JP7453916B2 - Ｏ－糖タンパク質－２－アセトアミド－２－デオキシ－３－ｄ－グリコピラノシダーゼ阻害剤 - Google Patents

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Publication number

JP7453916B2

JP7453916B2 JP2020548963A JP2020548963A JP7453916B2 JP 7453916 B2 JP7453916 B2 JP 7453916B2 JP 2020548963 A JP2020548963 A JP 2020548963A JP 2020548963 A JP2020548963 A JP 2020548963A JP 7453916 B2 JP7453916 B2 JP 7453916B2

Authority

JP

Japan

Prior art keywords

methyl

pharmaceutically acceptable

acetamide

acceptable salt

thiazol

Prior art date

2018-03-14

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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• 239000003112 inhibitor Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 350
• 150000003839 salts Chemical class 0.000 claims description 173
• 125000005843 halogen group Chemical group 0.000 claims description 101
• -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 49
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 48
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 201000010099 disease Diseases 0.000 claims description 36
• 229910052799 carbon Inorganic materials 0.000 claims description 35
• 125000004970 halomethyl group Chemical group 0.000 claims description 34
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
• 102100030122 Protein O-GlcNAcase Human genes 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
• 108010045982 hexosaminidase C Proteins 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 210000004556 brain Anatomy 0.000 claims description 11
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 125000001246 bromo group Chemical group Br* 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
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• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
• 230000005764 inhibitory process Effects 0.000 claims description 5
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 3
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 191
• 235000002639 sodium chloride Nutrition 0.000 description 153
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 93
• 238000000034 method Methods 0.000 description 80
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 78
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 75
• 239000000203 mixture Substances 0.000 description 73
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
• LAPWQPYYMGKHNZ-UHFFFAOYSA-N n-[5-(chloromethyl)-1,3-thiazol-2-yl]acetamide Chemical compound CC(=O)NC1=NC=C(CCl)S1 LAPWQPYYMGKHNZ-UHFFFAOYSA-N 0.000 description 60
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
• 238000000926 separation method Methods 0.000 description 33
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• 239000000243 solution Substances 0.000 description 32
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 30
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• 238000005481 NMR spectroscopy Methods 0.000 description 28
• 239000000543 intermediate Substances 0.000 description 27
• 235000019439 ethyl acetate Nutrition 0.000 description 26
• 239000000047 product Substances 0.000 description 24
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 23
• ANSMRNCOBLTNBO-UHFFFAOYSA-N 2-bromo-5-fluoropyrimidine Chemical compound FC1=CN=C(Br)N=C1 ANSMRNCOBLTNBO-UHFFFAOYSA-N 0.000 description 21
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
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• KZLHASJXPLGUOE-UHFFFAOYSA-N n-(5-formyl-1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC=C(C=O)S1 KZLHASJXPLGUOE-UHFFFAOYSA-N 0.000 description 16
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• 125000001072 heteroaryl group Chemical group 0.000 description 14
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• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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• 208000027061 mild cognitive impairment Diseases 0.000 description 12
• MGGZYACWICDRRD-UHFFFAOYSA-N tert-butyl 3-(bromomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(CBr)C1 MGGZYACWICDRRD-UHFFFAOYSA-N 0.000 description 12
• CPKMTYPRYKIRQC-UHFFFAOYSA-N tert-butyl 3-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylidene]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C1)=CB1OC(C)(C)C(C)(C)O1 CPKMTYPRYKIRQC-UHFFFAOYSA-N 0.000 description 12
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• 229910004298 SiO 2 Inorganic materials 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
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