CA2893318A1

CA2893318A1 - Thienopyridine derivatives for the treatment and prevention of dengue virus infections

Thienopyridine derivatives for the treatment and prevention of dengue virus infections Download PDF

Info

Publication number: CA2893318A1
Authority: CA; Canada
Prior art keywords: amino; thieno; pyridine; carboxamide; phenyl
Prior art date: 2012-12-07
Legal status : Abandoned

Application number

CA2893318A

Other languages

English (en)

French (fr)

Inventor

Dongcheng Dai

James R. Burgeson

Shanthakumar R. Tyavanagimatt

Chelsea M. Byrd

Dennis E. Hruby

Current Assignee

Siga Technologies Inc

Original Assignee

Siga Technologies Inc

Priority date

2012-12-07

Filing date

2013-12-06

Publication date

2014-06-12

2012-12-07 Priority claimed from US13/708,224 external-priority patent/US20130129677A1/en

2013-12-06 Application filed by Siga Technologies Inc filed Critical Siga Technologies Inc

2014-06-12 Publication of CA2893318A1 publication Critical patent/CA2893318A1/en

Status Abandoned legal-status Critical Current

Links

238000011282 treatment Methods 0.000 title claims abstract description 26
206010012310 Dengue fever Diseases 0.000 title claims description 94
208000025729 dengue disease Diseases 0.000 title claims description 76
230000002265 prevention Effects 0.000 title description 3
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 214
-1 thienopyridine derivative compounds Chemical class 0.000 claims abstract description 119
238000000034 method Methods 0.000 claims abstract description 89
241000725619 Dengue virus Species 0.000 claims abstract description 33
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
230000009385 viral infection Effects 0.000 claims abstract description 9
208000036142 Viral infection Diseases 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 145
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 111
125000003118 aryl group Chemical group 0.000 claims description 93
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 84
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 81
125000001072 heteroaryl group Chemical group 0.000 claims description 79
208000001490 Dengue Diseases 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 49
125000002252 acyl group Chemical group 0.000 claims description 45
125000003342 alkenyl group Chemical group 0.000 claims description 45
125000000753 cycloalkyl group Chemical group 0.000 claims description 45
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 42
125000005251 aryl acyl group Chemical group 0.000 claims description 42
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 42
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 42
125000005253 heteroarylacyl group Chemical group 0.000 claims description 42
125000000304 alkynyl group Chemical group 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 41
125000003710 aryl alkyl group Chemical group 0.000 claims description 34
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
208000009714 Severe Dengue Diseases 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 29
229910052799 carbon Inorganic materials 0.000 claims description 26
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
125000005241 heteroarylamino group Chemical group 0.000 claims description 22
125000004442 acylamino group Chemical group 0.000 claims description 21
125000001769 aryl amino group Chemical group 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
201000002950 dengue hemorrhagic fever Diseases 0.000 claims description 21
125000005842 heteroatom Chemical group 0.000 claims description 21
241000124008 Mammalia Species 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 19
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 19
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 19
125000004663 dialkyl amino group Chemical group 0.000 claims description 19
125000005553 heteroaryloxy group Chemical group 0.000 claims description 19
229960005486 vaccine Drugs 0.000 claims description 18
125000001931 aliphatic group Chemical group 0.000 claims description 17
125000004104 aryloxy group Chemical group 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000004423 acyloxy group Chemical group 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 12
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 11
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 11
125000005110 aryl thio group Chemical group 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 11
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
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 description 10
239000003443 antiviral agent Substances 0.000 claims description 10
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 description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
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 description 8
102000014150 Interferons Human genes 0.000 claims description 8
108010050904 Interferons Proteins 0.000 claims description 8
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
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 description 6
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 description 5
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 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
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 description 4
238000011260 co-administration Methods 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims 10
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 6
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 6
229940079322 interferon Drugs 0.000 claims 6
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 4
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 4
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 3
IPXYPQNRIHCBBT-UHFFFAOYSA-N 2-thiophen-2-yl-10-[3-(trifluoromethyl)phenyl]-7,8-dihydro-5h-pyrido[2,3]thieno[2,4-d][1,5]diazonine-6,9,11-trione Chemical compound FC(F)(F)C1=CC=CC(N2C(C3=C(C4=CC=C(N=C4S3)C=3SC=CC=3)NC(=O)CCC2=O)=O)=C1 IPXYPQNRIHCBBT-UHFFFAOYSA-N 0.000 claims 3
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 3
FQJQNKYIZYNAHZ-UHFFFAOYSA-N 3-(n-[3-amino-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carbonyl]-4-chloroanilino)propanoic acid Chemical compound C=1C=C2C(N)=C(C(=O)N(CCC(O)=O)C=3C=CC(Cl)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 FQJQNKYIZYNAHZ-UHFFFAOYSA-N 0.000 claims 3
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 3
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 3
QXUIHCAEJBKALB-UHFFFAOYSA-N 3-amino-4-methyl-n-(5-phenyl-1,3,4-thiadiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound NC=1C=2C(C)=CC=NC=2SC=1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 QXUIHCAEJBKALB-UHFFFAOYSA-N 0.000 claims 3
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 3
YAMPVXYBSZVZNL-UHFFFAOYSA-N 3-amino-5-methyl-n-(5-phenyl-1,3,4-thiadiazol-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound NC=1C2=CC(C)=CN=C2SC=1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 YAMPVXYBSZVZNL-UHFFFAOYSA-N 0.000 claims 3
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 3
MDMFZCQYRTZOBG-UHFFFAOYSA-N 3-amino-6-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[3-(trifluoromethyl)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C(C)=NC(C)=C1C1=CC=C(C(N)=C(S2)C(=O)NC=3C=C(C=CC=3)C(F)(F)F)C2=N1 MDMFZCQYRTZOBG-UHFFFAOYSA-N 0.000 claims 3
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 3
MPLAXMJMWCHYCS-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(2,5-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C(=CC=C(Cl)C=3)Cl)SC2=NC=1C1=CC=C(Cl)C=C1 MPLAXMJMWCHYCS-UHFFFAOYSA-N 0.000 claims 3
JYNJRAVEYDAEIM-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(3,4-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=C(Cl)C(Cl)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 JYNJRAVEYDAEIM-UHFFFAOYSA-N 0.000 claims 3
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 3
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 3
VBNGRQWGAKKUNY-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(5-chloropyridin-2-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3N=CC(Cl)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 VBNGRQWGAKKUNY-UHFFFAOYSA-N 0.000 claims 3
GVLWWNSSPZCFPO-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-(6-chloropyridin-3-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=NC(Cl)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 GVLWWNSSPZCFPO-UHFFFAOYSA-N 0.000 claims 3
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 3
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 3
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 3
ZODGXOCXCDWHMX-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-n-[4-(difluoromethyl)phenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C=CC(=CC=3)C(F)F)SC2=NC=1C1=CC=C(Cl)C=C1 ZODGXOCXCDWHMX-UHFFFAOYSA-N 0.000 claims 3
HNJZUZAOXQXPRI-UHFFFAOYSA-N 3-amino-6-(4-chlorophenyl)-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=C(Cl)C=C1 HNJZUZAOXQXPRI-UHFFFAOYSA-N 0.000 claims 3
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 3
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 3
UKHXBJBAFYSLDS-UHFFFAOYSA-N 3-amino-6-methyl-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-7,8-dihydro-5h-thieno[2,3-b][1,6]naphthyridine-2-carboxamide Chemical compound NC=1C=2C=C3CN(C)CCC3=NC=2SC=1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 UKHXBJBAFYSLDS-UHFFFAOYSA-N 0.000 claims 3
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 3
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 3
RJFUSXJFOTURBD-UHFFFAOYSA-N 3-amino-n-(2-bromophenyl)-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3C(=CC=CC=3)Br)SC2=NC=1C1=CC=C(Cl)C=C1 RJFUSXJFOTURBD-UHFFFAOYSA-N 0.000 claims 3
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 3
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 3
QMMAZEFRMSTWIP-UHFFFAOYSA-N 3-amino-n-(4-bromophenyl)-6-(5-chloropyridin-2-yl)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=N1 QMMAZEFRMSTWIP-UHFFFAOYSA-N 0.000 claims 3
OVOGJEBYVKQGFY-UHFFFAOYSA-N 3-amino-n-(5-bromopyridin-2-yl)-6-(4-chlorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(N)=C(C(=O)NC=3N=CC(Br)=CC=3)SC2=NC=1C1=CC=C(Cl)C=C1 OVOGJEBYVKQGFY-UHFFFAOYSA-N 0.000 claims 3
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