AR070027A1 - Agentes anti-infecciosos contra el virus hcv - Google Patents

Agentes anti-infecciosos contra el virus hcv

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Publication number
AR070027A1
AR070027A1 ARP080104045A ARP080104045A AR070027A1 AR 070027 A1 AR070027 A1 AR 070027A1 AR P080104045 A ARP080104045 A AR P080104045A AR P080104045 A ARP080104045 A AR P080104045A AR 070027 A1 AR070027 A1 AR 070027A1
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AR
Argentina
Prior art keywords
group
alkyl
amino
independently selected
heterocyclyl
Prior art date
Application number
ARP080104045A
Other languages
English (en)
Inventor
Jian Gao
Ii T Franczyk
D Betebenner
Lei Huang
K Sarris
C Motter
D Barnes
W Kati
A Krueger
C Flentge
G Zhang
D Liu
Huaquing Liu
C Maring
X Lou
B Kotecki
R Henry
M Tufano
D Hutchinson
A Haight
D Degoey
J Hengeveld
J Pratt
J Randolph
P Donner
T Rockway
K Stewart
K Longenecker
Shu-Ping Chen
Rolf Wagner
Original Assignee
Abbott Lab
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39948002&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR070027(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Abbott Lab filed Critical Abbott Lab
Publication of AR070027A1 publication Critical patent/AR070027A1/es

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    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D403/10—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 carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Communicable Diseases (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Steroid Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Esta solicitud se relaciona con: (a) compuestos y sales de los mismos que, entre otros, inhiben el HCV; (b) intermediarios de utilidad para la preparacion de dichos compuestos y sales; (c) composiciones que comprenden dichos compuestos y sales; (d) métodos para preparar dichos intermediarios, compuestos, sales y composiciones; (e) método para tratar hepatitis C en mamíferos, y métodos de preparacion de dichos compuestos. Estos compuestos resultan utiles para el tratamiento de enfermedad causada por un virus hepatotropico (HCV). Reivindicacion 1: Un compuesto o su sal, caracterizado porque; el compuesto corresponde en estructura a la formula (1); ------- se selecciona del grupo formado por un enlace simple carbono-carbono y un enlace doble carbono-carbono; R1 se selecciona del grupo formado por hidrogeno, metilo, y grupo protector de nitrogeno; R2 se selecciona del grupo formado por hidrogeno, halo, hidroxi, metilo, ciclopropilo, y ciclobutilo; R3 se selecciona del grupo formado por hidrogeno, halo, oxo, y metilo; R4 se selecciona del grupo formado por halo, alquilo, alquenilo, alquinilo, nitro, ciano, azido, alquiloxi, alqueniloxi, alquiniloxi, amino, aminocarbonilo, aminosulfonilo, alquilsulfonilo, carbociclilo, y heterociclilo, en donde: (a) el amino, aminocarbonilo, y aminosulfonilo están opcionalmente sustituidos con: (1) uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, y alquilsulfonilo, o (2) dos sustituyentes que, junto con el nitrogeno del amino, forman un heterociclilo de un solo anillo, y (b) el alquilo, alquenilo, alquinilo, alquiloxi, alqueniloxi, alquiniloxi, y alquilsulfonilo, están opcionalmente sustituidos con uno o más sustituyentes seleccionados en forma independiente del grupo formado por halo, oxo, nitro, ciano, azido, hidroxi, amino, alquiloxi, trimetilsililo, carbociclilo, y heterociclilo, en donde: el amino está opcionalmente sustituido con: (1) uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, alquilcarbonilo, alquilsulfonilo, alquiloxicarbonilo, carbociclilo, heterociclilo, carbociclilalquilo, y heterociclilalquilo, o (2) dos sustituyentes que, junto con el nitrogeno del amino, forman un heterociclilo de un solo anillo, y (c) el carbociclilo y heterociclilo están opcionalmente sustituidos con hasta tres sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, halo, oxo, nitro, ciano, azido, hidroxi, amino, alquiloxi, trimetilsililo, carbociclilo, y heterociclilo, en donde: el amino está opcionalmente sustituido con: (1) uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, alquilcarbonilo, alquilsulfonilo, alquiloxicarbonilo, carbociclilo, heterociclilo, carbociclilalquilo, y heterociclilalquilo, o (2) dos sustituyentes que, junto con el nitrogeno del amino, forman un heterociclilo de un solo anillo; R5 se selecciona del grupo formado por hidrogeno, hidroxi, alquilo, alquenilo, alquinilo, alquiloxi, alqueniloxi, alquiniloxi, alquilsulfoniloxi, carbociclilsulfoniloxi, haloalquilsulfoniloxi, y halo; en cuanto a L y R6, L es un enlace, y R6 se selecciona del grupo formado por carbociclilo de 2 anillos fusionados y heterociclilo de 2 anillos fusionados, en donde cada uno de tales sustituyentes está opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente del grupo formado por RE, RF, RG, RH, RI, RJ, y RK, o L se selecciona del grupo formado por C(RA)=C(RB), C:::C, C(O)N(RC), N(RD)C(O), alquileno C1-2, C(H)2O, OC(H)2, ciclopropil-1,2-eno, C(H)2N(RL), N(RM)C(H)2, C(O)CH2, y CH2C(O), y R6 se selecciona del grupo formado por carbociclilo C5-6 y heterociclilo de 5-6 miembros, en donde cada uno de tales sustituyentes está opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente del grupo formado por RE, RF, RG, RH, RI, RJ, y RK; RA, RB, RL, y RM se seleccionan en forma independiente de grupo formado por hidrogeno, alquilo C1-6, alquiloxi C1-6, cicloalquilo C3-8 y halo, en donde: el alquilo C1-6 está opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente del grupo formado por carboxi, halo, hidroxi, nitro, oxo, amino, ciano, alquiloxicarbonilo, alquilcarboniloxi, alquiloxi, carbociclilo, y heterociclilo; RC se selecciona del grupo formado por hidrogeno y alquiIo; RD se selecciona del grupo formado por hidrogeno y alquilo; cada RE se selecciona en forma independiente del grupo formado por halo, nitro, hidroxi, oxo, carboxi, ciano, amino, imino, azido, y aldehído, en donde: el amino está opcionalmente sustituido con uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, y alquinilo; cada RF se selecciona en forma independiente del grupo formado por alquilo, alquenilo, y alquinilo, en donde: cada uno de tales sustituyentes está opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente del grupo formado por carboxi, hidroxi, halo, amino, imino, nitro, azido, oxo, aminosulfonilo, alquilsulfonilo, alquiloxicarbonilo. alqueniloxicarbonilo, alquiniloxicarbonilo, alquilcarboniloxi, alquenilcarboniloxi, alquinilcarboniloxi, alquiloxi, alqueniloxi, alquiniloxi, carbociclilo, heterociclilo, ciano, y aminocarbonilo, en donde: el amino, imino, aminosulfonilo, aminocarbonilo, carbociclilo, y heterociclilo están opcionalmente sustituidos con uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, alquilsulfonilo, alquenilsulfonilo, alquinilsulfonilo, alquilsulfonilamino, hidroxi, y alquiloxi, en donde: la porcion amino del alquilsulfonilamino está opcionalmente sustituida con un sustituyente seleccionado del grupo formado por alquilo, alquenilo, y alquinilo; cada RG se selecciona en forma independiente del grupo formado por carbociclilo y heterociclilo, en donde: cada uno de tales sustituyentes está opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, carboxi, hidroxi, halo, amino, nitro, azido, oxo, aminosulfonilo, alquiloxicarbonilo, alqueniloxicarbonilo, alquiniloxicarbonilo, alquilcarboniloxi, alquenilcarboniloxi, alquinilcarboniloxi, alquiloxi, alqueniloxi, alquiniloxi, carbociclilo, heterociclilo, ciano, y aminocarbonilo, en donde: el amino, aminosulfonilo, y aminocarbonilo están opcionalmente sustituidos con uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, alquilsulfonilo, alquenilsulfonilo, y alquinilsulfonilo; cada RH se selecciona en forma independiente del grupo formado por alquiloxi, alqueniloxi, alquiniloxi, alquilsulfoniloxi, alquenilsulfoniloxi, y alquinilsulfoniloxi, en donde: cada uno de tales sustituyentes está opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente del grupo formado por carboxi, hidroxi, halo, amino, nitro, azido, oxo, aminosulfonilo, alquiloxicarbonilo, alqueniloxicarbonilo, alquiniloxicarbonilo, alquilcarboniloxi, alquenilcarboniloxi, alquinilcarboniloxi, alquiloxi, alqueniloxi, alquiniloxi, carbociclilo, heterociclilo, ciano, y aminocarbonilo, en donde; el amino, aminosulfonilo, y aminocarbonilo están opcionalmente sustituidos con uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, alquilsulfonilo, alquenilsulfonilo, y alquinilsulfonilo; cada RI se selecciona en forma independiente del grupo formado por alquilcarbonilo, alquenilcarbonilo, alquinilcarbonilo, aminocarbonilo, alquiloxicarbonilo, carbociclilcarbonilo, y heterociclilcarbonilo, en donde: (a) el alquilcarbonilo, alquenilcarbonilo, y alquinilcarbonilo están opcionalmente sustituidos con uno o más sustituyentes seleccionados en forma independiente del grupo formado por carboxi, hidroxi, halo, amino, nitro, azido, oxo, aminosulfonilo, alquiloxicarbonilo, alqueniloxicarbonilo, alquiniloxicarbonilo, alquilcarboniloxi, alquenilcarboniloxi, alquinilcarboniloxi, alquiloxi, alqueniloxi, alquiniloxi, carbociclilo, heterociclilo, ciano, y aminocarbonilo, y (b) el aminocarbonilo está opcionalmente sustituido con uno o dos sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, alquiloxialquilo, carbociclilo, heterociclilo, alquilsulfonilo, y alquilsulfonilamino, en donde: el carbociclilo y heterociclilo están opcionalmente sustituidos con uno o dos sustituyentes seleccionados en forma independiente del grupo formado por halo, alquilo, y oxo; cada RJ se selecciona en forma independiente del grupo formado por carbociclilsulfonilamino, heterociclilsulfonilamino, alquilcarbonilamino, alquenilcarbonilamino, alquinilcarbonilamino, alquiloxicarbonilamino, alqueniloxicarbonilamino, alquiniloxicarbonilamino, alquilsulfonilamino, alquenilsulfonilamino, alquinilsulfonilamino, aminocarbonilamino, aIquiloxicarbonilaminoimino, alquilsulfonilaminoimino, alquenilsulfonilaminoimino, y alquinilsulfonilaminoimino, en donde: (a) la porcion amino de tales sustituyentes está opcionalmente sustituida con un sustituyente seleccionado en forma independiente del grupo formado por carbociclilalquilo, heterociclilalquilo, alquilcarboniloxi, aminocarbonilalquilo, alquilo, alquenilo, alquinilo, alquilcarbonilo, alquenilcarbonilo, alquinilcarbonilo, alquiloxicarbonilo, alquiloxialquiloxicarbonilo, alquilcarboniloxialquilo, y alquilsulfonilo, en donde: (1) la porcion carbociclilo del carbociclilalquilo y la porcion heterociclilo del heterociclilalquilo están opcionalmente sustituidos con uno o más sustituyentes seleccionados en forma independiente del grupo formado por alquilo, alquenilo, alquinilo, carboxi, hidroxi, alquiloxi, alqueniloxi, alquiniloxi, halo, nitro, ciano, azido, oxo, y amino, y (
ARP080104045A 2007-09-17 2008-09-17 Agentes anti-infecciosos contra el virus hcv AR070027A1 (es)

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