WO2016038542A3 - Solid forms of sofosbuvir - Google Patents

Solid forms of sofosbuvir Download PDF

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Publication number
WO2016038542A3
WO2016038542A3 PCT/IB2015/056893 IB2015056893W WO2016038542A3 WO 2016038542 A3 WO2016038542 A3 WO 2016038542A3 IB 2015056893 W IB2015056893 W IB 2015056893W WO 2016038542 A3 WO2016038542 A3 WO 2016038542A3
Authority
WO
WIPO (PCT)
Prior art keywords
sofosbuvir
solid forms
present disclosure
solid dispersion
amorphous solid
Prior art date
Application number
PCT/IB2015/056893
Other languages
French (fr)
Other versions
WO2016038542A2 (en
Inventor
Ramakoteswara Rao Jetti
Asharani GORANTLA
Satish BEERAVELLY
Neelima Bhagavatula
Amit Singh
Sureshbabu JAYACHANDRA
Vipin Kumar Kaushik
Vijaya Krishana RAVI
Srinivas VAKITI
Potla Venkata Srinivas RAO
Original Assignee
Mylan Laboratories Limited
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 Mylan Laboratories Limited filed Critical Mylan Laboratories Limited
Publication of WO2016038542A2 publication Critical patent/WO2016038542A2/en
Publication of WO2016038542A3 publication Critical patent/WO2016038542A3/en

Links

Classifications

    • 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
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Abstract

The present disclosure provides crystalline sofosbuvir form-M1 and amorphous solid dispersion of sofosbuvir. The present disclosure also provides a process for the preparation of the amorphous form of sofosbuvir, the crystalline form of sofosbuvir, and amorphous solid dispersion of sofosbuvir and one or more pharmaceutically acceptable carriers.
PCT/IB2015/056893 2014-09-10 2015-09-09 Polymorphic forms of sofosbuvir WO2016038542A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN4436/CHE/2014 2014-09-10
IN4436CH2014 2014-09-10

Publications (2)

Publication Number Publication Date
WO2016038542A2 WO2016038542A2 (en) 2016-03-17
WO2016038542A3 true WO2016038542A3 (en) 2016-05-12

Family

ID=54292841

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2015/056893 WO2016038542A2 (en) 2014-09-10 2015-09-09 Polymorphic forms of sofosbuvir

Country Status (1)

Country Link
WO (1) WO2016038542A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3524234B1 (en) 2014-06-13 2020-12-09 Ratiopharm GmbH Solid state forms of sofosbuvir
CA2999215A1 (en) * 2015-10-07 2017-04-13 Sandoz Ag Solid pharmaceutical composition comprising amorphous sofosbuvir
EP3430023A1 (en) 2016-03-17 2019-01-23 Mylan Laboratories, Limited Polymorphic forms of sofosbuvir
CZ2016257A3 (en) * 2016-05-05 2017-11-15 Zentiva, K.S. The amorphous form of sofosbuvir, the method of its preparation and its stabilization
WO2018029262A1 (en) * 2016-08-12 2018-02-15 Sandoz Ag Solid pharmaceutical composition comprising amorphous sofosbuvir
RU2656228C9 (en) * 2017-06-13 2019-04-16 Олег Ростиславович Михайлов WEAKLY CRYSTALLISED β-MODIFICATION OF (S)-ISOPROPYL 2-((S)-(((2R,3R,4R,5R)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-(2H)-YL)-4-FLUORO-3-HYDROXY-4-METHYLTETRAHYDROFURAN-2-YL)METHOXY)-(PHENOXY)PHOSPHORYLAMINO)PROPANOATE, METHOD FOR PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITION BASED THEREON
EP3661944A1 (en) 2017-08-03 2020-06-10 Sandoz AG Sofosbuvir hydrate
CN109467577A (en) * 2018-12-06 2019-03-15 南通常佑药业科技有限公司 A kind of preparation method of Suo Feibuwei crystal form and amorphous products
WO2021203409A1 (en) * 2020-04-10 2021-10-14 南京正大天晴制药有限公司 Novel non-hygroscopic low-variability crystalline form for treatment of hepatitis c

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013101550A1 (en) * 2011-12-29 2013-07-04 Abbvie Inc. Solid compositions comprising an hcv inhibitor
US20140212491A1 (en) * 2013-01-31 2014-07-31 Gilead Pharmasset Llc Combination formulation of two antiviral compounds
WO2015150561A2 (en) * 2014-04-03 2015-10-08 Sandoz Ag Solid composition comprising amorphous sofosbuvir

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7964580B2 (en) 2007-03-30 2011-06-21 Pharmasset, Inc. Nucleoside phosphoramidate prodrugs
TWI576352B (en) 2009-05-20 2017-04-01 基利法瑪席特有限責任公司 Nucleoside phosphoramidates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013101550A1 (en) * 2011-12-29 2013-07-04 Abbvie Inc. Solid compositions comprising an hcv inhibitor
US20140212491A1 (en) * 2013-01-31 2014-07-31 Gilead Pharmasset Llc Combination formulation of two antiviral compounds
WO2015150561A2 (en) * 2014-04-03 2015-10-08 Sandoz Ag Solid composition comprising amorphous sofosbuvir

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VO CHAU LE-NGOC ET AL: "Current trends and future perspectives of solid dispersions containing poorly water-soluble drugs", EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS, vol. 85, no. 3, 18 September 2013 (2013-09-18), pages 799 - 813, XP028791016, ISSN: 0939-6411, DOI: 10.1016/J.EJPB.2013.09.007 *

Also Published As

Publication number Publication date
WO2016038542A2 (en) 2016-03-17

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