JP2018524334A5 - - Google Patents
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- JP2018524334A5 JP2018524334A5 JP2017567099A JP2017567099A JP2018524334A5 JP 2018524334 A5 JP2018524334 A5 JP 2018524334A5 JP 2017567099 A JP2017567099 A JP 2017567099A JP 2017567099 A JP2017567099 A JP 2017567099A JP 2018524334 A5 JP2018524334 A5 JP 2018524334A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- carboxamide
- ethyl
- pyrrole
- oxoethyl
- 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.)
- Granted
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 229920001184 polypeptide Polymers 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 26
- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical compound C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000003107 substituted aryl group Chemical group 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 108090000623 proteins and genes Proteins 0.000 claims 15
- 102000004169 proteins and genes Human genes 0.000 claims 15
- 108060001084 Luciferase Proteins 0.000 claims 14
- 239000005089 Luciferase Substances 0.000 claims 14
- 241001443978 Oplophorus Species 0.000 claims 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- -1 halo-C 1- C 8 -alkyl Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 8
- 239000000758 substrate Substances 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- HXDZFDPEVAJTAH-UHFFFAOYSA-N 4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)N)SC=C2)=O)C=1C=C(C=CC=1)C HXDZFDPEVAJTAH-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 108020001507 fusion proteins Proteins 0.000 claims 5
- 102000037865 fusion proteins Human genes 0.000 claims 5
- 238000004020 luminiscence type Methods 0.000 claims 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 5
- 150000003053 piperidines Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 4
- 230000003993 interaction Effects 0.000 claims 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 4
- 102000040430 polynucleotide Human genes 0.000 claims 4
- 108091033319 polynucleotide Proteins 0.000 claims 4
- 239000002157 polynucleotide Substances 0.000 claims 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000000225 bioluminescence resonance energy transfer Methods 0.000 claims 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 2
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 claims 2
- 150000003235 pyrrolidines Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims 1
- WIHPCPCFGMCPLJ-UHFFFAOYSA-N 4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]-N-(3-morpholin-4-ylpropyl)thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)NCCCN1CCOCC1)SC=C2)=O)C=1C=C(C=CC=1)C WIHPCPCFGMCPLJ-UHFFFAOYSA-N 0.000 claims 1
- OWXVQMMHXZXPSG-UHFFFAOYSA-N 4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]-N-(pyridin-4-ylmethyl)thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)NCC1=CC=NC=C1)SC=C2)=O)C=1C=C(C=CC=1)C OWXVQMMHXZXPSG-UHFFFAOYSA-N 0.000 claims 1
- LVFNMXNIMKTADG-UHFFFAOYSA-N 4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]-N-methylthieno[3,2-b]pyrrole-5-carboxamide Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)NC)SC=C2)=O)C=1C=C(C=CC=1)C LVFNMXNIMKTADG-UHFFFAOYSA-N 0.000 claims 1
- BYXNILNGZZKILV-UHFFFAOYSA-N 4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]-N-phenylthieno[3,2-b]pyrrole-5-carboxamide Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)NC1=CC=CC=C1)SC=C2)=O)C=1C=C(C=CC=1)C BYXNILNGZZKILV-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- VNABWENKKUWHCM-UHFFFAOYSA-N BrCC=1C=C(C=CC1)N(C(CN1C2=C(C=C1C(=O)N)SC=C2)=O)CC Chemical compound BrCC=1C=C(C=CC1)N(C(CN1C2=C(C=C1C(=O)N)SC=C2)=O)CC VNABWENKKUWHCM-UHFFFAOYSA-N 0.000 claims 1
- HUEZRBYBYGQMBD-RQNOJGIXSA-N C(C)(=O)N1CCC(CC1)NC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 Chemical compound C(C)(=O)N1CCC(CC1)NC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 HUEZRBYBYGQMBD-RQNOJGIXSA-N 0.000 claims 1
- LJQZJQILPCFJTM-FBSWEULCSA-N C(C)N(C(CN1C(=CC2=CC=CC=C12)C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCCO)=O)=O)C1=CC(=CC=C1)CC Chemical compound C(C)N(C(CN1C(=CC2=CC=CC=C12)C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCCO)=O)=O)C1=CC(=CC=C1)CC LJQZJQILPCFJTM-FBSWEULCSA-N 0.000 claims 1
- ALFUCUDAUQNMQZ-YHBQERECSA-N C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NC1CCN(CC1)C)=O)SC=C2)=O)C=1C=C(C=CC=1)C Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NC1CCN(CC1)C)=O)SC=C2)=O)C=1C=C(C=CC=1)C ALFUCUDAUQNMQZ-YHBQERECSA-N 0.000 claims 1
- VADUSULEVYTMJJ-RQNOJGIXSA-N C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCC)=O)SC=C2)=O)C=1C=C(C=CC=1)C Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCC)=O)SC=C2)=O)C=1C=C(C=CC=1)C VADUSULEVYTMJJ-RQNOJGIXSA-N 0.000 claims 1
- VGIUNRLKWYVUNY-SOAUALDESA-N C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCCO)=O)SC=C2)=O)C1=CC(=CC=C1)CC Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCCO)=O)SC=C2)=O)C1=CC(=CC=C1)CC VGIUNRLKWYVUNY-SOAUALDESA-N 0.000 claims 1
- ADBPHHIMRPUPQA-RQNOJGIXSA-N C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCCO)=O)SC=C2)=O)C=1C=C(C=CC=1)C Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCCCCCO)=O)SC=C2)=O)C=1C=C(C=CC=1)C ADBPHHIMRPUPQA-RQNOJGIXSA-N 0.000 claims 1
- KLOQZVGWIWTJFY-MXVIHJGJSA-N C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCO)=O)SC=C2)=O)C=1C=C(C=CC=1)C Chemical compound C(C)N(C(CN1C2=C(C=C1C(=O)N[C@@H]1CC[C@H](CC1)C(NCCO)=O)SC=C2)=O)C=1C=C(C=CC=1)C KLOQZVGWIWTJFY-MXVIHJGJSA-N 0.000 claims 1
- QDUUMLKIZPVDBP-HZCBDIJESA-N C(CCC)NC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 Chemical compound C(CCC)NC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 QDUUMLKIZPVDBP-HZCBDIJESA-N 0.000 claims 1
- COYNLERKGMCEPW-IYARVYRRSA-N C(N)(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 Chemical compound C(N)(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 COYNLERKGMCEPW-IYARVYRRSA-N 0.000 claims 1
- LDYXBCNPMIVKQV-HCGLCNNCSA-N C1(CCCCC1)NC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 Chemical compound C1(CCCCC1)NC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 LDYXBCNPMIVKQV-HCGLCNNCSA-N 0.000 claims 1
- WFTMIJHHDICSKI-UHFFFAOYSA-N CN(C=1C=C(C=CC1)N(C(CN1C2=C(C=C1C(=O)N)SC=C2)=O)CC)C Chemical compound CN(C=1C=C(C=CC1)N(C(CN1C2=C(C=C1C(=O)N)SC=C2)=O)CC)C WFTMIJHHDICSKI-UHFFFAOYSA-N 0.000 claims 1
- WBJUGGFQEJXRLS-FBGQUBCLSA-N Cl.NCCCCCCNC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 Chemical compound Cl.NCCCCCCNC(=O)[C@@H]1CC[C@H](CC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 WBJUGGFQEJXRLS-FBGQUBCLSA-N 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 1
- QONLCXWKNZCQRN-UHFFFAOYSA-N N-cyclohexyl-4-[2-(3-methylanilino)-2-oxoethyl]thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1(CCCCC1)NC(=O)C1=CC2=C(N1CC(NC=1C=C(C=CC=1)C)=O)C=CS2 QONLCXWKNZCQRN-UHFFFAOYSA-N 0.000 claims 1
- DOXQTANEBBPXCP-UHFFFAOYSA-N N-cyclohexyl-4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1(CCCCC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 DOXQTANEBBPXCP-UHFFFAOYSA-N 0.000 claims 1
- JJBVYAOWNSLQIN-UHFFFAOYSA-N N-cyclohexyl-4-[2-(N-hexyl-3-methylanilino)-2-oxoethyl]thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1(CCCCC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CCCCCC)C=CS2 JJBVYAOWNSLQIN-UHFFFAOYSA-N 0.000 claims 1
- QOGLLHULLUXNAT-UHFFFAOYSA-N N-cyclohexyl-4-[2-[N-[2-(2-methoxyethoxy)ethyl]-3-methylanilino]-2-oxoethyl]thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1(CCCCC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CCOCCOC)C=CS2 QOGLLHULLUXNAT-UHFFFAOYSA-N 0.000 claims 1
- UMOGNUHBFRMNGN-UHFFFAOYSA-N N-cyclopentyl-4-[2-(N-ethyl-3-methylanilino)-2-oxoethyl]thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1(CCCC1)NC(=O)C1=CC2=C(N1CC(=O)N(C=1C=C(C=CC=1)C)CC)C=CS2 UMOGNUHBFRMNGN-UHFFFAOYSA-N 0.000 claims 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 claims 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
- 238000007422 luminescence assay Methods 0.000 claims 1
- ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 claims 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 238000002165 resonance energy transfer Methods 0.000 claims 1
- QWSZRRAAFHGKCH-UHFFFAOYSA-M sodium;hexane-1-sulfonate Chemical compound [Na+].CCCCCCS([O-])(=O)=O QWSZRRAAFHGKCH-UHFFFAOYSA-M 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 0 CC(*)N(*)C(*(*)CN(C(*1)C(N(*)*)=O)C2=C1CCCCCCCCCC2)=O Chemical compound CC(*)N(*)C(*(*)CN(C(*1)C(N(*)*)=O)C2=C1CCCCCCCCCC2)=O 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562184714P | 2015-06-25 | 2015-06-25 | |
| US62/184,714 | 2015-06-25 | ||
| US201562206525P | 2015-08-18 | 2015-08-18 | |
| US62/206,525 | 2015-08-18 | ||
| PCT/US2016/039307 WO2016210294A1 (en) | 2015-06-25 | 2016-06-24 | Thienopyrrole compounds and uses thereof as inhibitors of oplophorus-derived luciferases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018524334A JP2018524334A (ja) | 2018-08-30 |
| JP2018524334A5 true JP2018524334A5 (https=) | 2020-12-24 |
| JP6862368B2 JP6862368B2 (ja) | 2021-04-21 |
Family
ID=56373143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017567099A Active JP6862368B2 (ja) | 2015-06-25 | 2016-06-24 | チエノピロール化合物、及びそのＯｐｌｏｐｈｏｒｕｓ由来ルシフェラーゼの阻害剤としての使用 |
Country Status (6)
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| US (2) | US10513694B2 (https=) |
| EP (1) | EP3313846B1 (https=) |
| JP (1) | JP6862368B2 (https=) |
| CN (1) | CN107922428B (https=) |
| ES (1) | ES2809208T3 (https=) |
| WO (1) | WO2016210294A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2016210294A1 (en) | 2015-06-25 | 2016-12-29 | Promega Corporation | Thienopyrrole compounds and uses thereof as inhibitors of oplophorus-derived luciferases |
| EP3548492B1 (en) | 2016-12-01 | 2023-07-05 | Promega Corporation | Cell impermeable coelenterazine analogues |
| WO2018125992A1 (en) * | 2016-12-28 | 2018-07-05 | Promega Corporation | Functionalized nanoluc inhibitors |
| US11327072B2 (en) | 2017-02-09 | 2022-05-10 | Promega Corporation | Analyte detection immunoassay |
| JP7419260B2 (ja) | 2018-05-01 | 2024-01-22 | プロメガ コーポレイション | ＮａｎｏＬｕｃ自殺基質としてのセレンテラジン化合物 |
| EP3802514B1 (en) * | 2018-06-01 | 2022-08-03 | Promega Corporation | Inhibitors of oplophorus luciferase-derived bioluminescent complexes |
| WO2020041579A1 (en) | 2018-08-23 | 2020-02-27 | Promega Corporation | Coelenterazine analogues |
| WO2020135771A1 (zh) | 2018-12-29 | 2020-07-02 | 武汉朗来科技发展有限公司 | 杂环类化合物、中间体、其制备方法及应用 |
| KR20250085812A (ko) | 2022-10-14 | 2025-06-12 | 프로메가 코포레이션 | 코엘렌테라진 유사체 |
| US20250206747A1 (en) | 2023-12-20 | 2025-06-26 | Promega Corporation | Coelenterazine analogues |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3828535A1 (de) * | 1988-08-23 | 1990-03-08 | Basf Ag | Benzimidazol-2-carbonsaeureanilide, ihre verwendung als lichtschutzmittel fuer organisches material und mit diesen aniliden stabilisiertes organisches material |
| US5283179A (en) * | 1990-09-10 | 1994-02-01 | Promega Corporation | Luciferase assay method |
| US5340801A (en) | 1991-05-08 | 1994-08-23 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having cholecystokinin and gastrin antagonistic properties |
| GB9206757D0 (en) | 1992-03-27 | 1992-05-13 | Ferring Bv | Novel peptide receptor ligands |
| US7268229B2 (en) | 2001-11-02 | 2007-09-11 | Promega Corporation | Compounds to co-localize luminophores with luminescent proteins |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| EP1753428A4 (en) * | 2004-05-14 | 2010-09-15 | Abbott Lab | INHIBITORS OF KINASES AS THERAPEUTIC AGENTS |
| WO2006055951A2 (en) * | 2004-11-19 | 2006-05-26 | Portola Pharmaceuticals, Inc. | Tetrahydroisoquinolines as factor xa inhibitors |
| CA2627426A1 (en) | 2005-11-11 | 2007-05-18 | Markus Boehringer | Carbocyclic fused cyclic amines as inhibitors of the coagulation factor xa |
| FR2897061B1 (fr) * | 2006-02-03 | 2010-09-03 | Sanofi Aventis | Derives de n-heteroaryl-carboxamides tricycliques contenant un motif benzimidazole, leur preparation et leur application en therapeutique. |
| WO2008118445A1 (en) | 2007-03-26 | 2008-10-02 | Promega Corporation | Methods to quench light from optical reactions |
| WO2009000878A1 (en) | 2007-06-28 | 2008-12-31 | Novartis Ag | Kallikrein 7 modulators |
| US8163910B2 (en) | 2007-10-03 | 2012-04-24 | Elitech Holding B.V. | Amide-substituted xanthene dyes |
| WO2010118208A1 (en) * | 2009-04-09 | 2010-10-14 | Exelixis, Inc. | Benzoxazepin-4- (5h) -yl derivatives and their use to treat cancer |
| ES2795287T3 (es) | 2009-05-01 | 2020-11-23 | Promega Corp | Luciferasas de Oplophorus sintéticas con mayor emisión de luz |
| US20130178453A1 (en) | 2010-02-09 | 2013-07-11 | Ironwood Pharmaceuticals, Inc. | Cannabinoid Agonists |
| CN103180324A (zh) | 2010-11-02 | 2013-06-26 | 普罗美加公司 | 腔肠素衍生物及其使用方法 |
| SG10202103336SA (en) | 2010-11-02 | 2021-04-29 | Promega Corp | Novel coelenterazine substrates and methods of use |
| JP6067019B2 (ja) | 2011-09-02 | 2017-01-25 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 代謝的に活性な細胞の酸化還元状態を評価するための化合物及び方法、ならびにｎａｄ（ｐ）／ｎａｄ（ｐ）ｈを測定するための方法 |
| US20140099654A1 (en) * | 2012-09-26 | 2014-04-10 | Promega Corporation | Real-time monitoring |
| WO2015067302A1 (en) | 2013-11-05 | 2015-05-14 | Ecole Polytechnique Federale De Lausanne (Epfl) | Sensor molecules and uses thereof |
| US9790537B2 (en) | 2014-01-29 | 2017-10-17 | Promega Corporation | Quinone-masked probes as labeling reagents for cell uptake measurements |
| EP3099691B1 (en) | 2014-01-29 | 2019-11-20 | Promega Corporation | Pro-substrates for live cell applications |
| EP3304078B1 (en) | 2015-06-05 | 2022-08-31 | Promega Corporation | Cell-permeable, cell-compatible, and cleavable linkers for covalent tethering of functional elements |
| WO2016210294A1 (en) | 2015-06-25 | 2016-12-29 | Promega Corporation | Thienopyrrole compounds and uses thereof as inhibitors of oplophorus-derived luciferases |
| WO2018125992A1 (en) | 2016-12-28 | 2018-07-05 | Promega Corporation | Functionalized nanoluc inhibitors |
-
2016
- 2016-06-24 WO PCT/US2016/039307 patent/WO2016210294A1/en not_active Ceased
- 2016-06-24 CN CN201680044238.1A patent/CN107922428B/zh active Active
- 2016-06-24 EP EP16736683.0A patent/EP3313846B1/en active Active
- 2016-06-24 US US15/192,420 patent/US10513694B2/en active Active
- 2016-06-24 JP JP2017567099A patent/JP6862368B2/ja active Active
- 2016-06-24 ES ES16736683T patent/ES2809208T3/es active Active
-
2019
- 2019-11-05 US US16/674,485 patent/US20200063110A1/en not_active Abandoned
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