JP2017533958A5 - - Google Patents
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- Publication number
- JP2017533958A5 JP2017533958A5 JP2017542792A JP2017542792A JP2017533958A5 JP 2017533958 A5 JP2017533958 A5 JP 2017533958A5 JP 2017542792 A JP2017542792 A JP 2017542792A JP 2017542792 A JP2017542792 A JP 2017542792A JP 2017533958 A5 JP2017533958 A5 JP 2017533958A5
- Authority
- JP
- Japan
- Prior art keywords
- difluoro
- dihydro
- benzodioxol
- alkyl
- carbonyl
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 121
- 239000001257 hydrogen Substances 0.000 claims 121
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 96
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 73
- 150000002431 hydrogen Chemical class 0.000 claims 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 56
- 229910052736 halogen Inorganic materials 0.000 claims 50
- 150000002367 halogens Chemical class 0.000 claims 50
- 239000003814 drug Substances 0.000 claims 39
- 150000003839 salts Chemical class 0.000 claims 34
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000005466 alkylenyl group Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 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 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 239000003607 modifier Substances 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- VKAKPRNMTJYMDK-DENIHFKCSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=CC=C12)C=1C=C(C(=O)O)C=CC=1)F VKAKPRNMTJYMDK-DENIHFKCSA-N 0.000 claims 2
- SRKHILYHEMRDJV-NFBKMPQASA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-6-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=C(C=C12)OC)C=1C=C(C(=O)O)C=CC=1)F SRKHILYHEMRDJV-NFBKMPQASA-N 0.000 claims 2
- WTYLHDFHALABGA-NFBKMPQASA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-6-methyl-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=C(C=C12)C)C=1C=C(C(=O)O)C=CC=1)F WTYLHDFHALABGA-NFBKMPQASA-N 0.000 claims 2
- LSBRKYXIZOVMPC-IFMALSPDSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C=1C=C(C(=O)O)C=CC=1)F LSBRKYXIZOVMPC-IFMALSPDSA-N 0.000 claims 2
- CSHQOZKSESHPDD-UYAOXDASSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=NC(=CC=C21)OC)C=1C=C(C(=O)O)C=CC=1)F CSHQOZKSESHPDD-UYAOXDASSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- XTSZEUHRHYBQPO-NFBKMPQASA-N 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]-3-fluorobenzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1=C(C=C(C(=O)O)C=C1)F)F XTSZEUHRHYBQPO-NFBKMPQASA-N 0.000 claims 2
- XJSGHOOFABZHRF-IFMALSPDSA-N 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1=CC=C(C(=O)O)C=C1)F XJSGHOOFABZHRF-IFMALSPDSA-N 0.000 claims 2
- YZCXEGOOJKXITN-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromene-2-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)O)F YZCXEGOOJKXITN-UHFFFAOYSA-N 0.000 claims 2
- OYXWDWIOIHJMLH-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-N-[3-(trifluoromethyl)oxetan-3-yl]-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC1(COC1)C(F)(F)F)F OYXWDWIOIHJMLH-UHFFFAOYSA-N 0.000 claims 2
- OHLSDRGCUVUFAK-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-N-methyl-N-(oxetan-3-yl)-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)N(C1COC1)C)F OHLSDRGCUVUFAK-UHFFFAOYSA-N 0.000 claims 2
- GJMIGFMXSNUGBH-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(1,3-dihydroxypropan-2-yl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC(CO)CO)F GJMIGFMXSNUGBH-UHFFFAOYSA-N 0.000 claims 2
- HQKHLKLPLDDCOU-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(1-hydroxy-2-methylpropan-2-yl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC(CO)(C)C)F HQKHLKLPLDDCOU-UHFFFAOYSA-N 0.000 claims 2
- SDNLQZGBDJQTCU-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxy-1-phenylethyl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC(CO)C1=CC=CC=C1)F SDNLQZGBDJQTCU-UHFFFAOYSA-N 0.000 claims 2
- PERSPLBHGJGFBH-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxy-2,3-dihydro-1H-inden-1-yl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC1C(CC2=CC=CC=C12)O)F PERSPLBHGJGFBH-UHFFFAOYSA-N 0.000 claims 2
- LRHWYIHMPZSRMB-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxyethyl)-7-methoxy-N-propyl-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)N(CCC)CCO)F LRHWYIHMPZSRMB-UHFFFAOYSA-N 0.000 claims 2
- QRWFAMXSXDRNMU-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-[2-(3-hydroxyphenyl)ethyl]-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NCCC1=CC(=CC=C1)O)F QRWFAMXSXDRNMU-UHFFFAOYSA-N 0.000 claims 2
- WWWHRBUAGBFEOU-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-[2-hydroxy-1-(2-methoxyphenyl)ethyl]-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC(CO)C1=C(C=CC=C1)OC)F WWWHRBUAGBFEOU-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- QOCYWINHZRJGOS-UHFFFAOYSA-N N-benzyl-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxyethyl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C1OC2=CC(=CC=C2C(C1)NC(=O)C1(CC1)C1=CC2=C(OC(O2)(F)F)C=C1)OC)CCO QOCYWINHZRJGOS-UHFFFAOYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 230000003321 amplification Effects 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003623 enhancer Substances 0.000 claims 2
- JQSQQJJXKKPLOH-UHFFFAOYSA-N ethyl 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromene-2-carboxylate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)OCC)F JQSQQJJXKKPLOH-UHFFFAOYSA-N 0.000 claims 2
- QVDYQHXNAQHIKH-TZIWHRDSSA-N galicaftor Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC(F)F)C1=CC=C(C(=O)O)C=C1)F QVDYQHXNAQHIKH-TZIWHRDSSA-N 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 238000003199 nucleic acid amplification method Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NGVCCYZZKURXNI-NFBKMPQASA-N (2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-2-(3-methoxyphenyl)-3,4-dihydro-2H-chromene-6-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=C(C=C12)C(=O)O)C1=CC(=CC=C1)OC)F NGVCCYZZKURXNI-NFBKMPQASA-N 0.000 claims 1
- ZJUNWVZICRFHBM-UHFFFAOYSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-N-(7-fluorospiro[3,4-dihydrochromene-2,4'-piperidine]-4-yl)cyclopropane-1-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC2(CCNCC2)OC2=CC(=CC=C12)F)F ZJUNWVZICRFHBM-UHFFFAOYSA-N 0.000 claims 1
- XRJMWUOXRXEABQ-UHFFFAOYSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-N-(7-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)cyclopropane-1-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)O)(C)C)F XRJMWUOXRXEABQ-UHFFFAOYSA-N 0.000 claims 1
- PEZMUBLXTZBCNH-UHFFFAOYSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-N-(7-methoxy-2-phenyl-3,4-dihydro-2H-chromen-4-yl)cyclopropane-1-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C1=CC=CC=C1)F PEZMUBLXTZBCNH-UHFFFAOYSA-N 0.000 claims 1
- DGNDJPPKJOAWAC-GWQXNCQPSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-N-[(2R)-2-[3-(hydroxymethyl)phenyl]-3,4-dihydro-2H-chromen-4-yl]cyclopropane-1-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1C[C@@H](OC2=CC=CC=C12)C1=CC(=CC=C1)CO)F DGNDJPPKJOAWAC-GWQXNCQPSA-N 0.000 claims 1
- FIGPLAHNTZOAJF-QSVWIEALSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-N-[1'-[(2R)-2,3-dihydroxypropyl]-7-fluorospiro[3,4-dihydrochromene-2,4'-piperidine]-4-yl]cyclopropane-1-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC2(CCN(CC2)C[C@H](CO)O)OC2=CC(=CC=C12)F)F FIGPLAHNTZOAJF-QSVWIEALSA-N 0.000 claims 1
- BFKUPQRXHTXTGP-KMDAROACSA-N 1-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromene-2-carbonyl]pyrrolidine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=CC(=CC=C12)OC)C(=O)N1CC(CC1)C(=O)O)F BFKUPQRXHTXTGP-KMDAROACSA-N 0.000 claims 1
- HLQQBLAKLHTEGP-IKJXHCRLSA-N 2-[(4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]-1,3-thiazole-5-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1CC(OC2=CC=CC=C12)C=1SC(=CN=1)C(=O)O)F HLQQBLAKLHTEGP-IKJXHCRLSA-N 0.000 claims 1
- HLQQBLAKLHTEGP-PIVQAISJSA-N 2-[(4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]-1,3-thiazole-5-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1CC(OC2=CC=CC=C12)C=1SC(=CN=1)C(=O)O)F HLQQBLAKLHTEGP-PIVQAISJSA-N 0.000 claims 1
- BVGBHKSSRZNDGR-UYAOXDASSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=NC=CC=C21)C=1C=C(C(=O)O)C=CC=1)F BVGBHKSSRZNDGR-UYAOXDASSA-N 0.000 claims 1
- CRDJGWCUZSSRJK-FYYLOGMGSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(2-fluoroethoxy)-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OCCF)C=1C=C(C(=O)O)C=CC=1)F CRDJGWCUZSSRJK-FYYLOGMGSA-N 0.000 claims 1
- KWNVHMCTCWXXLZ-TZIWHRDSSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(difluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC(F)F)C=1C=C(C(=O)O)C=CC=1)F KWNVHMCTCWXXLZ-TZIWHRDSSA-N 0.000 claims 1
- RWEGRZFSDHFSTP-ITYSUYTRSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(difluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]cyclohexane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC(F)F)C1CC(CCC1)C(=O)O)F RWEGRZFSDHFSTP-ITYSUYTRSA-N 0.000 claims 1
- ZQUKOPGOGYBHSM-TZIWHRDSSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(trifluoromethyl)-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)C(F)(F)F)C=1C=C(C(=O)O)C=CC=1)F ZQUKOPGOGYBHSM-TZIWHRDSSA-N 0.000 claims 1
- MVTOWPCDANAKLO-ITYSUYTRSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(trifluoromethyl)-3,4-dihydro-2H-chromen-2-yl]cyclohexane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)C(F)(F)F)C1CC(CCC1)C(=O)O)F MVTOWPCDANAKLO-ITYSUYTRSA-N 0.000 claims 1
- UTVVEKUCCRQJLL-TZIWHRDSSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-fluoro-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)F)C=1C=C(C(=O)O)C=CC=1)F UTVVEKUCCRQJLL-TZIWHRDSSA-N 0.000 claims 1
- WDWOEIFSDKCCKM-ITYSUYTRSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-fluoro-3,4-dihydro-2H-chromen-2-yl]cyclohexane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)F)C1CC(CCC1)C(=O)O)F WDWOEIFSDKCCKM-ITYSUYTRSA-N 0.000 claims 1
- YASXAOSKFMKUJR-TZIWHRDSSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-hydroxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)O)C=1C=C(C(=O)O)C=CC=1)F YASXAOSKFMKUJR-TZIWHRDSSA-N 0.000 claims 1
- LNISXGOUUJSXSW-GJGFTSBZSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]bicyclo[1.1.1]pentane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C12CC(C1)(C2)C(=O)O)F LNISXGOUUJSXSW-GJGFTSBZSA-N 0.000 claims 1
- JVBNKDSHGWEEAW-UOBKPFSRSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]cyclohexane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1CC(CCC1)C(=O)O)F JVBNKDSHGWEEAW-UOBKPFSRSA-N 0.000 claims 1
- BOFFDTYASKWXTL-IFMALSPDSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methyl-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)C)C=1C=C(C(=O)O)C=CC=1)F BOFFDTYASKWXTL-IFMALSPDSA-N 0.000 claims 1
- PEXRXNLCECMCCF-IXCJQBJRSA-N 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-phenylmethoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound C(C1=CC=CC=C1)OC1=CC=C2[C@@H](C[C@@H](OC2=C1)C=1C=C(C(=O)O)C=CC=1)NC(=O)C1(CC1)C1=CC2=C(OC(O2)(F)F)C=C1 PEXRXNLCECMCCF-IXCJQBJRSA-N 0.000 claims 1
- XFPZXQUEOZKBQA-IFMALSPDSA-N 3-[(2R,4R)-7-(carboxymethoxy)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound C(=O)(O)COC1=CC=C2[C@@H](C[C@@H](OC2=C1)C=1C=C(C(=O)O)C=CC=1)NC(=O)C1(CC1)C1=CC2=C(OC(O2)(F)F)C=C1 XFPZXQUEOZKBQA-IFMALSPDSA-N 0.000 claims 1
- YVTUUXUDYNGFQA-IEBWSBKVSA-N 3-[(2R,4R)-7-chloro-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl]benzoic acid Chemical compound ClC1=CC=C2C(=N1)O[C@H](C[C@H]2NC(=O)C1(CC1)C1=CC2=C(OC(O2)(F)F)C=C1)C=1C=C(C(=O)O)C=CC=1 YVTUUXUDYNGFQA-IEBWSBKVSA-N 0.000 claims 1
- VKAKPRNMTJYMDK-SIKLNZKXSA-N 3-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=CC=CC=C12)C=1C=C(C(=O)O)C=CC=1)F VKAKPRNMTJYMDK-SIKLNZKXSA-N 0.000 claims 1
- BVGBHKSSRZNDGR-AZUAARDMSA-N 3-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=NC=CC=C21)C=1C=C(C(=O)O)C=CC=1)F BVGBHKSSRZNDGR-AZUAARDMSA-N 0.000 claims 1
- WTYLHDFHALABGA-NZQKXSOJSA-N 3-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-6-methyl-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=CC=C(C=C12)C)C=1C=C(C(=O)O)C=CC=1)F WTYLHDFHALABGA-NZQKXSOJSA-N 0.000 claims 1
- LSBRKYXIZOVMPC-RBBKRZOGSA-N 3-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=CC(=CC=C12)OC)C=1C=C(C(=O)O)C=CC=1)F LSBRKYXIZOVMPC-RBBKRZOGSA-N 0.000 claims 1
- CSHQOZKSESHPDD-AZUAARDMSA-N 3-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=NC(=CC=C21)OC)C=1C=C(C(=O)O)C=CC=1)F CSHQOZKSESHPDD-AZUAARDMSA-N 0.000 claims 1
- BOFFDTYASKWXTL-RBBKRZOGSA-N 3-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methyl-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=CC(=CC=C12)C)C=1C=C(C(=O)O)C=CC=1)F BOFFDTYASKWXTL-RBBKRZOGSA-N 0.000 claims 1
- KVQFRBIVUOWXME-UHFFFAOYSA-N 3-[4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]cyclobutane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC=CC=C12)C1CC(C1)C(=O)O)F KVQFRBIVUOWXME-UHFFFAOYSA-N 0.000 claims 1
- CQXMDLNKHWVJRQ-KNWWKWMGSA-N 3-[[3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methyl-3,4-dihydro-2H-chromen-2-yl]benzoyl]amino]-1-methylcyclopentane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)C)C=1C=C(C(=O)NC2CC(CC2)(C(=O)O)C)C=CC=1)F CQXMDLNKHWVJRQ-KNWWKWMGSA-N 0.000 claims 1
- AVFLFALDCGWQKK-DENIHFKCSA-N 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=CC=C12)C1=CC=C(C(=O)O)C=C1)F AVFLFALDCGWQKK-DENIHFKCSA-N 0.000 claims 1
- NJZBZJCTBWHZQH-IFMALSPDSA-N 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(difluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]-N-methylsulfonylbenzamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC(F)F)C1=CC=C(C(=O)NS(=O)(=O)C)C=C1)F NJZBZJCTBWHZQH-IFMALSPDSA-N 0.000 claims 1
- VECHQTHNXRCICS-TZIWHRDSSA-N 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-hydroxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)O)C1=CC=C(C(=O)O)C=C1)F VECHQTHNXRCICS-TZIWHRDSSA-N 0.000 claims 1
- CCKJRGMELFYOHT-IFMALSPDSA-N 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]-2-fluorobenzoic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1=CC(=C(C(=O)O)C=C1)F)F CCKJRGMELFYOHT-IFMALSPDSA-N 0.000 claims 1
- WJSYAUBTRHCJQI-WOJBJXKFSA-N 4-[(2R,4R)-4-[[1-(6-bromo-2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(difluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound BrC=1C(=CC2=C(OC(O2)(F)F)C=1)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC(F)F)C1=CC=C(C(=O)O)C=C1 WJSYAUBTRHCJQI-WOJBJXKFSA-N 0.000 claims 1
- IQDDOTAJKMWLIV-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromene-7-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CCOC2=CC(=CC=C12)C(=O)O)F IQDDOTAJKMWLIV-UHFFFAOYSA-N 0.000 claims 1
- HZEVMOQDOAREKI-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxyspiro[3,4-dihydrochromene-2,3'-cyclobutane]-1'-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC2(CC(C2)C(=O)O)OC2=CC(=CC=C12)OC)F HZEVMOQDOAREKI-UHFFFAOYSA-N 0.000 claims 1
- MTNCOCXLOZLWAV-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxy-2-methylpropyl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NCC(C)(C)O)F MTNCOCXLOZLWAV-UHFFFAOYSA-N 0.000 claims 1
- KSYKHQIKANBBMW-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxy-2-phenylethyl)-7-methoxy-N-methyl-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)N(C)CC(C1=CC=CC=C1)O)F KSYKHQIKANBBMW-UHFFFAOYSA-N 0.000 claims 1
- LCSQDSTWBQEXKA-UHFFFAOYSA-N 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-N-(2-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)NC1=C(C=CC=C1)O)F LCSQDSTWBQEXKA-UHFFFAOYSA-N 0.000 claims 1
- YNVOXKQOTDSUNO-WIYYLYMNSA-N 6-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]pyridine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=CC=C12)C1=CC=C(C=N1)C(=O)O)F YNVOXKQOTDSUNO-WIYYLYMNSA-N 0.000 claims 1
- YNVOXKQOTDSUNO-GHTZIAJQSA-N 6-[(2R,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]pyridine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@H]1C[C@@H](OC2=CC=CC=C12)C1=CC=C(C=N1)C(=O)O)F YNVOXKQOTDSUNO-GHTZIAJQSA-N 0.000 claims 1
- KSOSRWFHDUPQCG-OVQIUMAMSA-N FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=C(C=C12)C(=O)OC)C1CC(CCC1)OC)F Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=C(C=C12)C(=O)OC)C1CC(CCC1)OC)F KSOSRWFHDUPQCG-OVQIUMAMSA-N 0.000 claims 1
- UZDBESPMRVINQZ-UHFFFAOYSA-N N-(6-bromo-2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NC1=CC2=C(OC(O2)(F)F)C=C1Br UZDBESPMRVINQZ-UHFFFAOYSA-N 0.000 claims 1
- FYFPQQZNOZAEGQ-UHFFFAOYSA-N N-(7-bromo-3,4-dihydro-2H-chromen-4-yl)-1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxamide Chemical compound BrC1=CC=C2C(CCOC2=C1)NC(=O)C1(CC1)C1=CC2=C(OC(O2)(F)F)C=C1 FYFPQQZNOZAEGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- GDGUOMPFOZMEDH-UHFFFAOYSA-N benzyl 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-fluorospiro[3,4-dihydrochromene-2,3'-azetidine]-1'-carboxylate Chemical compound FC1=CC=C2C(CC3(CN(C3)C(=O)OCC3=CC=CC=C3)OC2=C1)NC(=O)C1(CC1)C1=CC2=C(OC(F)(F)O2)C=C1 GDGUOMPFOZMEDH-UHFFFAOYSA-N 0.000 claims 1
- ORCXPYPDHLVQFP-UHFFFAOYSA-N bicyclo[1.1.1]pentane-3-carboxylic acid Chemical compound C1C2CC1(C(=O)O)C2 ORCXPYPDHLVQFP-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WQESEQRJOKCYPK-IFMALSPDSA-N ethyl 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-pyrano[2,3-c]pyridin-2-yl]benzoate Chemical compound CCOC(=O)C1=CC(=CC=C1)[C@H]1C[C@@H](NC(=O)C2(CC2)C2=CC3=C(OC(F)(F)O3)C=C2)C2=CC=NC=C2O1 WQESEQRJOKCYPK-IFMALSPDSA-N 0.000 claims 1
- WQESEQRJOKCYPK-UNMCSNQZSA-N ethyl 3-[(2S,4S)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-pyrano[2,3-c]pyridin-2-yl]benzoate Chemical compound CCOC(=O)C1=CC(=CC=C1)[C@@H]1C[C@H](NC(=O)C2(CC2)C2=CC3=C(OC(F)(F)O3)C=C2)C2=CC=NC=C2O1 WQESEQRJOKCYPK-UNMCSNQZSA-N 0.000 claims 1
- KETGKZCYUZTDRS-NFBKMPQASA-N ethyl 6-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]pyridine-3-carboxylate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=CC=C12)C1=CC=C(C=N1)C(=O)OCC)F KETGKZCYUZTDRS-NFBKMPQASA-N 0.000 claims 1
- NIQZZSVGSVTESJ-NFBKMPQASA-N methyl 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=CC=C12)C=1C=C(C(=O)OC)C=CC=1)F NIQZZSVGSVTESJ-NFBKMPQASA-N 0.000 claims 1
- HUAWWFOTUHVZKO-ZJSXRUAMSA-N methyl 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-6-methyl-3,4-dihydro-2H-chromen-2-yl]benzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC=C(C=C12)C)C=1C=C(C(=O)OC)C=CC=1)F HUAWWFOTUHVZKO-ZJSXRUAMSA-N 0.000 claims 1
- OAYFZJDDFXRCNG-ILBGXUMGSA-N methyl 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-(2-methoxyethoxy)-3,4-dihydro-2H-chromen-2-yl]benzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OCCOC)C=1C=C(C(=O)OC)C=CC=1)F OAYFZJDDFXRCNG-ILBGXUMGSA-N 0.000 claims 1
- UAHJMCZIOJCVCQ-UYAOXDASSA-N methyl 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-fluoro-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl]benzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=NC(=CC=C21)F)C=1C=C(C(=O)OC)C=CC=1)F UAHJMCZIOJCVCQ-UYAOXDASSA-N 0.000 claims 1
- CHPNQBODAFODSG-XRKRLSELSA-N methyl 3-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-phenylmethoxy-3,4-dihydro-2H-chromen-2-yl]benzoate Chemical compound C(C1=CC=CC=C1)OC1=CC=C2[C@@H](C[C@@H](OC2=C1)C=1C=C(C(=O)OC)C=CC=1)NC(=O)C1(CC1)C1=CC2=C(OC(O2)(F)F)C=C1 CHPNQBODAFODSG-XRKRLSELSA-N 0.000 claims 1
- XFSRXDYLCXVDNV-IFMALSPDSA-N methyl 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-hydroxy-3,4-dihydro-2H-chromen-2-yl]benzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)O)C1=CC=C(C(=O)OC)C=C1)F XFSRXDYLCXVDNV-IFMALSPDSA-N 0.000 claims 1
- MISRKXQAPNCHFG-FYYLOGMGSA-N methyl 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]-2-fluorobenzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1=CC(=C(C(=O)OC)C=C1)F)F MISRKXQAPNCHFG-FYYLOGMGSA-N 0.000 claims 1
- BFFFFQKAOWQPQK-ZJSXRUAMSA-N methyl 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]-3-fluorobenzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1=C(C=C(C(=O)OC)C=C1)F)F BFFFFQKAOWQPQK-ZJSXRUAMSA-N 0.000 claims 1
- BWUWCRKBNSSNJX-FYYLOGMGSA-N methyl 4-[(2R,4R)-4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)N[C@@H]1C[C@@H](OC2=CC(=CC=C12)OC)C1=CC=C(C(=O)OC)C=C1)F BWUWCRKBNSSNJX-FYYLOGMGSA-N 0.000 claims 1
- HTFWGJCRYJSFHI-UHFFFAOYSA-N methyl 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3,4-dihydro-2H-chromene-7-carboxylate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CCOC2=CC(=CC=C12)C(=O)OC)F HTFWGJCRYJSFHI-UHFFFAOYSA-N 0.000 claims 1
- MGQPXULJUZJZOV-UHFFFAOYSA-N methyl 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromene-2-carboxylate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C(=O)OC)F MGQPXULJUZJZOV-UHFFFAOYSA-N 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- FEISDZVXIULCNZ-UHFFFAOYSA-N tert-butyl 3-[4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]azetidine-1-carboxylate Chemical compound FC1(OC2=C(O1)C=CC(=C2)C1(CC1)C(=O)NC1CC(OC2=CC(=CC=C12)OC)C1CN(C1)C(=O)OC(C)(C)C)F FEISDZVXIULCNZ-UHFFFAOYSA-N 0.000 claims 1
- VIUCGPMIISKZMI-UHFFFAOYSA-N tert-butyl 4-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-7-fluorospiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC2(CC1)CC(NC(=O)C1(CC1)C1=CC3=C(OC(F)(F)O3)C=C1)C1=CC=C(F)C=C1O2 VIUCGPMIISKZMI-UHFFFAOYSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
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| PCT/US2015/057837 WO2016069757A1 (en) | 2014-10-31 | 2015-10-28 | Substituted chromanes and method of use |
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