CA2335551C - Thyroid hormone analogues and methods for their preparation - Google Patents

Thyroid hormone analogues and methods for their preparation Download PDF

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Publication number
CA2335551C
CA2335551C CA002335551A CA2335551A CA2335551C CA 2335551 C CA2335551 C CA 2335551C CA 002335551 A CA002335551 A CA 002335551A CA 2335551 A CA2335551 A CA 2335551A CA 2335551 C CA2335551 C CA 2335551C
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CA
Canada
Prior art keywords
compound
hydrogen
formula
6alkyl
compounds
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
CA002335551A
Other languages
English (en)
French (fr)
Other versions
CA2335551A1 (en
Inventor
Thomas S. Scanlan
Hikari A. I. Yoshihara
Grazia Chiellini
Timothy J. Mitchison
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 California, San Diego
Original Assignee
University of California, San Diego
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 University of California, San Diego filed Critical University of California, San Diego
Publication of CA2335551A1 publication Critical patent/CA2335551A1/en
Application granted granted Critical
Publication of CA2335551C publication Critical patent/CA2335551C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002335551A 1998-06-30 1999-06-28 Thyroid hormone analogues and methods for their preparation Expired - Fee Related CA2335551C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9118598P 1998-06-30 1998-06-30
US60/091,185 1998-06-30
PCT/US1999/014627 WO2000000468A1 (en) 1998-06-30 1999-06-28 Thyroid hormone analogues and methods for their preparation

Publications (2)

Publication Number Publication Date
CA2335551A1 CA2335551A1 (en) 2000-01-06
CA2335551C true CA2335551C (en) 2009-03-03

Family

ID=22226506

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002335551A Expired - Fee Related CA2335551C (en) 1998-06-30 1999-06-28 Thyroid hormone analogues and methods for their preparation

Country Status (13)

Country Link
US (1) US6107517A (enExample)
EP (2) EP1598334A1 (enExample)
JP (1) JP2002519340A (enExample)
KR (1) KR20010053277A (enExample)
AT (1) ATE293595T1 (enExample)
AU (1) AU4840199A (enExample)
CA (1) CA2335551C (enExample)
DE (1) DE69924846T2 (enExample)
DK (1) DK1089968T3 (enExample)
ES (1) ES2241294T3 (enExample)
IL (1) IL140140A0 (enExample)
PT (1) PT1089968E (enExample)
WO (1) WO2000000468A1 (enExample)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5883294A (en) * 1997-06-18 1999-03-16 The Regeants Of The University Of California Selective thyroid hormone analogs
CA2374266A1 (en) * 1999-06-01 2000-12-07 The University Of Texas Southwestern Medical Center Method of treating hair loss using diphenylmethane derivatives
MXPA01012494A (es) 1999-06-01 2002-07-02 Univ Texas Southwestern Med Ct Metodo para tratar perdida capilar con el uso de compuestos sulfonil tiromimeticos.
US6723717B1 (en) 1999-06-01 2004-04-20 The University Of Texas Southwestern Medical Center Sulfur-containing thyroxane derivatives and their use as hair growth promotors
US6680344B1 (en) 1999-06-01 2004-01-20 The University Of Texas Southwestern Medical Center Method of treating hair loss using diphenylmethane derivatives
US20040132830A1 (en) * 2001-01-19 2004-07-08 Finer Jeffrey T Triphenylmethane kinesin inhibitors
US7302347B2 (en) * 2002-12-10 2007-11-27 The Regents Of The University Of California Method for creating specific, high affinity nuclear receptor pharmaceuticals
SE526033C3 (sv) * 2003-11-06 2009-12-08 Metso Paper Inc Silanordning och silkorg för silning av massasuspensioner
EP2428516A1 (en) 2003-11-19 2012-03-14 Metabasis Therapeutics, Inc. Novel phosphorus-containing thyromimetics
US20090232879A1 (en) 2005-05-26 2009-09-17 Metabasis Therapeutics, Inc. Thyromimetics for the Treatment of Fatty Liver Diseases
RU2007148927A (ru) * 2005-05-26 2009-07-10 Метабэйзис Терапьютикс, Инк. (Us) Новые тиреомиметики, содержащие фосфиновую кислоту
WO2007002036A1 (en) * 2005-06-24 2007-01-04 Thomas Lavin Tyroid hormone in burn and adipose deposites
WO2014178892A1 (en) 2013-05-03 2014-11-06 Scanlan Thomas S Use of sobetirome in the treatment of x-linked adrenolenoleukodystrophy
MX382313B (es) * 2016-05-18 2025-03-13 Univ Oregon Health & Science Derivados del sobetiroma.
WO2018094265A2 (en) 2016-11-21 2018-05-24 Viking Therapeutics, Inc. Method of treating glycogen storage disease
AU2018280118B2 (en) 2017-06-05 2021-07-15 Viking Therapeutics, Inc. Compositions for the treatment of fibrosis
EA202091979A1 (ru) 2018-03-22 2021-06-22 Вайкинг Терапьютикс, Инк. Кристаллические формы и способы получения кристаллических форм соединения
EP4775207A2 (en) 2018-12-05 2026-07-15 Viking Therapeutics, Inc. Compositions for the treatment of fibrosis
EP3894383A1 (en) 2018-12-12 2021-10-20 Autobahn Therapeutics, Inc. Novel thyromimetics
CA3130371A1 (en) 2019-03-01 2020-09-10 Autobahn Therapeutics, Inc. Novel thyromimetics
CN115279359A (zh) 2019-11-29 2022-11-01 速通医疗公司 新型拟甲状腺素药
EP4161925A4 (en) 2020-06-09 2024-09-04 Viking Therapeutics, Inc. COMPOSITIONS AND METHODS FOR THE TREATMENT OF LIVER DISEASES
EP4168384A4 (en) 2020-06-17 2024-07-10 Autobahn Therapeutics, Inc. THYROMIMETICS
EP4167986A4 (en) 2020-06-17 2024-11-20 Autobahn Therapeutics, Inc. THYROMIMETICS
AU2022271304A1 (en) 2021-05-06 2023-11-23 Autobahn Therapeutics, Inc. Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitors

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3332957A (en) * 1964-09-02 1967-07-25 Ciba Geigy Corp Amino esters of substituted phenoxy acetic acids
JPS5195049A (en) * 1975-02-12 1976-08-20 * **********so*****no***tsu*****************************************ni*no
US4323691A (en) * 1979-10-09 1982-04-06 Abbott Laboratories Hydroxyaminomethyl derivatives of benzoyl di-substituted α-phenoxyalkanoyl esters
US5883294A (en) * 1997-06-18 1999-03-16 The Regeants Of The University Of California Selective thyroid hormone analogs

Also Published As

Publication number Publication date
KR20010053277A (ko) 2001-06-25
US6107517A (en) 2000-08-22
ES2241294T3 (es) 2005-10-16
ATE293595T1 (de) 2005-05-15
WO2000000468A1 (en) 2000-01-06
DE69924846D1 (de) 2005-05-25
CA2335551A1 (en) 2000-01-06
DE69924846T2 (de) 2006-04-27
AU4840199A (en) 2000-01-17
DK1089968T3 (da) 2005-08-22
IL140140A0 (en) 2002-02-10
EP1089968A4 (en) 2002-08-21
EP1089968A1 (en) 2001-04-11
EP1089968B1 (en) 2005-04-20
PT1089968E (pt) 2005-08-31
EP1598334A1 (en) 2005-11-23
JP2002519340A (ja) 2002-07-02

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