HUE025363T2 - Indanyl Oxide Hydrobenzofuranylacetic Acids that can be used to treat metabolic syndrome - Google Patents

Info

Publication number

HUE025363T2

HUE025363T2 HUE11788845A HUE11788845A HUE025363T2 HU E025363 T2 HUE025363 T2 HU E025363T2 HU E11788845 A HUE11788845 A HU E11788845A HU E11788845 A HUE11788845 A HU E11788845A HU E025363 T2 HUE025363 T2 HU E025363T2

Authority

HU

Hungary

Prior art keywords

indan

alkyl

groups

acetic acid

benzofuran

Prior art date

2010-12-01

Links

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• Global Dossier
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• 238000011282 treatment Methods 0.000 title claims description 29
• 208000001145 Metabolic Syndrome Diseases 0.000 title claims description 6
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 title claims description 6
• RSYYSLLENSVCGM-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-2-yl)-2-(2,3-dihydro-1h-inden-1-yloxy)acetic acid Chemical class C1C2=CC=CC=C2OC1C(C(=O)O)OC1C2=CC=CC=C2CC1 RSYYSLLENSVCGM-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 430
• -1 cyano, nitro, amino Chemical group 0.000 claims description 234
• 125000005842 heteroatom Chemical group 0.000 claims description 87
• 229910052731 fluorine Inorganic materials 0.000 claims description 80
• 229910052801 chlorine Inorganic materials 0.000 claims description 71
• 229910052794 bromium Inorganic materials 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• 150000003839 salts Chemical class 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 239000002253 acid Substances 0.000 claims description 45
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
• 229910052717 sulfur Inorganic materials 0.000 claims description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
• 125000004429 atom Chemical group 0.000 claims description 40
• 125000001153 fluoro group Chemical group F* 0.000 claims description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• 229910052799 carbon Inorganic materials 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 31
• 229920006395 saturated elastomer Polymers 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 27
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 206010012601 diabetes mellitus Diseases 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 15
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 14
• 208000008589 Obesity Diseases 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 208000030159 metabolic disease Diseases 0.000 claims description 11
• 235000020824 obesity Nutrition 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
• 206010022489 Insulin Resistance Diseases 0.000 claims description 9
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000003566 oxetanyl group Chemical group 0.000 claims description 9
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
• 229940124597 therapeutic agent Drugs 0.000 claims description 9
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
• 239000000969 carrier Substances 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
• 150000007513 acids Chemical class 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 150000001298 alcohols Chemical class 0.000 claims description 4
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• 125000003342 alkenyl group Chemical group 0.000 claims 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
• 125000002346 iodo group Chemical group I* 0.000 claims 2
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 108010077519 Peptide Elongation Factor 2 Proteins 0.000 claims 1
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
• 229920000180 alkyd Polymers 0.000 claims 1
• 125000004414 alkyl thio group Chemical group 0.000 claims 1
• 125000001246 bromo group Chemical group Br* 0.000 claims 1
• 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
• 125000006001 difluoroethyl group Chemical group 0.000 claims 1
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 239000008141 laxative Substances 0.000 claims 1
• 230000002475 laxative effect Effects 0.000 claims 1
• 229910052759 nickel Inorganic materials 0.000 claims 1
• 150000002989 phenols Chemical class 0.000 claims 1
• 229910052712 strontium Inorganic materials 0.000 claims 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
• 239000010936 titanium Substances 0.000 claims 1
• 229910052719 titanium Inorganic materials 0.000 claims 1
• 238000000034 method Methods 0.000 description 513
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 288
• 238000001819 mass spectrum Methods 0.000 description 273
• 239000000543 intermediate Substances 0.000 description 263
• 239000000203 mixture Substances 0.000 description 216
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 157
• 229960000583 acetic acid Drugs 0.000 description 150
• 239000000243 solution Substances 0.000 description 144
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 91
• 150000002148 esters Chemical class 0.000 description 85
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
• 239000000460 chlorine Substances 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
• 239000000741 silica gel Substances 0.000 description 54
• 229910002027 silica gel Inorganic materials 0.000 description 54
• 229960001866 silicon dioxide Drugs 0.000 description 54
• 239000002904 solvent Substances 0.000 description 52
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 49
• RHMDISFJOKCCAQ-SSDOTTSWSA-N methyl 2-[(3s)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 RHMDISFJOKCCAQ-SSDOTTSWSA-N 0.000 description 45
• 239000011734 sodium Substances 0.000 description 38
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
• 239000000284 extract Substances 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 238000001816 cooling Methods 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 30
• 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 description 29
• 102100026148 Free fatty acid receptor 1 Human genes 0.000 description 28
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 28
• NLPMNZKJBDLTSF-OPAMFIHVSA-N methyl 2-[(3s)-6-[[(1r)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2B1OC(C)(C)C(C)(C)O1 NLPMNZKJBDLTSF-OPAMFIHVSA-N 0.000 description 28
• 101150093826 par1 gene Proteins 0.000 description 28
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 27
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
• 239000012267 brine Substances 0.000 description 26
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
• 229910052740 iodine Inorganic materials 0.000 description 25
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 229960004132 diethyl ether Drugs 0.000 description 21
• 239000003054 catalyst Substances 0.000 description 20
• 150000004702 methyl esters Chemical class 0.000 description 19
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 17
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 17
• 125000001424 substituent group Chemical group 0.000 description 16
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• 229940002612 prodrug Drugs 0.000 description 14
• 239000000651 prodrug Substances 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
• 239000012071 phase Substances 0.000 description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
• 102000004877 Insulin Human genes 0.000 description 12
• 108090001061 Insulin Proteins 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 239000001257 hydrogen Substances 0.000 description 12
• 229940125396 insulin Drugs 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• 238000011321 prophylaxis Methods 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• CPNJYUJMJOGAMA-AWEZNQCLSA-N [(1s)-4-bromo-2,3-dihydro-1h-inden-1-yl]oxy-tert-butyl-dimethylsilane Chemical compound C1=CC=C(Br)C2=C1[C@@H](O[Si](C)(C)C(C)(C)C)CC2 CPNJYUJMJOGAMA-AWEZNQCLSA-N 0.000 description 11
• 239000012298 atmosphere Substances 0.000 description 11
• 208000035475 disorder Diseases 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 235000019198 oils Nutrition 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 9
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 9
• 229910002091 carbon monoxide Inorganic materials 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• 229910052763 palladium Inorganic materials 0.000 description 9
• 239000001117 sulphuric acid Substances 0.000 description 9
• 235000011149 sulphuric acid Nutrition 0.000 description 9
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
• 210000004369 blood Anatomy 0.000 description 8
• 239000008280 blood Substances 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 8
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
• 230000004060 metabolic process Effects 0.000 description 8
• 239000002243 precursor Substances 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 229940086542 triethylamine Drugs 0.000 description 8
• 239000002841 Lewis acid Substances 0.000 description 7
• 239000013543 active substance Substances 0.000 description 7
• 229910052786 argon Inorganic materials 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 239000008103 glucose Substances 0.000 description 7
• 239000000859 incretin Substances 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 230000003914 insulin secretion Effects 0.000 description 7
• 150000007517 lewis acids Chemical class 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• RNXQQZNOSYBFTN-VIFPVBQESA-N (1s)-4-bromo-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC=C(Br)C2=C1[C@@H](O)CC2 RNXQQZNOSYBFTN-VIFPVBQESA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
• 208000032928 Dyslipidaemia Diseases 0.000 description 6
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 6
• 208000031226 Hyperlipidaemia Diseases 0.000 description 6
• 208000017170 Lipid metabolism disease Diseases 0.000 description 6
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• FKZUEBXQSDTDOB-UHFFFAOYSA-N methyl 2-(6-hydroxy-7-methyl-2,3-dihydro-1-benzofuran-3-yl)acetate Chemical compound C1=CC(O)=C(C)C2=C1C(CC(=O)OC)CO2 FKZUEBXQSDTDOB-UHFFFAOYSA-N 0.000 description 3
• JQQSDACTVXYEJC-KZULUSFZSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,1,2,2,2-pentafluoroethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 JQQSDACTVXYEJC-KZULUSFZSA-N 0.000 description 3
• OLESYFNSROHCQP-JLTOFOAXSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,1-difluoro-2-hydroxy-2-methylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)C(C)(C)O)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 OLESYFNSROHCQP-JLTOFOAXSA-N 0.000 description 3
• GAUNTMJFZFUTPA-QVKFZJNVSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,1-difluoro-2-methoxy-2-methylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)C(C)(C)OC)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 GAUNTMJFZFUTPA-QVKFZJNVSA-N 0.000 description 3
• CBTOFHCNAPMAMO-HOYKHHGWSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,2,4-trimethyl-6-oxopyridin-3-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C=1C(C)=CC(=O)N(C)C=1C CBTOFHCNAPMAMO-HOYKHHGWSA-N 0.000 description 3
• LGRJEUYGYBRKQI-OPAMFIHVSA-N methyl 2-[(3s)-6-[[(1r)-4-(1-methoxycyclobutyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1(OC)CCC1 LGRJEUYGYBRKQI-OPAMFIHVSA-N 0.000 description 3
• HLQYXSQAJAJBQQ-KBMIEXCESA-N methyl 2-[(3s)-6-[[(1r)-4-(2,6,6-trimethylcyclohexen-1-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)CCCC1(C)C HLQYXSQAJAJBQQ-KBMIEXCESA-N 0.000 description 3
• DFUALULKUSBVJS-OPAMFIHVSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-oxopyridin-1-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2N1C=CC=CC1=O DFUALULKUSBVJS-OPAMFIHVSA-N 0.000 description 3
• QMVVRFUVTLJHEN-XHCCPWGMSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-propan-2-ylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=CC=C1C(C)C QMVVRFUVTLJHEN-XHCCPWGMSA-N 0.000 description 3
• OUXVMDHKYIMRSI-UZUQRXQVSA-N methyl 2-[(3s)-6-[[(1r)-4-(3-cyanopyridin-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=NC=CC=C1C#N OUXVMDHKYIMRSI-UZUQRXQVSA-N 0.000 description 3
• GXMLGWRSDZSSKT-NIYFSFCBSA-N methyl 2-[(3s)-6-[[(1r)-4-(3-methoxy-2,6-dimethylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=CC(OC)=C1C GXMLGWRSDZSSKT-NIYFSFCBSA-N 0.000 description 3
• ZBRFREKXIHHLCN-IQGLISFBSA-N methyl 2-[(3s)-6-[[(1r)-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=C(O)C=C1C ZBRFREKXIHHLCN-IQGLISFBSA-N 0.000 description 3
• PIPZCAZQIOLHOA-WXTAPIANSA-N methyl 2-[(3s)-6-[[(1r)-4-(5-methoxy-2-methylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC(OC)=CC=C1C PIPZCAZQIOLHOA-WXTAPIANSA-N 0.000 description 3
• RMPHCYJSGCEKIB-IQGLISFBSA-N methyl 2-[(3s)-6-[[(1r)-4-(6,6-dimethylcyclohexen-1-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CCCCC1(C)C RMPHCYJSGCEKIB-IQGLISFBSA-N 0.000 description 3
• NIWQFBHHIWEJCJ-HOYKHHGWSA-N methyl 2-[(3s)-6-[[(1r)-4-(6-methoxy-2,4-dimethylpyridin-3-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=C(OC)N=C1C NIWQFBHHIWEJCJ-HOYKHHGWSA-N 0.000 description 3
• KQYSZQBQWKTVGE-KZULUSFZSA-N methyl 2-[(3s)-6-[[(1r)-4-(difluoromethoxy)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)OC(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 KQYSZQBQWKTVGE-KZULUSFZSA-N 0.000 description 3
• BLJKCTOODPCYLD-UZUQRXQVSA-N methyl 2-[(3s)-6-[[(1r)-4-(oxane-4-carbonyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C(=O)C1CCOCC1 BLJKCTOODPCYLD-UZUQRXQVSA-N 0.000 description 3
• BZSWRWKJMVYCGM-VOIUYBSRSA-N methyl 2-[(3s)-6-[[(1r)-4-[2-(1,1,2,2,2-pentafluoroethyl)phenyl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=CC=C1C(F)(F)C(F)(F)F BZSWRWKJMVYCGM-VOIUYBSRSA-N 0.000 description 3
• HLPFDVGMDKJEMF-IVZQSRNASA-N methyl 2-[(3s)-6-[[(1r)-4-[2-methoxy-4-(trifluoromethyl)pyridin-3-yl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(OC)N=CC=C1C(F)(F)F HLPFDVGMDKJEMF-IVZQSRNASA-N 0.000 description 3
• KIMMAMPJVBYLSC-YKGWIAGDSA-N methyl 2-[(3s)-6-[[(1r)-4-[5-[tert-butyl(dimethyl)silyl]oxy-2-methylphenyl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C KIMMAMPJVBYLSC-YKGWIAGDSA-N 0.000 description 3
• BSWUDMRJVNACCX-PIGZYNQJSA-N methyl 2-[(3s)-6-[[(1r)-4-chloro-5-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=C(C=C2)C(F)(F)F)Cl)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 BSWUDMRJVNACCX-PIGZYNQJSA-N 0.000 description 3
• UELOMSRNIWRWJJ-PIGZYNQJSA-N methyl 2-[(3s)-6-[[(1r)-4-chloro-5-fluoro-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=C(F)C=C2)Cl)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 UELOMSRNIWRWJJ-PIGZYNQJSA-N 0.000 description 3
• QDALYNIRMWDRHQ-OPAMFIHVSA-N methyl 2-[(3s)-6-[[(1r)-4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2N1CCOCC1 QDALYNIRMWDRHQ-OPAMFIHVSA-N 0.000 description 3
• KXJHMJCLYUQBLY-QVKFZJNVSA-N methyl 2-[(3s)-6-[[(1r)-4-propan-2-yl-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(C)C)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 KXJHMJCLYUQBLY-QVKFZJNVSA-N 0.000 description 3
• ODDGNMLFZDXUSF-PXDATVDWSA-N methyl 2-[(3s)-6-[[(1r)-5-(2,6-dimethylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H](C1=CC=2)OC=3C=C4OC[C@H](C4=CC=3)CC(=O)OC)CC1=CC=2C1=C(C)C=CC=C1C ODDGNMLFZDXUSF-PXDATVDWSA-N 0.000 description 3
• FRGOYGLTTOEPIP-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-5-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 FRGOYGLTTOEPIP-FZKQIMNGSA-N 0.000 description 3
• XRHAYRNNBWZLRL-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-5-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=C(C)C=C2)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 XRHAYRNNBWZLRL-FZKQIMNGSA-N 0.000 description 3
• XTKSKYUGGZCUBC-IIBYNOLFSA-N methyl 2-[(3s)-6-[[(1r)-5-tert-butyl-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC(C(C)(C)C)=CC=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 XTKSKYUGGZCUBC-IIBYNOLFSA-N 0.000 description 3
• UTMXAHNVISUDNE-BFUOFWGJSA-N methyl 2-[(3s)-6-[[(1r)-6-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC(C)=C2)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 UTMXAHNVISUDNE-BFUOFWGJSA-N 0.000 description 3
• SUYFGCQOXWMPBO-CXAGYDPISA-N methyl 2-[(3s)-6-[[(1r)-7-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=CC(C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 SUYFGCQOXWMPBO-CXAGYDPISA-N 0.000 description 3
• SSKAGAMLPGIWSJ-PIGZYNQJSA-N methyl 2-[(3s)-6-[[(1r)-7-fluoro-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2F)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 SSKAGAMLPGIWSJ-PIGZYNQJSA-N 0.000 description 3
• FSZJMHGMTWAEIT-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-7-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2C)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 FSZJMHGMTWAEIT-FZKQIMNGSA-N 0.000 description 3
• JCTSMAOMLOEEET-ACJLOTCBSA-N methyl 2-[(3s)-6-[[(1s)-6-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=C(C(F)(F)F)C=C2[C@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 JCTSMAOMLOEEET-ACJLOTCBSA-N 0.000 description 3
• BQGLBAUIXKRBHU-ACJLOTCBSA-N methyl 2-[(3s)-6-[[(1s)-6-bromo-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=C(Br)C=C2[C@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 BQGLBAUIXKRBHU-ACJLOTCBSA-N 0.000 description 3
• AOJLYUOZZQESPX-ZFAMYZPZSA-N methyl 2-[(3s)-6-[[4-[cyclobutyl(methoxy)methyl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C=1C=CC=2C(OC=3C=C4OC[C@@H](CC(=O)OC)C4=CC=3)CCC=2C=1C(OC)C1CCC1 AOJLYUOZZQESPX-ZFAMYZPZSA-N 0.000 description 3
• YIUOCQPOZMVXRX-PQJIZZRHSA-N methyl 2-[4-methyl-6-[[(1r)-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)F)=C2[C@@H]1OC1=CC(C)=C2C(CC(=O)OC)COC2=C1 YIUOCQPOZMVXRX-PQJIZZRHSA-N 0.000 description 3
• MPESIMKFKUCLGB-PQJIZZRHSA-N methyl 2-[5-methyl-6-[[(1r)-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)F)=C2[C@@H]1OC1=C(C)C=C2C(CC(=O)OC)COC2=C1 MPESIMKFKUCLGB-PQJIZZRHSA-N 0.000 description 3
• IGWOROOSCNTYBJ-UHFFFAOYSA-N methyl 2-[6-[[4-(1-methoxy-2,2-dimethylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1=C2C(CC(=O)OC)COC2=CC(OC2C=3C=CC=C(C=3CC2)C(OC)C(C)(C)C)=C1 IGWOROOSCNTYBJ-UHFFFAOYSA-N 0.000 description 3
• RKIMTQUJDNCIHQ-UHFFFAOYSA-N methyl 2-[6-[[4-(2,2-difluoro-1-methoxyethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1=C2C(CC(=O)OC)COC2=CC(OC2C=3C=CC=C(C=3CC2)C(C(F)F)OC)=C1 RKIMTQUJDNCIHQ-UHFFFAOYSA-N 0.000 description 3
• SQBMIZXNWXOQHS-UHFFFAOYSA-N methyl 2-[6-[[4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)F)=C2C1OC1=CC=C2C(CC(=O)OC)COC2=C1 SQBMIZXNWXOQHS-UHFFFAOYSA-N 0.000 description 3
• FNIUKCXRZUXOOL-GAGCMDECSA-N methyl 2-[7-methyl-6-[[(1r)-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)F)=C2[C@@H]1OC(C=C1)=C(C)C2=C1C(CC(=O)OC)CO2 FNIUKCXRZUXOOL-GAGCMDECSA-N 0.000 description 3
• UZKXUKZPWZVIMC-UHFFFAOYSA-N methyl 3-[2-(1,1,2,2,2-pentafluoroethyl)phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1C(F)(F)C(F)(F)F UZKXUKZPWZVIMC-UHFFFAOYSA-N 0.000 description 3
• SLJXSIOJASYFEZ-UHFFFAOYSA-N methyl 4-(3-chloropropyl)oxane-4-carboxylate Chemical compound ClCCCC1(C(=O)OC)CCOCC1 SLJXSIOJASYFEZ-UHFFFAOYSA-N 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 229960005095 pioglitazone Drugs 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 230000003449 preventive effect Effects 0.000 description 3
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
• 238000011894 semi-preparative HPLC Methods 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 235000000346 sugar Nutrition 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• 208000011580 syndromic disease Diseases 0.000 description 3
• ZYAIMSGJJALINN-KRWDZBQOSA-N tert-butyl-[[(1s)-4-(1,1-difluoro-2-methoxy-2-methylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound COC(C)(C)C(F)(F)C1=CC=CC2=C1CC[C@@H]2O[Si](C)(C)C(C)(C)C ZYAIMSGJJALINN-KRWDZBQOSA-N 0.000 description 3
• LHACGHWZOLRXBL-SFHVURJKSA-N tert-butyl-[[(1s)-4-(2,2-dimethylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound CC(C)(C)CC1=CC=CC2=C1CC[C@@H]2O[Si](C)(C)C(C)(C)C LHACGHWZOLRXBL-SFHVURJKSA-N 0.000 description 3
• KHCJHFNAEVOTDV-YDNXMHBPSA-N tert-butyl-[[(1s)-4-(2-methoxy-3,3-dimethylbutan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound COC(C)(C(C)(C)C)C1=CC=CC2=C1CC[C@@H]2O[Si](C)(C)C(C)(C)C KHCJHFNAEVOTDV-YDNXMHBPSA-N 0.000 description 3
• OUNGWUOGJDGXPA-VIQWUECVSA-N tert-butyl-[[(1s)-4-[4-(iodomethyl)-3,3-dimethyloxetan-2-yl]-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound C([C@@H]1O[Si](C)(C)C(C)(C)C)CC2=C1C=CC=C2C1OC(CI)C1(C)C OUNGWUOGJDGXPA-VIQWUECVSA-N 0.000 description 3
• LPNDUTJYNYNHJE-KRWDZBQOSA-N tert-butyl-[[(1s)-4-cyclopropyl-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound C([C@@H]1O[Si](C)(C)C(C)(C)C)CC2=C1C=CC=C2C1CC1 LPNDUTJYNYNHJE-KRWDZBQOSA-N 0.000 description 3
• PHWSJQYUMVJZFE-UHFFFAOYSA-N tert-butyl-[[4-(2,2-difluoro-1-methoxyethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound COC(C(F)F)C1=CC=CC2=C1CCC2O[Si](C)(C)C(C)(C)C PHWSJQYUMVJZFE-UHFFFAOYSA-N 0.000 description 3
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• BNCANDKTPQEZLG-WHDUELSGSA-N tert-butyl-dimethyl-[[(1s)-4-(3,3,4-trimethyloxetan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]silane Chemical compound CC1(C)C(C)OC1C1=CC=CC2=C1CC[C@@H]2O[Si](C)(C)C(C)(C)C BNCANDKTPQEZLG-WHDUELSGSA-N 0.000 description 3
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• 230000037356 lipid metabolism Effects 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229910052808 lithium carbonate Inorganic materials 0.000 description 2
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• 230000007774 longterm Effects 0.000 description 2
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
• 238000007726 management method Methods 0.000 description 2
• 238000005259 measurement Methods 0.000 description 2
• 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 239000002207 metabolite Substances 0.000 description 2
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• CMOCFAOZPNRZCW-JLTOFOAXSA-N methyl 2-[(3S)-6-[[(1R)-1-(trifluoromethoxy)-2,3-dihydroinden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound COC(C[C@@H]1COC2=C1C=CC(=C2)O[C@]1(CCC2=CC=CC=C12)OC(F)(F)F)=O CMOCFAOZPNRZCW-JLTOFOAXSA-N 0.000 description 2
• LIEALQFVIUZVHI-HOYKHHGWSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,3,5-trimethyl-2-oxopyridin-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C=1C(C)=CN(C)C(=O)C=1C LIEALQFVIUZVHI-HOYKHHGWSA-N 0.000 description 2
• UMMKTJPICZQLFE-HICCQETBSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-methoxy-3,3-dimethylbutan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(C)(OC)C(C)(C)C)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 UMMKTJPICZQLFE-HICCQETBSA-N 0.000 description 2
• VEMATQFEUNCVNO-PUKPOGLGSA-N methyl 2-[(3s)-6-[[(1r)-4-(3,3,4-trimethyloxetan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1OC(C)C1(C)C VEMATQFEUNCVNO-PUKPOGLGSA-N 0.000 description 2
• KGYJGGOLGYENPY-MZNJEOGPSA-N methyl 2-[(3s)-6-[[(1r)-4-(5,5-dimethylcyclopenten-1-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CCCC1(C)C KGYJGGOLGYENPY-MZNJEOGPSA-N 0.000 description 2
• BWUUFQLEYPVXEM-CRICUBBOSA-N methyl 2-[(3s)-6-[[(1r)-4-(5-hydroxy-2-methylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC(O)=CC=C1C BWUUFQLEYPVXEM-CRICUBBOSA-N 0.000 description 2
• KSKXABFPAYHKAU-WVXBCFDCSA-N methyl 2-[(3s)-6-[[(1r)-4-[4-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylphenyl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C KSKXABFPAYHKAU-WVXBCFDCSA-N 0.000 description 2
• IUWYILPOVJHXNP-AUUYWEPGSA-N methyl 2-[(3s)-6-[[(1r)-4-cyano-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C#N)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 IUWYILPOVJHXNP-AUUYWEPGSA-N 0.000 description 2
• QDYISHXDIGJWKR-JIPXPUAJSA-N methyl 2-[(3s)-6-[[(1r)-5-(2-propan-2-ylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H](C1=CC=2)OC=3C=C4OC[C@H](C4=CC=3)CC(=O)OC)CC1=CC=2C1=CC=CC=C1C(C)C QDYISHXDIGJWKR-JIPXPUAJSA-N 0.000 description 2
• SCWZCKKJGIAYHY-RBFZIWAESA-N methyl 2-[(3s)-6-[[4-(1-methylcyclopropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H](C1=CC=2)CC(=O)OC)OC1=CC=2OC1CCC2=C1C=CC=C2C1(C)CC1 SCWZCKKJGIAYHY-RBFZIWAESA-N 0.000 description 2
• XAXHGGSZHNRMEB-RBFZIWAESA-N methyl 2-[(3s)-6-[[4-(2-cyanopropan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(C)(C)C#N)=C2C1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 XAXHGGSZHNRMEB-RBFZIWAESA-N 0.000 description 2
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• ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
• 229960004873 levomenthol Drugs 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 229960002701 liraglutide Drugs 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000012139 lysis buffer Substances 0.000 description 1
• CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 206010025482 malaise Diseases 0.000 description 1
• 150000002688 maleic acid derivatives Chemical class 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 150000004701 malic acid derivatives Chemical class 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000006371 metabolic abnormality Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 150000002739 metals Chemical class 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 description 1
• RHMDISFJOKCCAQ-ZETCQYMHSA-N methyl 2-[(3r)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound OC1=CC=C2[C@@H](CC(=O)OC)COC2=C1 RHMDISFJOKCCAQ-ZETCQYMHSA-N 0.000 description 1
• NVJUVFQEQBWHQD-IKJXHCRLSA-N methyl 2-[(3s)-6-(2,3-dihydro-1h-inden-1-yloxy)-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=CC=C2C1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 NVJUVFQEQBWHQD-IKJXHCRLSA-N 0.000 description 1
• MGJTUBPXFHLDOQ-PIGZYNQJSA-N methyl 2-[(3s)-6-[[(1r)-4,5-difluoro-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=C(F)C=C2)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 MGJTUBPXFHLDOQ-PIGZYNQJSA-N 0.000 description 1
• JIIJVDKXFXPICI-JLTOFOAXSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,1-difluoro-2-methoxyethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1=C2[C@H](CC(=O)OC)COC2=CC(O[C@H]2C=3C=CC=C(C=3CC2)C(F)(F)COC)=C1 JIIJVDKXFXPICI-JLTOFOAXSA-N 0.000 description 1
• ZDSLCFQKFLJYIJ-UZUQRXQVSA-N methyl 2-[(3s)-6-[[(1r)-4-(1,3,5-trimethylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C=1C(C)=NN(C)C=1C ZDSLCFQKFLJYIJ-UZUQRXQVSA-N 0.000 description 1
• IGWOROOSCNTYBJ-IIGFZZKMSA-N methyl 2-[(3s)-6-[[(1r)-4-(1-methoxy-2,2-dimethylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1=C2[C@H](CC(=O)OC)COC2=CC(O[C@H]2C=3C=CC=C(C=3CC2)C(OC)C(C)(C)C)=C1 IGWOROOSCNTYBJ-IIGFZZKMSA-N 0.000 description 1
• SCWZCKKJGIAYHY-QVKFZJNVSA-N methyl 2-[(3s)-6-[[(1r)-4-(1-methylcyclopropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1(C)CC1 SCWZCKKJGIAYHY-QVKFZJNVSA-N 0.000 description 1
• MQCIAKLEUADCIX-VGOFRKELSA-N methyl 2-[(3s)-6-[[(1r)-4-(2,2-dimethylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)CC(C)(C)C)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 MQCIAKLEUADCIX-VGOFRKELSA-N 0.000 description 1
• XYZKSBQONUKUEJ-HOYKHHGWSA-N methyl 2-[(3s)-6-[[(1r)-4-(2,4-dimethylpyridin-3-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=CN=C1C XYZKSBQONUKUEJ-HOYKHHGWSA-N 0.000 description 1
• RWPKMDAWSFMYIB-IQMFZBJNSA-N methyl 2-[(3s)-6-[[(1r)-4-(2,6-dichlorophenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(Cl)C=CC=C1Cl RWPKMDAWSFMYIB-IQMFZBJNSA-N 0.000 description 1
• GFKBKBPOXVRJQI-MZNJEOGPSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-chloro-6-methylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=CC=C1Cl GFKBKBPOXVRJQI-MZNJEOGPSA-N 0.000 description 1
• XAXHGGSZHNRMEB-QVKFZJNVSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-cyanopropan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(C)(C)C#N)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 XAXHGGSZHNRMEB-QVKFZJNVSA-N 0.000 description 1
• QMHMFFFAIRXDQO-HOYKHHGWSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-methoxy-3,5-dimethylpyridin-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=NC(OC)=C1C QMHMFFFAIRXDQO-HOYKHHGWSA-N 0.000 description 1
• SCLIPQRFFZOCQZ-IQGLISFBSA-N methyl 2-[(3s)-6-[[(1r)-4-(2-methylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=CC=C1C SCLIPQRFFZOCQZ-IQGLISFBSA-N 0.000 description 1
• YDMVEHYIKSEVCU-WXTAPIANSA-N methyl 2-[(3s)-6-[[(1r)-4-(3-methoxy-2-methylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=CC(OC)=C1C YDMVEHYIKSEVCU-WXTAPIANSA-N 0.000 description 1
• FGFRDJNYGUZDAC-OPAMFIHVSA-N methyl 2-[(3s)-6-[[(1r)-4-(3-methylpyrazin-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=NC=CN=C1C FGFRDJNYGUZDAC-OPAMFIHVSA-N 0.000 description 1
• TTZRSZVNMJIZGX-UZUQRXQVSA-N methyl 2-[(3s)-6-[[(1r)-4-(3-methylpyridin-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=NC=CC=C1C TTZRSZVNMJIZGX-UZUQRXQVSA-N 0.000 description 1
• ILCWSTGTWRYXDM-UZUQRXQVSA-N methyl 2-[(3s)-6-[[(1r)-4-(4,6-dimethylpyrimidin-5-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)N=CN=C1C ILCWSTGTWRYXDM-UZUQRXQVSA-N 0.000 description 1
• ZQGKMXDUURDPPE-NIYFSFCBSA-N methyl 2-[(3s)-6-[[(1r)-4-(4-methoxy-2,6-dimethylphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=C(C)C=C(OC)C=C1C ZQGKMXDUURDPPE-NIYFSFCBSA-N 0.000 description 1
• ZCCDNGRMYZWIFD-IQMFZBJNSA-N methyl 2-[(3s)-6-[[(1r)-4-(5-fluoro-2-methoxypyridin-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC(OC)=NC=C1F ZCCDNGRMYZWIFD-IQMFZBJNSA-N 0.000 description 1
• MCWQQFNGHBENQZ-LYZGTLIUSA-N methyl 2-[(3s)-6-[[(1r)-4-(8-methylnaphthalen-1-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1=CC(C)=C2C(C3=CC=CC4=C3CC[C@H]4OC=3C=C4OC[C@H](C4=CC=3)CC(=O)OC)=CC=CC2=C1 MCWQQFNGHBENQZ-LYZGTLIUSA-N 0.000 description 1
• QGTFTVXVLITDFE-NIYFSFCBSA-N methyl 2-[(3s)-6-[[(1r)-4-(8-oxaspiro[4.5]dec-3-en-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CCCC11CCOCC1 QGTFTVXVLITDFE-NIYFSFCBSA-N 0.000 description 1
• QHXIDCSVONJMTJ-SJKOYZFVSA-N methyl 2-[(3s)-6-[[(1r)-4-(trifluoromethoxy)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)OC(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 QHXIDCSVONJMTJ-SJKOYZFVSA-N 0.000 description 1
• VYMVBXQGDOEQSL-BPKZHXITSA-N methyl 2-[(3s)-6-[[(1r)-4-[(2r)-3,3-dimethyloxan-2-yl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2[C@@H]1OCCCC1(C)C VYMVBXQGDOEQSL-BPKZHXITSA-N 0.000 description 1
• VYMVBXQGDOEQSL-RXMJPHHWSA-N methyl 2-[(3s)-6-[[(1r)-4-[(2s)-3,3-dimethyloxan-2-yl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2[C@H]1OCCCC1(C)C VYMVBXQGDOEQSL-RXMJPHHWSA-N 0.000 description 1
• XGZNDYFOJICNJU-VOIUYBSRSA-N methyl 2-[(3s)-6-[[(1r)-4-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=CC=C1C(F)(F)F XGZNDYFOJICNJU-VOIUYBSRSA-N 0.000 description 1
• KYKAGFBLFKUWTH-IVZQSRNASA-N methyl 2-[(3s)-6-[[(1r)-4-[6-methoxy-3-(trifluoromethyl)pyridin-2-yl]-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=NC(OC)=CC=C1C(F)(F)F KYKAGFBLFKUWTH-IVZQSRNASA-N 0.000 description 1
• PEIUIFQXXUSQET-KZULUSFZSA-N methyl 2-[(3s)-6-[[(1r)-4-chloro-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)Cl)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 PEIUIFQXXUSQET-KZULUSFZSA-N 0.000 description 1
• QSLGRKPWBHNNPI-QVKFZJNVSA-N methyl 2-[(3s)-6-[[(1r)-4-cyclopropyl-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OC[C@H](C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1CC1 QSLGRKPWBHNNPI-QVKFZJNVSA-N 0.000 description 1
• JDKAPHQYSGAGFS-NIYFSFCBSA-N methyl 2-[(3s)-6-[[(1r)-4-isoquinolin-1-yl-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1=CC=C2C(C3=CC=CC4=C3CC[C@H]4OC=3C=C4OC[C@H](C4=CC=3)CC(=O)OC)=NC=CC2=C1 JDKAPHQYSGAGFS-NIYFSFCBSA-N 0.000 description 1
• FHQOPBXDKDDFEH-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-5-chloro-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC(Cl)=CC=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 FHQOPBXDKDDFEH-FZKQIMNGSA-N 0.000 description 1
• JCTSMAOMLOEEET-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-6-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=C(C(F)(F)F)C=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 JCTSMAOMLOEEET-FZKQIMNGSA-N 0.000 description 1
• ZWTJDKXZTWDXOM-ADLMAVQZSA-N methyl 2-[(3s)-6-[[(1r)-6-fluoro-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC(F)=C2)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 ZWTJDKXZTWDXOM-ADLMAVQZSA-N 0.000 description 1
• KJMSSTXFCHSSMJ-IRCUZVAFSA-N methyl 2-[6-[[(1R)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound COC(CC1COC2=C1C=CC(=C2)O[C@@H]1C=CC2=C(C=CC=C12)C=1CCOCC=1)=O KJMSSTXFCHSSMJ-IRCUZVAFSA-N 0.000 description 1
• RILRSULYTPUZSR-IRCUZVAFSA-N methyl 2-[6-[[(1r)-4-(1-methyl-2-oxopyridin-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C=1C=CN(C)C(=O)C=1 RILRSULYTPUZSR-IRCUZVAFSA-N 0.000 description 1
• GMQKWFJVQAVOIB-ZZAPORBBSA-N methyl 2-[6-[[(1r)-4-(1-methylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C=1C=NN(C)C=1 GMQKWFJVQAVOIB-ZZAPORBBSA-N 0.000 description 1
• SFFDYBAYWDEMKL-IRCUZVAFSA-N methyl 2-[6-[[(1r)-4-(3,6-dihydro-2h-pyran-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CCOCC1 SFFDYBAYWDEMKL-IRCUZVAFSA-N 0.000 description 1
• DBDVGDAIGQYMKV-IXXGTQFESA-N methyl 2-[6-[[(1r)-4-(4-methoxyphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=C(OC)C=C1 DBDVGDAIGQYMKV-IXXGTQFESA-N 0.000 description 1
• RTJQYEKETKZWAO-IRCUZVAFSA-N methyl 2-[6-[[(1r)-4-(oxan-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1CCOCC1 RTJQYEKETKZWAO-IRCUZVAFSA-N 0.000 description 1
• CNCMVGXVKBJYNU-UHFFFAOYSA-N methyl oxane-4-carboxylate Chemical compound COC(=O)C1CCOCC1 CNCMVGXVKBJYNU-UHFFFAOYSA-N 0.000 description 1
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 229960002900 methylcellulose Drugs 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 229960001110 miglitol Drugs 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000003607 modifier Substances 0.000 description 1
• 150000002772 monosaccharides Chemical class 0.000 description 1
• 229910052901 montmorillonite Inorganic materials 0.000 description 1
• AOZRWXWPYIAFMC-UHFFFAOYSA-N n-(methoxymethyl)oxane-4-carboxamide Chemical compound COCNC(=O)C1CCOCC1 AOZRWXWPYIAFMC-UHFFFAOYSA-N 0.000 description 1
• OQJBFFCUFALWQL-UHFFFAOYSA-N n-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• HKNFUJIVKFTWJB-UHFFFAOYSA-N n-methoxy-n-methylcyclobutanecarboxamide Chemical compound CON(C)C(=O)C1CCC1 HKNFUJIVKFTWJB-UHFFFAOYSA-N 0.000 description 1
• UFBLFACMCVLAON-UHFFFAOYSA-N n-methoxy-n-methylpent-4-enamide Chemical compound CON(C)C(=O)CCC=C UFBLFACMCVLAON-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 201000001119 neuropathy Diseases 0.000 description 1
• 230000007823 neuropathy Effects 0.000 description 1
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