JP2018524343A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- YOELFAVAAZSIJQ-SHACYNPGSA-N (7R)-N-[1-[(2R)-2,3-dihydroxypropyl]-6-fluoro-2-[1-(hydroxymethyl)cyclopropyl]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(CC1)CO)CO YOELFAVAAZSIJQ-SHACYNPGSA-N 0.000 claims 1
- 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
- DSOWYTXOLKTHSW-DXPJPUQTSA-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-DXPJPUQTSA-N 0.000 claims 1
- NMHSSXPMRXNWCT-UHFFFAOYSA-N CN(C(=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)C Chemical compound CN(C(=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)C NMHSSXPMRXNWCT-UHFFFAOYSA-N 0.000 claims 1
- MLIHJZWVFLXBEU-AXECJNCJSA-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-AXECJNCJSA-N 0.000 claims 1
- IHTRGWGXXDBCOP-OXJIQLNZSA-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)I)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)I)F IHTRGWGXXDBCOP-OXJIQLNZSA-N 0.000 claims 1
- CPSJVJMQIQKEHV-UHFFFAOYSA-N FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=NC(=C(C=C1)C)C1=CC(=CC=C1)C(NC)=O)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=NC(=C(C=C1)C)C1=CC(=CC=C1)C(NC)=O)C)F CPSJVJMQIQKEHV-UHFFFAOYSA-N 0.000 claims 1
- JMJWIKIGMKQAFX-UHFFFAOYSA-N FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=NC(=CC=C1)N1CC2CN(CC2C1)C)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)C(CO1)(C(=O)NC1=NC(=CC=C1)N1CC2CN(CC2C1)C)C)F JMJWIKIGMKQAFX-UHFFFAOYSA-N 0.000 claims 1
- OZUMOVGOPNABRV-UHMYUZELSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)N1C[C@@H]([C@H](C1)C1=CC=CC=C1)C(=O)OC)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=CC=CC(=N1)N1C[C@@H]([C@H](C1)C1=CC=CC=C1)C(=O)OC)C)F OZUMOVGOPNABRV-UHMYUZELSA-N 0.000 claims 1
- JKACHELFPOUVND-DEOSSOPVSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=C(C=C1)C)C1=CC=C(C=C1)C(NS(=O)(=O)C)=O)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=C(C=C1)C)C1=CC=C(C=C1)C(NS(=O)(=O)C)=O)C)F JKACHELFPOUVND-DEOSSOPVSA-N 0.000 claims 1
- CLADGBJPABRTCY-JIKORUOASA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CC(CC1)C1=CC=C(C=C1)F)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CC(CC1)C1=CC=C(C=C1)F)C)F CLADGBJPABRTCY-JIKORUOASA-N 0.000 claims 1
- ILGSPRHYIGNNIE-UDRWWJRQSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CC(CC1)S(=O)(=O)C)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CC(CC1)S(=O)(=O)C)C)F ILGSPRHYIGNNIE-UDRWWJRQSA-N 0.000 claims 1
- ZIHHKQLEIOSATG-UDRWWJRQSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CC(OCC1)CO)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CC(OCC1)CO)C)F ZIHHKQLEIOSATG-UDRWWJRQSA-N 0.000 claims 1
- MZWQAXREOWZSEU-IBGZPJMESA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CCCC1)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CCCC1)C)F MZWQAXREOWZSEU-IBGZPJMESA-N 0.000 claims 1
- RKRXRGPWLYJENA-FQEVSTJZSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CCCCC1)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1CCCCC1)C)F RKRXRGPWLYJENA-FQEVSTJZSA-N 0.000 claims 1
- XHRCVUMGVFSPPY-WYRIXSBYSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC(=CC=C1)N1C[C@@H](CC1)O)C)F 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-WYRIXSBYSA-N 0.000 claims 1
- GDDINEVRYQMXRK-IBGZPJMESA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC=C(C=C1)N1CCCC1)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC1=NC=C(C=C1)N1CCCC1)C)F GDDINEVRYQMXRK-IBGZPJMESA-N 0.000 claims 1
- NVLWIYBPVLCSDT-RHGYRFJNSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C(N(N=C(C=1)C1=CC=CC=C1)C[C@@H]([C@@H](CO)O)O)=O)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C(N(N=C(C=1)C1=CC=CC=C1)C[C@@H]([C@@H](CO)O)O)=O)C)F NVLWIYBPVLCSDT-RHGYRFJNSA-N 0.000 claims 1
- FWGHVGSXOFYSBC-QFIPXVFZSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C=C2C=C(NC2=CC=1F)C(CO)(C)C)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C=C2C=C(NC2=CC=1F)C(CO)(C)C)C)F FWGHVGSXOFYSBC-QFIPXVFZSA-N 0.000 claims 1
- MQECRYJRWDLARP-QFIPXVFZSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C=C2C=C(NC2=CC=1F)C1(CCC1)CO)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C=C2C=C(NC2=CC=1F)C1(CCC1)CO)C)F MQECRYJRWDLARP-QFIPXVFZSA-N 0.000 claims 1
- PITKCQKCUZDHHJ-RKLCOFROSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C=NC(=CC=1)N1CC(CC1)O)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1C=NC(=CC=1)N1CC(CC1)O)C)F PITKCQKCUZDHHJ-RKLCOFROSA-N 0.000 claims 1
- PSBSRAKBHCRVSQ-WLRWDXFRSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1N=CC(=NC=1)N1[C@H](C(=O)O)CCC1)C)F Chemical compound FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)NC=1N=CC(=NC=1)N1[C@H](C(=O)O)CCC1)C)F PSBSRAKBHCRVSQ-WLRWDXFRSA-N 0.000 claims 1
- CCKZSNQBSWXOFZ-CVBYOTHMSA-N 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=CC=C(C=N1)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(F)(F)F)C1=CC=C(C=N1)C(=O)O)C)F CCKZSNQBSWXOFZ-CVBYOTHMSA-N 0.000 claims 1
- WUVXQWVXPKOXSE-JYMRHQFYSA-N 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=NC=C(C=C1)CO)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(F)(F)F)C1=NC=C(C=C1)CO)C)F WUVXQWVXPKOXSE-JYMRHQFYSA-N 0.000 claims 1
- WLXSSWNQWYNVHR-GGUMNFRJSA-N 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)C1CCNCC1)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(F)(F)F)C1CCNCC1)C)F WLXSSWNQWYNVHR-GGUMNFRJSA-N 0.000 claims 1
- WZQNDPZOCKJQDQ-WNMGDLKVSA-N 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)[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(F)(F)F)[C@@H]1CC[C@H](CC1)C(=O)O)C)F WZQNDPZOCKJQDQ-WNMGDLKVSA-N 0.000 claims 1
- WEPBBZHGLLKEJS-XUHJDFEOSA-N 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)N1CCC(CC1)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)C1=NC=C(C=C1)C(=O)N1CCC(CC1)O)C)F WEPBBZHGLLKEJS-XUHJDFEOSA-N 0.000 claims 1
- AYXXYMIXJDAYTL-XCIGCYOISA-N 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(C)(C)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)C1=NC=C(C=C1)C(C)(C)O)C)F AYXXYMIXJDAYTL-XCIGCYOISA-N 0.000 claims 1
- NKSPRTUFNXWGBW-SNOBZRMMSA-N 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)CO)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)C1=NC=C(C=C1)CO)C)F NKSPRTUFNXWGBW-SNOBZRMMSA-N 0.000 claims 1
- AQNHESDDLUYRFG-ZIYZLLSTSA-N 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(N=C1)CO)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)C1=NC=C(N=C1)CO)C)F AQNHESDDLUYRFG-ZIYZLLSTSA-N 0.000 claims 1
- QARSDGZHLLCEAL-GIWSNZPPSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=NN=NN1)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)C1=NN=NN1)C)F QARSDGZHLLCEAL-GIWSNZPPSA-N 0.000 claims 1
- VOPKOFYQIQOVID-XKPFWTEKSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C1=NNC(C=C1)=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)C1=NNC(C=C1)=O)C)F VOPKOFYQIQOVID-XKPFWTEKSA-N 0.000 claims 1
- ILZQZLXMDUMACD-KYTVRQNUSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1C=NC(=CC=1)CO)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=1C=NC(=CC=1)CO)C)F ILZQZLXMDUMACD-KYTVRQNUSA-N 0.000 claims 1
- XEWITTWLRAHSCO-IPLFZHMSSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)C=1N=CC(=NC=1)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=1N=CC(=NC=1)C(=O)O)C)F XEWITTWLRAHSCO-IPLFZHMSSA-N 0.000 claims 1
- FFLXDFRJTAHZGO-MEELVIRWSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC)CO)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)CO)C)F FFLXDFRJTAHZGO-MEELVIRWSA-N 0.000 claims 1
- VOPKOFYQIQOVID-MTJJIEKYSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@@H]1C[C@H](OC2=C1C=CC(=C2)OC)C1=NNC(C=C1)=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)C1=NNC(C=C1)=O)C)F VOPKOFYQIQOVID-MTJJIEKYSA-N 0.000 claims 1
- WZQNDPZOCKJQDQ-FZLLVQAISA-N 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)[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(F)(F)F)[C@@H]1CC[C@H](CC1)C(=O)O)C)F WZQNDPZOCKJQDQ-FZLLVQAISA-N 0.000 claims 1
- QHGUNKLFKDIKEF-LCAJTWGOSA-N FC1(OC2=C(O1)C=C1C(=C2)[C@](CO1)(C(=O)N[C@H]1C[C@H](OC2=C1C=CC(=C2)OC)CN1N=CC=CC1=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)CN1N=CC=CC1=O)C)F QHGUNKLFKDIKEF-LCAJTWGOSA-N 0.000 claims 1
- JQXRINCXSQPXHM-NYXPWCLZSA-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-NYXPWCLZSA-N 0.000 claims 1
- MNSCITNYGXTMKY-YJNDVTPQSA-N FC1(OC2=C(O1)C=C1CC[C@@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC(F)(F)F)[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(F)(F)F)[C@@H]1CC[C@H](CC1)C(=O)O)C)F MNSCITNYGXTMKY-YJNDVTPQSA-N 0.000 claims 1
- MNSCITNYGXTMKY-WXOVUVCHSA-N FC1(OC2=C(O1)C=C1CC[C@](C1=C2)(C(=O)N[C@@H]1C[C@@H](OC2=C1C=CC(=C2)OC(F)(F)F)[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(F)(F)F)[C@@H]1CC[C@H](CC1)C(=O)O)C)F MNSCITNYGXTMKY-WXOVUVCHSA-N 0.000 claims 1
- PJNJIZNBLAKBDY-DXPJPUQTSA-N 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(CCOCC1)CO)CO 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(CCOCC1)CO)CO PJNJIZNBLAKBDY-DXPJPUQTSA-N 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562193391P | 2015-07-16 | 2015-07-16 | |
| US62/193,391 | 2015-07-16 | ||
| US201662299633P | 2016-02-25 | 2016-02-25 | |
| US62/299,633 | 2016-02-25 | ||
| PCT/IB2016/054219 WO2017009804A1 (en) | 2015-07-16 | 2016-07-14 | Substituted tricyclics and method of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018524343A JP2018524343A (ja) | 2018-08-30 |
| JP2018524343A5 true JP2018524343A5 (OSRAM) | 2019-08-22 |
| JP6781720B2 JP6781720B2 (ja) | 2020-11-04 |
Family
ID=56418569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017568146A Active JP6781720B2 (ja) | 2015-07-16 | 2016-07-14 | 置換された三環化合物および使用方法 |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US9840513B2 (OSRAM) |
| EP (1) | EP3322697B1 (OSRAM) |
| JP (1) | JP6781720B2 (OSRAM) |
| KR (1) | KR102756919B1 (OSRAM) |
| CN (2) | CN113912617A (OSRAM) |
| AU (1) | AU2016293444B2 (OSRAM) |
| CA (1) | CA2991273C (OSRAM) |
| CL (1) | CL2018000130A1 (OSRAM) |
| CO (1) | CO2018000413A2 (OSRAM) |
| CR (1) | CR20180086A (OSRAM) |
| DO (1) | DOP2018000020A (OSRAM) |
| EC (1) | ECSP18008905A (OSRAM) |
| ES (1) | ES2774066T3 (OSRAM) |
| IL (3) | IL256851B (OSRAM) |
| MX (1) | MX374537B (OSRAM) |
| MY (1) | MY197018A (OSRAM) |
| PE (1) | PE20180608A1 (OSRAM) |
| PH (1) | PH12018500088A1 (OSRAM) |
| RU (1) | RU2744766C2 (OSRAM) |
| SG (1) | SG10202108873RA (OSRAM) |
| TW (1) | TWI712597B (OSRAM) |
| UA (1) | UA122794C2 (OSRAM) |
| WO (1) | WO2017009804A1 (OSRAM) |
| ZA (1) | ZA201800541B (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9840513B2 (en) * | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| CA3016303A1 (en) * | 2016-04-26 | 2017-11-02 | Abbvie S.A.R.L. | Modulators of cystic fibrosis transmembrane conductance regulator protein |
| US10138227B2 (en) | 2016-06-03 | 2018-11-27 | Abbvie S.Á.R.L. | Heteroaryl substituted pyridines and methods of use |
| US10399940B2 (en) | 2016-10-07 | 2019-09-03 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US9981910B2 (en) | 2016-10-07 | 2018-05-29 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US20200123137A1 (en) | 2016-12-20 | 2020-04-23 | AbbVie S.à.r.l. | Deuterated cftr modulators and methods of use |
| TW201831471A (zh) | 2017-02-24 | 2018-09-01 | 盧森堡商艾伯維公司 | 囊腫纖化症跨膜傳導調節蛋白的調節劑及其使用方法 |
| WO2018198052A1 (en) | 2017-04-26 | 2018-11-01 | Oti Lumionics Inc. | Method for patterning a coating on a surface and device including a patterned coating |
| CN106977483A (zh) * | 2017-06-02 | 2017-07-25 | 遵义医学院 | 一种二氟烷基取代的黄酮醇、异黄酮醇和香豆素类化合物的合成方法 |
| US10988454B2 (en) | 2017-09-14 | 2021-04-27 | Abbvie Overseas S.À.R.L. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| WO2019193062A1 (en) | 2018-04-03 | 2019-10-10 | Abbvie S.Á.R.L | Substituted pyrrolidines and their use |
| CN110606840A (zh) * | 2018-06-15 | 2019-12-24 | 日产化学株式会社 | 5-炔基吡啶化合物的制造方法 |
| FR3085825B1 (fr) | 2018-09-14 | 2021-07-16 | Fermentalg | Huile de microorganismes riche en acide docosahexaenoique |
| CN111763198B (zh) * | 2019-04-01 | 2021-09-07 | 新发药业有限公司 | 一种5-取代环丙基甲酰氨基吲哚衍生物的制备方法 |
| TWI848092B (zh) | 2019-04-03 | 2024-07-11 | 美商維泰克斯製藥公司 | 囊腫纖維化跨膜傳導調節蛋白調節劑 |
| KR20220017918A (ko) | 2019-05-08 | 2022-02-14 | 오티아이 루미오닉스 인크. | 핵 생성 억제 코팅 형성용 물질 및 이를 포함하는 디바이스 |
| US11345691B2 (en) | 2019-06-03 | 2022-05-31 | AbbVie Global Enterprises Ltd. | Prodrug modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| US11236067B2 (en) | 2019-07-12 | 2022-02-01 | Orphomed, Inc. | Compound for treating cystic fibrosis |
| CA3150736A1 (en) | 2019-08-14 | 2021-02-18 | Vertex Pharmaceuticals Incorporated | Process of making cftr modulators |
| KR20220064366A (ko) | 2019-08-14 | 2022-05-18 | 버텍스 파마슈티칼스 인코포레이티드 | Cftr 조절제의 결정질 형태 |
| CN111187197B (zh) * | 2020-01-13 | 2021-10-01 | 苏州旺山旺水生物医药有限公司 | 一种Tezacaftor中间体的合成方法 |
| CR20230120A (es) | 2020-08-07 | 2023-09-01 | Vertex Pharma | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| US12324802B2 (en) | 2020-11-18 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| KR20250139404A (ko) | 2020-12-07 | 2025-09-23 | 오티아이 루미오닉스 인크. | 핵 생성 억제 코팅 및 하부 금속 코팅을 사용한 전도성 증착 층의 패턴화 |
| IL303519A (en) | 2020-12-10 | 2023-08-01 | Vertex Pharma | Cystic fibrosis treatment methods |
| WO2022150173A1 (en) | 2021-01-06 | 2022-07-14 | AbbVie Global Enterprises Ltd. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| US20220211692A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| EP4472983A1 (en) | 2022-02-03 | 2024-12-11 | Vertex Pharmaceuticals Incorporated | Methods of preparing and crystalline forms of (6a,12a)-17-amino-12-methyl-6,15-bis(trifluoromethyl)-13,19-dioxa-3,4,18-triazatricyclo[ 12.3.1.12,5]nonadeca-1(18),2,4,14,16-pentaen-6-ol |
| EP4472635A1 (en) | 2022-02-03 | 2024-12-11 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| CN118974059A (zh) | 2022-02-08 | 2024-11-15 | 弗特克斯药品有限公司 | 囊性纤维化跨膜传导调控因子的调节剂 |
| CN119947720A (zh) | 2022-05-16 | 2025-05-06 | 弗特克斯药品有限公司 | 治疗囊性纤维化的方法 |
| WO2025076235A1 (en) | 2023-10-04 | 2025-04-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3583900D1 (de) * | 1984-06-06 | 1991-10-02 | Abbott Lab | Adrenergische verbindungen. |
| US7115553B2 (en) * | 2003-07-10 | 2006-10-03 | International Flavors & Fragrances Inc. | Acetonide fragrance compound |
| WO2005075435A1 (en) * | 2004-01-30 | 2005-08-18 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| US7977322B2 (en) * | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US7939558B2 (en) | 2004-06-04 | 2011-05-10 | The Regents Of The University Of California | Compounds having activity in increasing ion transport by mutant-CFTR and uses thereof |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| HUE032540T2 (en) | 2004-06-24 | 2017-09-28 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
| AR053710A1 (es) * | 2005-04-11 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos espiroheterociclicos y sus usos como agentes terapeuticos |
| MY144968A (en) * | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| US7592461B2 (en) * | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| ES2548292T3 (es) * | 2007-05-25 | 2015-10-15 | Vertex Pharmaceuticals Incorporated | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| PL2444120T3 (pl) | 2007-12-10 | 2018-02-28 | Novartis Ag | Spirocyklicze analogi amiloridu jako blokery ENac |
| CN101925603B (zh) | 2007-12-13 | 2013-12-04 | 沃泰克斯药物股份有限公司 | 囊性纤维化跨膜通道调节因子的调节剂 |
| NZ592504A (en) | 2008-10-23 | 2013-04-26 | Vertex Pharma | Solid forms of n-(4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)phenyl)-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide |
| US8367660B2 (en) | 2008-12-30 | 2013-02-05 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| SG175355A1 (en) * | 2009-04-27 | 2011-12-29 | Elan Pharm Inc | Pyridinone antagonists of alpha-4 integrins |
| AR077252A1 (es) * | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| RS54369B1 (sr) | 2010-10-08 | 2016-04-28 | Nivalis Therapeutics, Inc. | Nova jedinjenja hinolina supstituisana kao inhibitori s-nitrosoglutathione reduktaze |
| ES2558457T3 (es) | 2011-09-16 | 2016-02-04 | Novartis Ag | Compuestos heterocíclicos para el tratamiento de fibrosis quística |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| AU2012312520A1 (en) | 2011-09-20 | 2014-05-08 | The University Of North Carolina At Chapel Hill | Regulation of sodium channels by PLUNC proteins |
| WO2014081821A2 (en) * | 2012-11-20 | 2014-05-30 | Discoverybiomed, Inc. | Small Molecule Bicyclic and Tricyclic CFTR Correctors |
| WO2014180562A1 (en) | 2013-05-07 | 2014-11-13 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of cystic fibrosis |
| US9133210B2 (en) | 2013-08-08 | 2015-09-15 | Galapagos Nv | Compounds and pharmaceutical compositions thereof for the treatment of cystic fibrosis |
| CA2942386A1 (en) | 2014-03-13 | 2015-09-17 | Proteostasis Therapeutics, Inc. | Compounds, compositions, and methods for increasing cftr activity |
| CA2942387A1 (en) | 2014-03-13 | 2015-09-17 | Proteostasis Therapeutics, Inc. | Compounds, compositions and methods of increasing cftr actvity |
| AU2015328174B2 (en) | 2014-10-06 | 2020-05-21 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| HRP20201666T1 (hr) | 2014-10-31 | 2020-12-25 | AbbVie Overseas S.à r.l. | Supstituirani kromani i postupak njihove upotrebe |
| BR112017009194A2 (pt) * | 2014-10-31 | 2017-12-26 | Abbvie Sarl | tetra-hidropiranos substituídos e método de uso |
| US9840513B2 (en) * | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
-
2016
- 2016-07-08 US US15/205,512 patent/US9840513B2/en active Active
- 2016-07-14 CA CA2991273A patent/CA2991273C/en active Active
- 2016-07-14 WO PCT/IB2016/054219 patent/WO2017009804A1/en not_active Ceased
- 2016-07-14 KR KR1020187004637A patent/KR102756919B1/ko active Active
- 2016-07-14 JP JP2017568146A patent/JP6781720B2/ja active Active
- 2016-07-14 PE PE2018000074A patent/PE20180608A1/es unknown
- 2016-07-14 CN CN202111169049.6A patent/CN113912617A/zh active Pending
- 2016-07-14 SG SG10202108873RA patent/SG10202108873RA/en unknown
- 2016-07-14 MY MYPI2018700126A patent/MY197018A/en unknown
- 2016-07-14 CN CN201680053240.5A patent/CN108349930B/zh active Active
- 2016-07-14 EP EP16739584.7A patent/EP3322697B1/en active Active
- 2016-07-14 ES ES16739584T patent/ES2774066T3/es active Active
- 2016-07-14 CR CR20180086A patent/CR20180086A/es unknown
- 2016-07-14 MX MX2018000688A patent/MX374537B/es active IP Right Grant
- 2016-07-14 AU AU2016293444A patent/AU2016293444B2/en active Active
- 2016-07-14 UA UAA201801497A patent/UA122794C2/uk unknown
- 2016-07-14 RU RU2018105684A patent/RU2744766C2/ru active
- 2016-07-15 TW TW105122493A patent/TWI712597B/zh active
-
2017
- 2017-10-17 US US15/786,268 patent/US20180037587A1/en not_active Abandoned
-
2018
- 2018-01-09 PH PH12018500088A patent/PH12018500088A1/en unknown
- 2018-01-11 IL IL256851A patent/IL256851B/en active IP Right Grant
- 2018-01-15 DO DO2018000020A patent/DOP2018000020A/es unknown
- 2018-01-15 CL CL2018000130A patent/CL2018000130A1/es unknown
- 2018-01-17 CO CONC2018/0000413A patent/CO2018000413A2/es unknown
- 2018-01-25 ZA ZA2018/00541A patent/ZA201800541B/en unknown
- 2018-02-07 EC ECIEPI20188905A patent/ECSP18008905A/es unknown
-
2019
- 2019-01-08 US US16/242,460 patent/US20190135827A1/en not_active Abandoned
-
2020
- 2020-04-21 IL IL274112A patent/IL274112B/en unknown
-
2021
- 2021-08-08 IL IL285433A patent/IL285433A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018524343A5 (OSRAM) | ||
| RU2018105684A (ru) | Замещенные трициклические соединения и способ применения | |
| RU2484091C2 (ru) | Производные изоксазоло-пиридина | |
| JPWO2005063743A1 (ja) | チアゾール誘導体 | |
| ES2677996T3 (es) | Nuevas indazolcarboxamidas, procedimiento para su preparación, preparaciones farmacéuticas que contienen las mismas, así como su uso para la preparación de medicamentos | |
| RU2497813C2 (ru) | 4-(4-циано-2-тиоарил)-дигидропиримидиноны и их применение | |
| JP2018530591A5 (OSRAM) | ||
| JP2014062093A5 (OSRAM) | ||
| JP2016517878A5 (OSRAM) | ||
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| JP2013526536A5 (OSRAM) | ||
| JP2012508776A5 (OSRAM) | ||
| JP2006512412A5 (ja) | 神経系の疾患の治療用のベンズアゼピン誘導体 | |
| RU2011146872A (ru) | Производные пролина в качестве ингибиторов катепсина | |
| JPWO2021055744A5 (OSRAM) | ||
| JP2015524798A5 (OSRAM) | ||
| RU2018115722A (ru) | N-СУЛЬФОНИЛИРОВАННЫЕ ПИРАЗОЛО[3,4-b]ПИРИДИН-6-КАРБОКСАМИДЫ И СПОСОБ ИХ ПРИМЕНЕНИЯ | |
| RU2005122932A (ru) | Производные бензазепина для лечения неврологических нарушений | |
| IL295076A (en) | Piperidinone derivatives as mdm2 inhibitors for cancer therapy | |
| IL303196B1 (en) | Heteroaryl substituted pyridines and methods of use | |
| HRP20201469T1 (hr) | Derivati tetrahidroizokinolina | |
| HRP20192323T1 (hr) | Novi derivati dihidrokinolin-2-ona | |
| HRP20171670T1 (hr) | Spojevi i sastavi za moduliranje egfr-aktiviteta | |
| RU2016133684A (ru) | Бициклические азот-содержащие соединения как агонисты М1 мускариновых рецепторов | |
| JP2017530185A5 (OSRAM) |