AU2014255326B2 - Antibacterial biaromatic derivatives - Google Patents
Antibacterial biaromatic derivatives Download PDFInfo
- Publication number
- AU2014255326B2 AU2014255326B2 AU2014255326A AU2014255326A AU2014255326B2 AU 2014255326 B2 AU2014255326 B2 AU 2014255326B2 AU 2014255326 A AU2014255326 A AU 2014255326A AU 2014255326 A AU2014255326 A AU 2014255326A AU 2014255326 B2 AU2014255326 B2 AU 2014255326B2
- Authority
- AU
- Australia
- Prior art keywords
- oxo
- pyrido
- oxazin
- ethyl
- methoxy
- 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
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 523
- -1 cyanomethoxy Chemical group 0.000 claims abstract description 123
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 70
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 242
- 229910052770 Uranium Inorganic materials 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims description 53
- XEKAWZARUWARND-UHFFFAOYSA-N 6h-oxazin-3-one Chemical compound O=C1NOCC=C1 XEKAWZARUWARND-UHFFFAOYSA-N 0.000 claims description 52
- GAGAICHLGQDUTL-UHFFFAOYSA-N 4h-thiazin-3-one Chemical compound O=C1CC=CSN1 GAGAICHLGQDUTL-UHFFFAOYSA-N 0.000 claims description 40
- 208000015181 infectious disease Diseases 0.000 claims description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 31
- 208000035143 Bacterial infection Diseases 0.000 claims description 29
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 26
- 230000001404 mediated effect Effects 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 230000002265 prevention Effects 0.000 claims description 19
- 229910052720 vanadium Inorganic materials 0.000 claims description 18
- 241000588626 Acinetobacter baumannii Species 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 241000191967 Staphylococcus aureus Species 0.000 claims description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 14
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 10
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 claims description 9
- 125000005518 carboxamido group Chemical group 0.000 claims description 8
- ANHQLUBMNSSPBV-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1=CN=C2NC(=O)COC2=C1 ANHQLUBMNSSPBV-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
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- 229960000649 oxyphenbutazone Drugs 0.000 claims description 6
- 206010033078 Otitis media Diseases 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 4
- 206010062255 Soft tissue infection Diseases 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000020029 respiratory tract infectious disease Diseases 0.000 claims description 4
- 206010040872 skin infection Diseases 0.000 claims description 4
- UIRSLBDCOYTZPH-UHFFFAOYSA-N 4h-1,4-thiazin-3-one Chemical compound O=C1CSC=CN1 UIRSLBDCOYTZPH-UHFFFAOYSA-N 0.000 claims description 3
- 208000031729 Bacteremia Diseases 0.000 claims description 3
- 208000016604 Lyme disease Diseases 0.000 claims description 3
- 201000009906 Meningitis Diseases 0.000 claims description 3
- 206010031252 Osteomyelitis Diseases 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 206010014665 endocarditis Diseases 0.000 claims description 3
- 208000019206 urinary tract infection Diseases 0.000 claims description 3
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 claims description 2
- GVUSWMIMPJDWNW-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound C1=CN=C2NC(=O)CSC2=C1 GVUSWMIMPJDWNW-UHFFFAOYSA-N 0.000 claims description 2
- 208000037384 Clostridium Infections Diseases 0.000 claims description 2
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- 208000036209 Intraabdominal Infections Diseases 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
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- 239000013256 coordination polymer Substances 0.000 claims 5
- ANILSVMAOYARLC-INIZCTEOSA-N COc1cnnc(c1)-c1ccnc(CNCC[C@H]2CN(C(=O)O2)c2ccc3OCC(=O)Nc3n2)c1 Chemical compound COc1cnnc(c1)-c1ccnc(CNCC[C@H]2CN(C(=O)O2)c2ccc3OCC(=O)Nc3n2)c1 ANILSVMAOYARLC-INIZCTEOSA-N 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract description 4
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- 238000002953 preparative HPLC Methods 0.000 description 116
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- 239000000543 intermediate Substances 0.000 description 69
- 230000002829 reductive effect Effects 0.000 description 64
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- 239000000243 solution Substances 0.000 description 43
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 41
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 238000001914 filtration Methods 0.000 description 25
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 19
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YLHJACXHRQQNQR-UHFFFAOYSA-N pyridine;2,4,6-tris(ethenyl)-1,3,5,2,4,6-trioxatriborinane Chemical compound C1=CC=NC=C1.C=CB1OB(C=C)OB(C=C)O1 YLHJACXHRQQNQR-UHFFFAOYSA-N 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910001544 silver hexafluoroantimonate(V) Inorganic materials 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 229940037649 staphylococcus haemolyticus Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- SLXHIJJXFFHHMS-UHFFFAOYSA-N tert-butyl n-(4-bromobut-3-ynyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCC#CBr SLXHIJJXFFHHMS-UHFFFAOYSA-N 0.000 description 1
- DAZJYWWNTKNWFP-UHFFFAOYSA-N tert-butyl n-(4-phenylmethoxybutanoylamino)carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)CCCOCC1=CC=CC=C1 DAZJYWWNTKNWFP-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
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- 229940040944 tetracyclines Drugs 0.000 description 1
- WJZPIORVERXPPR-UHFFFAOYSA-L tetramethylazanium;carbonate Chemical compound [O-]C([O-])=O.C[N+](C)(C)C.C[N+](C)(C)C WJZPIORVERXPPR-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
Classifications
-
- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- 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
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- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2013053021 | 2013-04-16 | ||
| IBPCT/IB2013/053021 | 2013-04-16 | ||
| PCT/IB2014/060724 WO2014170821A1 (en) | 2013-04-16 | 2014-04-15 | Antibacterial biaromatic derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014255326A1 AU2014255326A1 (en) | 2015-11-26 |
| AU2014255326B2 true AU2014255326B2 (en) | 2018-09-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014255326A Ceased AU2014255326B2 (en) | 2013-04-16 | 2014-04-15 | Antibacterial biaromatic derivatives |
Country Status (21)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR073774A1 (es) | 2008-10-07 | 2010-12-01 | Actelion Pharmaceuticals Ltd | Compuestos antibioticos oxazolidinona triciclicos |
| AR102256A1 (es) | 2014-10-15 | 2017-02-15 | Actelion Pharmaceuticals Ltd | Derivados biaromáticos básicos antibacterianos con sustitución de aminoalcoxi |
| 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 |
| EP3429997A1 (de) | 2016-03-16 | 2019-01-23 | Bayer CropScience Aktiengesellschaft | N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel |
| AR108108A1 (es) | 2016-04-14 | 2018-07-18 | Idorsia Pharmaceuticals Ltd | Derivados biaromáticos antibacterianos con sustitución de oxetan-3-iloxi |
| GB2550437B (en) | 2016-05-20 | 2021-06-23 | Bugworks Res Inc | Heterocyclic compounds useful as anti-bacterial agents and method for production |
| TW201833120A (zh) | 2017-02-17 | 2018-09-16 | 瑞士商愛杜西亞製藥有限公司 | 芳基噁唑啶酮抗生素化合物 |
| EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
| JP7390728B2 (ja) * | 2017-11-29 | 2023-12-04 | バグワークス・リサーチ・インコーポレイテッド | 抗菌複素環式化合物及びそれらの合成 |
| UA127629C2 (uk) | 2018-08-13 | 2023-11-08 | Ф. Хоффманн-Ля Рош Аг | Нові гетероциклічні сполуки як інгібітори моноацилгліцеролліпази |
| MX2022002311A (es) | 2019-09-12 | 2022-03-25 | Hoffmann La Roche | Compuestos de 4,4a,5,7,8,8a-hexapirido[4,3-b][1,4]oxazin-3-ona como inhibidores de monoacilglicerol lipasa (magl). |
| WO2021190727A1 (en) * | 2020-03-24 | 2021-09-30 | F. Hoffmann-La Roche Ag | Compounds and their use in the treatment of bacterial infection |
| CN115785718B (zh) * | 2022-11-25 | 2023-08-22 | 四川大学 | 一种多基底表面的金属配位抗菌涂层及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008126024A2 (en) * | 2007-04-11 | 2008-10-23 | Actelion Pharmaceuticals Ltd | Oxazolidinone antibiotic derivatives |
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| EP0297042A1 (de) | 1987-06-23 | 1988-12-28 | Ciba-Geigy Ag | Substituierte Penem-Verbindungen |
| DE19802239A1 (de) | 1998-01-22 | 1999-07-29 | Bayer Ag | Neue mit Bicyclen substituierte Oxazolidinone |
| WO2001030782A2 (en) | 1999-10-29 | 2001-05-03 | Syngenta Participations Ag | Novel herbicides |
| EP1448538A1 (en) | 2001-11-15 | 2004-08-25 | Eli Lilly And Company | Peroxisome proliferator activated receptor alpha agonists |
| TW200406413A (en) | 2002-06-26 | 2004-05-01 | Glaxo Group Ltd | Compounds |
| US20090186834A1 (en) | 2005-03-24 | 2009-07-23 | Microbia, Inc. | Diphenylheterocycle cholesterol absorption inhibitors |
| TW200734311A (en) | 2005-11-21 | 2007-09-16 | Astrazeneca Ab | New compounds |
| WO2008120655A1 (ja) | 2007-03-30 | 2008-10-09 | Institute Of Medicinal Molecular Design, Inc. | Ｉ型１１βヒドロキシステロイド脱水素酵素阻害活性を有するオキサゾリジノン誘導体 |
| CA2710087C (en) | 2007-12-20 | 2015-06-02 | Pharma Mar, S.A. | Antitumoral compounds |
| US8349828B2 (en) | 2008-02-20 | 2013-01-08 | Actelion Pharmaceuticals Ltd. | Azatricyclic antibiotic compounds |
| EP2254887B9 (en) | 2008-02-22 | 2013-05-29 | Actelion Pharmaceuticals Ltd. | Oxazolidinone derivatives |
| MX2011000968A (es) * | 2008-08-04 | 2011-03-02 | Actelion Pharmaceuticals Ltd | Derivados de alquilaminometiloxazolidinona triciclicos. |
| AR073774A1 (es) | 2008-10-07 | 2010-12-01 | Actelion Pharmaceuticals Ltd | Compuestos antibioticos oxazolidinona triciclicos |
| EP2346862B1 (en) * | 2008-10-10 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | 2-benzothiophenyl-and 2-naphthyl-0xaz0lidin0nes and their azaisostere analogues as antibacterial agents |
| MX344529B (es) | 2011-11-08 | 2016-12-19 | Actelion Pharmaceuticals Ltd | Derivados antibioticos de 2 - oxo -oxazolidin - 3, 5 -diilo. |
-
2014
- 2014-04-15 HK HK16109490.8A patent/HK1221459A1/zh unknown
- 2014-04-15 JP JP2016508263A patent/JP6375365B2/ja not_active Expired - Fee Related
- 2014-04-15 US US14/784,602 patent/US9527867B2/en not_active Expired - Fee Related
- 2014-04-15 BR BR112015026261A patent/BR112015026261A8/pt not_active Application Discontinuation
- 2014-04-15 ES ES14721539.6T patent/ES2640482T3/es active Active
- 2014-04-15 TW TW103113729A patent/TWI631119B/zh not_active IP Right Cessation
- 2014-04-15 MA MA38588A patent/MA38588B1/fr unknown
- 2014-04-15 MX MX2015014576A patent/MX362338B/es active IP Right Grant
- 2014-04-15 EA EA201501025A patent/EA029361B1/ru not_active IP Right Cessation
- 2014-04-15 CN CN201480022059.9A patent/CN105143216B/zh not_active Expired - Fee Related
- 2014-04-15 AU AU2014255326A patent/AU2014255326B2/en not_active Ceased
- 2014-04-15 CA CA2907832A patent/CA2907832A1/en not_active Abandoned
- 2014-04-15 EP EP14721539.6A patent/EP2986607B1/en not_active Not-in-force
- 2014-04-15 KR KR1020157032552A patent/KR20150143720A/ko not_active Abandoned
- 2014-04-15 PL PL14721539T patent/PL2986607T3/pl unknown
- 2014-04-15 WO PCT/IB2014/060724 patent/WO2014170821A1/en not_active Ceased
- 2014-04-15 SG SG11201508479RA patent/SG11201508479RA/en unknown
- 2014-04-16 AR ARP140101625A patent/AR095884A1/es unknown
-
2015
- 2015-10-04 SA SA515361261A patent/SA515361261B1/ar unknown
- 2015-10-09 CL CL2015003019A patent/CL2015003019A1/es unknown
- 2015-10-16 PH PH12015502411A patent/PH12015502411A1/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008126024A2 (en) * | 2007-04-11 | 2008-10-23 | Actelion Pharmaceuticals Ltd | Oxazolidinone antibiotic derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1221459A1 (zh) | 2017-06-02 |
| TW201516043A (zh) | 2015-05-01 |
| MX362338B (es) | 2019-01-11 |
| AU2014255326A1 (en) | 2015-11-26 |
| TWI631119B (zh) | 2018-08-01 |
| CL2015003019A1 (es) | 2016-09-30 |
| CN105143216A (zh) | 2015-12-09 |
| PH12015502411A1 (en) | 2016-02-22 |
| MA38588B1 (fr) | 2018-04-30 |
| CA2907832A1 (en) | 2014-10-23 |
| AR095884A1 (es) | 2015-11-18 |
| JP2016516805A (ja) | 2016-06-09 |
| JP6375365B2 (ja) | 2018-08-15 |
| EP2986607A1 (en) | 2016-02-24 |
| MA38588A1 (fr) | 2017-05-31 |
| BR112015026261A2 (pt) | 2017-07-25 |
| EP2986607B1 (en) | 2017-06-14 |
| WO2014170821A1 (en) | 2014-10-23 |
| CN105143216B (zh) | 2018-04-13 |
| US20160075722A1 (en) | 2016-03-17 |
| SA515361261B1 (ar) | 2016-06-15 |
| SG11201508479RA (en) | 2015-11-27 |
| EA029361B1 (ru) | 2018-03-30 |
| MX2015014576A (es) | 2016-03-04 |
| PL2986607T3 (pl) | 2017-11-30 |
| US9527867B2 (en) | 2016-12-27 |
| KR20150143720A (ko) | 2015-12-23 |
| EA201501025A1 (ru) | 2016-08-31 |
| ES2640482T3 (es) | 2017-11-03 |
| BR112015026261A8 (pt) | 2017-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: IDORSIA PHARMACEUTICALS LTD Free format text: FORMER APPLICANT(S): ACTELION PHARMACEUTICALS LTD |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |