JP2018524343A5 - - Google Patents
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- Publication number
- JP2018524343A5 JP2018524343A5 JP2017568146A JP2017568146A JP2018524343A5 JP 2018524343 A5 JP2018524343 A5 JP 2018524343A5 JP 2017568146 A JP2017568146 A JP 2017568146A JP 2017568146 A JP2017568146 A JP 2017568146A JP 2018524343 A5 JP2018524343 A5 JP 2018524343A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- methyl
- difluoro
- furo
- 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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- 150000001875 compounds Chemical class 0.000 claims 113
- 229910052739 hydrogen Inorganic materials 0.000 claims 72
- 239000001257 hydrogen Substances 0.000 claims 71
- 150000003839 salts Chemical class 0.000 claims 65
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 61
- -1 C 1 -C 3 alkyl Chemical class 0.000 claims 55
- 229910052736 halogen Inorganic materials 0.000 claims 41
- 150000002367 halogens Chemical class 0.000 claims 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 36
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 33
- UHJCPTUYASMZRC-UHFFFAOYSA-N 1,3-benzodioxole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1OCO2 UHJCPTUYASMZRC-UHFFFAOYSA-N 0.000 claims 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 23
- 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 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 19
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 17
- 125000005605 benzo group Chemical group 0.000 claims 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 11
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- UDKVMASCRFDIIP-UHFFFAOYSA-N 1,7,9,11-tetrahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1CCC(C=C(C(=C3O)C(O)=O)C)=C3C1=C2 UDKVMASCRFDIIP-UHFFFAOYSA-N 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 6
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 235000005152 nicotinamide Nutrition 0.000 claims 5
- 239000011570 nicotinamide Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims 3
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- LETLLRLVJOBSGP-WTGRHJARSA-N 1-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-(trifluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]cyclopropane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC(F)(F)F)C1(CC1)C(=O)O)C)F LETLLRLVJOBSGP-WTGRHJARSA-N 0.000 claims 2
- XCELBSHYOAMWHD-RDGZHIGNSA-N 4-[(2R,4S,6S)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-6-phenyloxan-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](O[C@@H](C1)C1=CC=CC=C1)C1=CC=C(C(=O)O)C=C1)C)F XCELBSHYOAMWHD-RDGZHIGNSA-N 0.000 claims 2
- XCELBSHYOAMWHD-CNBBWRMGSA-N 4-[(2S,4R,6R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-6-phenyloxan-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@H]1C[C@H](O[C@H](C1)C1=CC=CC=C1)C1=CC=C(C(=O)O)C=C1)C)F XCELBSHYOAMWHD-CNBBWRMGSA-N 0.000 claims 2
- FYTHEJLCDOBYCF-VGYIUAJSSA-N 6-[(2R,4R)-7-(difluoromethoxy)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]pyridine-3-carboxylic acid Chemical compound FC(OC1=CC2=C([C@@H](C[C@@H](O2)C2=CC=C(C=N2)C(=O)O)NC(=O)[C@]2(COC=3C2=CC2=C(OC(O2)(F)F)C=3)C)C=C1)F FYTHEJLCDOBYCF-VGYIUAJSSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- MLIHJZWVFLXBEU-OXJIQLNZSA-N FC(OC1=CC2=C([C@@H](C[C@@H](O2)[C@@H]2CC[C@H](CC2)C(=O)O)NC(=O)[C@]2(COC=3C2=CC2=C(OC(O2)(F)F)C=3)C)C=C1)F Chemical compound FC(OC1=CC2=C([C@@H](C[C@@H](O2)[C@@H]2CC[C@H](CC2)C(=O)O)NC(=O)[C@]2(COC=3C2=CC2=C(OC(O2)(F)F)C=3)C)C=C1)F MLIHJZWVFLXBEU-OXJIQLNZSA-N 0.000 claims 2
- JQXRINCXSQPXHM-NBVYDZSDSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)[C@@H]1CC[C@H](CC1)C(=O)O)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)[C@@H]1CC[C@H](CC1)C(=O)O)C)F JQXRINCXSQPXHM-NBVYDZSDSA-N 0.000 claims 2
- MRDCHUMTOVHGTH-BLJTZWMSSA-N FC1(OC2=C(O1)C=C1CC[C@@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)[C@@H]1CC[C@H](CC1)C(=O)O)C)F Chemical compound FC1(OC2=C(O1)C=C1CC[C@@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)[C@@H]1CC[C@H](CC1)C(=O)O)C)F MRDCHUMTOVHGTH-BLJTZWMSSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003623 enhancer Substances 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- ZISXZTPZHZYSFN-UAPALYRASA-N (3R)-1-[6-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]pyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=CC=CC(=N1)N1C[C@@H](CC1)C(=O)O)C)F ZISXZTPZHZYSFN-UAPALYRASA-N 0.000 claims 1
- ZISXZTPZHZYSFN-GIPWTMENSA-N (3R)-1-[6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)N1C[C@@H](CC1)C(=O)O)C)F ZISXZTPZHZYSFN-GIPWTMENSA-N 0.000 claims 1
- ZISXZTPZHZYSFN-YBTHPKLGSA-N (3S)-1-[6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)N1C[C@H](CC1)C(=O)O)C)F ZISXZTPZHZYSFN-YBTHPKLGSA-N 0.000 claims 1
- ILGSPRHYIGNNIE-ODXCJYRJSA-N (7R)-2,2-difluoro-7-methyl-N-[6-[(3R)-3-methylsulfonylpyrrolidin-1-yl]pyridin-2-yl]-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1C[C@@H](CC1)S(=O)(=O)C)C)F ILGSPRHYIGNNIE-ODXCJYRJSA-N 0.000 claims 1
- PEXQZXQHXXVHTE-XUHJDFEOSA-N (7R)-2,2-difluoro-N-[(2R,4R)-7-methoxy-2-(6-phenylmethoxypyridazin-3-yl)-3,4-dihydro-2H-chromen-4-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)OC1=CC=C(N=N1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC PEXQZXQHXXVHTE-XUHJDFEOSA-N 0.000 claims 1
- QNPSNBNFGVREGB-VVDSWQSDSA-N (7R)-2,2-difluoro-N-[(2R,4R)-7-methoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-chromen-4-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)OC[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC QNPSNBNFGVREGB-VVDSWQSDSA-N 0.000 claims 1
- QFHBWTLHMZMCEN-QPFIFXANSA-N (7R)-2,2-difluoro-N-[(2R,4R)-7-methoxy-2-[5-(morpholine-4-carbonyl)pyridin-2-yl]-3,4-dihydro-2H-chromen-4-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=NC=C(C=C1)C(=O)N1CCOCC1)C)F QFHBWTLHMZMCEN-QPFIFXANSA-N 0.000 claims 1
- PEXQZXQHXXVHTE-SFPIMLNGSA-N (7R)-2,2-difluoro-N-[(2S,4R)-7-methoxy-2-(6-phenylmethoxypyridazin-3-yl)-3,4-dihydro-2H-chromen-4-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)OC1=CC=C(N=N1)[C@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC PEXQZXQHXXVHTE-SFPIMLNGSA-N 0.000 claims 1
- QNPSNBNFGVREGB-FGJOCGMUSA-N (7R)-2,2-difluoro-N-[(2S,4S)-7-methoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-chromen-4-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)OC[C@H]1OC2=C([C@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC QNPSNBNFGVREGB-FGJOCGMUSA-N 0.000 claims 1
- XHRCVUMGVFSPPY-WLRWDXFRSA-N (7R)-2,2-difluoro-N-[6-[(3S)-3-hydroxypyrrolidin-1-yl]pyridin-2-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1C[C@H](CC1)O)C)F XHRCVUMGVFSPPY-WLRWDXFRSA-N 0.000 claims 1
- QXJSNGXOKUTSMM-LJAQVGFWSA-N (7R)-2,2-difluoro-N-[6-fluoro-2-(2-methyl-1-phenylmethoxypropan-2-yl)-1H-indol-5-yl]-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)OCC(C)(C)C=1NC2=CC(=C(C=C2C=1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)F QXJSNGXOKUTSMM-LJAQVGFWSA-N 0.000 claims 1
- CSIOQDOEGYDFCA-QFIPXVFZSA-N (7R)-N-(2-tert-butyl-1H-indol-5-yl)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C)(C)(C)C=1NC2=CC=C(C=C2C=1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C CSIOQDOEGYDFCA-QFIPXVFZSA-N 0.000 claims 1
- CYZQMPCPXDFZAQ-INIZCTEOSA-N (7R)-N-(6-chloro-5-methylpyridin-2-yl)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound ClC1=C(C=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C CYZQMPCPXDFZAQ-INIZCTEOSA-N 0.000 claims 1
- UWPOEOXABXHDRN-VGTADKHUSA-N (7R)-N-[(2R,4R)-2-(1-benzyltetrazol-5-yl)-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=NN=C1[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC UWPOEOXABXHDRN-VGTADKHUSA-N 0.000 claims 1
- YSFMNEHGDWYHJC-LXHIVTORSA-N (7R)-N-[(2R,4R)-2-(5-acetylpyridin-2-yl)-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C)(=O)C=1C=CC(=NC=1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC YSFMNEHGDWYHJC-LXHIVTORSA-N 0.000 claims 1
- FBGLCWZDKJTCEJ-JLCUDIMXSA-N (7R)-N-[(2R,4R)-2-(5-chloropyrazin-2-yl)-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound ClC=1N=CC(=NC=1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC FBGLCWZDKJTCEJ-JLCUDIMXSA-N 0.000 claims 1
- IRJJHRSBEWJOMD-WTSFKKHRSA-N (7R)-N-[(2R,4R)-2-(5-ethenylpyrazin-2-yl)-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(=C)C=1N=CC(=NC=1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC IRJJHRSBEWJOMD-WTSFKKHRSA-N 0.000 claims 1
- GTVRGHWZBVNPIG-GAKIBJFNSA-N (7R)-N-[(2R,4R)-2-(6-bromopyridin-3-yl)-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound BrC1=CC=C(C=N1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC GTVRGHWZBVNPIG-GAKIBJFNSA-N 0.000 claims 1
- WQYGFKITCNIREP-XKPFWTEKSA-N (7R)-N-[(2R,4R)-2-(6-chloropyridazin-3-yl)-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound ClC1=CC=C(N=N1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC WQYGFKITCNIREP-XKPFWTEKSA-N 0.000 claims 1
- YFXFDXQNTDWVHP-GQIGMWPISA-N (7R)-N-[(2R,4R)-2-[4-(4,4-difluoropiperidine-1-carbonyl)phenyl]-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound FC1(CCN(CC1)C(=O)C1=CC=C(C=C1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC)F YFXFDXQNTDWVHP-GQIGMWPISA-N 0.000 claims 1
- GODUAFVFBRPXRL-YYSRDSISSA-N (7R)-N-[(2R,4R)-2-[5-(1,2-dihydroxyethyl)pyrazin-2-yl]-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound OC(CO)C=1N=CC(=NC=1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC GODUAFVFBRPXRL-YYSRDSISSA-N 0.000 claims 1
- GODUAFVFBRPXRL-WIWWCEQTSA-N (7R)-N-[(2R,4R)-2-[5-[(1R)-1,2-dihydroxyethyl]pyrazin-2-yl]-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@@H](CO)C=1N=CC(=NC=1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC GODUAFVFBRPXRL-WIWWCEQTSA-N 0.000 claims 1
- GODUAFVFBRPXRL-KJMMEZDOSA-N (7R)-N-[(2R,4R)-2-[5-[(1S)-1,2-dihydroxyethyl]pyrazin-2-yl]-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CO)C=1N=CC(=NC=1)[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC GODUAFVFBRPXRL-KJMMEZDOSA-N 0.000 claims 1
- GBJGRMPSWZHOQB-VAABHJITSA-N (7R)-N-[(2R,4R)-2-[[(2R)-2,3-dihydroxypropoxy]methyl]-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@@H](COC[C@@H]1OC2=C([C@@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC)CO GBJGRMPSWZHOQB-VAABHJITSA-N 0.000 claims 1
- GBJGRMPSWZHOQB-CPIZZJQMSA-N (7R)-N-[(2S,4S)-2-[[(2R)-2,3-dihydroxypropoxy]methyl]-7-methoxy-3,4-dihydro-2H-chromen-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@@H](COC[C@H]1OC2=C([C@H](C1)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C=CC(=C2)OC)CO GBJGRMPSWZHOQB-CPIZZJQMSA-N 0.000 claims 1
- OPEJBCYWUNQXDF-GYCJOSAFSA-N (7R)-N-[1-[(2R)-2,3-dihydroxypropyl]-2-oxo-5-phenylpyridin-3-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C(C(=CC(=C1)C1=CC=CC=C1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)=O)CO OPEJBCYWUNQXDF-GYCJOSAFSA-N 0.000 claims 1
- QHLRLZOVWCLGKH-PWECECGKSA-N (7R)-N-[1-[(2R)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C(=CC2=CC(=C(C=C12)F)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C(CO)(C)C)CO QHLRLZOVWCLGKH-PWECECGKSA-N 0.000 claims 1
- DOECVGQDYIBDGI-PWECECGKSA-N (7R)-N-[1-[(2R)-2,3-dihydroxypropyl]-6-fluoro-2-(3-methyloxetan-3-yl)indol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C(=CC2=CC(=C(C=C12)F)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1(COC1)C)CO DOECVGQDYIBDGI-PWECECGKSA-N 0.000 claims 1
- FSJZWTJUOTWKQD-BZQUYTCOSA-N (7R)-N-[1-[(2R)-2,3-dihydroxypropyl]-6-fluoro-2-[1-(hydroxymethyl)cyclobutyl]indol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C(=CC2=CC(=C(C=C12)F)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1(CCC1)CO)CO FSJZWTJUOTWKQD-BZQUYTCOSA-N 0.000 claims 1
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- AUPTXKHDHQHZKN-SHACYNPGSA-N (7R)-N-[1-[(2R)-2,3-dihydroxypropyl]-6-fluoro-2-[3-(hydroxymethyl)oxetan-3-yl]indol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C(=CC2=CC(=C(C=C12)F)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1(COC1)CO)CO AUPTXKHDHQHZKN-SHACYNPGSA-N 0.000 claims 1
- ZSBXSCGIZFZMND-HAWMADMCSA-N (7R)-N-[1-[(2S)-3-cyano-2-hydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(#N)C[C@@H](CN1C(=CC2=CC(=C(C=C12)F)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C(CO)(C)C)O ZSBXSCGIZFZMND-HAWMADMCSA-N 0.000 claims 1
- CSYDWXFDARFSPX-FATZIPQQSA-N (7R)-N-[2-[(2R)-2,3-dihydroxypropyl]-3-oxo-6-phenylpyridazin-4-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1N=C(C=C(C1=O)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1=CC=CC=C1)CO CSYDWXFDARFSPX-FATZIPQQSA-N 0.000 claims 1
- GLXXSZLPIOXCHA-PWECECGKSA-N (7R)-N-[2-tert-butyl-1-[(2R)-2,3-dihydroxypropyl]-6-fluoroindol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C)(C)(C)C=1N(C2=CC(=C(C=C2C=1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)F)C[C@H](CO)O GLXXSZLPIOXCHA-PWECECGKSA-N 0.000 claims 1
- AODKAKLGENMABW-SUMNFNSASA-N (7R)-N-[5-[(2R)-2,3-dihydroxypropyl]-7-fluoro-1,1,4,4-tetramethyl-3H-pyrano[4,3-b]indol-8-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C2=C(C=3C=C(C(=CC1=3)F)NC(=O)[C@]1(COC=3C1=CC1=C(OC(O1)(F)F)C=3)C)C(OCC2(C)C)(C)C)CO AODKAKLGENMABW-SUMNFNSASA-N 0.000 claims 1
- WFWUVPORXIMFJZ-MGNBDDOMSA-N (7R)-N-[5-bromo-1-[(2R)-2,3-dihydroxypropyl]-2-oxopyridin-3-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound BrC=1C=C(C(N(C=1)C[C@H](CO)O)=O)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C WFWUVPORXIMFJZ-MGNBDDOMSA-N 0.000 claims 1
- CLBIUDWZZAWHIK-NRFANRHFSA-N (7R)-N-[6-(3,3-dimethylpyrrolidin-1-yl)pyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound CC1(CN(CC1)C1=CC=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C CLBIUDWZZAWHIK-NRFANRHFSA-N 0.000 claims 1
- CINJZGHNQSKLNM-IHZSNKTASA-N (7R)-N-[6-(3-benzylpyrrolidin-1-yl)pyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(C1=CC=CC=C1)C1CN(CC1)C1=CC=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C CINJZGHNQSKLNM-IHZSNKTASA-N 0.000 claims 1
- FZFNCGNJYLSTJL-QHCPKHFHSA-N (7R)-N-[6-(3-cyanophenyl)-5-methylpyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)C1=C(C=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C FZFNCGNJYLSTJL-QHCPKHFHSA-N 0.000 claims 1
- MUFNRIHRQACTFC-UCSBTNPJSA-N (7R)-N-[6-[3-(1,2-dihydroxyethyl)phenyl]-5-methylpyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound OC(CO)C=1C=C(C=CC=1)C1=C(C=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C MUFNRIHRQACTFC-UCSBTNPJSA-N 0.000 claims 1
- CFZQHLPHOTYPDO-VWLOTQADSA-N (7R)-N-[6-[3-(cyclopropylsulfamoyl)phenyl]-5-methylpyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound C1(CC1)NS(=O)(=O)C=1C=C(C=CC=1)C1=C(C=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C CFZQHLPHOTYPDO-VWLOTQADSA-N 0.000 claims 1
- OGMRGCMUMBRGBI-MGNBDDOMSA-N (7R)-N-[6-[[(2R)-2,3-dihydroxypropyl]amino]pyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CNC1=CC=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)CO OGMRGCMUMBRGBI-MGNBDDOMSA-N 0.000 claims 1
- OGMRGCMUMBRGBI-YPMLDQLKSA-N (7R)-N-[6-[[(2S)-2,3-dihydroxypropyl]amino]pyridin-2-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@@H](CNC1=CC=CC(=N1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)CO OGMRGCMUMBRGBI-YPMLDQLKSA-N 0.000 claims 1
- QHLRLZOVWCLGKH-DLUDVSRJSA-N (7S)-N-[1-[(2R)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound O[C@H](CN1C(=CC2=CC(=C(C=C12)F)NC(=O)[C@@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C(CO)(C)C)CO QHLRLZOVWCLGKH-DLUDVSRJSA-N 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- LETLLRLVJOBSGP-DVXDUOKCSA-N 1-[(2S,4S)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-(trifluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]cyclopropane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@H]1C[C@H](OC2=C1C=CC(=C2)OC(F)(F)F)C1(CC1)C(=O)O)C)F LETLLRLVJOBSGP-DVXDUOKCSA-N 0.000 claims 1
- OCCHSDZZHVPQLN-UHFFFAOYSA-N 1-[2-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-4-(trifluoromethyl)phenyl]-5-methylimidazole-4-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=C(C=CC(=C1)C(F)(F)F)N1C=NC(=C1C)C(=O)O)C)F OCCHSDZZHVPQLN-UHFFFAOYSA-N 0.000 claims 1
- CTUVGOOYYNJCKN-UHFFFAOYSA-N 1-[4-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]phenyl]azetidine-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=CC=C(C=C1)N1CC(C1)C(=O)O)C)F CTUVGOOYYNJCKN-UHFFFAOYSA-N 0.000 claims 1
- XNWFKBKPBMAQID-UHFFFAOYSA-N 1-[6-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]pyridin-2-yl]piperidine-4-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=CC=CC(=N1)N1CCC(CC1)C(=O)O)C)F XNWFKBKPBMAQID-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- VLXFFUHFSAZXAE-UHFFFAOYSA-N 2,2-difluoro-7-methyl-N-[3-(2-methylphenyl)phenyl]-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound CC1=C(C=CC=C1)C1=CC(=CC=C1)NC(=O)C1(COC2=CC3=C(OC(O3)(F)F)C=C21)C VLXFFUHFSAZXAE-UHFFFAOYSA-N 0.000 claims 1
- XGUUCHSSKBGTBQ-UHFFFAOYSA-N 2,2-difluoro-7-methyl-N-[6-[2-(2-methylpropyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]pyridin-2-yl]-6H-furo[2,3-f][1,3]benzodioxole-7-carboxamide Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=NC(=CC=C1)N1CC2CN(CC2C1)CC(C)C)C)F XGUUCHSSKBGTBQ-UHFFFAOYSA-N 0.000 claims 1
- ZUTKQIAXPSSHEJ-UDCNLSRBSA-N 2-[4-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-(trifluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]piperidin-1-yl]acetic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC(F)(F)F)C1CCN(CC1)CC(=O)O)C)F ZUTKQIAXPSSHEJ-UDCNLSRBSA-N 0.000 claims 1
- ZUTKQIAXPSSHEJ-DGUDUIIESA-N 2-[4-[(2S,4S)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-(trifluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]piperidin-1-yl]acetic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@H]1C[C@H](OC2=C1C=CC(=C2)OC(F)(F)F)C1CCN(CC1)CC(=O)O)C)F ZUTKQIAXPSSHEJ-DGUDUIIESA-N 0.000 claims 1
- CWBFAWUUIKMIEB-LDZFZAOSSA-N 2-[6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-3a-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)N1CC2C(C1)(CCC2)C(=O)O)C)F CWBFAWUUIKMIEB-LDZFZAOSSA-N 0.000 claims 1
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 1
- VFLCKHONONAZNO-ULBABTNWSA-N 3-[(2R,4R)-4-[(2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl)amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CCC(C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC=C2)C=1C=C(C(=O)O)C=CC=1)C)F VFLCKHONONAZNO-ULBABTNWSA-N 0.000 claims 1
- SFUNDRYMOKYQFR-GNRAYRMUSA-N 3-[(2R,4R)-4-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC=C2)C=1C=C(C(=O)O)C=CC=1)C)F SFUNDRYMOKYQFR-GNRAYRMUSA-N 0.000 claims 1
- METLPCKTONDGGC-RZDHNTQGSA-N 3-[(2R,4R)-4-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=C(C(=O)O)C=CC=1)C)F METLPCKTONDGGC-RZDHNTQGSA-N 0.000 claims 1
- IGRTYEKPIZMUFM-DQCZWYHMSA-N 3-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CC[C@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=C(C(=O)O)C=CC=1)C)F IGRTYEKPIZMUFM-DQCZWYHMSA-N 0.000 claims 1
- METLPCKTONDGGC-DVHCVUMVSA-N 3-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=C(C(=O)O)C=CC=1)C)F METLPCKTONDGGC-DVHCVUMVSA-N 0.000 claims 1
- IGRTYEKPIZMUFM-XJGOYTCSSA-N 3-[(2R,4R)-4-[[(7S)-2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CC[C@@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=C(C(=O)O)C=CC=1)C)F IGRTYEKPIZMUFM-XJGOYTCSSA-N 0.000 claims 1
- METLPCKTONDGGC-SEXOINJZSA-N 3-[(2R,4R)-4-[[(7S)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=C(C(=O)O)C=CC=1)C)F METLPCKTONDGGC-SEXOINJZSA-N 0.000 claims 1
- KICNTJMDMGYQAO-UHFFFAOYSA-N 3-[2-methyl-5-[(6-methyl-7,8-dihydrocyclopenta[g][1,3]benzodioxole-6-carbonyl)amino]phenyl]benzoic acid Chemical compound CC1=C(C=C(C=C1)NC(=O)C1(CCC2=C1C=CC1=C2OCO1)C)C1=CC(=CC=C1)C(=O)O KICNTJMDMGYQAO-UHFFFAOYSA-N 0.000 claims 1
- KICNTJMDMGYQAO-AREMUKBSSA-N 3-[2-methyl-5-[[(6R)-6-methyl-7,8-dihydrocyclopenta[g][1,3]benzodioxole-6-carbonyl]amino]phenyl]benzoic acid Chemical compound CC1=C(C=C(C=C1)NC(=O)[C@@]1(CCC2=C1C=CC1=C2OCO1)C)C1=CC(=CC=C1)C(=O)O KICNTJMDMGYQAO-AREMUKBSSA-N 0.000 claims 1
- KICNTJMDMGYQAO-SANMLTNESA-N 3-[2-methyl-5-[[(6S)-6-methyl-7,8-dihydrocyclopenta[g][1,3]benzodioxole-6-carbonyl]amino]phenyl]benzoic acid Chemical compound CC1=C(C=C(C=C1)NC(=O)[C@]1(CCC2=C1C=CC1=C2OCO1)C)C1=CC(=CC=C1)C(=O)O KICNTJMDMGYQAO-SANMLTNESA-N 0.000 claims 1
- NIUZDZYQWGTVGA-QFIPXVFZSA-N 3-[3-chloro-6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]benzoic acid Chemical compound ClC=1C(=NC(=CC=1)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C=1C=C(C(=O)O)C=CC=1 NIUZDZYQWGTVGA-QFIPXVFZSA-N 0.000 claims 1
- VBHXBKHTBAOOBD-UHFFFAOYSA-N 3-[5-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-2-methylphenyl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC=1C=CC(=C(C=1)C1=CC(=CC=C1)C(=O)O)C)C)F VBHXBKHTBAOOBD-UHFFFAOYSA-N 0.000 claims 1
- JEHBHRSKGCPPOU-UHFFFAOYSA-N 3-[6-[(2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl)amino]-3-methylpyridin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CCC(C1=C2)(C(=O)NC1=CC=C(C(=N1)C=1C=C(C(=O)O)C=CC=1)C)C)F JEHBHRSKGCPPOU-UHFFFAOYSA-N 0.000 claims 1
- NLOIBZQBHDRSKP-UHFFFAOYSA-N 3-[6-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-3-methylpyridin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=CC=C(C(=N1)C=1C=C(C(=O)O)C=CC=1)C)C)F NLOIBZQBHDRSKP-UHFFFAOYSA-N 0.000 claims 1
- MTRQCQNUWYBZDT-QFIPXVFZSA-N 3-[6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]-2-fluorobenzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)C=1C(=C(C(=O)O)C=CC=1)F)C)F MTRQCQNUWYBZDT-QFIPXVFZSA-N 0.000 claims 1
- NROGWJDOKCSICE-QHCPKHFHSA-N 3-[6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]-2-methylbenzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)C=1C(=C(C(=O)O)C=CC=1)C)C)F NROGWJDOKCSICE-QHCPKHFHSA-N 0.000 claims 1
- OVADFDUASFLCKE-SGRNYHPWSA-N 4-[(2R,4R)-4-[(2,2-difluoro-6-methyl-7H-furo[3,2-g][1,3]benzodioxole-6-carbonyl)amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C1=C(C=C2)C(CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=CC=C(C(=O)O)C=C1)C)F OVADFDUASFLCKE-SGRNYHPWSA-N 0.000 claims 1
- UGWNLFKZMZYLFI-RZDHNTQGSA-N 4-[(2R,4R)-4-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=CC=C(C(=O)O)C=C1)C)F UGWNLFKZMZYLFI-RZDHNTQGSA-N 0.000 claims 1
- KZVMALZPFISKPG-AJFLCOCNSA-N 4-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CC[C@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC=C2)C1=CC=C(C(=O)O)C=C1)C)F KZVMALZPFISKPG-AJFLCOCNSA-N 0.000 claims 1
- XRLHEEGTBVYTFL-DQCZWYHMSA-N 4-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CC[C@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=CC=C(C(=O)O)C=C1)C)F XRLHEEGTBVYTFL-DQCZWYHMSA-N 0.000 claims 1
- NNTGHJJEVYQBLQ-KYTVRQNUSA-N 4-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-1,2,3,4-tetrahydroquinolin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](NC2=CC=CC=C12)C1=CC=C(C(=O)O)C=C1)C)F NNTGHJJEVYQBLQ-KYTVRQNUSA-N 0.000 claims 1
- NONBZWUUKODXJG-DZTNWFRXSA-N 4-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC=C2)C1=CC=C(C(=O)O)C=C1)C)F NONBZWUUKODXJG-DZTNWFRXSA-N 0.000 claims 1
- UGWNLFKZMZYLFI-DVHCVUMVSA-N 4-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=CC=C(C(=O)O)C=C1)C)F UGWNLFKZMZYLFI-DVHCVUMVSA-N 0.000 claims 1
- KZVMALZPFISKPG-NTOOTBGVSA-N 4-[(2R,4R)-4-[[(7S)-2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CC[C@@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC=C2)C1=CC=C(C(=O)O)C=C1)C)F KZVMALZPFISKPG-NTOOTBGVSA-N 0.000 claims 1
- XRLHEEGTBVYTFL-XJGOYTCSSA-N 4-[(2R,4R)-4-[[(7S)-2,2-difluoro-7-methyl-5,6-dihydrocyclopenta[f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1CC[C@@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=CC=C(C(=O)O)C=C1)C)F XRLHEEGTBVYTFL-XJGOYTCSSA-N 0.000 claims 1
- UGWNLFKZMZYLFI-SEXOINJZSA-N 4-[(2R,4R)-4-[[(7S)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=CC=C(C(=O)O)C=C1)C)F UGWNLFKZMZYLFI-SEXOINJZSA-N 0.000 claims 1
- JQXRINCXSQPXHM-LUZGGZDYSA-N 4-[(2R,4R)-4-[[(7S)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]cyclohexane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1CCC(CC1)C(=O)O)C)F JQXRINCXSQPXHM-LUZGGZDYSA-N 0.000 claims 1
- IOAHUMJRUHUSAG-KFDHSVMUSA-N 4-[(2R,4R)-7-(difluoromethoxy)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound FC(OC1=CC2=C([C@@H](C[C@@H](O2)C2=CC=C(C(=O)O)C=C2)NC(=O)[C@]2(COC=3C2=CC2=C(OC(O2)(F)F)C=3)C)C=C1)F IOAHUMJRUHUSAG-KFDHSVMUSA-N 0.000 claims 1
- UXGNDIZHJQDFEZ-VNZAXJPBSA-N 4-[(2R,4R)-7-methoxy-4-[[(6R)-6-methyl-7,8-dihydrocyclopenta[g][1,3]benzodioxole-6-carbonyl]amino]-3,4-dihydro-2H-chromen-2-yl]benzoic acid Chemical compound COC1=CC2=C([C@@H](C[C@@H](O2)C2=CC=C(C(=O)O)C=C2)NC(=O)[C@@]2(CCC3=C2C=CC2=C3OCO2)C)C=C1 UXGNDIZHJQDFEZ-VNZAXJPBSA-N 0.000 claims 1
- PNCCXFWWVSHZNA-KPSBJNRCSA-N 4-[(2R,4S,6R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-6-methyloxan-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](O[C@@H](C1)C)C1=CC=C(C(=O)O)C=C1)C)F PNCCXFWWVSHZNA-KPSBJNRCSA-N 0.000 claims 1
- PNCCXFWWVSHZNA-GMJNZJHOSA-N 4-[(2S,4R,6S)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-6-methyloxan-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@H]1C[C@H](O[C@H](C1)C)C1=CC=C(C(=O)O)C=C1)C)F PNCCXFWWVSHZNA-GMJNZJHOSA-N 0.000 claims 1
- NNTGHJJEVYQBLQ-DYLHXGEVSA-N 4-[(2S,4S)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-1,2,3,4-tetrahydroquinolin-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@H]1C[C@H](NC2=CC=CC=C12)C1=CC=C(C(=O)O)C=C1)C)F NNTGHJJEVYQBLQ-DYLHXGEVSA-N 0.000 claims 1
- JQXRINCXSQPXHM-WFGDATFFSA-N 4-[(2S,4S)-4-[[(7S)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]cyclohexane-1-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@@](CO1)(C(=O)N[C@H]1C[C@H](OC2=C1C=CC(=C2)OC)C1CCC(CC1)C(=O)O)C)F JQXRINCXSQPXHM-WFGDATFFSA-N 0.000 claims 1
- YQBULFHOCLQJIN-UHFFFAOYSA-N 4-[2-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-1,3-thiazol-4-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC=1SC=C(N=1)C1=CC=C(C(=O)O)C=C1)C)F YQBULFHOCLQJIN-UHFFFAOYSA-N 0.000 claims 1
- LVFAFGZHYRPWFU-UHFFFAOYSA-N 4-[3-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]phenyl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC=1C=C(C=CC=1)C1=CC=C(C=C1)C(=O)O)C)F LVFAFGZHYRPWFU-UHFFFAOYSA-N 0.000 claims 1
- JXYAWUZKZOLTMN-UHFFFAOYSA-N 4-[3-cyclopropyl-5-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-6-oxopyridazin-1-yl]benzoic acid Chemical compound C1(CC1)C1=NN(C(C(=C1)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)=O)C1=CC=C(C(=O)O)C=C1 JXYAWUZKZOLTMN-UHFFFAOYSA-N 0.000 claims 1
- LOLBNMQASHEPPR-UHFFFAOYSA-N 4-[5-[(2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino]-1,3,4-thiadiazol-2-yl]benzoic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=NN=C(S1)C1=CC=C(C(=O)O)C=C1)C)F LOLBNMQASHEPPR-UHFFFAOYSA-N 0.000 claims 1
- QSSPSNXRJPGZND-QFIPXVFZSA-N 4-[5-bromo-3-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-2-oxopyridin-1-yl]benzoic acid Chemical compound BrC=1C=C(C(N(C=1)C1=CC=C(C(=O)O)C=C1)=O)NC(=O)[C@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C QSSPSNXRJPGZND-QFIPXVFZSA-N 0.000 claims 1
- QECYAQPSHOPOBS-UDCNLSRBSA-N 5-[(2R,4R)-4-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]pyridine-2-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=CC(=NC=1)C(=O)O)C)F QECYAQPSHOPOBS-UDCNLSRBSA-N 0.000 claims 1
- OESAZVMKPVTFPV-FQEVSTJZSA-N 5-[6-[[(7R)-2,2-difluoro-7-methyl-6H-furo[2,3-f][1,3]benzodioxole-7-carbonyl]amino]pyridin-2-yl]thiophene-3-carboxylic acid Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)C1=CC(=CS1)C(=O)O)C)F OESAZVMKPVTFPV-FQEVSTJZSA-N 0.000 claims 1
- GHBMCHCPTGPRTI-OXJIQLNZSA-N BrC=1C(=CC2=C([C@@H](C[C@@H](O2)[C@@H]2CC[C@H](CC2)C(=O)O)NC(=O)[C@]2(COC=3C2=CC2=C(OC(O2)(F)F)C=3)C)C=1)OC Chemical compound BrC=1C(=CC2=C([C@@H](C[C@@H](O2)[C@@H]2CC[C@H](CC2)C(=O)O)NC(=O)[C@]2(COC=3C2=CC2=C(OC(O2)(F)F)C=3)C)C=1)OC GHBMCHCPTGPRTI-OXJIQLNZSA-N 0.000 claims 1
- WGJZDEWHMQJLJV-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C=1N=C(SC=1)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C Chemical compound C(#N)C1=CC=C(C=C1)C=1N=C(SC=1)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C WGJZDEWHMQJLJV-UHFFFAOYSA-N 0.000 claims 1
- SXAXOELQCZBHIS-UHFFFAOYSA-N C(N)(=O)C=1C=C(C=CC=1)C1=C(C=CC(=N1)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C Chemical compound C(N)(=O)C=1C=C(C=CC=1)C1=C(C=CC(=N1)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C SXAXOELQCZBHIS-UHFFFAOYSA-N 0.000 claims 1
- DSOWYTXOLKTHSW-DIERRCTGSA-N CC1(OC[C@H](O1)CN1N=C(C=C(C1=O)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1=CC=CC=C1)C Chemical compound CC1(OC[C@H](O1)CN1N=C(C=C(C1=O)NC(=O)C1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1=CC=CC=C1)C DSOWYTXOLKTHSW-DIERRCTGSA-N 0.000 claims 1
- DSOWYTXOLKTHSW-AKJBCIBTSA-N CC1(OC[C@H](O1)CN1N=C(C=C(C1=O)NC(=O)[C@@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1=CC=CC=C1)C Chemical compound CC1(OC[C@H](O1)CN1N=C(C=C(C1=O)NC(=O)[C@@]1(COC=2C1=CC1=C(OC(O1)(F)F)C=2)C)C1=CC=CC=C1)C DSOWYTXOLKTHSW-AKJBCIBTSA-N 0.000 claims 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 claims 1
- 0 C*(C)[C@@](*)(C*c1c2*)c1c(*)c1c2OC(*)(O)O1 Chemical compound C*(C)[C@@](*)(C*c1c2*)c1c(*)c1c2OC(*)(O)O1 0.000 description 1
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| WO2019193062A1 (en) | 2018-04-03 | 2019-10-10 | Abbvie S.Á.R.L | Substituted pyrrolidines and their use |
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