TWI515187B - 作為呼吸道融合病毒抗病毒劑之吲哚類 - Google Patents

作為呼吸道融合病毒抗病毒劑之吲哚類 Download PDF

Info

Publication number
TWI515187B
TWI515187B TW100146391A TW100146391A TWI515187B TW I515187 B TWI515187 B TW I515187B TW 100146391 A TW100146391 A TW 100146391A TW 100146391 A TW100146391 A TW 100146391A TW I515187 B TWI515187 B TW I515187B
Authority
TW
Taiwan
Prior art keywords
compound
group
alkyl
compound according
mmol
Prior art date
Application number
TW100146391A
Other languages
English (en)
Chinese (zh)
Other versions
TW201307325A (zh
Inventor
路威格 庫伊曼斯
山繆 丹敏
胡麗麗
提姆 喬克斯
皮耶 拉波伊森
阿德拉 塔里
山卓琳 凡德維
Original Assignee
健生科學愛爾蘭無限公司
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 健生科學愛爾蘭無限公司 filed Critical 健生科學愛爾蘭無限公司
Publication of TW201307325A publication Critical patent/TW201307325A/zh
Application granted granted Critical
Publication of TWI515187B publication Critical patent/TWI515187B/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/06Heterocyclic 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

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)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
TW100146391A 2010-12-16 2011-12-15 作為呼吸道融合病毒抗病毒劑之吲哚類 TWI515187B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP10195468 2010-12-16

Publications (2)

Publication Number Publication Date
TW201307325A TW201307325A (zh) 2013-02-16
TWI515187B true TWI515187B (zh) 2016-01-01

Family

ID=43875270

Family Applications (1)

Application Number Title Priority Date Filing Date
TW100146391A TWI515187B (zh) 2010-12-16 2011-12-15 作為呼吸道融合病毒抗病毒劑之吲哚類

Country Status (31)

Country Link
US (3) US8921560B2 (enExample)
EP (1) EP2651922B1 (enExample)
JP (2) JP5945278B2 (enExample)
KR (1) KR101914606B1 (enExample)
CN (1) CN103347875B (enExample)
AR (1) AR084335A1 (enExample)
AU (1) AU2011343256C1 (enExample)
BR (1) BR112013011949B1 (enExample)
CA (1) CA2822000C (enExample)
CL (1) CL2013001715A1 (enExample)
CY (1) CY1117763T1 (enExample)
DK (1) DK2651922T3 (enExample)
EA (1) EA022339B1 (enExample)
ES (1) ES2572258T3 (enExample)
HR (1) HRP20160533T1 (enExample)
HU (1) HUE028009T2 (enExample)
IL (1) IL225641A (enExample)
ME (1) ME02406B (enExample)
MX (1) MX339944B (enExample)
MY (1) MY163981A (enExample)
NZ (1) NZ609487A (enExample)
PH (1) PH12013500797A1 (enExample)
PL (1) PL2651922T3 (enExample)
RS (1) RS54746B1 (enExample)
SG (1) SG189866A1 (enExample)
SI (1) SI2651922T1 (enExample)
SM (1) SMT201600142B (enExample)
TW (1) TWI515187B (enExample)
UA (1) UA109792C2 (enExample)
WO (1) WO2012080447A1 (enExample)
ZA (1) ZA201304423B (enExample)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI530495B (zh) 2010-12-16 2016-04-21 健生科學愛爾蘭無限公司 苯并咪唑呼吸道融合病毒抑制劑
TWI527814B (zh) 2010-12-16 2016-04-01 健生科學愛爾蘭無限公司 作為呼吸道融合病毒抗病毒劑之氮雜苯并咪唑類
TWI541241B (zh) 2010-12-16 2016-07-11 健生科學愛爾蘭無限公司 作為呼吸道融合病毒抗病毒劑之咪唑并吡啶類
TWI515187B (zh) * 2010-12-16 2016-01-01 健生科學愛爾蘭無限公司 作為呼吸道融合病毒抗病毒劑之吲哚類
TWI501967B (zh) * 2010-12-16 2015-10-01 Janssen R&D Ireland 作為呼吸道融合病毒抗病毒劑之氮雜吲哚類
WO2013186335A1 (en) * 2012-06-15 2013-12-19 Janssen R&D Ireland 1,3 -dihydro-2h-benzimidazol-2-one derivatives substituted with heterocycles as respiratory syncytial virus antiviral agents
DK2864323T3 (en) * 2012-06-15 2017-08-14 Janssen Sciences Ireland Uc 1,3-DIHYDRO-2H-BENZIMIDAZOLE-2 UNDERIVATIVES SUBSTITUTED BY HETEROCYCLES AS ANTIVIRUS AGENTS AGAINST RESPIRATORY SYNCYTIAL VIRUS
CN104487431B (zh) * 2012-07-10 2017-06-09 弗·哈夫曼-拉罗切有限公司 治疗和预防呼吸道合胞体病毒感染的新吲唑类化合物
DK2909195T3 (en) 2012-10-16 2017-09-25 Janssen Sciences Ireland Uc ANTIVIRAL RELATIONS TO RSV
UA123854C2 (uk) 2013-08-21 2021-06-16 Аліос Біофарма, Інк. Противірусні сполуки
TWI671299B (zh) 2014-04-14 2019-09-11 愛爾蘭商健生科學愛爾蘭無限公司 作為rsv抗病毒化合物之螺脲化合物
EP3177299A4 (en) * 2014-08-05 2018-04-04 Alios Biopharma, Inc. Combination therapy for treating a paramyxovirus
MA41614A (fr) 2015-02-25 2018-01-02 Alios Biopharma Inc Composés antiviraux
MX2017011778A (es) 2015-03-13 2017-12-04 Forma Therapeutics Inc Compuestos y composiciones de alfa-cinamida como inhibidores de histona desacetilasa 8 (hdac8).
EP3324977B1 (en) 2015-07-22 2022-07-13 Enanta Pharmaceuticals, Inc. Benzodiazepine derivatives as rsv inhibitors
IL300788A (en) 2015-11-20 2023-04-01 Forma Therapeutics Inc Furinones as ubiquitin-specific protease 1 inhibitors
EP3402799B1 (en) 2016-01-15 2022-05-04 Enanta Pharmaceuticals, Inc. Heterocyclic compounds as rsv inhibitors
MX2020012592A (es) * 2016-02-03 2022-10-27 Janssen Sciences Ireland Uc Productos combinados para el tratamiento del vsr.
BR112018068638A2 (pt) 2016-03-15 2019-02-05 Bayer Cropscience Ag sulfonamidas substituídas para controle de pragas animais
TW201822637A (zh) 2016-11-07 2018-07-01 德商拜耳廠股份有限公司 用於控制動物害蟲的經取代磺醯胺類
EP3582784B1 (en) 2017-02-16 2022-06-08 Enanta Pharmaceuticals, Inc. Processes for the preparation of benzodiazepine derivatives
WO2019006295A1 (en) 2017-06-30 2019-01-03 Enanta Pharmaceuticals, Inc. HETEROCYCLIC COMPOUNDS AS RSV INHIBITORS
CA3077309A1 (en) 2017-09-29 2019-04-04 Enanta Pharmaceuticals, Inc. Combination pharmaceutical agents as rsv inhibitors
KR102634720B1 (ko) 2017-11-13 2024-02-06 이난타 파마슈티칼스, 인코포레이티드 벤조디아제핀-2-온 및 벤조아제핀-2-온 유도체의 분할 방법
TW201936193A (zh) 2017-12-05 2019-09-16 愛爾蘭商健生科學愛爾蘭無限公司 使用組合產品治療rsv
WO2020190935A1 (en) 2019-03-18 2020-09-24 Enanta Pharmaceuticals, Inc. Benzodiazepine derivatives as rsv inhibitors
US11505558B1 (en) 2019-10-04 2022-11-22 Enanta Pharmaceuticals, Inc. Antiviral heterocyclic compounds
AU2020357452A1 (en) 2019-10-04 2022-05-12 Enanta Pharmaceuticals, Inc Antiviral heterocyclic compounds
JP2023500213A (ja) * 2019-10-30 2023-01-05 ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー 3-ニトロ-n-(2,2,2-トリフルオロエチル)-4-ピリジンアミンの合成
PH12022551042A1 (en) 2019-10-30 2023-05-29 Janssen Sciences Ireland Unlimited Co Synthesis of 3-({5-chloro-1-[3-(methylsulfonyl)propyl]-1h-indol-2 yl} methyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2h-imidazo[4,5-c]pyridin-2-one
KR20220098170A (ko) 2019-11-07 2022-07-11 바이엘 악티엔게젤샤프트 동물 해충 방제를 위한 치환된 술포닐 아미드
UY39032A (es) 2020-01-24 2021-07-30 Enanta Pharm Inc Compuestos heterocíclicos como agentes antivirales
EP4165034A1 (en) 2020-06-11 2023-04-19 Janssen Sciences Ireland Unlimited Company Hemi (l)-tartrate forms of 3-({5-chloro-1-[3-(methylsulfonyl)propyl]-1h-indol-2 yl} methyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2h-imidazo[4,5-c]pyridin-2-one and pharmaceutical compositions comprising the same
US11534439B2 (en) 2020-07-07 2022-12-27 Enanta Pharmaceuticals, Inc. Dihydroquinoxaline and dihydropyridopyrazine derivatives as RSV inhibitors
WO2022086840A1 (en) 2020-10-19 2022-04-28 Enanta Pharmaceuticals, Inc. Heterocyclic compounds as anti-viral agents
US11945830B2 (en) 2021-02-26 2024-04-02 Enanta Pharmaceuticals, Inc. Antiviral heterocyclic compounds
WO2022184606A1 (en) 2021-03-01 2022-09-09 Janssen Sciences Ireland Unlimited Company Synthesis of rilematovir
CN114014856B (zh) * 2021-11-26 2023-12-22 嘉兴安谛康生物科技有限公司 作为呼吸道合胞病毒抗病毒剂的咪唑并吡啶类衍生物
AR129003A1 (es) 2022-04-07 2024-07-03 Enanta Pharm Inc Compuestos heterocíclicos antivirales
WO2023211997A1 (en) 2022-04-27 2023-11-02 Enanta Pharmaceuticals, Inc. Antiviral compounds
WO2024174953A1 (zh) * 2023-02-21 2024-08-29 苏州隆博泰药业有限公司 苯并咪唑类衍生物及其医药用途

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002514162A (ja) 1996-07-08 2002-05-14 デュポン ファーマシューティカルズ カンパニー Xa因子阻害薬およびトロンビン阻害薬としてのアミジノインドール類、アミジノアゾール類、およびそれらの類似体
AU1099000A (en) 1998-10-05 2000-04-26 Axys Pharmaceuticals, Inc. Novel compounds and compositions for treating hepatitis c infections
BR9916363A (pt) 1998-12-18 2001-12-11 Axys Pharm Inc Composto, composição farmacêutica e método paratratar ou prevenir um distúrbio tromboembólico
US6924287B1 (en) 1999-06-28 2005-08-02 Janssen Pharmacatica, N.V. Respiratory syncytial virus replication inhibitors
KR100731271B1 (ko) 1999-06-28 2007-06-21 얀센 파마슈티카 엔.브이. 호흡기 신시티움 바이러스 복제 억제제
US6534535B1 (en) * 1999-08-12 2003-03-18 Millennium Pharmaceuticals, Inc. Inhibitors of factor Xa
EP1255750A1 (en) * 2000-02-01 2002-11-13 Millenium Pharmaceuticals, Inc. INDOLE AND BENZIMIDAZOLE INHIBITORS OF FACTOR Xa
US20020019395A1 (en) * 2000-02-01 2002-02-14 Bing-Yan Zhu Indalone and benzimidazolone inhibitors of factor Xa
US6489338B2 (en) * 2000-06-13 2002-12-03 Bristol-Myers Squibb Company Imidazopyridine and imidazopyrimidine antiviral agents
US6506738B1 (en) * 2000-09-27 2003-01-14 Bristol-Myers Squibb Company Benzimidazolone antiviral agents
US6919331B2 (en) 2001-12-10 2005-07-19 Bristol-Myers Squibb Company Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents
HUP0402535A2 (hu) 2001-12-10 2005-04-28 Bristol-Myers Squibb Co. RSV fúzió inhibitor hatású imidazo-piridin-vegyület dihidroklorid-monohidrát sója és az ezt tartalmazó gyógyszerkészítmények
AU2002358219A1 (en) 2001-12-21 2003-07-15 Sense Proteomic Limited Protein analysis using mass spectrometry
WO2004043913A2 (en) 2002-11-08 2004-05-27 Trimeris, Inc. Hetero-substituted benzimidazole compounds and antiviral uses thereof
AR043692A1 (es) 2003-02-06 2005-08-10 Novartis Ag 2-cianopirrolopirimidinas y sus usos farmaceuticos
US7343930B2 (en) 2004-12-03 2008-03-18 Masco Corporation Of Indiana Sprayer with non-faucet control
MY140748A (en) 2004-12-06 2010-01-15 Astrazeneca Ab Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy
EP2152674B1 (en) 2007-05-22 2011-08-03 Boehringer Ingelheim International GmbH Benzimidazolone chymase inhibitors
FR2926556B1 (fr) 2008-01-22 2010-02-19 Sanofi Aventis Derives de carboxamides n-azabicycliques, leur preparation et leur application en therapeutique
TWI541241B (zh) * 2010-12-16 2016-07-11 健生科學愛爾蘭無限公司 作為呼吸道融合病毒抗病毒劑之咪唑并吡啶類
TWI515187B (zh) 2010-12-16 2016-01-01 健生科學愛爾蘭無限公司 作為呼吸道融合病毒抗病毒劑之吲哚類
TWI530495B (zh) * 2010-12-16 2016-04-21 健生科學愛爾蘭無限公司 苯并咪唑呼吸道融合病毒抑制劑
TWI501967B (zh) * 2010-12-16 2015-10-01 Janssen R&D Ireland 作為呼吸道融合病毒抗病毒劑之氮雜吲哚類
TWI527814B (zh) 2010-12-16 2016-04-01 健生科學愛爾蘭無限公司 作為呼吸道融合病毒抗病毒劑之氮雜苯并咪唑類
DK3603704T3 (da) 2010-12-17 2023-07-24 Sanofi Aventis Deutschland Indgivelse af medikament
DK2864323T3 (en) 2012-06-15 2017-08-14 Janssen Sciences Ireland Uc 1,3-DIHYDRO-2H-BENZIMIDAZOLE-2 UNDERIVATIVES SUBSTITUTED BY HETEROCYCLES AS ANTIVIRUS AGENTS AGAINST RESPIRATORY SYNCYTIAL VIRUS
JP2015519385A (ja) 2012-06-15 2015-07-09 ヤンセン・アールアンドデイ・アイルランド Rsウイルス抗ウイルス薬としての、ベンゾイミダゾールによって置換された新規4−置換1,3−ジヒドロ−2h−ベンゾイミダゾル−2−オン誘導体
EA201590020A1 (ru) 2012-06-15 2015-03-31 ЯНССЕН Ар ЭНД Ди АЙРЛЭНД Новые производные 1,3-дигидро-2h-бензимидазол-2-она, замещенные бензимидазолами, в качестве противовирусных средств против респираторного синцитиального вируса
WO2013186335A1 (en) 2012-06-15 2013-12-19 Janssen R&D Ireland 1,3 -dihydro-2h-benzimidazol-2-one derivatives substituted with heterocycles as respiratory syncytial virus antiviral agents
DK2909195T3 (en) 2012-10-16 2017-09-25 Janssen Sciences Ireland Uc ANTIVIRAL RELATIONS TO RSV

Also Published As

Publication number Publication date
EA022339B1 (ru) 2015-12-30
US20130267555A1 (en) 2013-10-10
AU2011343256B2 (en) 2015-02-05
RS54746B1 (sr) 2016-10-31
HUE028009T2 (en) 2016-11-28
CL2013001715A1 (es) 2013-12-20
JP2014503525A (ja) 2014-02-13
AU2011343256A1 (en) 2013-05-02
BR112013011949B1 (pt) 2021-11-23
TW201307325A (zh) 2013-02-16
ME02406B (me) 2016-09-20
CN103347875B (zh) 2016-03-30
DK2651922T3 (en) 2016-05-30
WO2012080447A1 (en) 2012-06-21
EP2651922A1 (en) 2013-10-23
US9321768B2 (en) 2016-04-26
BR112013011949A2 (pt) 2016-08-23
HK1185613A1 (zh) 2014-02-21
EP2651922B1 (en) 2016-02-24
MX339944B (es) 2016-06-17
SI2651922T1 (sl) 2016-08-31
NZ609487A (en) 2014-10-31
KR20140037800A (ko) 2014-03-27
SMT201600142B (it) 2016-07-01
IL225641A0 (en) 2013-06-27
US20160237083A1 (en) 2016-08-18
ZA201304423B (en) 2014-12-23
SG189866A1 (en) 2013-07-31
MY163981A (en) 2017-11-15
CN103347875A (zh) 2013-10-09
AR084335A1 (es) 2013-05-08
MX2013006887A (es) 2013-07-05
PH12013500797A1 (en) 2013-06-24
CY1117763T1 (el) 2017-05-17
PL2651922T3 (pl) 2016-10-31
CA2822000C (en) 2019-01-15
AU2011343256C1 (en) 2015-08-13
JP5945278B2 (ja) 2016-07-05
HRP20160533T1 (hr) 2016-07-01
KR101914606B1 (ko) 2018-11-02
US8921560B2 (en) 2014-12-30
ES2572258T3 (es) 2016-05-31
UA109792C2 (uk) 2015-10-12
US9944638B2 (en) 2018-04-17
CA2822000A1 (en) 2012-06-21
JP2016145236A (ja) 2016-08-12
US20150073013A1 (en) 2015-03-12
EA201390883A1 (ru) 2013-10-30
IL225641A (en) 2016-09-29

Similar Documents

Publication Publication Date Title
TWI515187B (zh) 作為呼吸道融合病毒抗病毒劑之吲哚類
TWI527814B (zh) 作為呼吸道融合病毒抗病毒劑之氮雜苯并咪唑類
CN103339128B (zh) 作为呼吸道合胞病毒抗病毒剂的氮杂吲哚
TWI530495B (zh) 苯并咪唑呼吸道融合病毒抑制劑
JP6259451B2 (ja) Rsウイルス抗ウイルス薬としての、複素環によって置換された新規1,3−ジヒドロ−2h−ベンゾイミダゾル−2−オン誘導体
AU2013276520A1 (en) 1,3-dihydro-2H-benzimidazol-2-one derivatives substituted with benzimidazoles as respiratory syncytial virus antiviral agents
HK1185613B (en) Indoles as respiratory syncytial virus antiviral agents
HK1185065A (en) Benzimidazole respiratory syncytial virus inhibitors

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees