DE69917833T2 - Substituierte Karbazole, Verfahren zu ihrer Herstellung und ihre Verwendung als sPLA2- Inhibitoren - Google Patents

Info

Publication number

DE69917833T2

DE69917833T2 DE69917833T DE69917833T DE69917833T2 DE 69917833 T2 DE69917833 T2 DE 69917833T2 DE 69917833 T DE69917833 T DE 69917833T DE 69917833 T DE69917833 T DE 69917833T DE 69917833 T2 DE69917833 T2 DE 69917833T2

Authority

DE

Germany

Prior art keywords

methyl

oxyacetic acid

carbamoylcarbazol

carbamoyl

benzyl

Prior art date

1998-04-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

Links

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• 238000002360 preparation method Methods 0.000 title description 195
• 238000000034 method Methods 0.000 title description 52
• 239000003112 inhibitor Substances 0.000 title description 5
• 230000008569 process Effects 0.000 title description 4
• 102000005473 Secretory Phospholipases A2 Human genes 0.000 title 1
• 108010031873 Secretory Phospholipases A2 Proteins 0.000 title 1
• 150000001716 carbazoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 148
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
• 239000002253 acid Substances 0.000 claims description 45
• -1 1H-tetrazol-5-ylmethyl Chemical group 0.000 claims description 42
• 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 23
• 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 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 206010003246 arthritis Diseases 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 11
• 229940002612 prodrug Drugs 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 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 9
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
• 201000010099 disease Diseases 0.000 claims description 9
• 230000000694 effects Effects 0.000 claims description 9
• 239000000194 fatty acid Substances 0.000 claims description 9
• 229930195729 fatty acid Natural products 0.000 claims description 9
• 150000004665 fatty acids Chemical class 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 8
• 206010040070 Septic Shock Diseases 0.000 claims description 8
• 229940114079 arachidonic acid Drugs 0.000 claims description 8
• 235000021342 arachidonic acid Nutrition 0.000 claims description 8
• 230000001404 mediated effect Effects 0.000 claims description 8
• 150000004702 methyl esters Chemical class 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 230000036303 septic shock Effects 0.000 claims description 8
• 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 7
• 206010006451 bronchitis Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• HTSWKDOXMSFQPB-UHFFFAOYSA-N 8-ethoxy-7-methoxy-9H-carbazole-4-carboxamide Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1C(OCC)=C(OC)C=C2 HTSWKDOXMSFQPB-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 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 6
• 208000012659 Joint disease Diseases 0.000 claims description 6
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 208000014674 injury Diseases 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 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
• 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 claims description 5
• 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 5
• 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 5
• 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 claims description 5
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 230000035939 shock Effects 0.000 claims description 5
• 239000012453 solvate 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
• 230000008733 trauma Effects 0.000 claims description 5
• 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 4
• 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
• CXRULWWTHRSJSP-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-1-chloro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound NC(=O)C1CCCC2=C1C1=C(OCC(O)=O)C=CC(Cl)=C1N2CC1=CC=CC=C1 CXRULWWTHRSJSP-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 claims description 4
• 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 4
• UIMGRPXPFBJHJJ-UHFFFAOYSA-N 2-[5-carbamoyl-9-[(3-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(Cl)=C1 UIMGRPXPFBJHJJ-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 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
• 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 claims description 4
• PYSFKPLKDUHZAJ-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(propoxymethyl)carbazol-4-yl]oxyacetic acid Chemical compound C=1C(COCCC)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 PYSFKPLKDUHZAJ-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• PTOFERBJZMNRQD-UHFFFAOYSA-N 9-benzyl-5-(cyanomethoxy)-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(OCC#N)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 PTOFERBJZMNRQD-UHFFFAOYSA-N 0.000 claims description 4
• 208000036487 Arthropathies Diseases 0.000 claims description 4
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• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
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• GELSNBZFFJBDDC-UHFFFAOYSA-N 1-ethoxy-7-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide Chemical compound C(C)OC1CCC(C=2C3=CC=C(C=C3NC1=2)OC)C(=O)N GELSNBZFFJBDDC-UHFFFAOYSA-N 0.000 claims description 3
• LOEUKRWGLDWONT-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-1-fluorocarbazol-4-yl)oxyacetic acid Chemical compound C12=C(F)C=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 LOEUKRWGLDWONT-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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
• 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 claims description 3
• LBFYBHJYZNSGAA-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-thiophen-2-ylcarbazol-4-yl)oxyacetic acid Chemical compound C12=CC(C=3SC=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 LBFYBHJYZNSGAA-UHFFFAOYSA-N 0.000 claims description 3
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• VZOLOKPKXHOJRH-UHFFFAOYSA-N 2-[5-carbamoyl-9-(pyridin-2-ylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=N1 VZOLOKPKXHOJRH-UHFFFAOYSA-N 0.000 claims description 3
• OJRRWHBSOZGENJ-UHFFFAOYSA-N 2-[5-carbamoyl-9-(pyridin-3-ylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CN=C1 OJRRWHBSOZGENJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 3
• 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 3
• ISRGSXVOKPRVIP-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-4-carbohydrazide Chemical compound C12=CC(OC)=CC(OC)=C2C=2C(C(=O)NN)CCCC=2N1CC1=CC=CC=C1 ISRGSXVOKPRVIP-UHFFFAOYSA-N 0.000 claims description 3
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• NDTBXYQGBBMXLW-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[3-(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(C(F)(F)F)=C1 NDTBXYQGBBMXLW-UHFFFAOYSA-N 0.000 claims description 2
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• 206010016207 Familial Mediterranean fever Diseases 0.000 claims description 2
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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• LFFIJRJGKBSELO-FQEVSTJZSA-O diheptanoyl sn-dithiophosphatidylcholine Chemical compound CCCCCCC(=O)SC[C@H](COP(O)(=O)OCC[N+](C)(C)C)SC(=O)CCCCCC LFFIJRJGKBSELO-FQEVSTJZSA-O 0.000 description 3
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• VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
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• 239000001257 hydrogen Substances 0.000 description 3
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• 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 description 3
• 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 3
• 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 3
• NFMFPZIANORNMT-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-(naphthalen-1-ylmethyl)carbazol-4-yl]oxyacetate Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C2=CC=CC(C(N)=O)=C2C2=C1C=CC=C2OCC(=O)OC NFMFPZIANORNMT-UHFFFAOYSA-N 0.000 description 3
• 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 3
• JKVDHSLQLFKKET-UHFFFAOYSA-N methyl 2-[5-carbamoyl-9-[(2,6-dichlorophenyl)methyl]carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl JKVDHSLQLFKKET-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 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
• 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 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
• 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 3
• 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 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
• 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 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
• OSLFZPFTEOMXPS-UHFFFAOYSA-N methyl 5-oxo-7-[4-(trifluoromethyl)phenyl]-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=C(C(F)(F)F)C=C1 OSLFZPFTEOMXPS-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 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 3
• YLACHINBXBKUBX-UHFFFAOYSA-N methyl 9-(cyclohexylmethyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCCC1 YLACHINBXBKUBX-UHFFFAOYSA-N 0.000 description 3
• KISUBDQINFFPAU-UHFFFAOYSA-N methyl 9-(cyclohexylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCCC1 KISUBDQINFFPAU-UHFFFAOYSA-N 0.000 description 3
• HQXQUBSVHRBQAC-UHFFFAOYSA-N methyl 9-(cyclopentylmethyl)-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCC1 HQXQUBSVHRBQAC-UHFFFAOYSA-N 0.000 description 3
• QZRSFEAXAOKXCG-UHFFFAOYSA-N methyl 9-(cyclopentylmethyl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CCCC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1CCCC1 QZRSFEAXAOKXCG-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 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 3
• 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 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
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• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• JTLVTCUZWKZOKJ-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-1-chlorocarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=C(Cl)C=2N1CC1=CC=CC=C1 JTLVTCUZWKZOKJ-UHFFFAOYSA-N 0.000 description 2
• IHPUOZMXJDHIBO-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-1-fluorocarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=C(F)C=2N1CC1=CC=CC=C1 IHPUOZMXJDHIBO-UHFFFAOYSA-N 0.000 description 2
• MHEOLKMEADRTLY-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC=C(C)C=2N1CC1=CC=CC=C1 MHEOLKMEADRTLY-UHFFFAOYSA-N 0.000 description 2
• JZFFXEXJIQWGBE-UHFFFAOYSA-N methyl 2-[(9-benzyl-5-carbamoyl-1-chloro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OCC(=O)OC)=CC=C(Cl)C=2N1CC1=CC=CC=C1 JZFFXEXJIQWGBE-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 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
• 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
• 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 2
• 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 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
• 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
• 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
• 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 2
• 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 2
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• 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
• XEGIWWBBRUTRBC-UHFFFAOYSA-N methyl 2-[9-benzyl-5-carbamoyl-2-(4-chlorophenyl)carbazol-4-yl]oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C=3C=CC(Cl)=CC=3)=CC=2N1CC1=CC=CC=C1 XEGIWWBBRUTRBC-UHFFFAOYSA-N 0.000 description 1
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• 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 1
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• CGDJPSJNVXTJGI-UHFFFAOYSA-N methyl 5-oxo-7-thiophen-2-yl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=CS1 CGDJPSJNVXTJGI-UHFFFAOYSA-N 0.000 description 1
• LALRTWKTWDFFIX-UHFFFAOYSA-N methyl 7-(4-chlorophenyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=C(Cl)C=C1 LALRTWKTWDFFIX-UHFFFAOYSA-N 0.000 description 1
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• 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 description 1
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• 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
• 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 1
• RVEOHBHKGYBPIX-UHFFFAOYSA-N methyl 9-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydrocarbazole-4-carboxylate Chemical compound FC(C=1C=C(C=CC1)CN1C2=CC=CC(=C2C=2C=CCCC12)C(=O)OC)(F)F RVEOHBHKGYBPIX-UHFFFAOYSA-N 0.000 description 1
• YMPIZZIWCULYFJ-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-[tri(propan-2-yl)silyloxymethyl]carbazole-4-carboxylate Chemical compound C12=CC(CO[Si](C(C)C)(C(C)C)C(C)C)=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 YMPIZZIWCULYFJ-UHFFFAOYSA-N 0.000 description 1
• FNOKDIQYOIJIKH-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxy-7-pentylcarbazole-4-carboxylate Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(=O)OC)C=CC=C22)C=1N2CC1=CC=CC=C1 FNOKDIQYOIJIKH-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• HDDOVCMVRWRDTE-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-[tri(propan-2-yl)silyloxymethyl]-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(CO[Si](C(C)C)(C(C)C)C(C)C)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 HDDOVCMVRWRDTE-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 1
• FEWNLDUNLFOTNW-UHFFFAOYSA-N methyl 9-benzyl-5-oxo-7-thiophen-2-yl-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3SC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 FEWNLDUNLFOTNW-UHFFFAOYSA-N 0.000 description 1
• 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 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 description 1
• IPCMTRGVYIHEOW-UHFFFAOYSA-N methyl 9-benzyl-7-(furan-2-yl)-5-oxo-7,8-dihydro-6h-carbazole-4-carboxylate Chemical compound C1=2CC(C=3OC=CC=3)CC(=O)C=2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 IPCMTRGVYIHEOW-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
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• 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
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• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
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