KR100935623B1 - 고지혈증 치료를 위한 회장 담즙산 운반(ｉｂａｔ) 억제활성을 가진 벤조티아제핀 및 벤조티아디아제핀 유도체 - Google Patents
고지혈증 치료를 위한 회장 담즙산 운반(ｉｂａｔ) 억제활성을 가진 벤조티아제핀 및 벤조티아디아제핀 유도체 Download PDFInfo
- Publication number
- KR100935623B1 KR100935623B1 KR1020047003407A KR20047003407A KR100935623B1 KR 100935623 B1 KR100935623 B1 KR 100935623B1 KR 1020047003407 A KR1020047003407 A KR 1020047003407A KR 20047003407 A KR20047003407 A KR 20047003407A KR 100935623 B1 KR100935623 B1 KR 100935623B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- carbamoyl
- carbamoylmethoxy
- alkyl
- carboxy
- 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.)
- Expired - Lifetime
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- 238000011282 treatment Methods 0.000 title claims abstract description 46
- 230000002401 inhibitory effect Effects 0.000 title claims description 25
- 239000003613 bile acid Substances 0.000 title abstract description 37
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 title abstract description 31
- 208000031226 Hyperlipidaemia Diseases 0.000 title abstract description 19
- KAOYLRLQZXRRBD-UHFFFAOYSA-N 1,2,3-benzothiadiazepine Chemical class S1N=NC=CC2=CC=CC=C12 KAOYLRLQZXRRBD-UHFFFAOYSA-N 0.000 title description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 231
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 19
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- 125000003545 alkoxy group Chemical group 0.000 claims description 19
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- 150000002431 hydrogen Chemical class 0.000 claims description 19
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
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Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
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- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| GB0209463.9 | 2002-04-25 | ||
| GB0209463A GB0209463D0 (en) | 2002-04-25 | 2002-04-25 | Chemical compounds |
| PCT/GB2002/004033 WO2003022286A1 (en) | 2001-09-08 | 2002-09-05 | Benzothiazepine and benzothiadiazepine derivatives with ileal bile acid transport (ibat) inhibitory activity for the treatment hyperlipidaemia |
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| KR20040036935A KR20040036935A (ko) | 2004-05-03 |
| KR100935623B1 true KR100935623B1 (ko) | 2010-01-07 |
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| BR0311932A (pt) * | 2002-06-20 | 2005-03-22 | Astrazeneca Ab | Composto, formulação farmacêutica, método para tratar ou prevenir resistência à insulina, uso de um composto, processo para preparar um composto, e, tratamento combinado |
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| AU2008202120B2 (en) * | 2003-04-05 | 2009-12-17 | Albireo Ab | Use of an IBAT inhibitor for the treatment of prophylaxis of constipation |
| GB0314131D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| AR057828A1 (es) * | 2005-09-29 | 2007-12-19 | Astrazeneca Ab | Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica |
| US7528448B2 (en) * | 2006-07-17 | 2009-05-05 | E.I. Du Pont De Nemours And Company | Thin film transistor comprising novel conductor and dielectric compositions |
| US8062824B2 (en) | 2006-07-17 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Thermally imageable dielectric layers, thermal transfer donors and receivers |
| RU2480453C2 (ru) | 2007-03-08 | 2013-04-27 | Альбирео Аб | Новые соединения |
| US7666567B2 (en) | 2007-10-23 | 2010-02-23 | E. I. Du Pont De Nemours And Company | Negative imaging method for providing a patterned metal layer having high conductivity |
| US7666568B2 (en) * | 2007-10-23 | 2010-02-23 | E. I. Du Pont De Nemours And Company | Composition and method for providing a patterned metal layer having high conductivity |
| WO2010062861A2 (en) * | 2008-11-26 | 2010-06-03 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of obesity and diabetes |
| ES2552657T3 (es) | 2010-05-26 | 2015-12-01 | Satiogen Pharmaceuticals, Inc. | Inhibidores del reciclado de ácidos biliares y saciógenos para el tratamiento de diabetes, obesidad, y afecciones gastrointestinales inflamatorias |
| ES2687027T3 (es) | 2010-11-04 | 2018-10-23 | Albireo Ab | Inhibidores de ibat para el tratamiento de enfermedades hepáticas |
| DK2637646T3 (en) * | 2010-11-08 | 2016-08-29 | Albireo Ab | PHARMACEUTICAL COMBINATION CONTAINING AN IBAT inhibitor and a bile acid binder |
| WO2012064268A1 (en) * | 2010-11-08 | 2012-05-18 | Albireo Ab | Ibat inhibitors for treatment of metabolic disorders and related conditions |
| US20120114588A1 (en) * | 2010-11-08 | 2012-05-10 | Albireo Ab | Ibat inhibitors for treatment of metabolic disorders and related conditions |
| AU2012328526B2 (en) * | 2011-10-28 | 2017-05-25 | Shire Human Genetic Therapies, Inc. | Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases |
| US20130108573A1 (en) | 2011-10-28 | 2013-05-02 | Lumena Pharmaceuticals, Inc. | Bile Acid Recycling Inhibitors for Treatment of Hypercholemia and Cholestatic Liver Disease |
| AU2014229050A1 (en) | 2013-03-15 | 2015-10-22 | Lumena Pharmaceuticals Llc | Bile acid recycling inhibitors for treatment of Barrett's esophagus and gastroesophageal reflux disease |
| CA2907230A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| JO3301B1 (ar) | 2013-04-26 | 2018-09-16 | Albireo Ab | تعديلات بلورية على إيلوبيكسيبات |
| CN106659726A (zh) | 2014-06-25 | 2017-05-10 | Ea制药株式会社 | 固体制剂及其着色防止或着色减少方法 |
| EP3012252A1 (en) | 2014-10-24 | 2016-04-27 | Ferring BV | Crystal modifications of elobixibat |
| ES2874669T3 (es) | 2016-02-09 | 2021-11-05 | Albireo Ab | Formulación oral de colestiramina y uso de la misma |
| WO2017138878A1 (en) | 2016-02-09 | 2017-08-17 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| CN108601739B (zh) | 2016-02-09 | 2022-01-04 | 阿尔比里奥公司 | 考来烯胺丸剂及其制备方法 |
| EP3664782B1 (en) | 2017-08-09 | 2025-01-29 | Albireo AB | Cholestyramine pellets, oral cholestyramine formulations and medical use thereof |
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| PL3810581T3 (pl) | 2018-06-20 | 2025-04-28 | Albireo Ab | Modyfikacje kryształu odewiksibatu |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| TWI835997B (zh) | 2019-02-06 | 2024-03-21 | 瑞典商艾爾比瑞歐公司 | 苯并噻氮呯化合物及其用作膽酸調節劑之用途 |
| CN118852054A (zh) * | 2019-02-06 | 2024-10-29 | 阿尔比里奥公司 | 苯并硫杂二氮杂环庚三烯化合物及其用作胆汁酸调节剂的用途 |
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| KR20220061110A (ko) | 2019-09-09 | 2022-05-12 | 이에이 파마 가부시키가이샤 | 1,5-벤조티아제핀 화합물을 제조하기 위한 방법 |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| JP7696898B2 (ja) | 2019-12-04 | 2025-06-23 | アルビレオ・アクチボラグ | ベンゾチア（ジ）アゼピン化合物及び胆汁酸モジュレータとしてのそれらの使用 |
| WO2021110883A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| IL293379B2 (en) | 2019-12-04 | 2026-04-01 | Albireo Ab | Benzothia(dia)azepine compounds and their use as bile acid modulators |
| EP4069247B1 (en) | 2019-12-04 | 2025-03-26 | Albireo AB | Benzothiadiazepine compounds and their use as bile acid modulators |
| TWI877263B (zh) * | 2019-12-04 | 2025-03-21 | 瑞典商艾爾比瑞歐公司 | 苯并噻二氮呯化合物及其作為膽酸調節劑之用途 |
| ES2973355T3 (es) | 2019-12-04 | 2024-06-19 | Albireo Ab | Compuestos de benzotia(di)azepina y su uso como moduladores del ácido biliar |
| WO2021110887A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
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| AR120676A1 (es) | 2019-12-04 | 2022-03-09 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como ácido biliar |
| WO2022029101A1 (en) | 2020-08-03 | 2022-02-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| EP4188541B1 (en) * | 2020-08-03 | 2024-12-25 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| WO2022101379A1 (en) | 2020-11-12 | 2022-05-19 | Albireo Ab | Odevixibat for treating progressive familial intrahepatic cholestasis (pfic) |
| CA3196488A1 (en) | 2020-11-12 | 2022-05-19 | Albireo Ab | Odevixibat for treating progressive familial intrahepatic cholestasis (pfic) |
| BR112023010799A2 (pt) | 2020-12-04 | 2023-10-03 | Albireo Ab | Compostos de benzotia(di)azepina e seus usos como moduladores de ácidos biliares |
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