CA2908577C - Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity - Google Patents

Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity Download PDF

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Publication number
CA2908577C
CA2908577C CA2908577A CA2908577A CA2908577C CA 2908577 C CA2908577 C CA 2908577C CA 2908577 A CA2908577 A CA 2908577A CA 2908577 A CA2908577 A CA 2908577A CA 2908577 C CA2908577 C CA 2908577C
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Canada
Prior art keywords
benzimidazol
diene
androsta
cancer
compound
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Active
Application number
CA2908577A
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English (en)
French (fr)
Other versions
CA2908577A1 (en
Inventor
Vincent C.O. Njar
Purushottamachar Puranik
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.)
University of Maryland Baltimore
Original Assignee
University of Maryland Baltimore
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Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=51659362&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2908577(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by University of Maryland Baltimore filed Critical University of Maryland Baltimore
Priority to CA3151555A priority Critical patent/CA3151555A1/en
Publication of CA2908577A1 publication Critical patent/CA2908577A1/en
Application granted granted Critical
Publication of CA2908577C publication Critical patent/CA2908577C/en
Active legal-status Critical Current
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/472Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41641,3-Diazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41641,3-Diazoles
    • A61K31/41841,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4409Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08Radicals containing only hydrogen and carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J43/00Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2908577A 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity Active CA2908577C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3151555A CA3151555A1 (en) 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361808345P 2013-04-04 2013-04-04
US61/808,345 2013-04-04
US201361808902P 2013-04-05 2013-04-05
US61/808,902 2013-04-05
PCT/US2014/033063 WO2014165815A2 (en) 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3151555A Division CA3151555A1 (en) 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity

Publications (2)

Publication Number Publication Date
CA2908577A1 CA2908577A1 (en) 2014-10-09
CA2908577C true CA2908577C (en) 2022-05-31

Family

ID=51659362

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2908577A Active CA2908577C (en) 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity
CA3151555A Pending CA3151555A1 (en) 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA3151555A Pending CA3151555A1 (en) 2013-04-04 2014-04-04 Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity

Country Status (6)

Country Link
US (2) US9694005B2 (enExample)
EP (2) EP3514147B1 (enExample)
JP (1) JP6417392B2 (enExample)
AU (1) AU2014247941C1 (enExample)
CA (2) CA2908577C (enExample)
WO (1) WO2014165815A2 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10675289B2 (en) 2014-10-02 2020-06-09 University Of Maryland, Baltimore Methods of treating pancreatic cancer
WO2017201683A1 (en) * 2016-05-25 2017-11-30 Merck Sharp & Dohme Corp. Substituted tetrahydroisoquinoline compounds useful as gpr120 agonists
EP3474848A4 (en) * 2016-06-22 2020-04-15 University of Maryland, Baltimore PROCESS FOR PRODUCING NEW GALETERONE ANALOGS AND USES THEREOF
TW201815787A (zh) 2016-09-23 2018-05-01 美商基利科學股份有限公司 磷脂醯肌醇3-激酶抑制劑
TW201813963A (zh) 2016-09-23 2018-04-16 美商基利科學股份有限公司 磷脂醯肌醇3-激酶抑制劑
TW201825465A (zh) 2016-09-23 2018-07-16 美商基利科學股份有限公司 磷脂醯肌醇3-激酶抑制劑
CN106902112B (zh) * 2017-03-07 2019-06-04 中国医学科学院医药生物技术研究所 Imb-a6作为雄激素受体拮抗剂的应用
CN111943889B (zh) * 2020-07-24 2022-07-22 中国医学科学院医药生物技术研究所 一种双芳香基胺类化合物及其制备方法和应用
CN116444599A (zh) * 2022-01-07 2023-07-18 中国科学院上海药物研究所 甾体类化合物及制备方法和用途
WO2024064026A1 (en) * 2022-09-19 2024-03-28 Alterome Therapeutics, Inc. Akt1 modulators
AU2023351192A1 (en) * 2022-09-26 2025-03-27 Alterome Therapeutics, Inc. Akt1 modulators
WO2024091899A1 (en) * 2022-10-25 2024-05-02 University Of Maryland, Baltimore Salts of galeterone and salts of next generation galeterone analogs, and uses thereof

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA129379A (en) 1910-10-18 1910-11-22 John Clarence Bisland Hoe
DE3928177A1 (de) * 1989-04-08 1991-02-28 Thomae Gmbh Dr K Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
IL95975A (en) * 1989-10-24 1997-06-10 Takeda Chemical Industries Ltd N-benzyl- 2-alkylbenzimidazole derivatives, their production and pharmaceutical compositions containing them
DK40192D0 (da) * 1992-03-26 1992-03-26 Neurosearch As Imidazolforbindelser, deres fremstilling og anvendelse
DE10342503A1 (de) * 2003-09-12 2005-04-14 Merck Patent Gmbh Benzyl-Benzimidazolylderivate
PT2206719E (pt) * 2005-03-02 2015-02-05 Univ Maryland Composição farmacêutica compreendendo 3-beta-hidroxi-17- (1-h-benzimidazol-1-il)androsta-5,16-dieno
WO2009100438A2 (en) 2008-02-07 2009-08-13 Massachusetts Eye & Ear Infirmary Compounds that enhance atoh-1 expression
US20100048914A1 (en) * 2008-03-14 2010-02-25 Angela Brodie Novel C-17-Heteroaryl Steroidal Cyp17 Inhibitors/Antiandrogens, In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity
US20110118219A1 (en) * 2008-03-25 2011-05-19 University Of Maryland, Baltimore Novel prodrugs of c-17-heteroaryl steroidal cyp17 inhibitors/antiandrogens: synthesis, in vitro biological activities, pharmacokinetics and antitumor activity
GB201114153D0 (en) * 2009-02-05 2011-10-05 Tokai Pharmaceuticals Inc Combination of a 17 alpha-hydroxylase/c17, 20-lyase inhibitor with an additional therapeutic agent
BRPI1008745A2 (pt) * 2009-02-05 2019-09-17 Tokai Pharmaceuticals Inc pró-fármacos de inibidores esteroidais de cyp17/antiandrogênios
BR112014001440A2 (pt) * 2011-07-18 2017-02-21 Tokai Pharmaceuticals Inc novas composições e métodos para o tratamento de câncer de próstata
SG11201507093WA (en) * 2013-03-14 2015-10-29 Univ Maryland Baltimore Office Of Technology Transfer Androgen receptor down-regulating agents and uses thereof

Also Published As

Publication number Publication date
CA2908577A1 (en) 2014-10-09
CA3151555A1 (en) 2014-10-09
JP6417392B2 (ja) 2018-11-07
AU2014247941C1 (en) 2019-10-31
WO2014165815A2 (en) 2014-10-09
WO2014165815A3 (en) 2014-12-31
AU2014247941A1 (en) 2015-10-22
JP2016515630A (ja) 2016-05-30
EP2991644A4 (en) 2017-02-08
AU2014247941B2 (en) 2017-04-27
US20170266181A1 (en) 2017-09-21
EP3514147B1 (en) 2022-08-03
US10617685B2 (en) 2020-04-14
US9694005B2 (en) 2017-07-04
US20160038476A1 (en) 2016-02-11
EP3514147A1 (en) 2019-07-24
EP2991644B1 (en) 2020-03-25
EP2991644A2 (en) 2016-03-09

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