CN105330675A - Hiv复制的抑制剂 - Google Patents
Hiv复制的抑制剂 Download PDFInfo
- Publication number
- CN105330675A CN105330675A CN201510602538.4A CN201510602538A CN105330675A CN 105330675 A CN105330675 A CN 105330675A CN 201510602538 A CN201510602538 A CN 201510602538A CN 105330675 A CN105330675 A CN 105330675A
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- CN
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- Prior art keywords
- methyl
- compound
- pyridin
- tetrahydrochysene
- solution
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- 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
- A61K31/435—Heterocyclic 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
- A61K31/4353—Heterocyclic 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
- A61K31/4365—Heterocyclic 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 having sulfur as a ring hetero atom, e.g. ticlopidine
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic 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
- A61K31/4353—Heterocyclic 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
- A61K31/437—Heterocyclic 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
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- 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
- A61K31/435—Heterocyclic 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A—HUMAN NECESSITIES
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—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
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
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- Virology (AREA)
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- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| BR112012033689A2 (pt) | 2010-07-02 | 2019-09-24 | Gilead Sciences Inc | derivados de ácido 2-quinolinil-acético como compostos de hiv antivirais |
| AU2011274322B2 (en) | 2010-07-02 | 2015-08-13 | Gilead Sciences, Inc. | Naphth- 2 -ylacetic acid derivatives to treat AIDS |
| NZ610315A (en) | 2010-11-15 | 2015-08-28 | Univ Leuven Kath | Antiviral condensed heterocyclic compounds |
| AU2011330850B2 (en) * | 2010-11-15 | 2016-01-28 | Viiv Healthcare Uk Limited | Inhibitors of HIV replication |
| EA024952B1 (ru) | 2011-04-21 | 2016-11-30 | Джилид Сайэнс, Инк. | Бензотиазолы и их применение для лечения вич-инфекции |
| WO2013062028A1 (ja) | 2011-10-25 | 2013-05-02 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害剤 |
| WO2013103724A1 (en) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | 2- (tert - butoxy) -2- (7 -methylquinolin- 6 - yl) acetic acid derivatives for treating aids |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| ES2668422T3 (es) | 2012-04-20 | 2018-05-18 | Gilead Sciences, Inc. | Derivados del ácido benzotiazol-6-il acético y su uso para tratar una infección por VIH |
| US8906929B2 (en) | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| TW201441197A (zh) | 2013-01-31 | 2014-11-01 | Shionogi & Co | Ｈｉｖ複製抑制劑 |
| EP2970273B1 (en) | 2013-03-13 | 2017-03-01 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| EP2970301B1 (en) | 2013-03-13 | 2017-01-11 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| EP2970298A1 (en) | 2013-03-13 | 2016-01-20 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2970274B1 (en) | 2013-03-14 | 2017-03-01 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| US9540393B2 (en) | 2013-03-14 | 2017-01-10 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| CA2916504A1 (en) | 2013-06-25 | 2014-12-31 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| UY35625A (es) | 2013-06-25 | 2014-12-31 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos como inhibidores de quinasa |
| EP2821082A1 (en) | 2013-07-05 | 2015-01-07 | Laboratoire Biodim | Method of producing an inactivated lentivirus, especially HIV, vaccine, kit and method of use |
| US9944656B2 (en) | 2014-02-12 | 2018-04-17 | VIIV Healthcare UK (No.5) Limited | Benzothiazole macrocycles as inhibitors of human immunodeficiency virus replication |
| US9834566B2 (en) | 2014-02-18 | 2017-12-05 | VIIV Healthcare UK (No.5) Limited | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| WO2015126758A1 (en) | 2014-02-18 | 2015-08-27 | Bristol-Myers Squibb Company | Imidazopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9409922B2 (en) | 2014-02-18 | 2016-08-09 | Bristol-Myers Squibb Company | Imidazopyridine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9273067B2 (en) | 2014-02-19 | 2016-03-01 | Bristol-Myers Squibb Company | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| EP3107913B1 (en) | 2014-02-19 | 2018-07-04 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| JP6579549B2 (ja) | 2014-05-16 | 2019-09-25 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する３環性複素環誘導体 |
| EA031614B1 (ru) | 2014-10-24 | 2019-01-31 | Бристол-Майерс Сквибб Компани | Трициклические атропоизомерные соединения |
| HUE050592T2 (hu) | 2014-10-24 | 2020-12-28 | Bristol Myers Squibb Co | Indol karboxamid vegyületek, amelyek hasznosak kináz inhibitorokként |
| MA40302B1 (fr) | 2014-10-24 | 2018-10-31 | Bristol Myers Squibb Co | Dérivés de carbazole |
| US10806734B2 (en) | 2015-05-08 | 2020-10-20 | Katholieke Universiteit Leuven | Functional cure of retroviral infection |
| WO2016194806A1 (ja) | 2015-05-29 | 2016-12-08 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する含窒素３環性誘導体 |
| CN111018912A (zh) * | 2019-11-22 | 2020-04-17 | 苏州二叶制药有限公司 | 一种抗病毒药物关键中间体的合成和纯化方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1310488A1 (en) * | 2000-08-09 | 2003-05-14 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| WO2005076861A2 (en) * | 2004-02-04 | 2005-08-25 | University Of Virginia Patent Foundation | Compounds that inhibit hiv particle formation |
| WO2010130842A1 (en) * | 2009-05-15 | 2010-11-18 | Katholieke Universiteit Leuven | Thieno [2, 3-b] pyridine derivatives as viral replication inhibitors |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| US5489586A (en) * | 1994-03-07 | 1996-02-06 | Warner-Lambert Company | Method for treating inflammatory disease in humans |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035296A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Improved release of medicament active agents from a chewing gum coating |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| JP2003171381A (ja) | 2001-09-25 | 2003-06-20 | Takeda Chem Ind Ltd | エントリー阻害剤 |
| JP2003119137A (ja) | 2001-10-10 | 2003-04-23 | Japan Tobacco Inc | Ｈｉｖ阻害剤 |
| ATE355064T1 (de) | 2001-10-26 | 2006-03-15 | Angeletti P Ist Richerche Bio | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| WO2003047564A1 (en) | 2001-12-05 | 2003-06-12 | Shionogi & Co., Ltd. | Derivative having hiv integrase inhibitory activity |
| CA2469592C (en) | 2001-12-12 | 2005-08-23 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| ATE516029T1 (de) | 2001-12-21 | 2011-07-15 | Tibotec Pharm Ltd | Sulfonamide die ein heterozyklus-substituiertes phenyl enthalten als broadspectrum-hiv-protease- inhibitoren |
| AU2003216049B2 (en) | 2002-01-17 | 2008-07-17 | Merck Sharp & Dohme Corp. | Hydroxynaphthyridinone carboxamides useful as HIV integrase inhibitors |
| TW200306192A (en) | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
| ATE430751T1 (de) * | 2004-12-17 | 2009-05-15 | Hoffmann La Roche | Thienopyridinderivate als allostere gaba-b- enhancer |
| CA2705312C (en) * | 2007-11-15 | 2013-06-25 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| RU2402531C2 (ru) * | 2008-09-24 | 2010-10-27 | Александр Леонидович Гинцбург | Биологически активные вещества, подавляющие патогенные бактерии |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| US20120316161A1 (en) | 2009-12-23 | 2012-12-13 | Katholieke Universiteit Leuven | Novel antiviral compounds |
| AU2011330850B2 (en) * | 2010-11-15 | 2016-01-28 | Viiv Healthcare Uk Limited | Inhibitors of HIV replication |
| NZ610315A (en) | 2010-11-15 | 2015-08-28 | Univ Leuven Kath | Antiviral condensed heterocyclic compounds |
| AU2012209373A1 (en) | 2011-01-24 | 2013-04-11 | Glaxosmithkline Llc | Isoquinoline compounds and methods for treating HIV |
| JP6055468B2 (ja) | 2011-07-15 | 2016-12-27 | ヴィーブ ヘルスケア ユーケー リミテッド | アザインドール化合物及びｈｉｖを治療するための方法 |
-
2011
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- 2011-11-01 JP JP2013538301A patent/JP5902704B2/ja not_active Expired - Fee Related
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- 2011-11-01 WO PCT/IB2011/054852 patent/WO2012066442A1/en not_active Ceased
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- 2011-11-01 CN CN201510602538.4A patent/CN105330675A/zh active Pending
- 2011-11-01 CN CN201180065030.5A patent/CN103429595B/zh not_active Expired - Fee Related
- 2011-11-01 RU RU2013121788/04A patent/RU2564445C2/ru not_active IP Right Cessation
- 2011-11-01 BR BR112013011991A patent/BR112013011991A2/pt not_active IP Right Cessation
- 2011-11-10 TW TW100141049A patent/TWI445709B/zh not_active IP Right Cessation
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2013
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2014
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2016
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- 2016-08-19 US US15/241,520 patent/US20160355528A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1310488A1 (en) * | 2000-08-09 | 2003-05-14 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| WO2005076861A2 (en) * | 2004-02-04 | 2005-08-25 | University Of Virginia Patent Foundation | Compounds that inhibit hiv particle formation |
| WO2010130842A1 (en) * | 2009-05-15 | 2010-11-18 | Katholieke Universiteit Leuven | Thieno [2, 3-b] pyridine derivatives as viral replication inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| SERGEY V. RYABUKHIN，等: "Heterocyclic ortho-aminocarbonyl compounds in the Friedlander reaction promoted by chlorotrimethylsilane", 《HETEROCYCLES》 * |
Also Published As
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|---|---|
| MX2013005486A (es) | 2013-12-12 |
| TWI445709B (zh) | 2014-07-21 |
| BR112013011991A2 (pt) | 2016-08-30 |
| RU2564445C2 (ru) | 2015-10-10 |
| TW201300395A (zh) | 2013-01-01 |
| AU2011330850B2 (en) | 2016-01-28 |
| US9447116B2 (en) | 2016-09-20 |
| UY33729A (es) | 2012-06-29 |
| US20120136023A1 (en) | 2012-05-31 |
| CA2817896A1 (en) | 2012-05-24 |
| WO2012066442A1 (en) | 2012-05-24 |
| CN103429595A (zh) | 2013-12-04 |
| ZA201303433B (en) | 2014-12-23 |
| AU2016202565A1 (en) | 2016-05-19 |
| US20140315927A1 (en) | 2014-10-23 |
| EP2640729A1 (en) | 2013-09-25 |
| JP5902704B2 (ja) | 2016-04-13 |
| US8809363B2 (en) | 2014-08-19 |
| EP2640729B1 (en) | 2016-12-21 |
| MX343274B (es) | 2016-10-31 |
| AU2011330850A1 (en) | 2013-06-27 |
| RU2013121788A (ru) | 2014-12-27 |
| CN103429595B (zh) | 2015-10-21 |
| CL2013001338A1 (es) | 2014-03-28 |
| AR083870A1 (es) | 2013-03-27 |
| JP2013542247A (ja) | 2013-11-21 |
| JP2016164163A (ja) | 2016-09-08 |
| US20160355528A1 (en) | 2016-12-08 |
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