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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- 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
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 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
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
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- 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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Oncology (AREA)
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- Urology & Nephrology (AREA)
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- Pulmonology (AREA)
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- Dermatology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (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)
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| IB2013053021 | 2013-04-16 | ||
| IBPCT/IB2013/053021 | 2013-04-16 | ||
| PCT/IB2014/060724 WO2014170821A1 (en) | 2013-04-16 | 2014-04-15 | Antibacterial biaromatic derivatives |
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| AU2014255326A1 AU2014255326A1 (en) | 2015-11-26 |
| AU2014255326B2 true AU2014255326B2 (en) | 2018-09-13 |
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| EP (1) | EP2986607B1 (https=) |
| JP (1) | JP6375365B2 (https=) |
| KR (1) | KR20150143720A (https=) |
| CN (1) | CN105143216B (https=) |
| AR (1) | AR095884A1 (https=) |
| AU (1) | AU2014255326B2 (https=) |
| BR (1) | BR112015026261A8 (https=) |
| CA (1) | CA2907832A1 (https=) |
| CL (1) | CL2015003019A1 (https=) |
| EA (1) | EA029361B1 (https=) |
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| SG (1) | SG11201508479RA (https=) |
| TW (1) | TWI631119B (https=) |
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| BRPI0920895A8 (pt) | 2008-10-07 | 2017-12-26 | Actelion Pharmaceuticals Ltd | Compostos antibióticos de oxazolidinona tricíclica |
| AR102256A1 (es) * | 2014-10-15 | 2017-02-15 | Actelion Pharmaceuticals Ltd | Derivados biaromáticos básicos antibacterianos con sustitución de aminoalcoxi |
| UY36851A (es) | 2015-08-16 | 2017-03-31 | Glaxosmithkline Ip Dev Ltd | Compuestos para uso en aplicaciones antibacterianas |
| CN109071444A (zh) | 2016-03-16 | 2018-12-21 | 拜耳作物科学股份公司 | 作为农药和植物保护剂的n-(氰苄基)-6-(环丙基-羰基氨基)-4-(苯基)-吡啶-2-羧酰胺衍生物及相关化合物 |
| 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 |
| WO2019106693A1 (en) * | 2017-11-29 | 2019-06-06 | Bugworks Research India Pvt Ltd | Anti-bacterial heterocyclic compounds and their synthesis |
| ES2986417T3 (es) | 2018-08-13 | 2024-11-11 | Hoffmann La Roche | Nuevos compuestos heterocíclicos como inhibidores de la monoacilglicerol lipasa |
| ES2955037T3 (es) | 2018-11-22 | 2023-11-28 | Hoffmann La Roche | Nuevos compuestos heterocíclicos |
| EP4028403B1 (en) | 2019-09-12 | 2023-11-22 | F. Hoffmann-La Roche AG | 4,4a,5,7,8,8a-hexapyrido[4,3-b][1,4]oxazin-3-one compounds as magl inhibitors |
| CN115298176A (zh) * | 2020-03-24 | 2022-11-04 | 豪夫迈·罗氏有限公司 | 化合物以及它们在治疗细菌感染中的用途 |
| 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 |
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| 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 |
| AU1026901A (en) | 1999-10-29 | 2001-05-08 | Syngenta Participations Ag | Novel herbicides |
| US7205321B2 (en) | 2001-11-15 | 2007-04-17 | 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 |
| US7998992B2 (en) | 2007-03-30 | 2011-08-16 | Institute Of Medicinal Molecular Design, Inc. | Oxazolidinone derivative having inhibitory activity on 11β-hydroxysteroid dehydrogenase type 1 |
| PT2231633E (pt) | 2007-12-20 | 2014-01-20 | Pharma Mar Sa | Compostos antitumorais |
| ES2411930T3 (es) | 2008-02-20 | 2013-07-09 | Actelion Pharmaceuticals Ltd. | Compuestos antibióticos azatricíclicos |
| RU2501799C2 (ru) | 2008-02-22 | 2013-12-20 | Актелион Фармасьютикалз Лтд | Поизводные оксазолидинона |
| ES2399499T3 (es) * | 2008-08-04 | 2013-04-01 | Actelion Pharmaceuticals Ltd. | Derivados de alquilaminometiloxazolidinona tricíclicos |
| BRPI0920895A8 (pt) | 2008-10-07 | 2017-12-26 | Actelion Pharmaceuticals Ltd | Compostos antibióticos de oxazolidinona tricíclica |
| WO2010041219A1 (en) | 2008-10-10 | 2010-04-15 | Actelion Pharmaceuticals Ltd | 2-benzothiophenyl-and 2-naphthyl-0xaz0lidin0nes and their azaisostere analogues as antibacterial agents |
| IN2014CN04126A (https=) | 2011-11-08 | 2015-07-10 | Actelion Pharmaceuticals Ltd |
-
2014
- 2014-04-15 PL PL14721539T patent/PL2986607T3/pl unknown
- 2014-04-15 HK HK16109490.8A patent/HK1221459A1/zh unknown
- 2014-04-15 EP EP14721539.6A patent/EP2986607B1/en not_active Not-in-force
- 2014-04-15 AU AU2014255326A patent/AU2014255326B2/en not_active Ceased
- 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 CA CA2907832A patent/CA2907832A1/en not_active Abandoned
- 2014-04-15 ES ES14721539.6T patent/ES2640482T3/es active Active
- 2014-04-15 KR KR1020157032552A patent/KR20150143720A/ko not_active Abandoned
- 2014-04-15 MX MX2015014576A patent/MX362338B/es active IP Right Grant
- 2014-04-15 BR BR112015026261A patent/BR112015026261A8/pt not_active Application Discontinuation
- 2014-04-15 US US14/784,602 patent/US9527867B2/en not_active Expired - Fee Related
- 2014-04-15 WO PCT/IB2014/060724 patent/WO2014170821A1/en not_active Ceased
- 2014-04-15 CN CN201480022059.9A patent/CN105143216B/zh not_active Expired - Fee Related
- 2014-04-15 JP JP2016508263A patent/JP6375365B2/ja not_active Expired - Fee Related
- 2014-04-15 EA EA201501025A patent/EA029361B1/ru not_active IP Right Cessation
- 2014-04-15 SG SG11201508479RA patent/SG11201508479RA/en unknown
- 2014-04-16 AR ARP140101625A patent/AR095884A1/es unknown
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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 |
|---|---|
| EA029361B1 (ru) | 2018-03-30 |
| WO2014170821A1 (en) | 2014-10-23 |
| HK1221459A1 (zh) | 2017-06-02 |
| CL2015003019A1 (es) | 2016-09-30 |
| CN105143216B (zh) | 2018-04-13 |
| MA38588B1 (fr) | 2018-04-30 |
| EA201501025A1 (ru) | 2016-08-31 |
| JP6375365B2 (ja) | 2018-08-15 |
| PH12015502411A1 (en) | 2016-02-22 |
| BR112015026261A2 (pt) | 2017-07-25 |
| AU2014255326A1 (en) | 2015-11-26 |
| MA38588A1 (fr) | 2017-05-31 |
| MX362338B (es) | 2019-01-11 |
| TW201516043A (zh) | 2015-05-01 |
| CA2907832A1 (en) | 2014-10-23 |
| PL2986607T3 (pl) | 2017-11-30 |
| JP2016516805A (ja) | 2016-06-09 |
| BR112015026261A8 (pt) | 2017-12-26 |
| SG11201508479RA (en) | 2015-11-27 |
| ES2640482T3 (es) | 2017-11-03 |
| US20160075722A1 (en) | 2016-03-17 |
| KR20150143720A (ko) | 2015-12-23 |
| SA515361261B1 (ar) | 2016-06-15 |
| TWI631119B (zh) | 2018-08-01 |
| EP2986607B1 (en) | 2017-06-14 |
| AR095884A1 (es) | 2015-11-18 |
| MX2015014576A (es) | 2016-03-04 |
| CN105143216A (zh) | 2015-12-09 |
| EP2986607A1 (en) | 2016-02-24 |
| US9527867B2 (en) | 2016-12-27 |
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| Date | Code | Title | Description |
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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 |