JP2010505866A - ヒトにおけるケトコナゾールエナンチオマー - Google Patents
ヒトにおけるケトコナゾールエナンチオマー Download PDFInfo
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- JP2010505866A JP2010505866A JP2009531558A JP2009531558A JP2010505866A JP 2010505866 A JP2010505866 A JP 2010505866A JP 2009531558 A JP2009531558 A JP 2009531558A JP 2009531558 A JP2009531558 A JP 2009531558A JP 2010505866 A JP2010505866 A JP 2010505866A
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- ketoconazole
- enantiomer
- ketoconazole enantiomer
- hmg
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- XMAYWYJOQHXEEK-ZEQKJWHPSA-N (2S,4R)-ketoconazole Chemical class C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@H]1O[C@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-ZEQKJWHPSA-N 0.000 claims abstract description 186
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| JP2022522873A (ja) * | 2019-03-04 | 2022-04-20 | ストロングブリッジ ダブリン リミテッド | レボケトコナゾールによる疾患の処置方法 |
Families Citing this family (5)
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| ATE528005T1 (de) * | 2005-01-10 | 2011-10-15 | Cortendo Ab Publ | 2s,4r ketoconazol zur behandlung von diabetes, metabolischem syndrom und anderen erkrankungen |
| AU2007204969A1 (en) * | 2006-01-10 | 2007-07-19 | Cortendo Invest Ab | Methods and compositions for treating prostate cancer |
| JP2010505866A (ja) | 2006-10-02 | 2010-02-25 | コルテンド・インヴェスト・アクチボラゲット | ヒトにおけるケトコナゾールエナンチオマー |
| US20160244436A1 (en) * | 2013-09-25 | 2016-08-25 | Cortendo Ab (Publ) | Novel functionalized 5-(phenoxymethyl)-1,3-dioxane analogs exhibiting cytochrome p450 inhibition and their method of use |
| WO2016048984A1 (en) * | 2014-09-25 | 2016-03-31 | Cortendo Ab (Publ) | Methods and compositions for the treatment of cushing's syndrome using 2s, 4r ketoconazole |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6040307A (en) * | 1992-12-22 | 2000-03-21 | Sepracor Inc. | Methods ad compositions of (-) ketoconazole for treating fungal yeast and dermatophyte infections |
| US20040180868A1 (en) * | 2003-03-12 | 2004-09-16 | Mullally John P. | Composition and method for treating inflammations by reducing C-reactive protein |
| WO2006072881A1 (en) * | 2005-01-10 | 2006-07-13 | Cortendo Invest Ab | Methods and compositions for treating diabetes, metabolic syndrome and other conditions |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144346A (en) | 1977-01-31 | 1979-03-13 | Janssen Pharmaceutica N.V. | Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles |
| US4503055A (en) | 1979-03-26 | 1985-03-05 | Janssen Pharmaceutica, N.V. | Derivatives of [4-(piperazin-1-yl-phenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles |
| US4814333A (en) | 1987-07-28 | 1989-03-21 | The Trustees Of Dartmouth College | Method for treatment of hypercortisolemic, depressed patients |
| US5432176A (en) | 1988-11-29 | 1995-07-11 | The John Hopkins University | Method of retarding the progression of chronic renal failure |
| WO1994014446A1 (en) | 1992-12-22 | 1994-07-07 | Sepracor, Inc. | Methods and compositions of (+) ketoconazole for treating fungal, yeast and dermatophyte infections |
| IL109728A0 (en) | 1993-05-28 | 1994-08-26 | Pfizer Res & Dev | Indoles |
| US5869255A (en) * | 1994-02-01 | 1999-02-09 | The Regents Of The University Of California | Probes labeled with energy transfer couples dyes exemplified with DNA fragment analysis |
| DK0779810T3 (da) | 1994-08-09 | 2003-10-20 | Cortendo Ab | Anvendelse af ketoconazol og beslægtede stoffer i medikamenter til behandling af type II-diabetes |
| US6642236B1 (en) * | 1998-12-14 | 2003-11-04 | Cortendo Ab | Methods for prophylactic treatment of cardiovascular disease with inhibitor of cortisol synthesis |
| US5584790A (en) * | 1995-09-08 | 1996-12-17 | Beckman Instruments, Inc. | Variable inclination centrifugation assembly for rapid separation of blood |
| CA2240115A1 (en) | 1995-12-14 | 1997-06-19 | Wallace T. Ashton | Antagonists of gonadotropin releasing hormone |
| AU1856997A (en) | 1996-02-02 | 1997-08-22 | Merck & Co., Inc. | Method for raising hdl cholesterol levels |
| AR008789A1 (es) | 1996-07-31 | 2000-02-23 | Bayer Corp | Piridinas y bifenilos substituidos |
| US5994334A (en) * | 1997-02-05 | 1999-11-30 | University Of Maryland | Androgen synthesis inhibitors |
| SE9700642D0 (sv) | 1997-02-24 | 1997-02-24 | Kronvall Stefan Med Ab | Medel och sätt för förebyggande och behandling av det metabola syndromet |
| WO1999001423A1 (en) | 1997-07-01 | 1999-01-14 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| WO2000042026A1 (en) | 1999-01-15 | 2000-07-20 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| PT1171465E (pt) | 1999-03-29 | 2004-12-31 | Uutech Ltd | Analogos de petido inibidor gastrico e sua utilizacao para o tratamento de diabetes |
| CA2369549A1 (en) | 1999-04-02 | 2000-10-12 | Robert W. Desimone | Aryl and heteroaryl fused aminoalkyl-imidazole derivatives and their use as antidiabetics |
| KR20020014797A (ko) | 1999-05-17 | 2002-02-25 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 글루카곤 길항제/역 아고니스트 |
| GB9915625D0 (en) | 1999-07-02 | 1999-09-01 | Cortendo Ab | Method |
| PE20010612A1 (es) | 1999-09-28 | 2001-07-12 | Bayer Corp | Agonistas del receptor 3 (r3) del peptido activador de la adenilato ciclasa de la pituitaria y su uso farmacologico |
| US20020055512A1 (en) * | 2000-01-21 | 2002-05-09 | Cortendo Ab. | Compositions for delivery of a cortisol antagonist |
| GB0001449D0 (en) | 2000-01-21 | 2000-03-08 | Cortendo Ab | Compositions |
| AU2001268661A1 (en) | 2000-06-27 | 2002-01-08 | Aventis Pharma S.A. | 20-fluoro-17(20)-vinyl steroids as inhibitors of c17-20-lyase and 5-alpha reductase |
| GB0118300D0 (en) | 2001-07-26 | 2001-09-19 | Cortendo Ab | Formulations |
| WO2003027225A2 (en) | 2001-09-21 | 2003-04-03 | Bayer Healthcare Ag | Regulation of human steroid 5-alpha reductase |
| JP2005512516A (ja) | 2001-09-24 | 2005-05-12 | メルク エンド カムパニー インコーポレーテッド | スタチン薬物の組合せのスクリーニング方法および選択方法 |
| WO2003027095A1 (en) | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Substituted 3-pyridyl tetrazoles as steroid c17,20 lyase inhibitors |
| MXPA04007713A (es) * | 2002-02-07 | 2004-11-10 | Pfizer | Uso de inhibidores de la fosfodiesterasa tipo 5, tal como sildenafil, en el tratamiento del sindrome de ovario poliquistico. |
| AU2003256988A1 (en) | 2002-12-11 | 2004-06-30 | Amylin Pharmaceuticals, Inc. | Methods and compositions for treating polycystic ovary syndrome |
| US20080262005A1 (en) | 2004-05-14 | 2008-10-23 | Neurocrine Biosciences, Inc. | Uracil-Type Gonadotropin-Releasing Hormone Receptor Antagonists and Methods Related Thereto |
| US20060002999A1 (en) * | 2004-06-17 | 2006-01-05 | Forest Laboratories, Inc. | Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane |
| US20070116839A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition With C-Reactive Protein Reducing Substance and Compositions Sweetened Therewith |
| AU2007204969A1 (en) * | 2006-01-10 | 2007-07-19 | Cortendo Invest Ab | Methods and compositions for treating prostate cancer |
| JP2010505866A (ja) | 2006-10-02 | 2010-02-25 | コルテンド・インヴェスト・アクチボラゲット | ヒトにおけるケトコナゾールエナンチオマー |
| WO2012052540A1 (en) | 2010-10-21 | 2012-04-26 | Universitaet Des Saarlandes | Selective cyp11b1 inhibitors for the treatment of cortisol dependent diseases |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6040307A (en) * | 1992-12-22 | 2000-03-21 | Sepracor Inc. | Methods ad compositions of (-) ketoconazole for treating fungal yeast and dermatophyte infections |
| US20040180868A1 (en) * | 2003-03-12 | 2004-09-16 | Mullally John P. | Composition and method for treating inflammations by reducing C-reactive protein |
| WO2006072881A1 (en) * | 2005-01-10 | 2006-07-13 | Cortendo Invest Ab | Methods and compositions for treating diabetes, metabolic syndrome and other conditions |
Non-Patent Citations (1)
| Title |
|---|
| JPN6012021638; ROTSTEIN,D.M. et al: 'Stereoisomers of ketoconazole: preparation and biological activity' Journal of Medicinal Chemistry Vol.35, No.15, 1992, p.2818-2825 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022522873A (ja) * | 2019-03-04 | 2022-04-20 | ストロングブリッジ ダブリン リミテッド | レボケトコナゾールによる疾患の処置方法 |
| JP7574204B2 (ja) | 2019-03-04 | 2024-10-28 | ストロングブリッジ ダブリン リミテッド | レボケトコナゾールによる疾患の処置方法 |
| US12377096B2 (en) | 2019-03-04 | 2025-08-05 | Xeris Pharmaceuticals, Inc. | Methods of treating disease with levoketoconazole |
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| US9198906B2 (en) | 2015-12-01 |
| WO2008042898A9 (en) | 2008-09-04 |
| BRPI0719835A2 (pt) | 2014-05-06 |
| AU2007303219A1 (en) | 2008-04-10 |
| US20190209555A1 (en) | 2019-07-11 |
| WO2008042898A3 (en) | 2008-10-23 |
| US20100093755A1 (en) | 2010-04-15 |
| WO2008042898A2 (en) | 2008-04-10 |
| US20180125841A1 (en) | 2018-05-10 |
| US20160067243A1 (en) | 2016-03-10 |
| NO20091593L (no) | 2009-04-22 |
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