CA2781627C - 6-substituted estradiol derivatives and methods of use - Google Patents

6-substituted estradiol derivatives and methods of use Download PDF

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Publication number
CA2781627C
CA2781627C CA2781627A CA2781627A CA2781627C CA 2781627 C CA2781627 C CA 2781627C CA 2781627 A CA2781627 A CA 2781627A CA 2781627 A CA2781627 A CA 2781627A CA 2781627 C CA2781627 C CA 2781627C
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CA
Canada
Prior art keywords
hydrogen
alkenyl
compound
methyl
integer
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 - Fee Related
Application number
CA2781627A
Other languages
English (en)
French (fr)
Other versions
CA2781627A1 (en
Inventor
James G. Yarger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Endece LLC
Original Assignee
Endece LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Endece LLC filed Critical Endece LLC
Publication of CA2781627A1 publication Critical patent/CA2781627A1/en
Application granted granted Critical
Publication of CA2781627C publication Critical patent/CA2781627C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
    • C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
    • C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C07J1/0074—Esters
    • 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
    • C07J41/0044—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an estrane or gonane skeleton, including 18-substituted derivatives and derivatives where position 17-beta is substituted by a carbon atom not directly bonded to another carbon atom and not being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N5/00—Undifferentiated human, animal or plant cells, e.g. cell lines; Tissues; Cultivation or maintenance thereof; Culture media therefor
    • C12N5/06—Animal cells or tissues; Human cells or tissues
    • C12N5/0602—Vertebrate cells
    • C12N5/0693—Tumour cells; Cancer cells
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2501/00—Active agents used in cell culture processes, e.g. differentation
    • C12N2501/30—Hormones
    • C12N2501/38—Hormones with nuclear receptors
    • C12N2501/39—Steroid hormones
    • C12N2501/392—Sexual steroids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Zoology (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • General Engineering & Computer Science (AREA)
  • Cell Biology (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2781627A 2009-11-30 2010-11-30 6-substituted estradiol derivatives and methods of use Expired - Fee Related CA2781627C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12/627,874 US10174070B2 (en) 2005-09-30 2009-11-30 6-substituted estradiol derivatives and methods of use
US12/627,874 2009-11-30
PCT/US2010/058342 WO2011066542A2 (en) 2009-11-30 2010-11-30 6-substituted estradiol derivatives and methods of use

Publications (2)

Publication Number Publication Date
CA2781627A1 CA2781627A1 (en) 2011-06-03
CA2781627C true CA2781627C (en) 2017-02-28

Family

ID=44067274

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2781627A Expired - Fee Related CA2781627C (en) 2009-11-30 2010-11-30 6-substituted estradiol derivatives and methods of use

Country Status (12)

Country Link
US (2) US10174070B2 (enExample)
EP (1) EP2507253B1 (enExample)
JP (1) JP5898625B2 (enExample)
KR (2) KR20120095461A (enExample)
CN (1) CN102753564B (enExample)
AU (3) AU2010324632A1 (enExample)
CA (1) CA2781627C (enExample)
DK (1) DK2507253T3 (enExample)
ES (1) ES2568941T3 (enExample)
MX (1) MX342436B (enExample)
SG (1) SG181126A1 (enExample)
WO (1) WO2011066542A2 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10174070B2 (en) 2005-09-30 2019-01-08 Endece Llc 6-substituted estradiol derivatives and methods of use
ES2605960T3 (es) * 2010-09-14 2017-03-17 Endece, Llc Derivados de desmetil-estradiol 6-sustituido como agonistas del RE-beta
SG193380A1 (en) 2011-03-21 2013-10-30 Endece Llc 6-substituted estradiol derivatives for use in remyelination of nerve axons
EP2688901B1 (en) * 2011-03-25 2019-05-08 Université Laval INHIBITORS OF 17ß-HSD1, 17ß-HSD3 AND 17ß-HSD10
CN104936971B (zh) * 2013-04-18 2017-10-13 西安力邦医药科技有限责任公司 具有抗癌活性的7‑α‑[9‑(4，4，5，5，5‑五氟戊基亚硫酰基)壬基]‑雌甾‑1，3，5(10)‑三烯‑3，17β‑二醇的酯类衍生物及其制备方法
JP2017512769A (ja) * 2014-03-19 2017-05-25 エンディース エルエルシーＥｎｄｅｃｅ，Ｌｌｃ アルツハイマー病の治療のための６−置換エストラジオール誘導体
CN114644673B (zh) * 2020-12-19 2023-12-26 上海喀露蓝科技有限公司 一种雌二醇衍生物、其制备方法及其在医药上的用途
CN113956321B (zh) * 2021-10-22 2023-11-03 郑州安图生物工程股份有限公司 雌二醇6位葡萄糖醛酸苷及其制备方法和应用
CN115505019B (zh) * 2022-11-07 2024-01-26 南宁师范大学 7-酰胺取代雌甾类化合物及其制备方法和应用

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE258820C (enExample)
US2867630A (en) 1958-06-09 1959-01-06 Upjohn Co 6-fluoro androstenes
GB853012A (en) 1958-06-26 1960-11-02 British Drug Houses Ltd 1:6-dimethyl aromatic steroids and the preparation thereof
US3130210A (en) 1962-11-14 1964-04-21 Olin Mathieson Estradiol derivatives
NL122154C (enExample) 1963-10-18
US3377363A (en) 1966-04-13 1968-04-09 Abbott Lab delta5(10)-6-hydroxymethyl-estrene compounds
DE1906716A1 (de) * 1969-02-06 1970-08-20 Schering Ag 6,7-Disubstituierte OEstratriene
DK290774A (enExample) 1973-06-08 1975-02-03 Schering Ag
DE2832606A1 (de) 1978-07-21 1980-01-31 Schering Ag Verfahren zur herstellung von 7 alpha -methyl-oestrogenen
US4732904A (en) 1984-12-24 1988-03-22 Morgan Lee R Antiestrogenic hydrazones
GB8517360D0 (en) 1985-07-09 1985-08-14 Erba Farmitalia Substituted androsta-1,4-diene-3,17-diones
DD258820A1 (de) 1986-06-13 1988-08-03 Adw Ddr Verfahren zur herstellung von 6beta-hydroxy-methyl-androsta-1,4-dien-3,17-dion
GB8615092D0 (en) 1986-06-20 1986-07-23 Erba Farmitalia Androst-4-ene-317-diones
GB8721383D0 (en) 1987-09-11 1987-10-21 Erba Farmitalia Preparation of methylene derivatives
GB8801697D0 (en) 1988-01-26 1988-02-24 Erba Farmitalia Improvements in synthesis of 6-methylene derivatives of androsta-1 4-diene-3 17-dione
US4938763B1 (en) 1988-10-03 1995-07-04 Atrix Lab Inc Biodegradable in-situ forming implants and method of producing the same
US5504074A (en) 1993-08-06 1996-04-02 Children's Medical Center Corporation Estrogenic compounds as anti-angiogenic agents
JPH07215992A (ja) 1993-12-07 1995-08-15 Teikoku Hormone Mfg Co Ltd ６−又は７−置換アンドロスタ−１，４−ジエン誘導体
DE19633349A1 (de) 1996-08-19 1998-02-26 Sigma Tau Ind Farmaceuti Neue 6-Hydroxy- und 6-Oxo-androstan-Derivate, die auf das kardiovaskuläre System wirken und pharmazeutische Zusammensetzungen, die diese enthalten
AU764266B2 (en) 1998-08-11 2003-08-14 Entremed, Inc Use of estrogenic and anti-estrogenic compounds as anti-fungal compounds
WO2001058919A2 (en) 2000-02-11 2001-08-16 Sri International Synthesis of anti-estrogenic and other therapeutic steroids from 21-hydroxy-19-norpregna-4-en-3-one
IT1317031B1 (it) 2000-05-17 2003-05-26 Sigma Tau Ind Farmaceuti Procedimento migliorato per la preparazione di (e,z)3-(2-amminoetossimmino)-androstano-6, 17-dione e di suoi analoghi.
WO2002022645A2 (en) 2000-09-14 2002-03-21 Accelerated Pharmaceuticals, Inc. Method of making 7alpha-methyl-11beta-methoxy estradiol and related compounds with estrogenic activity
AU2004275693A1 (en) 2003-05-28 2005-04-07 Entremed, Inc. Antiangiogenic agents
US8088758B2 (en) 2003-11-12 2012-01-03 Abbott Products Gmbh 17β-hydroxysteroid dehydrogenase type I inhibitors
ATE548375T1 (de) 2004-01-16 2012-03-15 Cedarburg Pharmaceuticals Inc Exemestan und zwischenprodukte davon und verfahren zu dessen herstellung
EP1756139A4 (en) 2004-03-12 2009-07-29 Entremed Inc ANTI-ANGIOGENIC AGENTS
US7419972B2 (en) 2004-07-02 2008-09-02 Schering Ag 2-substituted estra-1,3,5(10)-trien-17-ones as inhibitors of 17β-hydroxy steroid dehydrogenase type 1
US10174070B2 (en) 2005-09-30 2019-01-08 Endece Llc 6-substituted estradiol derivatives and methods of use
US8168621B2 (en) 2005-09-30 2012-05-01 Endece, Llc 6-substituted estradiol derivatives and methods of use
US20080119447A1 (en) 2005-09-30 2008-05-22 James Yarger 6-alkoxyalkyl estradiol derivatives and methods of use
JP5255444B2 (ja) 2005-09-30 2013-08-07 エンディース エルエルシー （ｓ）−６−メチルオキサアルキルエキセメスタン化合物および関連する使用方法
TWI392682B (zh) 2006-04-13 2013-04-11 Sigma Tau Ind Farmaceuti 作為心血管疾病的治療藥物之雄甾烷和雄甾烯的胺基衍生物
JP5290189B2 (ja) 2006-11-30 2013-09-18 エンディース エルエルシー ６−アルコキシアルキルエストラジオール誘導体およびその使用
ES2605960T3 (es) 2010-09-14 2017-03-17 Endece, Llc Derivados de desmetil-estradiol 6-sustituido como agonistas del RE-beta

Also Published As

Publication number Publication date
KR20180095742A (ko) 2018-08-27
MX342436B (es) 2016-09-29
CA2781627A1 (en) 2011-06-03
ES2568941T3 (es) 2016-05-05
US20100130463A1 (en) 2010-05-27
CN102753564A (zh) 2012-10-24
CN102753564B (zh) 2017-04-05
US10174070B2 (en) 2019-01-08
WO2011066542A3 (en) 2011-10-20
MX2012006169A (es) 2012-11-12
AU2018203658A1 (en) 2018-06-14
EP2507253B1 (en) 2016-03-30
EP2507253A2 (en) 2012-10-10
WO2011066542A2 (en) 2011-06-03
US10723757B2 (en) 2020-07-28
EP2507253A4 (en) 2013-05-22
KR20120095461A (ko) 2012-08-28
SG181126A1 (en) 2012-07-30
AU2016238850A1 (en) 2016-10-20
KR102048457B1 (ko) 2019-11-25
AU2010324632A1 (en) 2012-06-14
JP2013512260A (ja) 2013-04-11
JP5898625B2 (ja) 2016-04-06
DK2507253T3 (en) 2016-07-04
US20190135853A1 (en) 2019-05-09

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