CA2509645A1 - Antibiotics containing borinic acid complexes and methods of use - Google Patents
Antibiotics containing borinic acid complexes and methods of use Download PDFInfo
- Publication number
- CA2509645A1 CA2509645A1 CA002509645A CA2509645A CA2509645A1 CA 2509645 A1 CA2509645 A1 CA 2509645A1 CA 002509645 A CA002509645 A CA 002509645A CA 2509645 A CA2509645 A CA 2509645A CA 2509645 A1 CA2509645 A1 CA 2509645A1
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- CA
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- Prior art keywords
- alkyl
- substituted
- compound
- aryl
- unsubstituted
- 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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- 238000000034 method Methods 0.000 title claims abstract description 46
- UYANAUSDHIFLFQ-UHFFFAOYSA-N borinic acid Chemical class OB UYANAUSDHIFLFQ-UHFFFAOYSA-N 0.000 title abstract description 29
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 16
- 229940088710 antibiotic agent Drugs 0.000 title abstract description 16
- 241000894006 Bacteria Species 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 156
- -1 CO2alkyl Chemical group 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 20
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004288 oxazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC1([H])* 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
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- 241000186216 Corynebacterium Species 0.000 claims description 6
- 241000588653 Neisseria Species 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- 241000193985 Streptococcus agalactiae Species 0.000 claims description 3
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- 241000607598 Vibrio Species 0.000 claims description 3
- 241000607272 Vibrio parahaemolyticus Species 0.000 claims description 3
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 2
- 229940046939 rickettsia prowazekii Drugs 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 14
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 14
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- 150000002431 hydrogen Chemical class 0.000 claims 10
- 101150020251 NR13 gene Proteins 0.000 claims 2
- 239000003814 drug Substances 0.000 abstract description 11
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract description 9
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract description 4
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- HEMGPARMYBRMGB-UHFFFAOYSA-N bis(3-chlorophenyl)borinic acid Chemical compound C=1C=CC(Cl)=CC=1B(O)C1=CC=CC(Cl)=C1 HEMGPARMYBRMGB-UHFFFAOYSA-N 0.000 description 9
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- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43437502P | 2002-12-18 | 2002-12-18 | |
| US60/434,375 | 2002-12-18 | ||
| US43609502P | 2002-12-23 | 2002-12-23 | |
| US60/436,095 | 2002-12-23 | ||
| US43784903P | 2003-01-03 | 2003-01-03 | |
| US60/437,849 | 2003-01-03 | ||
| PCT/US2003/040982 WO2004056322A2 (en) | 2002-12-18 | 2003-12-18 | Antibiotics containing borinic acid complexes and methods of use |
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| CN1325504C (zh) | 2002-01-10 | 2007-07-11 | 宾夕法尼亚州研究基金会 | 制备二芳基硼酸烷基酯和络合的二芳基硼酸的方法 |
| US7390806B2 (en) * | 2002-12-18 | 2008-06-24 | Anacor Pharmaceuticals, Inc. | Antibiotics containing borinic acid complexes and methods of use |
| MXPA05006685A (es) * | 2002-12-18 | 2005-12-14 | Anacor Pharmaceuticals Inc | Antibioticos que contienen complejos de acido borinico y metodos de uso. |
| AR049916A1 (es) * | 2004-06-14 | 2006-09-13 | Anacor Pharmaceuticals Inc | Usos anti-parasitarios de complejos de acido borinico |
| AR049915A1 (es) * | 2004-06-14 | 2006-09-13 | Anacor Pharmaceuticals Inc | Compuestos con contenido de boro y metodos de uso de los mismos |
| EP1765360B1 (en) | 2004-06-14 | 2009-11-11 | Anacor Pharmaceuticals, Inc. | Anti-viral uses of borinic acid complexes |
| US7767657B2 (en) | 2005-02-16 | 2010-08-03 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| ES2872962T3 (es) | 2005-02-16 | 2021-11-03 | Anacor Pharmaceuticals Inc | Boronoftalidas para uso terapéutico |
| MX2007011486A (es) * | 2005-03-24 | 2007-11-20 | Anacor Pharmaceuticals Inc | Formulaciones topicas de antibioticos de acido borinico y sus metodos de uso. |
| EP1965647A2 (en) * | 2005-12-28 | 2008-09-10 | Anacor Pharmaceuticals, Inc. | Process for manufacturing picolinate borinic esters |
| RU2642628C2 (ru) | 2006-02-16 | 2018-01-25 | Анакор Фармасьютикалз, Инк. | Бор-содержащие малые молекулы в качестве противовоспалительных средств |
| US20070286822A1 (en) * | 2006-06-12 | 2007-12-13 | Anacor Pharmaceuticals Inc. | Compounds for the Treatment of Periodontal Disease |
| BRPI0713010A2 (pt) * | 2006-06-12 | 2012-10-09 | Anacor Pharmaceuticals Inc | compostos para o tratamento de doença periodontal |
| EP2069370A4 (en) * | 2006-11-22 | 2011-05-04 | Anacor Pharmaceuticals Inc | MICRO-ORGANISMS KILLING COMPOUNDS |
| EP3246034A1 (en) | 2008-03-06 | 2017-11-22 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-inflammatory agents |
| US20100256092A1 (en) * | 2008-05-12 | 2010-10-07 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2010027975A1 (en) | 2008-09-04 | 2010-03-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US8461336B2 (en) | 2008-09-04 | 2013-06-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US9493489B2 (en) | 2008-10-15 | 2016-11-15 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agents |
| SG172040A1 (en) * | 2008-12-17 | 2011-07-28 | Anacor Pharmaceuticals Inc | Polymorphs of (s)-3-aminomethyl-7-(3-hydroxy-propoxy)-3h-benzo[c][1,2] oxaborol-1-ol |
| EP2458995A1 (en) | 2009-07-28 | 2012-06-06 | Anacor Pharmaceuticals, Inc. | Trisubstituted boron-containing molecules |
| AP4039A (en) | 2009-08-14 | 2017-02-28 | Daitao Chen | Boron-containing small molecules as antiprotozoal agents |
| US20110207701A1 (en) * | 2009-08-19 | 2011-08-25 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| US20110124597A1 (en) * | 2009-09-25 | 2011-05-26 | Anacor Pharmaceuticals, Inc. | Boron containing small molecules |
| WO2011049971A1 (en) | 2009-10-20 | 2011-04-28 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| US8461134B2 (en) * | 2009-11-11 | 2013-06-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US8716478B2 (en) | 2010-01-27 | 2014-05-06 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2011116348A1 (en) | 2010-03-19 | 2011-09-22 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agent |
| DK2613788T3 (en) | 2010-09-07 | 2017-08-07 | Anacor Pharmaceuticals Inc | BENZOXABOROLD DERIVATIVES FOR TREATMENT OF BACTERIA INFECTIONS |
| US8669207B1 (en) | 2013-01-30 | 2014-03-11 | Dow Agrosciences, Llc. | Compounds and compositions |
| AR094666A1 (es) | 2013-01-30 | 2015-08-19 | Dow Agrosciences Llc | Uso de benzoxaborolas como agentes antimicrobianos volátiles en carnes, plantas o partes de plantas |
| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| US11039617B2 (en) | 2013-01-30 | 2021-06-22 | Agrofresh Inc. | Large scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness |
| US9585396B2 (en) | 2013-01-30 | 2017-03-07 | Agrofresh Inc. | Volatile applications against pathogens |
| BR112016003692B1 (pt) * | 2013-08-20 | 2022-02-08 | 3M Innovative Properties Company | Complexo poliéter boro-silano |
| KR101756785B1 (ko) * | 2015-03-10 | 2017-07-12 | 한국화학연구원 | 4배위 유기 붕소 화합물의 제조방법 |
| WO2017155879A1 (en) | 2016-03-07 | 2017-09-14 | Agrofresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| US11447506B2 (en) | 2016-05-09 | 2022-09-20 | Anacor Pharmaceuticals, Inc. | Crystal forms of crisaborole in free form and preparation method and use thereof |
| IL248150B (en) | 2016-09-29 | 2018-05-31 | Garti Nissim | Method for selective extraction of cannabinoids from a plant source |
| IL248149B (en) | 2016-09-29 | 2020-03-31 | Garti Nissim | Dilutable formulations of cannbinoids and processes for their preparation |
| EP3522892A4 (en) * | 2016-10-05 | 2020-05-13 | The Global Alliance for TB Drug Development, Inc. | HETEROARYL TRIFLUORBORATE COMPOUNDS FOR TREATING MYCOBACTERIAL INFECTIONS |
| US10961261B2 (en) | 2017-03-01 | 2021-03-30 | Anacor Pharmaceuticals, Inc. | Oxaborole analogs and uses thereof |
| CA3054138A1 (en) * | 2017-03-09 | 2018-09-13 | The Penn State Research Foundation | Boron-containing small molecules for inhibiting activity of a receptor-like protein tyrosine phosphatase |
| EP3840637B1 (en) * | 2018-08-20 | 2025-08-06 | Senseonics, Incorporated | Mediated drug release for reducing in vivo analyte indicator degradation |
| WO2022043936A1 (en) | 2020-08-31 | 2022-03-03 | Pfizer Inc. | Methods of protecting rna |
| US12357552B2 (en) | 2021-03-09 | 2025-07-15 | Juris GERMANAS | Hydroxyquinoline compounds and methods of use as pigment modifying agents |
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| EP0496757B1 (de) * | 1989-10-18 | 1995-07-12 | Hoechst Schering AgrEvo GmbH | Verfahren zur bekämpfung von schadpflanzen in reis |
| US5348947A (en) * | 1993-05-07 | 1994-09-20 | American Cyanamid Company | Diarylboron ester and thioester fungicidal agents |
| US5348948A (en) * | 1993-05-07 | 1994-09-20 | American Cyanamid Company | 2,2-diaryl-1-(oxa and thia)-2a-azonia-2-borataacenaphthene fungicidal |
| JPH0952893A (ja) * | 1995-08-10 | 1997-02-25 | Yoshitomi Pharmaceut Ind Ltd | キノロンカルボン酸誘導体の工業的な製造法およびその合成中間体 |
| DE19829947A1 (de) * | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnungen mit Bor-Chelaten |
| EP1155698A4 (en) * | 1999-01-29 | 2003-01-15 | Nitto Kasei Co Ltd | ORGANOBORAL COMPOUNDS HAVING COCCIDIOSTAT ACTIVITY |
| CN1370170A (zh) * | 1999-05-25 | 2002-09-18 | 宾夕法尼亚州研究基金会 | Dna甲基转移酶抑制剂 |
| DE10110051C2 (de) * | 2001-03-02 | 2003-07-03 | Clariant Gmbh | Verfahren zur Herstellung von Boron- und Borinsäuren |
| JP2002322007A (ja) * | 2001-04-27 | 2002-11-08 | Shionogi & Co Ltd | 有機ホウ素化合物を含有する植物用殺線虫剤 |
| CN1325504C (zh) * | 2002-01-10 | 2007-07-11 | 宾夕法尼亚州研究基金会 | 制备二芳基硼酸烷基酯和络合的二芳基硼酸的方法 |
| MXPA05006685A (es) * | 2002-12-18 | 2005-12-14 | Anacor Pharmaceuticals Inc | Antibioticos que contienen complejos de acido borinico y metodos de uso. |
| US7390806B2 (en) * | 2002-12-18 | 2008-06-24 | Anacor Pharmaceuticals, Inc. | Antibiotics containing borinic acid complexes and methods of use |
-
2003
- 2003-12-18 MX MXPA05006685A patent/MXPA05006685A/es active IP Right Grant
- 2003-12-18 CN CN2010101656749A patent/CN101928295A/zh active Pending
- 2003-12-18 AU AU2003299821A patent/AU2003299821B2/en not_active Ceased
- 2003-12-18 KR KR1020057011194A patent/KR20050084378A/ko not_active Ceased
- 2003-12-18 EP EP03800095A patent/EP1581500A4/en not_active Withdrawn
- 2003-12-18 JP JP2005502662A patent/JP2006511613A/ja not_active Withdrawn
- 2003-12-18 US US10/740,304 patent/US20040224923A1/en not_active Abandoned
- 2003-12-18 WO PCT/US2003/040982 patent/WO2004056322A2/en not_active Ceased
- 2003-12-18 NZ NZ540870A patent/NZ540870A/en not_active IP Right Cessation
- 2003-12-18 CA CA002509645A patent/CA2509645A1/en not_active Abandoned
- 2003-12-18 EP EP08155302A patent/EP1980564A1/en not_active Withdrawn
- 2003-12-18 BR BR0317564-2A patent/BR0317564A/pt not_active IP Right Cessation
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2007
- 2007-09-06 US US11/851,259 patent/US20080146803A1/en not_active Abandoned
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2009
- 2009-02-02 JP JP2009021716A patent/JP2009161540A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20040224923A1 (en) | 2004-11-11 |
| EP1980564A1 (en) | 2008-10-15 |
| AU2003299821A1 (en) | 2004-07-14 |
| NZ540870A (en) | 2008-09-26 |
| EP1581500A2 (en) | 2005-10-05 |
| EP1581500A4 (en) | 2008-03-05 |
| MXPA05006685A (es) | 2005-12-14 |
| KR20050084378A (ko) | 2005-08-26 |
| WO2004056322A3 (en) | 2004-09-16 |
| WO2004056322A2 (en) | 2004-07-08 |
| CN101928295A (zh) | 2010-12-29 |
| US20080146803A1 (en) | 2008-06-19 |
| AU2003299821B2 (en) | 2010-02-18 |
| JP2009161540A (ja) | 2009-07-23 |
| JP2006511613A (ja) | 2006-04-06 |
| BR0317564A (pt) | 2005-11-22 |
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