TW202328121A - 環狀磺醯胺核糖核苷酸還原酶(rnr)抑制劑及其用途 - Google Patents

Info

Publication number

TW202328121A

TW202328121A TW111134951A TW111134951A TW202328121A TW 202328121 A TW202328121 A TW 202328121A TW 111134951 A TW111134951 A TW 111134951A TW 111134951 A TW111134951 A TW 111134951A TW 202328121 A TW202328121 A TW 202328121A

Authority

TW

Taiwan

Prior art keywords

alkyl

pharmaceutically acceptable

tautomer

solvate

stereoisomer

Prior art date

2021-09-17

Links

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• -1 Cyclic sulfonamide Chemical class 0.000 title claims abstract description 355
• 102000000505 Ribonucleotide Reductases Human genes 0.000 title claims description 43
• 108010041388 Ribonucleotide Reductases Proteins 0.000 title claims description 43
• 239000003112 inhibitor Substances 0.000 title abstract description 50
• 229940124530 sulfonamide Drugs 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 391
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 93
• 238000000034 method Methods 0.000 claims abstract description 58
• 201000011510 cancer Diseases 0.000 claims abstract description 39
• 238000011282 treatment Methods 0.000 claims abstract description 26
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 145
• 229910052736 halogen Inorganic materials 0.000 claims description 120
• 150000002367 halogens Chemical class 0.000 claims description 119
• 150000003839 salts Chemical class 0.000 claims description 118
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 105
• 229910052739 hydrogen Inorganic materials 0.000 claims description 105
• 239000012453 solvate Substances 0.000 claims description 105
• 239000001257 hydrogen Substances 0.000 claims description 103
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 97
• 125000003118 aryl group Chemical group 0.000 claims description 97
• 125000001072 heteroaryl group Chemical group 0.000 claims description 90
• 230000002829 reductive effect Effects 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 76
• 229910052805 deuterium Inorganic materials 0.000 claims description 73
• 229910052757 nitrogen Inorganic materials 0.000 claims description 72
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 68
• 150000002431 hydrogen Chemical class 0.000 claims description 67
• 229910052760 oxygen Inorganic materials 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 125000005842 heteroatom Chemical group 0.000 claims description 58
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 52
• 229910052717 sulfur Inorganic materials 0.000 claims description 46
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 43
• 210000004881 tumor cell Anatomy 0.000 claims description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 239000003814 drug Substances 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 125000004429 atom Chemical group 0.000 claims description 29
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 19
• 229940124597 therapeutic agent Drugs 0.000 claims description 17
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• 125000001424 substituent group Chemical group 0.000 claims description 15
• 230000008685 targeting Effects 0.000 claims description 15
• 230000012010 growth Effects 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
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• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 239000002904 solvent Substances 0.000 claims description 8
• 230000005764 inhibitory process Effects 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 150000003536 tetrazoles Chemical class 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
• 230000010076 replication Effects 0.000 claims description 4
• 150000003852 triazoles Chemical class 0.000 claims description 4
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 3
• RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 claims description 2
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
• 238000003786 synthesis reaction Methods 0.000 description 93
• 230000015572 biosynthetic process Effects 0.000 description 83
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 77
• 239000012267 brine Substances 0.000 description 73
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 73
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• 239000000706 filtrate Substances 0.000 description 70
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• 239000011734 sodium Substances 0.000 description 34
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• 235000011152 sodium sulphate Nutrition 0.000 description 34
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 33
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
• 239000002585 base Substances 0.000 description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 22
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
• 239000000126 substance Substances 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 239000012043 crude product Substances 0.000 description 20
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 19
• 239000003795 chemical substances by application Substances 0.000 description 19
• 239000012298 atmosphere Substances 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 17
• 238000005481 NMR spectroscopy Methods 0.000 description 17
• 230000001225 therapeutic effect Effects 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
• 238000002953 preparative HPLC Methods 0.000 description 14
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 13
• 125000003545 alkoxy group Chemical group 0.000 description 13
• 125000001188 haloalkyl group Chemical group 0.000 description 13
• 125000004404 heteroalkyl group Chemical group 0.000 description 13
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 12
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• 150000001412 amines Chemical class 0.000 description 12
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
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