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WO2008051244A2 - Dérivés de l'acide anthranilique utilisables pour le traitement d'une infection par le virus de l'hépatite c - Google Patents

Dérivés de l'acide anthranilique utilisables pour le traitement d'une infection par le virus de l'hépatite c Download PDF

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Publication number
WO2008051244A2
WO2008051244A2 PCT/US2006/045950 US2006045950W WO2008051244A2 WO 2008051244 A2 WO2008051244 A2 WO 2008051244A2 US 2006045950 W US2006045950 W US 2006045950W WO 2008051244 A2 WO2008051244 A2 WO 2008051244A2
Authority
WO
WIPO (PCT)
Prior art keywords
acetyl
amino
benzoic acid
compound
alkyl
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/US2006/045950
Other languages
English (en)
Other versions
WO2008051244A3 (fr
Inventor
Jonathan David Bloom
Shabana Insaf
Thomas Nittoli
Alan Gordon Sutherland
Kevin J. Curran
Karen Wheless
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.)
Wyeth LLC
Original Assignee
Wyeth LLC
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 Wyeth LLC filed Critical Wyeth LLC
Priority to CA002631024A priority Critical patent/CA2631024A1/fr
Priority to JP2008543479A priority patent/JP2009519240A/ja
Priority to AU2006349612A priority patent/AU2006349612A1/en
Priority to BRPI0619132-0A priority patent/BRPI0619132A2/pt
Priority to EP06851777A priority patent/EP1966181A2/fr
Publication of WO2008051244A2 publication Critical patent/WO2008051244A2/fr
Anticipated expiration legal-status Critical
Publication of WO2008051244A3 publication Critical patent/WO2008051244A3/fr
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms

Definitions

  • heteroaryl moieties include: alkyl, alkoxy, halogen, amino, alkylamino, dialkylamino, trifluoromethyl, and trifluoromethoxy.
  • a heteroaryl moiety contains 1 to 9 carbon atoms.
  • Another embodiment of the compounds of formula (I) is wherein Y is O or NH and X is selected from the group consisting of H, halo, Ci -C 4 alkyl, C 1 -C 4 alkoxy, and Ci-C 4 haloalkyl.
  • a prodrug is intended to mean a compound that is converted under physiological conditions or by solvolysis or metabolically to a specified compound that is pharmaceutically active.
  • a prodrug containing such a moiety may be prepared according to conventional procedures by treatment of a compound of this invention containing, for example, an amido, carboxylic acid, or hydroxyl moiety with a suitable reagent.
  • the compounds, or the prodrugs, the pharmaceutically active metabolites or the pharmaceutically acceptable salts thereof, and the pharmaceutical compositions of the present invention may be delivered together with suitable diluents, preservatives, solubilizers, emulsif ⁇ ers, adjuvants and/or carriers useful in treatment or prevention of Hepatitis C viral infection.
  • compositions are liquids or lyophilized or otherwise dried formulations and include diluents of various buffer content (for example, Tris-HCl, acetate, phosphate), pH and ionic strength, additives such as albumins or gelatin to prevent absorption to surfaces, detergents (for example, TWEEN 20, TWEEN 80, PLURONIC F68, bile acid salts), solubilizing agents (for example, glycerol, polyethylene glycerol), anti-oxidants (for example ascorbic acid, sodium metabisulfate), preservatives (for example, thimerosal, benzyl alcohol, parabens), bulking substances or tonicity modifiers (for example, lactose, mannitol), covalent attachment of polymers such as polyethylene glycol, complexation with metal ions, or incorporation of the compound into or onto particulate preparations of hydrogels or liposomes, micro-emulsions, micelles, unilamellar or multilamellar
  • compositions will influence the physical state, solubility, stability, rate of in vivo release, and rate of in vivo clearance of the compound or composition.
  • the choice of compositions will depend on the physical and chemical properties of the compound capable of treating or preventing a Hepatitis C viral infection.
  • the compound, or the prodrugs, the pharmaceutically active metabolites or the pharmaceutically acceptable salts thereof, and the pharmaceutical compositions of the present invention may be delivered locally via a capsule that allows a sustained release of the compound over a period of time.
  • Controlled or sustained release compositions include formulation in lipophilic depots (for example, fatty acids, waxes, oils).
  • phenoxy and thiophenyl derivates of this invention are prepared by Method 2, as illustrated in Scheme 2.
  • ortho-acylphenol or ortho- acylthiophenol derivative 7 is prepared by reacting the corresponding acid chloride and a Lewis acid with a substituted phenol or thiophenol 6.
  • This methodology is described in Mewshaw, et al (Mewshaw, R.E.; Marquis, K.L.; Shi, X.; McGaughey, G.; Stack, G.; et al.; Tetrahedron; EN; 54; 25; 1998; 7081-7108).
  • Bovine Serum Albumin 10 mg/ml NEB (10OX at 10 mg/ml) #007-BSA

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

La présente invention concerne des composés de formule (I) : dans laquelle R1 est choisi dans le groupe composé de -C(O)R et (a), dans laquelle R6 et R7 sont choisis indépendamment parmi H, un alkyle, un cycloalkyle, un hétérocycloalkyle, un hétéroaryle ou un aryle, l'un d'eux pouvant être facultativement substitué, G est choisi parmi H ou un hydroxyle, Y est O, NH ou S, X est choisi dans le groupe composé de H, un halo, un alkyle, un cycloalkyle, un perfluoroalkyle, un alcoxy, un alkylthio, un amino, un alkylamino, un dialkylamino et CN, et n est 0, 1, 2 ou 3, ou un promédicament, un sel pharmaceutiquement acceptable ou un métabolite pharmaceutiquement actif de ceux-ci. L'invention concerne également des compositions contenant les composés de l'invention et des procédés d'utilisation à la fois des composés de l'invention et des compositions de ceux-ci pour traiter ou prévenir une infection par le virus de l'hépatite C ou pour inhiber la réplication du virus de l'hépatite C.
PCT/US2006/045950 2005-12-01 2006-12-01 Dérivés de l'acide anthranilique utilisables pour le traitement d'une infection par le virus de l'hépatite c Ceased WO2008051244A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002631024A CA2631024A1 (fr) 2005-12-01 2006-12-01 Derives de l'acide anthranilique utilisables pour le traitement d'une infection par le virus de l'hepatite c
JP2008543479A JP2009519240A (ja) 2005-12-01 2006-12-01 Ｃ型肝炎ウイルスの感染の治療に有用なアントラニル酸誘導体
AU2006349612A AU2006349612A1 (en) 2005-12-01 2006-12-01 Anthranilic acid derivatives useful in treating infection with Hepatitis C virus
BRPI0619132-0A BRPI0619132A2 (pt) 2005-12-01 2006-12-01 composto métodos para inibir a replicação de um vìrus de hepatite c, para tratar ou prevenir uma infecção viral de hepatite c em um mamìfero e para inibir rna polimerase dependente do rna de hepatite c, e, composição farmacêutica
EP06851777A EP1966181A2 (fr) 2005-12-01 2006-12-01 Dérivés de l'acide anthranilique utilisables pour le traitement d'une infection par le virus de l'hépatite c

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74177205P 2005-12-01 2005-12-01
US60/741,772 2005-12-01

Publications (2)

Publication Number Publication Date
WO2008051244A2 true WO2008051244A2 (fr) 2008-05-02
WO2008051244A3 WO2008051244A3 (fr) 2008-07-17

Family

ID=39273567

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/045950 Ceased WO2008051244A2 (fr) 2005-12-01 2006-12-01 Dérivés de l'acide anthranilique utilisables pour le traitement d'une infection par le virus de l'hépatite c

Country Status (7)

Country Link
EP (1) EP1966181A2 (fr)
JP (1) JP2009519240A (fr)
CN (1) CN101336236A (fr)
AU (1) AU2006349612A1 (fr)
BR (1) BRPI0619132A2 (fr)
CA (1) CA2631024A1 (fr)
WO (1) WO2008051244A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9682999B2 (en) 2011-08-19 2017-06-20 Glaxo Group Limited Benzofuran compounds for the treatment of hepatitis C virus infections

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003304040A1 (en) * 2002-10-08 2004-11-04 Viropharma Incorporated Anthranilic acid derivatives useful in treating infection with hepatitis c virus

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9682999B2 (en) 2011-08-19 2017-06-20 Glaxo Group Limited Benzofuran compounds for the treatment of hepatitis C virus infections

Also Published As

Publication number Publication date
JP2009519240A (ja) 2009-05-14
CA2631024A1 (fr) 2008-05-02
WO2008051244A3 (fr) 2008-07-17
BRPI0619132A2 (pt) 2011-09-13
CN101336236A (zh) 2008-12-31
EP1966181A2 (fr) 2008-09-10
AU2006349612A1 (en) 2008-05-02

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