SK12582001A3 - 4-Oxo-4,7-dihydro-tieno[2,3-b] pyridín-5-karboxamidy ako antivírusové prostriedky, spôsob ich prípravy, medziprodukty a farmaceutická kompozícia - Google Patents

Info

Publication number

SK12582001A3

SK12582001A3 SK1258-2001A SK12582001A SK12582001A3 SK 12582001 A3 SK12582001 A3 SK 12582001A3 SK 12582001 A SK12582001 A SK 12582001A SK 12582001 A3 SK12582001 A3 SK 12582001A3

Authority

SK

Slovakia

Prior art keywords

pyridine

chlorobenzyl

oxo

carboxamide

dihydrothieno

Prior art date

1999-03-09

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• 239000003443 antiviral agent Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 228
• 238000000034 method Methods 0.000 claims abstract description 27
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 208000029433 Herpesviridae infectious disease Diseases 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 5
• -1 cyano, phenyl Chemical group 0.000 claims description 150
• 125000000217 alkyl group Chemical group 0.000 claims description 123
• 125000000623 heterocyclic group Chemical group 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 238000006243 chemical reaction Methods 0.000 claims description 30
• 238000002360 preparation method Methods 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• TYDRNBSWYUYIDM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-iodo-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=NC=2SC(I)=CC=2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 TYDRNBSWYUYIDM-UHFFFAOYSA-N 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 11
• 150000001721 carbon Chemical group 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 150000004820 halides Chemical class 0.000 claims description 11
• GKOYKNWKHOAZMQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(3-hydroxyprop-1-ynyl)-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound S1C(C#CCO)=CC(C2=O)=C1NC=C2C(=O)NCC1=CC=C(Cl)C=C1 GKOYKNWKHOAZMQ-UHFFFAOYSA-N 0.000 claims description 11
• CFKIMGPJOCQJHM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(morpholin-4-ylmethyl)-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound C=1C=2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=NC=2SC=1CN1CCOCC1 CFKIMGPJOCQJHM-UHFFFAOYSA-N 0.000 claims description 10
• TTXWTLQWWOYSEL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(C#CCO)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 TTXWTLQWWOYSEL-UHFFFAOYSA-N 0.000 claims description 10
• 239000011734 sodium Substances 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 150000001413 amino acids Chemical class 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• RYVILUZKQWWFEK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-iodo-7-methyl-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(I)SC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 RYVILUZKQWWFEK-UHFFFAOYSA-N 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 241000282414 Homo sapiens Species 0.000 claims description 7
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 7
• 241000700605 Viruses Species 0.000 claims description 7
• OYXDVYYRIPWWRX-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(3-hydroxypropyl)-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound S1C(CCCO)=CC(C2=O)=C1NC=C2C(=O)NCC1=CC=C(Cl)C=C1 OYXDVYYRIPWWRX-UHFFFAOYSA-N 0.000 claims description 7
• QNIVWKXKELTNSR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-ethyl-2-(4-hydroxybut-1-ynyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(C#CCCO)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 QNIVWKXKELTNSR-UHFFFAOYSA-N 0.000 claims description 7
• 241001529453 unidentified herpesvirus Species 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• LBUNXHFEMJJRFZ-UHFFFAOYSA-N 2-bromo-n-[(4-chlorophenyl)methyl]-7-ethyl-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(Br)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 LBUNXHFEMJJRFZ-UHFFFAOYSA-N 0.000 claims description 6
• 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 6
• AQZVARLWSXIONB-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(3-hydroxyprop-1-ynyl)-7-methyl-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(C#CCO)SC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 AQZVARLWSXIONB-UHFFFAOYSA-N 0.000 claims description 6
• WTZJFPLSNCFCIY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-iodo-4-oxo-7-propan-2-ylthieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(I)SC=2N(C(C)C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 WTZJFPLSNCFCIY-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 229910052744 lithium Chemical group 0.000 claims description 5
• FSUGKFSNWLHIRH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(3-hydroxyprop-1-ynyl)-4-oxo-7-propan-2-ylthieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(C#CCO)SC=2N(C(C)C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 FSUGKFSNWLHIRH-UHFFFAOYSA-N 0.000 claims description 5
• FPXUZJPLKICOPN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(morpholin-4-ylmethyl)-4-oxo-7-(oxolan-2-ylmethyl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C=1C=C(CN2CCOCC2)SC=11)=O)=CN1CC1OCCC1 FPXUZJPLKICOPN-UHFFFAOYSA-N 0.000 claims description 5
• QBHWHLGYQSLBJT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxypropyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CCCO)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 QBHWHLGYQSLBJT-UHFFFAOYSA-N 0.000 claims description 5
• XQSPRDQSSXSMDL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-ethyl-2-(morpholin-4-ylmethyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CN3CCOCC3)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 XQSPRDQSSXSMDL-UHFFFAOYSA-N 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 239000011591 potassium Chemical group 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 229910052708 sodium Inorganic materials 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• IHMGMLCMCKUCRO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(3-hydroxypropyl)-4-oxo-7-propan-2-ylthieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CCCO)SC=2N(C(C)C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 IHMGMLCMCKUCRO-UHFFFAOYSA-N 0.000 claims description 4
• ZZQBEYRBJAVSPL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(morpholin-4-ylmethyl)-4-oxo-7-(pyridin-3-ylmethyl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C=1C=C(CN2CCOCC2)SC=11)=O)=CN1CC1=CC=CN=C1 ZZQBEYRBJAVSPL-UHFFFAOYSA-N 0.000 claims description 4
• PXDQYKGDLGXVAY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(morpholin-4-ylmethyl)-4-oxo-7-(pyridin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C=1C=C(CN2CCOCC2)SC=11)=O)=CN1CC1=CC=NC=C1 PXDQYKGDLGXVAY-UHFFFAOYSA-N 0.000 claims description 4
• KMPYNJRBDBIDOT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-ethyl-2-(4-hydroxybutyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CCCCO)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 KMPYNJRBDBIDOT-UHFFFAOYSA-N 0.000 claims description 4
• IPOPJBFUMJIEDZ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-ethyl-2-iodo-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(I)SC=2N(CC)C=C1C(=O)NCC1=CC=C(Cl)C=C1 IPOPJBFUMJIEDZ-UHFFFAOYSA-N 0.000 claims description 4
• WRWZKICFIPWGNY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-methyl-2-(morpholin-4-ylmethyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CN3CCOCC3)SC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 WRWZKICFIPWGNY-UHFFFAOYSA-N 0.000 claims description 4
• ZWIAIZZFWLQKDV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-methyl-4-oxo-2-(thiomorpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CN3CCSCC3)SC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 ZWIAIZZFWLQKDV-UHFFFAOYSA-N 0.000 claims description 4
• UXJWAKJDIPNXQP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-7-methyl-2-(morpholin-4-ylmethyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(CN3CCOCC3)SC=2N(C)C=C1C(=O)NCC1=CC=C(F)C=C1 UXJWAKJDIPNXQP-UHFFFAOYSA-N 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 229920002554 vinyl polymer Polymers 0.000 claims description 4
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
• SZBJQTYXKFRUAY-UHFFFAOYSA-N 4-methylidenemorpholin-4-ium Chemical class C=[N+]1CCOCC1 SZBJQTYXKFRUAY-UHFFFAOYSA-N 0.000 claims description 3
• DLLMBGNAEFXWEY-UHFFFAOYSA-N 7-benzyl-n-[(4-chlorophenyl)methyl]-2-(morpholin-4-ylmethyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C=1C=C(CN2CCOCC2)SC=11)=O)=CN1CC1=CC=CC=C1 DLLMBGNAEFXWEY-UHFFFAOYSA-N 0.000 claims description 3
• 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 3
• 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 241000700584 Simplexvirus Species 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• SKWQBPJZAPKQBT-UHFFFAOYSA-N diethyl 2-[[methyl-[3-[(2-methylpropan-2-yl)oxycarbonyl]-5-(morpholin-4-ylmethyl)thiophen-2-yl]amino]methylidene]propanedioate Chemical compound CC(C)(C)OC(=O)C1=C(N(C)C=C(C(=O)OCC)C(=O)OCC)SC(CN2CCOCC2)=C1 SKWQBPJZAPKQBT-UHFFFAOYSA-N 0.000 claims description 3
• YXQJWFFONNJYKF-UHFFFAOYSA-N diethyl 2-[[methyl-[3-[(2-methylpropan-2-yl)oxycarbonyl]thiophen-2-yl]amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CN(C)C=1SC=CC=1C(=O)OC(C)(C)C YXQJWFFONNJYKF-UHFFFAOYSA-N 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• RDBBFJAPMNVENH-UHFFFAOYSA-N methyl 1h-pyrazolo[4,3-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=CC=C2NN=CC2=N1 RDBBFJAPMNVENH-UHFFFAOYSA-N 0.000 claims description 3
• ONUTWHSYQHJQKS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound C=1N=C2SC(CO)=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 ONUTWHSYQHJQKS-UHFFFAOYSA-N 0.000 claims description 3
• FIPNZHXAXGJPFQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(morpholine-4-carbonyl)-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound C=1C=2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)C=NC=2SC=1C(=O)N1CCOCC1 FIPNZHXAXGJPFQ-UHFFFAOYSA-N 0.000 claims description 3
• YSVAYICQFSSTSK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=NC=2SC=CC=2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 YSVAYICQFSSTSK-UHFFFAOYSA-N 0.000 claims description 3
• BNXIDEJNZJEGHM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-(2-hydroxyethyl)-2-(3-hydroxyprop-1-ynyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound O=C1C=2C=C(C#CCO)SC=2N(CCO)C=C1C(=O)NCC1=CC=C(Cl)C=C1 BNXIDEJNZJEGHM-UHFFFAOYSA-N 0.000 claims description 3
• ILSLXJXFTGBRED-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-(2-hydroxyethyl)-2-(3-hydroxypropyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound S1C(CCCO)=CC(C2=O)=C1N(CCO)C=C2C(=O)NCC1=CC=C(Cl)C=C1 ILSLXJXFTGBRED-UHFFFAOYSA-N 0.000 claims description 3
• FZERMSMUFQAXQZ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-7-[(3-fluorophenyl)methyl]-2-(morpholin-4-ylmethyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide Chemical compound FC1=CC=CC(CN2C=3SC(CN4CCOCC4)=CC=3C(=O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=C2)=C1 FZERMSMUFQAXQZ-UHFFFAOYSA-N 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• WHOKGUYKJNAUIR-UHFFFAOYSA-N 2-[5-[(4-chlorophenyl)methylcarbamoyl]-2-(3-hydroxyprop-1-ynyl)-4-oxothieno[2,3-b]pyridin-7-yl]acetic acid Chemical compound S1C(C#CCO)=CC(C2=O)=C1N(CC(O)=O)C=C2C(=O)NCC1=CC=C(Cl)C=C1 WHOKGUYKJNAUIR-UHFFFAOYSA-N 0.000 claims description 2
• IDWLCXLNXHIPPB-UHFFFAOYSA-N 2-bromo-n-[(4-chlorophenyl)methyl]-4-oxo-7h-thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1=NC=2SC(Br)=CC=2C(O)=C1C(=O)NCC1=CC=C(Cl)C=C1 IDWLCXLNXHIPPB-UHFFFAOYSA-N 0.000 claims description 2
• 125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 2
• 108020005202 Viral DNA Proteins 0.000 claims description 2
• 230000029936 alkylation Effects 0.000 claims description 2
• 238000005804 alkylation reaction Methods 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 150000001768 cations Chemical class 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 2
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