AU2014368619B2 - Antibacterial 1H-indazole and 1H-indole derivatives - Google Patents
Antibacterial 1H-indazole and 1H-indole derivatives Download PDFInfo
- Publication number
- AU2014368619B2 AU2014368619B2 AU2014368619A AU2014368619A AU2014368619B2 AU 2014368619 B2 AU2014368619 B2 AU 2014368619B2 AU 2014368619 A AU2014368619 A AU 2014368619A AU 2014368619 A AU2014368619 A AU 2014368619A AU 2014368619 B2 AU2014368619 B2 AU 2014368619B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- hydroxy
- butanamide
- methylsulfonyl
- indazol
- 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.)
- Ceased
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- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 16
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 454
- -1 trifluoromethoxy, amino Chemical group 0.000 claims description 265
- 125000000217 alkyl group Chemical group 0.000 claims description 125
- 238000000034 method Methods 0.000 claims description 109
- 150000003839 salts Chemical class 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 40
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 39
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 34
- 208000035143 Bacterial infection Diseases 0.000 claims description 33
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 27
- 230000002265 prevention Effects 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 19
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 18
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 6
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 3
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 156
- 238000005481 NMR spectroscopy Methods 0.000 description 133
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 97
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- 239000007787 solid Substances 0.000 description 75
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- 238000006243 chemical reaction Methods 0.000 description 63
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13198338.9 | 2013-12-19 | ||
| EP13198338 | 2013-12-19 | ||
| PCT/EP2014/078384 WO2015091741A1 (en) | 2013-12-19 | 2014-12-18 | Antibacterial 1h-indazole and 1h-indole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014368619A1 AU2014368619A1 (en) | 2016-07-28 |
| AU2014368619B2 true AU2014368619B2 (en) | 2018-11-22 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014368619A Ceased AU2014368619B2 (en) | 2013-12-19 | 2014-12-18 | Antibacterial 1H-indazole and 1H-indole derivatives |
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| EP (1) | EP3083567B1 (enExample) |
| JP (1) | JP6407288B2 (enExample) |
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| CN (1) | CN105829288B (enExample) |
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| TW (1) | TW201609641A (enExample) |
| WO (1) | WO2015091741A1 (enExample) |
| ZA (1) | ZA201604968B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| 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 |
| 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 |
| AR105646A1 (es) | 2015-08-11 | 2017-10-25 | Actelion Pharmaceuticals Ltd | Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida |
| US20190031676A1 (en) * | 2015-08-28 | 2019-01-31 | Idorsia Pharmaceuticals Ltd | Antibacterial annulated pyrrolidin-2-one derivatives |
| AR105848A1 (es) * | 2015-08-31 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados heterocíclicos antibacterianos |
| AR105889A1 (es) | 2015-09-03 | 2017-11-22 | Actelion Pharmaceuticals Ltd | Compuestos antibacterianos 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituidos |
| AR108488A1 (es) * | 2016-05-17 | 2018-08-22 | Idorsia Pharmaceuticals Ltd | Derivados 6-(buta-1,3-diin-1-il)benzo[d]tiazol |
| TW201906819A (zh) | 2017-05-25 | 2019-02-16 | 日商大正製藥股份有限公司 | 新穎之咪唑衍生物 |
| WO2019086452A1 (en) * | 2017-10-31 | 2019-05-09 | Idorsia Pharmaceuticals Ltd | Antibacterial heteroaromatic compounds |
| CN113666860B (zh) * | 2020-05-14 | 2024-03-15 | 鲁南制药集团股份有限公司 | 一种7-乙基色醇的制备方法 |
| CN119014415B (zh) * | 2024-08-19 | 2025-09-05 | 浙江大学 | 1-甲氧基吲哚在驱避和/或杀灭害虫中的应用 |
Citations (3)
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| WO2011045703A2 (en) * | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| WO2012120397A1 (en) * | 2011-03-07 | 2012-09-13 | Pfizer Inc. | Fluoro-pyridinone derivatives useful as antibacterial agents |
| WO2012137099A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2478374C (en) | 2002-03-13 | 2009-01-06 | Eli M. Wallace | N3 alkylated benzimidazole derivatives as mek inhibitors |
| DE102004017930A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| AU2005295441B2 (en) | 2004-10-18 | 2009-04-23 | Amgen, Inc. | Thiadiazole compounds and methods of use |
| KR100973609B1 (ko) | 2005-03-23 | 2010-08-03 | 에프. 호프만-라 로슈 아게 | ｍＧｌｕＲ2 길항제로서 아세틸렌일-피라졸로-피리미딘유도체 |
| WO2008154642A2 (en) | 2007-06-12 | 2008-12-18 | Achaogen, Inc. | Antibacterial agents |
| EP2432468A2 (en) | 2009-05-20 | 2012-03-28 | Ardea Biosciences, Inc. | Methods of modulating uric acid levels |
| PL2512474T3 (pl) | 2009-12-16 | 2015-03-31 | Pfizer | N-przyłączone pochodne kwasu hydroksamowego użyteczne jako środki przeciwbakteryjne |
| GB2483736B (en) | 2010-09-16 | 2012-08-29 | Aragon Pharmaceuticals Inc | Estrogen receptor modulators and uses thereof |
| MX2013005200A (es) | 2010-11-10 | 2013-06-28 | Achaogen Inc | Derivados de acido hidroxamico y su so en el tratamiento de infecciones bacterianas. |
| JP2014501274A (ja) | 2011-01-03 | 2014-01-20 | ハンミ ファーム． シーオー．， エルティーディー． | Ｇタンパク質共役受容体調節のための新規な二環式化合物 |
| CN103717582B (zh) | 2011-04-08 | 2015-09-30 | 辉瑞大药厂 | 用作抗菌剂的异*唑衍生物 |
| 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 |
| 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 |
| 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 |
-
2014
- 2014-12-18 TR TR2018/07881T patent/TR201807881T4/tr unknown
- 2014-12-18 CA CA2933604A patent/CA2933604A1/en not_active Abandoned
- 2014-12-18 EA EA201600475A patent/EA030730B1/ru not_active IP Right Cessation
- 2014-12-18 PL PL14812752T patent/PL3083567T3/pl unknown
- 2014-12-18 CN CN201480067976.9A patent/CN105829288B/zh not_active Expired - Fee Related
- 2014-12-18 MA MA39189A patent/MA39189A1/fr unknown
- 2014-12-18 WO PCT/EP2014/078384 patent/WO2015091741A1/en not_active Ceased
- 2014-12-18 MX MX2016007991A patent/MX360983B/es active IP Right Grant
- 2014-12-18 SG SG11201605014YA patent/SG11201605014YA/en unknown
- 2014-12-18 JP JP2016541300A patent/JP6407288B2/ja not_active Expired - Fee Related
- 2014-12-18 AU AU2014368619A patent/AU2014368619B2/en not_active Ceased
- 2014-12-18 US US15/106,790 patent/US9624206B2/en not_active Expired - Fee Related
- 2014-12-18 TW TW103144395A patent/TW201609641A/zh unknown
- 2014-12-18 ES ES14812752.5T patent/ES2666130T3/es active Active
- 2014-12-18 AR ARP140104742A patent/AR100032A1/es unknown
- 2014-12-18 BR BR112016014115A patent/BR112016014115A8/pt not_active Application Discontinuation
- 2014-12-18 KR KR1020167019669A patent/KR20160098503A/ko not_active Ceased
- 2014-12-18 EP EP14812752.5A patent/EP3083567B1/en not_active Not-in-force
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2016
- 2016-06-09 PH PH12016501102A patent/PH12016501102A1/en unknown
- 2016-06-14 IL IL246201A patent/IL246201A0/en unknown
- 2016-06-16 CL CL2016001524A patent/CL2016001524A1/es unknown
- 2016-07-18 ZA ZA2016/04968A patent/ZA201604968B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011045703A2 (en) * | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| WO2012120397A1 (en) * | 2011-03-07 | 2012-09-13 | Pfizer Inc. | Fluoro-pyridinone derivatives useful as antibacterial agents |
| WO2012137099A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
| US8809333B2 (en) * | 2011-04-08 | 2014-08-19 | Pfizer Inc. | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
Non-Patent Citations (1)
| Title |
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| LAURA A. MCALLISTER ET AL, "Heterocyclic methylsulfone hydroxamic acid LpxC inhibitors as Gram-negative antibacterial agents", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, (2012-09-24), vol. 22, no. 22, pages 6832 - 6838 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2933604A1 (en) | 2015-06-25 |
| JP6407288B2 (ja) | 2018-10-17 |
| BR112016014115A8 (pt) | 2017-12-26 |
| ES2666130T3 (es) | 2018-05-03 |
| CN105829288A (zh) | 2016-08-03 |
| EA030730B1 (ru) | 2018-09-28 |
| IL246201A0 (en) | 2016-08-02 |
| CN105829288B (zh) | 2019-01-15 |
| AR100032A1 (es) | 2016-09-07 |
| MX2016007991A (es) | 2016-10-07 |
| PH12016501102A1 (en) | 2016-07-11 |
| TW201609641A (zh) | 2016-03-16 |
| EP3083567B1 (en) | 2018-03-07 |
| TR201807881T4 (tr) | 2018-06-21 |
| AU2014368619A1 (en) | 2016-07-28 |
| WO2015091741A1 (en) | 2015-06-25 |
| MX360983B (es) | 2018-11-22 |
| EA201600475A1 (ru) | 2016-11-30 |
| CL2016001524A1 (es) | 2017-01-27 |
| SG11201605014YA (en) | 2016-07-28 |
| JP2017500336A (ja) | 2017-01-05 |
| EP3083567A1 (en) | 2016-10-26 |
| ZA201604968B (en) | 2018-11-28 |
| MA39189A1 (fr) | 2017-06-30 |
| US20170029411A1 (en) | 2017-02-02 |
| BR112016014115A2 (enExample) | 2017-08-08 |
| KR20160098503A (ko) | 2016-08-18 |
| US9624206B2 (en) | 2017-04-18 |
| PL3083567T3 (pl) | 2018-08-31 |
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| PC1 | Assignment before grant (sect. 113) |
Owner name: IDORSIA PHARMACEUTICALS LTD Free format text: FORMER APPLICANT(S): ACTELION PHARMACEUTICALS LTD |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |