JP2004513076A5 - - Google Patents
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- JP2004513076A5 JP2004513076A5 JP2002514095A JP2002514095A JP2004513076A5 JP 2004513076 A5 JP2004513076 A5 JP 2004513076A5 JP 2002514095 A JP2002514095 A JP 2002514095A JP 2002514095 A JP2002514095 A JP 2002514095A JP 2004513076 A5 JP2004513076 A5 JP 2004513076A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- indol
- phenoxy
- pharmaceutical composition
- trifluoromethoxy
- 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.)
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- 239000008194 pharmaceutical composition Substances 0.000 description 23
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- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 8
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- 239000000556 agonist Substances 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
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| MX2024002146A (es) | 2021-08-19 | 2024-03-08 | Merck Sharp & Dohme Llc | Compuestos para el tratamiento de afecciones relacionadas con la actividad de pcsk9. |
| EP4540267B1 (en) | 2022-06-15 | 2026-04-15 | Merck Sharp & Dohme LLC | Cyclic peptides for trapping interleukin-1 beta |
| IL321166A (en) | 2022-12-02 | 2025-07-01 | Merck Sharp & Dohme Llc | Preparation of fused azole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| US20250152658A1 (en) | 2023-11-14 | 2025-05-15 | Merck Sharp & Dohme Llc | Cyclic peptide for trapping interleukin-1 beta |
| WO2025128805A1 (en) | 2023-12-15 | 2025-06-19 | Merck Sharp & Dohme Llc | A cyclic peptide il-1beta trap for the treatment of atherosclerosis and inflammatory disorders |
| US20260022125A1 (en) | 2024-07-19 | 2026-01-22 | Merck Sharp & Dohme Llc | Pyrrolopyridazine vegfr inhibitors |
| WO2026096330A1 (en) | 2024-10-28 | 2026-05-07 | Merck Sharp & Dohme Llc | Glp-1 receptor agonists and methods of use |
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| US3564009A (en) | 1966-01-13 | 1971-02-16 | Sumitomo Chemical Co | Process for producing 1-acylindole derivatives |
| CH605742A5 (en) | 1973-11-29 | 1978-10-13 | Crc Ricerca Chim | 1-Benzoyl-2-methyl-indole derivs. |
| AU4649189A (en) | 1988-11-14 | 1990-06-12 | Upjohn Company, The | Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents |
| JPH0764841B2 (ja) | 1990-10-03 | 1995-07-12 | ファイザー製薬株式会社 | インドール誘導体およびその用途 |
| WO1993005020A1 (en) | 1991-09-06 | 1993-03-18 | Merck & Co., Inc. | Indoles as inhibitors of hiv reverse transcriptase |
| US5527819A (en) | 1991-09-06 | 1996-06-18 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| PT633886E (pt) | 1992-04-03 | 2001-03-30 | Upjohn Co | Aminas biciclicas-heterociclicas farmaceuticamente activas |
| ZA939516B (en) * | 1992-12-22 | 1994-06-06 | Smithkline Beecham Corp | Endothelin receptor antagonists |
| US5686481A (en) * | 1993-12-21 | 1997-11-11 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
| CA2194984C (en) | 1994-07-26 | 2002-07-02 | John Eugene Macor | 4-indole derivatives as serotonin agonists and antagonists |
| RU2152385C1 (ru) | 1994-07-27 | 2000-07-10 | Санкио Компани Лимитед | Гетероциклические соединения, применимые в качестве аллостерических эффекторов при мускариновых рецепторах |
| US5532237A (en) | 1995-02-15 | 1996-07-02 | Merck Frosst Canada, Inc. | Indole derivatives with affinity for the cannabinoid receptor |
| ATE246686T1 (de) * | 1995-03-09 | 2003-08-15 | Kyowa Hakko Kogyo Kk | Pyrrolocarbazolderivate |
| FR2735774B1 (fr) | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| EP0922028A1 (en) | 1996-08-26 | 1999-06-16 | Genetics Institute, Inc. | Inhibitors of phospholipase enzymes |
| CA2322163A1 (en) | 1998-02-25 | 1999-09-02 | John Mckew | Inhibitors of phospholipase a2 |
| PL343007A1 (en) * | 1998-02-25 | 2001-07-30 | Genetics Inst | Inhibitors of phospholipase enzymes |
| SK12742000A3 (sk) | 1998-02-25 | 2001-05-10 | Genetics Institute, Inc. | Inhibítory fosfolipázových enzýmov, farmaceutický prostriedok s ich obsahom a ich použitie |
| EE200100323A (et) * | 1998-12-18 | 2002-08-15 | Axys Pharmaceuticals, Inc. | (Hetero)arüüli - bitsüklilise heteroarüüli derivaadid, nende valmistamine ja nende kasutamine proteaasiinhibiitoritena |
-
2001
- 2001-07-20 JP JP2002514095A patent/JP2004513076A/ja not_active Withdrawn
- 2001-07-20 AU AU7705601A patent/AU7705601A/xx active Pending
- 2001-07-20 WO PCT/US2001/022979 patent/WO2002008188A1/en not_active Ceased
- 2001-07-20 CA CA002415742A patent/CA2415742A1/en not_active Abandoned
- 2001-07-20 DE DE60128475T patent/DE60128475T2/de not_active Expired - Fee Related
- 2001-07-20 EP EP01954836A patent/EP1305285B1/en not_active Expired - Lifetime
- 2001-07-20 AT AT01954836T patent/ATE362468T1/de not_active IP Right Cessation
- 2001-07-20 AU AU2001277056A patent/AU2001277056B2/en not_active Ceased
- 2001-07-25 US US09/912,961 patent/US6525083B2/en not_active Expired - Fee Related
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