CA3108800A1 - Salts and crystal forms of omecamtiv mecarbil - Google Patents

Salts and crystal forms of omecamtiv mecarbil Download PDF

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Publication number
CA3108800A1
CA3108800A1 CA3108800A CA3108800A CA3108800A1 CA 3108800 A1 CA3108800 A1 CA 3108800A1 CA 3108800 A CA3108800 A CA 3108800A CA 3108800 A CA3108800 A CA 3108800A CA 3108800 A1 CA3108800 A1 CA 3108800A1
Authority
CA
Canada
Prior art keywords
omecamtiv mecarbil
peaks
radiation
xrpd
crystalline salt
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.)
Pending
Application number
CA3108800A
Other languages
English (en)
French (fr)
Inventor
Henry Morrison
Sheng CUI
Kyle QUASDORF
Evelyn YANEZ
Bin Peter Quan
Ron C. Kelly
Sebastien Caille
Lingyun Xiao
David Pearson
Jaclyn RAEBURN
Ailsa GOLIGHTLY
Bradley Morgan
Matthew Peterson
Alex Eberlin
Alexander OBLEZOV
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.)
Amgen Inc
Cytokinetics Inc
Original Assignee
Amgen Inc
Cytokinetics Inc
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 Amgen Inc, Cytokinetics Inc filed Critical Amgen Inc
Publication of CA3108800A1 publication Critical patent/CA3108800A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/08—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
    • C07C309/34—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by two rings
    • C07C309/35—Naphthalene sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/06—Oxalic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/08—Malonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/145—Maleic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid
    • 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
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
    • C07C65/10—Salicylic acid
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Medicinal Preparation (AREA)
CA3108800A 2018-08-17 2019-08-16 Salts and crystal forms of omecamtiv mecarbil Pending CA3108800A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862765090P 2018-08-17 2018-08-17
US62/765,090 2018-08-17
PCT/US2019/046726 WO2020037164A1 (en) 2018-08-17 2019-08-16 Salts and crystal forms of omecamtiv mecarbil

Publications (1)

Publication Number Publication Date
CA3108800A1 true CA3108800A1 (en) 2020-02-20

Family

ID=67809688

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3108800A Pending CA3108800A1 (en) 2018-08-17 2019-08-16 Salts and crystal forms of omecamtiv mecarbil

Country Status (8)

Country Link
US (3) US11465969B2 (enExample)
EP (1) EP3837009A1 (enExample)
JP (3) JP2021534138A (enExample)
AU (2) AU2019321573B2 (enExample)
CA (1) CA3108800A1 (enExample)
MA (1) MA53226A (enExample)
MX (2) MX2021001792A (enExample)
WO (1) WO2020037164A1 (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0512193B8 (pt) 2004-06-17 2021-05-25 Cytokinetics Inc composto ou sal farmaceuticamente aceitável, composição farmacêutica, e, uso do composto ou sal
AU2014240049C1 (en) 2013-03-14 2019-03-07 Amgen Inc. Heterocyclic compounds and their uses
US11040956B2 (en) 2017-06-30 2021-06-22 Amgen Inc. Synthesis of omecamtiv mecarbil
LT3645002T (lt) 2017-06-30 2025-02-10 Amgen Inc. Širdies nepakankamumo gydymo būdas širdies sarkomerų aktyvatoriais
UY37879A (es) 2017-09-13 2019-03-29 Amgen Inc Compuestos de bisamida que activan el sarcómero y sus usos
HUE052049T2 (hu) 2018-07-09 2021-04-28 Fis Fabbrica Italiana Sintetici Spa Kristályos 2-fluor-3-nitrotoluol és eljárás annak elõállítására
JP2021534138A (ja) * 2018-08-17 2021-12-09 アムジエン・インコーポレーテツド オメカムチブメカルビルの塩及び結晶形態
WO2020131574A1 (en) 2018-12-18 2020-06-25 Amgen Inc. Method of reducing aromatic nitro compounds
WO2021053175A1 (en) * 2019-09-19 2021-03-25 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
WO2021053189A1 (en) * 2019-09-19 2021-03-25 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
US20220402874A1 (en) * 2019-10-09 2022-12-22 Dr. Reddy's Laboratories Limited Solid forms of omecamtiv mecarbil dihydrochloride and processes thereof
TW202233189A (zh) 2020-11-12 2022-09-01 美商安進公司 藉由投與奧美卡替莫卡必爾治療心臟衰竭之方法
WO2022177927A1 (en) 2021-02-16 2022-08-25 Assia Chemical Industries Ltd Unhydrous crystalline form of omecamtiv mecarbil dihydrobromide salt
TW202300479A (zh) 2021-03-10 2023-01-01 美商安進公司 奧美卡替莫卡必爾之合成
US11986474B1 (en) 2023-06-27 2024-05-21 Cytokinetics, Incorporated Methods for treating heart failure by administering cardiac sarcomere activators

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4522811A (en) 1982-07-08 1985-06-11 Syntex (U.S.A.) Inc. Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides
BRPI0512193B8 (pt) 2004-06-17 2021-05-25 Cytokinetics Inc composto ou sal farmaceuticamente aceitável, composição farmacêutica, e, uso do composto ou sal
ES2419007T3 (es) 2005-12-15 2013-08-19 Cytokinetics, Inc. Ciertas entidades químicas, composiciones y procedimientos
US20090192168A1 (en) 2008-01-04 2009-07-30 Alex Muci Compounds, Compositions and Methods
AU2014240104B2 (en) 2013-03-14 2018-11-08 Amgen Inc. Heterocyclic compounds and their uses
AU2014240049C1 (en) 2013-03-14 2019-03-07 Amgen Inc. Heterocyclic compounds and their uses
CA2975260C (en) 2015-01-29 2024-05-21 Signal Pharmaceuticals Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
US10543215B2 (en) 2015-06-26 2020-01-28 Amgen Inc. Combination therapy of cardiac myosin activator and sinus node if current inhibitor
LT3645002T (lt) 2017-06-30 2025-02-10 Amgen Inc. Širdies nepakankamumo gydymo būdas širdies sarkomerų aktyvatoriais
US11040956B2 (en) 2017-06-30 2021-06-22 Amgen Inc. Synthesis of omecamtiv mecarbil
HUE052049T2 (hu) 2018-07-09 2021-04-28 Fis Fabbrica Italiana Sintetici Spa Kristályos 2-fluor-3-nitrotoluol és eljárás annak elõállítására
US11608318B2 (en) 2018-07-12 2023-03-21 Assia Chemical Industries Ltd. Solid state forms of Omecamtiv mecarbil and Omecamtiv mecarbil diHCl
JP2021534138A (ja) * 2018-08-17 2021-12-09 アムジエン・インコーポレーテツド オメカムチブメカルビルの塩及び結晶形態
WO2020131574A1 (en) 2018-12-18 2020-06-25 Amgen Inc. Method of reducing aromatic nitro compounds
WO2021053189A1 (en) 2019-09-19 2021-03-25 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
WO2021053175A1 (en) 2019-09-19 2021-03-25 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
US20220402874A1 (en) 2019-10-09 2022-12-22 Dr. Reddy's Laboratories Limited Solid forms of omecamtiv mecarbil dihydrochloride and processes thereof
EP4041710A1 (en) 2019-10-09 2022-08-17 Dr. Reddy's Laboratories Limited Alternate processes for the preparation of omecamtiv mecarbil
CN114929671B (zh) 2020-01-03 2024-04-16 苏州科睿思制药有限公司 化合物i二盐酸盐的共晶及其制备方法和用途
CA3168513A1 (en) 2020-02-10 2021-08-19 Amgen Inc. Omecamtiv mecarbil tablet
TW202233189A (zh) 2020-11-12 2022-09-01 美商安進公司 藉由投與奧美卡替莫卡必爾治療心臟衰竭之方法
TW202300479A (zh) 2021-03-10 2023-01-01 美商安進公司 奧美卡替莫卡必爾之合成
US11986474B1 (en) 2023-06-27 2024-05-21 Cytokinetics, Incorporated Methods for treating heart failure by administering cardiac sarcomere activators

Also Published As

Publication number Publication date
MA53226A (fr) 2021-11-24
JP2024123028A (ja) 2024-09-10
US20230108971A1 (en) 2023-04-06
EP3837009A1 (en) 2021-06-23
AU2019321573B2 (en) 2025-05-29
MX2023013372A (es) 2023-11-27
US11926592B2 (en) 2024-03-12
US12612366B2 (en) 2026-04-28
JP2025108571A (ja) 2025-07-23
AU2025204014A1 (en) 2025-06-19
JP2021534138A (ja) 2021-12-09
US11465969B2 (en) 2022-10-11
WO2020037164A1 (en) 2020-02-20
US20240199550A1 (en) 2024-06-20
AU2019321573A1 (en) 2021-03-04
US20210221771A1 (en) 2021-07-22
MX2021001792A (es) 2021-05-27

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