BR112021005914A2 - derivados de tieno[3,2-b]piridina como inibidores de udp glicosiltransferase e métodos de uso - Google Patents

Info

Publication number

BR112021005914A2

BR112021005914A2 BR112021005914-8A BR112021005914A BR112021005914A2 BR 112021005914 A2 BR112021005914 A2 BR 112021005914A2 BR 112021005914 A BR112021005914 A BR 112021005914A BR 112021005914 A2 BR112021005914 A2 BR 112021005914A2

Authority

BR

Brazil

Prior art keywords

thieno

trifluoromethyl

alkyl

pyridin

methylcarbamoyl

Prior art date

2018-10-01

Links

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• 238000000034 method Methods 0.000 title claims abstract description 51
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 5
• 239000003297 glycosyltransferase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 417
• 239000000203 mixture Substances 0.000 claims abstract description 114
• 201000011442 Metachromatic leukodystrophy Diseases 0.000 claims abstract description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• 208000010055 Globoid Cell Leukodystrophy Diseases 0.000 claims abstract description 14
• 208000028226 Krabbe disease Diseases 0.000 claims abstract description 14
• 201000010099 disease Diseases 0.000 claims abstract description 12
• -1 -OH Chemical group 0.000 claims description 249
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 91
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 91
• 125000001072 heteroaryl group Chemical group 0.000 claims description 79
• 229910052739 hydrogen Inorganic materials 0.000 claims description 76
• 239000001257 hydrogen Substances 0.000 claims description 69
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
• 125000005843 halogen group Chemical group 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 43
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 150000002431 hydrogen Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 239000000651 prodrug Substances 0.000 claims description 15
• 229940002612 prodrug Drugs 0.000 claims description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
• 229910003827 NRaRb Inorganic materials 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 229910052701 rubidium Inorganic materials 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052705 radium Inorganic materials 0.000 claims description 7
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 125000004419 alkynylene group Chemical group 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 125000004450 alkenylene group Chemical group 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 208000035475 disorder Diseases 0.000 claims 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 398
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 252
• 239000000243 solution Substances 0.000 description 200
• 239000007787 solid Substances 0.000 description 199
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
• 238000006243 chemical reaction Methods 0.000 description 176
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 152
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 150
• 238000005160 1H NMR spectroscopy Methods 0.000 description 147
• 235000019439 ethyl acetate Nutrition 0.000 description 132
• 239000000543 intermediate Substances 0.000 description 118
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 110
• 239000000047 product Substances 0.000 description 108
• 238000001819 mass spectrum Methods 0.000 description 103
• 229940125904 compound 1 Drugs 0.000 description 94
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 85
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 80
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 78
• 239000012044 organic layer Substances 0.000 description 75
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
• 239000000377 silicon dioxide Substances 0.000 description 69
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
• 238000003818 flash chromatography Methods 0.000 description 59
• 239000007832 Na2SO4 Substances 0.000 description 58
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 58
• 229910052938 sodium sulfate Inorganic materials 0.000 description 58
• 235000011152 sodium sulphate Nutrition 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• 239000000463 material Substances 0.000 description 50
• 229910001868 water Inorganic materials 0.000 description 50
• 239000000725 suspension Substances 0.000 description 49
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
• 238000003756 stirring Methods 0.000 description 45
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 42
• 239000000284 extract Substances 0.000 description 42
• 235000017557 sodium bicarbonate Nutrition 0.000 description 39
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 39
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 37
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 32
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 29
• 239000012043 crude product Substances 0.000 description 29
• 239000003480 eluent Substances 0.000 description 29
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 28
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 28
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 28
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 27
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 26
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
• 238000000746 purification Methods 0.000 description 25
• 239000003921 oil Substances 0.000 description 24
• 239000012267 brine Substances 0.000 description 23
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
• 229910052805 deuterium Inorganic materials 0.000 description 22
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 20
• 229910052737 gold Inorganic materials 0.000 description 20
• 239000010931 gold Substances 0.000 description 20
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
• 229910000029 sodium carbonate Inorganic materials 0.000 description 19
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
• 239000013058 crude material Substances 0.000 description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 18
• DDOVBCWVTOHGCU-QMXMISKISA-N n-[(e,2s,3r)-3-hydroxy-1-[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonadec-4-en-2-yl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O DDOVBCWVTOHGCU-QMXMISKISA-N 0.000 description 18
• 102100034689 2-hydroxyacylsphingosine 1-beta-galactosyltransferase Human genes 0.000 description 17
• WCRHJCMVVHZBRK-UHFFFAOYSA-N thieno[3,2-b]pyridine-3-carboxamide Chemical compound S1C=C(C2=NC=CC=C21)C(=O)N WCRHJCMVVHZBRK-UHFFFAOYSA-N 0.000 description 17
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 16
• 239000012065 filter cake Substances 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 238000004458 analytical method Methods 0.000 description 15
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
• 125000004429 atom Chemical group 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• 239000011734 sodium Substances 0.000 description 14
• 239000012258 stirred mixture Substances 0.000 description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
• 101000946034 Homo sapiens 2-hydroxyacylsphingosine 1-beta-galactosyltransferase Proteins 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
• 235000019341 magnesium sulphate Nutrition 0.000 description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
• ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 239000003814 drug Substances 0.000 description 12
• 238000000967 suction filtration Methods 0.000 description 12
• 102000004190 Enzymes Human genes 0.000 description 11
• 108090000790 Enzymes Proteins 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 230000008901 benefit Effects 0.000 description 11
• 238000010348 incorporation Methods 0.000 description 11
• 229910021529 ammonia Inorganic materials 0.000 description 10
• 125000002393 azetidinyl group Chemical group 0.000 description 10
• LHHGDZSESBACKH-UHFFFAOYSA-N chlordecone Chemical compound ClC12C3(Cl)C(Cl)(Cl)C4(Cl)C2(Cl)C2(Cl)C4(Cl)C3(Cl)C1(Cl)C2=O LHHGDZSESBACKH-UHFFFAOYSA-N 0.000 description 10
• 239000012230 colorless oil Substances 0.000 description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
• 238000002641 enzyme replacement therapy Methods 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 239000002609 medium Substances 0.000 description 9
• 150000004702 methyl esters Chemical class 0.000 description 9
• 125000003373 pyrazinyl group Chemical group 0.000 description 9
• 150000003254 radicals Chemical group 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 239000000758 substrate Substances 0.000 description 9
• 238000002560 therapeutic procedure Methods 0.000 description 9
• 238000009825 accumulation Methods 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 125000001153 fluoro group Chemical group F* 0.000 description 8
• 230000035772 mutation Effects 0.000 description 8
• 125000003367 polycyclic group Chemical group 0.000 description 8
• 235000019270 ammonium chloride Nutrition 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 7
• 239000007789 gas Substances 0.000 description 7
• 230000000155 isotopic effect Effects 0.000 description 7
• 230000003647 oxidation Effects 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 102100022146 Arylsulfatase A Human genes 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 230000004783 oxidative metabolism Effects 0.000 description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 239000011541 reaction mixture Substances 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• 239000000523 sample Substances 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• PLLJHZAFBRMIAW-UHFFFAOYSA-N 2-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=C(C2=NC=CC=C2S1)C(=O)N PLLJHZAFBRMIAW-UHFFFAOYSA-N 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
• YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 5
• 108010036867 Cerebroside-Sulfatase Proteins 0.000 description 5
• 208000016192 Demyelinating disease Diseases 0.000 description 5
• 206010012305 Demyelination Diseases 0.000 description 5
• 208000015439 Lysosomal storage disease Diseases 0.000 description 5
• CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 5
• 210000003169 central nervous system Anatomy 0.000 description 5
• 229940106189 ceramide Drugs 0.000 description 5
• ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 5
• QEWSAQSTTIEZSY-UHFFFAOYSA-N cyclopropylmethylcarbamic acid Chemical compound OC(=O)NCC1CC1 QEWSAQSTTIEZSY-UHFFFAOYSA-N 0.000 description 5
• 230000007812 deficiency Effects 0.000 description 5
• 229930182830 galactose Natural products 0.000 description 5
• VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 5
• 210000001428 peripheral nervous system Anatomy 0.000 description 5
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
• 125000004076 pyridyl group Chemical group 0.000 description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
• 150000003384 small molecules Chemical class 0.000 description 5
• 125000003003 spiro group Chemical group 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• 230000001225 therapeutic effect Effects 0.000 description 5
• 238000012546 transfer Methods 0.000 description 5
• JGIRDDQLZLXRKQ-UHFFFAOYSA-N (4-methoxycarbonylthiophen-3-yl)azanium;chloride Chemical compound Cl.COC(=O)C1=CSC=C1N JGIRDDQLZLXRKQ-UHFFFAOYSA-N 0.000 description 4
• OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 4
• FFOHTSTWXWJGQR-UHFFFAOYSA-N 2-piperazin-1-yl-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CN1CCNCC1 FFOHTSTWXWJGQR-UHFFFAOYSA-N 0.000 description 4
• DRBMDELQCZMFKH-UHFFFAOYSA-N 3-(difluoromethoxy)azetidine Chemical compound FC(F)OC1CNC1 DRBMDELQCZMFKH-UHFFFAOYSA-N 0.000 description 4
• KGMICXXVEAZRJU-UHFFFAOYSA-N 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine;dihydrochloride Chemical compound Cl.Cl.C1NCCN2N=CC=C21 KGMICXXVEAZRJU-UHFFFAOYSA-N 0.000 description 4
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• SZIMDBGJQKCQIP-UHFFFAOYSA-N 5-[4-[(6-ethylpyridin-2-yl)methyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C(C)C1=CC=CC(=N1)CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F SZIMDBGJQKCQIP-UHFFFAOYSA-N 0.000 description 1
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• PKPCGJXDFQFZHR-UHFFFAOYSA-N 5-[4-[(cyclopropylmethylamino)methyl]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide 2,2,2-trifluoroacetic acid Chemical compound CNC(=O)C1=CSC2=C1N=C(C=C2C(F)(F)F)N3CCC(CC3)CNCC4CC4.C(=O)(C(F)(F)F)O PKPCGJXDFQFZHR-UHFFFAOYSA-N 0.000 description 1
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• YTURQJBVHHXOGN-UHFFFAOYSA-N 5-[4-[1-(2-fluoroethyl)azetidin-3-yl]oxypiperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FCCN1CC(C1)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F YTURQJBVHHXOGN-UHFFFAOYSA-N 0.000 description 1
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• DNCMMIMHVJQTBV-UHFFFAOYSA-N 5-[4-[1-(cyclopropylmethoxy)-3-hydroxypropan-2-yl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C1(CC1)COCC(CO)N1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F DNCMMIMHVJQTBV-UHFFFAOYSA-N 0.000 description 1
• MFVHEGHNDZFMDM-UHFFFAOYSA-N 5-[4-[1-[(4-methoxycyclohexyl)amino]-1-oxopropan-2-yl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound COC1CCC(CC1)NC(C(C)N1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)=O MFVHEGHNDZFMDM-UHFFFAOYSA-N 0.000 description 1
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• LCTKIQRIKWSXGI-UHFFFAOYSA-N 5-[4-[2-(1-methoxypropan-2-ylamino)-2-oxoethyl]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound COCC(C)NC(CC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)=O LCTKIQRIKWSXGI-UHFFFAOYSA-N 0.000 description 1
• QQGLMTIARZADSX-UHFFFAOYSA-N 5-[4-[2-(3-fluoropyrrolidin-1-yl)-1-hydroxyethyl]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FC1CN(CC1)CC(O)C1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F QQGLMTIARZADSX-UHFFFAOYSA-N 0.000 description 1
• MWMOLHLFKXPUPR-UHFFFAOYSA-N 5-[4-[2-(3-fluoropyrrolidin-1-yl)ethoxy]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FC1CN(CC1)CCOC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F MWMOLHLFKXPUPR-UHFFFAOYSA-N 0.000 description 1
• FACXWJNSKNRSBO-UHFFFAOYSA-N 5-[4-[2-(3-hydroxypyrrolidin-1-yl)ethoxy]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound OC1CN(CC1)CCOC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F FACXWJNSKNRSBO-UHFFFAOYSA-N 0.000 description 1
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• PXBHZELPMREZDB-UHFFFAOYSA-N 5-[4-[2-(4,4-difluoropiperidin-1-yl)-1-hydroxyethyl]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FC1(CCN(CC1)CC(O)C1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)F PXBHZELPMREZDB-UHFFFAOYSA-N 0.000 description 1
• REBKMBHDEMTXLG-UHFFFAOYSA-N 5-[4-[2-(4,4-difluoropiperidin-1-yl)ethoxy]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FC1(CCN(CC1)CCOC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)F REBKMBHDEMTXLG-UHFFFAOYSA-N 0.000 description 1
• KXHTXEPNMOWNTF-UHFFFAOYSA-N 5-[4-[2-(cyclopropylamino)-2-oxoethoxy]phenyl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C1(CC1)NC(COC1=CC=C(C=C1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)=O KXHTXEPNMOWNTF-UHFFFAOYSA-N 0.000 description 1
• FIGFZOLEGMZOHJ-UHFFFAOYSA-N 5-[4-[2-(cyclopropylamino)-2-oxoethyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C1(CC1)NC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)=O FIGFZOLEGMZOHJ-UHFFFAOYSA-N 0.000 description 1
• PNVAZJNGODKMKS-UHFFFAOYSA-N 5-[4-[2-(cyclopropylamino)-2-oxoethyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide hydron chloride Chemical compound [H+].CNC(=O)C1=CSC2=C1N=C(C=C2C(F)(F)F)N3CCN(CC3)CC(=O)NC4CC4.[Cl-] PNVAZJNGODKMKS-UHFFFAOYSA-N 0.000 description 1
• HPDDJWNWGFYQRG-UHFFFAOYSA-N 5-[4-[2-(cyclopropylmethoxy)ethyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C1(CC1)COCCN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F HPDDJWNWGFYQRG-UHFFFAOYSA-N 0.000 description 1
• PVNURQGHEMSPOU-UHFFFAOYSA-N 5-[4-[2-(cyclopropylmethoxy)ethylsulfonyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C1(CC1)COCCS(=O)(=O)N1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F PVNURQGHEMSPOU-UHFFFAOYSA-N 0.000 description 1
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• WTGPPRUITLHKMU-HZPDHXFCSA-N 5-[4-[2-[(3R,4R)-3-fluoro-4-hydroxypyrrolidin-1-yl]ethoxy]piperidin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound F[C@@H]1CN(C[C@H]1O)CCOC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F WTGPPRUITLHKMU-HZPDHXFCSA-N 0.000 description 1
• LXAJMBZNMYEMAK-UHFFFAOYSA-N 5-[4-[2-[1-(2,2-difluoroethyl)pyrrolidin-3-yl]-2-hydroxyethyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound FC(CN1CC(CC1)C(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F)O)F LXAJMBZNMYEMAK-UHFFFAOYSA-N 0.000 description 1
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• XMAXUDJJJNNQTP-UHFFFAOYSA-N 5-[4-[2-oxo-2-(propan-2-ylamino)ethyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound C(C)(C)NC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)N)C(F)(F)F)=O XMAXUDJJJNNQTP-UHFFFAOYSA-N 0.000 description 1
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• HSDFYRXNKICOJQ-UHFFFAOYSA-N 5-[4-[3-(cyclopropanecarbonylamino)propyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide 2,2,2-trifluoroacetic acid Chemical compound CNC(=O)C1=CSC2=C1N=C(C=C2C(F)(F)F)N3CCN(CC3)CCCNC(=O)C4CC4.C(=O)(C(F)(F)F)O HSDFYRXNKICOJQ-UHFFFAOYSA-N 0.000 description 1
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• ISEMLFYKBUQAKN-UHFFFAOYSA-N 5-[4-[[1-[(4,5-dimethyl-1H-imidazol-2-yl)methyl]-4,5-dimethylimidazol-2-yl]methyl]piperazin-1-yl]-N-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound CC=1N=C(NC=1C)CN1C(=NC(=C1C)C)CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)NC)C(F)(F)F ISEMLFYKBUQAKN-UHFFFAOYSA-N 0.000 description 1
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• FHSPJWXWCKCJCK-CHWSQXEVSA-N [(3R,4R)-3-fluoro-1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-propan-2-ylcarbamate Chemical compound C(C)(C)NC(O[C@H]1[C@@H](CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC)=O)C(F)(F)F)F)=O FHSPJWXWCKCJCK-CHWSQXEVSA-N 0.000 description 1
• QXNFSCVUAUTKFY-RISCZKNCSA-N [(3R,4S)-3-methyl-1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-propan-2-ylcarbamate Chemical compound C(C)(C)NC(O[C@@H]1[C@@H](CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC)=O)C(F)(F)F)C)=O QXNFSCVUAUTKFY-RISCZKNCSA-N 0.000 description 1
• MOLCPLLBQBGJBV-ZDUSSCGKSA-N [(3S)-1-(2,2-difluoroethyl)pyrrolidin-3-yl] N-[1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl]carbamate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CCC(CC1)NC(O[C@@H]1CN(CC1)CC(F)F)=O MOLCPLLBQBGJBV-ZDUSSCGKSA-N 0.000 description 1
• BATDVKMJYNGBTF-STQMWFEESA-N [(3S,4S)-3-fluoro-1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-cyclopropylcarbamate Chemical compound C1(CC1)NC(O[C@@H]1[C@H](CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC)=O)C(F)(F)F)F)=O BATDVKMJYNGBTF-STQMWFEESA-N 0.000 description 1
• FHSPJWXWCKCJCK-STQMWFEESA-N [(3S,4S)-3-fluoro-1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-propan-2-ylcarbamate Chemical compound C(C)(C)NC(O[C@@H]1[C@H](CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC)=O)C(F)(F)F)F)=O FHSPJWXWCKCJCK-STQMWFEESA-N 0.000 description 1
• QXNFSCVUAUTKFY-FZMZJTMJSA-N [(3S,4S)-3-methyl-1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-propan-2-ylcarbamate Chemical compound C(C)(C)NC(O[C@@H]1[C@H](CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC)=O)C(F)(F)F)C)=O QXNFSCVUAUTKFY-FZMZJTMJSA-N 0.000 description 1
• JIKLXTAXUISPJQ-UHFFFAOYSA-N [1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl] 4-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]oxypiperidine-1-carboxylate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)OC1CCN(CC1)C(=O)OC1CN(CC1)CC(F)(F)F JIKLXTAXUISPJQ-UHFFFAOYSA-N 0.000 description 1
• RTVGAUCLKXQVDZ-UHFFFAOYSA-N [1-(2-fluoroethyl)azetidin-3-yl] 6-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]-2,6-diazaspiro[3.3]heptane-2-carboxylate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CC2(CN(C2)C(=O)OC2CN(C2)CCF)C1 RTVGAUCLKXQVDZ-UHFFFAOYSA-N 0.000 description 1
• ZMXHFYHRSKOCRN-UHFFFAOYSA-N [1-(cyanomethyl)azetidin-3-yl] 4-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]oxypiperidine-1-carboxylate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)OC1CCN(CC1)C(=O)OC1CN(C1)CC#N ZMXHFYHRSKOCRN-UHFFFAOYSA-N 0.000 description 1
• NSBXPJTZPPZDFS-UHFFFAOYSA-N [1-(cyanomethyl)azetidin-3-yl] 6-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]-2,6-diazaspiro[3.3]heptane-2-carboxylate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CC2(CN(C2)C(=O)OC2CN(C2)CC#N)C1 NSBXPJTZPPZDFS-UHFFFAOYSA-N 0.000 description 1
• UQXAADJSEXRGRT-UHFFFAOYSA-N [1-(trifluoromethyl)cyclopropyl]methyl 4-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]oxypiperidine-1-carboxylate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)OC1CCN(CC1)C(=O)OCC1(CC1)C(F)(F)F UQXAADJSEXRGRT-UHFFFAOYSA-N 0.000 description 1
• SVJBTPSWRPRYLT-UHFFFAOYSA-N [1-[2-methyl-3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-(cyclopropylmethyl)carbamate Chemical compound C1(CC1)CNC(OC1CCN(CC1)C1=CC(=C2C(=N1)C(=C(S2)C)C(NC)=O)C(F)(F)F)=O SVJBTPSWRPRYLT-UHFFFAOYSA-N 0.000 description 1
• KQSKHUZTEULJNG-WHUIICBVSA-N [1-[3-(1-hydroxypropyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-[(1S)-1-cyclopropylethyl]carbamate Chemical compound C1(CC1)[C@H](C)NC(OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(CC)O)C(F)(F)F)=O KQSKHUZTEULJNG-WHUIICBVSA-N 0.000 description 1
• UZIWSBYVPWJJEG-UHFFFAOYSA-N [1-[3-(2-methoxyethylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-(cyclopropylmethyl)carbamate Chemical compound C1(CC1)CNC(OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NCCOC)=O)C(F)(F)F)=O UZIWSBYVPWJJEG-UHFFFAOYSA-N 0.000 description 1
• FKHGHWMFYNCHPB-UHFFFAOYSA-N [1-[3-(3-chloroazetidine-1-carbonyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] 3-chloroazetidine-1-carboxylate Chemical compound ClC1CN(C1)C(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)N1CC(C1)Cl)C(F)(F)F FKHGHWMFYNCHPB-UHFFFAOYSA-N 0.000 description 1
• JTMDPXCLPFOIEO-UHFFFAOYSA-N [1-[3-(3-chloropropylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-tert-butylcarbamate hydrochloride Chemical compound CC(C)(C)NC(=O)OC1CCN(CC1)C2=NC3=C(C(=C2)C(F)(F)F)SC=C3C(=O)NCCCCl.Cl JTMDPXCLPFOIEO-UHFFFAOYSA-N 0.000 description 1
• UMCLBGDJVVTOAW-UHFFFAOYSA-N [1-[3-(azetidine-1-carbonyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] 3-chloroazetidine-1-carboxylate Chemical compound ClC1CN(C1)C(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)N1CCC1)C(F)(F)F UMCLBGDJVVTOAW-UHFFFAOYSA-N 0.000 description 1
• RDEVTJXBYMUINE-UHFFFAOYSA-N [1-[3-(azetidine-1-carbonyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] 3-fluoroazetidine-1-carboxylate Chemical compound FC1CN(C1)C(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)N1CCC1)C(F)(F)F RDEVTJXBYMUINE-UHFFFAOYSA-N 0.000 description 1
• FAVSIBRHKMGTHM-UHFFFAOYSA-N [1-[3-(azetidine-1-carbonyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-(cyclopropylmethyl)carbamate Chemical compound C1(CC1)CNC(OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)N1CCC1)C(F)(F)F)=O FAVSIBRHKMGTHM-UHFFFAOYSA-N 0.000 description 1
• QAKGWTWPYQUBBQ-UHFFFAOYSA-N [1-[3-(cyclopropylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-(cyclopropylmethyl)carbamate Chemical compound C1(CC1)CNC(OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC1CC1)=O)C(F)(F)F)=O QAKGWTWPYQUBBQ-UHFFFAOYSA-N 0.000 description 1
• PQIADRWLOLLXBZ-LBPRGKRZSA-N [1-[3-(dimethylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] N-[(2S)-1-cyanopropan-2-yl]carbamate Chemical compound C(#N)C[C@H](C)NC(OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(N(C)C)=O)C(F)(F)F)=O PQIADRWLOLLXBZ-LBPRGKRZSA-N 0.000 description 1
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• GZADUSPAVLILJG-UHFFFAOYSA-N [1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl] 1-oxa-6-azaspiro[3.3]heptane-6-carboxylate Chemical compound O1CCC11CN(C1)C(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(NC)=O)C(F)(F)F GZADUSPAVLILJG-UHFFFAOYSA-N 0.000 description 1
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• PZPUCMHTCUUPSJ-UHFFFAOYSA-N cyclopropylmethyl 7-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]-2,7-diazaspiro[3.5]nonane-2-carboxylate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CCC2(CN(C2)C(=O)OCC2CC2)CC1 PZPUCMHTCUUPSJ-UHFFFAOYSA-N 0.000 description 1
• SLCCZXZLRVJZTR-UHFFFAOYSA-N cyclopropylmethyl N-[1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]azetidin-3-yl]carbamate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CC(C1)NC(OCC1CC1)=O SLCCZXZLRVJZTR-UHFFFAOYSA-N 0.000 description 1
• MSRZLHAFUVUXRZ-UHFFFAOYSA-N cyclopropylmethyl N-[1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl]carbamate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CCC(CC1)NC(OCC1CC1)=O MSRZLHAFUVUXRZ-UHFFFAOYSA-N 0.000 description 1
• CUTUSCCYCWQYPQ-UHFFFAOYSA-N cyclopropylmethyl carbonochloridate Chemical compound ClC(=O)OCC1CC1 CUTUSCCYCWQYPQ-UHFFFAOYSA-N 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 230000002939 deleterious effect Effects 0.000 description 1
• YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
• 239000011903 deuterated solvents‎ Substances 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• SUAKTVZNCRAEJJ-UHFFFAOYSA-N di(propan-2-yl)carbamic acid Chemical compound CC(C)N(C(C)C)C(O)=O SUAKTVZNCRAEJJ-UHFFFAOYSA-N 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
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• 238000009509 drug development Methods 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
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• 238000000132 electrospray ionisation Methods 0.000 description 1
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• 230000007515 enzymatic degradation Effects 0.000 description 1
• 230000009088 enzymatic function Effects 0.000 description 1
• 239000003248 enzyme activator Substances 0.000 description 1
• 150000002118 epoxides Chemical class 0.000 description 1
• YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
• 238000010931 ester hydrolysis Methods 0.000 description 1
• XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
• ITQFPVUDTFABDH-AATRIKPKSA-N ethyl (e)-3-ethoxyprop-2-enoate Chemical compound CCO\C=C\C(=O)OCC ITQFPVUDTFABDH-AATRIKPKSA-N 0.000 description 1
• LFSVADABIDBSBV-UHFFFAOYSA-N ethyl 3-cyclopropyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1CC1 LFSVADABIDBSBV-UHFFFAOYSA-N 0.000 description 1
• YLRGPBKEZVHOAW-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(=O)C(F)(F)F YLRGPBKEZVHOAW-UHFFFAOYSA-N 0.000 description 1
• CBDPWKVOPADMJC-UHFFFAOYSA-N ethyl 4,4-difluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)F CBDPWKVOPADMJC-UHFFFAOYSA-N 0.000 description 1
• 239000002024 ethyl acetate extract Substances 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
• 150000002254 galactosylceramides Chemical class 0.000 description 1
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 102000044289 human ZFYVE16 Human genes 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• NWMFHNMCYBCYQC-UHFFFAOYSA-N hydron N-methyl-5-[1-[(4-methyl-1,3-thiazol-2-yl)methyl]piperidin-4-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxamide chloride Chemical compound [H+].CC1=CSC(=N1)CN2CCC(CC2)C3=NC4=C(C(=C3)C(F)(F)F)SC=C4C(=O)NC.[Cl-] NWMFHNMCYBCYQC-UHFFFAOYSA-N 0.000 description 1
• QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
• 229960002591 hydroxyproline Drugs 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
• 230000026045 iodination Effects 0.000 description 1
• 238000006192 iodination reaction Methods 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 230000002132 lysosomal effect Effects 0.000 description 1
• 210000003712 lysosome Anatomy 0.000 description 1
• 230000001868 lysosomic effect Effects 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 229910001511 metal iodide Inorganic materials 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• HCEDEJWMUMYNEF-UHFFFAOYSA-N methyl 2-methyl-5-oxo-7-(trifluoromethyl)-4h-thieno[3,2-b]pyridine-3-carboxylate Chemical compound FC(F)(F)C1=CC(=O)NC2=C1SC(C)=C2C(=O)OC HCEDEJWMUMYNEF-UHFFFAOYSA-N 0.000 description 1
• XMBUYGCVKKBCSQ-UHFFFAOYSA-N methyl 4-(3-ethoxyprop-2-enoylamino)thiophene-3-carboxylate Chemical compound C(C)OC=CC(=O)NC=1C(=CSC=1)C(=O)OC XMBUYGCVKKBCSQ-UHFFFAOYSA-N 0.000 description 1
• WAZIIMXTDNUMIX-UHFFFAOYSA-N methyl 4-amino-1,2-thiazole-3-carboxylate Chemical compound COC(=O)C1=NSC=C1N WAZIIMXTDNUMIX-UHFFFAOYSA-N 0.000 description 1
• FBGILOYFXFOXPE-UHFFFAOYSA-N methyl 4-amino-2-methylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C=1C(N)=CSC=1C FBGILOYFXFOXPE-UHFFFAOYSA-N 0.000 description 1
• LZGXNJVJHWEJJE-UHFFFAOYSA-N methyl 5,7-dichlorothieno[3,2-b]pyridine-3-carboxylate Chemical compound ClC1=CC(=C2C(=N1)C(=CS2)C(=O)OC)Cl LZGXNJVJHWEJJE-UHFFFAOYSA-N 0.000 description 1
• RHAMVFBHILQDFV-UHFFFAOYSA-N methyl 5-(3,3-difluoro-4-hydroxypiperidin-1-yl)-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound FC1(CN(CCC1O)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)F RHAMVFBHILQDFV-UHFFFAOYSA-N 0.000 description 1
• CWBWRNKGWZATGG-UHFFFAOYSA-N methyl 5-(trifluoromethylsulfonyloxy)thieno[3,2-b]pyridine-3-carboxylate Chemical compound FC(S(=O)(=O)OC1=CC=C2C(=N1)C(=CS2)C(=O)OC)(F)F CWBWRNKGWZATGG-UHFFFAOYSA-N 0.000 description 1
• DXUDKGYKJSYUCR-OLZOCXBDSA-N methyl 5-[(3R,4S)-3-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-6-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1C[C@H]([C@H](CC1)OC1=C(C(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)C)F DXUDKGYKJSYUCR-OLZOCXBDSA-N 0.000 description 1
• GGCREQHQYPSDRJ-UHFFFAOYSA-N methyl 5-[2-(oxetan-3-yloxycarbonyl)-2,6-diazaspiro[3.3]heptan-6-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound O1CC(C1)OC(=O)N1CC2(CN(C2)C2=CC(=C3C(=N2)C(=CS3)C(=O)OC)C(F)(F)F)C1 GGCREQHQYPSDRJ-UHFFFAOYSA-N 0.000 description 1
• RWJDHTDJYWBKEU-UHFFFAOYSA-N methyl 5-[2-[(2-methylpropan-2-yl)oxycarbonyl]-2,6-diazaspiro[3.3]heptan-6-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC2(CN(C2)C2=CC(=C3C(=N2)C(=CS3)C(=O)OC)C(F)(F)F)C1 RWJDHTDJYWBKEU-UHFFFAOYSA-N 0.000 description 1
• GALCINXFXSIFQP-UHFFFAOYSA-N methyl 5-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]ethynyl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC(CC1)C#CC1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F GALCINXFXSIFQP-UHFFFAOYSA-N 0.000 description 1
• VFEXZRUQXBHYNC-UHFFFAOYSA-N methyl 5-[3,3-dimethyl-4-[2-oxo-2-(propan-2-ylamino)ethyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)NC(CN1C(CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)(C)C)=O VFEXZRUQXBHYNC-UHFFFAOYSA-N 0.000 description 1
• SIYNKQHAVLAIBF-UHFFFAOYSA-N methyl 5-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)NC1CN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F SIYNKQHAVLAIBF-UHFFFAOYSA-N 0.000 description 1
• CRWDGMMRERJUFT-UHFFFAOYSA-N methyl 5-[4-(2-oxo-2-phenylmethoxyethyl)piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)=O CRWDGMMRERJUFT-UHFFFAOYSA-N 0.000 description 1
• ZXDAEVJOYZHHHV-UHFFFAOYSA-N methyl 5-[4-(2-oxo-2-piperidin-1-ylethyl)piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound O=C(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)N1CCCCC1 ZXDAEVJOYZHHHV-UHFFFAOYSA-N 0.000 description 1
• DFLMXXKWXQVAHZ-UHFFFAOYSA-N methyl 5-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound O=C(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)N1CCCC1 DFLMXXKWXQVAHZ-UHFFFAOYSA-N 0.000 description 1
• VOEHCPSNUGPVHS-UHFFFAOYSA-N methyl 5-[4-(4-methylpentanoyl)piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound CC(CCC(=O)N1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)C VOEHCPSNUGPVHS-UHFFFAOYSA-N 0.000 description 1
• LBEPNFYCVXZLCL-UHFFFAOYSA-N methyl 5-[4-(4-methylpentyl)piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound CC(CCCN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)C LBEPNFYCVXZLCL-UHFFFAOYSA-N 0.000 description 1
• OFOTYSXIRDBUES-UHFFFAOYSA-N methyl 5-[4-(cyclopropylcarbamoyloxy)piperidin-1-yl]-7-methoxythieno[3,2-b]pyridine-3-carboxylate Chemical compound C1(CC1)NC(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)OC OFOTYSXIRDBUES-UHFFFAOYSA-N 0.000 description 1
• XTGCVGZWAJRXNZ-UHFFFAOYSA-N methyl 5-[4-(cyclopropylmethylcarbamoyloxy)piperidin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1(CC1)CNC(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F XTGCVGZWAJRXNZ-UHFFFAOYSA-N 0.000 description 1
• QUCCWVWMCLBSIR-UHFFFAOYSA-N methyl 5-[4-(tert-butylcarbamoyloxy)piperidin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)NC(=O)OC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F QUCCWVWMCLBSIR-UHFFFAOYSA-N 0.000 description 1
• LWFARLZGVIUNRK-UHFFFAOYSA-N methyl 5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F LWFARLZGVIUNRK-UHFFFAOYSA-N 0.000 description 1
• DXPGXEGAFFMDGM-UHFFFAOYSA-N methyl 5-[4-[(3-propan-2-yloxyazetidin-1-yl)methyl]piperidin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)OC1CN(C1)CC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F DXPGXEGAFFMDGM-UHFFFAOYSA-N 0.000 description 1
• NUNUVNFPRUCRFK-UHFFFAOYSA-N methyl 5-[4-[2-(benzylamino)-2-oxoethyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C1=CC=CC=C1)NC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)=O NUNUVNFPRUCRFK-UHFFFAOYSA-N 0.000 description 1
• LOSIILOUSYYLLG-UHFFFAOYSA-N methyl 5-[4-[2-(cyclohexylamino)-2-oxoethyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1(CCCCC1)NC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)=O LOSIILOUSYYLLG-UHFFFAOYSA-N 0.000 description 1
• HTUSUUMPMPUUKA-UHFFFAOYSA-N methyl 5-[4-[2-(ethylamino)-2-oxoethyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)NC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)=O HTUSUUMPMPUUKA-UHFFFAOYSA-N 0.000 description 1
• IDTGHFQZHUZJBD-UHFFFAOYSA-N methyl 5-[4-[2-(methylamino)-2-oxoethyl]piperazin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound CNC(CN1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)=O IDTGHFQZHUZJBD-UHFFFAOYSA-N 0.000 description 1
• HWYLTELUXUWSDN-UHFFFAOYSA-N methyl 5-[4-[2-oxo-2-(propan-2-ylamino)ethyl]piperidin-1-yl]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)NC(CC1CCN(CC1)C1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)=O HWYLTELUXUWSDN-UHFFFAOYSA-N 0.000 description 1
• IPFZOXYFEVCUJY-NSHDSACASA-N methyl 5-[4-[[(2S)-1-(trifluoromethoxy)propan-2-yl]carbamoyloxy]piperidin-1-yl]thieno[3,2-b]pyridine-3-carboxylate Chemical compound FC(OC[C@H](C)NC(=O)OC1CCN(CC1)C1=CC=C2C(=N1)C(=CS2)C(=O)OC)(F)F IPFZOXYFEVCUJY-NSHDSACASA-N 0.000 description 1
• QFKKHLMVTXBGTP-UHFFFAOYSA-N methyl 5-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]amino]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)NC1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F QFKKHLMVTXBGTP-UHFFFAOYSA-N 0.000 description 1
• AVBIOZAUWYNCCM-UHFFFAOYSA-N methyl 5-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)CNC1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F AVBIOZAUWYNCCM-UHFFFAOYSA-N 0.000 description 1
• NCWGULLVHOTSTO-UHFFFAOYSA-N methyl 5-[[1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]amino]-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC(CC1)NC1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F NCWGULLVHOTSTO-UHFFFAOYSA-N 0.000 description 1
• JSVCKDKUUMSCKQ-UHFFFAOYSA-N methyl 5-chloro-6-methyl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound ClC1=C(C(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)C JSVCKDKUUMSCKQ-UHFFFAOYSA-N 0.000 description 1
• OCDWRNFBOUNHCF-UHFFFAOYSA-N methyl 5-chloro-7-(difluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound ClC1=CC(=C2C(=N1)C(=CS2)C(=O)OC)C(F)F OCDWRNFBOUNHCF-UHFFFAOYSA-N 0.000 description 1
• GVXHSMAJJFVLGD-UHFFFAOYSA-N methyl 5-chloro-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1=C(Cl)N=C2C(C(=O)OC)=CSC2=C1C(F)(F)F GVXHSMAJJFVLGD-UHFFFAOYSA-N 0.000 description 1
• ITGNLLOYEGZIJK-UHFFFAOYSA-N methyl 5-oxo-7-(trifluoromethyl)-4h-thieno[3,2-b]pyridine-3-carboxylate Chemical compound FC(F)(F)C1=CC(=O)NC2=C1SC=C2C(=O)OC ITGNLLOYEGZIJK-UHFFFAOYSA-N 0.000 description 1
• GXOVWRSEVMJDSC-UHFFFAOYSA-N methyl 6-fluoro-5-[1-[2-(trifluoromethoxy)ethoxycarbonyl]piperidin-4-yl]oxy-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound FC=1C(=C2C(=NC=1OC1CCN(CC1)C(=O)OCCOC(F)(F)F)C(=CS2)C(=O)OC)C(F)(F)F GXOVWRSEVMJDSC-UHFFFAOYSA-N 0.000 description 1
• VWTBBVLOKVGDSF-DGCLKSJQSA-N methyl 6-methyl-5-[(2R,4R)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](CC1)OC1=C(C(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)C)C VWTBBVLOKVGDSF-DGCLKSJQSA-N 0.000 description 1
• MQXYPWRUFSKHQZ-UHFFFAOYSA-N methyl 6-methyl-5-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=C2C(=N1)C(=CS2)C(=O)OC)C(F)(F)F)C MQXYPWRUFSKHQZ-UHFFFAOYSA-N 0.000 description 1
• OPUNYZUKJZYTSJ-UHFFFAOYSA-N methyl 6-methyl-5-oxo-7-(trifluoromethyl)-4H-thieno[3,2-b]pyridine-3-carboxylate Chemical compound CC1=C(C2=C(NC1=O)C(=CS2)C(=O)OC)C(F)(F)F OPUNYZUKJZYTSJ-UHFFFAOYSA-N 0.000 description 1
• NMSAPDHKNJKRCE-UHFFFAOYSA-N methyl 7-cyclopropyl-5-(trifluoromethylsulfonyloxy)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1(CC1)C1=C2C(=NC(=C1)OS(=O)(=O)C(F)(F)F)C(=CS2)C(=O)OC NMSAPDHKNJKRCE-UHFFFAOYSA-N 0.000 description 1
• OQTBWUGVQUCEMS-UHFFFAOYSA-N methyl 7-cyclopropyl-5-[4-[2-oxo-2-(propan-2-ylamino)ethyl]piperazin-1-yl]thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1(CC1)C1=C2C(=NC(=C1)N1CCN(CC1)CC(=O)NC(C)C)C(=CS2)C(=O)OC OQTBWUGVQUCEMS-UHFFFAOYSA-N 0.000 description 1
• ZDEGBNGGSXBWTN-UHFFFAOYSA-N methyl 7-cyclopropyl-5-oxo-4H-thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1(CC1)C=1C2=C(NC(C=1)=O)C(=CS2)C(=O)OC ZDEGBNGGSXBWTN-UHFFFAOYSA-N 0.000 description 1
• VOYFWYKXNJRTDB-UHFFFAOYSA-N methyl 7-methyl-5-(trifluoromethylsulfonyloxy)thieno[3,2-b]pyridine-3-carboxylate Chemical compound CC1=C2C(=NC(=C1)OS(=O)(=O)C(F)(F)F)C(=CS2)C(=O)OC VOYFWYKXNJRTDB-UHFFFAOYSA-N 0.000 description 1
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• NEMXVXVJGXZDRR-UHFFFAOYSA-N tert-butyl n-(azetidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CNC1 NEMXVXVJGXZDRR-UHFFFAOYSA-N 0.000 description 1
• PDAFIZPRSXHMCO-LURJTMIESA-N tert-butyl n-[(2s)-1-hydroxypropan-2-yl]carbamate Chemical compound OC[C@H](C)NC(=O)OC(C)(C)C PDAFIZPRSXHMCO-LURJTMIESA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 231100001274 therapeutic index Toxicity 0.000 description 1
• 230000008719 thickening Effects 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• TXILARJHUMCXEK-BMSJAHLVSA-N trideuteriomethyl N-[1-[3-(methylcarbamoyl)-7-(trifluoromethyl)thieno[3,2-b]pyridin-5-yl]piperidin-4-yl]carbamate Chemical compound CNC(=O)C1=CSC=2C1=NC(=CC=2C(F)(F)F)N1CCC(CC1)NC(OC([2H])([2H])[2H])=O TXILARJHUMCXEK-BMSJAHLVSA-N 0.000 description 1
• NMIMXNQEBDWQQM-UHFFFAOYSA-N trifluoromethyl thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1=CN=C2C(C(=O)OC(F)(F)F)=CSC2=C1 NMIMXNQEBDWQQM-UHFFFAOYSA-N 0.000 description 1
• 239000002676 xenobiotic agent Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1