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 (enExample) | 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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| EP (1) | EP3313846B1 (enExample) |
| JP (1) | JP6862368B2 (enExample) |
| CN (1) | CN107922428B (enExample) |
| ES (1) | ES2809208T3 (enExample) |
| WO (1) | WO2016210294A1 (enExample) |
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| EP3313846B1 (en) | 2015-06-25 | 2020-05-06 | 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 |
| JP7161475B2 (ja) * | 2016-12-28 | 2022-10-26 | プロメガ コーポレイション | 官能化ｎａｎｏｌｕｃ阻害剤 |
| JP7141405B2 (ja) | 2017-02-09 | 2022-09-22 | プロメガ コーポレイション | 検体検出イムノアッセイ |
| EP3788048A1 (en) | 2018-05-01 | 2021-03-10 | Promega Corporation | Coelenterazine compounds as nanoluc suicide substrates |
| EP4140991B1 (en) * | 2018-06-01 | 2024-05-15 | Promega Corporation | Inhibitors of oplophorus luciferase-derived bioluminescent complexes |
| JP7653351B2 (ja) | 2018-08-23 | 2025-03-28 | プロメガ コーポレイション | セレンテラジン類似体 |
| KR102797127B1 (ko) | 2018-12-29 | 2025-04-21 | 우한 크리에이터나 사이언스 앤드 테크놀로지 컴퍼니, 리미티드 | 헤테로고리계 화합물, 중간체, 이의 제조 방법 및 용도 |
| EP4284804A1 (en) | 2021-01-26 | 2023-12-06 | Schrödinger, Inc. | Tricyclic compounds useful in the treatment of cancer, autoimmune and inflammatory disorders |
| CN120051474A (zh) | 2022-10-14 | 2025-05-27 | 普罗美加公司 | 腔肠素类似物 |
| US20250206747A1 (en) | 2023-12-20 | 2025-06-26 | Promega Corporation | Coelenterazine analogues |
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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 |
| MXPA06013250A (es) * | 2004-05-14 | 2007-02-28 | Abbott Lab | Inhibidores de quinasa como agentes terapeuticos. |
| WO2006055951A2 (en) * | 2004-11-19 | 2006-05-26 | Portola Pharmaceuticals, Inc. | Tetrahydroisoquinolines as factor xa inhibitors |
| BRPI0618523A2 (pt) * | 2005-11-11 | 2011-09-06 | Hoffmann La Roche | compostos de aminas cìclicas fundidas carbocìclicas, composições farmacêuticas e usos dos mesmos |
| 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. |
| US20080248511A1 (en) | 2007-03-26 | 2008-10-09 | Promega Corporation | Methods to quench light from optical reactions |
| BRPI0813230A2 (pt) | 2007-06-28 | 2014-12-23 | Novartis Ag | Moduladores de calicreína 7 |
| 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 |
| WO2011100359A1 (en) | 2010-02-09 | 2011-08-18 | Ironwood Pharmaceuticals, Inc. | Cannabinoid agonists |
| CN103443121B (zh) | 2010-11-02 | 2016-04-20 | 普罗梅加公司 | 新型腔肠素底物及其使用方法 |
| CA2815381C (en) | 2010-11-02 | 2019-03-19 | Promega Corporation | Coelenterazine derivatives and methods of using same |
| US9273343B2 (en) | 2011-09-02 | 2016-03-01 | Promega Corporation | Compounds and methods for assaying redox state of metabolically active cells and methods for measuring NAD(P)/NAD(P)H |
| EP2900833B1 (en) | 2012-09-26 | 2018-05-30 | 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 |
| JP6876002B2 (ja) | 2015-06-05 | 2021-05-26 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 機能的要素を共有結合により係留させるための細胞透過性、細胞適合性、かつ開裂可能であるリンカー |
| EP3313846B1 (en) | 2015-06-25 | 2020-05-06 | Promega Corporation | Thienopyrrole compounds and uses thereof as inhibitors of oplophorus-derived luciferases |
| JP7161475B2 (ja) | 2016-12-28 | 2022-10-26 | プロメガ コーポレイション | 官能化ｎａｎｏｌｕｃ阻害剤 |
-
2016
- 2016-06-24 EP EP16736683.0A patent/EP3313846B1/en active Active
- 2016-06-24 JP JP2017567099A patent/JP6862368B2/ja active Active
- 2016-06-24 US US15/192,420 patent/US10513694B2/en active Active
- 2016-06-24 WO PCT/US2016/039307 patent/WO2016210294A1/en not_active Ceased
- 2016-06-24 ES ES16736683T patent/ES2809208T3/es active Active
- 2016-06-24 CN CN201680044238.1A patent/CN107922428B/zh active Active
-
2019
- 2019-11-05 US US16/674,485 patent/US20200063110A1/en not_active Abandoned
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