EA027345B1 - Соединения карбазола, применяемые в качестве ингибиторов бромодомена - Google Patents

Info

Publication number

EA027345B1

EA027345B1 EA201591591A EA201591591A EA027345B1 EA 027345 B1 EA027345 B1 EA 027345B1 EA 201591591 A EA201591591 A EA 201591591A EA 201591591 A EA201591591 A EA 201591591A EA 027345 B1 EA027345 B1 EA 027345B1

Authority

EA

Eurasian Patent Office

Prior art keywords

dimethyl

carbazole

carboxamide

oxazol

carbonyl

Prior art date

2013-02-27

Links

• Espacenet
• Global Dossier
• Discuss

• 108050009021 Bromodomains Proteins 0.000 title claims description 22
• 102000001805 Bromodomains Human genes 0.000 title claims description 22
• 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract description 7
• 239000003112 inhibitor Substances 0.000 title description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 143
• 238000000034 method Methods 0.000 claims abstract description 66
• 238000011282 treatment Methods 0.000 claims abstract description 27
• -1 -NHCONK 7 K 8 Chemical group 0.000 claims description 558
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 94
• 229910052736 halogen Inorganic materials 0.000 claims description 87
• 125000005842 heteroatom Chemical group 0.000 claims description 70
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 64
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• 125000004432 carbon atom Chemical group C* 0.000 claims description 62
• 150000002367 halogens Chemical group 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 41
• 125000004043 oxo group Chemical group O=* 0.000 claims description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• LDPRPCQCLNSMAO-UHFFFAOYSA-N 9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C(=O)N LDPRPCQCLNSMAO-UHFFFAOYSA-N 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 25
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 17
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 16
• 229940125763 bromodomain inhibitor Drugs 0.000 claims description 15
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 239000013256 coordination polymer Substances 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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 12
• VEARIFFTYFXLCQ-UHFFFAOYSA-N 6-(3,3-difluoroazetidine-1-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 VEARIFFTYFXLCQ-UHFFFAOYSA-N 0.000 claims description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• ATORFWZVAHCMRC-BETUJISGSA-N 6-[(2s,6r)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(NC=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 ATORFWZVAHCMRC-BETUJISGSA-N 0.000 claims description 7
• QNZWPJDXSCKNSE-UHFFFAOYSA-N 6-amino-9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N)=CC=C3N(CC=3C=CC=CC=3)C2=C1 QNZWPJDXSCKNSE-UHFFFAOYSA-N 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• JYBWZOGNOBBOPI-UHFFFAOYSA-N [7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazol-3-yl]-morpholin-4-ylmethanone Chemical compound CC1=NOC(C)=C1C1=CC=C2C3=CC(C(=O)N4CCOCC4)=CC=C3NC2=C1 JYBWZOGNOBBOPI-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000001425 triazolyl group Chemical group 0.000 claims description 7
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
• PTXYHIKUWBROMP-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-methoxy-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(OC)=CC=C2N1C(C)C1=CC=CC=C1 PTXYHIKUWBROMP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 201000002528 pancreatic cancer Diseases 0.000 claims description 6
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 6
• OGKSFYZMAHNNLF-UHFFFAOYSA-N 9-[(4-fluorophenyl)methyl]-2-(3-methyl-1,2-oxazol-4-yl)-6-(morpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCOCC4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 OGKSFYZMAHNNLF-UHFFFAOYSA-N 0.000 claims description 5
• UUGVHOIJFXIXQT-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(methylamino)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(NC)=CC=C2N1CC1=CC=CC=C1 UUGVHOIJFXIXQT-UHFFFAOYSA-N 0.000 claims description 5
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
• 208000034578 Multiple myelomas Diseases 0.000 claims description 5
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 5
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
• PIEGZRMSZHBJHE-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazinan-3-yl)-9h-carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCCC4)=O)=CC=C3NC2=C1 PIEGZRMSZHBJHE-UHFFFAOYSA-N 0.000 claims description 4
• GTAOHKMCIIWAQH-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[4,4,4-trifluoro-1-[2-(trifluoromethyl)phenyl]butyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(CCC(F)(F)F)C=3C(=CC=CC=3)C(F)(F)F)C2=C1 GTAOHKMCIIWAQH-UHFFFAOYSA-N 0.000 claims description 4
• GZPXPLRXQLLVER-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-8-fluoro-9-[(4-fluorophenyl)-(oxan-4-yl)methyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C(F)=C3N(C(C3CCOCC3)C=3C=CC(F)=CC=3)C2=C1 GZPXPLRXQLLVER-UHFFFAOYSA-N 0.000 claims description 4
• JTNMXAFOHVDABG-UHFFFAOYSA-N 2-(3,5-dimethyltriazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[oxan-4-yl(phenyl)methyl]carbazole-4-carboxamide Chemical compound N1=NN(C)C(C=2C=C3C(C4=CC=C(C=C4N3C(C3CCOCC3)C=3C=CC=CC=3)C(C)(C)O)=C(C(N)=O)C=2)=C1C JTNMXAFOHVDABG-UHFFFAOYSA-N 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• YRRAHVLMNLTOCP-UHFFFAOYSA-N 6-[acetyl(2-fluoroethyl)amino]-9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(N(CCF)C(=O)C)=CC=C2N1CC1=CC=CC=C1 YRRAHVLMNLTOCP-UHFFFAOYSA-N 0.000 claims description 4
• VUPVKCXZTKAVRO-UHFFFAOYSA-N 9-[(4,4-difluorocyclohexyl)-phenylmethyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-8-fluoro-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C(F)=C3N(C(C3CCC(F)(F)CC3)C=3C=CC=CC=3)C2=C1 VUPVKCXZTKAVRO-UHFFFAOYSA-N 0.000 claims description 4
• AGOKHABSPPNEPI-UHFFFAOYSA-N 9-[1-(4-chlorophenyl)ethyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=C(Cl)C=C1 AGOKHABSPPNEPI-UHFFFAOYSA-N 0.000 claims description 4
• FHCKTQREELEKJA-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(morpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCOCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 FHCKTQREELEKJA-UHFFFAOYSA-N 0.000 claims description 4
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 4
• 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims description 4
• 201000011176 T-cell adult acute lymphocytic leukemia Diseases 0.000 claims description 4
• 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 208000022679 triple-negative breast carcinoma Diseases 0.000 claims description 4
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
• CQRYHAYNFAANAL-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 CQRYHAYNFAANAL-UHFFFAOYSA-N 0.000 claims description 3
• MDDROMACACANRC-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(1-fluorocyclobutyl)-phenylmethyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C=3C=CC=CC=3)C3(F)CCC3)C2=C1 MDDROMACACANRC-UHFFFAOYSA-N 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• OCQFABHPPPLKEB-UHFFFAOYSA-N 6-acetamido-9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(NC(=O)C)=CC=C2N1CC1=CC=CC=C1 OCQFABHPPPLKEB-UHFFFAOYSA-N 0.000 claims description 3
• IPLUSVYZVAARQA-UHFFFAOYSA-N 9-[(4-chlorophenyl)methyl]-6-(3,3-difluoroazetidine-1-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)(F)C4)=CC=C3N(CC=3C=CC(Cl)=CC=3)C2=C1 IPLUSVYZVAARQA-UHFFFAOYSA-N 0.000 claims description 3
• RRTPEQSENSZSGP-UHFFFAOYSA-N 9-[(4-fluorophenyl)methyl]-2-(5-methyl-1,2-oxazol-4-yl)-6-(morpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound O1N=CC(C=2C=C3C(C4=CC(=CC=C4N3CC=3C=CC(F)=CC=3)C(=O)N3CCOCC3)=C(C(N)=O)C=2)=C1C RRTPEQSENSZSGP-UHFFFAOYSA-N 0.000 claims description 3
• FEIGTQOBIXCBEM-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-fluoroethylamino)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NCCF)=CC=C3N(CC=3C=CC=CC=3)C2=C1 FEIGTQOBIXCBEM-UHFFFAOYSA-N 0.000 claims description 3
• JHQQSHKOWFPSSU-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(methanesulfonamido)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NS(C)(=O)=O)=CC=C3N(CC=3C=CC=CC=3)C2=C1 JHQQSHKOWFPSSU-UHFFFAOYSA-N 0.000 claims description 3
• HIYUJSFLCISMKN-UHFFFAOYSA-N 9-benzyl-6-(2,2-difluoroethylamino)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NCC(F)F)=CC=C3N(CC=3C=CC=CC=3)C2=C1 HIYUJSFLCISMKN-UHFFFAOYSA-N 0.000 claims description 3
• ZAFLLMMYYRPKRQ-UHFFFAOYSA-N 9-benzyl-6-(cyanomethylamino)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NCC#N)=CC=C3N(CC=3C=CC=CC=3)C2=C1 ZAFLLMMYYRPKRQ-UHFFFAOYSA-N 0.000 claims description 3
• GOAXKYCIBZKQHE-UHFFFAOYSA-N 9-benzyl-6-[bis(2-hydroxyethyl)amino]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N(CCO)CCO)=CC=C3N(CC=3C=CC=CC=3)C2=C1 GOAXKYCIBZKQHE-UHFFFAOYSA-N 0.000 claims description 3
• JMIUNFHRLOUABQ-IYBDPMFKSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-ethylcarbazol-3-yl]methanone Chemical compound C1=C2N(CC)C3=CC=C(C(=O)N4C[C@@H](C)O[C@@H](C)C4)C=C3C2=CC=C1C=1C(C)=NOC=1C JMIUNFHRLOUABQ-IYBDPMFKSA-N 0.000 claims description 3
• MYZQINULMLOYKC-KDURUIRLSA-N [6-[(2s,6r)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-9-yl]-phenylmethanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(C(=O)C=2C=CC=CC=2)C=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 MYZQINULMLOYKC-KDURUIRLSA-N 0.000 claims description 3
• HPAIGTBNYZVHCU-UHFFFAOYSA-N [7-(3,5-dimethyl-1,2-oxazol-4-yl)-5-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazol-3-yl]-(3-fluoroazetidin-1-yl)methanone Chemical compound CC1=NOC(C)=C1C1=CC(C(=O)N2CC(F)C2)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 HPAIGTBNYZVHCU-UHFFFAOYSA-N 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• HGMXUMBQBAMBKV-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(3-fluorophenyl)methyl]carbazole-4-carbonitrile Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=C(F)C=CC=3)C2=C1 HGMXUMBQBAMBKV-UHFFFAOYSA-N 0.000 claims description 2
• CPALAFLOXDEHLR-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 CPALAFLOXDEHLR-UHFFFAOYSA-N 0.000 claims description 2
• CDCFPXLNCLGDCB-UHFFFAOYSA-N 2-methyl-1,9-dihydrocarbazole-2,5-dicarboxamide Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1CC(C(N)=O)(C)C=C2 CDCFPXLNCLGDCB-UHFFFAOYSA-N 0.000 claims description 2
• YGYQWGCAQWENJP-UHFFFAOYSA-N 6-(azetidine-1-carbonyl)-9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 YGYQWGCAQWENJP-UHFFFAOYSA-N 0.000 claims description 2
• MYMJPRRNYAFYPX-HDICACEKSA-N 9-(benzenesulfonyl)-6-[(2s,6r)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)S(=O)(=O)C=2C=CC=CC=2)C3=C1 MYMJPRRNYAFYPX-HDICACEKSA-N 0.000 claims description 2
• WGAKEWCXPMTYNX-HDICACEKSA-N 9-benzoyl-6-[(2s,6r)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(C(=O)C=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 WGAKEWCXPMTYNX-HDICACEKSA-N 0.000 claims description 2
• BRVQJCHSGZLPPW-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(1,4-oxazepane-4-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCOCCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 BRVQJCHSGZLPPW-UHFFFAOYSA-N 0.000 claims description 2
• RHJPFNFHGDXFGN-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-hydroxyethylamino)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NCCO)=CC=C3N(CC=3C=CC=CC=3)C2=C1 RHJPFNFHGDXFGN-UHFFFAOYSA-N 0.000 claims description 2
• VDVJEIMYOOPFSI-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-methylazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1CCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 VDVJEIMYOOPFSI-UHFFFAOYSA-N 0.000 claims description 2
• HXQTXEJJHBTZBI-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-methylmorpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound C1COC(C)CN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 HXQTXEJJHBTZBI-UHFFFAOYSA-N 0.000 claims description 2
• VDGBZAUCONLKDW-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-methylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1CCCCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 VDGBZAUCONLKDW-UHFFFAOYSA-N 0.000 claims description 2
• VWYMZSJPNGWZJD-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 VWYMZSJPNGWZJD-UHFFFAOYSA-N 0.000 claims description 2
• PGROQSOUIQKXRN-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-hydroxyazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(O)C4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 PGROQSOUIQKXRN-UHFFFAOYSA-N 0.000 claims description 2
• SKOHMXSCNZUPCJ-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-hydroxypiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCC(O)CC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 SKOHMXSCNZUPCJ-UHFFFAOYSA-N 0.000 claims description 2
• FVFRBITYXRULOH-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-methoxypiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound C1CC(OC)CCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 FVFRBITYXRULOH-UHFFFAOYSA-N 0.000 claims description 2
• LBXGUVWGWADUJG-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-methylpiperazine-1-carbonyl)carbazole-4-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 LBXGUVWGWADUJG-UHFFFAOYSA-N 0.000 claims description 2
• MQJAZMGJKBJUAZ-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-methylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 MQJAZMGJKBJUAZ-UHFFFAOYSA-N 0.000 claims description 2
• DNXXKUSHRHXLGK-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(oxane-4-carbonylamino)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NC(=O)C4CCOCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 DNXXKUSHRHXLGK-UHFFFAOYSA-N 0.000 claims description 2
• MUXWSGPORBEBNB-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-methoxycarbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 MUXWSGPORBEBNB-UHFFFAOYSA-N 0.000 claims description 2
• MUFQCXNLYTYSGT-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-methylsulfonylcarbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(S(C)(=O)=O)=CC=C3N(CC=3C=CC=CC=3)C2=C1 MUFQCXNLYTYSGT-UHFFFAOYSA-N 0.000 claims description 2
• DEGXCADDIWELKL-UHFFFAOYSA-N 9-benzyl-6-(cyclopentanecarbonylamino)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NC(=O)C4CCCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 DEGXCADDIWELKL-UHFFFAOYSA-N 0.000 claims description 2
• DEKWESIDZKELOZ-UHFFFAOYSA-N [9-(cyclopropylmethyl)-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-morpholin-4-ylmethanone Chemical compound CC1=NOC(C)=C1C1=CC=C2C3=CC(C(=O)N4CCOCC4)=CC=C3N(CC3CC3)C2=C1 DEKWESIDZKELOZ-UHFFFAOYSA-N 0.000 claims description 2
• 150000003857 carboxamides Chemical class 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• WDVBBZXERNHBNP-UHFFFAOYSA-N methyl 9-benzhydryl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C2=C(C(N)=O)C=C(C=C22)C3=C(ON=C3C)C)C=1N2C(C=1C=CC=CC=1)C1=CC=CC=C1 WDVBBZXERNHBNP-UHFFFAOYSA-N 0.000 claims description 2
• DVYNFYBBONTKLE-UHFFFAOYSA-N methyl 9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C2=C(C(N)=O)C=C(C=C22)C3=C(ON=C3C)C)C=1N2CC1=CC=CC=C1 DVYNFYBBONTKLE-UHFFFAOYSA-N 0.000 claims description 2
• DAHMGJCFYANPJX-UHFFFAOYSA-N methyl 9-benzyl-5-cyano-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C2=C(C#N)C=C(C=C22)C3=C(ON=C3C)C)C=1N2CC1=CC=CC=C1 DAHMGJCFYANPJX-UHFFFAOYSA-N 0.000 claims description 2
• CRKCGNJIKMXEMN-UHFFFAOYSA-N n-[9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]morpholine-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(NC(=O)N4CCOCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 CRKCGNJIKMXEMN-UHFFFAOYSA-N 0.000 claims description 2
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 14
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
• URPYZYLDIAFPSN-UHFFFAOYSA-N 9-benzhydryl-5-cyano-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC=C(C(O)=O)C=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 URPYZYLDIAFPSN-UHFFFAOYSA-N 0.000 claims 2
• IRGUTLGZFCPIJY-UHFFFAOYSA-N 1-(2-hydroxypropan-2-yl)-9H-carbazole-4-carboxamide Chemical compound OC(C)(C)C1=CC=C(C=2C3=CC=CC=C3NC1=2)C(=O)N IRGUTLGZFCPIJY-UHFFFAOYSA-N 0.000 claims 1
• VXUQFEQSTWHBAY-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(1,1-dioxo-1,2-thiazolidin-2-yl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4S(CCC4)(=O)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 VXUQFEQSTWHBAY-UHFFFAOYSA-N 0.000 claims 1
• QCPNFZAGPBTASR-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(1,1-dioxothiazinan-2-yl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4S(CCCC4)(=O)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 QCPNFZAGPBTASR-UHFFFAOYSA-N 0.000 claims 1
• UDYYALMTRRVAJO-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazinan-3-yl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(N3C(OCCC3)=O)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 UDYYALMTRRVAJO-UHFFFAOYSA-N 0.000 claims 1
• HHYRMSDPWBCKTJ-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazolidin-3-yl)-9-(1-phenylethyl)carbazole-4-carboxamide Chemical compound C12=CC=C(N3C(OCC3)=O)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1 HHYRMSDPWBCKTJ-UHFFFAOYSA-N 0.000 claims 1
• WNAFFNIIHISTGI-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-(4-fluorophenyl)ethyl]carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=C(F)C=C1 WNAFFNIIHISTGI-UHFFFAOYSA-N 0.000 claims 1
• OTVLWPXUFAKHPL-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(5,5-dimethyl-2-oxo-1,3-oxazinan-3-yl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC(C)(C)C4)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 OTVLWPXUFAKHPL-UHFFFAOYSA-N 0.000 claims 1
• FQVCQASWDKXILB-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-8-fluoro-9-(1,1,1,7,7,7-hexafluoroheptan-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C(F)=C3N(C(CCC(F)(F)F)CCC(F)(F)F)C2=C1 FQVCQASWDKXILB-UHFFFAOYSA-N 0.000 claims 1
• NICUSSUKCZJGLV-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)methyl]-6-(2-oxo-1,3-oxazinan-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCCC4)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 NICUSSUKCZJGLV-UHFFFAOYSA-N 0.000 claims 1
• ACCVZMBBAIOLNY-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)methyl]-6-(2-oxo-1,3-oxazolidin-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC4)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 ACCVZMBBAIOLNY-UHFFFAOYSA-N 0.000 claims 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
• KTTLBFSCHGIONP-UHFFFAOYSA-N 9-(cyclobutylmethyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC3CCC3)C2=C1 KTTLBFSCHGIONP-UHFFFAOYSA-N 0.000 claims 1
• ORGLQHRQYTXQKQ-UHFFFAOYSA-N 9-(cyclopropylmethyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC3CC3)C2=C1 ORGLQHRQYTXQKQ-UHFFFAOYSA-N 0.000 claims 1
• OTBMIQYZFHXOKD-UHFFFAOYSA-N 9-[(4-chloro-3-fluorophenyl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazolidin-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC4)=O)=CC=C3N(CC=3C=C(F)C(Cl)=CC=3)C2=C1 OTBMIQYZFHXOKD-UHFFFAOYSA-N 0.000 claims 1
• HUWOSYNGKAKOSA-UHFFFAOYSA-N 9-[(4-chlorophenyl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazinan-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCCC4)=O)=CC=C3N(CC=3C=CC(Cl)=CC=3)C2=C1 HUWOSYNGKAKOSA-UHFFFAOYSA-N 0.000 claims 1
• CMUJURIMZQUGIQ-UHFFFAOYSA-N 9-[(4-chlorophenyl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazolidin-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC4)=O)=CC=C3N(CC=3C=CC(Cl)=CC=3)C2=C1 CMUJURIMZQUGIQ-UHFFFAOYSA-N 0.000 claims 1
• JDDODTUKCYCDHF-UHFFFAOYSA-N 9-benzhydryl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(morpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(=O)N4CCOCC4)C=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 JDDODTUKCYCDHF-UHFFFAOYSA-N 0.000 claims 1
• QTKYRZUXRWPKSE-UHFFFAOYSA-N 9-benzhydryl-5-cyano-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC=C(C(N)=O)C=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 QTKYRZUXRWPKSE-UHFFFAOYSA-N 0.000 claims 1
• YROMUCUKXOBKPI-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-oxo-1,3-oxazolidin-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC4)=O)=CC=C3N(CC=3C=CC=CC=3)C2=C1 YROMUCUKXOBKPI-UHFFFAOYSA-N 0.000 claims 1
• ZJBONGFPCPJVNN-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3,3-dimethylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(C)(C)CCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 ZJBONGFPCPJVNN-UHFFFAOYSA-N 0.000 claims 1
• YDZZDCGNQLLQHG-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3,3-dimethylpyrrolidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(C)(C)CC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 YDZZDCGNQLLQHG-UHFFFAOYSA-N 0.000 claims 1
• OZWZRCVKIRKDEX-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-methoxyazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound C1C(OC)CN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 OZWZRCVKIRKDEX-UHFFFAOYSA-N 0.000 claims 1
• MSBAAZCMJRGJOL-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-hydroxy-2-methylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1CC(O)CCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 MSBAAZCMJRGJOL-UHFFFAOYSA-N 0.000 claims 1
• TZHWOSPUDWIACF-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-hydroxy-4-methylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCC(C)(O)CC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 TZHWOSPUDWIACF-UHFFFAOYSA-N 0.000 claims 1
• SEBLTOQDMGLZBT-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(5,5-dimethyl-2-oxo-1,3-oxazinan-3-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N4C(OCC(C)(C)C4)=O)=CC=C3N(CC=3C=CC=CC=3)C2=C1 SEBLTOQDMGLZBT-UHFFFAOYSA-N 0.000 claims 1
• YVBCLIXZALLOLL-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(pyrrolidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCCC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 YVBCLIXZALLOLL-UHFFFAOYSA-N 0.000 claims 1
• HPALTCSDNFKNSS-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-[4-(hydroxymethyl)piperidine-1-carbonyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCC(CO)CC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 HPALTCSDNFKNSS-UHFFFAOYSA-N 0.000 claims 1
• GAWGFAKARWGUIF-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-hydroxycarbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(O)=CC=C3N(CC=3C=CC=CC=3)C2=C1 GAWGFAKARWGUIF-UHFFFAOYSA-N 0.000 claims 1
• HGPJZRHXGJMNGI-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carbonitrile Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC=C(C(C)(C)O)C=C3N(CC=3C=CC=CC=3)C2=C1 HGPJZRHXGJMNGI-UHFFFAOYSA-N 0.000 claims 1
• CPMHHQADTDWUSX-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(CC=3C=CC=CC=3)C2=C1 CPMHHQADTDWUSX-UHFFFAOYSA-N 0.000 claims 1
• PTZNJUNAOWEHHN-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(3-fluorobenzoyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(=O)C=4C=C(F)C=CC=4)C=C3N(CC=3C=CC=CC=3)C2=C1 PTZNJUNAOWEHHN-UHFFFAOYSA-N 0.000 claims 1
• YPLGRNLDKDQPGG-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(morpholine-4-carbonyl)carbazole-4-carbonitrile Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC=C(C(=O)N4CCOCC4)C=C3N(CC=3C=CC=CC=3)C2=C1 YPLGRNLDKDQPGG-UHFFFAOYSA-N 0.000 claims 1
• SFLHWABVURNINR-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(morpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(=O)N4CCOCC4)C=C3N(CC=3C=CC=CC=3)C2=C1 SFLHWABVURNINR-UHFFFAOYSA-N 0.000 claims 1
• VPFZDQAMRYSUKM-UHFFFAOYSA-N 9-benzyl-6-(2,6-dimethylmorpholine-4-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C1C(C)OC(C)CN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 VPFZDQAMRYSUKM-UHFFFAOYSA-N 0.000 claims 1
• MGBUWHZFYVGUBA-UHFFFAOYSA-N 9-benzyl-6-(3,3-difluoropyrrolidine-1-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)(F)CC4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 MGBUWHZFYVGUBA-UHFFFAOYSA-N 0.000 claims 1
• GXLUGNHVZZDUFE-UHFFFAOYSA-N 9-benzyl-6-(3,3-dimethylmorpholine-4-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4C(COCC4)(C)C)=CC=C3N(CC=3C=CC=CC=3)C2=C1 GXLUGNHVZZDUFE-UHFFFAOYSA-N 0.000 claims 1
• UFJRRYGQWOAETH-UHFFFAOYSA-N 9-benzyl-6-(4,4-dimethyl-1,3-oxazolidine-3-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4C(COC4)(C)C)=CC=C3N(CC=3C=CC=CC=3)C2=C1 UFJRRYGQWOAETH-UHFFFAOYSA-N 0.000 claims 1
• YAACYNJZQKJEGK-UHFFFAOYSA-N 9-benzyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)-3-n,3-n-dimethylcarbazole-3,5-dicarboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(C(=O)N(C)C)=CC=C2N1CC1=CC=CC=C1 YAACYNJZQKJEGK-UHFFFAOYSA-N 0.000 claims 1
• CUVRQVVOJOUWBP-UHFFFAOYSA-N CNC(=O)Nc1ccc2n(Cc3ccccc3)c3cc(cc(C(N)=O)c3c2c1)-c1c(C)noc1C.CN(C)C(=O)Nc1ccc2n(Cc3ccccc3)c3cc(cc(C(N)=O)c3c2c1)-c1c(C)noc1C Chemical compound CNC(=O)Nc1ccc2n(Cc3ccccc3)c3cc(cc(C(N)=O)c3c2c1)-c1c(C)noc1C.CN(C)C(=O)Nc1ccc2n(Cc3ccccc3)c3cc(cc(C(N)=O)c3c2c1)-c1c(C)noc1C CUVRQVVOJOUWBP-UHFFFAOYSA-N 0.000 claims 1
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 84
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 857
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 349
• 229910052796 boron Inorganic materials 0.000 description 253
• 239000002245 particle Substances 0.000 description 175
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 156
• 239000005695 Ammonium acetate Substances 0.000 description 156
• 235000019257 ammonium acetate Nutrition 0.000 description 156
• 229940043376 ammonium acetate Drugs 0.000 description 156
• 230000014759 maintenance of location Effects 0.000 description 143
• 238000006243 chemical reaction Methods 0.000 description 111
• 238000004128 high performance liquid chromatography Methods 0.000 description 99
• 239000000047 product Substances 0.000 description 68
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 239000000523 sample Substances 0.000 description 65
• 239000011541 reaction mixture Substances 0.000 description 60
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
• 239000007787 solid Substances 0.000 description 41
• 206010065042 Immune reconstitution inflammatory syndrome Diseases 0.000 description 35
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
• 239000000538 analytical sample Substances 0.000 description 31
• 239000003814 drug Substances 0.000 description 31
• 238000004458 analytical method Methods 0.000 description 29
• 125000005843 halogen group Chemical group 0.000 description 29
• 239000002244 precipitate Substances 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
• 238000002953 preparative HPLC Methods 0.000 description 26
• 239000013058 crude material Substances 0.000 description 25
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 25
• 239000000126 substance Substances 0.000 description 24
• 125000001424 substituent group Chemical group 0.000 description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• 239000000243 solution Substances 0.000 description 19
• 238000003756 stirring Methods 0.000 description 19
• 229940124597 therapeutic agent Drugs 0.000 description 17
• 239000004480 active ingredient Substances 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000002552 dosage form Substances 0.000 description 15
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 14
• 229940079593 drug Drugs 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• 125000003118 aryl group Chemical group 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 11
• 108090000623 proteins and genes Proteins 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
• 238000010521 absorption reaction Methods 0.000 description 10
• 125000004429 atom Chemical group 0.000 description 10
• CVLHETBAROWASE-UHFFFAOYSA-N 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole Chemical compound CC1=NOC(C)=C1B1OC(C)(C)C(C)(C)O1 CVLHETBAROWASE-UHFFFAOYSA-N 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• 230000001154 acute effect Effects 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 239000003153 chemical reaction reagent Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
• 230000001363 autoimmune Effects 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 208000011580 syndromic disease Diseases 0.000 description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
• QUHVRXKSQHIZNV-UHFFFAOYSA-N 3,3-difluoroazetidine Chemical compound FC1(F)CNC1 QUHVRXKSQHIZNV-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 235000019441 ethanol Nutrition 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 229920001223 polyethylene glycol Polymers 0.000 description 7
• 239000000651 prodrug Substances 0.000 description 7
• 229940002612 prodrug Drugs 0.000 description 7
• 235000018102 proteins Nutrition 0.000 description 7
• 102000004169 proteins and genes Human genes 0.000 description 7
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 7
• 239000012453 solvate Substances 0.000 description 7
• 210000001519 tissue Anatomy 0.000 description 7
• NECCZNKVXWUJSU-UHFFFAOYSA-N 7-(3,5-dimethyl-1,2-oxazol-4-yl)-5-(methylcarbamoyl)-9h-carbazole-3-carboxylic acid Chemical compound C=1C=2NC3=CC=C(C(O)=O)C=C3C=2C(C(=O)NC)=CC=1C=1C(C)=NOC=1C NECCZNKVXWUJSU-UHFFFAOYSA-N 0.000 description 6
• 208000023275 Autoimmune disease Diseases 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 108020004414 DNA Proteins 0.000 description 6
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• 238000005481 NMR spectroscopy Methods 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
• 125000003710 aryl alkyl group Chemical group 0.000 description 6
• 150000001721 carbon Chemical group 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 239000006071 cream Substances 0.000 description 6
• FLFRMHNWAJYNKT-UHFFFAOYSA-N ethyl 7-(3,5-dimethyl-1,2-oxazol-4-yl)-5-(methylcarbamoyl)-9h-carbazole-3-carboxylate Chemical compound C=1C(C(=O)NC)=C2C3=CC(C(=O)OCC)=CC=C3NC2=CC=1C=1C(C)=NOC=1C FLFRMHNWAJYNKT-UHFFFAOYSA-N 0.000 description 6
• OIINFWIVDSHFRI-UHFFFAOYSA-N ethyl 7-bromo-5-(methylcarbamoyl)-9h-carbazole-3-carboxylate Chemical compound BrC1=CC(C(=O)NC)=C2C3=CC(C(=O)OCC)=CC=C3NC2=C1 OIINFWIVDSHFRI-UHFFFAOYSA-N 0.000 description 6
• 125000001188 haloalkyl group Chemical group 0.000 description 6
• 125000002950 monocyclic group Chemical group 0.000 description 6
• 235000019198 oils Nutrition 0.000 description 6
• 210000000056 organ Anatomy 0.000 description 6
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• MWXFYMWMYQVUFV-UHFFFAOYSA-N 1-methyl-9h-carbazole-4-carboxamide Chemical compound C12=CC=CC=C2NC2=C1C(C(N)=O)=CC=C2C MWXFYMWMYQVUFV-UHFFFAOYSA-N 0.000 description 5
• CLMZIIBDLUBGAO-UHFFFAOYSA-N 2-bromo-6-ethoxycarbonyl-6,7,8,9-tetrahydro-5h-carbazole-4-carboxylic acid Chemical compound N1C2=CC(Br)=CC(C(O)=O)=C2C2=C1CCC(C(=O)OCC)C2 CLMZIIBDLUBGAO-UHFFFAOYSA-N 0.000 description 5
• IKPHDTJLQXQOKU-UHFFFAOYSA-N 5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazole-3-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(O)=O)=CC=C3NC2=C1 IKPHDTJLQXQOKU-UHFFFAOYSA-N 0.000 description 5
• XPEAUZOUDXBJDP-UHFFFAOYSA-N 7-bromo-5-carbamoyl-9h-carbazole-3-carboxylic acid Chemical compound N1C2=CC=C(C(O)=O)C=C2C2=C1C=C(Br)C=C2C(=O)N XPEAUZOUDXBJDP-UHFFFAOYSA-N 0.000 description 5
• 201000009030 Carcinoma Diseases 0.000 description 5
• 108010010803 Gelatin Proteins 0.000 description 5
• 108010033040 Histones Proteins 0.000 description 5
• 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 5
• 241001465754 Metazoa Species 0.000 description 5
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
• 229930006000 Sucrose Natural products 0.000 description 5
• 239000004809 Teflon Substances 0.000 description 5
• 229920006362 Teflon® Polymers 0.000 description 5
• 239000003963 antioxidant agent Substances 0.000 description 5
• 235000006708 antioxidants Nutrition 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 5
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• IDENNJNCLJGWNZ-UHFFFAOYSA-N ethyl 7-bromo-5-carbamoyl-9h-carbazole-3-carboxylate Chemical compound BrC1=CC(C(N)=O)=C2C3=CC(C(=O)OCC)=CC=C3NC2=C1 IDENNJNCLJGWNZ-UHFFFAOYSA-N 0.000 description 5
• 239000008273 gelatin Substances 0.000 description 5
• 229920000159 gelatin Polymers 0.000 description 5
• 235000019322 gelatine Nutrition 0.000 description 5
• 235000011852 gelatine desserts Nutrition 0.000 description 5
• 235000011187 glycerol Nutrition 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 125000001041 indolyl group Chemical group 0.000 description 5
• 208000015181 infectious disease Diseases 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• 239000012528 membrane Substances 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• 239000003755 preservative agent Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000005720 sucrose Substances 0.000 description 5
• 239000000454 talc Substances 0.000 description 5
• 235000012222 talc Nutrition 0.000 description 5
• 229910052623 talc Inorganic materials 0.000 description 5
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 4
• LZZKIQKOKQGHGT-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9h-carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3NC2=C1 LZZKIQKOKQGHGT-UHFFFAOYSA-N 0.000 description 4
• MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 4
• CXEWSLNGXJEZBZ-UHFFFAOYSA-N 5-bromo-9h-carbazole-3-carboxylic acid Chemical compound C1=CC(Br)=C2C3=CC(C(=O)O)=CC=C3NC2=C1 CXEWSLNGXJEZBZ-UHFFFAOYSA-N 0.000 description 4
• KKKTWWNRNXEFDE-UHFFFAOYSA-N 5-o-tert-butyl 3-o-ethyl 7-bromo-9h-carbazole-3,5-dicarboxylate Chemical compound BrC1=CC(C(=O)OC(C)(C)C)=C2C3=CC(C(=O)OCC)=CC=C3NC2=C1 KKKTWWNRNXEFDE-UHFFFAOYSA-N 0.000 description 4
• HXFZAFYRMDVGPB-UHFFFAOYSA-N 7-bromo-9h-carbazole-3-carboxylic acid Chemical compound BrC1=CC=C2C3=CC(C(=O)O)=CC=C3NC2=C1 HXFZAFYRMDVGPB-UHFFFAOYSA-N 0.000 description 4
• KBBSCYFCPCQBDO-UHFFFAOYSA-N 9-[(4-fluorophenyl)methyl]-6-(morpholine-4-carbonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole-4-carboxamide Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CCOCC4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 KBBSCYFCPCQBDO-UHFFFAOYSA-N 0.000 description 4
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
• 241000416162 Astragalus gummifer Species 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• 239000002202 Polyethylene glycol Substances 0.000 description 4
• 206010040047 Sepsis Diseases 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• 229920001615 Tragacanth Polymers 0.000 description 4
• 241000382509 Vania Species 0.000 description 4
• 206010047115 Vasculitis Diseases 0.000 description 4
• UDSATNPOXGAFKY-OKILXGFUSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(NC=2C3=CC=C(C=2)C2=C(ON=C2C)C)C3=C1 UDSATNPOXGAFKY-OKILXGFUSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• 238000007796 conventional method Methods 0.000 description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 description 4
• 208000035475 disorder Diseases 0.000 description 4
• 239000003995 emulsifying agent Substances 0.000 description 4
• 230000001973 epigenetic effect Effects 0.000 description 4
• IYQUGFFQBMETBI-UHFFFAOYSA-N ethyl 7-bromo-5-(methylcarbamoyl)-2,3,4,9-tetrahydro-1h-carbazole-3-carboxylate Chemical compound N1C2=CC(Br)=CC(C(=O)NC)=C2C2=C1CCC(C(=O)OCC)C2 IYQUGFFQBMETBI-UHFFFAOYSA-N 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 239000000499 gel Substances 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 150000004820 halides Chemical class 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 239000000314 lubricant Substances 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 239000005416 organic matter Substances 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 238000007911 parenteral administration Methods 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 229920000642 polymer Polymers 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 239000000829 suppository Substances 0.000 description 4
• 125000001544 thienyl group Chemical group 0.000 description 4
• 235000010487 tragacanth Nutrition 0.000 description 4
• 239000000196 tragacanth Substances 0.000 description 4
• 229940116362 tragacanth Drugs 0.000 description 4
• 230000009385 viral infection Effects 0.000 description 4
• 239000001993 wax Substances 0.000 description 4
• HTGAJOIMYCWJSZ-UHFFFAOYSA-N (4-methoxyphenyl)methyl n-(9-benzyl-7-bromo-5-carbamoylcarbazol-3-yl)carbamate Chemical compound C1=CC(OC)=CC=C1COC(=O)NC1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(Br)C=2)C3=C1 HTGAJOIMYCWJSZ-UHFFFAOYSA-N 0.000 description 3
• GJLZVUJWBUHSQU-TXEJJXNPSA-N (5-bromo-9h-carbazol-3-yl)-[(2s,6r)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(NC=2C3=C(Br)C=CC=2)C3=C1 GJLZVUJWBUHSQU-TXEJJXNPSA-N 0.000 description 3
• QWWOSPADDBTKTP-UHFFFAOYSA-N (5-bromo-9h-carbazol-3-yl)-morpholin-4-ylmethanone Chemical compound C1=C2C=3C(Br)=CC=CC=3NC2=CC=C1C(=O)N1CCOCC1 QWWOSPADDBTKTP-UHFFFAOYSA-N 0.000 description 3
• LFVVIWSJMUTQQD-TXEJJXNPSA-N (7-bromo-9h-carbazol-3-yl)-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(NC=2C3=CC=C(Br)C=2)C3=C1 LFVVIWSJMUTQQD-TXEJJXNPSA-N 0.000 description 3
• LQCOMZKCSSMCJC-UHFFFAOYSA-N (7-bromo-9h-carbazol-3-yl)-morpholin-4-ylmethanone Chemical compound C=1C(Br)=CC=C(C2=C3)C=1NC2=CC=C3C(=O)N1CCOCC1 LQCOMZKCSSMCJC-UHFFFAOYSA-N 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-UHFFFAOYSA-N 0.000 description 3
• IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 3
• VJZTXFBNASSRLH-PHIMTYICSA-N 2-bromo-6-[(2r,6s)-2,6-dimethylmorpholine-4-carbonyl]-9h-carbazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(NC=2C3=C(C(N)=O)C=C(Br)C=2)C3=C1 VJZTXFBNASSRLH-PHIMTYICSA-N 0.000 description 3
• NOGOHHYGEWJMBZ-UHFFFAOYSA-N 2-bromo-9-[(4-fluorophenyl)methyl]-6-(morpholine-4-carbonyl)carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CCOCC3)C=C2C=2C(C(=O)N)=CC(Br)=CC=2N1CC1=CC=C(F)C=C1 NOGOHHYGEWJMBZ-UHFFFAOYSA-N 0.000 description 3
• PNDSVDVGTHGUHU-UHFFFAOYSA-N 5-o-tert-butyl 3-o-ethyl 7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)methyl]carbazole-3,5-dicarboxylate Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(=O)OC(C)(C)C)=C2C2=CC(C(=O)OCC)=CC=C2N1CC1=CC=C(F)C=C1 PNDSVDVGTHGUHU-UHFFFAOYSA-N 0.000 description 3
• ZZNFOVXHSCZSLK-UHFFFAOYSA-N 6-(3,3-difluoroazetidine-1-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)(F)C4)=CC=C3NC2=C1 ZZNFOVXHSCZSLK-UHFFFAOYSA-N 0.000 description 3
• PDRUTGGGRYVTKP-UHFFFAOYSA-N 6-amino-2-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(N)=CC=C3NC2=C1 PDRUTGGGRYVTKP-UHFFFAOYSA-N 0.000 description 3
• NSNKLUNJXLGUFY-UHFFFAOYSA-N 7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)methyl]-5-[(2-methylpropan-2-yl)oxycarbonyl]carbazole-3-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C(=O)OC(C)(C)C)=C2C3=CC(C(O)=O)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 NSNKLUNJXLGUFY-UHFFFAOYSA-N 0.000 description 3
• IKZMTODEXIPNJD-UHFFFAOYSA-N 9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-3-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(O)=O)=CC=C3N(CC=3C=CC=CC=3)C2=C1 IKZMTODEXIPNJD-UHFFFAOYSA-N 0.000 description 3
• VKNXXXMJOZKRKY-UHFFFAOYSA-N 9-benzyl-7-bromo-5-carbamoylcarbazole-3-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2C=2C(C(=O)N)=CC(Br)=CC=2N1CC1=CC=CC=C1 VKNXXXMJOZKRKY-UHFFFAOYSA-N 0.000 description 3
• 229920001817 Agar Polymers 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 108010077544 Chromatin Proteins 0.000 description 3
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
• 208000009889 Herpes Simplex Diseases 0.000 description 3
• 208000007514 Herpes zoster Diseases 0.000 description 3
• 102000006947 Histones Human genes 0.000 description 3
• 206010061218 Inflammation Diseases 0.000 description 3
• 208000010718 Multiple Organ Failure Diseases 0.000 description 3
• 239000004677 Nylon Substances 0.000 description 3
• 229920002732 Polyanhydride Polymers 0.000 description 3
• 206010040070 Septic Shock Diseases 0.000 description 3
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
• 208000036142 Viral infection Diseases 0.000 description 3
• 241000700605 Viruses Species 0.000 description 3
• XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
• UHLVPBAYHDHLIU-OKILXGFUSA-N [(2r,6s)-2,6-dimethylmorpholin-4-yl]-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(NC=2C3=C(C4=C(ON=C4C)C)C=CC=2)C3=C1 UHLVPBAYHDHLIU-OKILXGFUSA-N 0.000 description 3
• ZWCSKIACDITOHO-GASCZTMLSA-N [(2s,6r)-2,6-dimethylmorpholin-4-yl]-[7-(3,5-dimethyl-1,2-oxazol-4-yl)-9-methylsulfonylcarbazol-3-yl]methanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(C=2C3=CC=C(C=2)C2=C(ON=C2C)C)S(C)(=O)=O)C3=C1 ZWCSKIACDITOHO-GASCZTMLSA-N 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 235000010419 agar Nutrition 0.000 description 3
• 235000010443 alginic acid Nutrition 0.000 description 3
• 229920000615 alginic acid Polymers 0.000 description 3
• 150000004781 alginic acids Chemical class 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 3
• 125000000304 alkynyl group Chemical group 0.000 description 3
• 125000006242 amine protecting group Chemical group 0.000 description 3
• 150000001448 anilines Chemical class 0.000 description 3
• 230000006907 apoptotic process Effects 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• 235000012216 bentonite Nutrition 0.000 description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
• 239000001768 carboxy methyl cellulose Substances 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 235000010980 cellulose Nutrition 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 239000001913 cellulose Substances 0.000 description 3
• 210000003483 chromatin Anatomy 0.000 description 3
• 230000001684 chronic effect Effects 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
• 238000002648 combination therapy Methods 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 230000007547 defect Effects 0.000 description 3
• 230000003111 delayed effect Effects 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• NODAUOCVJATSCH-UHFFFAOYSA-N ethyl 5-bromo-9h-carbazole-3-carboxylate Chemical compound C1=CC(Br)=C2C3=CC(C(=O)OCC)=CC=C3NC2=C1 NODAUOCVJATSCH-UHFFFAOYSA-N 0.000 description 3
• HLZXXHHQJUJQGC-UHFFFAOYSA-N ethyl 5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazole-3-carboxylate Chemical compound C=1C(C(N)=O)=C2C3=CC(C(=O)OCC)=CC=C3NC2=CC=1C=1C(C)=NOC=1C HLZXXHHQJUJQGC-UHFFFAOYSA-N 0.000 description 3
• GDYONEWVNVFGBR-UHFFFAOYSA-N ethyl 7-bromo-2,3,4,9-tetrahydro-1h-carbazole-3-carboxylate Chemical compound N1C2=CC(Br)=CC=C2C2=C1CCC(C(=O)OCC)C2 GDYONEWVNVFGBR-UHFFFAOYSA-N 0.000 description 3
• KQHASAOBQMGBLE-UHFFFAOYSA-N ethyl 7-bromo-5-carbamoyl-2,3,4,9-tetrahydro-1h-carbazole-3-carboxylate Chemical compound N1C2=CC(Br)=CC(C(N)=O)=C2C2=C1CCC(C(=O)OCC)C2 KQHASAOBQMGBLE-UHFFFAOYSA-N 0.000 description 3
• GWBCTTUZQZJRAJ-UHFFFAOYSA-N ethyl 7-bromo-9h-carbazole-3-carboxylate Chemical compound BrC1=CC=C2C3=CC(C(=O)OCC)=CC=C3NC2=C1 GWBCTTUZQZJRAJ-UHFFFAOYSA-N 0.000 description 3
• MMRRVBYUMUZNII-UHFFFAOYSA-N ethyl 9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-3-carboxylate Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(C(=O)OCC)=CC=C2N1CC1=CC=CC=C1 MMRRVBYUMUZNII-UHFFFAOYSA-N 0.000 description 3
• 239000000945 filler Substances 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 239000006260 foam Substances 0.000 description 3
• 230000006870 function Effects 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 125000002541 furyl group Chemical group 0.000 description 3
• 229940093915 gynecological organic acid Drugs 0.000 description 3
• 125000004438 haloalkoxy group Chemical group 0.000 description 3
• 208000006454 hepatitis Diseases 0.000 description 3
• 231100000283 hepatitis Toxicity 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
• 125000002883 imidazolyl group Chemical group 0.000 description 3
• 239000003701 inert diluent Substances 0.000 description 3
• 208000027866 inflammatory disease Diseases 0.000 description 3
• 230000004054 inflammatory process Effects 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
• 239000002502 liposome Substances 0.000 description 3
• 239000008297 liquid dosage form Substances 0.000 description 3
• 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 3
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 238000000465 moulding Methods 0.000 description 3
• 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 3
• 208000020588 necrotizing soft tissue infection Diseases 0.000 description 3
• 239000012457 nonaqueous media Substances 0.000 description 3
• 229920001778 nylon Polymers 0.000 description 3
• 239000002674 ointment Substances 0.000 description 3
• 239000004006 olive oil Substances 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 235000005985 organic acids Nutrition 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 229910000160 potassium phosphate Inorganic materials 0.000 description 3
• 235000011009 potassium phosphates Nutrition 0.000 description 3
• 229960004063 propylene glycol Drugs 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 description 3
• 238000001959 radiotherapy Methods 0.000 description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 description 3
• 235000012239 silicon dioxide Nutrition 0.000 description 3
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
• 235000010356 sorbitol Nutrition 0.000 description 3
• 239000000600 sorbitol Substances 0.000 description 3
• 239000007921 spray Substances 0.000 description 3
• KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 3
• 229910000080 stannane Inorganic materials 0.000 description 3
• 235000000346 sugar Nutrition 0.000 description 3
• 150000008163 sugars Chemical class 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• 239000000375 suspending agent Substances 0.000 description 3
• 238000001308 synthesis method Methods 0.000 description 3
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 3
• PVAODRASMNGWIC-UHFFFAOYSA-N tert-butyl 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxylate Chemical compound CC1=NOC(C)=C1C1=CC(C(=O)OC(C)(C)C)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 PVAODRASMNGWIC-UHFFFAOYSA-N 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 125000000335 thiazolyl group Chemical group 0.000 description 3
• 230000000699 topical effect Effects 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
• HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 2
• RQJPWNPMAJXYRQ-UHFFFAOYSA-N (4-methoxyphenyl)methyl n-(9-benzyl-7-bromo-5-carbamoylcarbazol-3-yl)-n-methylcarbamate Chemical compound C1=CC(OC)=CC=C1COC(=O)N(C)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(Br)C=2)C3=C1 RQJPWNPMAJXYRQ-UHFFFAOYSA-N 0.000 description 2
• AXTPVVSCKQJRHP-UHFFFAOYSA-N (4-methoxyphenyl)methyl n-[5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazol-3-yl]carbamate Chemical compound C1=CC(OC)=CC=C1COC(=O)NC1=CC=C(NC=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 AXTPVVSCKQJRHP-UHFFFAOYSA-N 0.000 description 2
• KVJMBQNKYSXKGL-UHFFFAOYSA-N (4-methoxyphenyl)methyl n-[9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]carbamate Chemical compound C1=CC(OC)=CC=C1COC(=O)NC1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 KVJMBQNKYSXKGL-UHFFFAOYSA-N 0.000 description 2
• JTLAIKFGRHDNQM-UHFFFAOYSA-N 1-bromo-2-fluoroethane Chemical compound FCCBr JTLAIKFGRHDNQM-UHFFFAOYSA-N 0.000 description 2
• CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
• 125000005955 1H-indazolyl group Chemical group 0.000 description 2
• XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 2
• IWMWNSHHWITAMT-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(4-fluorophenyl)methyl]carbazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C(O)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=CC(F)=CC=3)C2=C1 IWMWNSHHWITAMT-UHFFFAOYSA-N 0.000 description 2
• HNXIMTFHRGHUHY-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-(4,4,4-trifluoro-1-pyridin-2-ylbutyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(CCC(F)(F)F)C=3N=CC=CC=3)C2=C1 HNXIMTFHRGHUHY-UHFFFAOYSA-N 0.000 description 2
• GXOJFGNCOHQOIG-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[(3-methoxyphenyl)-(oxan-4-yl)methyl]carbazole-4-carboxamide Chemical compound COC1=CC=CC(C(C2CCOCC2)N2C3=CC(=CC(=C3C3=CC=C(C=C32)C(C)(C)O)C(N)=O)C2=C(ON=C2C)C)=C1 GXOJFGNCOHQOIG-UHFFFAOYSA-N 0.000 description 2
• QDNKGFASTDKESA-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[(4-methoxyphenyl)-(oxan-4-yl)methyl]carbazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C(N1C2=CC(=CC(=C2C2=CC=C(C=C21)C(C)(C)O)C(N)=O)C1=C(ON=C1C)C)C1CCOCC1 QDNKGFASTDKESA-UHFFFAOYSA-N 0.000 description 2
• BDEPUTYZLQHUPC-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)-9-[oxan-4-yl-(2,4,6-trifluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C3CCOCC3)C=3C(=CC(F)=CC=3F)F)C2=C1 BDEPUTYZLQHUPC-UHFFFAOYSA-N 0.000 description 2
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
• OLMHJFBVMFYZKW-UHFFFAOYSA-N 2-bromo-6-(morpholine-4-carbonyl)-9h-carbazole-4-carboxamide Chemical compound C1=C2C=3C(C(=O)N)=CC(Br)=CC=3NC2=CC=C1C(=O)N1CCOCC1 OLMHJFBVMFYZKW-UHFFFAOYSA-N 0.000 description 2
• YQCBOALVDSATLC-UHFFFAOYSA-N 3-bromo-5-hydrazinylbenzoic acid;dihydrochloride Chemical compound Cl.Cl.NNC1=CC(Br)=CC(C(O)=O)=C1 YQCBOALVDSATLC-UHFFFAOYSA-N 0.000 description 2
• WQYAZBFZFIUIPL-UHFFFAOYSA-N 3-fluoroazetidine Chemical compound FC1CNC1 WQYAZBFZFIUIPL-UHFFFAOYSA-N 0.000 description 2
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 2
• NFLDXKDDDKVRSN-UHFFFAOYSA-N 4-iodo-5-methyl-1,2-oxazole Chemical compound CC=1ON=CC=1I NFLDXKDDDKVRSN-UHFFFAOYSA-N 0.000 description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
• LODJSNIBONUPOY-UHFFFAOYSA-N 5-o-tert-butyl 3-o-ethyl 7-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazole-3,5-dicarboxylate Chemical compound C=1C(C(=O)OC(C)(C)C)=C2C3=CC(C(=O)OCC)=CC=C3NC2=CC=1C=1C(C)=NOC=1C LODJSNIBONUPOY-UHFFFAOYSA-N 0.000 description 2
• VNDKSBIVAMQISP-CALCHBBNSA-N 9-(cyclobutylmethyl)-6-[(2s,6r)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC2CCC2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 VNDKSBIVAMQISP-CALCHBBNSA-N 0.000 description 2
• RINFCFCAVYTZNQ-UHFFFAOYSA-N 9-[(2,4-difluorophenyl)-(oxan-4-yl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C3CCOCC3)C=3C(=CC(F)=CC=3)F)C2=C1 RINFCFCAVYTZNQ-UHFFFAOYSA-N 0.000 description 2
• OCPGYHUYULDYFQ-UHFFFAOYSA-N 9-[(2,6-difluorophenyl)-(oxan-4-yl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(C3CCOCC3)C=3C(=CC=CC=3F)F)C2=C1 OCPGYHUYULDYFQ-UHFFFAOYSA-N 0.000 description 2
• WMGWRRMNUPHOTQ-UHFFFAOYSA-N 9-[1-(2-chlorophenyl)-4,4,4-trifluorobutyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC=C(C(C)(C)O)C=C3N(C(CCC(F)(F)F)C=3C(=CC=CC=3)Cl)C2=C1 WMGWRRMNUPHOTQ-UHFFFAOYSA-N 0.000 description 2
• UDEWALWSJAHDCT-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(methylcarbamoylamino)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(NC(=O)NC)=CC=C2N1CC1=CC=CC=C1 UDEWALWSJAHDCT-UHFFFAOYSA-N 0.000 description 2
• 244000215068 Acacia senegal Species 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• 208000026872 Addison Disease Diseases 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 206010003445 Ascites 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
• 201000001320 Atherosclerosis Diseases 0.000 description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 2
• 208000033222 Biliary cirrhosis primary Diseases 0.000 description 2
• 206010005003 Bladder cancer Diseases 0.000 description 2
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
• 208000003174 Brain Neoplasms Diseases 0.000 description 2
• 206010006187 Breast cancer Diseases 0.000 description 2
• 208000026310 Breast neoplasm Diseases 0.000 description 2
• 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
• NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 2
• 238000005600 Cadogan reaction Methods 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• 206010008609 Cholangitis sclerosing Diseases 0.000 description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
• 201000004624 Dermatitis Diseases 0.000 description 2
• 102100027094 Echinoderm microtubule-associated protein-like 1 Human genes 0.000 description 2
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
• 208000037487 Endotoxemia Diseases 0.000 description 2
• 239000001856 Ethyl cellulose Substances 0.000 description 2
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
• 241000206672 Gelidium Species 0.000 description 2
• 208000007465 Giant cell arteritis Diseases 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• 201000005569 Gout Diseases 0.000 description 2
• 229920000084 Gum arabic Polymers 0.000 description 2
• 208000032843 Hemorrhage Diseases 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 101001057941 Homo sapiens Echinoderm microtubule-associated protein-like 1 Proteins 0.000 description 2
• 241000701806 Human papillomavirus Species 0.000 description 2
• 206010020751 Hypersensitivity Diseases 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• 229930195725 Mannitol Natural products 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 208000034486 Multi-organ failure Diseases 0.000 description 2
• 101000653787 Mus musculus Protein S100-A11 Proteins 0.000 description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
• 108010047956 Nucleosomes Proteins 0.000 description 2
• 206010033128 Ovarian cancer Diseases 0.000 description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 description 2
• 206010033645 Pancreatitis Diseases 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• 208000012654 Primary biliary cholangitis Diseases 0.000 description 2
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
• ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
• 206010063837 Reperfusion injury Diseases 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 235000021355 Stearic acid Nutrition 0.000 description 2
• 238000006069 Suzuki reaction reaction Methods 0.000 description 2
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 2
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 2
• 241000700647 Variola virus Species 0.000 description 2
• ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
• ZRFCJMXCGWOZBV-UHFFFAOYSA-N [5-(3,5-dimethyl-1,2-oxazol-4-yl)-9h-carbazol-3-yl]-morpholin-4-ylmethanone Chemical compound CC1=NOC(C)=C1C1=CC=CC2=C1C1=CC(C(=O)N3CCOCC3)=CC=C1N2 ZRFCJMXCGWOZBV-UHFFFAOYSA-N 0.000 description 2
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
• 235000010489 acacia gum Nutrition 0.000 description 2
• 239000000205 acacia gum Substances 0.000 description 2
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
• 239000012346 acetyl chloride Substances 0.000 description 2
• 206010069351 acute lung injury Diseases 0.000 description 2
• 238000007792 addition Methods 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 239000000783 alginic acid Substances 0.000 description 2
• 229960001126 alginic acid Drugs 0.000 description 2
• 125000005236 alkanoylamino group Chemical group 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 208000030961 allergic reaction Diseases 0.000 description 2
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 230000000259 anti-tumor effect Effects 0.000 description 2
• 125000001769 aryl amino group Chemical group 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 229920002988 biodegradable polymer Polymers 0.000 description 2
• 239000004621 biodegradable polymer Substances 0.000 description 2
• 230000033228 biological regulation Effects 0.000 description 2
• 235000010290 biphenyl Nutrition 0.000 description 2
• 239000004305 biphenyl Substances 0.000 description 2
• 208000034158 bleeding Diseases 0.000 description 2
• 230000000740 bleeding effect Effects 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 239000006172 buffering agent Substances 0.000 description 2
• YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 description 2
• 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
• 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 150000001716 carbazoles Chemical class 0.000 description 2
• 239000012876 carrier material Substances 0.000 description 2
• 230000022131 cell cycle Effects 0.000 description 2
• 230000032823 cell division Effects 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 238000004296 chiral HPLC Methods 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 2
• 239000011248 coating agent Substances 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 238000013270 controlled release Methods 0.000 description 2
• 235000012343 cottonseed oil Nutrition 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 239000000824 cytostatic agent Substances 0.000 description 2
• 230000001085 cytostatic effect Effects 0.000 description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
• 229910001873 dinitrogen Inorganic materials 0.000 description 2
• 239000002270 dispersing agent Substances 0.000 description 2
• 238000004090 dissolution Methods 0.000 description 2
• 239000008298 dragée Substances 0.000 description 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
• APSIYLUMWKSJOJ-UHFFFAOYSA-N ethyl 5-bromo-2,3,4,9-tetrahydro-1h-carbazole-3-carboxylate Chemical compound N1C2=CC=CC(Br)=C2C2=C1CCC(C(=O)OCC)C2 APSIYLUMWKSJOJ-UHFFFAOYSA-N 0.000 description 2
• 235000019325 ethyl cellulose Nutrition 0.000 description 2
• 229920001249 ethyl cellulose Polymers 0.000 description 2
• MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
• 229940093471 ethyl oleate Drugs 0.000 description 2
• 239000012065 filter cake Substances 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 230000002440 hepatic effect Effects 0.000 description 2
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 150000004679 hydroxides Chemical class 0.000 description 2
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
• 210000000987 immune system Anatomy 0.000 description 2
• 230000006872 improvement Effects 0.000 description 2
• 230000001965 increasing effect Effects 0.000 description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
• 238000006919 indolization reaction Methods 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 238000010253 intravenous injection Methods 0.000 description 2
• 230000007794 irritation Effects 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
• 125000001786 isothiazolyl group Chemical group 0.000 description 2
• 201000005264 laryngeal carcinoma Diseases 0.000 description 2
• 235000010445 lecithin Nutrition 0.000 description 2
• 239000000787 lecithin Substances 0.000 description 2
• 229940067606 lecithin Drugs 0.000 description 2
• 208000032839 leukemia Diseases 0.000 description 2
• 239000007937 lozenge Substances 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 201000004792 malaria Diseases 0.000 description 2
• 239000000594 mannitol Substances 0.000 description 2
• 235000010355 mannitol Nutrition 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 239000011159 matrix material Substances 0.000 description 2
• 239000002609 medium Substances 0.000 description 2
• 210000004379 membrane Anatomy 0.000 description 2
• 239000004530 micro-emulsion Substances 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• 239000002808 molecular sieve Substances 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 201000006417 multiple sclerosis Diseases 0.000 description 2
• 201000008383 nephritis Diseases 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 210000001623 nucleosome Anatomy 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 230000036961 partial effect Effects 0.000 description 2
• 230000035515 penetration Effects 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 239000002574 poison Substances 0.000 description 2
• 231100000614 poison Toxicity 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 229920000728 polyester Polymers 0.000 description 2
• 229920005862 polyol Polymers 0.000 description 2
• 150000003077 polyols Chemical class 0.000 description 2
• 230000008092 positive effect Effects 0.000 description 2
• 230000002980 postoperative effect Effects 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 229920001592 potato starch Polymers 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 239000003380 propellant Substances 0.000 description 2
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• 125000002098 pyridazinyl group Chemical group 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
• 238000007363 ring formation reaction Methods 0.000 description 2
• 238000002390 rotary evaporation Methods 0.000 description 2
• FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
• 238000007127 saponification reaction Methods 0.000 description 2
• 208000010157 sclerosing cholangitis Diseases 0.000 description 2
• 230000036303 septic shock Effects 0.000 description 2
• 239000008159 sesame oil Substances 0.000 description 2
• 235000011803 sesame oil Nutrition 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
• 239000007909 solid dosage form Substances 0.000 description 2
• 239000008247 solid mixture Substances 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 229940032147 starch Drugs 0.000 description 2
• 239000008117 stearic acid Substances 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• 206010043207 temporal arteritis Diseases 0.000 description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
• 150000003573 thiols Chemical class 0.000 description 2
• 206010043778 thyroiditis Diseases 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 238000013518 transcription Methods 0.000 description 2
• 230000035897 transcription Effects 0.000 description 2
• 125000004306 triazinyl group Chemical group 0.000 description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
• PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 2
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 201000005112 urinary bladder cancer Diseases 0.000 description 2
• 229910052720 vanadium Inorganic materials 0.000 description 2
• 239000003039 volatile agent Substances 0.000 description 2
• XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
• QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
• FTMXVDOMPAZWLQ-KNVOCYPGSA-N (2s,6r)-2,6-dimethylmorpholine-4-carbaldehyde Chemical compound C[C@H]1CN(C=O)C[C@@H](C)O1 FTMXVDOMPAZWLQ-KNVOCYPGSA-N 0.000 description 1
• RPYIPFXHIKXRKS-UHFFFAOYSA-N (3-bromophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Br)=C1 RPYIPFXHIKXRKS-UHFFFAOYSA-N 0.000 description 1
• HIJADFPYXYQMJD-UHFFFAOYSA-N (3-chloro-2,2-dimethylpropyl) carbonochloridate Chemical compound ClCC(C)(C)COC(Cl)=O HIJADFPYXYQMJD-UHFFFAOYSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• QXERRSGVWWTRDJ-UHFFFAOYSA-N (4-methoxyphenyl)methyl n-[9-benzyl-5-carbamoyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazol-3-yl]-n-methylcarbamate Chemical compound C1=CC(OC)=CC=C1COC(=O)N(C)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 QXERRSGVWWTRDJ-UHFFFAOYSA-N 0.000 description 1
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
• GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
• NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• PCROQKOTNKCDOP-UHFFFAOYSA-N 1-(3,5-dimethyl-1,2-oxazol-4-yl)-9-[(4-fluorophenyl)-(oxan-4-yl)methyl]-7-(2-hydroxypropan-2-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(N)=O)C2=C1N(C(C1CCOCC1)C=1C=CC(F)=CC=1)C1=CC(C(C)(C)O)=CC=C12 PCROQKOTNKCDOP-UHFFFAOYSA-N 0.000 description 1
• MVOSNPUNXINWAD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(Cl)C=C1 MVOSNPUNXINWAD-UHFFFAOYSA-N 0.000 description 1
• DBDHFJKZRWRZIA-UHFFFAOYSA-N 1-(pyrimidin-4-ylmethyl)-9H-carbazole-4-carboxamide Chemical compound N1=CN=C(C=C1)CC1=CC=C(C=2C3=CC=CC=C3NC1=2)C(=O)N DBDHFJKZRWRZIA-UHFFFAOYSA-N 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
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• YOJKKXRJMXIKSR-UHFFFAOYSA-N 1-nitro-2-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1 YOJKKXRJMXIKSR-UHFFFAOYSA-N 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-p-benzoquinone Substances ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
• ZHWXXLFNZSUOPY-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[(3-fluorophenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=C(F)C=CC=3)C2=C1 ZHWXXLFNZSUOPY-UHFFFAOYSA-N 0.000 description 1
• OJNPOEAKXOXCGR-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-[2-(trifluoromethyl)phenyl]ethyl]carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC=C1C(F)(F)F OJNPOEAKXOXCGR-UHFFFAOYSA-N 0.000 description 1
• CPETVVDDMYSLFS-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)-9-[1-[3-(trifluoromethyl)phenyl]ethyl]carbazole-4-carboxamide Chemical compound C12=CC=C(C(=O)N3CC(F)C3)C=C2C2=C(C(N)=O)C=C(C3=C(ON=C3C)C)C=C2N1C(C)C1=CC=CC(C(F)(F)F)=C1 CPETVVDDMYSLFS-UHFFFAOYSA-N 0.000 description 1
• LSXJPJGBWSZHTM-UHFFFAOYSA-N 2-(bromomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CBr LSXJPJGBWSZHTM-UHFFFAOYSA-N 0.000 description 1
• SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
• JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• RCEFMOGVOYEGJN-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one Chemical compound OC1=CC=CC=C1N1C(=O)NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CC1 RCEFMOGVOYEGJN-UHFFFAOYSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• RQSXRGSPGHZKFT-UHFFFAOYSA-N 3-amino-5-bromobenzoic acid Chemical compound NC1=CC(Br)=CC(C(O)=O)=C1 RQSXRGSPGHZKFT-UHFFFAOYSA-N 0.000 description 1
• HPXQNPPYQHVKGF-UHFFFAOYSA-N 3-bromo-5-hydrazinylbenzoic acid;hydrochloride Chemical compound Cl.NNC1=CC(Br)=CC(C(O)=O)=C1 HPXQNPPYQHVKGF-UHFFFAOYSA-N 0.000 description 1
• MTXMEFUEBCFWCY-UHFFFAOYSA-N 3-chloropropyl carbonochloridate Chemical compound ClCCCOC(Cl)=O MTXMEFUEBCFWCY-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• NXUGSYBTPQHKQB-UHFFFAOYSA-N 4-bromo-3-methyl-1,2-oxazole Chemical compound CC1=NOC=C1Br NXUGSYBTPQHKQB-UHFFFAOYSA-N 0.000 description 1
• GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 1
• MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 description 1
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical group COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
• 125000005986 4-piperidonyl group Chemical group 0.000 description 1
• 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
• AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 1
• UFMSWZAKHXRPGS-UHFFFAOYSA-N 5-o-tert-butyl 3-o-ethyl 7-bromo-2,3,4,9-tetrahydro-1h-carbazole-3,5-dicarboxylate Chemical compound N1C2=CC(Br)=CC(C(=O)OC(C)(C)C)=C2C2=C1CCC(C(=O)OCC)C2 UFMSWZAKHXRPGS-UHFFFAOYSA-N 0.000 description 1
• GNMUEVRJHCWKTO-FQEVSTJZSA-N 6h-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide, 4-(4-chlorophenyl)-n-(4-hydroxyphenyl)-2,3,9-trimethyl-, (6s)- Chemical compound C([C@@H]1N=C(C2=C(N3C(C)=NN=C31)SC(=C2C)C)C=1C=CC(Cl)=CC=1)C(=O)NC1=CC=C(O)C=C1 GNMUEVRJHCWKTO-FQEVSTJZSA-N 0.000 description 1
• 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 description 1
• WTOJIGDDDCKPIP-UHFFFAOYSA-N 9-[(4-chloro-2-fluorophenyl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C(=CC(Cl)=CC=3)F)C2=C1 WTOJIGDDDCKPIP-UHFFFAOYSA-N 0.000 description 1
• GTAGJPBAEWDDDF-UHFFFAOYSA-N 9-[(4-chloro-3-fluorophenyl)methyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(3-fluoroazetidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)C4)=CC=C3N(CC=3C=C(F)C(Cl)=CC=3)C2=C1 GTAGJPBAEWDDDF-UHFFFAOYSA-N 0.000 description 1
• FGGFULNAOHYLST-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-ethylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound C1CC(CC)CCN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 FGGFULNAOHYLST-UHFFFAOYSA-N 0.000 description 1
• TWUAWETVPPCEBT-UHFFFAOYSA-N 9-benzyl-2-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(4-hydroxy-2,2,6,6-tetramethylpiperidine-1-carbonyl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4C(CC(O)CC4(C)C)(C)C)=CC=C3N(CC=3C=CC=CC=3)C2=C1 TWUAWETVPPCEBT-UHFFFAOYSA-N 0.000 description 1
• DUWMPJSFSHHEBN-UHFFFAOYSA-N 9-benzyl-5-cyano-7-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-2-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC(C#N)=C2C3=CC=C(C(O)=O)C=C3N(CC=3C=CC=CC=3)C2=C1 DUWMPJSFSHHEBN-UHFFFAOYSA-N 0.000 description 1
• WILXZYYOIAGLTL-UHFFFAOYSA-N 9-benzyl-6-(3,3-difluoroazetidine-1-carbonyl)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC(C(N)=O)=C2C3=CC(C(=O)N4CC(F)(F)C4)=CC=C3N(CC=3C=CC=CC=3)C2=C1 WILXZYYOIAGLTL-UHFFFAOYSA-N 0.000 description 1
• AMGYDFFJPRESPS-UHFFFAOYSA-N 9-benzyl-6-(dimethylcarbamoylamino)-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C12=CC(C3=C(ON=C3C)C)=CC(C(N)=O)=C2C2=CC(NC(=O)N(C)C)=CC=C2N1CC1=CC=CC=C1 AMGYDFFJPRESPS-UHFFFAOYSA-N 0.000 description 1
• VPFZDQAMRYSUKM-KDURUIRLSA-N 9-benzyl-6-[(2r,6s)-2,6-dimethylmorpholine-4-carbonyl]-2-(3,5-dimethyl-1,2-oxazol-4-yl)carbazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(N(CC=2C=CC=CC=2)C=2C3=C(C(N)=O)C=C(C=2)C2=C(ON=C2C)C)C3=C1 VPFZDQAMRYSUKM-KDURUIRLSA-N 0.000 description 1
• FXFRNGBHSNZMQR-UHFFFAOYSA-N 9h-carbazole-4-carbonitrile Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C#N FXFRNGBHSNZMQR-UHFFFAOYSA-N 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
• 208000009304 Acute Kidney Injury Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
• 208000010370 Adenoviridae Infections Diseases 0.000 description 1
• 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 description 1
• 208000016683 Adult T-cell leukemia/lymphoma Diseases 0.000 description 1
• 241000701386 African swine fever virus Species 0.000 description 1
• 201000004384 Alopecia Diseases 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• 206010001935 American trypanosomiasis Diseases 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 235000017060 Arachis glabrata Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 235000010777 Arachis hypogaea Nutrition 0.000 description 1
• 235000018262 Arachis monticola Nutrition 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 206010003591 Ataxia Diseases 0.000 description 1
• 208000031212 Autoimmune polyendocrinopathy Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• 208000009137 Behcet syndrome Diseases 0.000 description 1
• 206010005949 Bone cancer Diseases 0.000 description 1
• 208000018084 Bone neoplasm Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 201000006474 Brain Ischemia Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 206010006417 Bronchial carcinoma Diseases 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• 208000004434 Calcinosis Diseases 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
• 206010007134 Candida infections Diseases 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 229930186147 Cephalosporin Natural products 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• 208000024699 Chagas disease Diseases 0.000 description 1
• 201000006082 Chickenpox Diseases 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 208000000668 Chronic Pancreatitis Diseases 0.000 description 1
• QQKYFCAJVVQWPC-UHFFFAOYSA-N Cl.[B] Chemical group Cl.[B] QQKYFCAJVVQWPC-UHFFFAOYSA-N 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 208000035473 Communicable disease Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 241000711573 Coronaviridae Species 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• 102000003915 DNA Topoisomerases Human genes 0.000 description 1
• 108090000323 DNA Topoisomerases Proteins 0.000 description 1
• 230000000970 DNA cross-linking effect Effects 0.000 description 1
• 241000450599 DNA viruses Species 0.000 description 1
• 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
• 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 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
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• 208000012661 Dyskinesia Diseases 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• 208000000289 Esophageal Achalasia Diseases 0.000 description 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
• 201000006107 Familial adenomatous polyposis Diseases 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 201000008808 Fibrosarcoma Diseases 0.000 description 1
• 206010016654 Fibrosis Diseases 0.000 description 1
• 241000233866 Fungi Species 0.000 description 1
• 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
• 208000024869 Goodpasture syndrome Diseases 0.000 description 1
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 1
• 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 102100039869 Histone H2B type F-S Human genes 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 101001035372 Homo sapiens Histone H2B type F-S Proteins 0.000 description 1
• 101000964584 Homo sapiens Zinc finger protein 160 Proteins 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 206010020850 Hyperthyroidism Diseases 0.000 description 1
• 206010062767 Hypophysitis Diseases 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 1
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 206010023125 Jarisch-Herxheimer reaction Diseases 0.000 description 1
• 208000011200 Kawasaki disease Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
• QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
• 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 206010062038 Lip neoplasm Diseases 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 208000005777 Lupus Nephritis Diseases 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 208000001940 Massive Hepatic Necrosis Diseases 0.000 description 1
• 208000009018 Medullary thyroid cancer Diseases 0.000 description 1
• 208000000172 Medulloblastoma Diseases 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 108091022875 Microtubule Proteins 0.000 description 1
• 102000029749 Microtubule Human genes 0.000 description 1
• 206010049567 Miller Fisher syndrome Diseases 0.000 description 1
• 238000006751 Mitsunobu reaction Methods 0.000 description 1
• 208000003250 Mixed connective tissue disease Diseases 0.000 description 1
• 239000004909 Moisturizer Substances 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
• 206010028424 Myasthenic syndrome Diseases 0.000 description 1
• 208000003926 Myelitis Diseases 0.000 description 1
• 206010028594 Myocardial fibrosis Diseases 0.000 description 1
• 208000009525 Myocarditis Diseases 0.000 description 1
• 201000002481 Myositis Diseases 0.000 description 1
• 206010028665 Myxoedema Diseases 0.000 description 1
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
• GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
• 206010029216 Nervousness Diseases 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• 239000006057 Non-nutritive feed additive Substances 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• 206010030136 Oesophageal achalasia Diseases 0.000 description 1
• 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 208000002193 Pain Diseases 0.000 description 1
• 206010033649 Pancreatitis chronic Diseases 0.000 description 1
• 206010033701 Papillary thyroid cancer Diseases 0.000 description 1
• 208000031481 Pathologic Constriction Diseases 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 201000011152 Pemphigus Diseases 0.000 description 1
• 206010034620 Peripheral sensory neuropathy Diseases 0.000 description 1
• 208000031845 Pernicious anaemia Diseases 0.000 description 1
• 108091000041 Phosphoenolpyruvate Carboxylase Proteins 0.000 description 1
• 208000007452 Plasmacytoma Diseases 0.000 description 1
• 206010035664 Pneumonia Diseases 0.000 description 1
• RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 239000004952 Polyamide Substances 0.000 description 1
• 229920000954 Polyglycolide Polymers 0.000 description 1
• 229920001710 Polyorthoester Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
• 208000037276 Primitive Peripheral Neuroectodermal Tumors Diseases 0.000 description 1
• 229940123573 Protein synthesis inhibitor Drugs 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 208000003782 Raynaud disease Diseases 0.000 description 1
• 208000012322 Raynaud phenomenon Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 208000033626 Renal failure acute Diseases 0.000 description 1
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
• 206010057190 Respiratory tract infections Diseases 0.000 description 1
• 206010038910 Retinitis Diseases 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 235000019485 Safflower oil Nutrition 0.000 description 1
• 206010039705 Scleritis Diseases 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 241000700584 Simplexvirus Species 0.000 description 1
• 208000021386 Sjogren Syndrome Diseases 0.000 description 1
• 208000005718 Stomach Neoplasms Diseases 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 208000001106 Takayasu Arteritis Diseases 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
• 206010043189 Telangiectasia Diseases 0.000 description 1
• 206010043276 Teratoma Diseases 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 206010044248 Toxic shock syndrome Diseases 0.000 description 1
• 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 241000223109 Trypanosoma cruzi Species 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 208000002495 Uterine Neoplasms Diseases 0.000 description 1
• 206010046851 Uveitis Diseases 0.000 description 1
• 206010046865 Vaccinia virus infection Diseases 0.000 description 1
• 206010046980 Varicella Diseases 0.000 description 1
• 206010047642 Vitiligo Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• 102100040815 Zinc finger protein 160 Human genes 0.000 description 1
• NXQGGXCHGDYOHB-UHFFFAOYSA-L [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) Substances [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
• CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
• VJASJHNHBZQZAK-UHFFFAOYSA-N [N].C1=CC=C2C3=CC=CC=C3NC2=C1 Chemical compound [N].C1=CC=C2C3=CC=CC=C3NC2=C1 VJASJHNHBZQZAK-UHFFFAOYSA-N 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• 239000003655 absorption accelerator Substances 0.000 description 1
• 108091005646 acetylated proteins Proteins 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 201000000621 achalasia Diseases 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 201000011040 acute kidney failure Diseases 0.000 description 1
• 208000012998 acute renal failure Diseases 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 208000009956 adenocarcinoma Diseases 0.000 description 1
• 201000006966 adult T-cell leukemia Diseases 0.000 description 1
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
• 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 125000006177 alkyl benzyl group Chemical group 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 125000002947 alkylene group Chemical group 0.000 description 1
• 231100000360 alopecia Toxicity 0.000 description 1
• 229940087168 alpha tocopherol Drugs 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000000843 anti-fungal effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000008135 aqueous vehicle Substances 0.000 description 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
• 125000005239 aroylamino group Chemical group 0.000 description 1
• 210000001367 artery Anatomy 0.000 description 1
• 239000002473 artificial blood Substances 0.000 description 1
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
• 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 125000005110 aryl thio group Chemical group 0.000 description 1
• 238000006254 arylation reaction Methods 0.000 description 1
• 125000004104 aryloxy group Chemical group 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 208000018093 autoimmune cholangitis Diseases 0.000 description 1
• 201000011385 autoimmune polyendocrine syndrome Diseases 0.000 description 1
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 210000003719 b-lymphocyte Anatomy 0.000 description 1
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• 239000003613 bile acid Substances 0.000 description 1
• 150000001607 bioavailable molecules Chemical class 0.000 description 1
• 229940088623 biologically active substance Drugs 0.000 description 1
• 229950000080 birabresib Drugs 0.000 description 1
• 230000017531 blood circulation Effects 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 125000005620 boronic acid group Chemical group 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 239000012267 brine Substances 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• FLHFTXCMKFVKRP-UHFFFAOYSA-N bromomethylcyclobutane Chemical compound BrCC1CCC1 FLHFTXCMKFVKRP-UHFFFAOYSA-N 0.000 description 1
• AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
• 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
• 208000019748 bullous skin disease Diseases 0.000 description 1
• 239000001273 butane Substances 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 235000001465 calcium Nutrition 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 235000012241 calcium silicate Nutrition 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
• 229940127093 camptothecin Drugs 0.000 description 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
• 125000001589 carboacyl group Chemical group 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000001735 carboxylic acids Chemical group 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 238000005266 casting Methods 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 230000020411 cell activation Effects 0.000 description 1
• 210000003855 cell nucleus Anatomy 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 229940124587 cephalosporin Drugs 0.000 description 1
• 150000001780 cephalosporins Chemical class 0.000 description 1
• 208000025434 cerebellar degeneration Diseases 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 239000002738 chelating agent Substances 0.000 description 1
• 238000007385 chemical modification Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 102000022628 chromatin binding proteins Human genes 0.000 description 1
• 108091013410 chromatin binding proteins Proteins 0.000 description 1
• 210000000349 chromosome Anatomy 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 208000029664 classic familial adenomatous polyposis Diseases 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 230000002301 combined effect Effects 0.000 description 1
• 239000007891 compressed tablet Substances 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 230000001276 controlling effect Effects 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000002285 corn oil Substances 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 210000004351 coronary vessel Anatomy 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 229960000913 crospovidone Drugs 0.000 description 1
• 239000003431 cross linking reagent Substances 0.000 description 1
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229940097362 cyclodextrins Drugs 0.000 description 1
• 125000002243 cyclohexanonyl group Chemical class *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960001305 cysteine hydrochloride Drugs 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 239000003405 delayed action preparation Substances 0.000 description 1
• 201000001981 dermatomyositis Diseases 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 238000003745 diagnosis Methods 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 102000038379 digestive enzymes Human genes 0.000 description 1
• 108091007734 digestive enzymes Proteins 0.000 description 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
• 229940000406 drug candidate Drugs 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 239000012636 effector Substances 0.000 description 1
• 125000006575 electron-withdrawing group Chemical group 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 238000005538 encapsulation Methods 0.000 description 1
• 206010014599 encephalitis Diseases 0.000 description 1
• 208000030172 endocrine system disease Diseases 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 229940088598 enzyme Drugs 0.000 description 1
• 230000006718 epigenetic regulation Effects 0.000 description 1
• 201000004101 esophageal cancer Diseases 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• ZXYAWONOWHSQRU-UHFFFAOYSA-N ethyl 4-oxocyclohexanecarboxylate Chemical compound CCOC(=O)C1CCC(=O)CC1 ZXYAWONOWHSQRU-UHFFFAOYSA-N 0.000 description 1
• WAMWLXATYZSKGX-UHFFFAOYSA-N ethyl 9-benzyl-7-bromo-5-carbamoylcarbazole-3-carboxylate Chemical compound C12=CC(Br)=CC(C(N)=O)=C2C2=CC(C(=O)OCC)=CC=C2N1CC1=CC=CC=C1 WAMWLXATYZSKGX-UHFFFAOYSA-N 0.000 description 1
• 229940093499 ethyl acetate Drugs 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 230000005713 exacerbation Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 239000003777 experimental drug Substances 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 230000004761 fibrosis Effects 0.000 description 1
• 230000003176 fibrotic effect Effects 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 238000003818 flash chromatography Methods 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 125000003709 fluoroalkyl group Chemical group 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 201000007487 gallbladder carcinoma Diseases 0.000 description 1
• 206010017758 gastric cancer Diseases 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 230000014509 gene expression Effects 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 208000005017 glioblastoma Diseases 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 210000002149 gonad Anatomy 0.000 description 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
• 125000004995 haloalkylthio group Chemical group 0.000 description 1
• 230000035876 healing Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 201000005787 hematologic cancer Diseases 0.000 description 1
• 208000014951 hematologic disease Diseases 0.000 description 1
• 230000002489 hematologic effect Effects 0.000 description 1
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
• 208000007475 hemolytic anemia Diseases 0.000 description 1
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
• 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
• 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
• 230000006195 histone acetylation Effects 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 239000003667 hormone antagonist Substances 0.000 description 1
• 239000003906 humectant Substances 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 150000002429 hydrazines Chemical class 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 150000004680 hydrogen peroxides Chemical class 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000007954 hypoxia Effects 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 230000004968 inflammatory condition Effects 0.000 description 1
• 230000028709 inflammatory response Effects 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000000138 intercalating agent Substances 0.000 description 1
• 208000036971 interstitial lung disease 2 Diseases 0.000 description 1
• 238000000185 intracerebroventricular administration Methods 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
• 125000005438 isoindazolyl group Chemical group 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 239000000644 isotonic solution Substances 0.000 description 1
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 208000011379 keloid formation Diseases 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 201000003445 large cell neuroendocrine carcinoma Diseases 0.000 description 1
• 201000006721 lip cancer Diseases 0.000 description 1
• 230000037356 lipid metabolism Effects 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Substances [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
• 239000000347 magnesium hydroxide Substances 0.000 description 1
• 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
• 239000000395 magnesium oxide Substances 0.000 description 1
• 235000012245 magnesium oxide Nutrition 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 208000023356 medullary thyroid gland carcinoma Diseases 0.000 description 1
• 206010027191 meningioma Diseases 0.000 description 1
• 208000030159 metabolic disease Diseases 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
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• 230000011987 methylation Effects 0.000 description 1
• 238000007069 methylation reaction Methods 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 239000003094 microcapsule Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 239000004005 microsphere Substances 0.000 description 1
• 210000004688 microtubule Anatomy 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000011259 mixed solution Substances 0.000 description 1
• 230000001333 moisturizer Effects 0.000 description 1
• 239000007932 molded tablet Substances 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
• 239000002324 mouth wash Substances 0.000 description 1
• 229940051866 mouthwash Drugs 0.000 description 1
• 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 description 1
• 210000004400 mucous membrane Anatomy 0.000 description 1
• 206010028417 myasthenia gravis Diseases 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 208000003786 myxedema Diseases 0.000 description 1
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 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
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000009826 neoplastic cell growth Effects 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 230000000926 neurological effect Effects 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 238000013546 non-drug therapy Methods 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• 239000002736 nonionic surfactant Substances 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 210000004940 nucleus Anatomy 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
• 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 description 1
• 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
• 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
• 208000028780 ocular motility disease Diseases 0.000 description 1
• 239000006195 ophthalmic dosage form Substances 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 230000008816 organ damage Effects 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 239000012044 organic layer Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
• 239000006174 pH buffer Substances 0.000 description 1
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 244000045947 parasite Species 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 235000020232 peanut Nutrition 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 201000001976 pemphigus vulgaris Diseases 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• 208000008494 pericarditis Diseases 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
• NONJJLVGHLVQQM-JHXYUMNGSA-N phenethicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C)OC1=CC=CC=C1 NONJJLVGHLVQQM-JHXYUMNGSA-N 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 235000011007 phosphoric acid Nutrition 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000004928 piperidonyl group Chemical group 0.000 description 1
• 229960005235 piperonyl butoxide Drugs 0.000 description 1
• 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
• 210000003635 pituitary gland Anatomy 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 229960000502 poloxamer Drugs 0.000 description 1
• 229920001983 poloxamer Polymers 0.000 description 1
• 229920002647 polyamide Polymers 0.000 description 1
• 201000006292 polyarteritis nodosa Diseases 0.000 description 1
• 239000004417 polycarbonate Substances 0.000 description 1
• 229920000515 polycarbonate Polymers 0.000 description 1
• 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
• 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000021395 porridge Nutrition 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 201000000742 primary sclerosing cholangitis Diseases 0.000 description 1
• 201000008171 proliferative glomerulonephritis Diseases 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
• 239000001294 propane Substances 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 239000000473 propyl gallate Substances 0.000 description 1
• 235000010388 propyl gallate Nutrition 0.000 description 1
• 229940075579 propyl gallate Drugs 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 239000000007 protein synthesis inhibitor Substances 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 238000012797 qualification Methods 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 201000008158 rapidly progressive glomerulonephritis Diseases 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000007115 recruitment Effects 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 208000020615 rectal carcinoma Diseases 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 238000006722 reduction reaction Methods 0.000 description 1
• 238000006476 reductive cyclization reaction Methods 0.000 description 1
• 230000025915 regulation of apoptotic process Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 201000002793 renal fibrosis Diseases 0.000 description 1
• 230000010076 replication Effects 0.000 description 1
• 210000002345 respiratory system Anatomy 0.000 description 1
• 208000023504 respiratory system disease Diseases 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 230000000717 retained effect Effects 0.000 description 1
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 235000005713 safflower oil Nutrition 0.000 description 1
• 239000003813 safflower oil Substances 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 201000000306 sarcoidosis Diseases 0.000 description 1
• 239000013049 sediment Substances 0.000 description 1
• 201000005572 sensory peripheral neuropathy Diseases 0.000 description 1
• 230000035939 shock Effects 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• 229940100996 sodium bisulfate Drugs 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
• 229940001584 sodium metabisulfite Drugs 0.000 description 1
• 235000010262 sodium metabisulphite Nutrition 0.000 description 1
• 235000010344 sodium nitrate Nutrition 0.000 description 1
• 239000004317 sodium nitrate Substances 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 229940001482 sodium sulfite Drugs 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
• 238000007614 solvation Methods 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000003549 soybean oil Substances 0.000 description 1
• 235000012424 soybean oil Nutrition 0.000 description 1
• 150000003413 spiro compounds Chemical class 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 239000003206 sterilizing agent Substances 0.000 description 1
• 201000000498 stomach carcinoma Diseases 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 125000000547 substituted alkyl group Chemical group 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 230000010741 sumoylation Effects 0.000 description 1
• 238000004808 supercritical fluid chromatography Methods 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 208000009056 telangiectasis Diseases 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
• JJXOIFHXNBFRNV-UHFFFAOYSA-N tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C JJXOIFHXNBFRNV-UHFFFAOYSA-N 0.000 description 1
• CQXDYHPBXDZWBA-UHFFFAOYSA-N tert-butyl 2,2,2-trichloroethanimidate Chemical compound CC(C)(C)OC(=N)C(Cl)(Cl)Cl CQXDYHPBXDZWBA-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000002381 testicular Effects 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229940126585 therapeutic drug Drugs 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 125000005309 thioalkoxy group Chemical group 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 208000030045 thyroid gland papillary carcinoma Diseases 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• 230000000451 tissue damage Effects 0.000 description 1
• 231100000827 tissue damage Toxicity 0.000 description 1
• AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
• 229960000984 tocofersolan Drugs 0.000 description 1
• 208000025358 tongue carcinoma Diseases 0.000 description 1
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 108700012359 toxins Proteins 0.000 description 1
• 230000005029 transcription elongation Effects 0.000 description 1
• 238000002054 transplantation Methods 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
• 235000019798 tripotassium phosphate Nutrition 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 230000034512 ubiquitination Effects 0.000 description 1
• 238000010798 ubiquitination Methods 0.000 description 1
• 241000701161 unidentified adenovirus Species 0.000 description 1
• 241001529453 unidentified herpesvirus Species 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000007089 vaccinia Diseases 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 235000019871 vegetable fat Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
• 239000011787 zinc oxide Substances 0.000 description 1
• 235000014692 zinc oxide Nutrition 0.000 description 1
• 239000002076 α-tocopherol Substances 0.000 description 1
• 235000004835 α-tocopherol Nutrition 0.000 description 1