CA2968301C - 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators - Google Patents

5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators Download PDF

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Publication number
CA2968301C
CA2968301C CA2968301A CA2968301A CA2968301C CA 2968301 C CA2968301 C CA 2968301C CA 2968301 A CA2968301 A CA 2968301A CA 2968301 A CA2968301 A CA 2968301A CA 2968301 C CA2968301 C CA 2968301C
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CA
Canada
Prior art keywords
general formula
compound
alkyl
process according
halo
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CA2968301A
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English (en)
French (fr)
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CA2968301A1 (en
Inventor
Alexander Weymouth-Wilson
Zofia KOMSTA
James Boydell
Laura WALLIS
Nathan Bartlett
Montserrat SHELBOURNE
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Nzp Uk Ltd
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Nzp Uk Ltd
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Publication date
Priority claimed from GBGB1420594.2A external-priority patent/GB201420594D0/en
Priority claimed from GBGB1420593.4A external-priority patent/GB201420593D0/en
Priority claimed from GBGB1505674.0A external-priority patent/GB201505674D0/en
Application filed by Nzp Uk Ltd filed Critical Nzp Uk Ltd
Publication of CA2968301A1 publication Critical patent/CA2968301A1/en
Application granted granted Critical
Publication of CA2968301C publication Critical patent/CA2968301C/en
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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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2968301A 2014-11-19 2015-11-19 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators Active CA2968301C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GBGB1420594.2A GB201420594D0 (en) 2014-11-19 2014-11-19 Compounds
GB1420593.4 2014-11-19
GB1420594.2 2014-11-19
GBGB1420593.4A GB201420593D0 (en) 2014-11-19 2014-11-19 Compounds
GBGB1505674.0A GB201505674D0 (en) 2015-04-01 2015-04-01 Compounds
GB1505674.0 2015-04-01
PCT/GB2015/053517 WO2016079518A1 (en) 2014-11-19 2015-11-19 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators

Publications (2)

Publication Number Publication Date
CA2968301A1 CA2968301A1 (en) 2016-05-26
CA2968301C true CA2968301C (en) 2023-05-16

Family

ID=54704020

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2968301A Active CA2968301C (en) 2014-11-19 2015-11-19 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators

Country Status (14)

Country Link
US (1) US10131688B2 (https=)
EP (1) EP3221332B1 (https=)
JP (1) JP6724004B2 (https=)
KR (1) KR102526632B1 (https=)
CN (1) CN107108687B (https=)
CA (1) CA2968301C (https=)
DK (1) DK3221332T3 (https=)
EA (1) EA033445B1 (https=)
ES (1) ES2733643T3 (https=)
HK (1) HK1244285B (https=)
MX (1) MX375864B (https=)
PL (1) PL3221332T3 (https=)
TW (1) TWI686400B (https=)
WO (1) WO2016079518A1 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107207559B (zh) 2014-11-19 2019-10-25 Nzp英国有限公司 作为制备类固醇fxr调节剂的中间体的6-烷基-7-羟基-4-烯-3-酮类固醇
KR102527821B1 (ko) 2014-11-19 2023-05-02 엔제트피 유케이 리미티드 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드
KR102546748B1 (ko) 2014-11-19 2023-06-22 엔제트피 유케이 리미티드 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드
JP2018538331A (ja) * 2015-12-22 2018-12-27 インターセプト ファーマシューティカルズ， インコーポレイテッド オベチコール酸の多型結晶形態
GB201608779D0 (en) * 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds
GB201608776D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds
GB201608777D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Compounds
CN106279331B (zh) * 2016-07-27 2019-06-14 宋火良 胆酸类肝病治疗药物
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
CN113135970B (zh) * 2020-01-20 2024-11-22 成都贝诺科成生物科技有限公司 一种具有抗芽孢活性的化合物及其药用组合物

Family Cites Families (43)

* 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
CA2118130A1 (en) 1992-04-14 1993-10-28 Jean M. J. Frechet Dendritic based macromolecules and method of production
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
ES2248581T3 (es) 2001-03-12 2006-03-16 Intercept Pharmaceuticals, Inc. Esteroides como agonistas de 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
AU2002352524B2 (en) 2001-11-07 2007-10-04 Nektar Therapeutics Branched polymers and their conjugates
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
JP2007210888A (ja) * 2006-01-12 2007-08-23 Mitsubishi Chemicals Corp ステロイド化合物の製造方法
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
US7932244B2 (en) 2006-06-27 2011-04-26 Intercept Pharmaceuticals, Inc. Bile acid derivatives as FXR ligands for the prevention or treatment of FXR-mediated diseases or conditions
KR101555716B1 (ko) 2007-01-19 2015-09-25 인터셉트 파마슈티컬즈, 인크. Ｔｇｒ5 조절제로서의 23-치환 담즙산 및 이의 사용 방법
WO2010014836A2 (en) * 2008-07-30 2010-02-04 Intercept Pharmaceuticals, Inc. Tgr5 modulators and methods of use thereof
DK2698375T3 (en) 2008-11-19 2018-05-28 Intercept Pharmaceuticals Inc TGR5 modulators and methods for using them
ES2774368T3 (es) * 2008-11-19 2020-07-20 Intercept Pharmaceuticals Inc Moduladores de TGR5 y métodos de uso de los mismos
EP2459581A4 (en) 2009-07-29 2012-12-26 Univ Chicago LIVER X-RECEPTOR AGONISTS
SI3336097T1 (sl) 2012-06-19 2021-07-30 Intercept Pharmaceuticals, Inc. Priprava nekristalinične oblike obetiholne kisline
SG11201503247UA (en) 2012-10-26 2015-06-29 Intercept Pharmaceuticals Inc Process for preparing bile acid derivatives
AU2013352288B2 (en) 2012-11-28 2017-11-23 Intercept Pharmaceuticals, Inc. Treatment of pulmonary disease
US20140206657A1 (en) * 2013-01-18 2014-07-24 City Of Hope Bile acid analog tgr5 agonists
TN2015000497A1 (en) 2013-05-14 2017-04-06 Intercept Pharmaceuticals Inc 11-hydroxyl-derivatives of bile acids and amino acid conjugates thereof as farnesoid x receptor modulators
SG11201509371XA (en) 2013-05-24 2015-12-30 Nestec Sa Pathway specific markers for diagnosing irritable bowel syndrome
US10166246B2 (en) 2014-05-27 2019-01-01 City Of Hope TGR5 agonist complexes for treating diabetes and cancer
SMT202000070T1 (it) 2014-05-29 2020-03-13 Bar Pharmaceuticals S R L Derivati del colano per l'uso del trattamento e/o la prevenzione di malattie mediate da fxr e tgr5/gpbar1
SG11201703717SA (en) 2014-11-06 2017-06-29 Enanta Pharm Inc Bile acid analogs an fxr/tgr5 agonists and methods of use thereof
KR102546748B1 (ko) 2014-11-19 2023-06-22 엔제트피 유케이 리미티드 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드
CN107207559B (zh) 2014-11-19 2019-10-25 Nzp英国有限公司 作为制备类固醇fxr调节剂的中间体的6-烷基-7-羟基-4-烯-3-酮类固醇
KR102527821B1 (ko) 2014-11-19 2023-05-02 엔제트피 유케이 리미티드 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드
WO2016079527A1 (en) 2014-11-19 2016-05-26 Tetralogic Birinapant Uk Ltd Combination therapy
EP3223823A4 (en) 2014-11-26 2018-10-17 Enanta Pharmaceuticals, Inc. Bile acid analogs as fxr/tgr5 agonists and methods of use thereof
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
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
JP6861703B2 (ja) 2015-06-19 2021-04-21 インターセプト ファーマシューティカルズ， インコーポレイテッド Ｔｇｒ５修飾物質およびその使用方法
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

Also Published As

Publication number Publication date
JP2017538691A (ja) 2017-12-28
EP3221332A1 (en) 2017-09-27
US20170320907A1 (en) 2017-11-09
EA201790881A8 (ru) 2019-07-31
TWI686400B (zh) 2020-03-01
CN107108687B (zh) 2019-10-29
JP6724004B2 (ja) 2020-07-15
US10131688B2 (en) 2018-11-20
ES2733643T3 (es) 2019-12-02
PL3221332T3 (pl) 2019-10-31
EP3221332B1 (en) 2019-04-24
WO2016079518A1 (en) 2016-05-26
KR102526632B1 (ko) 2023-04-27
CN107108687A (zh) 2017-08-29
MX2017006564A (es) 2018-01-26
KR20170099895A (ko) 2017-09-01
EA201790881A1 (ru) 2017-11-30
DK3221332T3 (da) 2019-07-29
TW201629081A (zh) 2016-08-16
EA033445B1 (ru) 2019-10-31
CA2968301A1 (en) 2016-05-26
MX375864B (es) 2025-03-07
HK1244285B (en) 2020-06-05

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