KR20140114380A - 항미생물 요법용 트리시클릭 붕소 화합물 - Google Patents
항미생물 요법용 트리시클릭 붕소 화합물 Download PDFInfo
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- KR20140114380A KR20140114380A KR1020147019950A KR20147019950A KR20140114380A KR 20140114380 A KR20140114380 A KR 20140114380A KR 1020147019950 A KR1020147019950 A KR 1020147019950A KR 20147019950 A KR20147019950 A KR 20147019950A KR 20140114380 A KR20140114380 A KR 20140114380A
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- 150000001639 boron compounds Chemical class 0.000 title abstract description 16
- 238000011203 antimicrobial therapy Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 300
- 238000000034 method Methods 0.000 claims abstract description 71
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 45
- -1 amino, methyl Chemical group 0.000 claims description 26
- 208000015181 infectious disease Diseases 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 244000005700 microbiome Species 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 7
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 6
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- 230000000813 microbial effect Effects 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
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- 239000012634 fragment Substances 0.000 claims description 5
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
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- 208000027531 mycobacterial infectious disease Diseases 0.000 claims 1
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- 235000019439 ethyl acetate Nutrition 0.000 description 54
- 238000002360 preparation method Methods 0.000 description 54
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- 230000000694 effects Effects 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 26
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- 239000003814 drug Substances 0.000 description 23
- 239000003480 eluent Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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- 230000009467 reduction Effects 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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- 239000002585 base Substances 0.000 description 17
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- 0 CC(C*1)(N)OB(*)c2c1cccc2 Chemical compound CC(C*1)(N)OB(*)c2c1cccc2 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
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- 239000012267 brine Substances 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 125000005843 halogen group Chemical group 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
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- 238000012360 testing method Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QNYBOILAKBSWFG-SNVBAGLBSA-N (2s)-2-(phenylmethoxymethyl)oxirane Chemical compound C([C@H]1OC1)OCC1=CC=CC=C1 QNYBOILAKBSWFG-SNVBAGLBSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 7
- 125000002619 bicyclic group Chemical group 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
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- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003419 tautomerization reaction Methods 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 239000003826 tablet Substances 0.000 description 5
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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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
-
- 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
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161579271P | 2011-12-22 | 2011-12-22 | |
| US61/579,271 | 2011-12-22 | ||
| PCT/IB2012/002880 WO2013093615A1 (en) | 2011-12-22 | 2012-12-20 | Tricyclic boron compounds for antimicrobial therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140114380A true KR20140114380A (ko) | 2014-09-26 |
Family
ID=47664367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147019950A Withdrawn KR20140114380A (ko) | 2011-12-22 | 2012-12-20 | 항미생물 요법용 트리시클릭 붕소 화합물 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8530452B2 (enExample) |
| EP (1) | EP2793901A1 (enExample) |
| JP (1) | JP6031122B2 (enExample) |
| KR (1) | KR20140114380A (enExample) |
| CN (1) | CN104136032B (enExample) |
| CA (1) | CA2858799A1 (enExample) |
| WO (1) | WO2013093615A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10444284B2 (en) | 2016-12-22 | 2019-10-15 | Lsis Co., Ltd. | Diagnostic apparatus for switchgear |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2950644B1 (en) * | 2013-01-30 | 2017-07-19 | AgroFresh Inc. | Use of benzoxaboroles as volatile antimicrobial agents on meats, plants, or plant parts |
| 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 |
| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| US9585396B2 (en) | 2013-01-30 | 2017-03-07 | Agrofresh Inc. | Volatile applications against pathogens |
| KR101636431B1 (ko) | 2013-07-30 | 2016-07-05 | 동아에스티 주식회사 | 트리사이클릭 벤즈옥사보롤 화합물, 이의 제조방법 및 용도 |
| WO2015021396A2 (en) * | 2013-08-09 | 2015-02-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Tricyclic benzoxaborole compounds and uses thereof |
| EA038093B1 (ru) * | 2013-12-20 | 2021-07-05 | Глаксосмитклайн Интеллекчуал Проперти (№2) Лимитед | Способ лечения заболевания, вызванного инфекцией комплекса mycobacterium tuberculosis, с использованием (s)-(3-хлор-7,8-дигидро-2h-1,6,9-триокса-9a-борабензо[cd]азулен-2-ил)метанамина или его фармацевтически приемлемой соли |
| ES2732465T3 (es) * | 2014-07-01 | 2019-11-22 | Daiichi Sankyo Co Ltd | Benzoxaboroles tricíclicos como agentes antibacterianos |
| CN104177226A (zh) * | 2014-07-31 | 2014-12-03 | 河北国蓬化工有限公司 | 一种聚醚用催化剂的制备方法 |
| MA41495A (fr) | 2015-02-12 | 2017-12-19 | Anacor Pharmaceuticals Inc | Composés benzoxaborole et leurs utilisations |
| EP3426029B1 (en) | 2016-03-07 | 2023-08-30 | AgroFresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| WO2021029836A1 (en) | 2019-08-09 | 2021-02-18 | Safaş Saf Plasti̇k Sanayi̇ Ve Ti̇caret Anoni̇m Şi̇rketi̇ | Boron-modified flexible polyurethane foam for hygiene and a method of production therefor |
| JP2025520237A (ja) | 2022-06-23 | 2025-07-03 | ミクウルク ファーマシューティカルズ， インコーポレイテッド | ホウ素化合物を用いて非結核性マイコバクテリア感染症を治療する方法及びその用途、並びに同じ疾患を治療するための医薬組成物 |
| CA3239097A1 (en) * | 2022-06-23 | 2023-12-28 | Shanghai Micurx Pharmaceutical Co., Ltd. | Prodrugs of boron compounds and their use in treating bacterial infections |
| WO2025140370A1 (zh) * | 2023-12-27 | 2025-07-03 | 上海盟科药业股份有限公司 | 硼化合物前药的盐型、晶型及其药物组合物和用途 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235871A (en) | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
| US4501728A (en) | 1983-01-06 | 1985-02-26 | Technology Unlimited, Inc. | Masking of liposomes from RES recognition |
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4837028A (en) | 1986-12-24 | 1989-06-06 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| WO2005013892A2 (en) | 2003-06-16 | 2005-02-17 | Anacor Pharmaceuticals, Inc. | Hydrolytically-resistant boron-containing therapeutics and methods of use |
| CA2642583C (en) * | 2006-02-16 | 2016-08-23 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-inflammatory agents |
| WO2007131072A2 (en) | 2006-05-02 | 2007-11-15 | Anacor Pharmaceuticals, Inc. | Hydrolytically-resistant boron-containing therapeutics and methods of use |
| US20070286822A1 (en) * | 2006-06-12 | 2007-12-13 | Anacor Pharmaceuticals Inc. | Compounds for the Treatment of Periodontal Disease |
| JO3396B1 (ar) * | 2007-06-20 | 2019-10-20 | Anacor Pharmaceuticals Inc | جزيئات صغيرة تحتوي على البورون |
| EP2285384A4 (en) | 2008-05-12 | 2012-04-25 | Anacor Pharmaceuticals Inc | BORN SMALL MOLECULES |
| US20110259250A1 (en) | 2008-08-21 | 2011-10-27 | Mcknight James T | Systems And Methods For Converting Biomass In The Field To A Combustible Fluid For Direct Replacement Or Supplement To Liquid Fossil Fuels |
| AU2009335744A1 (en) | 2008-12-17 | 2010-07-15 | Anacor Pharmaceuticals, Inc. | Polymorphs of (S)-3-aminomethyl-7-(3-hydroxy-propoxy) -3H-benzo[c][1,2] oxaborol-1-ol |
| JP2013500974A (ja) | 2009-07-28 | 2013-01-10 | アナコール ファーマシューティカルズ，インコーポレイテッド | 三置換ホウ素含有分子 |
| AU2011237681B2 (en) | 2010-04-07 | 2015-01-22 | Glaxosmithkline Llc | Process for preparing benzoxaboroles |
| SMT202100643T1 (it) | 2010-09-07 | 2022-01-10 | Anacor Pharmaceuticals Inc | Derivati del benzossaborolo per il trattamento delle infezioni batteriche |
-
2012
- 2012-12-20 JP JP2014548243A patent/JP6031122B2/ja not_active Expired - Fee Related
- 2012-12-20 EP EP12821181.0A patent/EP2793901A1/en not_active Withdrawn
- 2012-12-20 US US13/722,912 patent/US8530452B2/en active Active
- 2012-12-20 CA CA2858799A patent/CA2858799A1/en not_active Abandoned
- 2012-12-20 CN CN201280064147.6A patent/CN104136032B/zh active Active
- 2012-12-20 KR KR1020147019950A patent/KR20140114380A/ko not_active Withdrawn
- 2012-12-20 WO PCT/IB2012/002880 patent/WO2013093615A1/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10444284B2 (en) | 2016-12-22 | 2019-10-15 | Lsis Co., Ltd. | Diagnostic apparatus for switchgear |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6031122B2 (ja) | 2016-11-24 |
| US8530452B2 (en) | 2013-09-10 |
| JP2015502974A (ja) | 2015-01-29 |
| WO2013093615A1 (en) | 2013-06-27 |
| CN104136032B (zh) | 2018-11-13 |
| CN104136032A (zh) | 2014-11-05 |
| EP2793901A1 (en) | 2014-10-29 |
| CA2858799A1 (en) | 2013-06-27 |
| US20130165411A1 (en) | 2013-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20140717 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |