CA2974605C - Salt of a pyrimido[6,1-a]isoquinolin-4-one compound - Google Patents

Salt of a pyrimido[6,1-a]isoquinolin-4-one compound Download PDF

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Publication number
CA2974605C
CA2974605C CA2974605A CA2974605A CA2974605C CA 2974605 C CA2974605 C CA 2974605C CA 2974605 A CA2974605 A CA 2974605A CA 2974605 A CA2974605 A CA 2974605A CA 2974605 C CA2974605 C CA 2974605C
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Canada
Prior art keywords
rpl554
salt
acid
pharmaceutically acceptable
addition salt
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CA2974605A
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English (en)
French (fr)
Other versions
CA2974605A1 (en
Inventor
Peter Lionel Spargo
Edward James FRENCH
Julian Scott Northen
John Mykytiuk
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Verona Pharma Ltd
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Verona Pharma Ltd
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Publication of CA2974605A1 publication Critical patent/CA2974605A1/en
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    • 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
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/007Pulmonary tract; Aromatherapy
    • A61K9/0073Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0075Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • 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
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/007Pulmonary tract; Aromatherapy
    • A61K9/0073Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0078Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/08Solutions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/02Nasal agents, e.g. decongestants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/04Antipruritics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Otolaryngology (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Transplantation (AREA)
  • Dispersion Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicinal Preparation (AREA)
CA2974605A 2015-02-11 2016-02-10 Salt of a pyrimido[6,1-a]isoquinolin-4-one compound Active CA2974605C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1502260.1 2015-02-11
GB201502260A GB201502260D0 (en) 2015-02-11 2015-02-11 Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound
PCT/GB2016/050313 WO2016128742A1 (en) 2015-02-11 2016-02-10 Salt of a pyrimido[6,1-a]isoquinolin-4-one compound

Publications (2)

Publication Number Publication Date
CA2974605A1 CA2974605A1 (en) 2016-08-18
CA2974605C true CA2974605C (en) 2024-02-13

Family

ID=52781414

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2974605A Active CA2974605C (en) 2015-02-11 2016-02-10 Salt of a pyrimido[6,1-a]isoquinolin-4-one compound

Country Status (13)

Country Link
US (2) US10463665B2 (enExample)
EP (2) EP4461358A3 (enExample)
JP (2) JP7089366B2 (enExample)
CN (2) CN107406446B (enExample)
AU (2) AU2016217674B2 (enExample)
CA (1) CA2974605C (enExample)
ES (1) ES3018557T3 (enExample)
GB (1) GB201502260D0 (enExample)
IL (1) IL253595B (enExample)
MX (1) MX382019B (enExample)
PT (1) PT3256472T (enExample)
WO (1) WO2016128742A1 (enExample)
ZA (1) ZA201705112B (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2682105T3 (es) 2014-05-12 2018-09-18 Verona Pharma Plc Nuevo tratamiento
ES2670025T3 (es) 2014-09-15 2018-05-29 Verona Pharma Plc Formulación para inhalación líquida que comprende RPL554
GB201502260D0 (en) 2015-02-11 2015-04-01 Verona Pharma Plc Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound
GB201613054D0 (en) 2016-07-28 2016-09-14 Verona Pharma Plc New compound and process
GB2578093B (en) * 2018-10-09 2020-11-18 Verona Pharma Plc Liquid pharmaceutical composition comprising RPL554 and HFA-134A
GB201911517D0 (en) * 2019-08-12 2019-09-25 Verona Pharma Plc Pharmaceutical composition
CN114929700B (zh) * 2020-01-15 2024-11-22 正大天晴药业集团股份有限公司 三并环类pde3/pde4双重抑制剂化合物的药物组合物
CN115843330A (zh) * 2020-04-22 2023-03-24 辉瑞公司 冠状病毒疫苗
WO2023076205A1 (en) 2021-10-29 2023-05-04 Teva Pharmaceuticals International Gmbh Solid state forms of ensifentrine and process for preparation thereof
US20250059186A1 (en) * 2021-12-14 2025-02-20 Xizang Haisco Pharmaceutical Co., Ltd. Tricyclic Fused Heterocyclic PDE3/4 Dual Inhibitor and Use Thereof
GB202202297D0 (en) 2022-02-21 2022-04-06 Verona Pharma Plc Formulation production process
WO2024033625A1 (en) * 2022-08-08 2024-02-15 Verona Pharma Plc Ensifentrine (rpl-554) for increasing trough lung function
EP4378942A1 (en) 2022-12-02 2024-06-05 Sandoz AG Crystal form of a pde3/4 inhibitor
US12194045B1 (en) 2023-06-26 2025-01-14 Verona Pharma Plc Particulate composition
WO2025176871A1 (en) 2024-02-23 2025-08-28 Inke, S.A. Process for preparing pyrimido[6,1-a]isoquinoline-4-ones

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZW6284A1 (en) 1983-05-05 1985-10-30 Hoffmann La Roche Novel pyrimidone derivatives
DE3816995A1 (de) 1988-05-19 1989-11-23 Hoechst Ag Verwendung von pyrimido-(6,1-a)-isochinolin-4-on-derivaten und medizinische zubereitungen auf basis dieser verbindungen
PT1165558E (pt) 1999-03-31 2004-02-27 Vernalis Ltd Derivados de pirimido¬6,1-a|isoquinolina-4-ona
US20030235631A1 (en) * 2002-06-17 2003-12-25 Pfizer Inc. Combination treatment for depression and anxiety
ES2365926T3 (es) * 2004-09-08 2011-10-13 Nycomed Gmbh 3-oxa-10-aza-fenantrenos como inhibidores de pde4 o pde3/4.
CA2796280A1 (en) 2010-04-15 2011-10-20 The Royal Institution For The Advancement Of Learning / Mcgill Universit Y Topical treatments for pain
AU2011288497B2 (en) 2010-08-09 2016-01-21 Verona Pharma Plc Crystalline form of pyrimido[6,1-a]isoquinolin-4-one compound
EP2647627A1 (en) 2012-04-02 2013-10-09 Almirall, S.A. Salts of 5-[(1r)-2-({2-[4-(2,2-difluoro-2-phenylethoxy)phenyl] ethyl}amino)-1-hydroxyethyl]-8-hydroxyquinolin-2(1h)-one.
AU2014229739B2 (en) 2013-03-15 2018-07-26 Verona Pharma Plc Drug combination
ES2682105T3 (es) 2014-05-12 2018-09-18 Verona Pharma Plc Nuevo tratamiento
ES2670025T3 (es) 2014-09-15 2018-05-29 Verona Pharma Plc Formulación para inhalación líquida que comprende RPL554
GB201502260D0 (en) 2015-02-11 2015-04-01 Verona Pharma Plc Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound
GB201613054D0 (en) 2016-07-28 2016-09-14 Verona Pharma Plc New compound and process
GB2578093B (en) 2018-10-09 2020-11-18 Verona Pharma Plc Liquid pharmaceutical composition comprising RPL554 and HFA-134A

Also Published As

Publication number Publication date
EP3256472B1 (en) 2025-03-19
CN107406446B (zh) 2021-12-28
CN113105453A (zh) 2021-07-13
AU2016217674B2 (en) 2020-04-30
JP7089366B2 (ja) 2022-06-22
IL253595A0 (en) 2017-09-28
AU2020205281B2 (en) 2021-07-15
EP4461358A2 (en) 2024-11-13
EP3256472A1 (en) 2017-12-20
US10463665B2 (en) 2019-11-05
IL253595B (en) 2021-04-29
CA2974605A1 (en) 2016-08-18
MX2017010195A (es) 2017-11-17
ES3018557T3 (es) 2025-05-16
US20180021337A1 (en) 2018-01-25
JP7110303B2 (ja) 2022-08-01
CN107406446A (zh) 2017-11-28
NZ733926A (en) 2023-10-27
EP4461358A3 (en) 2025-01-15
JP2021046405A (ja) 2021-03-25
WO2016128742A1 (en) 2016-08-18
AU2020205281A1 (en) 2020-08-06
MX382019B (es) 2025-03-13
US20200016158A1 (en) 2020-01-16
PT3256472T (pt) 2025-04-11
US11491155B2 (en) 2022-11-08
GB201502260D0 (en) 2015-04-01
ZA201705112B (en) 2022-05-25
AU2016217674A1 (en) 2017-08-10
JP2018505192A (ja) 2018-02-22

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