TW201249786A - Antibacterial agents - Google Patents
Antibacterial agents Download PDFInfo
- Publication number
- TW201249786A TW201249786A TW100140449A TW100140449A TW201249786A TW 201249786 A TW201249786 A TW 201249786A TW 100140449 A TW100140449 A TW 100140449A TW 100140449 A TW100140449 A TW 100140449A TW 201249786 A TW201249786 A TW 201249786A
- Authority
- TW
- Taiwan
- Prior art keywords
- amino
- methyl
- cyclopropyl
- diynyl
- trans
- Prior art date
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- 239000003242 anti bacterial agent Substances 0.000 title claims description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 15
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 126
- -1 cyclopropyl hydrazin- Chemical compound 0.000 claims description 92
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 82
- 241000894006 Bacteria Species 0.000 claims description 37
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 37
- 239000003814 drug Substances 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 108010059993 Vancomycin Proteins 0.000 claims description 19
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims description 19
- 229960003165 vancomycin Drugs 0.000 claims description 19
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 19
- 230000002401 inhibitory effect Effects 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000005711 Benzoic acid Substances 0.000 claims description 15
- 235000010233 benzoic acid Nutrition 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 238000001727 in vivo Methods 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 11
- 241000588724 Escherichia coli Species 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229960001225 rifampicin Drugs 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
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- 239000001273 butane Substances 0.000 claims description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003937 drug carrier Substances 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 241001453380 Burkholderia Species 0.000 claims description 6
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 5
- 241000588923 Citrobacter Species 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000588748 Klebsiella Species 0.000 claims description 4
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 4
- 241000607142 Salmonella Species 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229940067157 phenylhydrazine Drugs 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
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- 241000588771 Morganella <proteobacterium> Species 0.000 claims description 2
- 241000607720 Serratia Species 0.000 claims description 2
- 241000607734 Yersinia <bacteria> Species 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 3
- GRADOOOISCPIDG-UHFFFAOYSA-N buta-1,3-diyne Chemical group [C]#CC#C GRADOOOISCPIDG-UHFFFAOYSA-N 0.000 claims 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- 241000589516 Pseudomonas Species 0.000 claims 1
- JQXXHWHPUNPDRT-BQVAUQFYSA-N chembl1523493 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2C=NN1CCN(C)CC1 JQXXHWHPUNPDRT-BQVAUQFYSA-N 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 37
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- 239000012286 potassium permanganate Substances 0.000 description 1
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- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
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- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
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- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| US41231110P | 2010-11-10 | 2010-11-10 |
Publications (1)
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| TW201249786A true TW201249786A (en) | 2012-12-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100140449A TW201249786A (en) | 2010-11-10 | 2011-11-04 | Antibacterial agents |
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| Country | Link |
|---|---|
| EP (1) | EP2638006A1 (enExample) |
| JP (1) | JP2014501716A (enExample) |
| KR (1) | KR20140023869A (enExample) |
| CN (1) | CN103298780A (enExample) |
| AR (1) | AR083760A1 (enExample) |
| AU (1) | AU2011367819A1 (enExample) |
| BR (1) | BR112013011693A2 (enExample) |
| CA (1) | CA2817211A1 (enExample) |
| EA (1) | EA201390626A1 (enExample) |
| IL (1) | IL226270A0 (enExample) |
| MX (1) | MX2013005200A (enExample) |
| SG (1) | SG190243A1 (enExample) |
| TW (1) | TW201249786A (enExample) |
| WO (1) | WO2012154204A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008154642A2 (en) | 2007-06-12 | 2008-12-18 | Achaogen, Inc. | Antibacterial agents |
| WO2013170030A1 (en) * | 2012-05-09 | 2013-11-14 | Achaogen, Inc. | Antibacterial agents |
| WO2013170165A1 (en) | 2012-05-10 | 2013-11-14 | Achaogen, Inc. | Antibacterial agents |
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| TR201807881T4 (tr) | 2013-12-19 | 2018-06-21 | Idorsia Pharmaceuticals Ltd | Antibakteriyel 1h-ındazol ve 1h-ındol türevleri. |
| AR099612A1 (es) | 2014-03-04 | 2016-08-03 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona |
| US9539305B1 (en) | 2014-03-14 | 2017-01-10 | Fleurir Abx Llc | Pristinamycin compositions, LpxC compositions, their improvements, and combinations thereof |
| JP2017515906A (ja) | 2014-05-16 | 2017-06-15 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | 抗菌性キナゾロン−４（３ｈ）−オン誘導体 |
| KR20170086079A (ko) | 2014-11-19 | 2017-07-25 | 액테리온 파마슈티칼 리미티드 | 항균성 벤조티아졸 유도체 |
| EA032138B1 (ru) | 2014-12-16 | 2019-04-30 | Новартис Аг | СОЕДИНЕНИЯ ИЗОКСАЗОЛГИДРОКСАМИНОВОЙ КИСЛОТЫ В КАЧЕСТВЕ ИНГИБИТОРОВ LpxC |
| EP3448375B1 (en) | 2016-04-25 | 2023-09-27 | Duke University | Benzoylglycine derivatives and methods of making and using same |
| CA3026356A1 (en) | 2016-06-14 | 2017-12-21 | Novartis Ag | Crystalline form of (r)-4-(5-(cyclopropylethynyl)isoxazol-3-yl)-n-hydroxy-2-methyl-2-(methylsulfonyl)butanamide as an antibacterial agent |
| WO2017223349A1 (en) | 2016-06-23 | 2017-12-28 | Achaogen, Inc. | Antibacterial agents |
| CA3090833A1 (en) * | 2018-02-10 | 2019-08-15 | Kbp Biosciences Co., Ltd. | Compound acting as antibiotics |
| CN110563611B (zh) * | 2019-09-19 | 2021-02-02 | 中国医学科学院医药生物技术研究所 | 一种异羟肟酸类衍生物及其制备方法和应用 |
| CN113957098A (zh) * | 2021-09-13 | 2022-01-21 | 湖南工业大学 | 普罗威登斯属细菌菌株在制备二价锰氧化剂中的应用 |
| CN116730870B (zh) * | 2023-08-08 | 2023-10-13 | 中国医学科学院医药生物技术研究所 | 异羟肟酸类化合物或其可药用盐、及其用途和制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5925659A (en) | 1996-05-07 | 1999-07-20 | Merck & Co., Inc. | Antibacterial agents |
| US6541276B2 (en) | 1996-10-28 | 2003-04-01 | Versicor, Inc. | Methods for solid-phase synthesis of hydroxylamine compounds and derivatives and combinatorial libraries thereof |
| WO2000061134A1 (en) | 1999-04-09 | 2000-10-19 | British Biotech Pharmaceuticals Limited | Antimicrobial agents |
| SG2012000667A (en) * | 2003-01-08 | 2015-03-30 | Univ Washington | Antibacterial agents |
| DE102006032709A1 (de) | 2006-07-14 | 2008-01-17 | BSH Bosch und Siemens Hausgeräte GmbH | Luftschallgedämmte Lebensmittelmühle |
| CN101209974A (zh) * | 2006-12-31 | 2008-07-02 | 天津药物研究院 | 异羟肟酸类衍生物及其用途 |
| WO2008154642A2 (en) * | 2007-06-12 | 2008-12-18 | Achaogen, Inc. | Antibacterial agents |
| WO2011005355A1 (en) * | 2009-05-07 | 2011-01-13 | Achaogen, Inc. | Combinations comprising a lpxc inhibitor and an antibiotic for use in the treatment of infections caused by gram-negative bacteria |
| PH12012502087A1 (en) * | 2010-04-20 | 2015-04-15 | Taisho Pharmaceutical Co Ltd | Novel hydroxamic acid derivative |
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2011
- 2011-11-04 MX MX2013005200A patent/MX2013005200A/es not_active Application Discontinuation
- 2011-11-04 AR ARP110104117A patent/AR083760A1/es not_active Application Discontinuation
- 2011-11-04 WO PCT/US2011/059280 patent/WO2012154204A1/en not_active Ceased
- 2011-11-04 AU AU2011367819A patent/AU2011367819A1/en not_active Abandoned
- 2011-11-04 CN CN2011800639128A patent/CN103298780A/zh active Pending
- 2011-11-04 BR BR112013011693A patent/BR112013011693A2/pt not_active IP Right Cessation
- 2011-11-04 EA EA201390626A patent/EA201390626A1/ru unknown
- 2011-11-04 SG SG2013036272A patent/SG190243A1/en unknown
- 2011-11-04 TW TW100140449A patent/TW201249786A/zh unknown
- 2011-11-04 EP EP11849908.6A patent/EP2638006A1/en not_active Withdrawn
- 2011-11-04 KR KR1020137012799A patent/KR20140023869A/ko not_active Withdrawn
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- 2011-11-04 JP JP2013538794A patent/JP2014501716A/ja active Pending
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|---|---|
| WO2012154204A1 (en) | 2012-11-15 |
| EA201390626A1 (ru) | 2013-12-30 |
| EP2638006A1 (en) | 2013-09-18 |
| AU2011367819A1 (en) | 2013-05-02 |
| AR083760A1 (es) | 2013-03-20 |
| JP2014501716A (ja) | 2014-01-23 |
| MX2013005200A (es) | 2013-06-28 |
| KR20140023869A (ko) | 2014-02-27 |
| CA2817211A1 (en) | 2012-11-15 |
| CN103298780A (zh) | 2013-09-11 |
| IL226270A0 (en) | 2013-07-31 |
| SG190243A1 (en) | 2013-06-28 |
| BR112013011693A2 (pt) | 2016-08-09 |
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