AR087344A1 - Formas polimorficas del acido 5-(3,3-dimetil-but-1-inil)-3-[(trans-4-hidroxi-ciclohexil)-(trans-4-metil-ciclohexancarbonil)-amino]-tiofen-2-carboxilico y su uso en el tratamiento de la hepatitis c - Google Patents

Formas polimorficas del acido 5-(3,3-dimetil-but-1-inil)-3-[(trans-4-hidroxi-ciclohexil)-(trans-4-metil-ciclohexancarbonil)-amino]-tiofen-2-carboxilico y su uso en el tratamiento de la hepatitis c

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Publication number
AR087344A1
AR087344A1 ARP120102726A ARP120102726A AR087344A1 AR 087344 A1 AR087344 A1 AR 087344A1 AR P120102726 A ARP120102726 A AR P120102726A AR P120102726 A ARP120102726 A AR P120102726A AR 087344 A1 AR087344 A1 AR 087344A1
Authority
AR
Argentina
Prior art keywords
compound
polymorphic form
formula
diffraction pattern
ray powder
Prior art date
Application number
ARP120102726A
Other languages
English (en)
Inventor
Hoa Q Luong
Kan Hu
Brian Nian-Luisi
David Willcox
Stefanie Roeper
Original Assignee
Vertex Pharma
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 Vertex Pharma filed Critical Vertex Pharma
Publication of AR087344A1 publication Critical patent/AR087344A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40—Cyclodextrins; Derivatives thereof
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Dermatology (AREA)
  • Virology (AREA)
  • Endocrinology (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un método para preparar la Forma polimórfica M del compuesto de fórmula (1) incluye agitar una mezcla del compuesto de fórmula (1) y un sistema de solvente que incluye isopropanol, etil acetato, n-butil acetato, metil acetato, acetona, 2-butanona (metiletilcetona (MEK)), o heptano, o una combinación de los mismos a una temperatura comprendida entre 10ºC y 47ºC para formar la Forma M del compuesto de fórmula (1). Un método para preparar la Forma polimórfica H del compuesto de fórmula (1) incluye agitar una solución del compuesto de fórmula (1) a una temperatura comprendida entre 48ºC y 70ºC para formar la Forma H del compuesto de fórmula (1). Un método para preparar la Forma P del compuesto de fórmula (1) incluye agitar una mezcla del compuesto de fórmula (1) y un sistema de solvente que incluye un solvente seleccionado entre el grupo formado por diclorometano y tetrahidrofurano (THF), y una mezcla de los mismos a temperatura ambiente para formar la Forma P del compuesto de fórmula (1). Un método para preparar la Forma X del compuesto de fórmula (1) incluye remover el solvato G de etil acetato del compuesto de fórmula (1). Un método para preparar la Forma ZA del compuesto de fórmula (1) incluye remover el n-butil acetato del solvato A de n-butil acetato del compuesto de fórmula (1).Reivindicación 1: Una forma polimórfica del compuesto (1) representado por la fórmula estructural (1), en donde la forma polimórfica es la forma polimórfica M, forma polimórfica H, forma polimórfica P, forma polimórfica X o forma polimórfica ZA. Reivindicación 4: La forma polimórfica de acuerdo con la reivindicación 2, en donde la forma polimórfica M se caracteriza por tener un patrón de difracción de polvos por rayos X con picos característicos expresados en 2-q ± 0,2 en las siguientes posiciones: 19,6, 16,6, 18,1, 9,0, 22,2 y 11,4, en donde el patrón de difracción de polvos por rayos X se obtiene a temperatura ambiente usando radiación CuKa. Reivindicación 11: La forma polimórfica de acuerdo con la reivindicación 9, en donde la forma polimórfica H se caracteriza por tener un patrón de difracción de polvos por rayos X con picos característicos expresados en 2-q ± 0,2 en las siguientes posiciones: 6,6, 18,7, 8,5, 17,3, 15,8 y 19,4, en donde el patrón de difracción de polvos por rayos X se obtiene a temperatura ambiente usando radiación CuKa. Reivindicación 18: La forma polimórfica de acuerdo con la reivindicación 16, en donde la forma polimórfica P se caracteriza por tener un patrón de difracción de polvos por rayos X con picos característicos expresados en 2-q ± 0,2 en las siguientes posiciones: 7,0, 15,8, 9,8, 19,3, 8,5 y 21,9, en donde el patrón de difracción de polvos por rayos X se obtiene a temperatura ambiente usando radiación CuKa. Reivindicación 25: La forma polimórfica de acuerdo con la reivindicación 23, en donde la forma polimórfica X se caracteriza por tener un patrón de difracción de polvos por rayos X con picos característicos expresados en 2-q ± 0,2 en las siguientes posiciones: 7,5, 12,1, 13,0, 13,8, 16,2 y 19,7 en donde el patrón de difracción de polvos por rayos X se obtiene a temperatura ambiente usando radiación CuKa. Reivindicación 29: La forma polimórfica de acuerdo con la reivindicación 27, en donde la forma polimórfica ZA se caracteriza por tener un patrón de difracción de polvos por rayos X con picos característicos expresados en 2-q ± 0,2 en las siguientes posiciones: 5,2, 10,2, 16,5, 18,6, 19,8 y 20,3, en donde el patrón de difracción de polvos por rayos X se obtiene a temperatura ambiente usando radiación CuKa. Reivindicación 31: Una forma amorfa del compuesto (1) representado por la fórmula estructural (1).
ARP120102726A 2011-07-26 2012-07-26 Formas polimorficas del acido 5-(3,3-dimetil-but-1-inil)-3-[(trans-4-hidroxi-ciclohexil)-(trans-4-metil-ciclohexancarbonil)-amino]-tiofen-2-carboxilico y su uso en el tratamiento de la hepatitis c AR087344A1 (es)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201161511643P 2011-07-26 2011-07-26
US201161511647P 2011-07-26 2011-07-26
US201161511648P 2011-07-26 2011-07-26
US201161511644P 2011-07-26 2011-07-26
US201161512079P 2011-07-27 2011-07-27
US201161545751P 2011-10-11 2011-10-11
US201261623144P 2012-04-12 2012-04-12

Publications (1)

Publication Number Publication Date
AR087344A1 true AR087344A1 (es) 2014-03-19

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Family Applications (3)

Application Number Title Priority Date Filing Date
ARP120102726A AR087344A1 (es) 2011-07-26 2012-07-26 Formas polimorficas del acido 5-(3,3-dimetil-but-1-inil)-3-[(trans-4-hidroxi-ciclohexil)-(trans-4-metil-ciclohexancarbonil)-amino]-tiofen-2-carboxilico y su uso en el tratamiento de la hepatitis c
ARP120102727A AR087345A1 (es) 2011-07-26 2012-07-26 Metodos para la preparacion de compuestos de tiofeno
ARP120102728A AR087346A1 (es) 2011-07-26 2012-07-26 Formulaciones de compuestos de tiofeno

Family Applications After (2)

Application Number Title Priority Date Filing Date
ARP120102727A AR087345A1 (es) 2011-07-26 2012-07-26 Metodos para la preparacion de compuestos de tiofeno
ARP120102728A AR087346A1 (es) 2011-07-26 2012-07-26 Formulaciones de compuestos de tiofeno

Country Status (6)

Country Link
US (3) US20140235703A1 (es)
EP (1) EP2736893A1 (es)
AR (3) AR087344A1 (es)
AU (1) AU2012286853A1 (es)
TW (2) TW201313697A (es)
WO (4) WO2013016501A1 (es)

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AU2012286853A1 (en) 2013-05-02
US20140235703A1 (en) 2014-08-21
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US20140235705A1 (en) 2014-08-21
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US20140235704A1 (en) 2014-08-21
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