WO2024252327A8 - Solid forms of n-(methoxycarbonyl)-3-methyl-l-valyl-(4r)- n-{(1s)-1-cyano-2-[(3s)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-l-prolinamide and solvates thereof - Google Patents

Solid forms of n-(methoxycarbonyl)-3-methyl-l-valyl-(4r)- n-{(1s)-1-cyano-2-[(3s)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-l-prolinamide and solvates thereof Download PDF

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Publication number
WO2024252327A8
WO2024252327A8 PCT/IB2024/055548 IB2024055548W WO2024252327A8 WO 2024252327 A8 WO2024252327 A8 WO 2024252327A8 IB 2024055548 W IB2024055548 W IB 2024055548W WO 2024252327 A8 WO2024252327 A8 WO 2024252327A8
Authority
WO
WIPO (PCT)
Prior art keywords
solid forms
ethyl
prolinamide
oxopyrrolidin
valyl
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.)
Ceased
Application number
PCT/IB2024/055548
Other languages
French (fr)
Other versions
WO2024252327A1 (en
Inventor
Kapildev Kashmirilal ARORA
Maria GONZALEZ ESGUEVILLAS
Samir Kulkarni
Aifang Li
Paul Anthony MEENAN
Nandini PATEL
Jeanene Elizabeth Tickner
Xiaojing Yang
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.)
Pfizer Inc
Original Assignee
Pfizer 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 Pfizer Inc filed Critical Pfizer Inc
Priority to EP24733330.5A priority Critical patent/EP4724423A1/en
Priority to AU2024285970A priority patent/AU2024285970A1/en
Priority to MX2025014633A priority patent/MX2025014633A/en
Priority to KR1020267000360A priority patent/KR20260021033A/en
Priority to CN202480038170.0A priority patent/CN121311467A/en
Publication of WO2024252327A1 publication Critical patent/WO2024252327A1/en
Publication of WO2024252327A8 publication Critical patent/WO2024252327A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/401—Proline; Derivatives thereof, e.g. captopril
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The present disclosure is directed to solid forms of N-(Methoxycarbonyl)-3-methyl-L- valyl-(4R)-N-{(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-L- prolinamide, I, such as anhydrous forms thereof, an amorphous form thereof, a cyclopentyl methyl ether solvate thereof, an isopropyl acetate solvate thereof, and an ethyl acetate solvate thereof Formula (I) and to pharmaceutical compositions comprising the solid forms and methods of treatment employing the solid forms.
PCT/IB2024/055548 2023-06-09 2024-06-06 Solid forms of n-(methoxycarbonyl)-3-methyl-l-valyl-(4 r)- n-{(1 s)-1-cyano-2-[(3 s)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-l-prolinamide and solvates thereof Ceased WO2024252327A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP24733330.5A EP4724423A1 (en) 2023-06-09 2024-06-06 Solid forms of n-(methoxycarbonyl)-3-methyl-l-valyl-(4 r)- n-{(1 s)-1-cyano-2-[(3 s)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-l-prolinamide and solvates thereof
AU2024285970A AU2024285970A1 (en) 2023-06-09 2024-06-06 Solid forms of n-(methoxycarbonyl)-3-methyl-l-valyl-(4r)- n-{(1s)-1-cyano-2-[(3s)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-l-prolinamide and solvates thereof
MX2025014633A MX2025014633A (en) 2023-06-09 2024-06-06 SOLID FORMS OF N-(METHOXYCARBONYL)-3-METHYL-L-VALLYL-(4R)-N-{(1S)-1-CYANO-2-[(3S)-2-OXOPYRROLIDIN-3-YL]ETHYL}-4-(TRIFLUOROMETHYL)-L-PROLINAMIDE AND SOLVATES THEREOF
KR1020267000360A KR20260021033A (en) 2023-06-09 2024-06-06 Solid form of N-(methoxycarbonyl)-3-methyl-L-valyl-(4R)-N-{(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-L-prolinamide and solvates thereof
CN202480038170.0A CN121311467A (en) 2023-06-09 2024-06-06 N-(methoxycarbonyl)-3-methyl-L-valinel-(4R)-N-{(1S)-1-cyano-2-[(3S)-2-oxopyrrolid-3-yl]ethyl}-4-(trifluoromethyl)-L-prolylamide and its solvates in solid form

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US202363507347P 2023-06-09 2023-06-09
US63/507,347 2023-06-09
US202463647157P 2024-05-14 2024-05-14
US63/647,157 2024-05-14

Publications (2)

Publication Number Publication Date
WO2024252327A1 WO2024252327A1 (en) 2024-12-12
WO2024252327A8 true WO2024252327A8 (en) 2025-06-26

Family

ID=91581111

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2024/055548 Ceased WO2024252327A1 (en) 2023-06-09 2024-06-06 Solid forms of n-(methoxycarbonyl)-3-methyl-l-valyl-(4 r)- n-{(1 s)-1-cyano-2-[(3 s)-2-oxopyrrolidin-3-yl]ethyl}-4-(trifluoromethyl)-l-prolinamide and solvates thereof

Country Status (6)

Country Link
EP (1) EP4724423A1 (en)
KR (1) KR20260021033A (en)
CN (1) CN121311467A (en)
AU (1) AU2024285970A1 (en)
MX (1) MX2025014633A (en)
WO (1) WO2024252327A1 (en)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3773919A (en) 1969-10-23 1973-11-20 Du Pont Polylactide-drug mixtures
US4485045A (en) 1981-07-06 1984-11-27 Research Corporation Synthetic phosphatidyl cholines useful in forming liposomes
US4544545A (en) 1983-06-20 1985-10-01 Trustees University Of Massachusetts Liposomes containing modified cholesterol for organ targeting
US5013556A (en) 1989-10-20 1991-05-07 Liposome Technology, Inc. Liposomes with enhanced circulation time
JP6419313B2 (en) 2014-05-09 2018-11-07 キネタ・インコーポレイテッドＫｉｎｅｔａ， Ｉｎｃ． Antiviral compounds, pharmaceutical compositions and methods of use thereof
CN112617981A (en) 2019-09-24 2021-04-09 广州迪克医疗器械有限公司 Puncture rods and punctures
US11351149B2 (en) * 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds

Also Published As

Publication number Publication date
CN121311467A (en) 2026-01-09
MX2025014633A (en) 2026-02-03
WO2024252327A1 (en) 2024-12-12
TW202513557A (en) 2025-04-01
EP4724423A1 (en) 2026-04-15
AU2024285970A1 (en) 2025-12-11
KR20260021033A (en) 2026-02-12

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