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 US20130129677A1 (en) | 2009-02-27 | 2012-12-07 | Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections |
| US13/708,224 | 2012-12-07 | ||
| PCT/US2013/073449 WO2014089378A1 (en) | 2012-12-07 | 2013-12-06 | Thienopyridine derivatives for the treatment and prevention of dengue virus infections |
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| JP2016501883A JP2016501883A (ja) | 2016-01-21 |
| JP2016501883A5 true JP2016501883A5 (enExample) | 2016-11-17 |
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| JP (1) | JP2016501883A (enExample) |
| CA (1) | CA2893318A1 (enExample) |
| WO (1) | WO2014089378A1 (enExample) |
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| 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 |
| US10689394B2 (en) | 2016-06-14 | 2020-06-23 | The University Of Tokyo | Thieno[2,3-b]pyridine derivative, quinoline derivative, and use thereof |
| AU2018361971A1 (en) * | 2017-11-03 | 2020-06-04 | Universite De Montreal | Compounds and use thereof in the expansion of stem cells and/or progenitor cells |
| US20210230179A1 (en) * | 2018-06-06 | 2021-07-29 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Thieno[2,3-b]pyridine derivatives as epac inhibitors and their pharmaceutical uses |
| US20220332720A1 (en) * | 2019-08-21 | 2022-10-20 | 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)
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| AU3533095A (en) * | 1994-09-22 | 1996-04-09 | Rational Drug Design Laboratories | Arylthiadiazole derivative and antiviral agent containing the same |
| 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 |
| AU2007254165A1 (en) * | 2006-05-17 | 2007-11-29 | Forschungsverbund Berlin E.V. | Pyrimidine low molecular weight ligands for modulating hormone receptors |
| US20130129677A1 (en) * | 2009-02-27 | 2013-05-23 | Siga Technologies, Inc. | Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections |
| AP3069A (en) * | 2009-02-27 | 2014-12-31 | Siga Technologies Inc | Thienopyridine derivatives for the treatment and prvention of dengue virus infection |
| US8785499B2 (en) * | 2009-07-10 | 2014-07-22 | University Of Maryland, Baltimore | Targeting NAD biosynthesis in bacterial pathogens |
-
2013
- 2013-12-06 WO PCT/US2013/073449 patent/WO2014089378A1/en not_active Ceased
- 2013-12-06 CA CA2893318A patent/CA2893318A1/en not_active Abandoned
- 2013-12-06 EP EP13859644.0A patent/EP2928470A4/en not_active Withdrawn
- 2013-12-06 JP JP2015545858A patent/JP2016501883A/ja active Pending
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