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AR068794A1 - Compuestos antivirales - Google Patents

Compuestos antivirales

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Publication number
AR068794A1
AR068794A1 ARP080102758A ARP080102758A AR068794A1 AR 068794 A1 AR068794 A1 AR 068794A1 AR P080102758 A ARP080102758 A AR P080102758A AR P080102758 A ARP080102758 A AR P080102758A AR 068794 A1 AR068794 A1 AR 068794A1
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Argentina
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alkyl
cycloalkyl
alkynyl
alkenyl
och2p
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ARP080102758A
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Gilead Sciences Inc
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Publication of AR068794A1 publication Critical patent/AR068794A1/es

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    • 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
    • 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
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D401/14—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 three or more hetero 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/14—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 three or more hetero 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • 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
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Compuestos antivirales, composiciones que contienen tales compuestos y uso de los compuestos para preparar medicamentos utiles para tratar la hepatitis C. Reivindicacion 1: Un compuesto de formula (1) o su sal, o profármaco aceptable para uso farmacéutico, donde R1 se selecciona independientemente H, alquilo, alquenilo, alquinilo, arilo, cicloalquilo, heterociclo, halogeno, haloalquilo, alquilsulfonamido, arilsulfonamido, -C(O)NHS(O)2-, o -S(O)2-, opcionalmente sustituido con uno o más A3; R2 se selecciona de, a) -C(Y1)(A3), b) alquilo C2-10, cicloalquilo C3-7 o alquilo C1-4-cicloalquilo C3-7, donde dicho cicloalquilo y alquil-cicloalquilo puede estar opcionalmente mono-, di-o tri-sustituido con alquilo C1-3, o donde dicho alquilo, cicloalquilo y alquil-cicloalquilo puede estar opcionalmente mono- o di-sustituido con sustituyentes seleccionados de hidroxi y O-alquilo C1-4, o donde cada uno de dichos grupos alquilo puede estar opcionalmente mono-, di- o tri-sustituido con halogeno, o donde cada uno de dichos grupos cicloalquilo tiene 5, 6 o 7 miembros, uno o dos -CH2- grupos no está directamente enlazado uno con otro puede estar opcionalmente reemplazado por -O- de modo que el átomo O está enlazado al átomo N al cual R2 está unido mediante al menos dos átomos C, c) fenilo, alquilo C1-3-fenilo, heteroarilo o alquilo C1-3-heteroarilo, donde los grupos heteroarilo son de 5 o 6 miembros que tienen de 1 hasta 3 heteroátomos seleccionados de N, O y S, donde dichos grupos fenilo y heteroarilo pueden estar opcionalmente mono-, di- o trisustituido con sustituyentes seleccionados de halogeno, -OH, alquilo C1-4, O-alquilo C1-4, S-alquilo C1-4, -NH2, -CF3, -NH(alquilo C1-4) y -N(alquilo C1-4)2, -CONH2 y -CONH-alquilo C1-4; y donde dicho alquilo C1-3 puede estar opcionalmente sustituido con uno o más halogeno; d) -S(O)2(A3); o e) -C(Y1)-X-Y; R3 es H o alquilo C1-6; Y1 es independientemente O, S, N(A3), N(O)(A3), N(OA3), N(O)(OA3) o N(N(A3)(A3)); Z es O, S, o NR3; Z1 es un grupo orgánico que tiene una forma tridimensional que se adaptará a la region S2 extendida del dominio de la NS3 serina proteasa del VHC; Z2b es H, alquilo C1-10, alquenilo C2-10, alquinilo C2-10; Q1 es A3; o Q1 y Z2a tomados juntos con los átomos a los cuales están unidos forman un heterociclo, dicho heterociclo puede estar opcionalmente sustituido con uno o más oxo (=O), R4, o A3; cada X es independientemente un enlace, O, S, o NR3; Y es un policarbociclo o un poliheterociclo, dicho policarbociclo o un poliheterociclo está opcionalmente sustituido con uno o más R4, halo, carboxi, hidroxi, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcanoilo C1-10, alcoxi C1-10, alcanoiloxi C1-10, alcoxi C1-10carbonilo, NRnRp, SRr, S(O)Rr, o S(O)2Rr; cada R4 es independientemente -P(Y3)(OA2)(OA2), -P(Y3)(OA2)(N(A2)2), -P(Y3)(A2)(OA2), -P(Y3)(A2)(N(A2)2), o P(Y3)(N(A2)2)(N(A2)2); cada Y es independientemente O, S, o NR3; cada Rn y Rp es independientemente H, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcanoilo C1-10, alcoxi C1-10, alcanoiloxi C1-10, o alcoxi C1-10carbonilo, dicho alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcanoilo C1-10, alcoxi C1-10, alcanoiloxi C1-10, o alcoxi C1-10carbonilo, está opcionalmente sustituido con uno o más R4, halo, hidroxi, carboxi, ciano, o alcoxi C1-10; o Rn y Rp juntos con el nitrogeno al cual están unidos forman un anillo pirrolidina, piperidina, piperazina, morfolino o tiomorfolino; cada Rr es independientemente H, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcanoilo C1-10, o alcoxi C1-10carbonilo; Z2a es H, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, haloalquilo, C1-10alquil-S(=O)2-alquilo C1-10, o cicloalquilo, donde cualquier átomo de carbono de Z2a puede estar opcionalmente reemplazado con un heteroátomo seleccionado de O, S, S(=O), S(=O)2, o N y donde cualquier cicloalquilo está opcionalmente sustituido con uno o más alquilo C1-10, alquenilo C2-10, alquinilo C2-10, haloalquilo, F, CI, Br, o l; o Z2a opcionalmente forma un heterociclo con uno o más R1, R2, Q1, o A3; A3 se selecciona independientemente PRT, H, -OH, -C(O)OH, ciano, alquilo, alquenilo, alquinilo, amino, amido, imido, mino, halogeno, CF3, CH2CF3, cicloalquilo, nitro, arilo, aralquilo, alcoxi, ariloxi, heterociclo, -C(A2)3, -C(A2)2-C(O)A2, -C(O)A2, -C(O)OA2, -O(A2), -N(A2)2, -S(A2), -CH2P(Y1)(A2)(OA2), -CH2P(Y1)(A2)(N(A2)2), -CH2P(Y1)(OA2)(OA2), -OCH2P(Y1)(OA2)(OA2), -OCH2P(Y1)(A2)(OA2), -OCH2P(Y1)(A2)(N(A2)2), -C(O)OCH2P(Y1)(OA2)(OA2), -C(O)OCH2P(Y1)(A2)(OA2), -C(O)OCH2P(Y1)(A2)(N(A2)2), -CH2P(Y1)(OA2)(N(A2)2), -OCH2P(Y1)(OA2)(N(A2)2), -C(O)OCH2P(Y1)(OA2)(N(A2)2), -CH2P(Y1)(N(A2)2)(N(A2)2), -C(O)OCH2P(Y1)(N(A2)2)(N(A2)2), -OCH2P(Y1)(N(A2)2)(N(A2)2), (CH2)m-heterociclo, -(CH2)mC(O)O-alquilo, -O-(CH2)m-O-C(O)-O-alquilo, -O-(CH2)r-O-C(O)-(CH2)m-alquilo, -(CH2)mO-C(O)-O-alquilo, -(CH2)m-OC(O)O-cicloalquilo, -N(H)C(Me)C(O)O-alquilo, SRr, S(O)Rr, S(O)2Rr, o alcoxi arilsulfonamida, donde cada A3 puede estar opcionalmente sustituido con 1 hasta 4 -R1, -P(Y1)(OA2)(OA2), -P(Y1)(OA2)(N(A2)2), -P(Y1)(A2)(OA2), -P(Y1)(A2)(N(A2)2), o P(Y1)(N(A2)2)(N(A2)2), -C(=O)N(A2)2), halogeno, alquilo, alquenilo, alquinilo, arilo, carbociclo, heterociclo, aralquilo, arilo sulfonamida, arilo alquilsulfonamida, ariloxi sulfonamida, ariloxi alquilsulfonamida, ariloxi arilsulfonamida, alquilo sulfonamida, alquiloxisulfonamida, alquiloxi alquilsulfonamida, ariltio, -(CH2)m-heterociclo, -(CH2)m-C(O)O-alquilo, -O(CH2)mOC(O)O-alquilo, -O-(CH2)m-OC(O)-(CH2)m-alquilo, -(CH2)m-O-C(O)-O-alquilo, -(CH2)m-O-C(O)-O-cicloalquilo, -N(H)C(CH3)C(O)O-alquilo, o alcoxi arilsulfonamida, opcionalmente sustituido con R1; opcionalmente cada instancia independiente de A3 y Q1 pueden ser tomados juntos con uno o más A3 o Q1 grupos para formar un anillo; y A2 se selecciona independientemente PRT, H, alquilo, alquenilo, alquinilo, amino, aminoácido, alcoxi, ariloxi, ciano, haloalquilo, cicloalquilo, arilo, heteroarilo, heterociclo, alquilsulfonamida, o arilsulfonamida, donde cada A2 está opcionalmente sustituido con A3; Rf es A3; y m es 0 hasta 6; siempre que el compuesto de formula (1) no sea el compuesto de la formula (2).
ARP080102758A 2007-06-29 2008-06-26 Compuestos antivirales AR068794A1 (es)

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US93775207P 2007-06-29 2007-06-29
US95969807P 2007-07-16 2007-07-16

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US (2) US8513186B2 (es)
EP (1) EP2162432A2 (es)
JP (2) JP5465667B2 (es)
KR (1) KR20100038417A (es)
CN (1) CN101801925A (es)
AP (1) AP2009005073A0 (es)
AR (1) AR068794A1 (es)
AU (1) AU2008271117B2 (es)
BR (1) BRPI0813733A2 (es)
CA (1) CA2692145C (es)
CO (1) CO6251241A2 (es)
EA (1) EA200971074A1 (es)
EC (1) ECSP109906A (es)
IL (1) IL202623A0 (es)
MX (1) MX2009013830A (es)
SG (1) SG182979A1 (es)
TW (1) TW200914013A (es)
WO (1) WO2009005677A2 (es)
ZA (1) ZA201000614B (es)

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