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

Salts and crystal forms of omecamtiv mecarbil Download PDF

Info

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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/02Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/02Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/08Sulfonic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/28Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/33Sulfonic 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
    • C07C309/34Sulfonic 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
    • C07C309/35Naphthalene sulfonic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02Dicarboxylic acids
    • C07C55/06Oxalic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02Dicarboxylic acids
    • C07C55/08Malonic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13Dicarboxylic acids
    • C07C57/145Maleic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13Dicarboxylic acids
    • C07C57/15Fumaric acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235Saturated compounds containing more than one carboxyl group
    • C07C59/245Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255Tartaric acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00Compounds 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
    • C07C65/01Compounds 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
    • C07C65/03Compounds 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
    • C07C65/05Compounds 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
    • C07C65/10Salicylic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline 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 (2) US11465969B2 (https=)
EP (1) EP3837009A1 (https=)
JP (3) JP2021534138A (https=)
AU (2) AU2019321573B2 (https=)
CA (1) CA3108800A1 (https=)
MA (1) MA53226A (https=)
MX (2) MX2021001792A (https=)
WO (1) WO2020037164A1 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5080970B2 (ja) 2004-06-17 2012-11-21 サイトキネティクス・インコーポレーテッド 心疾患を治療するための置換尿素誘導体
DK2970123T4 (da) 2013-03-14 2026-01-26 Amgen Inc Krystallinsk dihydrochloridhydratsalt af omecamtiv mecarbil og fremgangsmåde til fremstilling heraf
SMT202100472T1 (it) 2017-06-30 2021-09-14 Amgen Inc Sintesi di omecamtiv mecarbil
EP4512470A3 (en) 2017-06-30 2025-04-23 Amgen Inc. Methods of treating heart failure with cardiac sarcomere activators
AU2018332887B2 (en) 2017-09-13 2022-12-08 Amgen Inc. Bisamide sarcomere activating compounds and uses thereof
EP3594199B1 (en) 2018-07-09 2020-07-01 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Crystalline 2-fluoro-3-nitrotoluene and process for the preparation thereof
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
US20220348543A1 (en) * 2019-09-19 2022-11-03 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
EP4031541A1 (en) * 2019-09-19 2022-07-27 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
US12194039B2 (en) 2020-11-12 2025-01-14 Amgen Inc Methods of treating heart failure by administering omecamtiv mecarbil
WO2022177927A1 (en) 2021-02-16 2022-08-25 Assia Chemical Industries Ltd Unhydrous crystalline form of omecamtiv mecarbil dihydrobromide salt
JP7843295B2 (ja) 2021-03-10 2026-04-09 アムジェン インコーポレイテッド オメカムチブメカルビルの合成
US11986474B1 (en) 2023-06-27 2024-05-21 Cytokinetics, Incorporated Methods for treating heart failure by administering cardiac sarcomere activators

Family Cites Families (22)

* 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
JP5080970B2 (ja) 2004-06-17 2012-11-21 サイトキネティクス・インコーポレーテッド 心疾患を治療するための置換尿素誘導体
TW200808321A (en) 2005-12-15 2008-02-16 Cytokinetics Inc Certain chemical entities, compositions and methods
US20090192168A1 (en) * 2008-01-04 2009-07-30 Alex Muci Compounds, Compositions and Methods
CA2902424A1 (en) 2013-03-14 2014-09-25 Amgen Inc. Heterocyclic compounds and their uses
DK2970123T4 (da) 2013-03-14 2026-01-26 Amgen Inc Krystallinsk dihydrochloridhydratsalt af omecamtiv mecarbil og fremgangsmåde til fremstilling heraf
WO2016123291A1 (en) 2015-01-29 2016-08-04 Signal Pharmaceuticals, Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
MX379899B (es) 2015-06-26 2025-03-11 Cytokinetics Inc Terapia de combinacion de activador de miosina cardiaca e inhibidor de corriente if del nodo sinusal
EP4512470A3 (en) 2017-06-30 2025-04-23 Amgen Inc. Methods of treating heart failure with cardiac sarcomere activators
SMT202100472T1 (it) 2017-06-30 2021-09-14 Amgen Inc Sintesi di omecamtiv mecarbil
EP3594199B1 (en) 2018-07-09 2020-07-01 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Crystalline 2-fluoro-3-nitrotoluene and process for the preparation thereof
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
EP4031541A1 (en) 2019-09-19 2022-07-27 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
US20220348543A1 (en) 2019-09-19 2022-11-03 Synthon B.V. Salts of omecamtiv mecarbil and solid forms thereof
WO2021070124A1 (en) 2019-10-09 2021-04-15 Dr. Reddy’S Laboratories Limited Alternate processes for the preparation of omecamtiv mecarbil
US20220402874A1 (en) 2019-10-09 2022-12-22 Dr. Reddy's Laboratories Limited Solid forms of omecamtiv mecarbil dihydrochloride and processes thereof
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
CN115279349A (zh) 2020-02-10 2022-11-01 安进股份有限公司 奥美卡替莫卡必尔片剂
US12194039B2 (en) 2020-11-12 2025-01-14 Amgen Inc Methods of treating heart failure by administering omecamtiv mecarbil
JP7843295B2 (ja) 2021-03-10 2026-04-09 アムジェン インコーポレイテッド オメカムチブメカルビルの合成

Also Published As

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

Similar Documents

Publication Publication Date Title
US11926592B2 (en) Salts and crystal forms of omecamtiv mecarbil
US12275704B2 (en) Heterocyclic compounds and their uses
US10590089B2 (en) Formulations of 2-(tert-butylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
TW201514165A (zh) D-葡萄糖醇,1-脫氧-1-(甲胺基)-,-1-(6-胺基-3,5-二氟吡啶-2-基)-8-氯-6-氟-1,4-二氫-7-(3-羥基氮雜環丁烷-1-基)-4-側氧基-3-喹啉羧酸的結晶形態與其製備程序
TWI857027B (zh) 心肌肌鈣蛋白活化劑之多晶型物
US12612366B2 (en) Salts and crystal forms of omecamtiv mecarbil
US20230040902A1 (en) Pharmaceutical Formulation Comprising Cibenzoline or Salt Thereof
WO2024149834A1 (en) Polymorphs of the hydrobromide salt of linaprazan glurate
WO2016155631A1 (zh) 托吡司他的新晶型及其制备方法
CA3210612C (en) Formulations of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20220908

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 5TH ANNIV.) - STANDARD

Year of fee payment: 5

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20240729

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20240729

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 6TH ANNIV.) - STANDARD

Year of fee payment: 6

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250702

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250702

D15 Examination report completed

Free format text: ST27 STATUS EVENT CODE: A-2-2-D10-D15-D126 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: EXAMINER'S REPORT

Effective date: 20251024

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT RECEIVED - RESPONSE TO EXAMINER'S REQUISITION

Effective date: 20260205

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT DETERMINED COMPLIANT

Effective date: 20260211

P13 Application amended

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P13-X000 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: APPLICATION AMENDED

Effective date: 20260211

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-2-2-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20260211