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 GBGB1420593.4A external-priority patent/GB201420593D0/en
Priority claimed from GBGB1420594.2A external-priority patent/GB201420594D0/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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Classifications

    • 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
GBGB1420593.4A GB201420593D0 (en) 2014-11-19 2014-11-19 Compounds
GBGB1420594.2A GB201420594D0 (en) 2014-11-19 2014-11-19 Compounds
GB1420593.4 2014-11-19
GB1420594.2 2014-11-19
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 (enExample)
EP (1) EP3221332B1 (enExample)
JP (1) JP6724004B2 (enExample)
KR (1) KR102526632B1 (enExample)
CN (1) CN107108687B (enExample)
CA (1) CA2968301C (enExample)
DK (1) DK3221332T3 (enExample)
EA (1) EA033445B1 (enExample)
ES (1) ES2733643T3 (enExample)
HK (1) HK1244285B (enExample)
MX (1) MX375864B (enExample)
PL (1) PL3221332T3 (enExample)
TW (1) TWI686400B (enExample)
WO (1) WO2016079518A1 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA033427B1 (ru) 2014-11-19 2019-10-31 Nzp Uk Ltd 6-алкил-7-гидрокси-4-ен-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr
ES2748692T3 (es) 2014-11-19 2020-03-17 Nzp Uk Ltd Esteroides 6.alfa.-alquil-3,7-diona como intermedios para la producción de moduladores FXR de esteroides
JP6698085B2 (ja) 2014-11-19 2020-05-27 エヌゼットピー ユーケー リミテッド ステロイドFXRモジュレーター製造のための中間体としての6α−アルキル−6,7−ジオン−ステロイド
CA3009149A1 (en) * 2015-12-22 2017-06-29 Intercept Pharmaceuticals, Inc. Polymorphic crystalline forms of obeticholic acid
GB201608777D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Compounds
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
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
CN109467538A (zh) * 2017-09-07 2019-03-15 和记黄埔医药(上海)有限公司 环烯烃取代的杂芳环类化合物及其用途
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
GB202416085D0 (en) 2024-10-31 2024-12-18 Nzp Uk Ltd Reduction process

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
ATE156158T1 (de) 1992-04-14 1997-08-15 Cornell Res Foundation Inc Makromoleküle auf basis von dendritischen polymeren und verfahren zur herstellung
AU6392894A (en) 1993-02-26 1994-09-14 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
DK1392714T3 (da) 2001-03-12 2006-01-09 Intercept Pharmaceuticals Inc Steroider som agonister 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
EP1446438A2 (en) 2001-11-07 2004-08-18 Nektar Therapeutics Al, Corporation 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
DK2040713T3 (da) 2006-06-27 2014-09-29 Intercept Pharmaceuticals Inc Galdesyrederivater som fxr-ligander til forebyggelsen eller behandlingen af fxr-medierede sygdomme eller tilstande
CA2928178C (en) 2007-01-19 2019-09-10 Intercept Pharmaceuticals, Inc. Tgr5 modulators and methods of use thereof
US8796249B2 (en) * 2008-07-30 2014-08-05 Intercept Pharmaceuticals, Inc. TGR5 modulators and methods of use thereof
AU2009316484B2 (en) * 2008-11-19 2015-04-16 Intercept Pharmaceuticals, Inc. TGR5 modulators and methods of use thereof
HUE039171T2 (hu) 2008-11-19 2018-12-28 Intercept Pharmaceuticals Inc TGR5 modulátorok és azok alkalmazási eljárása
JP2013500986A (ja) 2009-07-29 2013-01-10 ザ・ユニバーシティ・オブ・シカゴ 肝臓x受容体アゴニスト
ES2822375T3 (es) 2012-06-19 2021-04-30 Intercept Pharmaceuticals Inc Preparación de la forma no cristalina del ácido obeticólico
NZ707389A (en) 2012-10-26 2018-08-31 Intercept Pharmaceuticals Inc Process for preparing bile acid derivatives
WO2014085474A1 (en) 2012-11-28 2014-06-05 Intercept Pharmaceuticals, Inc. Treatment of pulmonary disease
US20140206657A1 (en) * 2013-01-18 2014-07-24 City Of Hope Bile acid analog tgr5 agonists
CN105377870B (zh) 2013-05-14 2018-04-03 英特塞普特医药品公司 作为法尼醇x受体调节剂的胆汁酸的11‑羟基衍生物及其氨基酸共轭物
CA2913108A1 (en) 2013-05-24 2014-11-27 Nestec S.A. Pathway specific assays for predicting irritable bowel syndrome diagnosis
WO2015183794A1 (en) 2014-05-27 2015-12-03 City Of Hope Tgr5 agonist complexes for treating diabetes and cancer
SI3626725T1 (sl) 2014-05-29 2023-04-28 Bar Pharmaceuticals S.R.L. Derivati holana za uporabo pri zdravljenju in/ali preprečevanju bolezni, posredovanih s FXR in TGR5/GPBAR1
BR112017009657A2 (pt) 2014-11-06 2018-01-23 Enanta Pharmaceuticals, Inc análogos de ácidos biliares como agonistas de fxr/tgr5 e métodos de uso dos mesmos
WO2016079527A1 (en) 2014-11-19 2016-05-26 Tetralogic Birinapant Uk Ltd Combination therapy
JP6698085B2 (ja) 2014-11-19 2020-05-27 エヌゼットピー ユーケー リミテッド ステロイドFXRモジュレーター製造のための中間体としての6α−アルキル−6,7−ジオン−ステロイド
ES2748692T3 (es) 2014-11-19 2020-03-17 Nzp Uk Ltd Esteroides 6.alfa.-alquil-3,7-diona como intermedios para la producción de moduladores FXR de esteroides
EA033427B1 (ru) 2014-11-19 2019-10-31 Nzp Uk Ltd 6-алкил-7-гидрокси-4-ен-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr
US10208081B2 (en) 2014-11-26 2019-02-19 Enanta Pharmaceuticals, Inc. Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof
WO2016086115A1 (en) 2014-11-26 2016-06-02 Enanta Pharmaceuticals, Inc. Tetrazole derivatives of bile acids 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
RU2017121457A (ru) 2014-11-26 2018-12-26 Энанта Фармасьютикалс, Инк. Аналоги желчной кислоты в качестве агонистов fxr/tgr5 и способы их применения
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

Also Published As

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

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