IL301690A - Piperidinyl small molecule degraders of helios and methods of use - Google Patents

Info

Publication number

IL301690A

IL301690A IL301690A IL30169023A IL301690A IL 301690 A IL301690 A IL 301690A IL 301690 A IL301690 A IL 301690A IL 30169023 A IL30169023 A IL 30169023A IL 301690 A IL301690 A IL 301690A

Authority

IL

Israel

Prior art keywords

alkyl

group

aryl

cycloalkyl

heteroaryl

Prior art date

2020-10-16

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 282
• 238000000034 method Methods 0.000 title claims description 69
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title 2
• 229910052734 helium Inorganic materials 0.000 title 1
• 239000001307 helium Substances 0.000 title 1
• SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 title 1
• -1 hydroxy, amino Chemical group 0.000 claims description 194
• 125000003118 aryl group Chemical group 0.000 claims description 123
• 125000000217 alkyl group Chemical group 0.000 claims description 110
• 125000001072 heteroaryl group Chemical group 0.000 claims description 101
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 101
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 95
• 229910052739 hydrogen Inorganic materials 0.000 claims description 81
• 239000001257 hydrogen Substances 0.000 claims description 81
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 76
• 230000015572 biosynthetic process Effects 0.000 claims description 66
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
• 125000004432 carbon atom Chemical group C* 0.000 claims description 64
• 229910052799 carbon Inorganic materials 0.000 claims description 60
• 208000035475 disorder Diseases 0.000 claims description 60
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 48
• 125000002950 monocyclic group Chemical group 0.000 claims description 45
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
• 206010028980 Neoplasm Diseases 0.000 claims description 41
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 201000010099 disease Diseases 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 35
• 125000004429 atom Chemical group 0.000 claims description 34
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
• 201000011510 cancer Diseases 0.000 claims description 30
• 102100037796 Zinc finger protein Helios Human genes 0.000 claims description 28
• 101000599037 Homo sapiens Zinc finger protein Helios Proteins 0.000 claims description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 125000003003 spiro group Chemical group 0.000 claims description 25
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 239000000651 prodrug Substances 0.000 claims description 24
• 229940002612 prodrug Drugs 0.000 claims description 24
• 125000001188 haloalkyl group Chemical group 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 19
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 206010009944 Colon cancer Diseases 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 230000015556 catabolic process Effects 0.000 claims description 12
• 238000006731 degradation reaction Methods 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical group 0.000 claims description 12
• 201000001441 melanoma Diseases 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
• 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims description 8
• 239000013078 crystal Substances 0.000 claims description 8
• 208000022679 triple-negative breast carcinoma Diseases 0.000 claims description 8
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
• 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 7
• 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 7
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 7
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 7
• 125000001769 aryl amino group Chemical group 0.000 claims description 7
• 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 7
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 7
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 7
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
• 208000002458 carcinoid tumor Diseases 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 7
• 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims description 7
• 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 7
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 7
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 7
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 7
• 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 7
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 7
• 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 7
• 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 7
• 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 7
• AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 7
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 7
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 7
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
• 208000017604 Hodgkin disease Diseases 0.000 claims description 6
• 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 6
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 6
• 206010042971 T-cell lymphoma Diseases 0.000 claims description 6
• 125000003368 amide group Chemical group 0.000 claims description 6
• 230000008901 benefit Effects 0.000 claims description 6
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 5
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 208000025113 myeloid leukemia Diseases 0.000 claims description 5
• 208000008732 thymoma Diseases 0.000 claims description 5
• 101000869592 Daucus carota Major allergen Dau c 1 Proteins 0.000 claims description 4
• 101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Proteins 0.000 claims description 4
• 208000000389 T-cell leukemia Diseases 0.000 claims description 4
• 102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 claims description 4
• 108091092878 Microsatellite Proteins 0.000 claims description 3
• 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims description 3
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims 20
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 177
• 239000000203 mixture Substances 0.000 description 96
• 239000007787 solid Substances 0.000 description 83
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
• 239000000243 solution Substances 0.000 description 69
• 239000011541 reaction mixture Substances 0.000 description 68
• 235000019439 ethyl acetate Nutrition 0.000 description 66
• 210000004027 cell Anatomy 0.000 description 60
• 238000003786 synthesis reaction Methods 0.000 description 55
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
• 125000000623 heterocyclic group Chemical group 0.000 description 47
• 238000005160 1H NMR spectroscopy Methods 0.000 description 45
• 230000002062 proliferating effect Effects 0.000 description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
• KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 36
• 230000002829 reductive effect Effects 0.000 description 33
• 239000002904 solvent Substances 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• 238000010898 silica gel chromatography Methods 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 25
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 230000003902 lesion Effects 0.000 description 24
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 150000001721 carbon Chemical group 0.000 description 23
• 125000005843 halogen group Chemical group 0.000 description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• 125000002947 alkylene group Chemical group 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 19
• 239000007832 Na2SO4 Substances 0.000 description 19
• 238000006243 chemical reaction Methods 0.000 description 19
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 19
• 238000011282 treatment Methods 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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• 125000004122 cyclic group Chemical group 0.000 description 15
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• 150000003254 radicals Chemical group 0.000 description 14
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
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