JP7034093B2 - 胆汁酸誘導体、特に、オベチコール酸の合成のための中間体 - Google Patents

胆汁酸誘導体、特に、オベチコール酸の合成のための中間体 Download PDF

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JP7034093B2
JP7034093B2 JP2018560597A JP2018560597A JP7034093B2 JP 7034093 B2 JP7034093 B2 JP 7034093B2 JP 2018560597 A JP2018560597 A JP 2018560597A JP 2018560597 A JP2018560597 A JP 2018560597A JP 7034093 B2 JP7034093 B2 JP 7034093B2
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JP2019516720A5 (OSRAM
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チャールズ ウェイマウス‐ウイルソン アレクサンダー
コムスタ ゾフィア
ウォリス ローラ
エバンズ ティモシー
デービス イエウアン
オッター カール
バチェラー リース
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エヌゼットピー ユーケー リミテッド
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005—Ketals
    • C07J21/006—Ketals at position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005—Ketals
    • C07J21/008—Ketals at position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
JP2018560597A 2016-05-18 2017-05-18 胆汁酸誘導体、特に、オベチコール酸の合成のための中間体 Active JP7034093B2 (ja)

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GBGB1608777.7A GB201608777D0 (en) 2016-05-18 2016-05-18 Compounds
GB1608777.7 2016-05-18
PCT/GB2017/051385 WO2017199033A1 (en) 2016-05-18 2017-05-18 Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid

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JP2019516720A JP2019516720A (ja) 2019-06-20
JP2019516720A5 JP2019516720A5 (OSRAM) 2020-07-02
JP7034093B2 true JP7034093B2 (ja) 2022-03-11

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US (2) US10968250B2 (OSRAM)
EP (2) EP3458469B1 (OSRAM)
JP (1) JP7034093B2 (OSRAM)
KR (1) KR102458265B1 (OSRAM)
CN (1) CN109415407B (OSRAM)
AU (1) AU2017266539B2 (OSRAM)
CA (1) CA3024281A1 (OSRAM)
EA (1) EA037584B1 (OSRAM)
ES (2) ES2878577T3 (OSRAM)
GB (1) GB201608777D0 (OSRAM)
HR (1) HRP20211128T1 (OSRAM)
HU (1) HUE054851T2 (OSRAM)
MX (1) MX378591B (OSRAM)
PT (1) PT3458469T (OSRAM)
WO (1) WO2017199033A1 (OSRAM)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201608776D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds
EP3431486A1 (en) * 2017-07-18 2019-01-23 Bionice, S.L.U. Process and intermediates for the synthesis of obeticholic acid and derivatives thereof
GB201812382D0 (en) 2018-07-30 2018-09-12 Nzp Uk Ltd Compounds
CN111138509B (zh) * 2018-11-02 2022-12-06 东莞东阳光药物研发有限公司 奥贝胆酸的制备方法
CN111072744B (zh) * 2019-12-03 2021-09-14 江苏佳尔科药业集团股份有限公司 一种以ba为原料合成熊去氧胆酸的方法
CN114315945A (zh) * 2020-09-28 2022-04-12 四川澄华生物科技有限公司 一种胆甾酸及其衍生物的除杂方法
CN112341516B (zh) * 2020-11-14 2022-07-15 湖南科瑞生物制药股份有限公司 5,6-环氧类固醇类化合物及其制备方法和应用
EP4423105A2 (en) * 2021-11-02 2024-09-04 Sandhill One, LLC High purity non-animal derived udca

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007080951A1 (ja) 2006-01-12 2007-07-19 Mitsubishi Chemical Corporation ステロイド化合物の製造方法
WO2016079520A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 6.alpha.-alkyl-6,7-dione steroids as intermediates for the production of steroidal fxr modulators
WO2016079519A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 6.alpha.-alkyl-3,7-dione steroids as intermediates for the production of steroidal fxr modulators
WO2016079518A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators
WO2016079517A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 6-alkyl-7-hydroxy-4-en-3-one steroids as intermediates for the production of steroidal fxr modulators

Family Cites Families (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2624748A (en) 1950-09-09 1953-01-06 Upjohn Co Bisnorchola-4, 6-dien-3-one-22-al
US4289872A (en) 1979-04-06 1981-09-15 Allied Corporation Macromolecular highly branched homogeneous compound based on lysine units
US5229490A (en) 1987-05-06 1993-07-20 The Rockefeller University Multiple antigen peptide system
JPH07505915A (ja) 1992-04-14 1995-06-29 コーネル　リサーチ　ファウンデーション、インコーポレーテッド 樹枝状巨大分子およびその製造法
WO1994019366A1 (en) 1993-02-26 1994-09-01 Magainin Pharmaceuticals Inc. Chemical synthesis of squalamine
US5643575A (en) 1993-10-27 1997-07-01 Enzon, Inc. Non-antigenic branched polymer conjugates
US5932462A (en) 1995-01-10 1999-08-03 Shearwater Polymers, Inc. Multiarmed, monofunctional, polymer for coupling to molecules and surfaces
AU2002308295B2 (en) 2001-03-12 2007-08-23 Intercept Pharmaceuticals, Inc. Steroids as agonists for FXR
US20090062256A1 (en) 2001-06-01 2009-03-05 Bristol-Myers Squibb Pharma Company LACTAMS SUBSTITUTED BY CYCLIC SUCCINATES AS INHIBITORS OF Abeta PROTEIN PRODUCTION
JP4758608B2 (ja) 2001-11-07 2011-08-31 ネクター セラピューティックス 分枝ポリマーおよびそれらの結合体
EP1568706A1 (en) 2004-02-26 2005-08-31 Intercept Pharmaceuticals, Inc. Novel steroid agonist for FXR
ITMI20050912A1 (it) 2005-05-19 2006-11-20 Erregierre Spa Processo di preparazione di acidi 3-a-ya(b)-diidrossi-6-a(b)-alchil-5b-colanici
CN101374854A (zh) * 2006-01-12 2009-02-25 三菱化学株式会社 甾类化合物的制备方法
CN101395170A (zh) 2006-02-14 2009-03-25 英特塞普特药品公司 用于预防或治疗fxr介导的疾病或状态的作为fxr配体的胆汁酸衍生物
EP2040713B1 (en) 2006-06-27 2014-06-18 Intercept Pharmaceuticals Inc. Bile acid derivatives as fxr ligands for the prevention or treatment of fxr-mediated deseases or conditions
CA2928178C (en) 2007-01-19 2019-09-10 Intercept Pharmaceuticals, Inc. Tgr5 modulators and methods of use thereof
EP2324046B1 (en) 2008-07-30 2014-09-03 Intercept Pharmaceuticals, Inc. Tgr5 modulators and methods of use thereof
NO2698375T3 (OSRAM) 2008-11-19 2018-07-21
EP3150620B1 (en) 2008-11-19 2020-01-08 Intercept Pharmaceuticals, Inc. Tgr5 modulators and methods of use thereof
US8829213B2 (en) 2009-07-29 2014-09-09 The University Of Chicago Liver X receptor agonists
CA2877122C (en) 2012-06-19 2020-04-28 Intercept Pharmaceuticals, Inc. Preparation, uses and solid forms of obeticholic acid
KR102068381B1 (ko) 2012-10-26 2020-01-20 인터셉트 파마슈티컬즈, 인크. 담즙산 유도체의 제조 방법
CA2891348C (en) 2012-11-28 2020-04-28 Intercept Pharmaceuticals, Inc. Treatment of pulmonary disease
US20140206657A1 (en) * 2013-01-18 2014-07-24 City Of Hope Bile acid analog tgr5 agonists
EP2997035B8 (en) 2013-05-14 2018-05-23 Intercept Pharmaceuticals, Inc. 11-hydroxyl-6-substituted-derivatives of bile acids and amino acid conjugates thereof as farnesoid x receptor modulators
BR112015029318A2 (pt) 2013-05-24 2017-07-25 Nestec Sa marcadores específicos de caminhos para diagnóstico da síndrome do intestino irritável
WO2015183794A1 (en) 2014-05-27 2015-12-03 City Of Hope Tgr5 agonist complexes for treating diabetes and cancer
EP3149019B1 (en) 2014-05-29 2019-12-04 Bar Pharmaceuticals S.r.l. Cholane derivatives for use in the treatment and/or prevention of fxr and tgr5/gpbar1 mediated diseases
HK1243930A1 (zh) 2014-11-06 2018-07-27 英安塔制药有限公司 作爲fxr/tgr5激动剂的胆汁酸类似物和其使用方法
US11578097B2 (en) 2014-11-26 2023-02-14 Enanta Pharmaceuticals, Inc. Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof
US10208081B2 (en) 2014-11-26 2019-02-19 Enanta Pharmaceuticals, Inc. Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof
WO2016086134A1 (en) 2014-11-26 2016-06-02 Enanta Pharmaceuticals, Inc. Bile acid derivatives as fxr/tgr5 agonists and methods of use thereof
MX2017006833A (es) 2014-11-26 2018-02-13 Enanta Pharm Inc Análogos de ácido biliar como agonistas de fxr/tgr5 y métodos para el uso de los mismos.
CN105348365A (zh) * 2014-12-03 2016-02-24 四川百利药业有限责任公司 一种胆酸衍生物及其制备方法、药物组合物和用途
CN106279328A (zh) 2015-05-20 2017-01-04 重庆药友制药有限责任公司 一种制备6α-烷基鹅去氧胆酸的方法
TW201700447A (zh) 2015-06-19 2017-01-01 英特賽普醫藥品公司 Tgr5調控劑及其用法
CN106397522A (zh) 2015-07-31 2017-02-15 中国人民解放军军事医学科学院毒物药物研究所 3,7‑二（叔丁基二甲基硅基氧基）‑6‑烯‑5β‑胆烷‑24‑酸甲酯
CN106478759A (zh) 2015-08-31 2017-03-08 陕西合成药业股份有限公司 奥贝胆酸衍生物及其制备方法和用途
CN106478756A (zh) 2015-09-02 2017-03-08 中美华世通生物医药科技（武汉）有限公司 Oca-e单晶及其制备方法和用途
CN106518946A (zh) 2015-09-10 2017-03-22 上海迪诺医药科技有限公司 磺酰脲衍生物、其药物组合物及应用
GB201608776D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds
GB201608779D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007080951A1 (ja) 2006-01-12 2007-07-19 Mitsubishi Chemical Corporation ステロイド化合物の製造方法
WO2016079520A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 6.alpha.-alkyl-6,7-dione steroids as intermediates for the production of steroidal fxr modulators
WO2016079519A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 6.alpha.-alkyl-3,7-dione steroids as intermediates for the production of steroidal fxr modulators
WO2016079518A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators
WO2016079517A1 (en) 2014-11-19 2016-05-26 Dextra Laboratories Limited 6-alkyl-7-hydroxy-4-en-3-one steroids as intermediates for the production of steroidal fxr modulators

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Biosci. Biotechnol. Biochem.，68，2004年，1332-1337
Chemistry and Physics of Lipids，2001年，109，135-143
J. Org. Chem.，2002年，67，6764-6771

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KR102458265B1 (ko) 2022-10-25
HRP20211128T1 (hr) 2022-01-07
CN109415407A (zh) 2019-03-01
US20190284227A1 (en) 2019-09-19
EA201892514A1 (ru) 2019-05-31
CN109415407B (zh) 2021-08-17
EP3458469A1 (en) 2019-03-27
PT3458469T (pt) 2021-06-11
CA3024281A1 (en) 2017-11-23
MX378591B (es) 2025-03-11
MX2018014164A (es) 2019-04-01
US10968250B2 (en) 2021-04-06
AU2017266539B2 (en) 2021-04-15
EP3848382A1 (en) 2021-07-14
ES2878577T3 (es) 2021-11-19
US20210179661A1 (en) 2021-06-17
GB201608777D0 (en) 2016-06-29
BR112018073488A2 (pt) 2019-04-09
EP3848382C0 (en) 2023-11-29
KR20190009322A (ko) 2019-01-28
EA037584B1 (ru) 2021-04-16
EP3848382B1 (en) 2023-11-29
ES2970336T3 (es) 2024-05-28
WO2017199033A1 (en) 2017-11-23
HUE054851T2 (hu) 2021-10-28
EP3458469B1 (en) 2021-04-14
AU2017266539A1 (en) 2018-11-15
JP2019516720A (ja) 2019-06-20
US11479577B2 (en) 2022-10-25

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