ||
| PCT/US2004/038896 WO2005051296A2 (en) | 2003-11-24 | 2004-11-18 | Fused ring dicationic anti-protozoan agents and their prodrugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004292992A1 true AU2004292992A1 (en) | 2005-06-09 |
Family
ID=34632950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004292992A Abandoned AU2004292992A1 (en) | 2003-11-24 | 2004-11-18 | Fused ring dicationic anti-protozoan agents and their prodrugs |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7825279B2 (enExample) |
| EP (1) | EP1689705A4 (enExample) |
| JP (1) | JP2007513888A (enExample) |
| CN (1) | CN1886367A (enExample) |
| AU (1) | AU2004292992A1 (enExample) |
| CA (1) | CA2547972A1 (enExample) |
| WO (1) | WO2005051296A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2687964A1 (en) | 2007-06-01 | 2009-02-19 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| FR2920775B1 (fr) * | 2007-09-07 | 2009-11-06 | Pharma Hydro Dev P H D Soc Par | Nouveaux composes diaminophenothiazine, leur procede de preparation et leurs utilisations. |
| US8277026B2 (en) * | 2008-01-16 | 2012-10-02 | Zamtec Limited | Printhead cartridge insertion protocol |
| CA2934523A1 (en) | 2013-12-24 | 2015-07-02 | University Of Florida Research Foundation, Inc. | Phenazine derivatives as antimicrobial agents |
| WO2017011730A2 (en) * | 2015-07-15 | 2017-01-19 | University Of Florida Research Foundation, Incorporated | Phenazine derivatives as antimicrobial agents |
| WO2018152436A1 (en) | 2017-02-17 | 2018-08-23 | University Of Research Foundation, Incorporated | Phenazine derivatives as antimicrobial agents |
| US12060334B2 (en) | 2021-03-12 | 2024-08-13 | University Of Florida Research Foundation, Incorporated | 3-substituted phenazine derivatives as antimicrobial agents |
| ES2950283B2 (es) | 2022-03-04 | 2024-02-12 | Consejo Superior Investigacion | Compuestos derivados de 4-amino-n-(4-aminofenil)benzamida y analogos y uso de los mismos |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1374695A (en) * | 1919-11-21 | 1921-04-12 | Barrett Co | Catalytic oxidation of fluorene |
| DE1014518B (de) * | 1956-03-09 | 1957-08-29 | Bayer Ag | Verfahren zum Faerben und Bedrucken von Polymerisaten und Mischpolymerisaten des Acrylnitrils bzw. Dicyanaethylens |
| US4141992A (en) * | 1975-08-22 | 1979-02-27 | American Cyanamid Company | Cycloalkylcarboxyamidines and halobenzamidines as anti-amebic agents |
| US5521190A (en) * | 1993-05-27 | 1996-05-28 | Fmc Corporation | Insecticidal pterdines and 8-deazapteridines |
| US5521189A (en) * | 1994-05-06 | 1996-05-28 | The University Of Nc At Ch | Methods of treating pneumocystis carinii pneumonia |
| US5677349A (en) * | 1995-04-27 | 1997-10-14 | Gilad; Gad M. | Agmatine for the treatment of neurotrauma and neurodegenerative diseases |
| US5668167A (en) * | 1995-06-07 | 1997-09-16 | Duke University | Methods of treating microbial infections |
| WO1996040138A1 (en) | 1995-06-07 | 1996-12-19 | The Administrators Of The Tulane Educational Fund | Chloroquine analogs and methods of preventing and treating plasmodial disease |
| US5628984A (en) * | 1995-07-31 | 1997-05-13 | University Of North Carolina At Chapel Hill | Method of detecting lung disease |
| WO2000010990A2 (en) * | 1998-08-20 | 2000-03-02 | University Of North Carolina At Chapel Hill | Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof |
| CA2361734A1 (en) * | 1999-01-26 | 2000-10-12 | Andre Rosowsky | Pharmaceutically active compounds and methods of use thereof |
| FR2796642B1 (fr) * | 1999-07-21 | 2001-10-19 | Centre Nat Rech Scient | Precurseurs de sels de bis-ammonium quaternaire et leurs applications comme prodrogues ayant une activite anti-parasitaire |
| JP2002097133A (ja) * | 2000-07-17 | 2002-04-02 | Shionogi & Co Ltd | トリアゼン化合物を含有する抗マラリア剤および殺線虫剤 |
| EP1545544A2 (en) * | 2002-07-11 | 2005-06-29 | Combinatorx, Incorporated | Combinations of drugs for the treatment of neoplasms |
| US20050054708A1 (en) * | 2003-07-28 | 2005-03-10 | Nichols Matthew James | Combinations of drugs for the treatment of neoplasms |
| ITMI20031754A1 (it) | 2003-09-12 | 2005-03-13 | Fabrizio Marcucci | Composizione microbicida. |
-
2004
- 2004-11-18 JP JP2006541427A patent/JP2007513888A/ja active Pending
- 2004-11-18 US US10/992,607 patent/US7825279B2/en not_active Expired - Fee Related
- 2004-11-18 WO PCT/US2004/038896 patent/WO2005051296A2/en not_active Ceased
- 2004-11-18 CN CNA2004800347505A patent/CN1886367A/zh active Pending
- 2004-11-18 EP EP04811591A patent/EP1689705A4/en not_active Withdrawn
- 2004-11-18 AU AU2004292992A patent/AU2004292992A1/en not_active Abandoned
- 2004-11-18 CA CA002547972A patent/CA2547972A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005051296A3 (en) | 2005-07-28 |
| EP1689705A2 (en) | 2006-08-16 |
| US20050165044A1 (en) | 2005-07-28 |
| WO2005051296A2 (en) | 2005-06-09 |
| CN1886367A (zh) | 2006-12-27 |
| JP2007513888A (ja) | 2007-05-31 |
| US7825279B2 (en) | 2010-11-02 |
| CA2547972A1 (en) | 2005-06-09 |
| EP1689705A4 (en) | 2007-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |