JP2010505866A5 - - Google Patents
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- Publication number
- JP2010505866A5 JP2010505866A5 JP2009531558A JP2009531558A JP2010505866A5 JP 2010505866 A5 JP2010505866 A5 JP 2010505866A5 JP 2009531558 A JP2009531558 A JP 2009531558A JP 2009531558 A JP2009531558 A JP 2009531558A JP 2010505866 A5 JP2010505866 A5 JP 2010505866A5
- Authority
- JP
- Japan
- Prior art keywords
- ketoconazole enantiomer
- ketoconazole
- patient
- enantiomer
- substantially free
- 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.)
- Pending
Links
- 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 84
- 238000000034 method Methods 0.000 claims 21
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 14
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 14
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 9
- 206010012601 diabetes mellitus Diseases 0.000 claims 7
- 229960004125 ketoconazole Drugs 0.000 claims 6
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 5
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims 5
- 229960005370 atorvastatin Drugs 0.000 claims 5
- 235000012000 cholesterol Nutrition 0.000 claims 5
- -1 2S, 4R ketoconazole enantiomer 2S, 4R ketoconazole enantiomer Chemical class 0.000 claims 4
- FJLGEFLZQAZZCD-MCBHFWOFSA-N (3R,5S)-fluvastatin Chemical compound C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 FJLGEFLZQAZZCD-MCBHFWOFSA-N 0.000 claims 3
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims 3
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims 3
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 3
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 claims 3
- 229960003765 fluvastatin Drugs 0.000 claims 3
- 229960004844 lovastatin Drugs 0.000 claims 3
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical group C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims 3
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims 3
- 229960002797 pitavastatin Drugs 0.000 claims 3
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims 3
- 229960002965 pravastatin Drugs 0.000 claims 3
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 3
- 229960000672 rosuvastatin Drugs 0.000 claims 3
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims 3
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 claims 3
- 229960002855 simvastatin Drugs 0.000 claims 3
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 3
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 206010019851 Hepatotoxicity Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 238000008214 LDL Cholesterol Methods 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- IXZISFNWUWKBOM-ARQDHWQXSA-N fructosamine Chemical compound NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O IXZISFNWUWKBOM-ARQDHWQXSA-N 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 210000003494 hepatocyte Anatomy 0.000 claims 2
- 231100000304 hepatotoxicity Toxicity 0.000 claims 2
- 230000007686 hepatotoxicity Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 239000003550 marker Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 229940123934 Reductase inhibitor Drugs 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000002641 glycemic effect Effects 0.000 claims 1
- 231100000334 hepatotoxic Toxicity 0.000 claims 1
- 230000003082 hepatotoxic effect Effects 0.000 claims 1
- 230000003908 liver function Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84896306P | 2006-10-02 | 2006-10-02 | |
| PCT/US2007/080186 WO2008042898A2 (en) | 2006-10-02 | 2007-10-02 | Ketoconazole enantiomer in humans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010505866A JP2010505866A (ja) | 2010-02-25 |
| JP2010505866A5 true JP2010505866A5 (https=) | 2010-11-25 |
Family
ID=39269161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009531558A Pending JP2010505866A (ja) | 2006-10-02 | 2007-10-02 | ヒトにおけるケトコナゾールエナンチオマー |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US9198906B2 (https=) |
| EP (1) | EP2076265A4 (https=) |
| JP (1) | JP2010505866A (https=) |
| AU (1) | AU2007303219A1 (https=) |
| BR (1) | BRPI0719835A2 (https=) |
| CA (1) | CA2664800A1 (https=) |
| IL (1) | IL197986A0 (https=) |
| NO (1) | NO20091593L (https=) |
| NZ (1) | NZ576569A (https=) |
| RU (1) | RU2009116632A (https=) |
| WO (1) | WO2008042898A2 (https=) |
| ZA (1) | ZA200902127B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1853266B1 (en) * | 2005-01-10 | 2011-10-12 | Cortendo AB (publ) | 2s,4r ketoconazole for treating diabetes, metabolic syndrome and other conditions |
| US20100280046A1 (en) * | 2006-01-10 | 2010-11-04 | Diobex, Inc. | Methods and Compositions for Treating Prostate Cancer, Benign Prostatic Hypertrophy, Polycystic Ovary Syndrome and Other Conditions |
| RU2009116632A (ru) | 2006-10-02 | 2010-11-10 | Кортендо Инвест, Аб (Se) | Энантиомер кетоконазола у людей |
| WO2015048311A1 (en) * | 2013-09-25 | 2015-04-02 | Cortendo Ab (Publ) | Novel functionalized 5-(phenoxymethyl)-1,3-dioxane analogs exhibitng cytochrome p450 inhibition |
| 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 |
| WO2020180784A1 (en) * | 2019-03-04 | 2020-09-10 | Strongbridge Dublin Limited | Methods of treating disease with levoketoconazole |
Family Cites Families (41)
| 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 |
| WO1994014447A1 (en) * | 1992-12-22 | 1994-07-07 | Sepracor, Inc. | Methods and compositions of (-) ketoconazole for treating fungal yeast and dermatophyte infections |
| AU5851594A (en) | 1992-12-22 | 1994-07-19 | Georgetown University | 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 |
| US6642236B1 (en) * | 1998-12-14 | 2003-11-04 | Cortendo Ab | Methods for prophylactic treatment of cardiovascular disease with inhibitor of cortisol synthesis |
| SI0779810T1 (en) | 1994-08-09 | 2003-12-31 | Cortendo Ab | Use of ketoconazole and related substances in medicaments for treatment of type ii diabetes |
| 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 |
| US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| AU749271B2 (en) | 1997-07-01 | 2002-06-20 | Agouron Pharmaceuticals, Inc. | Glucagon antagonists/inverse agonists |
| JP2002534512A (ja) | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドｇｌｐ−１アゴニスト |
| PT1171465E (pt) | 1999-03-29 | 2004-12-31 | Uutech Ltd | Analogos de petido inibidor gastrico e sua utilizacao para o tratamento de diabetes |
| AU4055400A (en) | 1999-04-02 | 2000-10-23 | Neurogen Corporation | Aryl and heteroaryl fused aminoalkyl-imidazole derivatives and their use as antidiabetics |
| WO2000069810A1 (en) | 1999-05-17 | 2000-11-23 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| GB9915625D0 (en) | 1999-07-02 | 1999-09-01 | Cortendo Ab | Method |
| RU2269354C2 (ru) | 1999-09-28 | 2006-02-10 | Байер Корпорейшн | Агонисты рецептора-3(r3) пептида-активатора гипофизарной аденилатциклазы(расар) и способы их фармакологического применения |
| GB0001449D0 (en) | 2000-01-21 | 2000-03-08 | Cortendo Ab | Compositions |
| US20020055512A1 (en) * | 2000-01-21 | 2002-05-09 | Cortendo Ab. | Compositions for delivery of a cortisol antagonist |
| WO2002000681A1 (en) | 2000-06-27 | 2002-01-03 | 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 |
| AU2002337119A1 (en) | 2001-09-21 | 2003-04-07 | 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 |
| CA2461363A1 (en) | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
| BR0307595A (pt) * | 2002-02-07 | 2005-02-01 | Pfizer | Uso de inibidores de pde5 tal como sildenafil no tratamento de sìndrome de ovário policìstico |
| WO2004052390A1 (en) | 2002-12-11 | 2004-06-24 | Amylin Pharmaceuticals, Inc. | Methods and compositions for treating polycystic ovary syndrome |
| WO2004080414A2 (en) * | 2003-03-12 | 2004-09-23 | Mullally John P | Composition and method for treating inflammations by reducing c-reactive protein |
| WO2005113516A1 (en) | 2004-05-14 | 2005-12-01 | 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 |
| EP1853266B1 (en) | 2005-01-10 | 2011-10-12 | Cortendo AB (publ) | 2s,4r ketoconazole for treating diabetes, metabolic syndrome and other conditions |
| 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 |
| US20100280046A1 (en) * | 2006-01-10 | 2010-11-04 | Diobex, Inc. | Methods and Compositions for Treating Prostate Cancer, Benign Prostatic Hypertrophy, Polycystic Ovary Syndrome and Other Conditions |
| RU2009116632A (ru) | 2006-10-02 | 2010-11-10 | Кортендо Инвест, Аб (Se) | Энантиомер кетоконазола у людей |
| US9394290B2 (en) | 2010-10-21 | 2016-07-19 | Universitaet Des Saarlandes Campus Saarbruecken | Selective CYP11B1 inhibitors for the treatment of cortisol dependent diseases |
-
2007
- 2007-10-02 RU RU2009116632/15A patent/RU2009116632A/ru not_active Application Discontinuation
- 2007-10-02 CA CA002664800A patent/CA2664800A1/en not_active Abandoned
- 2007-10-02 AU AU2007303219A patent/AU2007303219A1/en not_active Abandoned
- 2007-10-02 EP EP07868351A patent/EP2076265A4/en not_active Withdrawn
- 2007-10-02 WO PCT/US2007/080186 patent/WO2008042898A2/en not_active Ceased
- 2007-10-02 US US12/443,531 patent/US9198906B2/en active Active
- 2007-10-02 ZA ZA200902127A patent/ZA200902127B/xx unknown
- 2007-10-02 JP JP2009531558A patent/JP2010505866A/ja active Pending
- 2007-10-02 NZ NZ576569A patent/NZ576569A/en not_active IP Right Cessation
- 2007-10-02 BR BRPI0719835-3A2A patent/BRPI0719835A2/pt not_active IP Right Cessation
-
2009
- 2009-04-05 IL IL197986A patent/IL197986A0/en unknown
- 2009-04-22 NO NO20091593A patent/NO20091593L/no not_active Application Discontinuation
-
2015
- 2015-11-18 US US14/944,258 patent/US20160067243A1/en not_active Abandoned
-
2018
- 2018-01-09 US US15/865,631 patent/US20180125841A1/en not_active Abandoned
-
2019
- 2019-03-13 US US16/351,797 patent/US20190209555A1/en not_active Abandoned
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