JP7167155B2 - ドーパミン－β－ヒドロキシラーゼ阻害剤 - Google Patents

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Publication number

JP7167155B2

JP7167155B2 JP2020530502A JP2020530502A JP7167155B2 JP 7167155 B2 JP7167155 B2 JP 7167155B2 JP 2020530502 A JP2020530502 A JP 2020530502A JP 2020530502 A JP2020530502 A JP 2020530502A JP 7167155 B2 JP7167155 B2 JP 7167155B2

Authority

JP

Japan

Prior art keywords

methyl

pyrrolo

thioxo

imidazol

tetrahydro

Prior art date

2017-12-04

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 229940123041 Dopamine b hydroxylase inhibitor Drugs 0.000 title 1
• -1 C 1 -C 3 alkoxy Chemical group 0.000 claims description 553
• 229910052739 hydrogen Inorganic materials 0.000 claims description 272
• 150000001875 compounds Chemical class 0.000 claims description 257
• 239000001257 hydrogen Substances 0.000 claims description 164
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 136
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 100
• 125000001424 substituent group Chemical group 0.000 claims description 67
• 150000002431 hydrogen Chemical class 0.000 claims description 58
• 125000001153 fluoro group Chemical group F* 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 38
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 35
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 33
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 239000012453 solvate Substances 0.000 claims description 30
• 125000005843 halogen group Chemical group 0.000 claims description 29
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 21
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 17
• 125000002757 morpholinyl group Chemical group 0.000 claims description 16
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 125000003368 amide group Chemical group 0.000 claims description 15
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 14
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 14
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 230000005764 inhibitory process Effects 0.000 claims description 13
• 238000002560 therapeutic procedure Methods 0.000 claims description 13
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
• 230000001668 ameliorated effect Effects 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 7
• 108010015720 Dopamine beta-Hydroxylase Proteins 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 102100033156 Dopamine beta-hydroxylase Human genes 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 claims description 5
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
• GSJJVNAPLSISFR-CQSZACIVSA-N (6S)-1-benzyl-6-(3,5-difluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazole-3-thione Chemical compound C(C1=CC=CC=C1)C1=C2N(C(N1)=S)C[C@@H](C2)C1=CC(=CC(=C1)F)F GSJJVNAPLSISFR-CQSZACIVSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• 210000000653 nervous system Anatomy 0.000 claims 2
• 239000008177 pharmaceutical agent Substances 0.000 claims 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1615
• 238000005481 NMR spectroscopy Methods 0.000 description 537
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 183
• 239000007787 solid Substances 0.000 description 183
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 170
• 239000000203 mixture Substances 0.000 description 168
• 239000000843 powder Substances 0.000 description 151
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 116
• 239000000243 solution Substances 0.000 description 111
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 100
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 83
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 80
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 75
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 72
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 72
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 63
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• 239000012074 organic phase Substances 0.000 description 54
• 239000003208 petroleum Substances 0.000 description 54
• 239000000047 product Substances 0.000 description 52
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 50
• 235000019341 magnesium sulphate Nutrition 0.000 description 50
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 239000003921 oil Substances 0.000 description 43
• 239000006071 cream Substances 0.000 description 35
• 238000006243 chemical reaction Methods 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 238000004587 chromatography analysis Methods 0.000 description 30
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
• ODBYONWDYFNMHM-QMMMGPOBSA-N 1-imidazol-1-yl-2-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound C1=C(C(=C(C(=C1F)F)[C@H]1CC2=C(CC(=O)N3C=CN=C3)NC(=S)N2C1)F)F ODBYONWDYFNMHM-QMMMGPOBSA-N 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 25
• 239000002904 solvent Substances 0.000 description 22
• SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 21
• 238000010992 reflux Methods 0.000 description 21
• 238000000034 method Methods 0.000 description 20
• 239000000725 suspension Substances 0.000 description 19
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• 125000004429 atom Chemical group 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 239000000126 substance Substances 0.000 description 17
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• 239000008346 aqueous phase Substances 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000003112 inhibitor Substances 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• 238000001816 cooling Methods 0.000 description 13
• 239000006260 foam Substances 0.000 description 13
• 208000002815 pulmonary hypertension Diseases 0.000 description 13
• VDEZBFWJJWGEQP-KPZWWZAWSA-N 2-[(2R,4S)-4-(5-bromo-2-fluorophenyl)-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]-1-imidazol-1-ylethanone Chemical compound BrC=1C=CC(=C(C=1)[C@]12[C@H](C=3N(C(NC=3CC(=O)N3C=NC=C3)=S)C1)C2)F VDEZBFWJJWGEQP-KPZWWZAWSA-N 0.000 description 12
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 12
• ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 12
• 229940116357 potassium thiocyanate Drugs 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 229960002748 norepinephrine Drugs 0.000 description 11
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 11
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
• VBASVPJWSSAMQB-ORAYPTAESA-N 2-[(2R,4S)-4-(5-chloro-2-fluorophenyl)-8-methyl-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]-1-imidazol-1-ylethanone Chemical compound ClC=1C=CC(=C(C=1)[C@]12[C@H](C=3N(C(N(C=3CC(=O)N3C=NC=C3)C)=S)C1)C2)F VBASVPJWSSAMQB-ORAYPTAESA-N 0.000 description 8
• SGEDTXBAHUVVGZ-LURJTMIESA-N 3-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]propanoic acid Chemical compound FC1=C(F)C([C@H]2CC3=C(CCC(=O)O)NC(=S)N3C2)=C(F)C(F)=C1 SGEDTXBAHUVVGZ-LURJTMIESA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• 229910052717 sulfur Inorganic materials 0.000 description 8
• WQEQBHIEWDYBAD-ORAYPTAESA-N 2-[(2R,4S)-4-(5-bromo-2-fluorophenyl)-8-methyl-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]-1-imidazol-1-ylethanone Chemical compound BrC=1C=CC(=C(C=1)[C@]12[C@H](C=3N(C(N(C=3CC(=O)N3C=NC=C3)C)=S)C1)C2)F WQEQBHIEWDYBAD-ORAYPTAESA-N 0.000 description 7
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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• 206010007559 Cardiac failure congestive Diseases 0.000 description 6
• WLKZARMZAGUYMF-SECBINFHSA-N ClC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CNC(=O)C2CC2)=S)C1)F Chemical compound ClC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CNC(=O)C2CC2)=S)C1)F WLKZARMZAGUYMF-SECBINFHSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
• 150000007942 carboxylates Chemical class 0.000 description 6
• 210000003169 central nervous system Anatomy 0.000 description 6
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• 238000002425 crystallisation Methods 0.000 description 6
• 230000008025 crystallization Effects 0.000 description 6
• 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 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 230000003389 potentiating effect Effects 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• BPAFRUPGJHTCGM-RCOVLWMOSA-N (2S)-2-amino-3-[[2-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetyl]amino]propanoic acid Chemical compound C1(=CC(=C(C(=C1F)[C@H]1CC2=C(CC(=O)NC[C@@H](C(=O)O)N)NC(=S)N2C1)F)F)F BPAFRUPGJHTCGM-RCOVLWMOSA-N 0.000 description 5
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• JXEIXABRWBQQEZ-LURJTMIESA-N CN1C(N2C(=C1CC(=O)O)C[C@@H](C2)C1=C(C(=CC(=C1F)F)F)F)=S Chemical compound CN1C(N2C(=C1CC(=O)O)C[C@@H](C2)C1=C(C(=CC(=C1F)F)F)F)=S JXEIXABRWBQQEZ-LURJTMIESA-N 0.000 description 5
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
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• 125000002950 monocyclic group Chemical group 0.000 description 5
• YZZVIKDAOTXDEB-JTQLQIEISA-N nepicastat Chemical compound NCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2CC1 YZZVIKDAOTXDEB-JTQLQIEISA-N 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 239000012279 sodium borohydride Substances 0.000 description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 238000001665 trituration Methods 0.000 description 5
• OWNKZEBRQLFXSU-PGECJRHESA-N (1R,5S)-5-(2,5-difluorophenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1C[C@]2(C[C@H]2C1C(O)=O)c1cc(F)ccc1F OWNKZEBRQLFXSU-PGECJRHESA-N 0.000 description 4
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• UKZFLUNJJOVAGB-RYUDHWBXSA-N 1-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound C1=C(C(=C(C(=C1F)F)[C@H]1CC2=C(CC(=O)N3CCC[C@H]3COC)N(C(=S)N2C1)C)F)F UKZFLUNJJOVAGB-RYUDHWBXSA-N 0.000 description 2
• YJKDJHODMAZALQ-STQMWFEESA-N 1-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,6-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound COC[C@@H]1CCCN1C(=O)Cc1c2C[C@@H](Cn2c(=S)n1C)c1c(F)ccc(F)c1F YJKDJHODMAZALQ-STQMWFEESA-N 0.000 description 2
• PYEKZVVSNMYEEK-SBNLOKMTSA-N 1-[(2S)-2-[6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]thiomorpholin-4-yl]ethanone Chemical compound BrC=1C(=C(C(=CC=1)F)C1CC=2N(C(NC=2[C@H]2SCCN(C2)C(C)=O)=S)C1)F PYEKZVVSNMYEEK-SBNLOKMTSA-N 0.000 description 2
• UGUPNFIAZKKDJO-WDEREUQCSA-N 1-[(3R)-3-fluoropyrrolidin-1-yl]-2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,6-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound F[C@H]1CN(CC1)C(CC1=C2N(C(N1C)=S)C[C@H](C2)C1=C(C(=CC=C1F)F)F)=O UGUPNFIAZKKDJO-WDEREUQCSA-N 0.000 description 2
• KNUCLHFCAGYCQY-VXGBXAGGSA-N 1-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]cyclopropane-1-carboxamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(C3(CC3)C(=O)N[C@H]3COCC3)N(C(=S)N2C1)C)F)Br KNUCLHFCAGYCQY-VXGBXAGGSA-N 0.000 description 2
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 2
• CDCGCFGTBMOVHJ-JTQLQIEISA-N 1-[2-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetyl]piperidine-4-carboxamide Chemical compound C1=C(C(=C(C(=C1F)F)[C@H]1CC2=C(CC(=O)N3CCC(CC3)C(=O)N)NC(=S)N2C1)F)F CDCGCFGTBMOVHJ-JTQLQIEISA-N 0.000 description 2
• NEKPGQOYPVESNC-NSHDSACASA-N 1-[4-(hydroxymethyl)piperidin-1-yl]-2-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound FC1=C(F)C([C@H]2CC3=C(CC(=O)N4CCC(CC4)CO)NC(=S)N3C2)=C(F)C(F)=C1 NEKPGQOYPVESNC-NSHDSACASA-N 0.000 description 2
• XNYYRCLESNRBGP-JTQLQIEISA-N 1-morpholin-4-yl-3-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]propan-1-one Chemical compound C1=C(C(=C(C(=C1F)F)[C@H]1CC2=C(CCC(=O)N3CCOCC3)NC(=S)N2C1)F)F XNYYRCLESNRBGP-JTQLQIEISA-N 0.000 description 2
• MRWNVANDLNSBLP-NSHDSACASA-N 1-piperidin-1-yl-3-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]propan-1-one Chemical compound C1=C(C(=C(C(=C1F)F)[C@H]1CC2=C(CCC(=O)N3CCCCC3)NC(=S)N2C1)F)F MRWNVANDLNSBLP-NSHDSACASA-N 0.000 description 2
• RKOIYCWHKHOMRR-VIFPVBQESA-N 1-pyrrolidin-1-yl-2-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound Fc1cc(F)c(F)c([C@H]2Cc3c(CC(=O)N4CCCC4)[nH]c(=S)n3C2)c1F RKOIYCWHKHOMRR-VIFPVBQESA-N 0.000 description 2
• RKOIYCWHKHOMRR-SECBINFHSA-N 1-pyrrolidin-1-yl-2-[(6S)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]ethanone Chemical compound N1(CCCC1)C(CC1=C2N(C(N1)=S)C[C@@H](C2)C1=C(C(=CC(=C1F)F)F)F)=O RKOIYCWHKHOMRR-SECBINFHSA-N 0.000 description 2
• NEZMBAPPFRPZGX-JTQLQIEISA-N 1-pyrrolidin-1-yl-3-[(6R)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]propan-1-one Chemical compound FC1=CC(F)=C(F)C([C@@H]2CN3C(=S)NC(CCC(=O)N4CCCC4)=C3C2)=C1F NEZMBAPPFRPZGX-JTQLQIEISA-N 0.000 description 2
• PTHSRHPSAYFQIT-YBTHPKLGSA-N 2-[(2R,4S)-4-(3-chloro-2,6-difluorophenyl)-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]-N-(2-pyrazol-1-ylethyl)acetamide Chemical compound FC1=C(C(F)=C(Cl)C=C1)[C@]12C[C@H]1C1=C(CC(=O)NCCN3C=CC=N3)NC(=S)N1C2 PTHSRHPSAYFQIT-YBTHPKLGSA-N 0.000 description 2
• VFUNOJXIRYTQRU-OVWNDWIMSA-N 2-[(2R,4S)-4-(3-chloro-2,6-difluorophenyl)-8-methyl-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]-1-imidazol-1-ylethanone Chemical compound ClC=1C(=C(C(=CC=1)F)[C@]12[C@H](C=3N(C(N(C=3CC(=O)N3C=NC=C3)C)=S)C1)C2)F VFUNOJXIRYTQRU-OVWNDWIMSA-N 0.000 description 2
• VKKRXOFSANASGC-NLQQUQSOSA-N 2-[(2R,4S)-4-(3-chloro-2,6-difluorophenyl)-8-methyl-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound C1=C(C(=C(C(=C1)F)[C@]12C[C@H]1C1=C(CC(=O)N[C@H]3COCC3)N(C(=S)N1C2)C)F)Cl VKKRXOFSANASGC-NLQQUQSOSA-N 0.000 description 2
• BWSQRKBURJRBDQ-GYKQLYQFSA-N 2-[(2R,4S)-4-(3-chloro-2,6-difluorophenyl)-8-methyl-7-sulfanylidene-6,8-diazatricyclo[4.3.0.02,4]non-1(9)-en-9-yl]acetic acid Chemical compound C1=CC(=C(C(=C1F)[C@]12[C@H](C3=C(CC(=O)O)N(C(=S)N3C1)C)C2)F)Cl BWSQRKBURJRBDQ-GYKQLYQFSA-N 0.000 description 2
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• GQVYBFUIMLRBBT-JTQLQIEISA-N 2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(oxan-4-yl)acetamide Chemical compound CN1C(N2C(=C1CC(=O)NC1CCOCC1)C[C@@H](C2)C1=C(C(=CC(=C1F)F)F)F)=S GQVYBFUIMLRBBT-JTQLQIEISA-N 0.000 description 2
• YPKFWFKCIUAKPG-WDEREUQCSA-N 2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxan-3-yl]acetamide Chemical compound CN1C(N2C(=C1CC(=O)N[C@H]1COCCC1)C[C@@H](C2)C1=C(C(=CC(=C1F)F)F)F)=S YPKFWFKCIUAKPG-WDEREUQCSA-N 0.000 description 2
• AITAJJZKKURGAF-VHSXEESVSA-N 2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound CN1C(N2C(=C1CC(=O)N[C@H]1COCC1)C[C@@H](C2)C1=C(C(=CC(=C1F)F)F)F)=S AITAJJZKKURGAF-VHSXEESVSA-N 0.000 description 2
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• OJQTVTLJDWZMAJ-BONVTDFDSA-N 2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,6-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-1-[(2S)-2-(trifluoromethyl)pyrrolidin-1-yl]ethanone Chemical compound CN1C(N2C(=C1CC(=O)N1[C@@H](CCC1)C(F)(F)F)C[C@@H](C2)C1=C(C(=CC=C1F)F)F)=S OJQTVTLJDWZMAJ-BONVTDFDSA-N 0.000 description 2
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• JKMPBBFZLKKVAK-WDEREUQCSA-N 2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,6-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound FC1=C(F)C([C@H]2CC3=C(CC(=O)N[C@H]4COCC4)N(C(=S)N3C2)C)=C(F)C=C1 JKMPBBFZLKKVAK-WDEREUQCSA-N 0.000 description 2
• JKMPBBFZLKKVAK-QWRGUYRKSA-N 2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,6-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3S)-oxolan-3-yl]acetamide Chemical compound Cn1c(CC(=O)N[C@H]2CCOC2)c2C[C@@H](Cn2c1=S)c1c(F)ccc(F)c1F JKMPBBFZLKKVAK-QWRGUYRKSA-N 0.000 description 2
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• GPTGBZHFTPODLJ-QMMMGPOBSA-N 2-[(6R)-6-(2,5-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-methylsulfonylacetamide Chemical compound FC1=C(C=C(C=C1)F)[C@H]1CC=2N(C(NC=2CC(=O)NS(=O)(=O)C)=S)C1 GPTGBZHFTPODLJ-QMMMGPOBSA-N 0.000 description 2
• PCJPRSKGKJMMGU-WDEREUQCSA-N 2-[(6R)-6-(2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound C1=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)N[C@H]3COCC3)NC(=S)N2C1)F PCJPRSKGKJMMGU-WDEREUQCSA-N 0.000 description 2
• BPBWKYZLCGLHAV-ZETCQYMHSA-N 2-[(6R)-6-(2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetic acid Chemical compound FC1=C(C(=CC=C1)F)[C@H]1CC=2N(C(NC=2CC(=O)O)=S)C1 BPBWKYZLCGLHAV-ZETCQYMHSA-N 0.000 description 2
• IIVVVEAWNFFVBY-VUWPPUDQSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(3-hydroxypiperidin-1-yl)ethanone Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)N3CCCC(C3)O)NC(=S)N2C1)F)Br IIVVVEAWNFFVBY-VUWPPUDQSA-N 0.000 description 2
• ARFGJLCFBWMQAQ-VUWPPUDQSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(3-methylsulfonylpyrrolidin-1-yl)ethanone Chemical compound BrC1=C(F)C([C@H]2CC3=C(CC(=O)N4CCC(C4)S(=O)(=O)C)NC(=S)N3C2)=C(F)C=C1 ARFGJLCFBWMQAQ-VUWPPUDQSA-N 0.000 description 2
• SCJAFIADKWOXRN-JTQLQIEISA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(4,4-difluoropiperidin-1-yl)ethanone Chemical compound BrC=1C(=C(C(=CC=1)F)[C@H]1CC=2N(C(NC=2CC(=O)N2CCC(CC2)(F)F)=S)C1)F SCJAFIADKWOXRN-JTQLQIEISA-N 0.000 description 2
• KLHQYEKRTCFTPD-NSHDSACASA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(4-methylsulfonylpiperidin-1-yl)ethanone Chemical compound BrC=1C(=C(C(=CC=1)F)[C@H]1CC=2N(C(NC=2CC(=O)N2CCC(CC2)S(=O)(=O)C)=S)C1)F KLHQYEKRTCFTPD-NSHDSACASA-N 0.000 description 2
• YJYAESYXKDGDBU-JTQLQIEISA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-morpholin-4-ylethanone Chemical compound BrC=1C(=C(C(=CC=1)F)[C@H]1CC=2N(C(NC=2CC(=O)N2CCOCC2)=S)C1)F YJYAESYXKDGDBU-JTQLQIEISA-N 0.000 description 2
• ZBVNOUVCBOPRMX-JTQLQIEISA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(1,1-dioxothian-4-yl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)NC3CCS(=O)(=O)CC3)NC(=S)N2C1)F)Br ZBVNOUVCBOPRMX-JTQLQIEISA-N 0.000 description 2
• LGZXHVWZGRXYRS-VIFPVBQESA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-hydroxyethyl)-N-methylacetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@H]1CC=2N(C(NC=2CC(=O)N(C)CCO)=S)C1)F LGZXHVWZGRXYRS-VIFPVBQESA-N 0.000 description 2
• VLOBPJIALNWLNB-QMMMGPOBSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-hydroxyethyl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)NCCO)NC(=S)N2C1)F)Br VLOBPJIALNWLNB-QMMMGPOBSA-N 0.000 description 2
• WGWUKZPAWQBGJY-VIFPVBQESA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-methylsulfonylethyl)acetamide Chemical compound C1=C(Br)C(F)=C([C@H]2CC3=C(CC(=O)NCCS(=O)(=O)C)NC(=S)N3C2)C(F)=C1 WGWUKZPAWQBGJY-VIFPVBQESA-N 0.000 description 2
• CMOIIPYTVXVSIB-YMNIQAILSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-oxooxolan-3-yl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)NC3C(=O)OCC3)NC(=S)N2C1)F)Br CMOIIPYTVXVSIB-YMNIQAILSA-N 0.000 description 2
• RGDYVPIHOZRULF-QMMMGPOBSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(cyanomethyl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@H]1CC=2N(C(NC=2CC(=O)NCC#N)=S)C1)F RGDYVPIHOZRULF-QMMMGPOBSA-N 0.000 description 2
• QCAWDDIDRJVUOW-NSHDSACASA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(pyridin-2-ylmethyl)acetamide Chemical compound BrC=1C(=C(C(=CC1)F)[C@H]1CC=2N(C(NC2CC(=O)NCC2=NC=CC=C2)=S)C1)F QCAWDDIDRJVUOW-NSHDSACASA-N 0.000 description 2
• XLAPMBZLGRYTND-OCCSQVGLSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(1R)-1-cyclohexylethyl]acetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)N[C@@H](C3CCCCC3)C)NC(=S)N2C1)F)Br XLAPMBZLGRYTND-OCCSQVGLSA-N 0.000 description 2
• WQLVBIMCATURSC-OWRWGESLSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(1R,2R)-2-hydroxycyclohexyl]acetamide Chemical compound C1=C(Br)C(F)=C([C@H]2CC3=C(CC(=O)N[C@H]4[C@@H](CCCC4)O)NC(=S)N3C2)C(F)=C1 WQLVBIMCATURSC-OWRWGESLSA-N 0.000 description 2
• PRHQTHMECYEYPR-FMSQNYNMSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(1S,2S)-2-hydroxycyclopentyl]acetamide Chemical compound BrC1=C(F)C([C@H]2CC3=C(CC(=O)N[C@@H]4[C@@H](O)CCC4)NC(=S)N3C2)=C(F)C=C1 PRHQTHMECYEYPR-FMSQNYNMSA-N 0.000 description 2
• SBFDCSUFKLTYMF-VHSXEESVSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)N[C@H]3COCC3)NC(=S)N2C1)F)Br SBFDCSUFKLTYMF-VHSXEESVSA-N 0.000 description 2
• KILLRSHKHFNNBJ-CVZZAPKMSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[2-(hydroxymethyl)cyclopentyl]acetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)NC3C(CO)CCC3)NC(=S)N2C1)F)Br KILLRSHKHFNNBJ-CVZZAPKMSA-N 0.000 description 2
• LGEDMJSCYQAOAI-LBPRGKRZSA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-cyclohexyl-N-methylacetamide Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)N(C)C3CCCCC3)NC(=S)N2C1)F)Br LGEDMJSCYQAOAI-LBPRGKRZSA-N 0.000 description 2
• CXNKDPBEUPXSPJ-NSHDSACASA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-(oxan-4-yl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@H]1CC=2N(C(NC=2CC(=O)N(C2CCOCC2)C)=S)C1)F CXNKDPBEUPXSPJ-NSHDSACASA-N 0.000 description 2
• AGIGGKDZDARFQV-VIFPVBQESA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-propan-2-ylacetamide Chemical compound BrC1=C(F)C([C@H]2CC3=C(CC(=O)NC(C)C)NC(=S)N3C2)=C(F)C=C1 AGIGGKDZDARFQV-VIFPVBQESA-N 0.000 description 2
• WYRQDMGXTDQFKA-LURJTMIESA-N 2-[(6R)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetic acid Chemical compound C1(=CC=C(C(=C1F)[C@H]1CC2=C(CC(=O)O)NC(=S)N2C1)F)Br WYRQDMGXTDQFKA-LURJTMIESA-N 0.000 description 2
• HSNHZINTVZCDFM-WCQYABFASA-N 2-[(6R)-6-(5-chloro-2-fluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound ClC1=CC=C(C([C@H]2CC3=C(CC(=O)N[C@H]4COCC4)N(C(=S)N3C2)C)=C1)F HSNHZINTVZCDFM-WCQYABFASA-N 0.000 description 2
• XYTGLPXAFFRWGC-LBPRGKRZSA-N 2-[(6R)-6-(5-chloro-2-fluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-cyclopentylacetamide Chemical compound C1(=CC=C(C([C@H]2CC3=C(CC(=O)NC4CCCC4)N(C(=S)N3C2)C)=C1)F)Cl XYTGLPXAFFRWGC-LBPRGKRZSA-N 0.000 description 2
• HVZGFNPGAWFUIY-CMPLNLGQSA-N 2-[(6R)-6-(5-chloro-2-fluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound C1=C(Cl)C=C([C@H]2CC3=C(CC(=O)N[C@H]4COCC4)NC(=S)N3C2)C(F)=C1 HVZGFNPGAWFUIY-CMPLNLGQSA-N 0.000 description 2
• SDAOOXZSHINUBJ-ZETCQYMHSA-N 2-[(6R)-6-(5-chloro-2-fluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetic acid Chemical compound C1(=CC=C(C(=C1)[C@H]1CC2=C(CC(=O)O)NC(=S)N2C1)F)Cl SDAOOXZSHINUBJ-ZETCQYMHSA-N 0.000 description 2
• PJHCEIJPMFQALF-RXMQYKEDSA-N 2-[(6S)-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetic acid Chemical compound C1=C(C(=C(C(=C1F)F)[C@@H]1CC2=C(CC(=O)O)NC(=S)N2C1)F)F PJHCEIJPMFQALF-RXMQYKEDSA-N 0.000 description 2
• OCZJTAMDSRFQRF-MRVPVSSYSA-N 2-[(6S)-6-(3,5-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)O)=S)C1 OCZJTAMDSRFQRF-MRVPVSSYSA-N 0.000 description 2
• HGJHQINCIOZRHN-NEPJUHHUSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]ethanone Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)N3CCC[C@H]3CO)N(C(=S)N2C1)C)F)Br HGJHQINCIOZRHN-NEPJUHHUSA-N 0.000 description 2
• GOSAUQVUEDNFED-LLVKDONJSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-1-morpholin-4-ylethanone Chemical compound BrC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)N3CCOCC3)N(C(=S)N2C1)C GOSAUQVUEDNFED-LLVKDONJSA-N 0.000 description 2
• JFAIONWTIXGPAO-SECBINFHSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(cyanomethyl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)NCC#N)C)=S)C1)F JFAIONWTIXGPAO-SECBINFHSA-N 0.000 description 2
• ACBDUHKODZHRBY-GHMZBOCLSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N[C@H]2COCC2)C)=S)C1)F ACBDUHKODZHRBY-GHMZBOCLSA-N 0.000 description 2
• XEMXSMKKWBQUEM-JHJMLUEUSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-(oxolan-3-yl)acetamide Chemical compound BrC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)N(C3COCC3)C)N(C(=S)N2C1)C XEMXSMKKWBQUEM-JHJMLUEUSA-N 0.000 description 2
• XEXZMKYTAWFIEU-SSDOTTSWSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N)C)=S)C1)F XEXZMKYTAWFIEU-SSDOTTSWSA-N 0.000 description 2
• OVYGMSKEGNENRM-FXADVQPWSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(2-oxa-7-azaspiro[4.4]nonan-7-yl)ethanone Chemical compound C1=C(C(=C(C(F)=C1)[C@@H]1CC2=C(CC(=O)N3CCC4(C3)COCC4)NC(=S)N2C1)F)Br OVYGMSKEGNENRM-FXADVQPWSA-N 0.000 description 2
• DGOANQHIQMMZSW-CYBMUJFWSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(2-oxa-8-azaspiro[4.5]decan-8-yl)ethanone Chemical compound C1=C(C(=C(C(=C1)F)[C@@H]1CC2=C(CC(=O)N3CCC4(CC3)COCC4)NC(=S)N2C1)F)Br DGOANQHIQMMZSW-CYBMUJFWSA-N 0.000 description 2
• ARFGJLCFBWMQAQ-NFJWQWPMSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(3-methylsulfonylpyrrolidin-1-yl)ethanone Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N2CC(CC2)S(=O)(=O)C)=S)C1)F ARFGJLCFBWMQAQ-NFJWQWPMSA-N 0.000 description 2
• BQOSTBSLVWHFTE-LLVKDONJSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)N3CCN(CC3)C)NC(=S)N2C1)F)Br BQOSTBSLVWHFTE-LLVKDONJSA-N 0.000 description 2
• KLHQYEKRTCFTPD-LLVKDONJSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-(4-methylsulfonylpiperidin-1-yl)ethanone Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N2CCC(CC2)S(=O)(=O)C)=S)C1)F KLHQYEKRTCFTPD-LLVKDONJSA-N 0.000 description 2
• KCJXJCFFGRQYQQ-MNOVXSKESA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]ethanone Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N2[C@@H](CCC2)CO)=S)C1)F KCJXJCFFGRQYQQ-MNOVXSKESA-N 0.000 description 2
• YJYAESYXKDGDBU-SNVBAGLBSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-morpholin-4-ylethanone Chemical compound BrC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)N3CCOCC3)NC(=S)N2C1 YJYAESYXKDGDBU-SNVBAGLBSA-N 0.000 description 2
• WERVDGVFHJWJHO-SNVBAGLBSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)N3CCCC3)NC(=S)N2C1)F)Br WERVDGVFHJWJHO-SNVBAGLBSA-N 0.000 description 2
• VLOBPJIALNWLNB-MRVPVSSYSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-hydroxyethyl)acetamide Chemical compound BrC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)NCCO)NC(=S)N2C1 VLOBPJIALNWLNB-MRVPVSSYSA-N 0.000 description 2
• RFGMCQYIPRKYKF-SECBINFHSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-methoxyethyl)acetamide Chemical compound BrC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)NCCOC)NC(=S)N2C1 RFGMCQYIPRKYKF-SECBINFHSA-N 0.000 description 2
• IOGXBMLTXVAZDC-PKEIRNPWSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(2-oxocyclopentyl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NC3C(=O)CCC3)NC(=S)N2C1)F)Br IOGXBMLTXVAZDC-PKEIRNPWSA-N 0.000 description 2
• MOHGMJMSDFEUAI-SNVBAGLBSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(cyclopropylmethyl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)NCC2CC2)=S)C1)F MOHGMJMSDFEUAI-SNVBAGLBSA-N 0.000 description 2
• VOUAGZACHJAAJD-GFCCVEGCSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(pyridin-3-ylmethyl)acetamide Chemical compound C1=CC(=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NCC3=CN=CC=C3)NC(=S)N2C1)F)Br VOUAGZACHJAAJD-GFCCVEGCSA-N 0.000 description 2
• SBFDCSUFKLTYMF-NXEZZACHSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxolan-3-yl]acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N[C@H]2COCC2)=S)C1)F SBFDCSUFKLTYMF-NXEZZACHSA-N 0.000 description 2
• XYWVLPDRSGAVGJ-LLVKDONJSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-butyl-N-methylacetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N(C)CCCC)=S)C1)F XYWVLPDRSGAVGJ-LLVKDONJSA-N 0.000 description 2
• VCAKFZGCRCEYDJ-SECBINFHSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-cyclobutylacetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)NC2CCC2)=S)C1)F VCAKFZGCRCEYDJ-SECBINFHSA-N 0.000 description 2
• RUIAYIPDPZWEBY-MRVPVSSYSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-cyclopropylacetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NC3CC3)NC(=S)N2C1)F)Br RUIAYIPDPZWEBY-MRVPVSSYSA-N 0.000 description 2
• JSXPELCURSHMPL-NFJWQWPMSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-(oxolan-3-yl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N(C2COCC2)C)=S)C1)F JSXPELCURSHMPL-NFJWQWPMSA-N 0.000 description 2
• XMSBMRLAXMUFLY-SSDOTTSWSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-methylsulfonylacetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NS(=O)(=O)C)NC(=S)N2C1)F)Br XMSBMRLAXMUFLY-SSDOTTSWSA-N 0.000 description 2
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• BAMVBKWFEZCUSB-JTQLQIEISA-N 1-methyl-4-[2-[(6R)-2-methyl-3-sulfanylidene-6-(2,3,5,6-tetrafluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]acetyl]piperazin-2-one Chemical compound C1=C(C(=C(C(=C1F)F)[C@H]1CC2=C(CC(=O)N3CC(=O)N(CC3)C)N(C(=S)N2C1)C)F)F BAMVBKWFEZCUSB-JTQLQIEISA-N 0.000 description 1
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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• BIZMDVMCOWPBBU-VXGBXAGGSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxan-3-yl]acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N[C@H]2COCCC2)C)=S)C1)F BIZMDVMCOWPBBU-VXGBXAGGSA-N 0.000 description 1
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• HMDDVRNGOAXVLK-GFCCVEGCSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-(oxan-4-yl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N(C2CCOCC2)C)C)=S)C1)F HMDDVRNGOAXVLK-GFCCVEGCSA-N 0.000 description 1
• XSJOUIFVYDBTIJ-SNVBAGLBSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-(oxetan-3-yl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N(C2COC2)C)C)=S)C1)F XSJOUIFVYDBTIJ-SNVBAGLBSA-N 0.000 description 1
• XEMXSMKKWBQUEM-VXGBXAGGSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-[(3R)-oxolan-3-yl]acetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)N(C)[C@H]3COCC3)N(C(=S)N2C1)C)F)Br XEMXSMKKWBQUEM-VXGBXAGGSA-N 0.000 description 1
• RZMQYBFGSIRDAT-SNVBAGLBSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-(oxan-4-yl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NC3CCOCC3)NC(=S)N2C1)F)Br RZMQYBFGSIRDAT-SNVBAGLBSA-N 0.000 description 1
• HWFOJIIHDUXDHN-GHMZBOCLSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxan-3-yl]acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N[C@H]2COCCC2)=S)C1)F HWFOJIIHDUXDHN-GHMZBOCLSA-N 0.000 description 1
• MECLVARNVVJUMD-SECBINFHSA-N 2-[(6S)-6-(3-bromo-2,6-difluorophenyl)-3-sulfanylidene-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazol-1-yl]-N-methyl-N-(oxetan-3-yl)acetamide Chemical compound BrC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(NC=2CC(=O)N(C2COC2)C)=S)C1)F MECLVARNVVJUMD-SECBINFHSA-N 0.000 description 1
• QDECERGZHNCJMV-SNVBAGLBSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-1-(1,2-oxazolidin-2-yl)ethanone Chemical compound ClC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N2OCCC2)C)=S)C1)F QDECERGZHNCJMV-SNVBAGLBSA-N 0.000 description 1
• SUTVBORCAYUQOF-LLVKDONJSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-1-morpholin-4-ylethanone Chemical compound ClC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)N2CCOCC2)C)=S)C1)F SUTVBORCAYUQOF-LLVKDONJSA-N 0.000 description 1
• YUKXFVWUZURIFH-SECBINFHSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(1,3-oxazol-2-yl)acetamide Chemical compound C1=C(Cl)C(F)=C(C(F)=C1)[C@@H]1CC2=C(CC(=O)NC3=NC=CO3)N(C(=S)N2C1)C YUKXFVWUZURIFH-SECBINFHSA-N 0.000 description 1
• BAHGGPJOBXGQGE-SNVBAGLBSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(1-methylpyrazol-4-yl)acetamide Chemical compound ClC=1C(=C(C(=CC=1)F)[C@@H]1CC=2N(C(N(C=2CC(=O)NC=2C=NN(C=2)C)C)=S)C1)F BAHGGPJOBXGQGE-SNVBAGLBSA-N 0.000 description 1
• XKPGBMAHZBVJCG-SECBINFHSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)acetamide Chemical compound C1(Cl)=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)NC3=NN=C(O3)C)N(C(=S)N2C1)C XKPGBMAHZBVJCG-SECBINFHSA-N 0.000 description 1
• GPKRMDVNHAMTMI-LLVKDONJSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(oxan-4-yl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NC3CCOCC3)N(C(=S)N2C1)C)F)Cl GPKRMDVNHAMTMI-LLVKDONJSA-N 0.000 description 1
• NMRDBWNNSYEQFP-CYBMUJFWSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(oxan-4-ylmethyl)acetamide Chemical compound C1(=CC=C(C(=C1F)[C@@H]1CC2=C(CC(=O)NCC3CCOCC3)N(C(=S)N2C1)C)F)Cl NMRDBWNNSYEQFP-CYBMUJFWSA-N 0.000 description 1
• FVKOBOXGSAXFOK-SECBINFHSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-(oxetan-3-yl)acetamide Chemical compound ClC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)NC3COC3)N(C(=S)N2C1)C FVKOBOXGSAXFOK-SECBINFHSA-N 0.000 description 1
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• ROGUIHGVKYXZBA-GFCCVEGCSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(1-methylpyrazol-4-yl)methyl]acetamide Chemical compound ClC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)NCC3=CN(C)N=C3)N(C(=S)N2C1)C ROGUIHGVKYXZBA-GFCCVEGCSA-N 0.000 description 1
• BWTIRKPHQPMUCE-VXGBXAGGSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-[(3R)-oxan-3-yl]acetamide Chemical compound C1=C(Cl)C(F)=C(C(F)=C1)[C@@H]1CC2=C(CC(=O)N[C@H]3COCCC3)N(C(=S)N2C1)C BWTIRKPHQPMUCE-VXGBXAGGSA-N 0.000 description 1
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• KYAOTQZCZAFORS-GFCCVEGCSA-N 2-[(6S)-6-(3-chloro-2,6-difluorophenyl)-2-methyl-3-sulfanylidene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-1-yl]-N-cyclohexylacetamide Chemical compound ClC1=C(F)C(=C(F)C=C1)[C@@H]1CC2=C(CC(=O)NC3CCCCC3)N(C(=S)N2C1)C KYAOTQZCZAFORS-GFCCVEGCSA-N 0.000 description 1
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