IL302595A

IL302595A - Servalon ligands and bifunctional compounds containing them

Servalon ligands and bifunctional compounds containing them

Info

Publication number: IL302595A
Authority: IL; Israel
Prior art keywords: pct; syndrome; group; optionally substituted; alkyl
Prior art date: 2018-04-13

Application number

IL302595A

Other languages

English (en)

Hebrew (he)

Original Assignee

Arvinas Operations Inc

Priority date

2018-04-13

Filing date

2019-04-09

Publication date

2023-07-01

2018-04-13 Priority claimed from US15/953,108 external-priority patent/US20180228907A1/en

2019-04-09 Application filed by Arvinas Operations Inc filed Critical Arvinas Operations Inc

2023-07-01 Publication of IL302595A publication Critical patent/IL302595A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 234
230000001588 bifunctional effect Effects 0.000 title claims description 43
102100032783 Protein cereblon Human genes 0.000 title claims description 37
101000941994 Homo sapiens Protein cereblon Proteins 0.000 title claims description 28
239000003446 ligand Substances 0.000 title description 18
125000005647 linker group Chemical group 0.000 claims description 208
108090000623 proteins and genes Proteins 0.000 claims description 187
102000004169 proteins and genes Human genes 0.000 claims description 186
125000003118 aryl group Chemical group 0.000 claims description 167
-1 -C(=O)R Chemical group 0.000 claims description 144
125000000217 alkyl group Chemical group 0.000 claims description 138
125000005843 halogen group Chemical group 0.000 claims description 99
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 92
229910052736 halogen Inorganic materials 0.000 claims description 86
229910052799 carbon Inorganic materials 0.000 claims description 78
230000027455 binding Effects 0.000 claims description 77
125000001072 heteroaryl group Chemical group 0.000 claims description 75
150000002367 halogens Chemical class 0.000 claims description 74
125000000623 heterocyclic group Chemical group 0.000 claims description 73
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 71
229910052760 oxygen Inorganic materials 0.000 claims description 70
239000000203 mixture Substances 0.000 claims description 69
229910052739 hydrogen Inorganic materials 0.000 claims description 68
239000000126 substance Substances 0.000 claims description 63
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
102000006275 Ubiquitin-Protein Ligases Human genes 0.000 claims description 59
108010083111 Ubiquitin-Protein Ligases Proteins 0.000 claims description 59
201000010099 disease Diseases 0.000 claims description 58
229910052757 nitrogen Inorganic materials 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 51
239000003112 inhibitor Substances 0.000 claims description 44
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
230000015556 catabolic process Effects 0.000 claims description 41
125000002619 bicyclic group Chemical group 0.000 claims description 40
125000000753 cycloalkyl group Chemical group 0.000 claims description 39
238000006731 degradation reaction Methods 0.000 claims description 39
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 37
238000000034 method Methods 0.000 claims description 37
230000008685 targeting Effects 0.000 claims description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
125000005842 heteroatom Chemical group 0.000 claims description 33
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 31
229910052717 sulfur Inorganic materials 0.000 claims description 29
125000004429 atom Chemical group 0.000 claims description 28
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206010028980 Neoplasm Diseases 0.000 claims description 26
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
150000003384 small molecules Chemical class 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
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238000006467 substitution reaction Methods 0.000 claims description 23
239000003795 chemical substances by application Substances 0.000 claims description 21
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210000004027 cell Anatomy 0.000 claims description 18
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
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239000002253 acid Substances 0.000 claims description 9
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RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 7
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
150000005347 biaryls Chemical group 0.000 claims description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
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125000000524 functional group Chemical group 0.000 claims description 7
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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 5
208000032839 leukemia Diseases 0.000 claims description 5
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