RU2572244C2 - Ингибиторы ароматазы - Google Patents
Ингибиторы ароматазы Download PDFInfo
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- RU2572244C2 RU2572244C2 RU2012111119/04A RU2012111119A RU2572244C2 RU 2572244 C2 RU2572244 C2 RU 2572244C2 RU 2012111119/04 A RU2012111119/04 A RU 2012111119/04A RU 2012111119 A RU2012111119 A RU 2012111119A RU 2572244 C2 RU2572244 C2 RU 2572244C2
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- Russia
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- compound
- alkyl
- arh
- mmol
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- 239000003886 aromatase inhibitor Substances 0.000 title description 13
- 229940046844 aromatase inhibitors Drugs 0.000 title description 10
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 101
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 44
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- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 description 26
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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
- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic 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
- C07D403/12—Heterocyclic 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 chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Diabetes (AREA)
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- Dermatology (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0914767.9A GB0914767D0 (en) | 2009-08-24 | 2009-08-24 | Compound |
| GB0914767.9 | 2009-08-24 | ||
| PCT/GB2010/051391 WO2011023989A1 (en) | 2009-08-24 | 2010-08-23 | Aromatase inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012111119A RU2012111119A (ru) | 2013-10-10 |
| RU2572244C2 true RU2572244C2 (ru) | 2016-01-10 |
Family
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Family Applications (1)
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| RU2012111119/04A RU2572244C2 (ru) | 2009-08-24 | 2010-08-23 | Ингибиторы ароматазы |
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| US (1) | US8846737B2 (enExample) |
| EP (1) | EP2470512B1 (enExample) |
| JP (1) | JP5828839B2 (enExample) |
| CN (1) | CN102596919B (enExample) |
| GB (1) | GB0914767D0 (enExample) |
| RU (1) | RU2572244C2 (enExample) |
| WO (1) | WO2011023989A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015100609A1 (en) * | 2013-12-31 | 2015-07-09 | Beaufour Ipsen Tianjin Pharmaceutical Co., Ltd | New substituted biphenyl analogues as dual inhibitors of aromatase and sulfatase |
| DE102017116299A1 (de) | 2017-07-19 | 2019-01-24 | Huf Hülsbeck & Fürst Gmbh & Co. Kg | Verfahren zum Zuordnen einer Reifendrucküberwachungseinheit zu einer Radposition eines Fahrzeugs |
| HUE067314T2 (hu) | 2017-09-22 | 2024-10-28 | Jubilant Epipad LLC | Heterociklusos vegyületek mint PAD gátlók |
| KR102782563B1 (ko) | 2017-10-18 | 2025-03-14 | 주빌런트 에피파드 엘엘씨 | Pad 억제제로서의 이미다조-피리딘 화합물 |
| KR20200085836A (ko) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pd1/pd-l1 활성화 억제제로서의 피리미딘 유도체 |
| BR112020010322A2 (pt) | 2017-11-24 | 2020-11-17 | Jubilant Episcribe Llc | composto da fórmula i; composto da fórmula ia; composto da fórmula ib; processo de preparação de compostos da fórmula i; composição farmacêutica; método para o tratamento e/ou prevenção de várias doenças; uso dos compostos; método para o tratamento de câncer; e método para o tratamento e/ou prevenção de uma afecção mediada por prmt5 ou um distúrbio proliferativo ou câncer |
| CA3085353A1 (en) | 2017-12-21 | 2019-06-27 | Ribon Therapeutics Inc. | Quinazolinones as parp14 inhibitors |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| PL239999B1 (pl) | 2018-06-18 | 2022-02-07 | Politechnika Gdanska | A midosiarczanowe pochodne 4-(1-fenylo-1H-[1,2,3]triazol- -4-ylo)-fenolu, ich zastosowanie medyczne i diagnostyczne, oraz sposób otrzymywania amidosiarczanowych pochodnych 4-(1-fenylo- 1H-[1,2,3]triazol-4-ylo)-fenolu |
| CN113387894B (zh) * | 2021-06-22 | 2023-02-24 | 首都医科大学脑重大疾病研究中心(北京脑重大疾病研究院) | 1-n-苯乙腈基氨基-三氮唑和嘧啶衍生物及其制备方法和应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0371564A2 (en) * | 1988-11-29 | 1990-06-06 | Janssen Pharmaceutica N.V. | (1H-azol-1-ylmethyl)substituted quinoline, quinazoline or quinoxaline derivatives |
| EP0490816A2 (de) * | 1990-12-12 | 1992-06-17 | Ciba-Geigy Ag | Fluorverbindungen |
| WO1999017777A1 (en) * | 1997-10-08 | 1999-04-15 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| RU2131418C1 (ru) * | 1992-12-16 | 1999-06-10 | Арво Сакари Ламминтауста Ристо | Соединения, селективно ингибирующие ароматазу, способ получения и фармацевтическая композиция |
| EP1431292A1 (en) * | 2002-12-16 | 2004-06-23 | Laboratoire Theramex | 1-N-phenylamino-1H-imidazole derivatives as aromatase inhibitors |
| RU2006125417A (ru) * | 2003-12-15 | 2008-01-27 | Лаборатуар Терамекс (Mc) | Производные 1-n-фениламино-1н-имидазола и содержащие их фармацевтические композиции |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ207394A (en) | 1983-03-08 | 1987-03-06 | Commw Serum Lab Commission | Detecting or determining sequence of amino acids |
| GB9003939D0 (en) | 1990-02-21 | 1990-04-18 | Imperial College | Sulphatase inhibitors |
| CH683151A5 (de) | 1991-04-24 | 1994-01-31 | Ciba Geigy Ag | Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus. |
| GB9118478D0 (en) | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| GB9118465D0 (en) | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| ATE186052T1 (de) | 1991-09-02 | 1999-11-15 | Yamanouchi Pharma Co Ltd | Triazolylierte tertiäre aminverbindungen oder ihre salze |
| GB9422777D0 (en) | 1994-11-11 | 1995-01-04 | Imperial College | Assay |
| US5723315A (en) | 1996-08-23 | 1998-03-03 | Genetics Institute, Inc. | Secreted proteins and polynucleotides encoding them |
| CA2263154A1 (en) | 1996-08-07 | 1998-02-12 | Darwin Discovery Limited | Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity |
| PT963377E (pt) | 1996-08-30 | 2009-05-11 | Human Genome Sciences Inc | Interleucina 19 |
| US6126939A (en) | 1996-09-03 | 2000-10-03 | Yeda Research And Development Co. Ltd. | Anti-inflammatory dipeptide and pharmaceutical composition thereof |
| US5935977A (en) | 1996-09-25 | 1999-08-10 | Ss Pharmaceutical Co., Ltd. | Substituted vinyl pyridine derivative and drugs containing the same |
| US6585954B1 (en) | 1998-03-26 | 2003-07-01 | Kyowa Hakko Kogyo Co., Ltd. | Method for searching steroid sulfatase inhibitors |
| GB9807779D0 (en) | 1998-04-09 | 1998-06-10 | Ciba Geigy Ag | Organic compounds |
| US20020019527A1 (en) * | 2000-04-27 | 2002-02-14 | Wei-Bo Wang | Substituted phenyl farnesyltransferase inhibitors |
| AU2002339192A1 (en) * | 2001-11-21 | 2003-06-10 | Sterix Limited | 1,2,4-triazole derivatives containing a sulphamate group as aromatase inhibitors |
| EP1544195A1 (en) | 2003-12-15 | 2005-06-22 | Laboratoire Theramex | 1-N-phenyl-amino- 1H-imidazole derivatives and pharmaceutical compositions containing them |
| GB0411562D0 (en) | 2004-05-24 | 2004-06-23 | Sterix Ltd | Compound |
| MX2008015917A (es) * | 2006-06-22 | 2009-01-13 | Novartis Ag | Formulaciones de liberacion sostenida de inhibidores de aromatasa. |
-
2009
- 2009-08-24 GB GBGB0914767.9A patent/GB0914767D0/en not_active Ceased
-
2010
- 2010-08-23 US US13/392,206 patent/US8846737B2/en active Active
- 2010-08-23 JP JP2012526125A patent/JP5828839B2/ja not_active Expired - Fee Related
- 2010-08-23 EP EP10750154.6A patent/EP2470512B1/en active Active
- 2010-08-23 RU RU2012111119/04A patent/RU2572244C2/ru not_active IP Right Cessation
- 2010-08-23 WO PCT/GB2010/051391 patent/WO2011023989A1/en not_active Ceased
- 2010-08-23 CN CN201080037827.XA patent/CN102596919B/zh not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0371564A2 (en) * | 1988-11-29 | 1990-06-06 | Janssen Pharmaceutica N.V. | (1H-azol-1-ylmethyl)substituted quinoline, quinazoline or quinoxaline derivatives |
| EP0490816A2 (de) * | 1990-12-12 | 1992-06-17 | Ciba-Geigy Ag | Fluorverbindungen |
| RU2131418C1 (ru) * | 1992-12-16 | 1999-06-10 | Арво Сакари Ламминтауста Ристо | Соединения, селективно ингибирующие ароматазу, способ получения и фармацевтическая композиция |
| WO1999017777A1 (en) * | 1997-10-08 | 1999-04-15 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| EP1431292A1 (en) * | 2002-12-16 | 2004-06-23 | Laboratoire Theramex | 1-N-phenylamino-1H-imidazole derivatives as aromatase inhibitors |
| RU2006125417A (ru) * | 2003-12-15 | 2008-01-27 | Лаборатуар Терамекс (Mc) | Производные 1-n-фениламино-1н-имидазола и содержащие их фармацевтические композиции |
Also Published As
| Publication number | Publication date |
|---|---|
| US8846737B2 (en) | 2014-09-30 |
| EP2470512A1 (en) | 2012-07-04 |
| WO2011023989A1 (en) | 2011-03-03 |
| US20120238550A1 (en) | 2012-09-20 |
| EP2470512B1 (en) | 2018-05-02 |
| GB0914767D0 (en) | 2009-09-30 |
| CN102596919B (zh) | 2015-11-25 |
| CN102596919A (zh) | 2012-07-18 |
| RU2012111119A (ru) | 2013-10-10 |
| JP5828839B2 (ja) | 2015-12-09 |
| JP2013502451A (ja) | 2013-01-24 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20160824 |