TW202003524A - 噻吩并嘧啶酮化合物 - Google Patents

Info

Publication number

TW202003524A

TW202003524A TW108111421A TW108111421A TW202003524A TW 202003524 A TW202003524 A TW 202003524A TW 108111421 A TW108111421 A TW 108111421A TW 108111421 A TW108111421 A TW 108111421A TW 202003524 A TW202003524 A TW 202003524A

Authority

TW

Taiwan

Prior art keywords

unsubstituted

substituted

group

compound

alkyl

Prior art date

2018-03-30

Links

• Espacenet
• Global Dossier
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• GFZLEUSLQORNJJ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine 5-oxide Chemical class C1=NC=C2S(=O)C=CC2=N1 GFZLEUSLQORNJJ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 397
• 239000000203 mixture Substances 0.000 claims abstract description 76
• 238000000034 method Methods 0.000 claims abstract description 73
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 56
• 201000010099 disease Diseases 0.000 claims abstract description 33
• 108090000623 proteins and genes Proteins 0.000 claims abstract description 30
• 102000004169 proteins and genes Human genes 0.000 claims abstract description 27
• 208000035475 disorder Diseases 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims description 119
• 229910052739 hydrogen Inorganic materials 0.000 claims description 106
• 239000001257 hydrogen Substances 0.000 claims description 106
• 125000000623 heterocyclic group Chemical group 0.000 claims description 80
• -1 N-morpholinyl Chemical group 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• 229910052736 halogen Inorganic materials 0.000 claims description 61
• 150000002367 halogens Chemical class 0.000 claims description 61
• 150000002431 hydrogen Chemical class 0.000 claims description 54
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 47
• 229910052805 deuterium Inorganic materials 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 239000008194 pharmaceutical composition Substances 0.000 claims description 42
• 150000001412 amines Chemical class 0.000 claims description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 102000004127 Cytokines Human genes 0.000 claims description 31
• 108090000695 Cytokines Proteins 0.000 claims description 31
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 29
• 102100036816 Eukaryotic peptide chain release factor GTP-binding subunit ERF3A Human genes 0.000 claims description 27
• 101000851788 Homo sapiens Eukaryotic peptide chain release factor GTP-binding subunit ERF3A Proteins 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 24
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000003277 amino group Chemical group 0.000 claims description 22
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• 101000599042 Homo sapiens Zinc finger protein Aiolos Proteins 0.000 claims description 19
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• 102100034357 Casein kinase I isoform alpha Human genes 0.000 claims description 18
• 101000994700 Homo sapiens Casein kinase I isoform alpha Proteins 0.000 claims description 18
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• 101000599037 Homo sapiens Zinc finger protein Helios Proteins 0.000 claims description 13
• 102100037796 Zinc finger protein Helios Human genes 0.000 claims description 13
• 208000032839 leukemia Diseases 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 13
• 150000002148 esters Chemical class 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
• 108010013958 Ikaros Transcription Factor Proteins 0.000 claims description 11
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• 239000004202 carbamide Substances 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 11
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
• 101100351286 Dictyostelium discoideum pdeE gene Proteins 0.000 claims description 10
• 101150037969 pde-6 gene Proteins 0.000 claims description 10
• 125000004193 piperazinyl group Chemical group 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 150000003672 ureas Chemical class 0.000 claims description 9
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
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• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
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• 125000001544 thienyl group Chemical group 0.000 claims description 4
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• 210000001130 astrocyte Anatomy 0.000 claims description 3
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000003725 azepanyl group Chemical group 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
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• 239000000243 solution Substances 0.000 description 52
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 48
• 125000004429 atom Chemical group 0.000 description 43
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
• 125000004432 carbon atom Chemical group C* 0.000 description 36
• 239000007787 solid Substances 0.000 description 36
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
• 239000002585 base Substances 0.000 description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
• 239000012074 organic phase Substances 0.000 description 27
• 125000005842 heteroatom Chemical group 0.000 description 26
• 235000018102 proteins Nutrition 0.000 description 25
• 125000003342 alkenyl group Chemical group 0.000 description 24
• 125000000304 alkynyl group Chemical group 0.000 description 23
• 125000000392 cycloalkenyl group Chemical group 0.000 description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
• 229910052799 carbon Inorganic materials 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
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• 229910002027 silica gel Inorganic materials 0.000 description 15
• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 15
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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 14
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• KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 11
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