CA3090070C - Method of synthesizing thyroid hormone analogs and polymorphs thereof - Google Patents

Method of synthesizing thyroid hormone analogs and polymorphs thereof Download PDF

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Publication number
CA3090070C
CA3090070C CA3090070A CA3090070A CA3090070C CA 3090070 C CA3090070 C CA 3090070C CA 3090070 A CA3090070 A CA 3090070A CA 3090070 A CA3090070 A CA 3090070A CA 3090070 C CA3090070 C CA 3090070C
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Prior art keywords
compound
dihydrate
equiv
batch
pharmaceutical composition
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CA3090070A
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English (en)
French (fr)
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CA3090070A1 (en
Inventor
D. Keith Hester
Robert J. Duguid
Martha Kelly
Anna CHASNOFF
Gang Dong
Edwin L. Crow
Rebecca Taub
Charles H. Reynolds
Duk Soon Choi
Lianhe Shu
Ping Wang
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F Hoffmann La Roche AG
Madrigal Pharmaceuticals Inc
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F Hoffmann La Roche AG
Madrigal Pharmaceuticals Inc
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Publication of CA3090070A1 publication Critical patent/CA3090070A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C07D237/16—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicinal Preparation (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Steroid Compounds (AREA)
CA3090070A 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof Active CA3090070C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261702137P 2012-09-17 2012-09-17
US61/702,137 2012-09-17
US201361790432P 2013-03-15 2013-03-15
US61/790,432 2013-03-15
CA2884481A CA2884481C (en) 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2884481A Division CA2884481C (en) 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof

Publications (2)

Publication Number Publication Date
CA3090070A1 CA3090070A1 (en) 2014-03-20
CA3090070C true CA3090070C (en) 2023-01-24

Family

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Family Applications (3)

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CA2884481A Active CA2884481C (en) 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof
CA3090070A Active CA3090070C (en) 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof
CA3111317A Active CA3111317C (en) 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof

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Family Applications After (1)

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CA3111317A Active CA3111317C (en) 2012-09-17 2013-09-17 Method of synthesizing thyroid hormone analogs and polymorphs thereof

Country Status (21)

Country Link
US (8) US9266861B2 (en:Method)
EP (4) EP2895466B1 (en:Method)
JP (7) JP6616688B2 (en:Method)
KR (4) KR20200023528A (en:Method)
CN (2) CN108101851A (en:Method)
AR (1) AR092872A1 (en:Method)
AU (1) AU2013315017C1 (en:Method)
BR (2) BR112015005891A2 (en:Method)
CA (3) CA2884481C (en:Method)
DK (2) DK2895466T3 (en:Method)
ES (2) ES2795450T3 (en:Method)
IL (7) IL288133B2 (en:Method)
IN (1) IN2015DN03133A (en:Method)
MX (2) MX395148B (en:Method)
MY (1) MY170520A (en:Method)
NZ (2) NZ739645A (en:Method)
RU (2) RU2668960C2 (en:Method)
SG (3) SG11201501907YA (en:Method)
TW (4) TWI804870B (en:Method)
WO (1) WO2014043706A1 (en:Method)
ZA (1) ZA201501795B (en:Method)

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AU2013315017B2 (en) 2017-07-27
KR102138750B1 (ko) 2020-07-29
IL275393A (en) 2020-07-30
US11986481B2 (en) 2024-05-21
JP2020015739A (ja) 2020-01-30
CA3111317C (en) 2023-08-29
IL275393B (en) 2022-01-01
IL314360A (en) 2024-09-01
US10376517B2 (en) 2019-08-13
EP4406594A3 (en) 2024-11-06
CN108101851A (zh) 2018-06-01
AU2013315017C1 (en) 2017-11-23
US20240148742A1 (en) 2024-05-09
RU2015114327A (ru) 2016-11-10
IL314360B2 (en) 2025-09-01
EP2895466B1 (en) 2020-03-25
RU2668960C2 (ru) 2018-10-05
ES2907926T3 (es) 2022-04-27
CN105008335B (zh) 2018-12-21
US20190381053A1 (en) 2019-12-19
TW201425300A (zh) 2014-07-01
DK3689853T3 (da) 2022-03-07
IL288133A (en) 2022-01-01
ZA201501795B (en) 2021-10-27
JP6532931B2 (ja) 2019-06-19
SG10201705984XA (en) 2017-08-30
JP6899413B2 (ja) 2021-07-07
IL237628A0 (en) 2015-04-30
EP2895466A4 (en) 2016-08-10
SG11201501907YA (en) 2015-04-29
JP6765408B2 (ja) 2020-10-07
EP4406594A2 (en) 2024-07-31
US11564926B2 (en) 2023-01-31
KR102363776B1 (ko) 2022-02-15
KR20210083381A (ko) 2021-07-06
MY170520A (en) 2019-08-08
RU2018128393A3 (en:Method) 2019-04-16
TWI755628B (zh) 2022-02-21
US9968612B2 (en) 2018-05-15
EP4023641B1 (en) 2024-05-01
US20150203473A1 (en) 2015-07-23
IL288133B1 (en) 2024-08-01
MX2018014924A (es) 2020-09-02
EP3689853B1 (en) 2021-11-24
EP3689853A1 (en) 2020-08-05
EP2895466A1 (en) 2015-07-22
US20240122936A1 (en) 2024-04-18
US20180228807A1 (en) 2018-08-16
SG10202006058QA (en) 2020-08-28
WO2014043706A8 (en) 2017-10-19
IL320269A (en) 2025-06-01
NZ705827A (en) 2018-07-27
EP4023641A2 (en) 2022-07-06
TW201946917A (zh) 2019-12-16
MX395148B (es) 2025-03-24
JP6616688B2 (ja) 2019-12-04
TW202134217A (zh) 2021-09-16
US10894050B2 (en) 2021-01-19
JP2019048856A (ja) 2019-03-28
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