US2015342932A1PendingUtilityA1
Anti-viral compounds
Est. expiryJan 15, 2033(~6.5 yrs left)· nominal 20-yr term from priority
A61K 31/47C07D 513/04A61K 31/5377A61K 31/429A61P 31/12A61P 31/14Y02A50/30
48
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Claims
Abstract
Disclosed herein are compounds and related compositions for the treatment of viral infection, including RNA viral infection, and compounds that can modulate the RIG-I pathway in vertebrate cells, including compounds that can activate the RIG-I pathway.
Claims
exact text as granted — not AI-modified1 - 26 . (canceled)
27 . A method of treating or preventing a viral infection in a vertebrate comprising administering to the vertebrate a pharmaceutical composition comprising a compound represented by a formula:
wherein a dashed line indicates the presence or absence of a pi bond;
A and B are each independently single or double covalent bonds;
L is A-C(═R x )—NR 5 —B,
A-SO 2 —NR 5 —B,
A-N R 5 —SO 2 —B,
A-CH(CF 3 )—NR 5 —B,
A-NR 5 —CH(CF 3 )—B,
A-N R 5 —C(═R y )—NR 5 —B,
A-CR 2 R 3 —R x —B,
A-O—CR 2 R 3 —B,
A-S—CR 2 R 3 —B,
A-C(R 2 )═C(R 3 )—B,
where m and n are independently an integer from 0-5 such that m+n≧1,
R 1 is R a , OR 2 or NR 2 R 3 ;
each R a is independently H, hydrocarbyl optionally substituted by OR b , OCF 3 , OCOR b , COOR b , CON b R c , SR b , NR b R c , NR b COR c , SO 2 NR b R c , NO 2 , F, Cl, Br, CN, heterocycloalkyl; aryl optionally substituted by OR b , OCF 3 , OCOR b , COOR b , CON b R c , SR b NR b R c , NR b COR c , SO 2 NR b R c , NO 2 , F, Cl, Br, CN, heterocycloalkyl; or heteroaryl optionally substituted by OR b , OCF 3 , OCOR b , COOR b , CON b R c , SR b , NR b R c , NR b COR c , SO 2 NR b R c , NO 2 , F, Cl, Br, CN, heterocycloalkyl;
R 2 and R 3 are each independently R a , COR a , C(═O)OR a , or SO 2 R a ;
Y 5 , Y 6 , Y 7 and Y 8 are each independently CR 4 , N, or O;
R 4 is R 2 , OR a , NR 2 R 3 , SR a , SOR a , SO 2 R a , SO 2 NHR a , N(R 5 )COR a , halogen, trihalomethyl, CN, S═O, or nitro;
each R 5 is independently R a , COR a , SO 2 R a , or is not present;
W 1 and W 2 are each independently, O, S, NH, or CH 2 ;
each R x is independently O, S, CR 2 R 3 , or NR 5 ;
R y is S, N—CN, or CHR 4 ;
R z is R b , OR b , SR b , COR b , CO 2 R b , OCOR b , NR b R c , CON b R c , NR b COR c , SO 2 NR b R c , CF 3 , CN, NO 2 , F, Cl, Br, I, or C 2-5 heterocyclyl;
each R b is independently H or C 1-3 hydrocarbyl, and each R c is independently H or C 1-3 alkyl; and
Z 1 and Z 2 are each independently C or N.
28 . The method of claim 27 wherein the compound is represented by a formula
wherein
R 10 , R 13 , R 14 , R 19 , R 20 , R 21 , and R 22 are independently R b , OR b , SR b , COR b , CO 2 R b , OCOR b , NR b R c , CON b R c , NR b COR c , SO 2 NR b R c , CF 3 , CN, NO 2 , F, Cl, Br, I, or C 2-5 heterocyclyl; each R b is independently H or C 1-3 hydrocarbyl, and each R c is independently H or C 1-3 alkyl.
29 . The method of claim 27 , wherein R 1 is optionally substituted naphthyl or optionally substituted phenyl.
30 . The method of claim 27 , wherein the compound is further represented by a formula:
31 . The method of claim of claim 27 , wherein in the compound, R 5 is H or C 1-3 alkyl.
32 . The method of claim 27 , wherein the compound is further represented by a formula
wherein
R 10 , R 11 , R 12 , R 13 , and R 14 are independently R b , OR b , COR b , CO 2 R b , OCOR b , NR b R c , CF 3 , CN, NO 2 , F, Cl, Br, or I, wherein R b and R c are independently H or C 1-3 alkyl; and, R 5 is H or C 1-3 alkyl.
33 . The method of claim 27 , wherein in the compound, R z is CH 3 .
34 . The method of claim 27 , wherein in the compound, R 13 is Br.
35 . The method of claim 27 , wherein the compound is further represented by a formula
36 . The method of claim 27 wherein the viral infection is caused by a virus from one or more of the following families: Arenaviridae, Astroviridae, Birnaviridae, Bromoviridae, Bunyaviridae, Caliciviridae, Closteroviridae, Comoviridae, Cystoviridae, Flaviviridae, Flexiviridae, Hepevirus, Leviviridae, Luteoviridae, Mononegavirales, Mosaic Viruses, Nidovirales, Nodaviridae, Orthomyxoviridae, Picobirnavirus, Picornaviridae, Potyviridae, Reoviridae, Retroviridae, Sequiviridae, Tenuivirus, Togaviridae, Tombusviridae, Totiviridae, Tymoviridae, Hepadnaviridae, Herpesviridae, Paramyxoviridae or Papillomaviridae
37 . The method of claim 27 wherein the viral infection is influenza virus, Hepatitis C virus, West Nile virus, SARS-coronavirus, poliovirus, measles virus, Dengue virus, yellow fever virus, tick-borne encephalitis virus, Japanese encephalitis virus, St. Louis encephalitis virus, Murray Valley virus, Powassan virus, Rocio virus, louping-ill virus, Banzi virus, Ilheus virus, Kokobera virus, Kunjin virus, Alfuy virus, bovine diarrhea virus, Kyasanur forest disease virus, respiratory syncytial virus or human immunodeficiency virus (HIV).
38 . The method of claim 27 , wherein the pharmaceutical composition is administered as an adjuvant for a prophylactic or therapeutic vaccine.
39 . The method of claim 37 wherein the method comprises vaccinating a vertebrate by additionally administering a vaccine against influenza virus, Hepatitis C virus, West Nile virus, SARS-coronavirus, poliovirus, measles virus, Dengue virus, yellow fever virus, tick-borne encephalitis virus, Japanese encephalitis virus, St. Louis encephalitis virus, Murray Valley virus, Powassan virus, Rocio virus, louping-ill virus, Banzi virus, Ilheus virus, Kokobera virus, Kunjin virus, Alfuy virus, bovine diarrhea virus, Kyasanur forest disease virus, respiratory syncytial virus or human immunodeficiency virus (HIV).
40 . A method of modulating the innate immune response in a eukaryotic cell, comprising administering to the eukaryotic cell a compound represented by a formula:
wherein a dashed line indicates the presence or absence of a pi bond;
A and B are each independently single or double covalent bonds;
L is A-C(═R x )—NR 5 —B,
A-SO 2 —NR 5 —B,
A-NR 5 —SO 2 —B,
A-CH(CF 3 )—NR 5 —B,
A-NR 5 —CH(CF 3 )—B.
A-NR 5 —C(═R y )—NR 5 —B,
A-CR 2 R 3 —R x —B,
A-O—CR 2 R 3 —B,
A-S—CR 2 R 3 —B,
A-C(R 2 )═C(R 3 )—B,
where m and n are independently an integer from 0-5 such that m+n≧1,
R 1 is R a , OR 2 or NR 2 R 3 ;
each R a is independently H, hydrocarbyl optionally substituted by OR b , OCF 3 , OCOR b , COOR b , CON b R c , SR b , NR b R c , NR b COR c , SO 2 NR b R c , NO 2 , F, Cl, Br, CN, heterocycloalkyl; aryl optionally substituted by OR b , OCF 3 , OCOR b , COOR b , CON b R c , SR b , NR b R c , NR b COR c , SO 2 NR b R c , NO 2 , F, Cl, Br, CN, heterocycloalkyl; or heteroaryl optionally substituted by OR b , OCOR b , COOR b , CON b R c , SR b , NR b R c , NR b COR c , SO 2 NR b R c , NO 2 , F, Cl, Br, CN, heterocycloalkyl;
R 2 and R 3 are each independently R a , COR a , C(═O)OR a , or SO 2 R a ;
Y 5 , Y 6 , Y 7 , and Y 8 are each independently CR 4 , N, or O;
R 4 is R 2 , OR a , NR 2 R 3 , SR a , SOR a , SO 2 R a , SO 2 NHR a , N(R 5 )COR a , halogen, trihalomethyl, CN, S═O, or nitro;
each R 5 is independently R a , COR a , SO 2 R a , or is not present;
W 1 and W 2 are each independently, O, S, NH, or CH 2 ;
each R x is independently O, S, CR 2 R 3 , or NR 5 ;
R y is S, N—CN, or CHR 4 ;
R z is R b , OR b , SR b , COR b , CO 2 R b , OCOR b , NR b R c , CON b R c , NR b COR c , SO 2 NR b R c , CF 3 , CN, NO 2 , F, Cl, Br, I, or C 2-5 heterocyclyl;
each R b is independently H or C 1-3 hydrocarbyl, and each R c is independently H or C 1-3 alkyl; and
Z 1 and Z 2 are each independently C or N.
41 . The method of claim 40 , wherein the eukaryotic cell is in viva
42 . The method of claim 40 , wherein the eukaryotic cell is in vitro.Join the waitlist — get patent alerts
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