KR20220023343A - 단백질 표적 화합물, 이의 약학 조성물 및 이들의 치료적 적용 - Google Patents

Info

Publication number

KR20220023343A

KR20220023343A KR1020217039259A KR20217039259A KR20220023343A KR 20220023343 A KR20220023343 A KR 20220023343A KR 1020217039259 A KR1020217039259 A KR 1020217039259A KR 20217039259 A KR20217039259 A KR 20217039259A KR 20220023343 A KR20220023343 A KR 20220023343A

Authority

KR

South Korea

Prior art keywords

methyl

optionally substituted

dioxopiperidin

oxo

dihydro

Prior art date

2019-05-24

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.)

Withdrawn

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 287
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 18
• 230000001225 therapeutic effect Effects 0.000 title description 6
• 230000018883 protein targeting Effects 0.000 title 1
• 239000000203 mixture Substances 0.000 claims abstract description 167
• 238000000034 method Methods 0.000 claims abstract description 134
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 59
• 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 26
• -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 1106
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 206
• 125000000623 heterocyclic group Chemical group 0.000 claims description 157
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
• 125000003118 aryl group Chemical group 0.000 claims description 135
• 125000001424 substituent group Chemical group 0.000 claims description 119
• 150000003839 salts Chemical class 0.000 claims description 118
• 229910052736 halogen Inorganic materials 0.000 claims description 117
• 150000002367 halogens Chemical class 0.000 claims description 114
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 112
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 100
• 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 87
• 239000012453 solvate Substances 0.000 claims description 75
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 68
• 239000000651 prodrug Substances 0.000 claims description 68
• 229940002612 prodrug Drugs 0.000 claims description 68
• 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 68
• 229910052799 carbon Inorganic materials 0.000 claims description 67
• 229910052739 hydrogen Inorganic materials 0.000 claims description 64
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 62
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 61
• 125000001153 fluoro group Chemical group F* 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 51
• 125000001544 thienyl group Chemical group 0.000 claims description 51
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 50
• 125000004432 carbon atom Chemical group C* 0.000 claims description 50
• 229910052805 deuterium Inorganic materials 0.000 claims description 49
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 48
• 125000004076 pyridyl group Chemical group 0.000 claims description 48
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 47
• 125000001624 naphthyl group Chemical group 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
• 125000003386 piperidinyl group Chemical group 0.000 claims description 39
• 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 37
• 102000004127 Cytokines Human genes 0.000 claims description 35
• 108090000695 Cytokines Proteins 0.000 claims description 35
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 35
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 34
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 30
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 27
• 230000000155 isotopic effect Effects 0.000 claims description 27
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 26
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 239000004202 carbamide Substances 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
• 102100036816 Eukaryotic peptide chain release factor GTP-binding subunit ERF3A Human genes 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims description 18
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 18
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 18
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 18
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 18
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 18
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 18
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 18
• 101000851788 Homo sapiens Eukaryotic peptide chain release factor GTP-binding subunit ERF3A Proteins 0.000 claims description 18
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 17
• 230000000694 effects Effects 0.000 claims description 17
• PFNNFEGXYVOGCW-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O PFNNFEGXYVOGCW-UHFFFAOYSA-N 0.000 claims description 16
• 101000599042 Homo sapiens Zinc finger protein Aiolos Proteins 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 16
• 102100037798 Zinc finger protein Aiolos Human genes 0.000 claims description 16
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
• 108010002350 Interleukin-2 Proteins 0.000 claims description 15
• 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 15
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 15
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 13
• WPPIXWQHHLGVEU-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)=O WPPIXWQHHLGVEU-UHFFFAOYSA-N 0.000 claims description 12
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
• 125000004799 bromophenyl group Chemical group 0.000 claims description 12
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 12
• 125000004802 cyanophenyl group Chemical group 0.000 claims description 12
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 12
• 125000004212 difluorophenyl group Chemical group 0.000 claims description 12
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 12
• 125000003944 tolyl group Chemical group 0.000 claims description 12
• 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 12
• 102100034357 Casein kinase I isoform alpha Human genes 0.000 claims description 11
• 101000994700 Homo sapiens Casein kinase I isoform alpha Proteins 0.000 claims description 11
• SKAIDPMCBUKTDS-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O SKAIDPMCBUKTDS-UHFFFAOYSA-N 0.000 claims description 9
• PAJIVQURKVNBMV-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C=1SC(=CC=1)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C=1SC(=CC=1)C(C)C)=O)=O PAJIVQURKVNBMV-UHFFFAOYSA-N 0.000 claims description 9
• BVKXSQIIWVSQON-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)N(C)CC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)N(C)CC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O BVKXSQIIWVSQON-UHFFFAOYSA-N 0.000 claims description 8
• LSLCFJJBFINCBD-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC(=C1)F)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC(=C1)F)=O)C1C(NC(CC1)=O)=O)=O LSLCFJJBFINCBD-UHFFFAOYSA-N 0.000 claims description 8
• DPYQCNUXTFMZNG-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2C(N(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2C(N(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O)=O DPYQCNUXTFMZNG-UHFFFAOYSA-N 0.000 claims description 8
• RHTKICIFAWVVNQ-NRFANRHFSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)[C@@H]1C(NC(CCC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)[C@@H]1C(NC(CCC1)=O)=O)=O RHTKICIFAWVVNQ-NRFANRHFSA-N 0.000 claims description 8
• CXAJTVZNHRKSEI-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1C(N(C2=O)C1C(NC(CC1)=O)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1C(N(C2=O)C1C(NC(CC1)=O)=O)=O)=O CXAJTVZNHRKSEI-UHFFFAOYSA-N 0.000 claims description 8
• XQCZWLZNYYCFOF-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(F)F Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(F)F XQCZWLZNYYCFOF-UHFFFAOYSA-N 0.000 claims description 8
• WKJQMOSOFICGIW-UHFFFAOYSA-N C(C)(C)(C)C1CCN(CC1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1CCN(CC1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O WKJQMOSOFICGIW-UHFFFAOYSA-N 0.000 claims description 8
• IWVBPVNRRFZDDD-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O IWVBPVNRRFZDDD-UHFFFAOYSA-N 0.000 claims description 8
• UFSMCJVMRRSWCX-UHFFFAOYSA-N C(C)(CC)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(CC)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O UFSMCJVMRRSWCX-UHFFFAOYSA-N 0.000 claims description 8
• LIPURGANEFFIRN-UHFFFAOYSA-N C1(=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)C1=CC=CC=C1 LIPURGANEFFIRN-UHFFFAOYSA-N 0.000 claims description 8
• BGCKNJDQZQQJNX-UHFFFAOYSA-N C1(CC1)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C1(CC1)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O BGCKNJDQZQQJNX-UHFFFAOYSA-N 0.000 claims description 8
• ZVPPHZQPVATJDO-UHFFFAOYSA-N CC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O ZVPPHZQPVATJDO-UHFFFAOYSA-N 0.000 claims description 8
• WZZFZAMQEWZKEU-UHFFFAOYSA-N CC=1C=C(C=CC=1C(C)(C)C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC=1C=C(C=CC=1C(C)(C)C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O WZZFZAMQEWZKEU-UHFFFAOYSA-N 0.000 claims description 8
• IAOLSTUHNSRQSC-UHFFFAOYSA-N CN(C)CC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound CN(C)CC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O IAOLSTUHNSRQSC-UHFFFAOYSA-N 0.000 claims description 8
• LTXKQVLTXNVIOR-UHFFFAOYSA-N CN(C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)C Chemical compound CN(C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)C LTXKQVLTXNVIOR-UHFFFAOYSA-N 0.000 claims description 8
• KVJCAGXQPURVGY-UHFFFAOYSA-N COC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound COC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O KVJCAGXQPURVGY-UHFFFAOYSA-N 0.000 claims description 8
• QELHAYKSZNAQRO-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O QELHAYKSZNAQRO-UHFFFAOYSA-N 0.000 claims description 8
• ALWUJWXYMPAJJW-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)(F)F Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)(F)F ALWUJWXYMPAJJW-UHFFFAOYSA-N 0.000 claims description 8
• PAUNAGKNSMRHKY-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(F)F Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(F)F PAUNAGKNSMRHKY-UHFFFAOYSA-N 0.000 claims description 8
• YBUSUNMLGNPNGM-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O YBUSUNMLGNPNGM-UHFFFAOYSA-N 0.000 claims description 8
• OMKIJSATMJTWIZ-INIZCTEOSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)[C@@H]1C(NC(CCC1)=O)=O)(F)F Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)[C@@H]1C(NC(CCC1)=O)=O)(F)F OMKIJSATMJTWIZ-INIZCTEOSA-N 0.000 claims description 8
• KHLMHPAEWKSFCJ-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NCCCNCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)NCCCNCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 KHLMHPAEWKSFCJ-UHFFFAOYSA-N 0.000 claims description 8
• HUDJFDUNSFBSCP-UHFFFAOYSA-N FC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound FC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O HUDJFDUNSFBSCP-UHFFFAOYSA-N 0.000 claims description 8
• 101000599037 Homo sapiens Zinc finger protein Helios Proteins 0.000 claims description 8
• 108010013958 Ikaros Transcription Factor Proteins 0.000 claims description 8
• 102000017182 Ikaros Transcription Factor Human genes 0.000 claims description 8
• MPLPFEOGDMRRBG-UHFFFAOYSA-N O1CCN(CC1)CC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound O1CCN(CC1)CC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O MPLPFEOGDMRRBG-UHFFFAOYSA-N 0.000 claims description 8
• MUHAWBAOZSMGKD-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CCNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CCNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O MUHAWBAOZSMGKD-UHFFFAOYSA-N 0.000 claims description 8
• AHQIWKLPWIVQKS-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(CC1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(CC1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O AHQIWKLPWIVQKS-UHFFFAOYSA-N 0.000 claims description 8
• DHDVUZMKOCNDEG-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C=1SC=CC=1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C=1SC=CC=1)=O)=O DHDVUZMKOCNDEG-UHFFFAOYSA-N 0.000 claims description 8
• LYJSAMXIJXMTBR-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)(F)F)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)(F)F)=O)=O LYJSAMXIJXMTBR-UHFFFAOYSA-N 0.000 claims description 8
• CPDWPAVOHIMKOD-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)F)(F)F)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)F)(F)F)=O)=O CPDWPAVOHIMKOD-UHFFFAOYSA-N 0.000 claims description 8
• DFDFXGDKUPGLHY-UHFFFAOYSA-N OC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound OC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O DFDFXGDKUPGLHY-UHFFFAOYSA-N 0.000 claims description 8
• 102100037796 Zinc finger protein Helios Human genes 0.000 claims description 8
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• XXFVFFLPZKJPNN-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C1(=CC=CC=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O XXFVFFLPZKJPNN-UHFFFAOYSA-N 0.000 claims description 7
• 206010025323 Lymphomas Diseases 0.000 claims description 7
• WMYWVABMTRLUSP-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C(=C2C1)C)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C(=C2C1)C)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O WMYWVABMTRLUSP-UHFFFAOYSA-N 0.000 claims description 7
• ISFHFFKINJCNJC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O ISFHFFKINJCNJC-UHFFFAOYSA-N 0.000 claims description 7
• IMGFKGNBOZHWFE-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O IMGFKGNBOZHWFE-UHFFFAOYSA-N 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• OIHPYXYAPQPUOJ-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound C(#N)C1=CC=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 OIHPYXYAPQPUOJ-UHFFFAOYSA-N 0.000 claims description 6
• WVHACNLDQFOYIL-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)N(C)CC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)N(C)CC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O WVHACNLDQFOYIL-UHFFFAOYSA-N 0.000 claims description 6
• JQSWBQCKNFJNCT-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2C(N(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)=O JQSWBQCKNFJNCT-UHFFFAOYSA-N 0.000 claims description 6
• OZNQXMKOPQXMKV-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC(=C1F)F)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC(=C1F)F)=O)C1C(NC(CC1)=O)=O)=O OZNQXMKOPQXMKV-UHFFFAOYSA-N 0.000 claims description 6
• GPXZJXPALPJOFI-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1F)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1F)=O)C1C(NC(CC1)=O)=O)=O GPXZJXPALPJOFI-UHFFFAOYSA-N 0.000 claims description 6
• JFMSCKQYKFYENE-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=CSC=2C(N(CC=21)C1C(NC(CC1)=O)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=CSC=2C(N(CC=21)C1C(NC(CC1)=O)=O)=O)=O JFMSCKQYKFYENE-UHFFFAOYSA-N 0.000 claims description 6
• XRGJJLCQXBTOKW-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O XRGJJLCQXBTOKW-UHFFFAOYSA-N 0.000 claims description 6
• PQCUUUGLNKQCKC-UHFFFAOYSA-N C(C)(C)(C)C1CCC(CC1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1CCC(CC1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O PQCUUUGLNKQCKC-UHFFFAOYSA-N 0.000 claims description 6
• QDUVSIUYCFTAGD-UHFFFAOYSA-N C(C)(C)(C)C1CCC(CC1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1CCC(CC1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O QDUVSIUYCFTAGD-UHFFFAOYSA-N 0.000 claims description 6
• LUSKDOQGEYAWGW-UHFFFAOYSA-N C(C)(C)(C)C1CCN(CC1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1CCN(CC1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O LUSKDOQGEYAWGW-UHFFFAOYSA-N 0.000 claims description 6
• VIRUKUYIXAFWCJ-UHFFFAOYSA-N CC=1C=C(C=C(C=1)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC=1C=C(C=C(C=1)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O VIRUKUYIXAFWCJ-UHFFFAOYSA-N 0.000 claims description 6
• FOXBRESCJDTTON-UHFFFAOYSA-N CC=1C=C(C=CC=1C(C)(C)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC=1C=C(C=CC=1C(C)(C)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O FOXBRESCJDTTON-UHFFFAOYSA-N 0.000 claims description 6
• JPFISWAOWGGUPZ-UHFFFAOYSA-N CC=1C=C(C=CC=1C(C)(C)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC=1C=C(C=CC=1C(C)(C)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O JPFISWAOWGGUPZ-UHFFFAOYSA-N 0.000 claims description 6
• WRKBIBCBGKFSSJ-UHFFFAOYSA-N CN(C=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)C Chemical compound CN(C=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)C WRKBIBCBGKFSSJ-UHFFFAOYSA-N 0.000 claims description 6
• BJMNTHXVFZKNGI-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OC)OC)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound COC1=C(C(=CC(=C1)OC)OC)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O BJMNTHXVFZKNGI-UHFFFAOYSA-N 0.000 claims description 6
• FMPHHZIBUTXBNQ-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O FMPHHZIBUTXBNQ-UHFFFAOYSA-N 0.000 claims description 6
• 208000011231 Crohn disease Diseases 0.000 claims description 6
• 108090001005 Interleukin-6 Proteins 0.000 claims description 6
• ZUGCYSIJHSQPCP-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(C(CCC1=CC=CC=C1)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(C(CCC1=CC=CC=C1)=O)=O)=O)=O ZUGCYSIJHSQPCP-UHFFFAOYSA-N 0.000 claims description 6
• BURRWYKTOWWLOP-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C=1SC(=CC=1)C(C)C)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C=1SC(=CC=1)C(C)C)=O)=O)=O BURRWYKTOWWLOP-UHFFFAOYSA-N 0.000 claims description 6
• XFHDORKXQGMSOM-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1OC)OC)OC)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1OC)OC)OC)=O)=O)=O)=O XFHDORKXQGMSOM-UHFFFAOYSA-N 0.000 claims description 6
• KOPIYCJOIBQNAV-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=CC=C1)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=CC=C1)=O)=O)=O)=O KOPIYCJOIBQNAV-UHFFFAOYSA-N 0.000 claims description 6
• GUSQVMPOEZWTEN-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CCNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CCNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O GUSQVMPOEZWTEN-UHFFFAOYSA-N 0.000 claims description 6
• JWOWUUJKNZUZIC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(=O)C=1SC(=CC=1)C(C)C)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(=O)C=1SC(=CC=1)C(C)C)=O)=O)=O JWOWUUJKNZUZIC-UHFFFAOYSA-N 0.000 claims description 6
• JJUUWCAKTJXXLB-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=CC=C1)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=CC=C1)=O)=O)=O)=O JJUUWCAKTJXXLB-UHFFFAOYSA-N 0.000 claims description 6
• MACMVYAZBJFSDS-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)NC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)NC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O MACMVYAZBJFSDS-UHFFFAOYSA-N 0.000 claims description 6
• PHYOFMPDCYXSHP-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1=O)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)=O)=O)=O)=O PHYOFMPDCYXSHP-UHFFFAOYSA-N 0.000 claims description 6
• HQKLJWZIJWUKPV-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C1=CC=C(C=C1)C(CO)(C)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C1=CC=C(C=C1)C(CO)(C)C)=O)=O HQKLJWZIJWUKPV-UHFFFAOYSA-N 0.000 claims description 6
• DFPWNGHCMNGPKF-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C1=CC=C(C=C1)C1(CC1)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C1=CC=C(C=C1)C1(CC1)C)=O)=O DFPWNGHCMNGPKF-UHFFFAOYSA-N 0.000 claims description 6
• DQFNEFGHGPWADB-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C1=CC=C(C=C1)C1CCN(CC1)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(=O)C1=CC=C(C=C1)C1CCN(CC1)C)=O)=O DQFNEFGHGPWADB-UHFFFAOYSA-N 0.000 claims description 6
• QRGLRLSSUAKKPH-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)C(C(F)(F)F)C)=O)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C1=CC=C(C=C1)C(C(F)(F)F)C)=O)=O)=O QRGLRLSSUAKKPH-UHFFFAOYSA-N 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• IZHOMDVRFXFANG-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(#N)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O IZHOMDVRFXFANG-UHFFFAOYSA-N 0.000 claims description 5
• AZJJVERWIMWISW-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(#N)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O AZJJVERWIMWISW-UHFFFAOYSA-N 0.000 claims description 5
• NOUDYTLFBKARIU-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O NOUDYTLFBKARIU-UHFFFAOYSA-N 0.000 claims description 5
• UXDXKTBQSUIHAG-UHFFFAOYSA-N CC=1C=C(C=C(C=1)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC=1C=C(C=C(C=1)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O UXDXKTBQSUIHAG-UHFFFAOYSA-N 0.000 claims description 5
• FOVHMRHVXDDRIO-UHFFFAOYSA-N COC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound COC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O FOVHMRHVXDDRIO-UHFFFAOYSA-N 0.000 claims description 5
• CBTVQNVRJBQVAW-UHFFFAOYSA-N COC=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound COC=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O CBTVQNVRJBQVAW-UHFFFAOYSA-N 0.000 claims description 5
• KZGAYAPVHNWLIV-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O KZGAYAPVHNWLIV-UHFFFAOYSA-N 0.000 claims description 5
• MFMYQNQMMJEVKU-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O MFMYQNQMMJEVKU-UHFFFAOYSA-N 0.000 claims description 5
• DLVTYQUZACRFOL-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O DLVTYQUZACRFOL-UHFFFAOYSA-N 0.000 claims description 5
• WCVDIVXQEYIHRM-UHFFFAOYSA-N FC1=C(C=CC=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound FC1=C(C=CC=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O WCVDIVXQEYIHRM-UHFFFAOYSA-N 0.000 claims description 5
• GVTGWSROSMGQCU-UHFFFAOYSA-N FC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound FC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O GVTGWSROSMGQCU-UHFFFAOYSA-N 0.000 claims description 5
• SRGYCLYFUVVOKB-UHFFFAOYSA-N FC=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound FC=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O SRGYCLYFUVVOKB-UHFFFAOYSA-N 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• MLEZQJRHDMGGKJ-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC(=CC=C1)OC)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC(=CC=C1)OC)=O)=O)=O MLEZQJRHDMGGKJ-UHFFFAOYSA-N 0.000 claims description 5
• GOGKTIRTBGPOSG-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC2=CC=CC=C2C=C1)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC2=CC=CC=C2C=C1)=O)=O)=O GOGKTIRTBGPOSG-UHFFFAOYSA-N 0.000 claims description 5
• LJEVVTPSLHCDIR-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC=C(C=C1)OC)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC=C(C=C1)OC)=O)=O)=O LJEVVTPSLHCDIR-UHFFFAOYSA-N 0.000 claims description 5
• CCRFHBKXFLRZBR-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)F)=O)=O)=O)=O CCRFHBKXFLRZBR-UHFFFAOYSA-N 0.000 claims description 5
• SINPUUWRHUGTDN-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O)=O SINPUUWRHUGTDN-UHFFFAOYSA-N 0.000 claims description 5
• USICULGPBMJZIE-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(=O)C1=CC2=CC=CC=C2C=C1)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(=O)C1=CC2=CC=CC=C2C=C1)=O)=O)=O USICULGPBMJZIE-UHFFFAOYSA-N 0.000 claims description 5
• YFIBMHNUILIQLM-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C)=O)=O)=O)=O YFIBMHNUILIQLM-UHFFFAOYSA-N 0.000 claims description 5
• NEPRFTJONIMWIR-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C1CCNCC1)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C1CCNCC1)=O)=O)=O)=O NEPRFTJONIMWIR-UHFFFAOYSA-N 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 206010017758 gastric cancer Diseases 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 230000002757 inflammatory effect Effects 0.000 claims description 5
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 230000004952 protein activity Effects 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 201000011549 stomach cancer Diseases 0.000 claims description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• UFFDPDWGCMIFOF-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-3-[[5-(2,6-dioxopiperidin-3-yl)-6-oxo-4H-thieno[2,3-c]pyrrol-3-yl]methyl]urea Chemical compound Cc1ccc(NC(=O)NCc2csc3C(=O)N(Cc23)C2CCC(=O)NC2=O)cc1Cl UFFDPDWGCMIFOF-UHFFFAOYSA-N 0.000 claims description 4
• UIJJBTOFEJMPCM-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-3-[[5-(2,6-dioxopiperidin-3-yl)-6-oxo-4H-thieno[3,4-c]pyrrol-3-yl]methyl]urea Chemical compound ClC=1C=C(C=CC=1C)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O UIJJBTOFEJMPCM-UHFFFAOYSA-N 0.000 claims description 4
• TXLKKMMVDLDQDP-HNNXBMFYSA-N 1-(3-chloro-4-methylphenyl)-3-[[5-[(3S)-2,6-dioxopiperidin-3-yl]-6-oxo-4H-thieno[2,3-c]pyrrol-2-yl]methyl]urea Chemical compound Cc1ccc(NC(=O)NCc2cc3CN([C@H]4CCC(=O)NC4=O)C(=O)c3s2)cc1Cl TXLKKMMVDLDQDP-HNNXBMFYSA-N 0.000 claims description 4
• CEFKGGORCVBVRM-INIZCTEOSA-N 1-(3-chloro-4-methylphenyl)-3-[[5-[(3S)-2,7-dioxoazepan-3-yl]-6-oxo-4H-thieno[3,4-c]pyrrol-3-yl]methyl]urea Chemical compound ClC=1C=C(C=CC=1C)NC(=O)NCC=1SC=C2C=1CN(C2=O)[C@@H]1C(NC(CCC1)=O)=O CEFKGGORCVBVRM-INIZCTEOSA-N 0.000 claims description 4
• FFLWUKAFZLMUBS-UHFFFAOYSA-N 2-(3-chloro-4-methylphenyl)-N-[[5-(2,6-dioxopiperidin-3-yl)-6-oxo-4H-thieno[3,4-c]pyrrol-3-yl]methyl]prop-2-enamide Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=C FFLWUKAFZLMUBS-UHFFFAOYSA-N 0.000 claims description 4
• XLVWREQKVGGIFW-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-N-[[5-(2,6-dioxopiperidin-3-yl)-6-oxo-4H-thieno[3,4-c]pyrrol-3-yl]methyl]prop-2-enamide Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=C XLVWREQKVGGIFW-UHFFFAOYSA-N 0.000 claims description 4
• IFGJXCUUPBJHBG-UHFFFAOYSA-N 3-(3-chloro-4-methylphenyl)-N-[[5-(2,6-dioxopiperidin-3-yl)-6-oxo-4H-thieno[2,3-c]pyrrol-2-yl]methyl]prop-2-enamide Chemical compound ClC=1C=C(C=CC=1C)C=CC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 IFGJXCUUPBJHBG-UHFFFAOYSA-N 0.000 claims description 4
• QNCIKOMRKIZXHX-UHFFFAOYSA-N 3-(3-chloro-4-methylphenyl)-N-[[5-(2,6-dioxopiperidin-3-yl)-6-oxo-4H-thieno[3,4-c]pyrrol-3-yl]methyl]prop-2-enamide Chemical compound ClC=1C=C(C=CC=1C)C=CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O QNCIKOMRKIZXHX-UHFFFAOYSA-N 0.000 claims description 4
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
• YTQATEBNMIYWFU-UHFFFAOYSA-N BrC1=CC(=C(C=C1)S(=O)(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)OC(F)(F)F Chemical compound BrC1=CC(=C(C=C1)S(=O)(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)OC(F)(F)F YTQATEBNMIYWFU-UHFFFAOYSA-N 0.000 claims description 4
• UKBXJAQKNSWZRL-UHFFFAOYSA-N BrC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound BrC1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O UKBXJAQKNSWZRL-UHFFFAOYSA-N 0.000 claims description 4
• ZRTJMRDISQUPOW-UHFFFAOYSA-N C(#N)C=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound C(#N)C=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 ZRTJMRDISQUPOW-UHFFFAOYSA-N 0.000 claims description 4
• OSUVBYJMZAPARD-UHFFFAOYSA-N C(C)(C)(C)C1=CC(=C(C(=C1)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)C Chemical compound C(C)(C)(C)C1=CC(=C(C(=C1)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O)C OSUVBYJMZAPARD-UHFFFAOYSA-N 0.000 claims description 4
• KTEASOLVRBIIJR-UHFFFAOYSA-N C(C)(C)(C)C1=CC(=C(C(=C1)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O)C Chemical compound C(C)(C)(C)C1=CC(=C(C(=C1)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O)C KTEASOLVRBIIJR-UHFFFAOYSA-N 0.000 claims description 4
• MEPJDUQOXVVZRX-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(C(F)(F)F)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(C(F)(F)F)O MEPJDUQOXVVZRX-UHFFFAOYSA-N 0.000 claims description 4
• LZHHWNKSJAJCPO-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C(C)C Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C(C)C LZHHWNKSJAJCPO-UHFFFAOYSA-N 0.000 claims description 4
• FEECUXGCIWNJMU-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C(F)(F)F Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C(F)(F)F FEECUXGCIWNJMU-UHFFFAOYSA-N 0.000 claims description 4
• YSAXPWCWPWJKSU-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)O YSAXPWCWPWJKSU-UHFFFAOYSA-N 0.000 claims description 4
• KVAFBJBHUJELLW-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O KVAFBJBHUJELLW-UHFFFAOYSA-N 0.000 claims description 4
• KKDVIHDKRWELRE-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)CCC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound C(C)(C)(C)C1=CC=C(C=C1)CCC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C KKDVIHDKRWELRE-UHFFFAOYSA-N 0.000 claims description 4
• ACTVGVBMIFQPNG-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O ACTVGVBMIFQPNG-UHFFFAOYSA-N 0.000 claims description 4
• QDKNPWLADHJRQG-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)CS(=O)(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)CS(=O)(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O QDKNPWLADHJRQG-UHFFFAOYSA-N 0.000 claims description 4
• MOLQFGJNEKCRNI-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O MOLQFGJNEKCRNI-UHFFFAOYSA-N 0.000 claims description 4
• IIINYXIVIFODGV-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NCCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NCCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O IIINYXIVIFODGV-UHFFFAOYSA-N 0.000 claims description 4
• IIUDZQKWMOPKJQ-UHFFFAOYSA-N C(C)N(C1=C(C=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C)CC Chemical compound C(C)N(C1=C(C=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C)CC IIUDZQKWMOPKJQ-UHFFFAOYSA-N 0.000 claims description 4
• JTHJQINRUMQMLD-UHFFFAOYSA-N C(C)N(C=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)CC Chemical compound C(C)N(C=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)CC JTHJQINRUMQMLD-UHFFFAOYSA-N 0.000 claims description 4
• DMTPPFMMZVZSHS-UHFFFAOYSA-N C(C)N(C=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)CC Chemical compound C(C)N(C=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)CC DMTPPFMMZVZSHS-UHFFFAOYSA-N 0.000 claims description 4
• XBXSCNCVDFVQQP-UHFFFAOYSA-N C(C)N(C=1C=C(C=CC=1F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)CC Chemical compound C(C)N(C=1C=C(C=CC=1F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)CC XBXSCNCVDFVQQP-UHFFFAOYSA-N 0.000 claims description 4
• UHLIAYLRNOYFCX-UHFFFAOYSA-N C1(=CC=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C1=CC=CC=C1 UHLIAYLRNOYFCX-UHFFFAOYSA-N 0.000 claims description 4
• KLEHGMYLWLWZCR-UHFFFAOYSA-N CC1=C(C(=CC(=C1)C)C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound CC1=C(C(=CC(=C1)C)C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 KLEHGMYLWLWZCR-UHFFFAOYSA-N 0.000 claims description 4
• NRNBURBKTFETBC-UHFFFAOYSA-N CN(C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=C(C=CC=C1)F)C Chemical compound CN(C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=C(C=CC=C1)F)C NRNBURBKTFETBC-UHFFFAOYSA-N 0.000 claims description 4
• FTWZMIVYVBLCAM-UHFFFAOYSA-N CN(C)CC=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound CN(C)CC=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 FTWZMIVYVBLCAM-UHFFFAOYSA-N 0.000 claims description 4
• YOKDXMQKSYUZAN-UHFFFAOYSA-N CN(C)CC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound CN(C)CC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 YOKDXMQKSYUZAN-UHFFFAOYSA-N 0.000 claims description 4
• BMMPZUWSQKJAQI-UHFFFAOYSA-N CN(C1=C(C=C(C=C1)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C)C Chemical compound CN(C1=C(C=C(C=C1)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C)C BMMPZUWSQKJAQI-UHFFFAOYSA-N 0.000 claims description 4
• QZUSUVRKEIFAEC-UHFFFAOYSA-N CN(C1=C(C=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C)C Chemical compound CN(C1=C(C=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C)C QZUSUVRKEIFAEC-UHFFFAOYSA-N 0.000 claims description 4
• HHIBTQAXOBDCGD-UHFFFAOYSA-N CN(C1=CC=C(C=C1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound CN(C1=CC=C(C=C1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C HHIBTQAXOBDCGD-UHFFFAOYSA-N 0.000 claims description 4
• DDFIXAUTTYUVDI-UHFFFAOYSA-N CN(C1=CC=C(C=C1)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound CN(C1=CC=C(C=C1)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C DDFIXAUTTYUVDI-UHFFFAOYSA-N 0.000 claims description 4
• KHJGXCPTUBDVAH-UHFFFAOYSA-N CN(C=1C=C(C=C(C=1)C(C)C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=C(C=1)C(C)C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C KHJGXCPTUBDVAH-UHFFFAOYSA-N 0.000 claims description 4
• FTKDUSOXBZLDIK-UHFFFAOYSA-N CN(C=1C=C(C=C(C=1)C(F)(F)F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=C(C=1)C(F)(F)F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C FTKDUSOXBZLDIK-UHFFFAOYSA-N 0.000 claims description 4
• AWAAUICSXKVOKY-UHFFFAOYSA-N CN(C=1C=C(C=C(C=1)C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=C(C=1)C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C AWAAUICSXKVOKY-UHFFFAOYSA-N 0.000 claims description 4
• SWAXGSPWXZCEJG-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=CC=1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C SWAXGSPWXZCEJG-UHFFFAOYSA-N 0.000 claims description 4
• BYNCINMJMIOVST-UHFFFAOYSA-N CN(C=1C=C(C=CC=1C(F)(F)F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=CC=1C(F)(F)F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C BYNCINMJMIOVST-UHFFFAOYSA-N 0.000 claims description 4
• HLILXSFTQDIYAC-UHFFFAOYSA-N CN(C=1C=C(C=CC=1C)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound CN(C=1C=C(C=CC=1C)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C HLILXSFTQDIYAC-UHFFFAOYSA-N 0.000 claims description 4
• HJUJZDGYQLBHSD-UHFFFAOYSA-N CN(C=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C HJUJZDGYQLBHSD-UHFFFAOYSA-N 0.000 claims description 4
• VIOJKTPDIFOTBJ-UHFFFAOYSA-N CN(C=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2=O)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2=O)C2C(NC(CC2)=O)=O)=O)S1)C VIOJKTPDIFOTBJ-UHFFFAOYSA-N 0.000 claims description 4
• JIWVGBCLBPOLDS-UHFFFAOYSA-N CN(C=1C=C(C=CC=1C)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound CN(C=1C=C(C=CC=1C)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C JIWVGBCLBPOLDS-UHFFFAOYSA-N 0.000 claims description 4
• VLHIHMNXBJFWJL-UHFFFAOYSA-N CN(C=1C=C(C=CC=1CC)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=CC=1CC)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C VLHIHMNXBJFWJL-UHFFFAOYSA-N 0.000 claims description 4
• UMXFWZSBAPECFM-UHFFFAOYSA-N CN(C=1C=C(C=CC=1F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN(C=1C=C(C=CC=1F)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C UMXFWZSBAPECFM-UHFFFAOYSA-N 0.000 claims description 4
• BNDJREDUWODZCL-UHFFFAOYSA-N CN(CCOC1=CC=C(C=C1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound CN(CCOC1=CC=C(C=C1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C BNDJREDUWODZCL-UHFFFAOYSA-N 0.000 claims description 4
• SJRYQWCHWXJFQL-UHFFFAOYSA-N CN(CCOC=1C=C(C=CC=1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound CN(CCOC=1C=C(C=CC=1)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C SJRYQWCHWXJFQL-UHFFFAOYSA-N 0.000 claims description 4
• BWYZHKQMHFWUDO-UHFFFAOYSA-N CN1N=C(C=C1NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C Chemical compound CN1N=C(C=C1NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C BWYZHKQMHFWUDO-UHFFFAOYSA-N 0.000 claims description 4
• ZDPUQJJPAWNPTN-UHFFFAOYSA-N COC=1C=C(C=C(C=1)OC)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound COC=1C=C(C=C(C=1)OC)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 ZDPUQJJPAWNPTN-UHFFFAOYSA-N 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• FYKHBPMKSOGWGB-UHFFFAOYSA-N ClC1=C(C=C(C=C1)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)OC(F)(F)F Chemical compound ClC1=C(C=C(C=C1)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)OC(F)(F)F FYKHBPMKSOGWGB-UHFFFAOYSA-N 0.000 claims description 4
• NRPIGVKGHITDQC-UHFFFAOYSA-N ClC1=C(C=CC(=C1)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)NC(C)=O Chemical compound ClC1=C(C=CC(=C1)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)NC(C)=O NRPIGVKGHITDQC-UHFFFAOYSA-N 0.000 claims description 4
• YRNXKCVKHVOATE-UHFFFAOYSA-N ClC1=CC(=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C(F)(F)F Chemical compound ClC1=CC(=C(C=C1)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1)C(F)(F)F YRNXKCVKHVOATE-UHFFFAOYSA-N 0.000 claims description 4
• BIXFRSFLBMVFQL-UHFFFAOYSA-N ClC1=CC(=C(S1)C(=O)OC)S(NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(=O)=O Chemical compound ClC1=CC(=C(S1)C(=O)OC)S(NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(=O)=O BIXFRSFLBMVFQL-UHFFFAOYSA-N 0.000 claims description 4
• JGBKYFRRDHAKSQ-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)C(F)(F)F)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=C(C=1)C(F)(F)F)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O JGBKYFRRDHAKSQ-UHFFFAOYSA-N 0.000 claims description 4
• BRNHYRPSKQYXLV-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C(C)C Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C(C)C BRNHYRPSKQYXLV-UHFFFAOYSA-N 0.000 claims description 4
• DEDZAVASXGLUFY-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)CC Chemical compound ClC=1C=C(C=CC=1C)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)CC DEDZAVASXGLUFY-UHFFFAOYSA-N 0.000 claims description 4
• NQMXBUNVIOPFJY-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)CC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 NQMXBUNVIOPFJY-UHFFFAOYSA-N 0.000 claims description 4
• GWOMICAPBBQISL-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CC(=O)NCC1=CC2=C(CN(C2=O)C2C(NC(CC2)=O)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)CC(=O)NCC1=CC2=C(CN(C2=O)C2C(NC(CC2)=O)=O)S1 GWOMICAPBBQISL-UHFFFAOYSA-N 0.000 claims description 4
• FHLLARLQDGSGLR-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CC(=O)NCC1=CSC=2C(N(CC=21)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1C)CC(=O)NCC1=CSC=2C(N(CC=21)C1C(NC(CC1)=O)=O)=O FHLLARLQDGSGLR-UHFFFAOYSA-N 0.000 claims description 4
• YHTGZDAIUHSJLF-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)CC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O YHTGZDAIUHSJLF-UHFFFAOYSA-N 0.000 claims description 4
• CRFBUBNHDMGGRW-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CCC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound ClC=1C=C(C=CC=1C)CCC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C CRFBUBNHDMGGRW-UHFFFAOYSA-N 0.000 claims description 4
• YRYBURVQYPKZCE-IBGZPJMESA-N ClC=1C=C(C=CC=1C)CCC(C(=O)NCC=1SC=C2C=1CN(C2=O)[C@@H]1C(NC(CC1)=O)=O)(C)C Chemical compound ClC=1C=C(C=CC=1C)CCC(C(=O)NCC=1SC=C2C=1CN(C2=O)[C@@H]1C(NC(CC1)=O)=O)(C)C YRYBURVQYPKZCE-IBGZPJMESA-N 0.000 claims description 4
• AQLXWQZNIMCEFR-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)CCCC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O AQLXWQZNIMCEFR-UHFFFAOYSA-N 0.000 claims description 4
• LEXFVTQJMYHQQB-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)CS(=O)(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)CS(=O)(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O LEXFVTQJMYHQQB-UHFFFAOYSA-N 0.000 claims description 4
• GHFIEIPMKBNJIH-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)N(C(=O)N(C)CC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound ClC=1C=C(C=CC=1C)N(C(=O)N(C)CC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C GHFIEIPMKBNJIH-UHFFFAOYSA-N 0.000 claims description 4
• FHKZANCAEZGHMM-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)N(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C Chemical compound ClC=1C=C(C=CC=1C)N(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C FHKZANCAEZGHMM-UHFFFAOYSA-N 0.000 claims description 4
• TYXJDSBVODFMSD-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2(C(NC(CC2)=O)=O)C)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2(C(NC(CC2)=O)=O)C)=O)S1 TYXJDSBVODFMSD-UHFFFAOYSA-N 0.000 claims description 4
• HEWMZLJFLXHRNK-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(C2)=O)=O)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(C(N(C2)C2C(NC(C2)=O)=O)=O)S1 HEWMZLJFLXHRNK-UHFFFAOYSA-N 0.000 claims description 4
• JEFJBMMGRIUBSD-INIZCTEOSA-N ClC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(CN(C2=O)[C@@H]2C(NC(CCC2)=O)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)NC(=O)NCC1=CC2=C(CN(C2=O)[C@@H]2C(NC(CCC2)=O)=O)S1 JEFJBMMGRIUBSD-INIZCTEOSA-N 0.000 claims description 4
• NXGUNLDDTUOTEH-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NC(=O)NCCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)NC(=O)NCCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O NXGUNLDDTUOTEH-UHFFFAOYSA-N 0.000 claims description 4
• GVGPSAZEVNKCFZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NC(=S)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound ClC=1C=C(C=CC=1C)NC(=S)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 GVGPSAZEVNKCFZ-UHFFFAOYSA-N 0.000 claims description 4
• WNOANKJQBXICSM-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NCCCCCNCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)NCCCCCNCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O WNOANKJQBXICSM-UHFFFAOYSA-N 0.000 claims description 4
• UIEAGNUSCSFYRB-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)NCCCNCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)NCCCNCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O UIEAGNUSCSFYRB-UHFFFAOYSA-N 0.000 claims description 4
• HFZXYDHDAKDVCZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1C)S(=O)(=O)NCC1=C2CN(C(C2=CS1)=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1C)S(=O)(=O)NCC1=C2CN(C(C2=CS1)=O)C1C(NC(CC1)=O)=O HFZXYDHDAKDVCZ-UHFFFAOYSA-N 0.000 claims description 4
• QAWCJXNZMQSLSY-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1Cl)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O QAWCJXNZMQSLSY-UHFFFAOYSA-N 0.000 claims description 4
• VZHNNUARAXFYFM-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1Cl)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O VZHNNUARAXFYFM-UHFFFAOYSA-N 0.000 claims description 4
• VSKSCKACNLNBKJ-UHFFFAOYSA-N ClC=1C=C(C=CC=1N(C)C)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1N(C)C)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O VSKSCKACNLNBKJ-UHFFFAOYSA-N 0.000 claims description 4
• MOCQOGVGGKTBFO-UHFFFAOYSA-N ClC=1C=C(C=CC=1OC)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound ClC=1C=C(C=CC=1OC)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O MOCQOGVGGKTBFO-UHFFFAOYSA-N 0.000 claims description 4
• LFLZYNXDPAIDKA-UHFFFAOYSA-N ClC=1C=C(CNC(=O)NCC2=CC3=C(CN(C3=O)C3C(NC(CC3)=O)=O)S2)C=CC=1C Chemical compound ClC=1C=C(CNC(=O)NCC2=CC3=C(CN(C3=O)C3C(NC(CC3)=O)=O)S2)C=CC=1C LFLZYNXDPAIDKA-UHFFFAOYSA-N 0.000 claims description 4
• VRIHFQDREHUJDM-KRWDZBQOSA-N ClC=1C=C(CNC(=O)NCC2=CC3=C(CN(C3=O)[C@@H]3C(NC(CCC3)=O)=O)S2)C=CC=1C Chemical compound ClC=1C=C(CNC(=O)NCC2=CC3=C(CN(C3=O)[C@@H]3C(NC(CCC3)=O)=O)S2)C=CC=1C VRIHFQDREHUJDM-KRWDZBQOSA-N 0.000 claims description 4
• KJLDZRFVVJDNPP-UHFFFAOYSA-N ClC=1C=C(CNC(=O)NCC2=CSC=3C(N(CC=32)C2C(NC(CC2)=O)=O)=O)C=CC=1C Chemical compound ClC=1C=C(CNC(=O)NCC2=CSC=3C(N(CC=32)C2C(NC(CC2)=O)=O)=O)C=CC=1C KJLDZRFVVJDNPP-UHFFFAOYSA-N 0.000 claims description 4
• HMHATYJYOYTEAP-UHFFFAOYSA-N ClC=1C=C(CNC(=O)NCCC=2SC=C3C=2CN(C3=O)C2C(NC(CC2)=O)=O)C=CC=1C Chemical compound ClC=1C=C(CNC(=O)NCCC=2SC=C3C=2CN(C3=O)C2C(NC(CC2)=O)=O)C=CC=1C HMHATYJYOYTEAP-UHFFFAOYSA-N 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• VCIOPCQUZXMKRJ-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)C(F)(F)F)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(F)F Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)NC(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)(F)F VCIOPCQUZXMKRJ-UHFFFAOYSA-N 0.000 claims description 4
• 208000001640 Fibromyalgia Diseases 0.000 claims description 4
• 206010018341 Gliosis Diseases 0.000 claims description 4
• 208000019693 Lung disease Diseases 0.000 claims description 4
• VIMSOGAMCOCLSY-UHFFFAOYSA-N NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC(=CC=C1)Cl Chemical compound NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC(=CC=C1)Cl VIMSOGAMCOCLSY-UHFFFAOYSA-N 0.000 claims description 4
• GMWRGTIKYDIBDY-UHFFFAOYSA-N NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC=C(C=C1)C Chemical compound NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC=C(C=C1)C GMWRGTIKYDIBDY-UHFFFAOYSA-N 0.000 claims description 4
• DZDLXPMOTAUWCO-UHFFFAOYSA-N NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC=C(C=C1)O Chemical compound NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC=C(C=C1)O DZDLXPMOTAUWCO-UHFFFAOYSA-N 0.000 claims description 4
• UCYNTHDYBAEGRI-UHFFFAOYSA-N NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC=C(C=C1)OCCC Chemical compound NC(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)C1=CC=C(C=C1)OCCC UCYNTHDYBAEGRI-UHFFFAOYSA-N 0.000 claims description 4
• XFWVKNHWPJNLSY-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)C(C)C)=O)=O XFWVKNHWPJNLSY-UHFFFAOYSA-N 0.000 claims description 4
• SJGUEWMXZPKSNC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)N(C)CC)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)N(C)CC)=O)=O SJGUEWMXZPKSNC-UHFFFAOYSA-N 0.000 claims description 4
• QGOPMCCSVPPWMK-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)N1CCCC1)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)N1CCCC1)=O)=O QGOPMCCSVPPWMK-UHFFFAOYSA-N 0.000 claims description 4
• LWVFMEUDDUOOHC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)O)=O)=O LWVFMEUDDUOOHC-UHFFFAOYSA-N 0.000 claims description 4
• QKULCEGSGGOLBC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)OC)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)C)OC)=O)=O QKULCEGSGGOLBC-UHFFFAOYSA-N 0.000 claims description 4
• SNTHMKSVTFDWQB-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)N1CCCC1)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)N1CCCC1)C)=O)=O SNTHMKSVTFDWQB-UHFFFAOYSA-N 0.000 claims description 4
• JVLLXWSSJQXRDU-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)N1CCOCC1)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=C(C=C1)N1CCOCC1)C)=O)=O JVLLXWSSJQXRDU-UHFFFAOYSA-N 0.000 claims description 4
• KTSBBTPYLQYWFB-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=CC=C1)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=CC=C1)C(C)C)=O)=O KTSBBTPYLQYWFB-UHFFFAOYSA-N 0.000 claims description 4
• JKVXJWFPQVVBQZ-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=CC=C1)N(C)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=CC=C1)N(C)C(C)C)=O)=O JKVXJWFPQVVBQZ-UHFFFAOYSA-N 0.000 claims description 4
• UAGRPUPDJULDKI-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=CC=C1)N1CCCC1)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC(=CC=C1)N1CCCC1)=O)=O UAGRPUPDJULDKI-UHFFFAOYSA-N 0.000 claims description 4
• CDPUNGDTCGUTLK-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC=C(C=C1)OC)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC=C(C=C1)OC)=O)=O CDPUNGDTCGUTLK-UHFFFAOYSA-N 0.000 claims description 4
• BVVXWXCTQRKVEC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC=CC2=CC=CC=C12)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC1=CC=CC2=CC=CC=C12)=O)=O BVVXWXCTQRKVEC-UHFFFAOYSA-N 0.000 claims description 4
• MJYLLCACEMSLMC-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC=1C=NC(=CC=1)N1CCOCC1)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)NC=1C=NC(=CC=1)N1CCOCC1)=O)=O MJYLLCACEMSLMC-UHFFFAOYSA-N 0.000 claims description 4
• ZJPDZUXZXHLERR-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=S)NC1=CC=CC=C1)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=S)NC1=CC=CC=C1)=O)=O ZJPDZUXZXHLERR-UHFFFAOYSA-N 0.000 claims description 4
• MEFWZJUZYGNHEU-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=S)NCCC1=CC=CC=C1)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=S)NCCC1=CC=CC=C1)=O)=O MEFWZJUZYGNHEU-UHFFFAOYSA-N 0.000 claims description 4
• YQJREFCRPCDMBW-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(C1=C(N=CC=C1)SCCC)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(C1=C(N=CC=C1)SCCC)=O)=O)=O YQJREFCRPCDMBW-UHFFFAOYSA-N 0.000 claims description 4
• GLYGAGDJHKMKAP-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(CC1=C(C(=C(C(=C1F)F)F)F)F)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(CC1=C(C(=C(C(=C1F)F)F)F)F)=O)=O)=O GLYGAGDJHKMKAP-UHFFFAOYSA-N 0.000 claims description 4
• NEFXVEKILLOOHI-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(CC1=C(C(=CC=C1)F)OC)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(CC1=C(C(=CC=C1)F)OC)=O)=O)=O NEFXVEKILLOOHI-UHFFFAOYSA-N 0.000 claims description 4
• KCGOACDKBLSFCV-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(NC=1SC=CC=1C(=O)OC)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(NC=1SC=CC=1C(=O)OC)=O)=O)=O KCGOACDKBLSFCV-UHFFFAOYSA-N 0.000 claims description 4
• YVPMACCEARLKNY-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNS(=O)(=O)C1=C(N=C(S1)NC(C)=O)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNS(=O)(=O)C1=C(N=C(S1)NC(C)=O)C)=O)=O YVPMACCEARLKNY-UHFFFAOYSA-N 0.000 claims description 4
• ZMKGBJLXWWVZOP-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNS(=O)(=O)C1=C(OC(=C1)C)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNS(=O)(=O)C1=C(OC(=C1)C)C)=O)=O ZMKGBJLXWWVZOP-UHFFFAOYSA-N 0.000 claims description 4
• WRBPZWYWOHDUIF-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNS(=O)(=O)C=1C=CC(=C(C(=O)N(C)C)C=1)OC)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNS(=O)(=O)C=1C=CC(=C(C(=O)N(C)C)C=1)OC)=O)=O WRBPZWYWOHDUIF-UHFFFAOYSA-N 0.000 claims description 4
• FQWWEKBJLDDUSI-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC(=CC=C1)F)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(=O)C1=CC(=CC=C1)F)=O)=O)=O FQWWEKBJLDDUSI-UHFFFAOYSA-N 0.000 claims description 4
• JRRFOJWDJVQAEJ-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)(F)F)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)(F)F)=O)=O)=O JRRFOJWDJVQAEJ-UHFFFAOYSA-N 0.000 claims description 4
• VIVFNUSGRRVRPM-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=NC=C1)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=NC=C1)=O)=O)=O)=O VIVFNUSGRRVRPM-UHFFFAOYSA-N 0.000 claims description 4
• HYXIGLUOHCRBJU-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)NC1=CC(=C(C=C1)C)OC)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)NC1=CC(=C(C=C1)C)OC)=O HYXIGLUOHCRBJU-UHFFFAOYSA-N 0.000 claims description 4
• AYGQSOLVYCBSII-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)NC1=NC=C(C(=N1)C(F)(F)F)C)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)NC1=NC=C(C(=N1)C(F)(F)F)C)=O AYGQSOLVYCBSII-UHFFFAOYSA-N 0.000 claims description 4
• VGPQVGYWKYOIFR-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)NCCCOC1=CC=CC=C1)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)NCCCOC1=CC=CC=C1)=O VGPQVGYWKYOIFR-UHFFFAOYSA-N 0.000 claims description 4
• JISRMFKHKGVHIE-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=S)NC1=C(C(=CC(=C1Cl)Cl)Cl)Cl)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=S)NC1=C(C(=CC(=C1Cl)Cl)Cl)Cl)=O JISRMFKHKGVHIE-UHFFFAOYSA-N 0.000 claims description 4
• OAYCXXXCYHDLEL-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=S)NC1=CC=C(C=C1)OC(F)(F)F)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=S)NC1=CC=C(C=C1)OC(F)(F)F)=O OAYCXXXCYHDLEL-UHFFFAOYSA-N 0.000 claims description 4
• RJFKGYPYKDSWQQ-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C(C)C)C1=CC=C(C=C1)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(C(C(C)C)C1=CC=C(C=C1)C(C)C)=O)=O RJFKGYPYKDSWQQ-UHFFFAOYSA-N 0.000 claims description 4
• AAEOKVFUVMLOMA-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC(=C(C=C1)OC)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC(=C(C=C1)OC)C(C)C)=O)=O AAEOKVFUVMLOMA-UHFFFAOYSA-N 0.000 claims description 4
• ATZFANCHBAWHRU-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC(=CC=C1)N1CCCCC1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC(=CC=C1)N1CCCCC1)=O)=O ATZFANCHBAWHRU-UHFFFAOYSA-N 0.000 claims description 4
• WHDWOBROXCVMST-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)C(C)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)C(C)C)=O)=O WHDWOBROXCVMST-UHFFFAOYSA-N 0.000 claims description 4
• GEYIXKHRNZDBEY-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)F)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)F)=O)=O GEYIXKHRNZDBEY-UHFFFAOYSA-N 0.000 claims description 4
• YIBUOBDIJMEQBD-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)N1CCCC1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)N1CCCC1)=O)=O YIBUOBDIJMEQBD-UHFFFAOYSA-N 0.000 claims description 4
• RLIAQVDPFWXDRZ-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)N1CCOCC1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1=CC=C(C=C1)N1CCOCC1)=O)=O RLIAQVDPFWXDRZ-UHFFFAOYSA-N 0.000 claims description 4
• GDCIWXDVLCIRMP-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1CCC(CC1)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CC1CCC(CC1)C)=O)=O GDCIWXDVLCIRMP-UHFFFAOYSA-N 0.000 claims description 4
• BWWVDSPJLIBCDH-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CCCC1=CC=C(C=C1)N1CCOCC1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CCCC1=CC=C(C=C1)N1CCOCC1)=O)=O BWWVDSPJLIBCDH-UHFFFAOYSA-N 0.000 claims description 4
• USWVDDNFVOSWPZ-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CCCC1=CC=CC=C1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CCCC1=CC=CC=C1)=O)=O USWVDDNFVOSWPZ-UHFFFAOYSA-N 0.000 claims description 4
• WUGPVSOHCYCDDR-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CN1CCOCC1)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(CN1CCOCC1)=O)=O WUGPVSOHCYCDDR-UHFFFAOYSA-N 0.000 claims description 4
• CXYVWHGMPXDHOE-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(NC1=C(SC=C1)C(=O)OC)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(NC1=C(SC=C1)C(=O)OC)=O)=O CXYVWHGMPXDHOE-UHFFFAOYSA-N 0.000 claims description 4
• RVHYEFSEIKOVEM-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(NC=1C=CC(=C(C(=O)N)C=1)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(NC=1C=CC(=C(C(=O)N)C=1)C)=O)=O RVHYEFSEIKOVEM-UHFFFAOYSA-N 0.000 claims description 4
• PLPARWOBUGAPQW-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(NC=1C=CC(=C(C=1)NC(C)=O)C)=O)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(NC=1C=CC(=C(C=1)NC(C)=O)C)=O)=O PLPARWOBUGAPQW-UHFFFAOYSA-N 0.000 claims description 4
• IPKATWXEBODXOH-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C1=C(C(=C(C(=C1F)F)F)F)F)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C1=C(C(=C(C(=C1F)F)F)F)F)=O IPKATWXEBODXOH-UHFFFAOYSA-N 0.000 claims description 4
• PSWHODZGWXZQLE-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C1=C(N=C(S1)NC(C)=O)C)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C1=C(N=C(S1)NC(C)=O)C)=O PSWHODZGWXZQLE-UHFFFAOYSA-N 0.000 claims description 4
• HTQUTOFNCCBPNQ-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C1=COC=C1)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C1=COC=C1)=O HTQUTOFNCCBPNQ-UHFFFAOYSA-N 0.000 claims description 4
• RCFFSKKQVMQSEO-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C=1N=CN(C=1)C)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNS(=O)(=O)C=1N=CN(C=1)C)=O RCFFSKKQVMQSEO-UHFFFAOYSA-N 0.000 claims description 4
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 206010046851 Uveitis Diseases 0.000 claims description 4
• CEMZBWPSKYISTN-UHFFFAOYSA-N methyl 2-amino-3-methylbutanoate Chemical compound COC(=O)C(N)C(C)C CEMZBWPSKYISTN-UHFFFAOYSA-N 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• UNNQNMXQLTZWLL-UHFFFAOYSA-N BrC1=C(OC=C1)C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound BrC1=C(OC=C1)C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 UNNQNMXQLTZWLL-UHFFFAOYSA-N 0.000 claims description 3
• ZCWAEOHSQXMRDI-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C1(CC1)C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C1(CC1)C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O ZCWAEOHSQXMRDI-UHFFFAOYSA-N 0.000 claims description 3
• NALZBWPHQRDFCZ-UHFFFAOYSA-N ClC=1SC(=CN=1)C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 Chemical compound ClC=1SC(=CN=1)C(=O)NCC1=CC2=C(C(N(C2)C2C(NC(CC2)=O)=O)=O)S1 NALZBWPHQRDFCZ-UHFFFAOYSA-N 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• CIYFLSYSKNCGTO-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)C1=C(N=NS1)C)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)C1=C(N=NS1)C)=O CIYFLSYSKNCGTO-UHFFFAOYSA-N 0.000 claims description 3
• BUUAOOYNZQWWAR-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)C=1SC=CN=1)=O Chemical compound O=C1NC(CCC1N1CC=2C(C1=O)=CSC=2CNC(=O)C=1SC=CN=1)=O BUUAOOYNZQWWAR-UHFFFAOYSA-N 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 208000037875 astrocytosis Diseases 0.000 claims description 3
• 230000007341 astrogliosis Effects 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 2
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 206010014733 Endometrial cancer Diseases 0.000 claims description 2
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
• QOIYNCWGYZJMDU-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)C=1C(=NOC=1C)C)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=C(C1)C=C(S2)CNC(=O)C=1C(=NOC=1C)C)=O)=O QOIYNCWGYZJMDU-UHFFFAOYSA-N 0.000 claims description 2
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
• 229910019142 PO4 Inorganic materials 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
• 206010039491 Sarcoma Diseases 0.000 claims description 2
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
• 201000010881 cervical cancer Diseases 0.000 claims description 2
• 208000029742 colonic neoplasm Diseases 0.000 claims description 2
• 201000004101 esophageal cancer Diseases 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• 201000010536 head and neck cancer Diseases 0.000 claims description 2
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• 201000002120 neuroendocrine carcinoma Diseases 0.000 claims description 2
• 230000002611 ovarian Effects 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
• 239000010452 phosphate Substances 0.000 claims description 2
• BWJZHYWAXLWLTB-UHFFFAOYSA-N thiophene-3-sulfonamide Chemical compound NS(=O)(=O)C=1C=CSC=1 BWJZHYWAXLWLTB-UHFFFAOYSA-N 0.000 claims description 2
• 201000002510 thyroid cancer Diseases 0.000 claims description 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 6
• 229910052698 phosphorus Inorganic materials 0.000 claims 6
• 239000011574 phosphorus Substances 0.000 claims 6
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
• 239000003814 drug Substances 0.000 abstract description 14
• 229940124597 therapeutic agent Drugs 0.000 abstract description 8
• 230000001404 mediated effect Effects 0.000 abstract description 4
• 230000004853 protein function Effects 0.000 abstract description 3
• 230000004044 response Effects 0.000 abstract description 3
• 230000007111 proteostasis Effects 0.000 abstract description 2
• 239000000243 solution Substances 0.000 description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• 125000000217 alkyl group Chemical group 0.000 description 54
• 210000004027 cell Anatomy 0.000 description 36
• 125000004429 atom Chemical group 0.000 description 34
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
• 125000005842 heteroatom Chemical group 0.000 description 30
• 125000001072 heteroaryl group Chemical group 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• 235000018102 proteins Nutrition 0.000 description 23
• QVNKLYQIVVGHRU-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)Cl)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)Cl)=O QVNKLYQIVVGHRU-UHFFFAOYSA-N 0.000 description 22
• 125000000304 alkynyl group Chemical group 0.000 description 21
• 125000003342 alkenyl group Chemical group 0.000 description 20
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 17
• 150000001721 carbon Chemical group 0.000 description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 description 17
• 239000001257 hydrogen Substances 0.000 description 17
• 239000012044 organic layer Substances 0.000 description 17
• 239000011734 sodium Substances 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• 150000002431 hydrogen Chemical class 0.000 description 15
• 238000002953 preparative HPLC Methods 0.000 description 14
• 102000000588 Interleukin-2 Human genes 0.000 description 13
• NLNVXYCBPSOFLK-UHFFFAOYSA-N O=C(C(=O)Cl)C1=CC=C(C=C1)C1(CC1)C(F)(F)F Chemical compound O=C(C(=O)Cl)C1=CC=C(C=C1)C1(CC1)C(F)(F)F NLNVXYCBPSOFLK-UHFFFAOYSA-N 0.000 description 12
• 125000002947 alkylene group Chemical group 0.000 description 12
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 10
• 125000003545 alkoxy group Chemical group 0.000 description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
• 230000000770 proinflammatory effect Effects 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• 230000006907 apoptotic process Effects 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• DEGDWEVWZGZRNK-UHFFFAOYSA-N methyl 2-(4-tert-butylpiperidin-1-yl)-2-oxoacetate Chemical compound COC(=O)C(=O)N1CCC(CC1)C(C)(C)C DEGDWEVWZGZRNK-UHFFFAOYSA-N 0.000 description 7
• QMLVCVLSZNSKJM-UHFFFAOYSA-N methyl 2-(bromomethyl)-4-cyanobenzoate Chemical compound COC(=O)C1=CC=C(C#N)C=C1CBr QMLVCVLSZNSKJM-UHFFFAOYSA-N 0.000 description 7
• PDQNYPAJSAVURS-UHFFFAOYSA-N methyl 4-cyano-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(C#N)C=C1C PDQNYPAJSAVURS-UHFFFAOYSA-N 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 125000003003 spiro group Chemical group 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• YOQYYFSVDYBQEW-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-2-oxoacetic acid Chemical compound CC(C)(C)C1=CC=C(C(=O)C(O)=O)C=C1 YOQYYFSVDYBQEW-UHFFFAOYSA-N 0.000 description 6
• XTILEMYXOZKSFJ-UHFFFAOYSA-N 3-[6-(aminomethyl)-3-oxo-1h-isoindol-2-yl]piperidine-2,6-dione;hydrochloride Chemical compound Cl.C1C2=CC(CN)=CC=C2C(=O)N1C1CCC(=O)NC1=O XTILEMYXOZKSFJ-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 206010061218 Inflammation Diseases 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 230000014509 gene expression Effects 0.000 description 6
• 230000004054 inflammatory process Effects 0.000 description 6
• 230000000670 limiting effect Effects 0.000 description 6
• WMILMIDBWBQPAB-UHFFFAOYSA-N methyl 3-bromo-2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC(Br)=C1CBr WMILMIDBWBQPAB-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 208000024891 symptom Diseases 0.000 description 6
• QPYDRCOBUFLJAS-UHFFFAOYSA-N tert-butyl n-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3h-isoindol-4-yl]methyl]carbamate Chemical compound C1C=2C(CNC(=O)OC(C)(C)C)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O QPYDRCOBUFLJAS-UHFFFAOYSA-N 0.000 description 6
• 210000001519 tissue Anatomy 0.000 description 6
• LJOJKFHNKMTEFS-UHFFFAOYSA-N 1-bromo-4-[1-(trifluoromethyl)cyclopropyl]benzene Chemical compound C=1C=C(Br)C=CC=1C1(C(F)(F)F)CC1 LJOJKFHNKMTEFS-UHFFFAOYSA-N 0.000 description 5
• NYVGCNSACSJVJQ-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1-oxo-3h-isoindole-5-carbonitrile Chemical compound C1C2=CC(C#N)=CC=C2C(=O)N1C1CCC(=O)NC1=O NYVGCNSACSJVJQ-UHFFFAOYSA-N 0.000 description 5
• KLJMOQDPIZUJLA-UHFFFAOYSA-N C(C)(C)(C)OC(NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)OC(NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O KLJMOQDPIZUJLA-UHFFFAOYSA-N 0.000 description 5
• 108010002352 Interleukin-1 Proteins 0.000 description 5
• 102000000589 Interleukin-1 Human genes 0.000 description 5
• MOIBPZPAFPFBPY-UHFFFAOYSA-N O=C(C(=O)O)C1=CC=C(C=C1)C1(CC1)C(F)(F)F Chemical compound O=C(C(=O)O)C1=CC=C(C=C1)C1(CC1)C(F)(F)F MOIBPZPAFPFBPY-UHFFFAOYSA-N 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 125000001188 haloalkyl group Chemical group 0.000 description 5
• 210000000987 immune system Anatomy 0.000 description 5
• 210000004698 lymphocyte Anatomy 0.000 description 5
• UMGORSCXGJUEMK-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindole-5-carbonitrile Chemical compound O=C1C2=CC(C#N)=CC=C2C(=O)N1C1CCC(=O)NC1=O UMGORSCXGJUEMK-UHFFFAOYSA-N 0.000 description 4
• CANZBRDGRHNSGZ-UHFFFAOYSA-N 3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)C(C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-UHFFFAOYSA-N 0.000 description 4
• GOSIHALPBLSKBX-UHFFFAOYSA-N 4-[1-(trifluoromethyl)cyclopropyl]benzaldehyde Chemical compound C=1C=C(C=O)C=CC=1C1(C(F)(F)F)CC1 GOSIHALPBLSKBX-UHFFFAOYSA-N 0.000 description 4
• MWMSBQXTHIEBNT-UHFFFAOYSA-N 5-bromo-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC(Br)=CC=C2C(=O)N1C1CCC(=O)NC1=O MWMSBQXTHIEBNT-UHFFFAOYSA-N 0.000 description 4
• QNAKVPXGJQRCNR-UHFFFAOYSA-N C(C)(C)(C)C1CCN(CC1)C(C(=O)Cl)=O Chemical compound C(C)(C)(C)C1CCN(CC1)C(C(=O)Cl)=O QNAKVPXGJQRCNR-UHFFFAOYSA-N 0.000 description 4
• RDKGZAIWUUDMAX-UHFFFAOYSA-N C(C)(C)C1=CC=C(S1)C(C(=O)Cl)=O Chemical compound C(C)(C)C1=CC=C(S1)C(C(=O)Cl)=O RDKGZAIWUUDMAX-UHFFFAOYSA-N 0.000 description 4
• ZMRBNPSXWDIFKP-UHFFFAOYSA-N C(C)(C)C1=CC=C(S1)C(C(=O)O)=O Chemical compound C(C)(C)C1=CC=C(S1)C(C(=O)O)=O ZMRBNPSXWDIFKP-UHFFFAOYSA-N 0.000 description 4
• ZHJCBJGQROOCRT-UHFFFAOYSA-N C(C)(C)C1=CC=C(S1)C(C(=O)OCC)=O Chemical compound C(C)(C)C1=CC=C(S1)C(C(=O)OCC)=O ZHJCBJGQROOCRT-UHFFFAOYSA-N 0.000 description 4
• 102000004889 Interleukin-6 Human genes 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• VKGHIEOXPIOCOT-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)C#N)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)C#N)=O)=O VKGHIEOXPIOCOT-UHFFFAOYSA-N 0.000 description 4
• XNRKTNOWMXNWHF-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)C=O)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)C=O)=O)=O XNRKTNOWMXNWHF-UHFFFAOYSA-N 0.000 description 4
• RCVQRXHGSAMHLY-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CC#N)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CC#N)=O)=O RCVQRXHGSAMHLY-UHFFFAOYSA-N 0.000 description 4
• PVUJQRQXKLDMPJ-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CO)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CO)=O)=O PVUJQRQXKLDMPJ-UHFFFAOYSA-N 0.000 description 4
• KJKQCLFKSWRBRI-UHFFFAOYSA-N NCC=1C=CC=C2CN(C(C=12)=O)C1C(NC(CC1)=O)=O Chemical compound NCC=1C=CC=C2CN(C(C=12)=O)C1C(NC(CC1)=O)=O KJKQCLFKSWRBRI-UHFFFAOYSA-N 0.000 description 4
• HENRWGDYXGMKIV-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1=O)CNC(OC(C)(C)C)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1=O)CNC(OC(C)(C)C)=O)=O)=O HENRWGDYXGMKIV-UHFFFAOYSA-N 0.000 description 4
• WJCAOTRKGFLQHG-UHFFFAOYSA-N O=C1NC(CCC1N1CC=2C=CC=C(C=2C1=O)C#N)=O Chemical compound O=C1NC(CCC1N1CC=2C=CC=C(C=2C1=O)C#N)=O WJCAOTRKGFLQHG-UHFFFAOYSA-N 0.000 description 4
• 230000003110 anti-inflammatory effect Effects 0.000 description 4
• 230000004071 biological effect Effects 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 239000006196 drop Substances 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
• 210000002540 macrophage Anatomy 0.000 description 4
• MSXPMFZZUHOIIN-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-cyanobenzoate Chemical compound COC(=O)C1=C(CBr)C=CC=C1C#N MSXPMFZZUHOIIN-UHFFFAOYSA-N 0.000 description 4
• OVCFEGUYKGFRQT-UHFFFAOYSA-N methyl 2-cyano-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1C#N OVCFEGUYKGFRQT-UHFFFAOYSA-N 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 230000017854 proteolysis Effects 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 4
• 230000004083 survival effect Effects 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• FQHCQCMVQOWSNW-UHFFFAOYSA-N tert-butyl 5-amino-4-(7-bromo-3-oxo-1H-isoindol-2-yl)-5-oxopentanoate Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)Br)=O)=O FQHCQCMVQOWSNW-UHFFFAOYSA-N 0.000 description 4
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
• DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 3
• LWMOTIQKAURFAC-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1-oxo-3h-isoindole-4-carbonitrile Chemical compound C1C(C(=CC=C2)C#N)=C2C(=O)N1C1CCC(=O)NC1=O LWMOTIQKAURFAC-UHFFFAOYSA-N 0.000 description 3
• IPSGOMWAGOYNKO-UHFFFAOYSA-N 3-[6-(aminomethyl)-3-oxo-1h-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1C2=CC(CN)=CC=C2C(=O)N1C1CCC(=O)NC1=O IPSGOMWAGOYNKO-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 208000023275 Autoimmune disease Diseases 0.000 description 3
• SCZFMUWTABGOGF-UHFFFAOYSA-N BrC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O Chemical compound BrC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O SCZFMUWTABGOGF-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• VLHYXGPPBJFXPS-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CCN)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CCN)=O)=O VLHYXGPPBJFXPS-UHFFFAOYSA-N 0.000 description 3
• OWSNJQGRGQQEKR-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CCl)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=C(C=C2C1)CCl)=O)=O OWSNJQGRGQQEKR-UHFFFAOYSA-N 0.000 description 3
• CNXBJLKTNLHCDW-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)C=O)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)C=O)=O)=O CNXBJLKTNLHCDW-UHFFFAOYSA-N 0.000 description 3
• QCTPZILGDUKUMI-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)CNC)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)CNC)=O)=O QCTPZILGDUKUMI-UHFFFAOYSA-N 0.000 description 3
• XTDZQAQAEPPETQ-UHFFFAOYSA-N O=C(C(=O)OCC)C=1SC(=CC=1)C(=C)C Chemical compound O=C(C(=O)OCC)C=1SC(=CC=1)C(=C)C XTDZQAQAEPPETQ-UHFFFAOYSA-N 0.000 description 3
• VRZDATOKGOTTSS-UHFFFAOYSA-N O=C1NC(CCC1N1CC2=CC=CC(=C2C1=O)CNC(OC(C)(C)C)=O)=O Chemical compound O=C1NC(CCC1N1CC2=CC=CC(=C2C1=O)CNC(OC(C)(C)C)=O)=O VRZDATOKGOTTSS-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 102000034527 Retinoid X Receptors Human genes 0.000 description 3
• 108010038912 Retinoid X Receptors Proteins 0.000 description 3
• 125000005631 S-sulfonamido group Chemical group 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 102000044159 Ubiquitin Human genes 0.000 description 3
• 108090000848 Ubiquitin Proteins 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 230000004913 activation Effects 0.000 description 3
• 238000001994 activation Methods 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 125000005110 aryl thio group Chemical group 0.000 description 3
• 125000004104 aryloxy group Chemical group 0.000 description 3
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 230000003828 downregulation Effects 0.000 description 3
• 230000006870 function Effects 0.000 description 3
• 230000004927 fusion Effects 0.000 description 3
• 125000001183 hydrocarbyl group Chemical group 0.000 description 3
• 230000001965 increasing effect Effects 0.000 description 3
• 239000002207 metabolite Substances 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 125000003367 polycyclic group Chemical group 0.000 description 3
• 230000003389 potentiating effect Effects 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 230000001105 regulatory effect Effects 0.000 description 3
• 208000017520 skin disease Diseases 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
• 230000014616 translation Effects 0.000 description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• WUTRCAACSOSTCN-UHFFFAOYSA-N 1-[4-[1-(trifluoromethyl)cyclopropyl]phenyl]ethanone Chemical compound FC(C1(CC1)C1=CC=C(C=C1)C(C)=O)(F)F WUTRCAACSOSTCN-UHFFFAOYSA-N 0.000 description 2
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
• LVJSNECQDVVLEF-UHFFFAOYSA-N 3-[7-(aminomethyl)-3-oxo-1h-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1C=2C(CN)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O LVJSNECQDVVLEF-UHFFFAOYSA-N 0.000 description 2
• YCPULGHBTPQLRH-UHFFFAOYSA-N 3-aminopiperidine-2,6-dione;hydron;chloride Chemical class Cl.NC1CCC(=O)NC1=O YCPULGHBTPQLRH-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• DANDTMGGYNCQLG-UHFFFAOYSA-N 4h-1,3-oxazol-5-one Chemical compound O=C1CN=CO1 DANDTMGGYNCQLG-UHFFFAOYSA-N 0.000 description 2
• OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 2
• BCKVHOUUJMYIAN-UHFFFAOYSA-N 5-bromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1 BCKVHOUUJMYIAN-UHFFFAOYSA-N 0.000 description 2
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 241000283690 Bos taurus Species 0.000 description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
• PBQMEBZRNZETLB-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O PBQMEBZRNZETLB-UHFFFAOYSA-N 0.000 description 2
• 208000005623 Carcinogenesis Diseases 0.000 description 2
• 201000009030 Carcinoma Diseases 0.000 description 2
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 101100369992 Homo sapiens TNFSF10 gene Proteins 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• 208000003456 Juvenile Arthritis Diseases 0.000 description 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
• 206010027476 Metastases Diseases 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• 108700012411 TNFSF10 Proteins 0.000 description 2
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
• 102100024598 Tumor necrosis factor ligand superfamily member 10 Human genes 0.000 description 2
• 102000006275 Ubiquitin-Protein Ligases Human genes 0.000 description 2
• 108010083111 Ubiquitin-Protein Ligases Proteins 0.000 description 2
• 230000001594 aberrant effect Effects 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 125000003277 amino group Chemical class 0.000 description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 description 2
• 239000002260 anti-inflammatory agent Substances 0.000 description 2
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 230000036952 cancer formation Effects 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 231100000504 carcinogenesis Toxicity 0.000 description 2
• 210000003169 central nervous system Anatomy 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• PMBGHMBDWGNJJE-UHFFFAOYSA-N ethyl 2-(5-bromothiophen-2-yl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C(Br)S1 PMBGHMBDWGNJJE-UHFFFAOYSA-N 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 125000004438 haloalkoxy group Chemical group 0.000 description 2
• 125000004475 heteroaralkyl group Chemical group 0.000 description 2
• 150000004677 hydrates Chemical class 0.000 description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
• 229910052738 indium Inorganic materials 0.000 description 2
• 230000007794 irritation Effects 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
• 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 230000009401 metastasis Effects 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• DDJSNWUTQDNGIZ-UHFFFAOYSA-N methyl 2-bromo-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1Br DDJSNWUTQDNGIZ-UHFFFAOYSA-N 0.000 description 2
• MKQQTCSBXHAYQL-UHFFFAOYSA-N methyl 3-bromo-2-methylbenzoate Chemical compound COC(=O)C1=CC=CC(Br)=C1C MKQQTCSBXHAYQL-UHFFFAOYSA-N 0.000 description 2
• 210000001616 monocyte Anatomy 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
• 125000000160 oxazolidinyl group Chemical group 0.000 description 2
• 125000000466 oxiranyl group Chemical group 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• NPWMTBZSRRLQNJ-UHFFFAOYSA-N pyroglutamine Chemical compound NC1CCC(=O)NC1=O NPWMTBZSRRLQNJ-UHFFFAOYSA-N 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• 238000012385 systemic delivery Methods 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 238000013519 translation Methods 0.000 description 2
• 238000012384 transportation and delivery Methods 0.000 description 2
• 125000005423 trihalomethanesulfonamido group Chemical group 0.000 description 2
• 125000005152 trihalomethanesulfonyl group Chemical group 0.000 description 2
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
• 230000034512 ubiquitination Effects 0.000 description 2
• 238000010798 ubiquitination Methods 0.000 description 2
• NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• FLOJNXXFMHCMMR-UHFFFAOYSA-N 1,3-dithiolanyl Chemical group [CH]1SCCS1 FLOJNXXFMHCMMR-UHFFFAOYSA-N 0.000 description 1
• KFHQOZXAFUKFNB-UHFFFAOYSA-N 1,3-oxathiolanyl Chemical group [CH]1OCCS1 KFHQOZXAFUKFNB-UHFFFAOYSA-N 0.000 description 1
• 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
• UXZAZECRWAGADY-UHFFFAOYSA-N 2-(4-tert-butylpiperidin-1-yl)-2-oxoacetic acid Chemical compound CC(C)(C)C1CCN(C(=O)C(O)=O)CC1 UXZAZECRWAGADY-UHFFFAOYSA-N 0.000 description 1
• YKFGLGXRUVEMNF-UHFFFAOYSA-N 2-(dimethylamino)-2-oxoacetic acid Chemical compound CN(C)C(=O)C(O)=O YKFGLGXRUVEMNF-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
• WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
• JSFRSYKISJDMTD-UHFFFAOYSA-N 3-[3-(aminomethyl)-6-oxo-4H-thieno[3,4-c]pyrrol-5-yl]piperidine-2,6-dione Chemical compound NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O JSFRSYKISJDMTD-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
• 125000005986 4-piperidonyl group Chemical group 0.000 description 1
• RWQQDIHTYQYXDX-UHFFFAOYSA-N 4-tert-butylpiperidine;hydrochloride Chemical compound Cl.CC(C)(C)C1CCNCC1 RWQQDIHTYQYXDX-UHFFFAOYSA-N 0.000 description 1
• 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 description 1
• KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 241000125205 Anethum Species 0.000 description 1
• 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• NRVUBZPHTGPNSG-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(=O)NC1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O NRVUBZPHTGPNSG-UHFFFAOYSA-N 0.000 description 1
• GGJLEMQEZAJJBS-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2C(N(CC2=CC=C1)C1C(NC(CC1)=O)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2C(N(CC2=CC=C1)C1C(NC(CC1)=O)=O)=O)=O GGJLEMQEZAJJBS-UHFFFAOYSA-N 0.000 description 1
• HYBZMGVRVCNZNN-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O HYBZMGVRVCNZNN-UHFFFAOYSA-N 0.000 description 1
• ADUMYHFTWGNTMP-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O ADUMYHFTWGNTMP-UHFFFAOYSA-N 0.000 description 1
• VYKKDKIYXWKVKJ-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C=1C=C(C=CC=1)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O VYKKDKIYXWKVKJ-UHFFFAOYSA-N 0.000 description 1
• MDDJNOLWGLLRCF-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O MDDJNOLWGLLRCF-UHFFFAOYSA-N 0.000 description 1
• CFICQJHREUYPHB-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=CC=1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound C(C)(C)(C)C=1C=C(C=CC=1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O CFICQJHREUYPHB-UHFFFAOYSA-N 0.000 description 1
• 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
• NWTNHNNQLHLSEB-UHFFFAOYSA-N CC1=C(C(=CC(=C1)C)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound CC1=C(C(=CC(=C1)C)C)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O NWTNHNNQLHLSEB-UHFFFAOYSA-N 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• 102000008122 Casein Kinase I Human genes 0.000 description 1
• 108010049812 Casein Kinase I Proteins 0.000 description 1
• 102000019034 Chemokines Human genes 0.000 description 1
• 108010012236 Chemokines Proteins 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• VFMGAOXATIYQEC-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O Chemical compound ClC=1C=C(C=CC=1Cl)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O VFMGAOXATIYQEC-UHFFFAOYSA-N 0.000 description 1
• 108020004705 Codon Proteins 0.000 description 1
• 230000033616 DNA repair Effects 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 108010008165 Etanercept Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 101710151739 Eukaryotic peptide chain release factor GTP-binding subunit ERF3A Proteins 0.000 description 1
• 101150064015 FAS gene Proteins 0.000 description 1
• 102100026693 FAS-associated death domain protein Human genes 0.000 description 1
• WIXJHLAEXABRLP-UHFFFAOYSA-N FC(C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)(F)F Chemical compound FC(C1=CC=C(C=C1)C(C(=O)NCC=1SC=C2C=1CN(C2=O)C1C(NC(CC1)=O)=O)=O)(F)F WIXJHLAEXABRLP-UHFFFAOYSA-N 0.000 description 1
• VTCHNKSRQIYRNS-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound FC=1C=C(C=CC=1F)C(C(=O)NCC1=C2CN(C(C2=CC=C1)=O)C1C(NC(CC1)=O)=O)=O VTCHNKSRQIYRNS-UHFFFAOYSA-N 0.000 description 1
• IOMURRUSRKYLQO-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O Chemical compound FC=1C=C(C=CC=1F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O IOMURRUSRKYLQO-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 208000034826 Genetic Predisposition to Disease Diseases 0.000 description 1
• 206010061431 Glial scar Diseases 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 1
• 101000911074 Homo sapiens FAS-associated death domain protein Proteins 0.000 description 1
• 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 1
• 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 102000039995 Ikaros C2H2-type zinc-finger protein family Human genes 0.000 description 1
• 108091069197 Ikaros C2H2-type zinc-finger protein family Proteins 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 102000019223 Interleukin-1 receptor Human genes 0.000 description 1
• 108050006617 Interleukin-1 receptor Proteins 0.000 description 1
• 108090000978 Interleukin-4 Proteins 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
• OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• KSDVQDOFLUNWKH-UHFFFAOYSA-N NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)C#N)=O)=O Chemical compound NC(C(CCC(=O)OC(C)(C)C)N1C(C2=CC=CC(=C2C1)C#N)=O)=O KSDVQDOFLUNWKH-UHFFFAOYSA-N 0.000 description 1
• 238000005481 NMR spectroscopy Methods 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• KJFVHGGYVHDLAJ-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1C)C)C)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1C)C)C)=O)=O)=O)=O KJFVHGGYVHDLAJ-UHFFFAOYSA-N 0.000 description 1
• CEFRADKDQPLKPO-UHFFFAOYSA-N O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=CC(=C2C1)CNC(C(C1=CC=C(C=C1)C(F)(F)F)=O)=O)=O)=O CEFRADKDQPLKPO-UHFFFAOYSA-N 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 208000002193 Pain Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 102000001708 Protein Isoforms Human genes 0.000 description 1
• 108010029485 Protein Isoforms Proteins 0.000 description 1
• 241000720974 Protium Species 0.000 description 1
• 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 description 1
• 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 description 1
• 208000020410 Psoriasis-related juvenile idiopathic arthritis Diseases 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 108020004511 Recombinant DNA Proteins 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
• 102100040247 Tumor necrosis factor Human genes 0.000 description 1
• 102000018478 Ubiquitin-Activating Enzymes Human genes 0.000 description 1
• 108010091546 Ubiquitin-Activating Enzymes Proteins 0.000 description 1
• 108060008747 Ubiquitin-Conjugating Enzyme Proteins 0.000 description 1
• 102000003431 Ubiquitin-Conjugating Enzyme Human genes 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 108091007916 Zinc finger transcription factors Proteins 0.000 description 1
• 102000038627 Zinc finger transcription factors Human genes 0.000 description 1
• SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 230000002424 anti-apoptotic effect Effects 0.000 description 1
• 239000000427 antigen Substances 0.000 description 1
• 102000036639 antigens Human genes 0.000 description 1
• 108091007433 antigens Proteins 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 230000001640 apoptogenic effect Effects 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 230000003305 autocrine Effects 0.000 description 1
• 125000003725 azepanyl group Chemical group 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 125000003828 azulenyl group Chemical group 0.000 description 1
• 210000003719 b-lymphocyte Anatomy 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 108700000711 bcl-X Proteins 0.000 description 1
• 102000055104 bcl-X Human genes 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 239000008366 buffered solution Substances 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 230000008619 cell matrix interaction Effects 0.000 description 1
• 230000012292 cell migration Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 230000004637 cellular stress Effects 0.000 description 1
• 239000002738 chelating agent Substances 0.000 description 1
• 230000002925 chemical effect Effects 0.000 description 1
• 229910052729 chemical element Inorganic materials 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• PJBIHXWYDMFGCV-UHFFFAOYSA-N chloro(chlorosulfonyloxy)methane Chemical compound ClCOS(Cl)(=O)=O PJBIHXWYDMFGCV-UHFFFAOYSA-N 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 239000000084 colloidal system Substances 0.000 description 1
• 238000002648 combination therapy Methods 0.000 description 1
• 229940125846 compound 25 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 230000003436 cytoskeletal effect Effects 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 125000005508 decahydronaphthalenyl group Chemical group 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 210000004443 dendritic cell Anatomy 0.000 description 1
• NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 239000003221 ear drop Substances 0.000 description 1
• 229940047652 ear drops Drugs 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• 239000003532 endogenous pyrogen Substances 0.000 description 1
• 210000002889 endothelial cell Anatomy 0.000 description 1
• 230000001973 epigenetic effect Effects 0.000 description 1
• 210000002919 epithelial cell Anatomy 0.000 description 1
• 229960000403 etanercept Drugs 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 108020001507 fusion proteins Proteins 0.000 description 1
• 102000037865 fusion proteins Human genes 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 210000002865 immune cell Anatomy 0.000 description 1
• 230000003308 immunostimulating effect Effects 0.000 description 1
• 239000003018 immunosuppressive agent Substances 0.000 description 1
• 229940125721 immunosuppressive agent Drugs 0.000 description 1
• 239000005414 inactive ingredient Substances 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 239000012678 infectious agent Substances 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 230000004968 inflammatory condition Effects 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000028709 inflammatory response Effects 0.000 description 1
• 229960000598 infliximab Drugs 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 230000008611 intercellular interaction Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 238000007914 intraventricular administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 230000002427 irreversible effect Effects 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
• 125000003971 isoxazolinyl group Chemical group 0.000 description 1
• 238000005304 joining Methods 0.000 description 1
• 210000002510 keratinocyte Anatomy 0.000 description 1
• 150000003951 lactams Chemical class 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229960000448 lactic acid Drugs 0.000 description 1
• 150000002596 lactones Chemical class 0.000 description 1
• 230000002045 lasting effect Effects 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 238000005461 lubrication Methods 0.000 description 1
• 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229940099690 malic acid Drugs 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 229940126601 medicinal product Drugs 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 230000001394 metastastic effect Effects 0.000 description 1
• 206010061289 metastatic neoplasm Diseases 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• CEMZBWPSKYISTN-RXMQYKEDSA-N methyl (2r)-2-amino-3-methylbutanoate Chemical compound COC(=O)[C@H](N)C(C)C CEMZBWPSKYISTN-RXMQYKEDSA-N 0.000 description 1
• ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 230000003278 mimic effect Effects 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000000394 mitotic effect Effects 0.000 description 1
• 125000006682 monohaloalkyl group Chemical group 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 125000001326 naphthylalkyl group Chemical group 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
• 108020004707 nucleic acids Proteins 0.000 description 1
• 102000039446 nucleic acids Human genes 0.000 description 1
• 150000007523 nucleic acids Chemical class 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 230000008520 organization Effects 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 238000012261 overproduction Methods 0.000 description 1
• 125000005968 oxazolinyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000003076 paracrine Effects 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000000737 periodic effect Effects 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000001766 physiological effect Effects 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 239000000955 prescription drug Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 229940076372 protein antagonist Drugs 0.000 description 1
• 238000001243 protein synthesis Methods 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 230000022983 regulation of cell cycle Effects 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 230000036573 scar formation Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 230000011664 signaling Effects 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 239000008279 sol Substances 0.000 description 1
• 230000020347 spindle assembly Effects 0.000 description 1
• LMUMMJCCZMWLEN-UHFFFAOYSA-N spiro[3.3]heptyl Chemical group [CH]1CCC11CCC1 LMUMMJCCZMWLEN-UHFFFAOYSA-N 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
• 229910000080 stannane Inorganic materials 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 230000000707 stereoselective effect Effects 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 230000008685 targeting Effects 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229960001367 tartaric acid Drugs 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• NWLREMKEFHDCSV-UHFFFAOYSA-N tert-butyl 4,5-diamino-5-oxopentanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CCC(N)C(N)=O NWLREMKEFHDCSV-UHFFFAOYSA-N 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• 125000000464 thioxo group Chemical group S=* 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000004952 trihaloalkoxy group Chemical group 0.000 description 1
• 125000004385 trihaloalkyl group Chemical group 0.000 description 1
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
• 229960000604 valproic acid Drugs 0.000 description 1
• 230000029812 viral genome replication Effects 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1