AU2004262533A1 - Halogenated quinazolinyl nitrofurans as antibacterial agents - Google Patents
Halogenated quinazolinyl nitrofurans as antibacterial agents Download PDFInfo
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- AU2004262533A1 AU2004262533A1 AU2004262533A AU2004262533A AU2004262533A1 AU 2004262533 A1 AU2004262533 A1 AU 2004262533A1 AU 2004262533 A AU2004262533 A AU 2004262533A AU 2004262533 A AU2004262533 A AU 2004262533A AU 2004262533 A1 AU2004262533 A1 AU 2004262533A1
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- 239000003242 anti bacterial agent Substances 0.000 title description 23
- ASGWCEUDXQVGMY-UHFFFAOYSA-N 2-(2-nitrofuran-3-yl)quinazoline Chemical class O1C=CC(C=2N=C3C=CC=CC3=CN=2)=C1[N+](=O)[O-] ASGWCEUDXQVGMY-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 141
- 239000000203 mixture Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 208000035143 Bacterial infection Diseases 0.000 claims description 18
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 18
- QXBVXXWXFJUSKK-UHFFFAOYSA-N 4-chloro-6-fluoro-2-[2-(5-nitrofuran-2-yl)ethenyl]quinazoline Chemical compound O1C([N+](=O)[O-])=CC=C1C=CC1=NC(Cl)=C(C=C(F)C=C2)C2=N1 QXBVXXWXFJUSKK-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
- 241000894006 Bacteria Species 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- ZUBGQONHCPIWFN-UHFFFAOYSA-N 4-[[6-fluoro-2-[2-(5-nitrofuran-2-yl)ethenyl]quinazolin-4-yl]amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NC(C=CC=2OC(=CC=2)[N+]([O-])=O)=NC2=CC=C(F)C=C12 ZUBGQONHCPIWFN-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 9
- VBVVERNMTSXATJ-UHFFFAOYSA-N 6-fluoro-2-[2-(5-nitrofuran-2-yl)ethenyl]-1h-quinazolin-4-one Chemical compound O1C([N+](=O)[O-])=CC=C1C=CC1=NC2=CC=C(F)C=C2C(=O)N1 VBVVERNMTSXATJ-UHFFFAOYSA-N 0.000 claims description 8
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- 229920002554 vinyl polymer Polymers 0.000 claims description 4
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- 101150065749 Churc1 gene Proteins 0.000 claims description 3
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims 1
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- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 claims 1
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- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 25
- 230000000694 effects Effects 0.000 description 24
- 229960001907 nitrofurazone Drugs 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- -1 methylpiperazino group Chemical group 0.000 description 16
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- 230000003115 biocidal effect Effects 0.000 description 11
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- MIIPXOKMRQDPJA-UHFFFAOYSA-N 4-[[6-fluoro-7-(4-methylpiperazin-1-yl)-2-[2-(5-nitrofuran-2-yl)ethenyl]quinazolin-4-yl]amino]phenol Chemical compound C1CN(C)CCN1C1=CC2=NC(C=CC=3OC(=CC=3)[N+]([O-])=O)=NC(NC=3C=CC(O)=CC=3)=C2C=C1F MIIPXOKMRQDPJA-UHFFFAOYSA-N 0.000 description 10
- 230000000845 anti-microbial effect Effects 0.000 description 10
- 230000001580 bacterial effect Effects 0.000 description 10
- 244000005700 microbiome Species 0.000 description 10
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- 238000001727 in vivo Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 8
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 8
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 8
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A61P31/02—Local antiseptics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49333603P | 2003-08-08 | 2003-08-08 | |
| US60/493,336 | 2003-08-08 | ||
| PCT/CA2004/001466 WO2005014585A1 (en) | 2003-08-08 | 2004-08-06 | Halogenated quinazolinyl nitrofurans as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004262533A1 true AU2004262533A1 (en) | 2005-02-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004262533A Abandoned AU2004262533A1 (en) | 2003-08-08 | 2004-08-06 | Halogenated quinazolinyl nitrofurans as antibacterial agents |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7410974B2 (enExample) |
| EP (1) | EP1660486A4 (enExample) |
| JP (1) | JP2007501809A (enExample) |
| CN (1) | CN1832941A (enExample) |
| AU (1) | AU2004262533A1 (enExample) |
| BR (1) | BRPI0413372A (enExample) |
| CA (1) | CA2534405A1 (enExample) |
| MX (1) | MXPA06001552A (enExample) |
| WO (1) | WO2005014585A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010016646A1 (en) * | 1998-03-20 | 2001-08-23 | David C. Rueger | Osteogenic devices and methods of use thereof for repair of endochondral bone, osteochondral and chondral defects |
| JP2007501809A (ja) | 2003-08-08 | 2007-02-01 | ユリシーズ・ファーマシューティカル・プロダクツ・インコーポレイテッド | 抗菌剤としてのハロゲン化キナゾリニルニトロフラン |
| US20080146562A1 (en) * | 2003-08-08 | 2008-06-19 | Ulysses Pharmaceutical Products Inc., | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| AU2005287825A1 (en) * | 2004-09-23 | 2006-03-30 | Ulysses Pharmaceutical Products Inc. | Carbo- and hetero-cyclic antibiotics and use thereof |
| JP2009528545A (ja) | 2006-03-02 | 2009-08-06 | ザ ユーエービー リサーチ ファウンデーション | マイコバクテリウム属の疾患検出、処置、および薬物開発 |
| US20110053964A1 (en) * | 2006-08-22 | 2011-03-03 | Roger Tung | 4-aminoquinazoline derivatives and methods of use thereof |
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| CN106924261A (zh) * | 2016-04-12 | 2017-07-07 | 郑海英 | 一种防治牙体牙髓感染的药物组合物 |
| GB201610869D0 (en) | 2016-06-22 | 2016-08-03 | Helperby Therapeutics Ltd | Combination |
| GB201612093D0 (en) | 2016-07-12 | 2016-08-24 | Helperby Therapeutics Ltd | Combination |
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| GB201616909D0 (en) | 2016-10-05 | 2016-11-16 | Helperby Therapeutics Ltd | Combination |
| GB201703898D0 (en) | 2017-03-10 | 2017-04-26 | Helperby Therapeautics Ltd | Method |
| GB201704620D0 (en) | 2017-03-23 | 2017-05-10 | Helperby Therapeautics Ltd | Combinations |
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| CN107021960B (zh) * | 2017-06-10 | 2018-07-31 | 上海普康药业有限公司 | 一种治疗恶性肿瘤的药物 |
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| PE20021011A1 (es) | 2001-03-23 | 2003-02-01 | Bayer Corp | Derivados quinazolinicos como inhibidores de la rho-quinasa |
| US7645878B2 (en) | 2002-03-22 | 2010-01-12 | Bayer Healthcare Llc | Process for preparing quinazoline Rho-kinase inhibitors and intermediates thereof |
| AU2003235956A1 (en) | 2002-04-26 | 2003-11-10 | Nippon Shinyaku Co., Ltd. | Quinazoline derivative and medicine |
| IL166156A0 (en) | 2002-07-09 | 2006-01-15 | Point Therapeutics Inc | Boroproline compound combination therapy |
| JP2007501809A (ja) | 2003-08-08 | 2007-02-01 | ユリシーズ・ファーマシューティカル・プロダクツ・インコーポレイテッド | 抗菌剤としてのハロゲン化キナゾリニルニトロフラン |
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- 2004-08-06 JP JP2006522859A patent/JP2007501809A/ja not_active Withdrawn
- 2004-08-06 MX MXPA06001552A patent/MXPA06001552A/es not_active Application Discontinuation
- 2004-08-06 BR BRPI0413372-2A patent/BRPI0413372A/pt not_active IP Right Cessation
- 2004-08-06 CN CNA2004800228169A patent/CN1832941A/zh active Pending
- 2004-08-06 CA CA002534405A patent/CA2534405A1/en not_active Abandoned
- 2004-08-06 EP EP04761630A patent/EP1660486A4/en not_active Withdrawn
- 2004-08-06 AU AU2004262533A patent/AU2004262533A1/en not_active Abandoned
- 2004-08-06 US US10/567,660 patent/US7410974B2/en not_active Expired - Fee Related
- 2004-08-06 WO PCT/CA2004/001466 patent/WO2005014585A1/en not_active Ceased
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|---|---|
| EP1660486A1 (en) | 2006-05-31 |
| US20060258693A1 (en) | 2006-11-16 |
| WO2005014585A8 (en) | 2005-09-09 |
| BRPI0413372A (pt) | 2006-10-17 |
| CN1832941A (zh) | 2006-09-13 |
| EP1660486A4 (en) | 2006-12-13 |
| WO2005014585A1 (en) | 2005-02-17 |
| MXPA06001552A (es) | 2006-09-04 |
| CA2534405A1 (en) | 2005-02-17 |
| US7410974B2 (en) | 2008-08-12 |
| JP2007501809A (ja) | 2007-02-01 |
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