AR047444A1 - Peptidos macrociclicos activos contra el virus de la hepatitis c - Google Patents

Peptidos macrociclicos activos contra el virus de la hepatitis c

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Publication number
AR047444A1
AR047444A1 ARP050100220A ARP050100220A AR047444A1 AR 047444 A1 AR047444 A1 AR 047444A1 AR P050100220 A ARP050100220 A AR P050100220A AR P050100220 A ARP050100220 A AR P050100220A AR 047444 A1 AR047444 A1 AR 047444A1
Authority
AR
Argentina
Prior art keywords
alkyl
cycloalkyl
4alkyl
aryl
het
Prior art date
Application number
ARP050100220A
Other languages
English (en)
Inventor
Murray Douglas Bailey
Punit Bhardwaj
Francois Bilodeau
Montse Llinas Brunet
Pasquale Forgione
Elise Ghiro
Nathalie Goudreau
Ted Halmos
Jean Rancourt
Original Assignee
Boehringer Ingelheim Int
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 Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR047444A1 publication Critical patent/AR047444A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA 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
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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

Abstract

La presente se refiere a péptidos macrocíclicos activos contra el virus de la hepatitis C. Son utiles como inhibidores de la proteasa NS3 del HCV. Composicion farmacéutica que comprende dichos compuestos, así como métodos de tratamiento de una infeccion viral de hepatitis C. Reivindicacion 1: Un compuesto de formula (1) caracterizado porque R1 es hidroxi o NHSO2R11 en donde R11 es alquilo C1-6, alquenilo C2-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, arilo, Het, aril-alquilo C1- 4, o Het-alquilo C1-4; a) estando dichos alquilo C1-6, alquenilo C2-6, arilo, Het, cicloalquil C3-7-alquilo C1-6-, aril-alquilo C1-4, y Het-alquilo C1-4 opcionalmente sustituidos con uno, dos o tres sustituyentes cada uno independientemente seleccionado de halogeno, hidroxi, ciano, nitro, alquilo C1-6, haloalquilo C1-6, -O-haloalquilo C1-6, -O-arilo, -C(=O)-alquilo C1-6, -C(=O)-NH2, -C(=O)-NHalquilo C1-4, -C(=O)-N(alquilo C1-4)2, -NH2,.-NHalquilo C1-4 y -N(alquilo C1-4)2; y b) estando dicho cicloalquilo C3-7 opcionalmente sustituido con uno o más sustituyentes cada uno independientemente seleccionado de nitro, halogeno, hidroxi, ciano, -O-alquilo C1-6, alquenilo C2-4, -O-haloalquilo C1-6, -NH2, -NHalquilo C1-4, -N(alquilo C1-4)2, trialquil C1-6-sililo, R41, -C(=O)-R41, -C(=O)OR41, -C(=O)N(R42)R41, -SO2R41, y -OC(=O)-R41; en donde R41 en cada caso se selecciona independientemente de: i) H, cicloalquilo C3-7, cicloalquenilol C4-7, Het, o aril-alquilo C1-4-O-, ii) arilo o ariloxi, estando cada uno de los cuales opcionalmente sustituido con alquilo C1-6; y iii) alquilo C1-8 opcionalmente sustituido con uno o más sustituyentes cada uno independientemente seleccionado de -O-alquilo C1-6, hidroxi, halogeno, alquenilo C2- 10, alquinilo C2-10, cicloalquilo C3-7, cicloalquenilol C4-7, arilo, Het, ariloxi, y aril-alquilo C1-4-O-, en donde cada uno de dichos arilo y ariloxi está opcionalmente sustituido con alquilo C1-6; y R42 se selecciona de H y alquilo C1-6; o R11 es - N(R11a)(R11b), en donde R11a y R11b se seleccionan cada uno independientemente de H, alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, arilo, aril-alquilo C1-6, Het y Het-alquilo C1-4; en donde dichos alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, arilo, aril-alquilo C1-6, Het y Het-alquilo C1-4 están cada uno opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de halogeno, alquilo C1-6, hidroxi, ciano, nitro, haloalquilo C1-6, - O-alquilo C1-6, -O-haloalquilo C1-6, NH2, -NHalquilo C1-4, -N(alquilo C1-4)2, -C(=O)-NH2, -C(=O)-NHalquilo C1-4, -C(=O)-N(alquilo C1-4)2, -C(=O)-alquilo C1-6, -COOH, y -COOalquilo C1-6, o R11a y R11b están enlazados, junto con el átomo de N al que están unidos, para formar un heterociclo monocíclico saturado o insaturado de 3 a 7 miembros opcionalmente fusionado a al menos otro ciclo para formar un heteropoliciclo y heteropoliciclo opcionalmente de uno a tres heteroátomos más cada uno independientemente seleccionado de N, S y O, y estando opcionalmente sustituidos con uno o más sustituyentes cada uno independientemente seleccionado de halogeno, alquilo C1-6, hidroxi, ciano, nitro, haloalquilo C1-6, -O-alquilo C1-6, -O-haloalquilo C1-6, -NH2, NHalquilo C1-4, -N(alquilo C1-4)2, -C(=O)-NH2, -C(=O)-NHalquilo C1-4, -C(=O)-N(alquilo C1-4)2, -C(=O)-alquilo C1-6, -COOH, y -COOalquilo C1-6; R2 es un grupo de formula (2), en donde R20 es H, OH, halogeno, o Y1-R20a en donde Y1 es un enlace, O, S, o NR20b y en donde: R20a se selecciona del grupo que consiste en: alquilo C1-8, alquil C1-6-C:::N, alquenilo C2-8, alquinilo C2-8 y cicloalquilo C3-7, estando cada uno de dichos alquilo, alquenilo, alquinilo y cicloalquilo opcionalmente sustituido con uno, dos o tres sustituyentes, cada uno independientemente seleccionado de: halogeno, alquilo C1-6 opcionalmente sustituido con -O-alquilo C1-6 o -O-cicloalquilo C3-6, cicloalquilo C3-7, -O-alquilo C1-6, Het, -O- cicloalquilo C3-6, -NH2, -NHalquilo C1-4 y -N(alquilo C1-4)2; y R20b es H, alquilo C1-6 o cicloalquilo C3-6; y W es N; y la línea de puntos ôaö es un enlace doble; o R20 es oxo, y W es NR23 en donde R23 es H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6; y la línea de puntos ôaö es un enlace sencillo; R21 es halogeno o Y2-R21a, en donde Y2 es un enlace, O, S, SO o SO2, y R21a es alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7 o cicloalquil C3-7-alquilo C1-6, o R2 es un grupo de formula (3), en donde R2, W y la línea de puntos ôaö son como se han definido antes; R24 es H o R21 como se ha definido antes; R25 es H o alquilo C1-6; X es O o NH; R3 es alquilo C1-10, cicloalquilo C3-7 o cicloalquil C3-7-alquilo C1-4, a) en donde el cicloalquilo y el cicloalquil-alquilo pueden estar mono- di- o tri- sustituidos con alquilo C1-3; b) en donde el alquilo, el cicloalquilo y el cicloalquil-alquilo pueden estar mono- o di-sustituido con sustituyentes seleccionados cada uno independientemente de hidroxi y O-alquilo C1-6; c) en donde cada grupo alquilo puede estar mono- di- o tri-sustituido con halogeno; y d) en donde en cada grupo cicloalquilo que es de 5-, 6- 0 7 miembros, uno o dos grupos -CH2- que no están directamente unidos uno al otro pueden estar reemplazados por -O- de tal modo que el átomo de O está unido al grupo X por al menos dos átomos de C; D es una cadena de alquileno de 3 a 8 átomos saturada o insaturada; y la línea de puntos ôbö es un enlace sencillo o un enlace doble; en donde Het tal como se usa en la presente memoria se define como un heterociclo de 3 a 7 miembros que tiene 1 a 4 heteroátomos cada uno independientemente seleccionado de O, N y S, que pueden ser saturados, insaturados o aromáticos, y que está opcionalmente fusionado a al menos otro ciclo para formar un heteropoliciclo de 4 a 14 miembros que tiene siempre que sea posible 1 a 5 heteroátomos, cada uno independientemente seleccionado de O, N y S, siendo dicho heteropoliciclo saturado, insaturado o aromático; o una de sus sales o ésteres farmacéuticamente aceptables; con la condicion de que cuando R2 es un grupo de formula (2); y W es N; y la línea de puntos ôaö es un enlace doble; y R20 es h, halogeno, o Y1-R20a, en donde Y1 es O y R20a es alquilo C1-6 o cicloalquilo C3-6; o Y1 es un enlace y R20a es alquilo C1-6; y R21 es halogeno o Y2-R21a, en donde Y2 es O y R21a es alquilo C1-6 o cicloalquilo C3-6; y 22 es H; y R3 es alquilo C1-6 opcionalmente sustituido con halo, o R3 es -(CH2)p-cicloalquilo C3-7, en donde p es 0-4, o R3 es un anillo de tetrahidrofurano enlazado a través de la posicion C3 o C4 del anillo; entonces R1 no es NHSO2R11 en donde R11 es alquilo C1-6 o cicloalquilo C3-7 no sustituido.
ARP050100220A 2004-01-21 2005-01-21 Peptidos macrociclicos activos contra el virus de la hepatitis c AR047444A1 (es)

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US53786304P 2004-01-21 2004-01-21

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AR047444A1 true AR047444A1 (es) 2006-01-18

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US (2) US7749961B2 (es)
EP (1) EP1730167B1 (es)
JP (1) JP4682155B2 (es)
AR (1) AR047444A1 (es)
AT (1) ATE495185T1 (es)
CA (1) CA2549851C (es)
DE (1) DE602005025855D1 (es)
ES (1) ES2358333T3 (es)
PE (1) PE20050764A1 (es)
TW (1) TW200528094A (es)
UY (1) UY28722A1 (es)
WO (1) WO2005070955A1 (es)

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