JP2016501883A5 - - Google Patents
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- JP2016501883A5 JP2016501883A5 JP2015545858A JP2015545858A JP2016501883A5 JP 2016501883 A5 JP2016501883 A5 JP 2016501883A5 JP 2015545858 A JP2015545858 A JP 2015545858A JP 2015545858 A JP2015545858 A JP 2015545858A JP 2016501883 A5 JP2016501883 A5 JP 2016501883A5
- Authority
- JP
- Japan
- Prior art keywords
- thieno
- amino
- pyridine
- carboxamide
- phenyl
- 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.)
- Pending
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- -1 isocyano, nitro, amino Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005251 aryl acyl group Chemical group 0.000 claims 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims 4
- 125000005253 heteroarylacyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 206010012310 Dengue fever Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000025729 dengue disease Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- XNTAESPDXNOSPE-UHFFFAOYSA-N 3-amino-n,6-bis(4-chlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(Cl)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 XNTAESPDXNOSPE-UHFFFAOYSA-N 0.000 claims 2
- MPYDTAKQTJCYMA-UHFFFAOYSA-N 3-amino-n-(4-bromophenyl)-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(Br)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 MPYDTAKQTJCYMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims 1
- LCFGVXANCKUZJX-UHFFFAOYSA-N 2-[n-(3-amino-6-thiophen-2-ylthieno[2,3-b]pyridine-2-carbonyl)-3-(trifluoromethyl)anilino]acetic acid Chemical compound C=1C=C2C(N)=C(C(=O)N(CC(O)=O)C=3C=C(C=CC=3)C(F)(F)F)SC2=NC=1C1=CC=CS1 LCFGVXANCKUZJX-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- MCDIZEGYBFVWOK-UHFFFAOYSA-N 3,5-diamino-n-(5-phenyl-1,3,4-thiadiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C2=NC=C(N)C=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 MCDIZEGYBFVWOK-UHFFFAOYSA-N 0.000 claims 1
- VUKUIZBMXWMXFX-UHFFFAOYSA-N 3-(n-[3-amino-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carbonyl]-4-bromoanilino)propanoic acid Chemical compound C=1C=C2C(N)=C(C(=O)N(CCC(O)=O)C=3C=CC(Br)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 VUKUIZBMXWMXFX-UHFFFAOYSA-N 0.000 claims 1
- SNFGEKZZSGJGBG-UHFFFAOYSA-N 3-[n-(3-amino-6-thiophen-2-ylthieno[2,3-b]pyridine-2-carbonyl)-3-(trifluoromethyl)anilino]propanoic acid Chemical compound C=1C=C2C(N)=C(C(=O)N(CCC(O)=O)C=3C=C(C=CC=3)C(F)(F)F)SC2=NC=1C1=CC=CS1 SNFGEKZZSGJGBG-UHFFFAOYSA-N 0.000 claims 1
- HOKLVNXVCQSSAN-UHFFFAOYSA-N 3-[n-[3-amino-6-(3-methoxyphenyl)thieno[2,3-b]pyridine-2-carbonyl]-4-(trifluoromethoxy)anilino]propanoic acid Chemical compound COC1=CC=CC(C=2N=C3SC(=C(N)C3=CC=2)C(=O)N(CCC(O)=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1 HOKLVNXVCQSSAN-UHFFFAOYSA-N 0.000 claims 1
- NDGVXZHIZIUDQQ-UHFFFAOYSA-N 3-amino-2-[(5-phenyl-1,3,4-thiadiazol-2-yl)carbamoyl]thieno[2,3-b]pyridine-5-carboxylic acid Chemical compound S1C2=NC=C(C(O)=O)C=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 NDGVXZHIZIUDQQ-UHFFFAOYSA-N 0.000 claims 1
- MXLZVYYKPDMFBB-UHFFFAOYSA-N 3-amino-4-methoxy-n-(5-phenyl-1,3,4-thiadiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound NC=1C=2C(OC)=CC=NC=2SC=1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 MXLZVYYKPDMFBB-UHFFFAOYSA-N 0.000 claims 1
- ZGMWBQBYKMJQOB-UHFFFAOYSA-N 3-amino-5-hydroxy-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-6,7,8,9-tetrahydro-5h-cyclohepta[b]thieno[3,2-e]pyridine-2-carboxamide Chemical compound S1C2=NC=3CCCCC(O)C=3C=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 ZGMWBQBYKMJQOB-UHFFFAOYSA-N 0.000 claims 1
- CKYUFAYVYUXPJA-UHFFFAOYSA-N 3-amino-5-oxo-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-6,7,8,9-tetrahydro-5h-cyclohepta[b]thieno[3,2-e]pyridine-2-carboxamide Chemical compound S1C2=NC=3CCCCC(=O)C=3C=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 CKYUFAYVYUXPJA-UHFFFAOYSA-N 0.000 claims 1
- KNOXMIMQBHGUMQ-UHFFFAOYSA-N 3-amino-6-(1,3-benzodioxol-5-yl)-n-(2-bromo-4-methylphenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound BrC1=CC(C)=CC=C1NC(=O)C1=C(N)C2=CC=C(C=3C=C4OCOC4=CC=3)N=C2S1 KNOXMIMQBHGUMQ-UHFFFAOYSA-N 0.000 claims 1
- JPNLDJUBHQCXBA-UHFFFAOYSA-N 3-amino-6-(3-methoxyphenyl)-n-[4-(trifluoromethoxy)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound COC1=CC=CC(C=2N=C3SC(=C(N)C3=CC=2)C(=O)NC=2C=CC(OC(F)(F)F)=CC=2)=C1 JPNLDJUBHQCXBA-UHFFFAOYSA-N 0.000 claims 1
- LHSDGLRNODSUHS-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(2,3-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C(=C(Cl)C=CC=3)Cl)SC2=NC=1C1=CC=C(Cl)C=C1 LHSDGLRNODSUHS-UHFFFAOYSA-N 0.000 claims 1
- AIRAIJSHUNKACH-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(3,4-dimethylphenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=C(N)C2=CC=C(C=3C=CC(Cl)=CC=3)N=C2S1 AIRAIJSHUNKACH-UHFFFAOYSA-N 0.000 claims 1
- SCIZKGYHKPMVJA-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(4-hydroxyphenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(O)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 SCIZKGYHKPMVJA-UHFFFAOYSA-N 0.000 claims 1
- QHEFGRKZJVYUNP-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-[4-(1,1-difluoroethyl)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(C(F)(F)C)=CC=C1NC(=O)C1=C(N)C2=CC=C(C=3C=CC(Cl)=CC=3)N=C2S1 QHEFGRKZJVYUNP-UHFFFAOYSA-N 0.000 claims 1
- RYXOLLQLNXXYKS-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-[4-(2,2,2-trifluoroacetyl)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(=CC=3)C(=O)C(F)(F)F)SC2=NC=1C1=CC=C(Cl)C=C1 RYXOLLQLNXXYKS-UHFFFAOYSA-N 0.000 claims 1
- QNRUSQOBAHFIEE-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-[4-(difluoromethoxy)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(OC(F)F)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 QNRUSQOBAHFIEE-UHFFFAOYSA-N 0.000 claims 1
- CFRWNHJFWJWWDG-UHFFFAOYSA-N 3-amino-6-(trifluoromethyl)-n-[3-(trifluoromethyl)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C2=NC(C(F)(F)F)=CC=C2C(N)=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 CFRWNHJFWJWWDG-UHFFFAOYSA-N 0.000 claims 1
- HYYKFLNLVBEYPL-UHFFFAOYSA-N 3-amino-6-[3-(difluoromethoxy)phenyl]-n-[4-(difluoromethoxy)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(OC(F)F)=CC=3)SC2=NC=1C1=CC=CC(OC(F)F)=C1 HYYKFLNLVBEYPL-UHFFFAOYSA-N 0.000 claims 1
- CUMDBGFMCPBWQP-UHFFFAOYSA-N 3-amino-6-[3-(difluoromethoxy)phenyl]-n-[4-(trifluoromethoxy)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(OC(F)(F)F)=CC=3)SC2=NC=1C1=CC=CC(OC(F)F)=C1 CUMDBGFMCPBWQP-UHFFFAOYSA-N 0.000 claims 1
- WVNUJGBJACCANV-UHFFFAOYSA-N 3-amino-6-[3-(trifluoromethoxy)phenyl]-n-[4-(trifluoromethoxy)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(OC(F)(F)F)=CC=3)SC2=NC=1C1=CC=CC(OC(F)(F)F)=C1 WVNUJGBJACCANV-UHFFFAOYSA-N 0.000 claims 1
- KMZMTCNWFUJBNJ-UHFFFAOYSA-N 3-amino-6-chloro-n-(5-phenyl-1,3,4-thiadiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C2=NC(Cl)=CC=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 KMZMTCNWFUJBNJ-UHFFFAOYSA-N 0.000 claims 1
- HHYFXDUSKRMHCQ-UHFFFAOYSA-N 3-amino-6-methyl-n-(5-phenyl-1,3,4-thiadiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C2=NC(C)=CC=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 HHYFXDUSKRMHCQ-UHFFFAOYSA-N 0.000 claims 1
- ITSKGMKPRYFWAL-UHFFFAOYSA-N 3-amino-6-thiophen-2-yl-n'-[3-(trifluoromethyl)phenyl]thieno[2,3-b]pyridine-2-carboximidamide Chemical compound C=1C=C2C(N)=C(C(=N)NC=3C=C(C=CC=3)C(F)(F)F)SC2=NC=1C1=CC=CS1 ITSKGMKPRYFWAL-UHFFFAOYSA-N 0.000 claims 1
- HCNPMXXHNSGZIL-UHFFFAOYSA-N 3-amino-n-(3-chlorophenyl)-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=C(Cl)C=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 HCNPMXXHNSGZIL-UHFFFAOYSA-N 0.000 claims 1
- WCKRWUUQCCSAKL-UHFFFAOYSA-N 3-amino-n-(4-bromophenyl)-5-cyano-4-(furan-2-yl)-6-oxo-7h-thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=12C(N)=C(C(=O)NC=3C=CC(Br)=CC=3)SC2=NC(O)=C(C#N)C=1C1=CC=CO1 WCKRWUUQCCSAKL-UHFFFAOYSA-N 0.000 claims 1
- BXDYNMJWHMRNSX-UHFFFAOYSA-N 3-amino-n-(4-bromophenyl)-6-(3-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound COC1=CC=CC(C=2N=C3SC(=C(N)C3=CC=2)C(=O)NC=2C=CC(Br)=CC=2)=C1 BXDYNMJWHMRNSX-UHFFFAOYSA-N 0.000 claims 1
- SXPPZGHBPQOEFB-UHFFFAOYSA-N 3-amino-n-methyl-6-thiophen-2-yl-n-[3-(trifluoromethyl)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1N(C)C(=O)C(=C(C1=CC=2)N)SC1=NC=2C1=CC=CS1 SXPPZGHBPQOEFB-UHFFFAOYSA-N 0.000 claims 1
- FXTSYHIBGLLDBP-UHFFFAOYSA-N 4-[[3-amino-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carbonyl]amino]benzenesulfonic acid Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(=CC=3)S(O)(=O)=O)SC2=NC=1C1=CC=C(Cl)C=C1 FXTSYHIBGLLDBP-UHFFFAOYSA-N 0.000 claims 1
- JZGXAEVJGRCVBU-UHFFFAOYSA-N 4-[[3-amino-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carbonyl]amino]benzoic acid Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(=CC=3)C(O)=O)SC2=NC=1C1=CC=C(Cl)C=C1 JZGXAEVJGRCVBU-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- YWRIATFFDFUQCS-UHFFFAOYSA-N 6-amino-10-fluoro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-thia-2-azatricyclo[7.5.0.03,7]tetradeca-1(9),2,5,7-tetraene-5-carboxamide Chemical compound S1C2=NC=3CCCCC(F)C=3C=C2C(N)=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 YWRIATFFDFUQCS-UHFFFAOYSA-N 0.000 claims 1
- SKIOPINUHKJQNC-UHFFFAOYSA-N 6-amino-N-butyl-4-thia-2-azatricyclo[7.5.0.03,7]tetradeca-1,3(7),5,8-tetraene-5-carboxamide Chemical compound C1CCCCC2=C1N=C1SC(C(=O)NCCCC)=C(N)C1=C2 SKIOPINUHKJQNC-UHFFFAOYSA-N 0.000 claims 1
- JECJMCIQCXXWFM-UHFFFAOYSA-N 6-amino-N-cyclohexyl-4-thia-2-azatricyclo[7.5.0.03,7]tetradeca-1,3(7),5,8-tetraene-5-carboxamide Chemical compound S1C2=NC=3CCCCCC=3C=C2C(N)=C1C(=O)NC1CCCCC1 JECJMCIQCXXWFM-UHFFFAOYSA-N 0.000 claims 1
- XAKFZIQEDWJGJW-UHFFFAOYSA-N 6-amino-N-tert-butyl-4-thia-2-azatricyclo[7.5.0.03,7]tetradeca-1,3(7),5,8-tetraene-5-carboxamide Chemical compound C1CCCCC2=C1N=C1SC(C(=O)NC(C)(C)C)=C(N)C1=C2 XAKFZIQEDWJGJW-UHFFFAOYSA-N 0.000 claims 1
- PDFMOOJJTZAUJW-UHFFFAOYSA-N 7-thiophen-2-yl-3-[3-(trifluoromethyl)phenyl]-1h-pyrido[2,3]thieno[2,4-b]pyrimidine-2,4-dione Chemical compound FC(F)(F)C1=CC=CC(N2C(C=3SC4=NC(=CC=C4C=3NC2=O)C=2SC=CC=2)=O)=C1 PDFMOOJJTZAUJW-UHFFFAOYSA-N 0.000 claims 1
- XKKXSBRHLNKTRI-UHFFFAOYSA-N 8-thiophen-2-yl-4-[3-(trifluoromethyl)phenyl]-1,3-dihydropyrido[2,3]thieno[2,4-d][1,4]diazepine-2,5-dione Chemical compound FC(F)(F)C1=CC=CC(N2C(C3=C(C4=CC=C(N=C4S3)C=3SC=CC=3)NC(=O)C2)=O)=C1 XKKXSBRHLNKTRI-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000001490 Dengue Diseases 0.000 claims 1
- 241000725619 Dengue virus Species 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 208000009714 Severe Dengue Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 201000002950 dengue hemorrhagic fever Diseases 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- RXGHULSMJIVVTA-UHFFFAOYSA-N thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(=O)N)=CC2=C1 RXGHULSMJIVVTA-UHFFFAOYSA-N 0.000 claims 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/708,224 | 2012-12-07 | ||
| US13/708,224 US20130129677A1 (en) | 2009-02-27 | 2012-12-07 | Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections |
| PCT/US2013/073449 WO2014089378A1 (en) | 2012-12-07 | 2013-12-06 | Thienopyridine derivatives for the treatment and prevention of dengue virus infections |
Publications (2)
| Publication Number | Publication Date |
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| JP2016501883A JP2016501883A (ja) | 2016-01-21 |
| JP2016501883A5 true JP2016501883A5 (enrdf_load_stackoverflow) | 2016-11-17 |
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Family Applications (1)
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| JP2015545858A Pending JP2016501883A (ja) | 2012-12-07 | 2013-12-06 | デングウイルス感染症の治療及び予防のためのチエノピリジン誘導体 |
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| EP (1) | EP2928470A4 (enrdf_load_stackoverflow) |
| JP (1) | JP2016501883A (enrdf_load_stackoverflow) |
| CA (1) | CA2893318A1 (enrdf_load_stackoverflow) |
| WO (1) | WO2014089378A1 (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418635A (zh) * | 2015-12-25 | 2016-03-23 | 上海应用技术学院 | 一种噻吩并吡啶类医药中间体的合成方法 |
| CN105769866B (zh) * | 2016-03-31 | 2018-05-04 | 南通江海港建设工程有限公司 | 一种化合物在增加血小板浓度药物中的用途 |
| CN105832734B (zh) * | 2016-03-31 | 2018-05-04 | 南通江海港建设工程有限公司 | 一种化合物在增加血小板浓度药物中的用途 |
| JP7041877B2 (ja) * | 2016-06-14 | 2022-03-25 | 国立大学法人 東京大学 | チエノ［２，３－ｂ］ピリジン誘導体およびキノリン誘導体ならびにそれらの使用 |
| EP3704126A4 (en) | 2017-11-03 | 2020-12-09 | Université de Montréal | COMPOUNDS AND THEIR USE IN THE EXPANSION OF STEM CELLS AND / OR PROGENITOR CELLS |
| JP7445609B2 (ja) * | 2018-06-06 | 2024-03-07 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | Ｅｐａｃ阻害剤としてのチエノ［２，３－ｂ］ピリジン誘導体及びその医薬用途 |
| WO2021035258A1 (en) * | 2019-08-21 | 2021-02-25 | The Scripps Research Institute | Bicyclic agonists of stimulator of interferon genes sting |
| CN111072463A (zh) * | 2019-12-03 | 2020-04-28 | 辽宁凯莱英医药化学有限公司 | 一种4-乙氧基-1,1,1-三氟-3-丁烯-2-酮的连续化合成方法 |
| WO2021108999A1 (zh) * | 2019-12-03 | 2021-06-10 | 辽宁凯莱英医药化学有限公司 | 一种4-乙氧基-1,1,1-三氟-3-丁烯-2-酮的连续化合成方法 |
| WO2021250231A1 (en) * | 2020-06-12 | 2021-12-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Thienopyridine derivatives for use in the treatment of coronavirus infection |
| WO2022094816A1 (en) * | 2020-11-04 | 2022-05-12 | Janssen Pharmaceuticals, Inc. | Solid formulation |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0785193A4 (en) * | 1994-09-22 | 2000-04-19 | Rational Drug Design Lab | ARYLTHIADIAZOLE DERIVATIVES AND ANTIVIRAL PRODUCTS CONTAINING THEM |
| GB9717576D0 (en) * | 1997-08-19 | 1997-10-22 | Xenova Ltd | Pharmaceutical compounds |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US7202363B2 (en) * | 2003-07-24 | 2007-04-10 | Abbott Laboratories | Thienopyridine and furopyridine kinase inhibitors |
| AR048669A1 (es) * | 2004-03-03 | 2006-05-17 | Syngenta Ltd | Derivados biciclicos de bisamida |
| SE0403171D0 (sv) * | 2004-12-23 | 2004-12-23 | Astrazeneca Ab | New compounds |
| JP2006298909A (ja) * | 2005-03-25 | 2006-11-02 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| JP2009537551A (ja) * | 2006-05-17 | 2009-10-29 | アメリカ合衆国 | ホルモン受容体を調節するためのピリミジン低分子量リガンド |
| US20130129677A1 (en) * | 2009-02-27 | 2013-05-23 | Siga Technologies, Inc. | Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections |
| EP2400845B1 (en) * | 2009-02-27 | 2017-02-22 | Siga Technologies, Inc. | Thienopyridine derivatives for the treatment and prevention of dengue virus infections |
| US8785499B2 (en) * | 2009-07-10 | 2014-07-22 | University Of Maryland, Baltimore | Targeting NAD biosynthesis in bacterial pathogens |
-
2013
- 2013-12-06 JP JP2015545858A patent/JP2016501883A/ja active Pending
- 2013-12-06 WO PCT/US2013/073449 patent/WO2014089378A1/en active Application Filing
- 2013-12-06 CA CA2893318A patent/CA2893318A1/en not_active Abandoned
- 2013-12-06 EP EP13859644.0A patent/EP2928470A4/en not_active Withdrawn
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