JP6062423B2 - 部分飽和三環式化合物ならびにその製造および使用方法 - Google Patents

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Publication number

JP6062423B2

JP6062423B2 JP2014509510A JP2014509510A JP6062423B2 JP 6062423 B2 JP6062423 B2 JP 6062423B2 JP 2014509510 A JP2014509510 A JP 2014509510A JP 2014509510 A JP2014509510 A JP 2014509510A JP 6062423 B2 JP6062423 B2 JP 6062423B2

Authority

JP

Japan

Prior art keywords

alkyl

group

chromene

carboxylic acid

alkoxy

Prior art date

2011-05-06

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 207
• 238000000034 method Methods 0.000 title claims description 166
• 229920006395 saturated elastomer Polymers 0.000 title claims description 10
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 313
• 125000003545 alkoxy group Chemical group 0.000 claims description 166
• -1 cyano, hydroxyl Chemical group 0.000 claims description 154
• 229910052739 hydrogen Inorganic materials 0.000 claims description 130
• 239000001257 hydrogen Substances 0.000 claims description 124
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 109
• 229910052757 nitrogen Inorganic materials 0.000 claims description 93
• 125000001424 substituent group Chemical group 0.000 claims description 93
• 125000000623 heterocyclic group Chemical group 0.000 claims description 92
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 83
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 76
• 235000019000 fluorine Nutrition 0.000 claims description 75
• 125000001153 fluoro group Chemical group F* 0.000 claims description 71
• 229910052731 fluorine Inorganic materials 0.000 claims description 70
• 239000011737 fluorine Substances 0.000 claims description 62
• 238000011282 treatment Methods 0.000 claims description 53
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 47
• 229910052760 oxygen Inorganic materials 0.000 claims description 46
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 43
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 43
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• ZEPXUAGXAMCRMI-UHFFFAOYSA-N 2h-chromene-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CCOC2=C1 ZEPXUAGXAMCRMI-UHFFFAOYSA-N 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 30
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 30
• 125000004043 oxo group Chemical group O=* 0.000 claims description 28
• 208000008589 Obesity Diseases 0.000 claims description 26
• 235000020824 obesity Nutrition 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000000304 alkynyl group Chemical group 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000002837 carbocyclic group Chemical group 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 18
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 16
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 13
• 230000004580 weight loss Effects 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 claims description 5
• RFYAVNPEHZYDNY-UHFFFAOYSA-N 5-[[2-[(4-ethyl-2-oxopiperazin-1-yl)methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound O=C1CN(CC)CCN1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O RFYAVNPEHZYDNY-UHFFFAOYSA-N 0.000 claims description 4
• JPKYDPJLUANHKK-HFCFLWKCSA-N 5-[[2-[2-[(2s)-1-ethylpyrrolidin-2-yl]ethylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN1CCC[C@H]1CCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O JPKYDPJLUANHKK-HFCFLWKCSA-N 0.000 claims description 4
• CPAFKFCQMRZTSG-ASFAAARLSA-N 5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O CPAFKFCQMRZTSG-ASFAAARLSA-N 0.000 claims description 4
• 241000282472 Canis lupus familiaris Species 0.000 claims description 4
• 241000282326 Felis catus Species 0.000 claims description 4
• GCHDTSWCKKSVAG-MIGHCRNESA-N (1ar,7bs)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O GCHDTSWCKKSVAG-MIGHCRNESA-N 0.000 claims description 3
• GCHDTSWCKKSVAG-FOVLHFFESA-N (1as,7br)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O GCHDTSWCKKSVAG-FOVLHFFESA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• HHKAHYNPEQELBS-UHFFFAOYSA-N 5-[[2-(1-ethylazetidin-3-yl)-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC1C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HHKAHYNPEQELBS-UHFFFAOYSA-N 0.000 claims description 3
• HUMNCXLVRGALON-UHFFFAOYSA-N 5-[[2-[(1-ethylazetidin-3-yl)methylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC1CNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HUMNCXLVRGALON-UHFFFAOYSA-N 0.000 claims description 3
• CPMVGKHOVQDUKF-IWQZZHSRSA-N 5-[[2-[(z)-3-(azetidin-1-yl)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1=CC=2C3CC3COC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=C(F)C=C1\C=C/CN1CCC1 CPMVGKHOVQDUKF-IWQZZHSRSA-N 0.000 claims description 3
• YUIRRDWVLSMXIU-GDNBJRDFSA-N 5-[[2-[(z)-3-(diethylamino)-2-methylprop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C(C)=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O YUIRRDWVLSMXIU-GDNBJRDFSA-N 0.000 claims description 3
• GCHDTSWCKKSVAG-WAYWQWQTSA-N 5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O GCHDTSWCKKSVAG-WAYWQWQTSA-N 0.000 claims description 3
• UUNFSQNJJFGUEO-SREVYHEPSA-N 5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-7b-methyl-1a,2-dihydro-1h-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C2C3(C)CC3COC2=C1C(O)=O UUNFSQNJJFGUEO-SREVYHEPSA-N 0.000 claims description 3
• AGHMOZRNLFASDQ-UHFFFAOYSA-N 5-[[2-[3-(dimethylamino)propylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O AGHMOZRNLFASDQ-UHFFFAOYSA-N 0.000 claims description 3
• HLOFTUAXAMEBGF-UHFFFAOYSA-N 5-[[2-[4-(dimethylamino)butanoylamino]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCC(=O)NC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HLOFTUAXAMEBGF-UHFFFAOYSA-N 0.000 claims description 3
• OMOSQIAXBHOKHD-UHFFFAOYSA-N 5-[[2-[4-(dimethylamino)butyl-methylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCCN(C)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O OMOSQIAXBHOKHD-UHFFFAOYSA-N 0.000 claims description 3
• HWBSTIVGLAXWIQ-UHFFFAOYSA-N 5-[[2-[4-(dimethylamino)butylamino]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCCNC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O HWBSTIVGLAXWIQ-UHFFFAOYSA-N 0.000 claims description 3
• OZSBDXQWHQBWBN-UHFFFAOYSA-N 5-[[2-[4-(dimethylamino)butylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O OZSBDXQWHQBWBN-UHFFFAOYSA-N 0.000 claims description 3
• CRHZHGHXFZJSHG-KLHKWILBSA-N 5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]methylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1CNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O CRHZHGHXFZJSHG-KLHKWILBSA-N 0.000 claims description 3
• BJERFOTWYWVBHU-MKJPBZQASA-N 5-[[2-[[(3s)-1-azabicyclo[2.2.2]octan-3-yl]amino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C12CC2COC2=C1C=CC(NS(=O)(=O)C=1C(=CC=CC=1)N[C@H]1C3CCN(CC3)C1)=C2C(=O)O BJERFOTWYWVBHU-MKJPBZQASA-N 0.000 claims description 3
• QWOYMUNZAVWJKX-CKDBGZEDSA-N 5-[[2-[[(3s)-1-ethylpyrrolidin-3-yl]amino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1NC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O QWOYMUNZAVWJKX-CKDBGZEDSA-N 0.000 claims description 3
• CPAFKFCQMRZTSG-ICXUMSERSA-N 5-[[2-[[(3s)-1-ethylpyrrolidin-3-yl]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O CPAFKFCQMRZTSG-ICXUMSERSA-N 0.000 claims description 3
• CRHZHGHXFZJSHG-HJOIGYKYSA-N 5-[[2-[[(3s)-1-ethylpyrrolidin-3-yl]methylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O CRHZHGHXFZJSHG-HJOIGYKYSA-N 0.000 claims description 3
• FNWIFNWEXAXQLI-PKUWUEBNSA-N 5-[[2-[[[(2r)-1-ethylpyrrolidine-2-carbonyl]amino]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN1CCC[C@@H]1C(=O)NCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O FNWIFNWEXAXQLI-PKUWUEBNSA-N 0.000 claims description 3
• KDJIJWHMONVMFX-JFFZSNJFSA-N 5-[[4-fluoro-2-[(Z)-3-[[(3S)-3-hydroxypyrrolidin-1-yl]amino]prop-1-enyl]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1[C@@H](O)CCN1NC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O KDJIJWHMONVMFX-JFFZSNJFSA-N 0.000 claims description 3
• ZCWOFNJPKNFIND-ARJAWSKDSA-N 5-[[4-fluoro-2-[(z)-3-(propan-2-ylamino)prop-1-enyl]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CC(C)NC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O ZCWOFNJPKNFIND-ARJAWSKDSA-N 0.000 claims description 3
• DXLALYXZEBBNEL-WAYWQWQTSA-N 7-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OCC2)C=N2)C2=C1C(O)=O DXLALYXZEBBNEL-WAYWQWQTSA-N 0.000 claims description 3
• 239000005973 Carvone Substances 0.000 claims description 3
• 238000007920 subcutaneous administration Methods 0.000 claims description 3
• 230000001629 suppression Effects 0.000 claims description 3
• ICNANHHADNBANV-NSSKKAGHSA-N (1ar,7bs)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O ICNANHHADNBANV-NSSKKAGHSA-N 0.000 claims description 2
• BQCTVQSCCVVOIO-GPAZVNKHSA-N (1ar,7bs)-5-[[2-[(z)-3-(ethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCNC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O BQCTVQSCCVVOIO-GPAZVNKHSA-N 0.000 claims description 2
• SCCNKTSIBMOCLE-VLCJXESFSA-N (1ar,7bs)-5-[[2-[(z)-4-(diethylamino)but-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)CC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O SCCNKTSIBMOCLE-VLCJXESFSA-N 0.000 claims description 2
• AGHMOZRNLFASDQ-HOCLYGCPSA-N (1ar,7bs)-5-[[2-[3-(dimethylamino)propylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CN(C)CCCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O AGHMOZRNLFASDQ-HOCLYGCPSA-N 0.000 claims description 2
• CPAFKFCQMRZTSG-QOKNQOGYSA-N (1ar,7bs)-5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]methyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O CPAFKFCQMRZTSG-QOKNQOGYSA-N 0.000 claims description 2
• QJMGLVARDLSSLY-YJLNNSPDSA-N (1ar,7bs)-5-[[2-[[(3r)-1-ethylpyrrolidin-3-yl]oxymethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1OCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O QJMGLVARDLSSLY-YJLNNSPDSA-N 0.000 claims description 2
• QJMGLVARDLSSLY-FNHZYXHNSA-N (1ar,7bs)-5-[[2-[[(3s)-1-ethylpyrrolidin-3-yl]oxymethyl]-4-fluorophenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@@H]1OCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2[C@@H](C2)CO2)C2=C1C(O)=O QJMGLVARDLSSLY-FNHZYXHNSA-N 0.000 claims description 2
• AFKYQMDFOQZUFV-CGYSWORWSA-N (1as,7br)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-1,1-difluoro-2,7b-dihydro-1ah-cyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C([C@@H]2C([C@@H]2CO2)(F)F)C2=C1C(O)=O AFKYQMDFOQZUFV-CGYSWORWSA-N 0.000 claims description 2
• ICNANHHADNBANV-WZKLPCIESA-N (1as,7br)-5-[[2-[(z)-3-(diethylamino)prop-1-enyl]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC=CC=C1S(=O)(=O)NC1=CC=C([C@H]2[C@H](C2)CO2)C2=C1C(O)=O ICNANHHADNBANV-WZKLPCIESA-N 0.000 claims description 2
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