AU2016307969C1 - Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system - Google Patents
Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system Download PDFInfo
- Publication number
- AU2016307969C1 AU2016307969C1 AU2016307969A AU2016307969A AU2016307969C1 AU 2016307969 C1 AU2016307969 C1 AU 2016307969C1 AU 2016307969 A AU2016307969 A AU 2016307969A AU 2016307969 A AU2016307969 A AU 2016307969A AU 2016307969 C1 AU2016307969 C1 AU 2016307969C1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- amino
- pyrazino
- compound
- fluoro
- 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
Links
- 0 C*1(C)C(C(**)=C(*)**2)=C2*=**1 Chemical compound C*1(C)C(C(**)=C(*)**2)=C2*=**1 0.000 description 3
- AETOSEGDBPUISS-UHFFFAOYSA-N C=Cc(nc1N2)cnc1OCC2=O Chemical compound C=Cc(nc1N2)cnc1OCC2=O AETOSEGDBPUISS-UHFFFAOYSA-N 0.000 description 1
- YKDJJXDRAVFEBJ-AWEZNQCLSA-N CC(C)(C)OC(NC[C@H]1CN(CCN2c(nc(cc3)OC)c3N=CC2=O)CC1)=O Chemical compound CC(C)(C)OC(NC[C@H]1CN(CCN2c(nc(cc3)OC)c3N=CC2=O)CC1)=O YKDJJXDRAVFEBJ-AWEZNQCLSA-N 0.000 description 1
- VMLVROAZOLUKIS-YLQAJVPDSA-N CC(C)(C)OC(N[C@@H](CC[C@@H]1NCc(c2nc(OC)cnc2cc2)c2F)C[C@H]1O)=O Chemical compound CC(C)(C)OC(N[C@@H](CC[C@@H]1NCc(c2nc(OC)cnc2cc2)c2F)C[C@H]1O)=O VMLVROAZOLUKIS-YLQAJVPDSA-N 0.000 description 1
- ZZDDFYQGRQTLBG-UHFFFAOYSA-N CCOC(C(C(OCC)=O)=CNc(c(F)c1)cc(Br)c1F)=O Chemical compound CCOC(C(C(OCC)=O)=CNc(c(F)c1)cc(Br)c1F)=O ZZDDFYQGRQTLBG-UHFFFAOYSA-N 0.000 description 1
- MSZMNCVNHGPEKB-UHFFFAOYSA-N CCOC(C(C(c1c(c(F)c2)Br)=O)=CNc1c2F)=O Chemical compound CCOC(C(C(c1c(c(F)c2)Br)=O)=CNc1c2F)=O MSZMNCVNHGPEKB-UHFFFAOYSA-N 0.000 description 1
- ILTHSAAOEREORW-UHFFFAOYSA-N CN1c(nc(cc2)OC)c2N=CC1=O Chemical compound CN1c(nc(cc2)OC)c2N=CC1=O ILTHSAAOEREORW-UHFFFAOYSA-N 0.000 description 1
- NSWVYPKCELOMKY-UHFFFAOYSA-N CN1c2nc(OC)ccc2C=CC1=O Chemical compound CN1c2nc(OC)ccc2C=CC1=O NSWVYPKCELOMKY-UHFFFAOYSA-N 0.000 description 1
- OOACEHZOTHYGGY-UHFFFAOYSA-N CN1c2nc(OC)cnc2C=CC1=O Chemical compound CN1c2nc(OC)cnc2C=CC1=O OOACEHZOTHYGGY-UHFFFAOYSA-N 0.000 description 1
- GSBXKPFJTLPTSV-UHFFFAOYSA-N CNc(c(nc(cc1)OC)c1c(F)c1)c1F Chemical compound CNc(c(nc(cc1)OC)c1c(F)c1)c1F GSBXKPFJTLPTSV-UHFFFAOYSA-N 0.000 description 1
- NVVNGHZDVMJDDH-UHFFFAOYSA-N CNc1nccc(cc2)c1nc2OC Chemical compound CNc1nccc(cc2)c1nc2OC NVVNGHZDVMJDDH-UHFFFAOYSA-N 0.000 description 1
- UZXXYQWIOOQURO-UHFFFAOYSA-N COC(c(nc(c(OC1)n2)NC1=O)c2Br)=O Chemical compound COC(c(nc(c(OC1)n2)NC1=O)c2Br)=O UZXXYQWIOOQURO-UHFFFAOYSA-N 0.000 description 1
- RKLLFGBBKXZCAB-UHFFFAOYSA-N COc(cc1F)cc2c1nccc2I Chemical compound COc(cc1F)cc2c1nccc2I RKLLFGBBKXZCAB-UHFFFAOYSA-N 0.000 description 1
- JAMSVDVSKVCYEJ-UHFFFAOYSA-N COc(ccc1c(cc2F)F)nc1c2I Chemical compound COc(ccc1c(cc2F)F)nc1c2I JAMSVDVSKVCYEJ-UHFFFAOYSA-N 0.000 description 1
- NVLXYZOTINRMRQ-UHFFFAOYSA-N COc(ccc1ncc2)cc1c2I Chemical compound COc(ccc1ncc2)cc1c2I NVLXYZOTINRMRQ-UHFFFAOYSA-N 0.000 description 1
- POIRWQKWVBCDKG-UHFFFAOYSA-N COc(nc12)ccc1ncc(F)c2I Chemical compound COc(nc12)ccc1ncc(F)c2I POIRWQKWVBCDKG-UHFFFAOYSA-N 0.000 description 1
- CKJHESVYZJITQQ-UHFFFAOYSA-N COc(nc12)ccc1nccc2I Chemical compound COc(nc12)ccc1nccc2I CKJHESVYZJITQQ-UHFFFAOYSA-N 0.000 description 1
- JRPRUNNJFWRSQJ-UHFFFAOYSA-N COc1ccc(c(F)ccc2I)c2n1 Chemical compound COc1ccc(c(F)ccc2I)c2n1 JRPRUNNJFWRSQJ-UHFFFAOYSA-N 0.000 description 1
- KTLKSJUXFMJBGO-UHFFFAOYSA-N COc1ccc(cccc2I)c2n1 Chemical compound COc1ccc(cccc2I)c2n1 KTLKSJUXFMJBGO-UHFFFAOYSA-N 0.000 description 1
- UVSZTOQVAVLPLY-XYPYZODXSA-N COc1cnc(ccc(F)c2CN[C@H](CC3)CC[C@@H]3N)c2n1 Chemical compound COc1cnc(ccc(F)c2CN[C@H](CC3)CC[C@@H]3N)c2n1 UVSZTOQVAVLPLY-XYPYZODXSA-N 0.000 description 1
- JKZUGQDQSVKMIE-UHFFFAOYSA-N COc1nc(c(I)c(cc2)F)c2cc1 Chemical compound COc1nc(c(I)c(cc2)F)c2cc1 JKZUGQDQSVKMIE-UHFFFAOYSA-N 0.000 description 1
- ARWYAWKWPGRQHX-KNTRFNDTSA-N C[C@@H](c1ccccc1)N[C@@H](CC[C@@H](C1)NOC(c2ccccc2)=O)[C@H]1O Chemical compound C[C@@H](c1ccccc1)N[C@@H](CC[C@@H](C1)NOC(c2ccccc2)=O)[C@H]1O ARWYAWKWPGRQHX-KNTRFNDTSA-N 0.000 description 1
- ARWYAWKWPGRQHX-YGWPLHOASA-N C[C@@H](c1ccccc1)N[C@H](CC[C@H](C1)NOC(c2ccccc2)=O)[C@@H]1O Chemical compound C[C@@H](c1ccccc1)N[C@H](CC[C@H](C1)NOC(c2ccccc2)=O)[C@@H]1O ARWYAWKWPGRQHX-YGWPLHOASA-N 0.000 description 1
- ZRYQANAKIAPMPW-UHFFFAOYSA-N Cc(cc1)c(ccc(OC)c2)c2c1NC Chemical compound Cc(cc1)c(ccc(OC)c2)c2c1NC ZRYQANAKIAPMPW-UHFFFAOYSA-N 0.000 description 1
- FQZCUAASVCIWSL-UHFFFAOYSA-N Nc(cc(c(F)c1)Br)c1F Chemical compound Nc(cc(c(F)c1)Br)c1F FQZCUAASVCIWSL-UHFFFAOYSA-N 0.000 description 1
- NMHHNWXOHNOHBJ-UHFFFAOYSA-N O=C1Nc(nc(CNC2CCCCC2)cn2)c2OC1 Chemical compound O=C1Nc(nc(CNC2CCCCC2)cn2)c2OC1 NMHHNWXOHNOHBJ-UHFFFAOYSA-N 0.000 description 1
- BZTYGYDSIJOIJQ-UHFFFAOYSA-N O=C1Nc(nc(cn2)Cl)c2OC1 Chemical compound O=C1Nc(nc(cn2)Cl)c2OC1 BZTYGYDSIJOIJQ-UHFFFAOYSA-N 0.000 description 1
- AXVPMSMOPJYOCS-UHFFFAOYSA-N O=Cc(nc1N2)cnc1OCC2=O Chemical compound O=Cc(nc1N2)cnc1OCC2=O AXVPMSMOPJYOCS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
-
- 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
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2019200226A AU2019200226B2 (en) | 2015-08-16 | 2019-01-14 | Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562205732P | 2015-08-16 | 2015-08-16 | |
| US62/205,732 | 2015-08-16 | ||
| US201662308928P | 2016-03-16 | 2016-03-16 | |
| US62/308,928 | 2016-03-16 | ||
| PCT/IB2016/054890 WO2017029602A2 (en) | 2015-08-16 | 2016-08-15 | Compounds for use in antibacterial applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2019200226A Division AU2019200226B2 (en) | 2015-08-16 | 2019-01-14 | Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2016307969A1 AU2016307969A1 (en) | 2018-03-08 |
| AU2016307969B2 AU2016307969B2 (en) | 2019-02-14 |
| AU2016307969C1 true AU2016307969C1 (en) | 2019-09-05 |
Family
ID=57218948
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016307969A Ceased AU2016307969C1 (en) | 2015-08-16 | 2016-08-15 | Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system |
| AU2019200226A Ceased AU2019200226B2 (en) | 2015-08-16 | 2019-01-14 | Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2019200226A Ceased AU2019200226B2 (en) | 2015-08-16 | 2019-01-14 | Antibacterial agents comprising a pyrazino[2,3-b][1,4]oxazin-3-one or a related ring system |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US10364254B2 (enExample) |
| EP (1) | EP3334739A2 (enExample) |
| JP (1) | JP6757402B2 (enExample) |
| KR (1) | KR20180038046A (enExample) |
| CN (1) | CN108137616B (enExample) |
| AU (2) | AU2016307969C1 (enExample) |
| CA (1) | CA2995715A1 (enExample) |
| CL (1) | CL2018000403A1 (enExample) |
| CO (1) | CO2018002204A2 (enExample) |
| CR (1) | CR20180111A (enExample) |
| DO (1) | DOP2018000049A (enExample) |
| EA (1) | EA033314B1 (enExample) |
| HK (1) | HK1248680A1 (enExample) |
| IL (1) | IL257265B (enExample) |
| MA (1) | MA42621A (enExample) |
| MX (1) | MX2018002033A (enExample) |
| PE (1) | PE20181143A1 (enExample) |
| PH (1) | PH12018500358A1 (enExample) |
| TW (1) | TW201722965A (enExample) |
| UY (1) | UY36851A (enExample) |
| WO (1) | WO2017029602A2 (enExample) |
| ZA (1) | ZA201800722B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201722965A (zh) * | 2015-08-16 | 2017-07-01 | 葛蘭素史密斯克藍智慧財產發展有限公司 | 用於抗菌應用之化合物 |
| WO2019180634A1 (en) | 2018-03-23 | 2019-09-26 | Glaxosmithkline Intellectual Property Development Limited | Synthesis of oxazinone-containing bicyclic aromatic and heteroaromatic aldehydes |
| TW202116782A (zh) | 2019-07-16 | 2021-05-01 | 瑞士商愛杜西亞製藥有限公司 | 喹啉酮衍生物 |
| CN111269247B (zh) * | 2020-03-04 | 2020-11-24 | 河南科技大学第一附属医院 | 具有抑制大肠杆菌作用的噻嗪酮药物分子的制备方法 |
| US20250214980A1 (en) | 2022-03-14 | 2025-07-03 | Slap Pharmaceuticals Llc | Multicyclic compounds |
| WO2025132870A1 (en) | 2023-12-21 | 2025-06-26 | Glaxosmithkline Intellectual Property (No.4) Limited | Chemical compounds and uses thereof |
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| WO2004002490A2 (en) * | 2002-06-26 | 2004-01-08 | Glaxo Group Limited | Piperidine compounds as antibacterials |
| WO2004002992A1 (en) * | 2002-06-26 | 2004-01-08 | Glaxo Group Limited | Compounds |
| WO2004087145A2 (en) * | 2003-03-27 | 2004-10-14 | Glaxo Group Limited | Antibacterial agents |
| WO2006081264A1 (en) * | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
| WO2007093963A1 (en) * | 2006-02-15 | 2007-08-23 | Actelion Pharmaceuticals Ltd | Ethanol or 1,2-ethanediol cyclohexyl antibiotic derivatives |
| WO2008078305A2 (en) * | 2006-12-22 | 2008-07-03 | Actelion Pharmaceuticals Ltd | 4-(1-amino-ethyl)-cyclohexylamine derivatives |
| WO2008128961A1 (en) * | 2007-04-20 | 2008-10-30 | Glaxo Group Limited | Compounds |
| US20090131444A1 (en) * | 2005-05-24 | 2009-05-21 | Astrazeneca Ab | Aminopiperidine Quinolines and Their Azaisosteric Analogues with Antibacterial Activity |
| US20090270374A1 (en) * | 2006-07-20 | 2009-10-29 | Llius Ballell | Derivatives and analogs of n-ethylquinolones and n-ethylazaquinolones |
| WO2010046388A1 (en) * | 2008-10-23 | 2010-04-29 | Glaxo Group Limited | Substituted (aza) -1-methyl-1h-quinolin-2-ones as antibacterials |
| WO2010055348A1 (en) * | 2008-11-14 | 2010-05-20 | Astrazeneca Ab | [4- (1-amino-ethyl) -cyclohexyl] -methyl-amines as antibacterials |
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| US20140243302A1 (en) * | 2011-06-27 | 2014-08-28 | Merck Sharp & Dohme Corporation | Bridged bicyclic compounds for the treatment of bacterial infections |
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