NO314400B1 - Substituerte tricykliske forbindelser - Google Patents
Substituerte tricykliske forbindelser Download PDFInfo
- Publication number
- NO314400B1 NO314400B1 NO19991821A NO991821A NO314400B1 NO 314400 B1 NO314400 B1 NO 314400B1 NO 19991821 A NO19991821 A NO 19991821A NO 991821 A NO991821 A NO 991821A NO 314400 B1 NO314400 B1 NO 314400B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- hydroxy
- oxyacetic acid
- carbamoyl
- benzyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 114
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 5
- 230000036303 septic shock Effects 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 709
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 240
- 239000002253 acid Substances 0.000 claims description 166
- 238000002360 preparation method Methods 0.000 claims description 143
- -1 tri-(1-methylethyl)silyl Chemical group 0.000 claims description 126
- 150000004702 methyl esters Chemical class 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- YAQSQUUCVARXHF-UHFFFAOYSA-N methyl 5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CCC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 YAQSQUUCVARXHF-UHFFFAOYSA-N 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 28
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 26
- 159000000000 sodium salts Chemical class 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 17
- 206010003246 arthritis Diseases 0.000 claims description 17
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 15
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 9
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 9
- PHRABVHYUHIYGY-UHFFFAOYSA-N 1-methylnaphthalene Chemical group C1=CC=C2C([CH2])=CC=CC2=C1 PHRABVHYUHIYGY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- GRNUVEMCUGCDDO-UHFFFAOYSA-N methyl 7-methyl-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(C)CC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 GRNUVEMCUGCDDO-UHFFFAOYSA-N 0.000 claims description 8
- OXQCZJHYRFSEQM-UHFFFAOYSA-N 2-[5-carbamoyl-2-methyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC=CC(CN2C3=CC(C)=CC(OCC(O)=O)=C3C3=C(C(N)=O)C=CC=C32)=C1 OXQCZJHYRFSEQM-UHFFFAOYSA-N 0.000 claims description 7
- UJSZZKJIGGAMHM-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-methylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC=CC=C1CN1C2=CC=CC(C(N)=O)=C2C2=C(OCC(O)=O)C=CC=C21 UJSZZKJIGGAMHM-UHFFFAOYSA-N 0.000 claims description 7
- GSUXBSRHWJBQBV-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]-2-methylcarbazol-4-yl]oxyacetic acid Chemical compound C=1C(C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC(F)=C1 GSUXBSRHWJBQBV-UHFFFAOYSA-N 0.000 claims description 7
- SKVCADFJTHKAEY-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-iodophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(I)=C1 SKVCADFJTHKAEY-UHFFFAOYSA-N 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 7
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 claims description 7
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 claims description 7
- XRRDFIPYLFCYLU-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical group [CH2]C1=CC(C)=CC(C)=C1 XRRDFIPYLFCYLU-UHFFFAOYSA-N 0.000 claims description 6
- HWVCTTFKEFUZSR-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-phenylcarbazol-4-yl)oxyacetic acid Chemical compound C12=CC(C=3C=CC=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 HWVCTTFKEFUZSR-UHFFFAOYSA-N 0.000 claims description 6
- URFXAPISJQEWEH-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2,6-dichlorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl URFXAPISJQEWEH-UHFFFAOYSA-N 0.000 claims description 6
- AKPJTFHUTNPVJJ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-cyanophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C#N AKPJTFHUTNPVJJ-UHFFFAOYSA-N 0.000 claims description 6
- MQZAJAXITWPMFM-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-fluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1F MQZAJAXITWPMFM-UHFFFAOYSA-N 0.000 claims description 6
- KQQRGQBJPMVABZ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[2-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F KQQRGQBJPMVABZ-UHFFFAOYSA-N 0.000 claims description 6
- 208000012659 Joint disease Diseases 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- YIWKRIZOIPDUPO-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl)oxyacetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(C2=C(C(N)=O)C=CC=C22)=C1N2CC1=CC=CC=C1 YIWKRIZOIPDUPO-UHFFFAOYSA-N 0.000 claims description 5
- AAYKHTVNNLLGLP-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methylcarbazol-4-yl)oxyacetic acid Chemical compound C=1C(C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 AAYKHTVNNLLGLP-UHFFFAOYSA-N 0.000 claims description 5
- YAENEAAYRCUGQB-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3,5-dimethylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC(C)=CC(CN2C3=CC=CC(=C3C3=C(OCC(O)=O)C=CC=C32)C(N)=O)=C1 YAENEAAYRCUGQB-UHFFFAOYSA-N 0.000 claims description 5
- JCJMBFNXBWSTLL-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-phenoxyphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 JCJMBFNXBWSTLL-UHFFFAOYSA-N 0.000 claims description 5
- APSSLGLEOLPZAI-UHFFFAOYSA-N 9-benzyl-5-[2-(methanesulfonamido)ethoxy]-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(OCCNS(C)(=O)=O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 APSSLGLEOLPZAI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 208000014674 injury Diseases 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- UFJILQXRMNERCL-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoylcarbazol-4-yl)oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 UFJILQXRMNERCL-UHFFFAOYSA-N 0.000 claims description 4
- CRXQYSQDOBKHNV-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound NC(=O)C1CCCC2=C1C1=C(OCC(O)=O)C=CC=C1N2CC1=CC=CC=C1 CRXQYSQDOBKHNV-UHFFFAOYSA-N 0.000 claims description 4
- FRZSYHNHELRNDK-UHFFFAOYSA-N 2-[9-[(2-benzylphenyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 FRZSYHNHELRNDK-UHFFFAOYSA-N 0.000 claims description 4
- YSYSKDYLPVNKKJ-UHFFFAOYSA-N 9-benzyl-5-(cyanomethoxy)-7-methoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(OCC#N)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 YSYSKDYLPVNKKJ-UHFFFAOYSA-N 0.000 claims description 4
- AELSAUYZEFGGJU-UHFFFAOYSA-N 9-benzyl-5-[2-(methanesulfonamido)ethoxy]-7-methoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(OCCNS(C)(=O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 AELSAUYZEFGGJU-UHFFFAOYSA-N 0.000 claims description 4
- XABCYFUHAKJZCS-UHFFFAOYSA-N 9-benzyl-8-fluoro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OC)=CC=C(F)C=2N1CC1=CC=CC=C1 XABCYFUHAKJZCS-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 208000036487 Arthropathies Diseases 0.000 claims description 4
- 206010006448 Bronchiolitis Diseases 0.000 claims description 4
- 208000004575 Infectious Arthritis Diseases 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical class 0.000 claims description 4
- NCFKVOYLJUVJPQ-UHFFFAOYSA-N methyl 8-[(3-chlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(Cl)=C1 NCFKVOYLJUVJPQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 208000002574 reactive arthritis Diseases 0.000 claims description 4
- PRAUIYBTAAOMCZ-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxypropanoic acid Chemical compound C=1C(OC)=CC(OC(C)C(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 PRAUIYBTAAOMCZ-UHFFFAOYSA-N 0.000 claims description 3
- LUURCHSHYLGPEG-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-1-fluoro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound NC(=O)C1CCCC2=C1C1=C(OCC(O)=O)C=CC(F)=C1N2CC1=CC=CC=C1 LUURCHSHYLGPEG-UHFFFAOYSA-N 0.000 claims description 3
- OCQARBMASQXXGZ-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-1-methyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound C1=2C(C)=CC=C(OCC(O)=O)C=2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 OCQARBMASQXXGZ-UHFFFAOYSA-N 0.000 claims description 3
- VRMKRGKLFIJSNY-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2,6-difluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(F)C=CC=C1F VRMKRGKLFIJSNY-UHFFFAOYSA-N 0.000 claims description 3
- LCPAHBQVBUXTEZ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-cyanophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(C#N)=C1 LCPAHBQVBUXTEZ-UHFFFAOYSA-N 0.000 claims description 3
- KWBVGNHCBQIRTN-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1 KWBVGNHCBQIRTN-UHFFFAOYSA-N 0.000 claims description 3
- IKVWXTBYJHSVHF-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound CC1=CC=CC(CN2C3=CC=CC(=C3C3=C(OCC(O)=O)C=CC=C32)C(N)=O)=C1 IKVWXTBYJHSVHF-UHFFFAOYSA-N 0.000 claims description 3
- CGZZUCYZEGYRAT-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(OC)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 CGZZUCYZEGYRAT-UHFFFAOYSA-N 0.000 claims description 3
- MAWQJLBAPRFZIH-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(OC)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 MAWQJLBAPRFZIH-UHFFFAOYSA-N 0.000 claims description 3
- ILIKMDNKNZVOMD-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-methoxycarbazole-4-carboxamide Chemical compound C=1C(OC)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 ILIKMDNKNZVOMD-UHFFFAOYSA-N 0.000 claims description 3
- GWSIUDSDXNVENV-UHFFFAOYSA-N 9-benzyl-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 GWSIUDSDXNVENV-UHFFFAOYSA-N 0.000 claims description 3
- DVQREHPZPZCGLD-UHFFFAOYSA-N 9-benzyl-8-fluoro-5-methoxycarbazole-4-carboxamide Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OC)=CC=C(F)C=2N1CC1=CC=CC=C1 DVQREHPZPZCGLD-UHFFFAOYSA-N 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- NLFVLWRTYIDKGT-UHFFFAOYSA-N COC(COC1=CC(=CC=2N(C3=CC=CC(=C3C1=2)C(N)=O)CC1=CC=CC=C1)CO[Si](C(C)C)(C(C)C)C(C)C)=O Chemical compound COC(COC1=CC(=CC=2N(C3=CC=CC(=C3C1=2)C(N)=O)CC1=CC=CC=C1)CO[Si](C(C)C)(C(C)C)C(C)C)=O NLFVLWRTYIDKGT-UHFFFAOYSA-N 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- SWWDNZRFRCJACD-UHFFFAOYSA-N ethyl 9-benzyl-8-fluoro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1C1=C(OC)C=CC(F)=C1N2CC1=CC=CC=C1 SWWDNZRFRCJACD-UHFFFAOYSA-N 0.000 claims description 3
- 208000002085 hemarthrosis Diseases 0.000 claims description 3
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 3
- QCYHHHHOQGEKIE-UHFFFAOYSA-N methyl 2-(2-methoxyphenyl)-3-nitrobenzoate Chemical group COC(=O)C1=CC=CC([N+]([O-])=O)=C1C1=CC=CC=C1OC QCYHHHHOQGEKIE-UHFFFAOYSA-N 0.000 claims description 3
- NIRLBKXYTDHSFZ-UHFFFAOYSA-N methyl 2-bromo-3-[(4-methyl-6-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(C)CC=2)=O)=C1Br NIRLBKXYTDHSFZ-UHFFFAOYSA-N 0.000 claims description 3
- SWIUIZXMNZTCRX-UHFFFAOYSA-N methyl 7-(hydroxymethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(CO)CC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 SWIUIZXMNZTCRX-UHFFFAOYSA-N 0.000 claims description 3
- PKFVGCGERGKRQI-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-phenylcarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 PKFVGCGERGKRQI-UHFFFAOYSA-N 0.000 claims description 3
- VJZMHAFNPNAFCS-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-propan-2-ylcarbazole-4-carboxylate Chemical compound C12=CC(C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VJZMHAFNPNAFCS-UHFFFAOYSA-N 0.000 claims description 3
- ZHYOTVKRNRGRAI-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-pentyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound O=C1CC(CCCCC)CC2=C1C1=C(C(=O)OC)C=CC=C1N2CC1=CC=CC=C1 ZHYOTVKRNRGRAI-UHFFFAOYSA-N 0.000 claims description 3
- XFTAOPDANGNLBE-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-phenyl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 XFTAOPDANGNLBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- LUMYPAZSFDGHFI-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-[tri(propan-2-yl)silyloxymethyl]carbazol-4-yl]oxyacetic acid Chemical compound C=1C(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 LUMYPAZSFDGHFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- DRRPBTBDXRFNRV-UHFFFAOYSA-N 5-hydroxy-7-methyl-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound CC1=CC=CC(CC=2C3=C(C4=C(C(N)=O)C=CC=C4N3)C(O)=CC=2C)=C1 DRRPBTBDXRFNRV-UHFFFAOYSA-N 0.000 claims description 2
- PKWKOZFVBKURBY-UHFFFAOYSA-N 5-hydroxy-8-(pyridin-2-ylmethyl)-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=N1 PKWKOZFVBKURBY-UHFFFAOYSA-N 0.000 claims description 2
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- PYPQRPRJXASPOF-UHFFFAOYSA-N methyl 2-[9-benzyl-5-carbamoyl-2-(furan-2-yl)carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C=3OC=CC=3)=CC=2N1CC1=CC=CC=C1 PYPQRPRJXASPOF-UHFFFAOYSA-N 0.000 claims 1
- IFEUCXUVVPNSIG-UHFFFAOYSA-N methyl 2-bromo-3-[(6-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCCC=2)=O)=C1Br IFEUCXUVVPNSIG-UHFFFAOYSA-N 0.000 claims 1
- LDRKDSVFVSBAAT-UHFFFAOYSA-N methyl 2-chloro-3-[(6-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CCCC=2)=O)=C1Cl LDRKDSVFVSBAAT-UHFFFAOYSA-N 0.000 claims 1
- DRBWJKXGTZSNRR-UHFFFAOYSA-N methyl 5-hydroxy-8-(pyridin-2-ylmethyl)-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=N1 DRBWJKXGTZSNRR-UHFFFAOYSA-N 0.000 claims 1
- OCPKAVXMHCEGPV-UHFFFAOYSA-N methyl 5-hydroxy-8-[(3-iodophenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(I)=C1 OCPKAVXMHCEGPV-UHFFFAOYSA-N 0.000 claims 1
- NKUXPDUQKHJSPS-UHFFFAOYSA-N methyl 8-[(2,6-difluorophenyl)methyl]-5-hydroxy-9H-carbazole-4-carboxylate Chemical compound FC1=C(C(=CC=C1)F)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(=O)OC)O NKUXPDUQKHJSPS-UHFFFAOYSA-N 0.000 claims 1
- XCGUNJVHYPYOLO-UHFFFAOYSA-N methyl 8-[(2-chlorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1Cl XCGUNJVHYPYOLO-UHFFFAOYSA-N 0.000 claims 1
- UBHOTNBNIBIRCF-UHFFFAOYSA-N methyl 8-benzyl-5-hydroxy-9H-carbazole-4-carboxylate Chemical compound COC(=O)c1cccc2[nH]c3c(Cc4ccccc4)ccc(O)c3c12 UBHOTNBNIBIRCF-UHFFFAOYSA-N 0.000 claims 1
- UUTJGUDEDSFFHG-UHFFFAOYSA-N methyl 8-benzyl-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1 UUTJGUDEDSFFHG-UHFFFAOYSA-N 0.000 claims 1
- IMOVFZJGDDTZJA-UHFFFAOYSA-N methyl 9-benzyl-7-(furan-2-yl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3OC=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 IMOVFZJGDDTZJA-UHFFFAOYSA-N 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 201000006292 polyarteritis nodosa Diseases 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 abstract description 6
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 5
- 239000000194 fatty acid Substances 0.000 abstract description 5
- 229930195729 fatty acid Natural products 0.000 abstract description 5
- 150000004665 fatty acids Chemical class 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 271
- 235000019439 ethyl acetate Nutrition 0.000 description 247
- 239000000203 mixture Substances 0.000 description 237
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 212
- 238000005160 1H NMR spectroscopy Methods 0.000 description 206
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 205
- 238000000921 elemental analysis Methods 0.000 description 199
- 239000000243 solution Substances 0.000 description 192
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 153
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 151
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 147
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 147
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 134
- 239000007787 solid Substances 0.000 description 129
- 239000000741 silica gel Substances 0.000 description 124
- 229910002027 silica gel Inorganic materials 0.000 description 124
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 122
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 122
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 99
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 82
- 238000004440 column chromatography Methods 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- 229910001868 water Inorganic materials 0.000 description 67
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 65
- 235000019341 magnesium sulphate Nutrition 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 59
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 58
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 51
- 238000000034 method Methods 0.000 description 49
- 239000000725 suspension Substances 0.000 description 48
- 239000012267 brine Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 44
- 239000010410 layer Substances 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 41
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
- 239000000284 extract Substances 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 35
- 238000001914 filtration Methods 0.000 description 35
- 229920006395 saturated elastomer Polymers 0.000 description 35
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 34
- 235000011114 ammonium hydroxide Nutrition 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000002244 precipitate Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- 239000000908 ammonium hydroxide Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 description 30
- 229910000104 sodium hydride Inorganic materials 0.000 description 30
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 29
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- 239000000843 powder Substances 0.000 description 27
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 25
- 235000011181 potassium carbonates Nutrition 0.000 description 25
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 239000012312 sodium hydride Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 239000006260 foam Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- 239000002480 mineral oil Substances 0.000 description 15
- 235000010446 mineral oil Nutrition 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- NIXWZYZFLFEHMB-UHFFFAOYSA-N methyl 3-amino-2-bromobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Br NIXWZYZFLFEHMB-UHFFFAOYSA-N 0.000 description 12
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 230000002452 interceptive effect Effects 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 150000005181 nitrobenzenes Chemical class 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- YUWPKYJCYRFBJT-UHFFFAOYSA-N methyl 2-bromo-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1Br YUWPKYJCYRFBJT-UHFFFAOYSA-N 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- NKBQKMXNIWIFAE-UHFFFAOYSA-N methyl 3-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Cl NKBQKMXNIWIFAE-UHFFFAOYSA-N 0.000 description 7
- PSNSVDSRLUYDKF-UHFFFAOYSA-N methyl benzenesulfinate Chemical compound COS(=O)C1=CC=CC=C1 PSNSVDSRLUYDKF-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 7
- 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 7
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 6
- 239000011592 zinc chloride Substances 0.000 description 6
- 235000005074 zinc chloride Nutrition 0.000 description 6
- PATZGVUJUUNVJN-UHFFFAOYSA-N 2-[5-carbamoyl-9-(naphthalen-1-ylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(OCC(O)=O)=C2C2=C1C=CC=C2C(=O)N PATZGVUJUUNVJN-UHFFFAOYSA-N 0.000 description 5
- HVKYETJTIUJSLB-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2-chlorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1Cl HVKYETJTIUJSLB-UHFFFAOYSA-N 0.000 description 5
- WTDJEGSXLFHZPY-UHFFFAOYSA-N 2-bromo-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1Br WTDJEGSXLFHZPY-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- JBCQPBVZKBEHNF-UHFFFAOYSA-N methyl 2-chloro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JBCQPBVZKBEHNF-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 229940001593 sodium carbonate Drugs 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 235000009518 sodium iodide Nutrition 0.000 description 5
- HCQNYAIKYZCDBC-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-propan-2-ylcarbazol-4-yl)oxyacetic acid Chemical compound C=1C(C(C)C)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 HCQNYAIKYZCDBC-UHFFFAOYSA-N 0.000 description 4
- BLCNILYGCATZEH-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(2,3-difluorophenyl)methyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1F BLCNILYGCATZEH-UHFFFAOYSA-N 0.000 description 4
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
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- JTWGFKHCAPESJY-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(furan-2-yl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(C=3OC=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 JTWGFKHCAPESJY-UHFFFAOYSA-N 0.000 description 3
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 3
- VXCYQLJSFFVGMX-UHFFFAOYSA-N 5-hydroxy-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 VXCYQLJSFFVGMX-UHFFFAOYSA-N 0.000 description 3
- GLUGRMILFITQLF-UHFFFAOYSA-N 5-hydroxy-9-[[3-(trifluoromethoxy)phenyl]methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 GLUGRMILFITQLF-UHFFFAOYSA-N 0.000 description 3
- GBTJVHADNGRQBQ-UHFFFAOYSA-N 5-methoxy-8-methyl-9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1C(C)=CC=C2OC GBTJVHADNGRQBQ-UHFFFAOYSA-N 0.000 description 3
- ZQBMPCCWRBCRQX-UHFFFAOYSA-N 9-[(2,3-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1F ZQBMPCCWRBCRQX-UHFFFAOYSA-N 0.000 description 3
- IULCUUPYAJAXDL-UHFFFAOYSA-N 9-[(2,6-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(F)C=CC=C1F IULCUUPYAJAXDL-UHFFFAOYSA-N 0.000 description 3
- JRWSMGTUZSZVEN-UHFFFAOYSA-N 9-[(2-benzylphenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 JRWSMGTUZSZVEN-UHFFFAOYSA-N 0.000 description 3
- SRAJNLCQHFQSIZ-UHFFFAOYSA-N 9-[(2-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1F SRAJNLCQHFQSIZ-UHFFFAOYSA-N 0.000 description 3
- SSKLUMQEAPFGGT-UHFFFAOYSA-N 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OC)=CC=C(C)C=2N1CC1=CC=CC=C1 SSKLUMQEAPFGGT-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- PCVLMLMVJMGCJV-UHFFFAOYSA-N methyl 5-hydroxy-9-(pyridin-2-ylmethyl)carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=N1 PCVLMLMVJMGCJV-UHFFFAOYSA-N 0.000 description 3
- TWOPOKNACRNJDU-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-iodophenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(I)=C1 TWOPOKNACRNJDU-UHFFFAOYSA-N 0.000 description 3
- UNVNCIUTBUGNTR-UHFFFAOYSA-N methyl 5-hydroxy-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F UNVNCIUTBUGNTR-UHFFFAOYSA-N 0.000 description 3
- QOPNWBDBQJGPAE-UHFFFAOYSA-N methyl 5-hydroxy-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 QOPNWBDBQJGPAE-UHFFFAOYSA-N 0.000 description 3
- MRQKZMCJLKMCJL-UHFFFAOYSA-N methyl 9-[(2,6-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(F)C=CC=C1F MRQKZMCJLKMCJL-UHFFFAOYSA-N 0.000 description 3
- XTYILSXHCGTKHW-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl XTYILSXHCGTKHW-UHFFFAOYSA-N 0.000 description 3
- FIORTLXKZVVDKE-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N FIORTLXKZVVDKE-UHFFFAOYSA-N 0.000 description 3
- ZFFJJZQSUVMMOI-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F ZFFJJZQSUVMMOI-UHFFFAOYSA-N 0.000 description 3
- KYSDGKPVRQSADQ-UHFFFAOYSA-N methyl 9-[(3,5-dimethylphenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC(C)=CC(C)=C1 KYSDGKPVRQSADQ-UHFFFAOYSA-N 0.000 description 3
- OEGIIJDSTAEKEM-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 OEGIIJDSTAEKEM-UHFFFAOYSA-N 0.000 description 3
- GGSHGRAQDSJBOY-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 GGSHGRAQDSJBOY-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
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- 239000012071 phase Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical class [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BGMMWAHLBZGOBB-UHFFFAOYSA-N (2-chloro-4-fluoro-5-nitrophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=CC([N+]([O-])=O)=C(F)C=C1Cl BGMMWAHLBZGOBB-UHFFFAOYSA-N 0.000 description 2
- YQKSSJXIMXARGI-UHFFFAOYSA-N (2-chloro-4-fluorophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=CC=C(F)C=C1Cl YQKSSJXIMXARGI-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- FWLWTILKTABGKQ-UHFFFAOYSA-N 1-(bromomethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CBr)=C1 FWLWTILKTABGKQ-UHFFFAOYSA-N 0.000 description 2
- CRONHBXGPYQWHX-UHFFFAOYSA-N 1-chloro-5-fluoro-2-methoxy-4-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=C(F)C=C1Cl CRONHBXGPYQWHX-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- XMNFDVRHTKIVQK-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxyacetic acid Chemical compound C=1C(OC)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 XMNFDVRHTKIVQK-UHFFFAOYSA-N 0.000 description 2
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 2
- FZCVOGNJZMDIQT-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-[4-(trifluoromethyl)phenyl]carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 FZCVOGNJZMDIQT-UHFFFAOYSA-N 0.000 description 2
- RUTKJXMYXZFXPQ-UHFFFAOYSA-N 2-fluoro-5-methoxyaniline Chemical class COC1=CC=C(F)C(N)=C1 RUTKJXMYXZFXPQ-UHFFFAOYSA-N 0.000 description 2
- FBELQXBIHJGQRS-UHFFFAOYSA-N 5-hydroxy-7-methyl-9-[(3-methylphenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC(C)=CC(O)=C3C3=C(C(N)=O)C=CC=C32)=C1 FBELQXBIHJGQRS-UHFFFAOYSA-N 0.000 description 2
- RUEFNDMBRXTRPS-UHFFFAOYSA-N 5-hydroxy-9-(pyridin-3-ylmethyl)carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CN=C1 RUEFNDMBRXTRPS-UHFFFAOYSA-N 0.000 description 2
- GIJITUQEJWSBRI-UHFFFAOYSA-N 5-hydroxy-9-[(2-methylphenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=CC=CC=C1CN1C2=CC=CC(C(N)=O)=C2C2=C(O)C=CC=C21 GIJITUQEJWSBRI-UHFFFAOYSA-N 0.000 description 2
- SFVXFRXONWSBOB-UHFFFAOYSA-N 5-hydroxy-9-[(3-iodophenyl)methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(I)=C1 SFVXFRXONWSBOB-UHFFFAOYSA-N 0.000 description 2
- KQXAXQGJCMZYBA-UHFFFAOYSA-N 5-hydroxy-9-[(3-methylphenyl)methyl]carbazole-4-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(=C3C3=C(O)C=CC=C32)C(N)=O)=C1 KQXAXQGJCMZYBA-UHFFFAOYSA-N 0.000 description 2
- MSRUWXVJOFPJQK-UHFFFAOYSA-N 5-hydroxy-9-[[2-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F MSRUWXVJOFPJQK-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- 238000007126 N-alkylation reaction Methods 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 239000000538 analytical sample Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
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- 229910052794 bromium Inorganic materials 0.000 description 2
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- 244000309464 bull Species 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
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- 238000007796 conventional method Methods 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- 239000012380 dealkylating agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- NTTXCAMHFZZOTH-UHFFFAOYSA-N ethyl 5-methoxy-8-methyl-2,3,4,9-tetrahydro-1h-carbazole-4-carboxylate Chemical compound N1C2=C(C)C=CC(OC)=C2C2=C1CCCC2C(=O)OCC NTTXCAMHFZZOTH-UHFFFAOYSA-N 0.000 description 2
- AANXBKIMDTVFQA-UHFFFAOYSA-N ethyl 9-benzyl-8-chloro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1C1=C(OC)C=CC(Cl)=C1N2CC1=CC=CC=C1 AANXBKIMDTVFQA-UHFFFAOYSA-N 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052740 iodine Chemical group 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- KDHXHMORUAHVQC-UHFFFAOYSA-M lithium;2-[9-benzyl-5-carbamoyl-2-[tri(propan-2-yl)silyloxymethyl]carbazol-4-yl]oxyacetate Chemical compound [Li+].C=1C(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(OCC([O-])=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 KDHXHMORUAHVQC-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- QAGFBWORHHSDLU-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-2-methylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C)=CC=2N1CC1=CC=CC=C1 QAGFBWORHHSDLU-UHFFFAOYSA-N 0.000 description 2
- VYJSSWLKFMVSKB-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VYJSSWLKFMVSKB-UHFFFAOYSA-N 0.000 description 2
- ADHVHSIJKWWKPA-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2-fluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F ADHVHSIJKWWKPA-UHFFFAOYSA-N 0.000 description 2
- CLVREPBFXISVON-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3,5-dimethylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC(C)=CC(C)=C1 CLVREPBFXISVON-UHFFFAOYSA-N 0.000 description 2
- CHNIRPZCTJAGDW-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3-iodophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(I)=C1 CHNIRPZCTJAGDW-UHFFFAOYSA-N 0.000 description 2
- HBLWDERQOAUKGN-UHFFFAOYSA-N methyl 2-bromo-3-[(5-methyl-3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(C)CC(=O)C=2)=C1Br HBLWDERQOAUKGN-UHFFFAOYSA-N 0.000 description 2
- LHOAGMPBVLOYLJ-UHFFFAOYSA-N methyl 2-bromo-3-[[3-oxo-5-[4-(trifluoromethyl)phenyl]cyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1Br LHOAGMPBVLOYLJ-UHFFFAOYSA-N 0.000 description 2
- PFNZJCITVCCGNP-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-9-[(3-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 PFNZJCITVCCGNP-UHFFFAOYSA-N 0.000 description 2
- DEJNWOYTOSFGQM-UHFFFAOYSA-N methyl 5-hydroxy-9-(naphthalen-1-ylmethyl)carbazole-4-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(O)=C2C2=C1C=CC=C2C(=O)OC DEJNWOYTOSFGQM-UHFFFAOYSA-N 0.000 description 2
- YIEMRYNGKWONSK-UHFFFAOYSA-N methyl 5-hydroxy-9-(pyridin-3-ylmethyl)carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CN=C1 YIEMRYNGKWONSK-UHFFFAOYSA-N 0.000 description 2
- DWIAYAAEVRBFGW-UHFFFAOYSA-N methyl 5-hydroxy-9-[(2-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C DWIAYAAEVRBFGW-UHFFFAOYSA-N 0.000 description 2
- ZLSAMYFQRGMPFY-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-methylphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 ZLSAMYFQRGMPFY-UHFFFAOYSA-N 0.000 description 2
- ZEMCNOHCNUFOAM-UHFFFAOYSA-N methyl 5-hydroxy-9-[(3-phenoxyphenyl)methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 ZEMCNOHCNUFOAM-UHFFFAOYSA-N 0.000 description 2
- LPGOWPXYSCNOID-UHFFFAOYSA-N methyl 5-hydroxy-9-[[3-(trifluoromethoxy)phenyl]methyl]carbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 LPGOWPXYSCNOID-UHFFFAOYSA-N 0.000 description 2
- XCBKEVAXNVDHMT-UHFFFAOYSA-N methyl 5-hydroxy-9H-carbazole-4-carboxylate Chemical compound OC1=CC=CC=2NC3=CC=CC(=C3C1=2)C(=O)OC XCBKEVAXNVDHMT-UHFFFAOYSA-N 0.000 description 2
- WAUGXTPQYOKHNZ-UHFFFAOYSA-N methyl 5-oxo-7-pentyl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound N1C2=CC=CC(C(=O)OC)=C2C2=C1CC(CCCCC)CC2=O WAUGXTPQYOKHNZ-UHFFFAOYSA-N 0.000 description 2
- YDTQOOFEQXDLDW-UHFFFAOYSA-N methyl 5-oxo-7-propan-2-yl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(C(C)C)CC(=O)C2=C1NC1=C2C(C(=O)OC)=CC=C1 YDTQOOFEQXDLDW-UHFFFAOYSA-N 0.000 description 2
- YBGBXOFBYJAQNA-UHFFFAOYSA-N methyl 5-oxo-9-(pyridin-2-ylmethyl)-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=N1 YBGBXOFBYJAQNA-UHFFFAOYSA-N 0.000 description 2
- MYCRKMVCEFJGCB-UHFFFAOYSA-N methyl 5-oxo-9-(pyridin-3-ylmethyl)-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CN=C1 MYCRKMVCEFJGCB-UHFFFAOYSA-N 0.000 description 2
- YTCCWBPOFPFFCR-UHFFFAOYSA-N methyl 5-oxo-9-[(3-phenoxyphenyl)methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 YTCCWBPOFPFFCR-UHFFFAOYSA-N 0.000 description 2
- PEPCSOVPNMWRKL-UHFFFAOYSA-N methyl 5-oxo-9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 PEPCSOVPNMWRKL-UHFFFAOYSA-N 0.000 description 2
- LQLQHQVSCDFJIP-UHFFFAOYSA-N methyl 7-methyl-9-[(3-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 LQLQHQVSCDFJIP-UHFFFAOYSA-N 0.000 description 2
- HZLCOQKRNRZMBL-UHFFFAOYSA-N methyl 9-(naphthalen-1-ylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1CCC(=O)C2=C1N(CC=1C3=CC=CC=C3C=CC=1)C1=C2C(C(=O)OC)=CC=C1 HZLCOQKRNRZMBL-UHFFFAOYSA-N 0.000 description 2
- FFJIJEXTIQAHDU-UHFFFAOYSA-N methyl 9-[(2,3-difluorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1F FFJIJEXTIQAHDU-UHFFFAOYSA-N 0.000 description 2
- NZRDUNGWEBSXKX-UHFFFAOYSA-N methyl 9-[(2,3-difluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1F NZRDUNGWEBSXKX-UHFFFAOYSA-N 0.000 description 2
- MQNNUYXCYBUUPW-UHFFFAOYSA-N methyl 9-[(2,6-dichlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl MQNNUYXCYBUUPW-UHFFFAOYSA-N 0.000 description 2
- RMDLRBVVUSFDPK-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 RMDLRBVVUSFDPK-UHFFFAOYSA-N 0.000 description 2
- GSKCQVFTFZVUDE-UHFFFAOYSA-N methyl 9-[(2-benzylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 GSKCQVFTFZVUDE-UHFFFAOYSA-N 0.000 description 2
- ZYVPKFGMYOFKST-UHFFFAOYSA-N methyl 9-[(2-chlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1Cl ZYVPKFGMYOFKST-UHFFFAOYSA-N 0.000 description 2
- HIEJYFQOXJHYHA-UHFFFAOYSA-N methyl 9-[(2-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N HIEJYFQOXJHYHA-UHFFFAOYSA-N 0.000 description 2
- XFHQZLZSUZCKLV-UHFFFAOYSA-N methyl 9-[(2-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1F XFHQZLZSUZCKLV-UHFFFAOYSA-N 0.000 description 2
- QLXRVTDGPVGHFD-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 QLXRVTDGPVGHFD-UHFFFAOYSA-N 0.000 description 2
- RMSKZGQSHDPGNL-UHFFFAOYSA-N methyl 9-[(3-chlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(Cl)=C1 RMSKZGQSHDPGNL-UHFFFAOYSA-N 0.000 description 2
- UXAWWFVDQJYGDY-UHFFFAOYSA-N methyl 9-[(3-cyanophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C#N)=C1 UXAWWFVDQJYGDY-UHFFFAOYSA-N 0.000 description 2
- SNOCNJSDASZTKU-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 SNOCNJSDASZTKU-UHFFFAOYSA-N 0.000 description 2
- JSOLWPACLIOTBG-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 JSOLWPACLIOTBG-UHFFFAOYSA-N 0.000 description 2
- HBLQCKSZNTXTII-UHFFFAOYSA-N methyl 9-[(3-fluorophenyl)methyl]-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1 HBLQCKSZNTXTII-UHFFFAOYSA-N 0.000 description 2
- GKCQFBAIJMCCKA-UHFFFAOYSA-N methyl 9-[(3-iodophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(I)=C1 GKCQFBAIJMCCKA-UHFFFAOYSA-N 0.000 description 2
- HXURTMLFEIDBBQ-UHFFFAOYSA-N methyl 9-[(3-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 HXURTMLFEIDBBQ-UHFFFAOYSA-N 0.000 description 2
- GSSRRPUGXNPLSG-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-methylcarbazole-4-carboxylate Chemical compound C12=CC(C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 GSSRRPUGXNPLSG-UHFFFAOYSA-N 0.000 description 2
- LRAQLBIAAGYKIS-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 LRAQLBIAAGYKIS-UHFFFAOYSA-N 0.000 description 2
- OAKDTHHXAYPQFO-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-propan-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 OAKDTHHXAYPQFO-UHFFFAOYSA-N 0.000 description 2
- VWBPDQQZNOYORV-UHFFFAOYSA-N methyl 9-benzyl-7-(4-chlorophenyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VWBPDQQZNOYORV-UHFFFAOYSA-N 0.000 description 2
- RACLAUSVCLNLIZ-UHFFFAOYSA-N methyl 9-benzyl-7-(4-chlorophenyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(Cl)=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 RACLAUSVCLNLIZ-UHFFFAOYSA-N 0.000 description 2
- JVHMDDPXQAAJIT-UHFFFAOYSA-N methyl 9-benzyl-7-methyl-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 JVHMDDPXQAAJIT-UHFFFAOYSA-N 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
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- CKSUTZMEGFFIEN-UHFFFAOYSA-N methyl 2-[(9-benzyl-5-carbamoyl-1-methyl-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OCC(=O)OC)=CC=C(C)C=2N1CC1=CC=CC=C1 CKSUTZMEGFFIEN-UHFFFAOYSA-N 0.000 description 1
- FNUZWKBIAREHLD-UHFFFAOYSA-N methyl 2-[5-carbamoyl-2-methyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C)=CC=2N1CC1=CC=CC(C)=C1 FNUZWKBIAREHLD-UHFFFAOYSA-N 0.000 description 1
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- QFOIAPZFZSIQQU-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(pyridin-2-ylmethyl)carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=N1 QFOIAPZFZSIQQU-UHFFFAOYSA-N 0.000 description 1
- FXPAYFUKFKKWTE-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(pyridin-3-ylmethyl)carbazol-4-yl]oxyacetate Chemical compound COC(=O)COC1=CC=CC2=C1C3=C(C=CC=C3N2CC4=CN=CC=C4)C(=O)N FXPAYFUKFKKWTE-UHFFFAOYSA-N 0.000 description 1
- LCJOXWCQHMXHCK-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2,3-difluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(F)=C1F LCJOXWCQHMXHCK-UHFFFAOYSA-N 0.000 description 1
- OSDNLLDSSFQISV-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2,6-difluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=C(F)C=CC=C1F OSDNLLDSSFQISV-UHFFFAOYSA-N 0.000 description 1
- HKHJMXGFWWRYGH-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2-cyanophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C#N HKHJMXGFWWRYGH-UHFFFAOYSA-N 0.000 description 1
- XHDSTXFXSCWLSF-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2-methylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C XHDSTXFXSCWLSF-UHFFFAOYSA-N 0.000 description 1
- RKFXVRCQRMCWKM-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]-2-methylcarbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C)=CC=2N1CC1=CC=CC(F)=C1 RKFXVRCQRMCWKM-UHFFFAOYSA-N 0.000 description 1
- DQVRYWNGCRCKPY-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(3-methylphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(C)=C1 DQVRYWNGCRCKPY-UHFFFAOYSA-N 0.000 description 1
- PWRRXYOCPPBGMV-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[[2-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F PWRRXYOCPPBGMV-UHFFFAOYSA-N 0.000 description 1
- GBNZDHSCUSOAFU-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[[3-(trifluoromethoxy)phenyl]methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 GBNZDHSCUSOAFU-UHFFFAOYSA-N 0.000 description 1
- PENJYQTYSNGYMY-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[[3-(trifluoromethyl)phenyl]methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 PENJYQTYSNGYMY-UHFFFAOYSA-N 0.000 description 1
- SUUPRIMFSCSGTM-UHFFFAOYSA-N methyl 2-[9-[(2-benzylphenyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 SUUPRIMFSCSGTM-UHFFFAOYSA-N 0.000 description 1
- RYAXFUQTWZDWQK-UHFFFAOYSA-N methyl 2-[9-benzyl-5-carbamoyl-2-[4-(trifluoromethyl)phenyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=2N1CC1=CC=CC=C1 RYAXFUQTWZDWQK-UHFFFAOYSA-N 0.000 description 1
- NFZUELIAEKCBJM-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-5-pentylcyclohexen-1-yl)amino]benzoate Chemical compound C1C(CCCCC)CC(=O)C=C1NC1=CC=CC(C(=O)OC)=C1Br NFZUELIAEKCBJM-UHFFFAOYSA-N 0.000 description 1
- PQWZEKJCTAZIQS-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-5-phenylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2C=CC=CC=2)=C1Br PQWZEKJCTAZIQS-UHFFFAOYSA-N 0.000 description 1
- REGWHUMRLZDXMW-UHFFFAOYSA-N methyl 2-bromo-3-[(3-oxo-5-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C(C)C)=C1Br REGWHUMRLZDXMW-UHFFFAOYSA-N 0.000 description 1
- PPUUXYOKSGMPNS-UHFFFAOYSA-N methyl 2-bromo-3-[(6-oxo-4-propan-2-ylcyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CC=2)C(C)C)=O)=C1Br PPUUXYOKSGMPNS-UHFFFAOYSA-N 0.000 description 1
- JWLWCBBXKQCPJI-UHFFFAOYSA-N methyl 2-bromo-3-[[4-(4-chlorophenyl)-6-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CC=2)C=2C=CC(Cl)=CC=2)=O)=C1Br JWLWCBBXKQCPJI-UHFFFAOYSA-N 0.000 description 1
- MDWRQJKKKDNNLG-UHFFFAOYSA-N methyl 2-bromo-3-[[4-(hydroxymethyl)-6-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C(CC(CO)CC=2)=O)=C1Br MDWRQJKKKDNNLG-UHFFFAOYSA-N 0.000 description 1
- SRUQBVOXRAGPPX-UHFFFAOYSA-N methyl 2-bromo-3-[[5-(4-chlorophenyl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CC(=O)C=2)C=2C=CC(Cl)=CC=2)=C1Br SRUQBVOXRAGPPX-UHFFFAOYSA-N 0.000 description 1
- ZJJOZUABJIVBLZ-UHFFFAOYSA-N methyl 2-bromo-3-[[5-(hydroxymethyl)-3-oxocyclohexen-1-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CC(CO)CC(=O)C=2)=C1Br ZJJOZUABJIVBLZ-UHFFFAOYSA-N 0.000 description 1
- UOLTZUXIPBZKOS-UHFFFAOYSA-N methyl 5-bromo-5-nitrocyclohexa-1,3-diene-1-carboxylate Chemical compound COC(C=1CC(C=CC=1)([N+](=O)[O-])Br)=O UOLTZUXIPBZKOS-UHFFFAOYSA-N 0.000 description 1
- LGXOONHKKWGSAJ-UHFFFAOYSA-N methyl 5-hydroxy-7-methyl-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound CC1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C)=C1 LGXOONHKKWGSAJ-UHFFFAOYSA-N 0.000 description 1
- XDKCFHNIBOULLE-UHFFFAOYSA-N methyl 5-hydroxy-8-(naphthalen-1-ylmethyl)-9h-carbazole-4-carboxylate Chemical compound C1=CC=C2C(CC3=C4NC=5C=CC=C(C=5C4=C(O)C=C3)C(=O)OC)=CC=CC2=C1 XDKCFHNIBOULLE-UHFFFAOYSA-N 0.000 description 1
- MJMQBPVZKYFGNI-UHFFFAOYSA-N methyl 5-hydroxy-8-(pyridin-3-ylmethyl)-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CN=C1 MJMQBPVZKYFGNI-UHFFFAOYSA-N 0.000 description 1
- NFKZUNBTGGOYET-UHFFFAOYSA-N methyl 5-hydroxy-8-[[2-(trifluoromethyl)phenyl]methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1C(F)(F)F NFKZUNBTGGOYET-UHFFFAOYSA-N 0.000 description 1
- YAAFHPCNTNTEEB-UHFFFAOYSA-N methyl 5-hydroxy-8-[[3-(trifluoromethoxy)phenyl]methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(OC(F)(F)F)=C1 YAAFHPCNTNTEEB-UHFFFAOYSA-N 0.000 description 1
- GEHIQDZATHASGF-UHFFFAOYSA-N methyl 5-hydroxy-8-[[3-(trifluoromethyl)phenyl]methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C(F)(F)F)=C1 GEHIQDZATHASGF-UHFFFAOYSA-N 0.000 description 1
- VYTNZQJWZUYBQE-UHFFFAOYSA-N methyl 5-oxo-8-(pyridin-3-ylmethyl)-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CN=C1 VYTNZQJWZUYBQE-UHFFFAOYSA-N 0.000 description 1
- MUJYXSFRZGCNOZ-UHFFFAOYSA-N methyl 5-oxo-8-[(3-phenoxyphenyl)methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC(C=1)=CC=CC=1OC1=CC=CC=C1 MUJYXSFRZGCNOZ-UHFFFAOYSA-N 0.000 description 1
- IPJFPRBENXFRAM-UHFFFAOYSA-N methyl 5-oxo-8-[[2-(trifluoromethyl)phenyl]methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1C(F)(F)F IPJFPRBENXFRAM-UHFFFAOYSA-N 0.000 description 1
- FJZREPYGVSKYKK-UHFFFAOYSA-N methyl 5-oxo-8-[[3-(trifluoromethoxy)phenyl]methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(OC(F)(F)F)=C1 FJZREPYGVSKYKK-UHFFFAOYSA-N 0.000 description 1
- LVQOUDKUNKIAAY-UHFFFAOYSA-N methyl 5-oxo-8-[[3-(trifluoromethyl)phenyl]methyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(C(F)(F)F)=C1 LVQOUDKUNKIAAY-UHFFFAOYSA-N 0.000 description 1
- LLEOFYFCHLBTBJ-UHFFFAOYSA-N methyl 5-oxo-9-[[2-(trifluoromethyl)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C(F)(F)F LLEOFYFCHLBTBJ-UHFFFAOYSA-N 0.000 description 1
- YDADMHVBELPYRF-UHFFFAOYSA-N methyl 5-oxo-9-[[3-(trifluoromethoxy)phenyl]methyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC(OC(F)(F)F)=C1 YDADMHVBELPYRF-UHFFFAOYSA-N 0.000 description 1
- ZPNGYRPSWVQROU-UHFFFAOYSA-N methyl 7-(furan-2-yl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=CO1 ZPNGYRPSWVQROU-UHFFFAOYSA-N 0.000 description 1
- BHPDQZPWRCGIIW-UHFFFAOYSA-N methyl 7-methyl-8-[(3-methylphenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound CC1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(C)=C1 BHPDQZPWRCGIIW-UHFFFAOYSA-N 0.000 description 1
- SUYVZIOYJWVSJW-UHFFFAOYSA-N methyl 8-(cyclopentylmethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1CCCC1 SUYVZIOYJWVSJW-UHFFFAOYSA-N 0.000 description 1
- ZEJPSGCVVKNPPK-UHFFFAOYSA-N methyl 8-[(2,3-difluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC(F)=C1F ZEJPSGCVVKNPPK-UHFFFAOYSA-N 0.000 description 1
- OIVCMCCYGDDZIW-UHFFFAOYSA-N methyl 8-[(2,6-dichlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=C(Cl)C=CC=C1Cl OIVCMCCYGDDZIW-UHFFFAOYSA-N 0.000 description 1
- WGSFTXRHOGAUIQ-UHFFFAOYSA-N methyl 8-[(2,6-difluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=C(F)C=CC=C1F WGSFTXRHOGAUIQ-UHFFFAOYSA-N 0.000 description 1
- VTRPEPBNRKALSA-UHFFFAOYSA-N methyl 8-[(2-benzylphenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1CC1=CC=CC=C1 VTRPEPBNRKALSA-UHFFFAOYSA-N 0.000 description 1
- IPMOWRZNUJLVIJ-UHFFFAOYSA-N methyl 8-[(2-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1F IPMOWRZNUJLVIJ-UHFFFAOYSA-N 0.000 description 1
- PSUWMGDNEDHTRX-UHFFFAOYSA-N methyl 8-[(2-fluorophenyl)methyl]-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1F PSUWMGDNEDHTRX-UHFFFAOYSA-N 0.000 description 1
- LLJBLIUDIZNGAE-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-5-hydroxy-7-methyl-9h-carbazole-4-carboxylate Chemical compound CC1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1 LLJBLIUDIZNGAE-UHFFFAOYSA-N 0.000 description 1
- UOJWZSYHSNVSCI-UHFFFAOYSA-N methyl 8-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]-9h-carbazole-4-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1 UOJWZSYHSNVSCI-UHFFFAOYSA-N 0.000 description 1
- FMMQJOKFRIRBOQ-UHFFFAOYSA-N methyl 8-benzyl-5-hydroxy-7-methyl-9h-carbazole-4-carboxylate Chemical compound CC1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1 FMMQJOKFRIRBOQ-UHFFFAOYSA-N 0.000 description 1
- BHDFQVHWKNUUBP-UHFFFAOYSA-N methyl 8-benzyl-5-oxo-7-[4-(trifluoromethyl)phenyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=C1 BHDFQVHWKNUUBP-UHFFFAOYSA-N 0.000 description 1
- GKDFGTVUWFSFSG-UHFFFAOYSA-N methyl 9-[(2,6-dichlorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl GKDFGTVUWFSFSG-UHFFFAOYSA-N 0.000 description 1
- NQJOZJJMFTYKAS-UHFFFAOYSA-N methyl 9-[(2,6-difluorophenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=C(F)C=CC=C1F NQJOZJJMFTYKAS-UHFFFAOYSA-N 0.000 description 1
- WBHWSVHRGPRIAZ-UHFFFAOYSA-N methyl 9-[(2-methylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1C WBHWSVHRGPRIAZ-UHFFFAOYSA-N 0.000 description 1
- HCGFOPKRNGMOKA-UHFFFAOYSA-N methyl 9-[(3,5-dimethylphenyl)methyl]-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC(C)=CC(C)=C1 HCGFOPKRNGMOKA-UHFFFAOYSA-N 0.000 description 1
- UWKQMTAHLXBKDM-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]carbazole-4-carboxylate Chemical compound C12=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 UWKQMTAHLXBKDM-UHFFFAOYSA-N 0.000 description 1
- TUFAGSKTLXPHPK-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-[4-(trifluoromethyl)phenyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3C=CC(=CC=3)C(F)(F)F)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 TUFAGSKTLXPHPK-UHFFFAOYSA-N 0.000 description 1
- CATQTVAHJGQIGC-UHFFFAOYSA-N methyl 9-benzyl-7-(hydroxymethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(CO)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 CATQTVAHJGQIGC-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NPKYYJGDHWBTSU-UHFFFAOYSA-N n-benzyl-3,5-dimethoxyaniline Chemical compound COC1=CC(OC)=CC(NCC=2C=CC=CC=2)=C1 NPKYYJGDHWBTSU-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- KQOUGLLWYHJABD-UHFFFAOYSA-M sodium;2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxyacetate Chemical compound [Na+].C=1C(OC)=CC(OCC([O-])=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 KQOUGLLWYHJABD-UHFFFAOYSA-M 0.000 description 1
- DDIVPTBAYACPPE-UHFFFAOYSA-M sodium;2-[(9-benzyl-5-carbamoyl-2-methoxy-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound [Na+].C12=CC(OC)=CC(OCC([O-])=O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 DDIVPTBAYACPPE-UHFFFAOYSA-M 0.000 description 1
- NAMUOZQPVQONTP-UHFFFAOYSA-M sodium;2-[5-carbamoyl-9-[(2,6-difluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound [Na+].C12=CC=CC(OCC([O-])=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(F)C=CC=C1F NAMUOZQPVQONTP-UHFFFAOYSA-M 0.000 description 1
- BCFCHSGVZFVWHL-UHFFFAOYSA-M sodium;2-[9-[(2-benzylphenyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetate Chemical compound [Na+].C12=CC=CC(OCC([O-])=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1CC1=CC=CC=C1 BCFCHSGVZFVWHL-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- DGBCEDABANLFFU-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(2-chlorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC1=CC=CC=C1Cl DGBCEDABANLFFU-UHFFFAOYSA-N 0.000 description 1
- AMQKSDOYCMKXIW-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(3-chlorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC1=CC=CC(Cl)=C1 AMQKSDOYCMKXIW-UHFFFAOYSA-N 0.000 description 1
- RXOVTHCDTPBQBX-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(3-fluorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC1=CC=CC(F)=C1 RXOVTHCDTPBQBX-UHFFFAOYSA-N 0.000 description 1
- PQLOIVOTHAHYNC-UHFFFAOYSA-N tert-butyl 2-[5-carbamoyl-9-[(3-phenoxyphenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC(C)(C)C)=CC=CC=2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 PQLOIVOTHAHYNC-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6232898A | 1998-04-17 | 1998-04-17 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO991821D0 NO991821D0 (no) | 1999-04-16 |
NO991821L NO991821L (no) | 1999-10-18 |
NO314400B1 true NO314400B1 (no) | 2003-03-17 |
Family
ID=22041763
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19991822A NO312240B1 (no) | 1998-04-17 | 1999-04-16 | Substituerte tricykliske forbindelser, preparater inneholdende forbindelsene samt forbindelsenes anvendelse |
NO19991821A NO314400B1 (no) | 1998-04-17 | 1999-04-16 | Substituerte tricykliske forbindelser |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19991822A NO312240B1 (no) | 1998-04-17 | 1999-04-16 | Substituerte tricykliske forbindelser, preparater inneholdende forbindelsene samt forbindelsenes anvendelse |
Country Status (30)
Country | Link |
---|---|
EP (2) | EP0950657B1 (ja) |
JP (2) | JP4435330B2 (ja) |
KR (2) | KR100586761B1 (ja) |
CN (1) | CN1149193C (ja) |
AR (2) | AR018186A1 (ja) |
AT (2) | ATE268756T1 (ja) |
AU (2) | AU753436B2 (ja) |
BR (2) | BR9901279A (ja) |
CA (2) | CA2269262A1 (ja) |
CO (2) | CO5011054A1 (ja) |
CZ (2) | CZ136999A3 (ja) |
DE (2) | DE69918590T2 (ja) |
DK (1) | DK0950657T3 (ja) |
DZ (1) | DZ2769A1 (ja) |
EA (2) | EA002816B1 (ja) |
ES (2) | ES2226286T3 (ja) |
HU (2) | HUP9901220A3 (ja) |
ID (2) | ID23287A (ja) |
IL (2) | IL129483A0 (ja) |
NO (2) | NO312240B1 (ja) |
NZ (3) | NZ335251A (ja) |
PE (2) | PE20000432A1 (ja) |
PL (2) | PL332566A1 (ja) |
PT (1) | PT950657E (ja) |
SG (2) | SG81977A1 (ja) |
SI (1) | SI0950657T1 (ja) |
TR (2) | TR199900853A2 (ja) |
TW (1) | TWI238160B (ja) |
YU (2) | YU19199A (ja) |
ZA (2) | ZA992771B (ja) |
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AU9123198A (en) * | 1997-08-28 | 1999-03-16 | Eli Lilly And Company | Method for treatment of non-rheumatoid athritis |
DZ2769A1 (fr) * | 1998-04-17 | 2003-12-01 | Lilly Co Eli | Composés tricycliques substitués. |
JP2002542148A (ja) * | 1998-12-21 | 2002-12-10 | イーライ・リリー・アンド・カンパニー | 敗血症の処置のための組み合わせ療法 |
EP1202963B1 (en) * | 1999-07-19 | 2007-01-03 | Eli Lilly And Company | Spla2 inhibitors |
US6706752B1 (en) | 1999-07-19 | 2004-03-16 | Eli Lilly And Company | sPLA2 inhibitors |
ES2294003T3 (es) * | 2000-06-29 | 2008-04-01 | Anthera Pharmaceuticals, Inc. | Remedios contra el cancer. |
AU2001267825A1 (en) | 2000-06-29 | 2002-01-08 | Shionogi And Co., Ltd. | Remedies for cirrhosis |
WO2002000257A1 (fr) * | 2000-06-29 | 2002-01-03 | Shionogi & Co., Ltd. | Remedes a la maladie d'alzheimer |
WO2002005796A2 (en) * | 2000-07-14 | 2002-01-24 | Eli Lilly And Company | Use of a spla2 inhibitor for the treatment of sepsis |
EP1345898A2 (en) | 2000-12-18 | 2003-09-24 | Eli Lilly And Company | Teracyclic carbazole derivates and their use as spla2 inhibitors |
ATE353876T1 (de) * | 2001-03-28 | 2007-03-15 | Lilly Co Eli | Substituierte carbazole als inhibitoren von spla2 |
AUPS282602A0 (en) | 2002-06-07 | 2002-06-27 | Garvan Institute Of Medical Research | Method of inhibiting cell proliferation |
DE10249055A1 (de) | 2002-10-22 | 2004-05-06 | Bayer Cropscience Ag | 2-Phenyl-2-substituierte-1,3-diketone |
JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
EP1988098A1 (en) * | 2007-04-27 | 2008-11-05 | AEterna Zentaris GmbH | Novel Tetrahydrocarbazole Derivatives as Ligands of G-protein Coupled Receptors |
KR20100124771A (ko) | 2008-03-26 | 2010-11-29 | 다이이찌 산쿄 가부시키가이샤 | 신규 테트라하이드로이소퀴놀린 유도체 |
JP5637982B2 (ja) | 2008-04-09 | 2014-12-10 | インフィニティー ファーマシューティカルズ, インコーポレイテッド | 脂肪酸アミド加水分解酵素の阻害剤 |
EP2379538A4 (en) | 2009-01-22 | 2013-01-02 | Orchid Res Lab Ltd | HETEROCYCLIC COMPOUNDS AS A PHOSOPHODIESTERASE HEMMER |
EP2417115A4 (en) | 2009-04-07 | 2012-10-31 | Infinity Pharmaceuticals Inc | FATTY ACID AMIDE HYDROLASE INHIBITORS |
AU2010234445A1 (en) | 2009-04-07 | 2011-11-03 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
KR101888026B1 (ko) | 2010-02-03 | 2018-08-13 | 인피니티 파마슈티컬스, 인코포레이티드 | 지방산 아미드 하이드롤라제 저해제 |
AR088377A1 (es) | 2011-10-20 | 2014-05-28 | Siena Biotech Spa | Proceso para la preparacion de 6-cloro-2,3,4,9-tetrahidro-1h-carbazol-1-carboxamida y compuestos intermedios de esta |
CN102816107B (zh) * | 2012-08-20 | 2015-06-03 | 东南大学 | 咔唑衍生物及其制备方法与用途 |
BR112015012138A2 (pt) | 2012-11-30 | 2017-07-11 | Ge Healthcare Ltd | composição, método para obtenção de uma composição, método de formação de imagem in vivo, e, kit |
KR20150088803A (ko) * | 2012-11-30 | 2015-08-03 | 지이 헬쓰케어 리미티드 | 트리시클릭 인돌을 생성하는 아연 할라이드 매개 고리화 방법 |
WO2016116527A1 (de) * | 2015-01-20 | 2016-07-28 | Cynora Gmbh | Organische moleküle, insbesondere zur verwendung in optoelektronischen bauelementen |
CN108707104A (zh) * | 2018-08-07 | 2018-10-26 | 北京恒信卓元科技有限公司 | 2-氯-1h-咔唑-1,4(9h)-二酮的合成方法 |
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US5420289A (en) * | 1989-10-27 | 1995-05-30 | American Home Products Corporation | Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole-alkanoic acid derivatives as inhibitors of PLA2 and lipoxygenase |
PT95692A (pt) * | 1989-10-27 | 1991-09-13 | American Home Prod | Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase |
CA2110514A1 (en) * | 1991-07-05 | 1993-01-21 | Raymond Baker | Aromatic compounds, pharmaceutical compositions containing them and their use in therapy |
MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
IL109311A0 (en) * | 1993-04-16 | 1994-07-31 | Lilly Co Eli | 1H-indole-3-acetamide sPla2 inhibitors |
IL109309A (en) * | 1993-04-16 | 2000-06-29 | Lilly Co Eli | 1-H-indole-3-acetic acid hydrazide SPLA2 inhibitors and pharmaceutical compositions containing them |
CA2179678A1 (en) * | 1995-06-23 | 1996-12-24 | Michael Edward Flaugh | 6-substituted-1,2,3,4-tetrahydro-9h-carbazoles and 7-substituted-10h-cyclohepta¬7,6-b| indoles |
US6160175A (en) * | 1995-12-13 | 2000-12-12 | Eli Lilly And Company | Naphthyl acetamides as sPLA2 inhibitors |
IL129481A0 (en) * | 1996-10-30 | 2000-02-29 | Lilly Co Eli | Substituted tricyclics |
JP2001517707A (ja) * | 1997-09-26 | 2001-10-09 | イーライ・リリー・アンド・カンパニー | 嚢胞性繊維症の処置方法 |
CA2310250A1 (en) * | 1997-11-14 | 1999-05-27 | August Masaru Watanabe | Treatment for alzheimer's disease |
DZ2769A1 (fr) * | 1998-04-17 | 2003-12-01 | Lilly Co Eli | Composés tricycliques substitués. |
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