JP2018080173A5 - - Google Patents
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- JP2018080173A5 JP2018080173A5 JP2017237159A JP2017237159A JP2018080173A5 JP 2018080173 A5 JP2018080173 A5 JP 2018080173A5 JP 2017237159 A JP2017237159 A JP 2017237159A JP 2017237159 A JP2017237159 A JP 2017237159A JP 2018080173 A5 JP2018080173 A5 JP 2018080173A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- phenyl
- amino
- cyano
- alkyl
- 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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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 229950011148 cyclopropane Drugs 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- -1 1-methyl-1-hydroxyethyl Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 1
- XACKYOGUISXLGB-KMRXNPHXSA-N 4-[2-[[(1'R,4S)-6-(tert-butylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]-4-cyanophenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC(C)(C)C)=O XACKYOGUISXLGB-KMRXNPHXSA-N 0.000 claims 1
- BKXLRZCBOIWRDL-DLLPINGYSA-N 4-[2-[[(1'R,4S)-6-[(1-tert-butylpyrazol-4-yl)carbamoyl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]-4-cyanophenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC=1C=NN(C=1)C(C)(C)C)=O BKXLRZCBOIWRDL-DLLPINGYSA-N 0.000 claims 1
- IWMLJVYOPVPOKM-BZWCRFLISA-N 4-[2-[[(1'R,4S)-6-[[(2S)-butan-2-yl]carbamoyl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]-4-cyanophenyl]butanoic acid Chemical compound C[C@@H](CC)NC(=O)C=1C=C2C(=CC=1)OCC[C@@]21[C@@H](C1)C(=O)NC1=C(C=CC(=C1)C#N)CCCC(=O)O IWMLJVYOPVPOKM-BZWCRFLISA-N 0.000 claims 1
- YOTUXJLJJYNCDG-CUNXSJBXSA-N 4-[4-cyano-2-[[(1'R,3R)-5-(2-methoxyethylcarbamoyl)spiro[1,2-dihydroindene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CCC2=CC=C(C=C12)C(NCCOC)=O YOTUXJLJJYNCDG-CUNXSJBXSA-N 0.000 claims 1
- XLVIQYDVJGLHGQ-CPJSRVTESA-N 4-[4-cyano-2-[[(1'R,3R)-5-(methylcarbamoyl)spiro[1,2-dihydroindene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CCC2=CC=C(C=C12)C(NC)=O XLVIQYDVJGLHGQ-CPJSRVTESA-N 0.000 claims 1
- ILHOIEZMIAPIJM-KDYSTLNUSA-N 4-[4-cyano-2-[[(1'R,3S)-1,1-dimethyl-5-(methylcarbamoyl)spiro[2H-indene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CC(C2=CC=C(C=C12)C(NC)=O)(C)C ILHOIEZMIAPIJM-KDYSTLNUSA-N 0.000 claims 1
- PCCVEUAPMPIIHS-MUAVYFROSA-N 4-[4-cyano-2-[[(1'R,3S)-5-(2-methoxyethylcarbamoyl)-1,1-dimethylspiro[2H-indene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CC(C2=CC=C(C=C12)C(NCCOC)=O)(C)C PCCVEUAPMPIIHS-MUAVYFROSA-N 0.000 claims 1
- AXEVDXXLVNIBMT-RXFWQSSRSA-N 4-[4-cyano-2-[[(1'R,3S)-5-(2-methoxyethylcarbamoyl)spiro[2H-1-benzofuran-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)COC1=C2C=C(C=C1)C(NCCOC)=O AXEVDXXLVNIBMT-RXFWQSSRSA-N 0.000 claims 1
- DWUWBBZTXMNNIZ-MHECFPHRSA-N 4-[4-cyano-2-[[(1'R,3S)-5-(methylcarbamoyl)spiro[2H-1-benzofuran-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)COC1=C2C=C(C=C1)C(NC)=O DWUWBBZTXMNNIZ-MHECFPHRSA-N 0.000 claims 1
- QQGQJASTNSSODA-WXVAWEFUSA-N 4-[4-cyano-2-[[(1'R,3S)-5-pyridin-3-ylspiro[2H-1-benzofuran-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)COC1=C2C=C(C=C1)C=1C=NC=CC=1 QQGQJASTNSSODA-WXVAWEFUSA-N 0.000 claims 1
- YVFQNCXSOKGUTA-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(1,3-oxazol-2-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1OC=CN=1 YVFQNCXSOKGUTA-FNZWTVRRSA-N 0.000 claims 1
- QUCWJFTVJFXUBN-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(1,3-thiazol-2-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1SC=CN=1 QUCWJFTVJFXUBN-FNZWTVRRSA-N 0.000 claims 1
- LCBYYQCHPYAMAA-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(1-methyltriazol-4-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1N=NN(C=1)C LCBYYQCHPYAMAA-FNZWTVRRSA-N 0.000 claims 1
- QWPFUQZBGLYFTF-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(1H-pyrazol-5-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C1=CC=NN1 QWPFUQZBGLYFTF-FNZWTVRRSA-N 0.000 claims 1
- FMMKYZHLTXUZKO-DWACAAAGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(2-ethoxyethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCCOCC)=O FMMKYZHLTXUZKO-DWACAAAGSA-N 0.000 claims 1
- VUYVAYGJSMJMLO-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(2-methoxyethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCCOC)=O VUYVAYGJSMJMLO-IDISGSTGSA-N 0.000 claims 1
- QCSSIMDSRXNAGT-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(2-oxopyrrolidin-1-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)N1C(CCC1)=O QCSSIMDSRXNAGT-IDISGSTGSA-N 0.000 claims 1
- UPKJWUVIXKPLKC-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(3-methyl-1,2,4-oxadiazol-5-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C1=NC(=NO1)C UPKJWUVIXKPLKC-FNZWTVRRSA-N 0.000 claims 1
- DFIFIZUBBHPKMN-KMRXNPHXSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1OC(=NN=1)C1CC1 DFIFIZUBBHPKMN-KMRXNPHXSA-N 0.000 claims 1
- AIHJSSHJPYVNAK-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(5-methyl-1,3,4-oxadiazol-2-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1OC(=NN=1)C AIHJSSHJPYVNAK-FNZWTVRRSA-N 0.000 claims 1
- BATIOXOHZJUKRZ-IADCTJSHSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(6-methoxypyridin-3-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)OC BATIOXOHZJUKRZ-IADCTJSHSA-N 0.000 claims 1
- YWDHTIYWSRIUSE-OUTSHDOLSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(6-methylpyridin-3-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)C YWDHTIYWSRIUSE-OUTSHDOLSA-N 0.000 claims 1
- LQMYJHURRVJYOL-FKAPRUDGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(6-pyrazol-1-ylpyridin-3-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)N1N=CC=C1 LQMYJHURRVJYOL-FKAPRUDGSA-N 0.000 claims 1
- LZPCRDPNQQMKJM-DWACAAAGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(cyclobutylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1CCC1)=O LZPCRDPNQQMKJM-DWACAAAGSA-N 0.000 claims 1
- UOPNLVPPPONXJH-IADCTJSHSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(cyclopentylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1CCCC1)=O UOPNLVPPPONXJH-IADCTJSHSA-N 0.000 claims 1
- VBKGXTLRBXXGGA-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(cyclopropylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1CC1)=O VBKGXTLRBXXGGA-IDISGSTGSA-N 0.000 claims 1
- MULMVPWPRFNYIF-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(ethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCC)=O MULMVPWPRFNYIF-FNZWTVRRSA-N 0.000 claims 1
- YMVUAIGTKUWGRM-DFBJGRDBSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(methylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC)=O YMVUAIGTKUWGRM-DFBJGRDBSA-N 0.000 claims 1
- ICKICOWFQFXMFT-IADCTJSHSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(oxan-4-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1CCOCC1)=O ICKICOWFQFXMFT-IADCTJSHSA-N 0.000 claims 1
- QSRLBYGDVFRMPT-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(propan-2-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC(C)C)=O QSRLBYGDVFRMPT-IDISGSTGSA-N 0.000 claims 1
- UDAIGVUOCPJRJV-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(propylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCCC)=O UDAIGVUOCPJRJV-IDISGSTGSA-N 0.000 claims 1
- SVAAVEYCJWGPIR-ZTOMLWHTSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(pyridin-2-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1=NC=CC=C1)=O SVAAVEYCJWGPIR-ZTOMLWHTSA-N 0.000 claims 1
- KKCSSZHLXPTZJP-KMRXNPHXSA-N 4-[4-cyano-2-[[(1'R,4S)-6-[(1-methylpyrazol-3-yl)carbamoyl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1=NN(C=C1)C)=O KKCSSZHLXPTZJP-KMRXNPHXSA-N 0.000 claims 1
- CINUPXLYJSEDQY-NGQVCNFZSA-N 4-[4-cyano-2-[[(1'R,4S)-6-[6-(dimethylamino)pyridin-3-yl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)N(C)C CINUPXLYJSEDQY-NGQVCNFZSA-N 0.000 claims 1
- SXBCGSNJVIIQCT-IADCTJSHSA-N 4-[4-cyano-2-[[(1'R,4S)-6-[6-(methylamino)pyridin-3-yl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)NC SXBCGSNJVIIQCT-IADCTJSHSA-N 0.000 claims 1
- FFFBPKJDCFGSLV-LVXARBLLSA-N 4-[4-cyano-2-[[(1'R,4S)-6-pyrazol-1-ylspiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)N1N=CC=C1 FFFBPKJDCFGSLV-LVXARBLLSA-N 0.000 claims 1
- KFHYFYXQIKMFRW-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-pyridazin-3-ylspiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1N=NC=CC=1 KFHYFYXQIKMFRW-IDISGSTGSA-N 0.000 claims 1
- PPMIOJROQLACFP-CUNXSJBXSA-N 4-[4-cyano-2-[[(1'R,4S)-6-pyridazin-4-ylspiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C1=CN=NC=C1 PPMIOJROQLACFP-CUNXSJBXSA-N 0.000 claims 1
- OZNMDUMCOQLPOH-DWACAAAGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-pyridin-2-ylspiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C1=NC=CC=C1 OZNMDUMCOQLPOH-DWACAAAGSA-N 0.000 claims 1
- BZHJNOJKWQGDDW-FIPFOOKPSA-N 4-[4-cyano-2-[[(1'R,4S)-6-pyridin-3-ylspiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC=CC=1 BZHJNOJKWQGDDW-FIPFOOKPSA-N 0.000 claims 1
- LFBIGDHEMXWJMI-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-7-(2-methoxyethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=CC=C12)C(NCCOC)=O LFBIGDHEMXWJMI-IDISGSTGSA-N 0.000 claims 1
- WRMUIOYLBINZSS-DFBJGRDBSA-N 4-[4-cyano-2-[[(1'R,4S)-7-(methylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=CC=C12)C(NC)=O WRMUIOYLBINZSS-DFBJGRDBSA-N 0.000 claims 1
- IIHXHXMKLLDTHR-DCFHFQCYSA-N 4-[4-cyano-2-[[(1'R,4S)-7-fluoro-6-(2-methoxyethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=C(C=C12)C(NCCOC)=O)F IIHXHXMKLLDTHR-DCFHFQCYSA-N 0.000 claims 1
- BOJOWEBHNARVSK-BVZFJXPGSA-N 4-[4-cyano-2-[[(1'R,4S)-7-fluoro-6-(methylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=C(C=C12)C(NC)=O)F BOJOWEBHNARVSK-BVZFJXPGSA-N 0.000 claims 1
- FVALLBPEEPBOMY-DCFHFQCYSA-N 4-[4-cyano-2-[[(1'R,4S)-7-fluoro-6-(propan-2-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=C(C=C12)C(NC(C)C)=O)F FVALLBPEEPBOMY-DCFHFQCYSA-N 0.000 claims 1
- QTPFRUHAKLYJNL-KMRXNPHXSA-N 4-[4-cyano-2-[[(1'R,4S)-7-methoxy-6-(2-methoxyethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=C(C=C12)C(NCCOC)=O)OC QTPFRUHAKLYJNL-KMRXNPHXSA-N 0.000 claims 1
- JQFCHUQULTXMSH-SIBVEZHUSA-N 4-[4-cyano-2-[[(1'R,4S)-7-methoxy-6-(methylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=C(C=C12)C(NC)=O)OC JQFCHUQULTXMSH-SIBVEZHUSA-N 0.000 claims 1
- JHMFXNSQQQMEIY-ZTPQKOODSA-N C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(N[C@@H]1CC[C@@H](CC1)O)=O Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(N[C@@H]1CC[C@@H](CC1)O)=O JHMFXNSQQQMEIY-ZTPQKOODSA-N 0.000 claims 1
- JHMFXNSQQQMEIY-NPNXHEJNSA-N C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(N[C@@H]1CC[C@H](CC1)O)=O Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(N[C@@H]1CC[C@H](CC1)O)=O JHMFXNSQQQMEIY-NPNXHEJNSA-N 0.000 claims 1
- GTXWSWZZFKCITN-RSBJHCHKSA-N CCC(C(O)=O)C(C=CC(C#N)=C1)=C1NC([C@H](C1)[C@]11C2=CC(C(NC3=CN(C)N=C3)=O)=CC=C2CC1)=O Chemical compound CCC(C(O)=O)C(C=CC(C#N)=C1)=C1NC([C@H](C1)[C@]11C2=CC(C(NC3=CN(C)N=C3)=O)=CC=C2CC1)=O GTXWSWZZFKCITN-RSBJHCHKSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
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| CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
| TWI795362B (zh) | 2016-07-07 | 2023-03-11 | 日商小野藥品工業股份有限公司 | 拮抗藥與免疫核查點阻礙藥而成之組合 |
| MX388257B (es) | 2017-05-18 | 2025-03-19 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2. |
| AR111941A1 (es) | 2017-05-18 | 2019-09-04 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
| EP3625223B1 (en) | 2017-05-18 | 2021-08-11 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives |
| JP7093791B2 (ja) | 2017-05-18 | 2022-06-30 | イドーシア ファーマシューティカルズ リミテッド | Ｐｇｅ２レセプター調節剤としてのベンゾフラン及びベンゾチオフェン誘導体 |
| US20200069686A1 (en) | 2017-05-18 | 2020-03-05 | Idorsia Pharmaceuticals Ltd | N-substituted indole derivatives |
| ES2954717T3 (es) | 2017-05-22 | 2023-11-23 | Ono Pharmaceutical Co | Antagonista de EP4 |
| US10617667B2 (en) | 2017-11-01 | 2020-04-14 | Ono Pharmaceutical Co., Ltd. | Method for treating brain tumors |
| CN112300019A (zh) * | 2019-07-31 | 2021-02-02 | 华东师范大学 | 一种邻乙酰氨基苯丁酸类化合物的制备方法 |
| EP4245301A4 (en) | 2020-11-13 | 2024-08-21 | ONO Pharmaceutical Co., Ltd. | TREATMENT OF CANCER BY COMBINED USE OF AN EP4 ANTAGONIST AND AN IMMUNE CHECKPOINT INHIBITOR |
| JP2024016314A (ja) * | 2020-12-24 | 2024-02-07 | 小野薬品工業株式会社 | 一般式（ｉ－ａ）で示される化合物、その薬学的に許容される塩、またはそれらの水和物と免疫チェックポイント阻害薬および／またはｅｐ４受容体拮抗薬との組み合わせ |
| CN114790186A (zh) * | 2021-01-25 | 2022-07-26 | 武汉人福创新药物研发中心有限公司 | 作为ep4拮抗剂的稠环化合物及其制备方法和用途 |
| CN117377656A (zh) * | 2021-05-28 | 2024-01-09 | 南京明德新药研发有限公司 | 苯并螺杂环衍生物及其应用 |
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| US6242493B1 (en) * | 1998-03-13 | 2001-06-05 | Merck Frosst Canada & Co. | Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment |
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| JP2002506851A (ja) * | 1998-03-13 | 2002-03-05 | メルク フロスト カナダ アンド カンパニー | カルボン酸類およびアシルスルホンアミド類、そのような化合物を含む組成物ならびに治療方法 |
| US6211197B1 (en) | 1998-10-07 | 2001-04-03 | Merck Frosst Canada & Co. | Prostaglandin receptor ligands |
| WO2002016311A1 (en) * | 2000-08-22 | 2002-02-28 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives, process for producing the same and drugs containing the same as the active ingredient |
| GB0031302D0 (en) * | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Napthalene derivatives |
| BR0211810A (pt) * | 2001-08-09 | 2004-08-24 | Ono Pharmaceutical Co | Derivados ácido carboxìlico e agente farmacêutico compreendendo os mesmos como ingrediente ativo |
| JP4547912B2 (ja) | 2002-03-05 | 2010-09-22 | 小野薬品工業株式会社 | ８−アザプロスタグランジン誘導体化合物およびその化合物を有効成分として含有する薬剤 |
| WO2004037247A1 (en) | 2002-10-21 | 2004-05-06 | Irm Llc | Oxindoles with anti-hiv activity |
| SI2476667T1 (sl) * | 2003-02-26 | 2014-10-30 | Sugen, Inc. | Aminoheteroarilne spojine kot inhibitorji protein-kinaze |
| CN1950334A (zh) | 2004-05-04 | 2007-04-18 | 辉瑞有限公司 | 邻位取代的芳基或杂芳基酰胺化合物 |
| GB0808282D0 (en) | 2008-05-07 | 2008-06-11 | Medical Res Council | Compounds for use in stabilizing p53 mutants |
| WO2012071458A1 (en) * | 2010-11-22 | 2012-05-31 | Array Biopharma Inc. | Heterocyclic inhibitors of beta - secretase for the treatment of neurodegenerative diseases |
| US9181279B2 (en) | 2011-07-04 | 2015-11-10 | Rottapharm Biotech S.R.L. | Cyclic amine derivatives as EP4 receptor antagonists |
| WO2013090552A1 (en) | 2011-12-13 | 2013-06-20 | Yale University | Compositions and methods for reducing ctl exhaustion |
| WO2015000949A1 (en) | 2013-07-03 | 2015-01-08 | F. Hoffmann-La Roche Ag | Heteroaryl pyridone and aza-pyridone amide compounds |
| TWI739666B (zh) * | 2015-01-09 | 2021-09-11 | 日商小野藥品工業股份有限公司 | 醫藥組成物 |
| TWI795362B (zh) * | 2016-07-07 | 2023-03-11 | 日商小野藥品工業股份有限公司 | 拮抗藥與免疫核查點阻礙藥而成之組合 |
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