NO314400B1 - Substituerte tricykliske forbindelser - Google Patents

Substituerte tricykliske forbindelser Download PDF

Info

Publication number: NO314400B1
Authority: NO; Norway
Prior art keywords: methyl; hydroxy; oxyacetic acid; carbamoyl; benzyl
Prior art date: 1998-04-17

Application number

NO19991821A

Other languages

English (en)

Norwegian (no)

Other versions

NO991821L (no

NO991821D0 (no

Inventor

Benjamin Alan Anderson

Nicholas James Bach

Jolie Anne Bastian

Nancy Kay Harn

Richard Waltz Harper

Gary Alan Hite

Michael Dean Kinnick

Ho-Shen Lin

Richard James Loncharich

Iii John Mcneill Mcgill

Edward David Mihelich

Jr John Michael Morin

Michael Leroy Phillips

Michael Enrico Richett

Daniel Jon Sall

Jason Scott Sawyer

Richard Walter Schevitz

Robert Theodore Vasileff

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1998-04-17

Filing date

1999-04-16

Publication date

2003-03-17

1999-04-16 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1999-04-16 Publication of NO991821D0 publication Critical patent/NO991821D0/no

1999-10-18 Publication of NO991821L publication Critical patent/NO991821L/no

2003-03-17 Publication of NO314400B1 publication Critical patent/NO314400B1/no

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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PTMODKWZACRSDF-UHFFFAOYSA-N 8-chloro-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound N1C2=C(Cl)C=CC(O)=C2C2=C1C=CC=C2C(=O)N PTMODKWZACRSDF-UHFFFAOYSA-N 0.000 claims description 2
RLYWCMMWDHISRY-UHFFFAOYSA-N 9-benzyl-5-hydroxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound OC(=O)C1CCCC2=C1C1=C(O)C=CC=C1N2CC1=CC=CC=C1 RLYWCMMWDHISRY-UHFFFAOYSA-N 0.000 claims description 2
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PSDHESHUDOJGBM-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-phenylcarbazole-4-carboxamide Chemical compound C12=CC(C=3C=CC=CC=3)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 PSDHESHUDOJGBM-UHFFFAOYSA-N 0.000 claims description 2
HQGXELDGYSMEAM-UHFFFAOYSA-N 9-benzyl-5-hydroxy-8-methylcarbazole-4-carboxamide Chemical compound CC1=CC=C(O)C(C2=C(C(N)=O)C=CC=C22)=C1N2CC1=CC=CC=C1 HQGXELDGYSMEAM-UHFFFAOYSA-N 0.000 claims description 2
GWCJQGNSWFHLCA-UHFFFAOYSA-N 9-benzyl-7-(furan-2-yl)-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC(C=3OC=CC=3)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 GWCJQGNSWFHLCA-UHFFFAOYSA-N 0.000 claims description 2
CVMPWOFIAOZART-UHFFFAOYSA-N 9-benzyl-8-chloro-5-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OC)=CC=C(Cl)C=2N1CC1=CC=CC=C1 CVMPWOFIAOZART-UHFFFAOYSA-N 0.000 claims description 2
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206010003274 Arthritis viral Diseases 0.000 claims description 2
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 claims description 2
201000003883 Cystic fibrosis Diseases 0.000 claims description 2
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201000005569 Gout Diseases 0.000 claims description 2
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201000004331 Henoch-Schoenlein purpura Diseases 0.000 claims description 2
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208000002240 Tennis Elbow Diseases 0.000 claims description 2
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201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
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239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
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208000034737 hemoglobinopathy Diseases 0.000 claims description 2
208000020346 hyperlipoproteinemia Diseases 0.000 claims description 2
201000006362 hypersensitivity vasculitis Diseases 0.000 claims description 2
208000015446 immunoglobulin a vasculitis Diseases 0.000 claims description 2
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201000004990 juvenile ankylosing spondylitis Diseases 0.000 claims description 2
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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 claims description 2
RIOYVNUQLQDHMC-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-2-phenylcarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(C=3C=CC=CC=3)=CC=2N1CC1=CC=CC=C1 RIOYVNUQLQDHMC-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
KYNVMTIOCYUILP-UHFFFAOYSA-N methyl 5-hydroxy-8-[(2-methylphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1C KYNVMTIOCYUILP-UHFFFAOYSA-N 0.000 claims description 2
JYKZPQXYQAZBDW-UHFFFAOYSA-N methyl 5-hydroxy-8-[(3-methylphenyl)methyl]-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C)=C1 JYKZPQXYQAZBDW-UHFFFAOYSA-N 0.000 claims description 2
KXTFYUZQWPILHJ-UHFFFAOYSA-N methyl 5-oxo-7-phenyl-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1C(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2CC1C1=CC=CC=C1 KXTFYUZQWPILHJ-UHFFFAOYSA-N 0.000 claims description 2
QMZHGZNTWCWPKL-UHFFFAOYSA-N methyl 5-oxo-8-(pyridin-2-ylmethyl)-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1=CC=CC=N1 QMZHGZNTWCWPKL-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
GEZZVZOTGGOQOF-UHFFFAOYSA-N methyl 8-(cyclohexylmethyl)-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1CCCCC1 GEZZVZOTGGOQOF-UHFFFAOYSA-N 0.000 claims description 2
HCKOATMSEPUWTK-UHFFFAOYSA-N methyl 8-(cyclohexylmethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1CC(=O)C=2C=3C(C(=O)OC)=CC=CC=3NC=2C1CC1CCCCC1 HCKOATMSEPUWTK-UHFFFAOYSA-N 0.000 claims description 2
KFDVBCLAXUUVGA-UHFFFAOYSA-N methyl 8-(naphthalen-1-ylmethyl)-5-oxo-6,7,8,9-tetrahydrocarbazole-4-carboxylate Chemical compound C1=CC=C2C(CC3C=4NC=5C=CC=C(C=5C=4C(=O)CC3)C(=O)OC)=CC=CC2=C1 KFDVBCLAXUUVGA-UHFFFAOYSA-N 0.000 claims description 2
QYLCAWWPPICHHY-UHFFFAOYSA-N methyl 8-[(2,3-difluorophenyl)methyl]-5-hydroxy-9H-carbazole-4-carboxylate Chemical compound FC1=C(C=CC=C1F)CC1=CC=C(C=2C3=C(C=CC=C3NC12)C(=O)OC)O QYLCAWWPPICHHY-UHFFFAOYSA-N 0.000 claims description 2
ZRCUHIXGCNCATB-UHFFFAOYSA-N methyl 8-[(2-benzylphenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1CC1=CC=CC=C1 ZRCUHIXGCNCATB-UHFFFAOYSA-N 0.000 claims description 2
CMTJUHAPNXOKMH-UHFFFAOYSA-N methyl 8-[(2-chlorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1Cl CMTJUHAPNXOKMH-UHFFFAOYSA-N 0.000 claims description 2
QMOMLSDZBQSOKC-UHFFFAOYSA-N methyl 8-[(2-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC=C1C#N QMOMLSDZBQSOKC-UHFFFAOYSA-N 0.000 claims description 2
PJNHGSLSWGGCJL-UHFFFAOYSA-N methyl 8-[(2-cyanophenyl)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=C1C#N PJNHGSLSWGGCJL-UHFFFAOYSA-N 0.000 claims description 2
HHQJXNGKINMDTB-UHFFFAOYSA-N methyl 8-[(2-methylphenyl)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=C1C HHQJXNGKINMDTB-UHFFFAOYSA-N 0.000 claims description 2
MZRRZOWIEKWCDJ-UHFFFAOYSA-N methyl 8-[(3,5-dimethylphenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC(C)=CC(C)=C1 MZRRZOWIEKWCDJ-UHFFFAOYSA-N 0.000 claims description 2
RWQODNUXKYOHEQ-UHFFFAOYSA-N methyl 8-[(3,5-dimethylphenyl)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(C)=CC(C)=C1 RWQODNUXKYOHEQ-UHFFFAOYSA-N 0.000 claims description 2
QIBDGTAYYPRPBS-UHFFFAOYSA-N methyl 8-[(3-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(Cl)=C1 QIBDGTAYYPRPBS-UHFFFAOYSA-N 0.000 claims description 2
UTVOHZWCZSBNHV-UHFFFAOYSA-N methyl 8-[(3-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(C#N)=C1 UTVOHZWCZSBNHV-UHFFFAOYSA-N 0.000 claims description 2
PAMLAIMRXGQXDB-UHFFFAOYSA-N methyl 8-[(3-cyanophenyl)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(C#N)=C1 PAMLAIMRXGQXDB-UHFFFAOYSA-N 0.000 claims description 2
OIDBVEJMWHVFOC-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxylate Chemical compound C1=CC(O)=C2C=3C(C(=O)OC)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1 OIDBVEJMWHVFOC-UHFFFAOYSA-N 0.000 claims description 2
JDFGJZQZTOSUOE-UHFFFAOYSA-N methyl 8-[(3-fluorophenyl)methyl]-7-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(F)=C1 JDFGJZQZTOSUOE-UHFFFAOYSA-N 0.000 claims description 2
MYSACBDANIYOTO-UHFFFAOYSA-N methyl 8-[(3-iodophenyl)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(I)=C1 MYSACBDANIYOTO-UHFFFAOYSA-N 0.000 claims description 2
QPCSWIGFQVWSDE-UHFFFAOYSA-N methyl 8-benzyl-7-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=C1 QPCSWIGFQVWSDE-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
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 claims description 2
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 claims description 2
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 claims description 2
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208000011580 syndromic disease Diseases 0.000 claims description 2
210000002437 synoviocyte Anatomy 0.000 claims description 2
230000009885 systemic effect Effects 0.000 claims description 2
230000003156 vasculitic effect Effects 0.000 claims description 2
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 1
YFTJSPAAYBFQNI-UHFFFAOYSA-N 2-[5-carbamoyl-9-(cyclopentylmethyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1CCCC1 YFTJSPAAYBFQNI-UHFFFAOYSA-N 0.000 claims 1
MFIXRNRZGPNXSH-UHFFFAOYSA-N 5-hydroxy-8-[(2-methylphenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound CC1=CC=CC=C1CC1=CC=C(O)C2=C1NC1=CC=CC(C(N)=O)=C21 MFIXRNRZGPNXSH-UHFFFAOYSA-N 0.000 claims 1
HZXRZFGEOLILIJ-UHFFFAOYSA-N 5-hydroxy-8-[(3-iodophenyl)methyl]-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(I)=C1 HZXRZFGEOLILIJ-UHFFFAOYSA-N 0.000 claims 1
QOLJQZMMHKRZMO-UHFFFAOYSA-N 8-[(2,3-difluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1F QOLJQZMMHKRZMO-UHFFFAOYSA-N 0.000 claims 1
LARGYAUQGJESEN-UHFFFAOYSA-N 8-[(2-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC=C1C#N LARGYAUQGJESEN-UHFFFAOYSA-N 0.000 claims 1
BHAJYOWNSKSYJB-UHFFFAOYSA-N 8-[(3-cyanophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(C#N)=C1 BHAJYOWNSKSYJB-UHFFFAOYSA-N 0.000 claims 1
DCDSYOQEGRYCNZ-UHFFFAOYSA-N 8-[(3-fluorophenyl)methyl]-5-hydroxy-9h-carbazole-4-carboxamide Chemical compound C1=CC(O)=C2C=3C(C(=O)N)=CC=CC=3NC2=C1CC1=CC=CC(F)=C1 DCDSYOQEGRYCNZ-UHFFFAOYSA-N 0.000 claims 1
JPNCLCUFHSHYHS-UHFFFAOYSA-N 9-benzyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound C12=CC(OC)=CC(OC)=C2C=2C(C(O)=O)CCCC=2N1CC1=CC=CC=C1 JPNCLCUFHSHYHS-UHFFFAOYSA-N 0.000 claims 1
HKMIHHJQMSJGKA-UHFFFAOYSA-N 9-benzyl-7-methoxy-5-(2h-tetrazol-5-ylmethoxy)carbazole-4-carboxamide Chemical compound C=1C=CC=CC=1CN1C2=CC=CC(C(N)=O)=C2C=2C1=CC(OC)=CC=2OCC1=NN=NN1 HKMIHHJQMSJGKA-UHFFFAOYSA-N 0.000 claims 1
GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 claims 1
206010040047 Sepsis Diseases 0.000 claims 1
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims 1
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 claims 1
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
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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
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
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238000004440 column chromatography Methods 0.000 description 80
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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
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238000000034 method Methods 0.000 description 49
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239000012267 brine Substances 0.000 description 45
239000002904 solvent Substances 0.000 description 44
239000010410 layer Substances 0.000 description 43
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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
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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
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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
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235000011181 potassium carbonates Nutrition 0.000 description 25
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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
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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
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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
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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
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239000002168 alkylating agent Substances 0.000 description 7
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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
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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
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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
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239000002002 slurry Substances 0.000 description 5
229940001593 sodium carbonate Drugs 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
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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
FJGZTTJYTQDFHV-UHFFFAOYSA-N 9-benzyl-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 FJGZTTJYTQDFHV-UHFFFAOYSA-N 0.000 description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
125000005037 alkyl phenyl group Chemical group 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
238000011097 chromatography purification Methods 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
KGGODVNXMMAXAK-UHFFFAOYSA-N ethene;hexane Chemical class C=C.C=C.CCCCCC KGGODVNXMMAXAK-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
PHPULYFYWVNCCX-UHFFFAOYSA-N methyl 2-chloro-3-[(3-oxocyclohexen-1-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2CCCC(=O)C=2)=C1Cl PHPULYFYWVNCCX-UHFFFAOYSA-N 0.000 description 4
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 4
VVVSZKHAZFQJHB-UHFFFAOYSA-N methyl 9-benzyl-5-hydroxycarbazole-4-carboxylate Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)OC)=CC=CC=2N1CC1=CC=CC=C1 VVVSZKHAZFQJHB-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 4
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
LMXVDOHKMVBODQ-UHFFFAOYSA-N 1-benzyl-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CC1=CC=CC=C1 LMXVDOHKMVBODQ-UHFFFAOYSA-N 0.000 description 3
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
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 description 3
PPBJJWDNJPGZPF-UHFFFAOYSA-N 2-(9-benzyl-5-carbamoyl-2-pentylcarbazol-4-yl)oxyacetic acid Chemical compound C=1C(CCCCC)=CC(OCC(O)=O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 PPBJJWDNJPGZPF-UHFFFAOYSA-N 0.000 description 3
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 description 3
PYNUQYVAXQHNAJ-UHFFFAOYSA-N 2-[(9-benzyl-5-carbamoyl-2-methoxy-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetic acid Chemical compound C12=CC(OC)=CC(OCC(O)=O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 PYNUQYVAXQHNAJ-UHFFFAOYSA-N 0.000 description 3
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 description 3
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 description 3
GCOWGWQVPARYNI-UHFFFAOYSA-N 2-[5-carbamoyl-9-[[3-(trifluoromethoxy)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(OC(F)(F)F)=C1 GCOWGWQVPARYNI-UHFFFAOYSA-N 0.000 description 3
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 description 3
XERTWWFWTYYSOP-UHFFFAOYSA-N 2-[9-benzyl-5-carbamoyl-2-(4-chlorophenyl)carbazol-4-yl]oxyacetic acid Chemical compound C12=CC(C=3C=CC(Cl)=CC=3)=CC(OCC(O)=O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 XERTWWFWTYYSOP-UHFFFAOYSA-N 0.000 description 3
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
229910000069 nitrogen hydride Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
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
235000011150 stannous chloride Nutrition 0.000 description 3
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
TUWSXUGAOWLTNQ-UHFFFAOYSA-N 5-hydroxy-9-[[3-(trifluoromethyl)phenyl]methyl]carbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(C(F)(F)F)=C1 TUWSXUGAOWLTNQ-UHFFFAOYSA-N 0.000 description 2
PEKKEWLYICTPBK-UHFFFAOYSA-N 5-hydroxy-9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC(O)=C2C2=C1C=CC=C2C(=O)N PEKKEWLYICTPBK-UHFFFAOYSA-N 0.000 description 2
SUCNZXOGTGJQOL-UHFFFAOYSA-N 9-[(2,6-dichlorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=C(Cl)C=CC=C1Cl SUCNZXOGTGJQOL-UHFFFAOYSA-N 0.000 description 2
HCWHUTCSDPMTFK-UHFFFAOYSA-N 9-[(2-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1Cl HCWHUTCSDPMTFK-UHFFFAOYSA-N 0.000 description 2
ATFZXISCTBMYTH-UHFFFAOYSA-N 9-[(2-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1C#N ATFZXISCTBMYTH-UHFFFAOYSA-N 0.000 description 2
XCPQDLGZHDLIOI-UHFFFAOYSA-N 9-[(3,5-dimethylphenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound CC1=CC(C)=CC(CN2C3=CC=CC(=C3C3=C(O)C=CC=C32)C(N)=O)=C1 XCPQDLGZHDLIOI-UHFFFAOYSA-N 0.000 description 2
MONOOOZJWVXGHQ-UHFFFAOYSA-N 9-[(3-chlorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(Cl)=C1 MONOOOZJWVXGHQ-UHFFFAOYSA-N 0.000 description 2
MXEREPIUEWGBPA-UHFFFAOYSA-N 9-[(3-cyanophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(C#N)=C1 MXEREPIUEWGBPA-UHFFFAOYSA-N 0.000 description 2
BUHJARZXNJGYSY-UHFFFAOYSA-N 9-[(3-fluorophenyl)methyl]-5-hydroxy-7-methylcarbazole-4-carboxamide Chemical compound C=1C(C)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC(F)=C1 BUHJARZXNJGYSY-UHFFFAOYSA-N 0.000 description 2
ALXSLILFYVMFEJ-UHFFFAOYSA-N 9-[(3-fluorophenyl)methyl]-5-hydroxycarbazole-4-carboxamide Chemical compound C12=CC=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC(F)=C1 ALXSLILFYVMFEJ-UHFFFAOYSA-N 0.000 description 2
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 description 2
IPUAVVIZGWPBKH-UHFFFAOYSA-N 9-benzyl-5-hydroxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound NC(=O)C1CCCC2=C1C1=C(O)C=CC=C1N2CC1=CC=CC=C1 IPUAVVIZGWPBKH-UHFFFAOYSA-N 0.000 description 2
JJVLMOAZPALOBR-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-[4-(trifluoromethyl)phenyl]carbazole-4-carboxamide Chemical compound C12=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(O)=C2C=2C(C(=O)N)=CC=CC=2N1CC1=CC=CC=C1 JJVLMOAZPALOBR-UHFFFAOYSA-N 0.000 description 2
WHMJBMNTVKVVOQ-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide Chemical compound C12=CC(OC)=CC(O)=C2C=2C(C(N)=O)CCCC=2N1CC1=CC=CC=C1 WHMJBMNTVKVVOQ-UHFFFAOYSA-N 0.000 description 2
XKGYMJJZCLTMRK-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-methylcarbazole-4-carboxamide Chemical compound C=1C(C)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 XKGYMJJZCLTMRK-UHFFFAOYSA-N 0.000 description 2
HXESYJXBJORHDW-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-pentylcarbazole-4-carboxamide Chemical compound C=1C(CCCCC)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 HXESYJXBJORHDW-UHFFFAOYSA-N 0.000 description 2
FMEIHIOTBPUOIJ-UHFFFAOYSA-N 9-benzyl-5-hydroxy-7-propan-2-ylcarbazole-4-carboxamide Chemical compound C=1C(C(C)C)=CC(O)=C(C2=C(C(N)=O)C=CC=C22)C=1N2CC1=CC=CC=C1 FMEIHIOTBPUOIJ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
229930045534 Me ester-Cyclohexaneundecanoic acid Natural products 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
238000010934 O-alkylation reaction Methods 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
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
229940050176 methyl chloride Drugs 0.000 description 2
VUJFIBWLMCQXKH-UHFFFAOYSA-N n-benzyl-2-chloro-5-methoxyaniline Chemical compound COC1=CC=C(Cl)C(NCC=2C=CC=CC=2)=C1 VUJFIBWLMCQXKH-UHFFFAOYSA-N 0.000 description 2
BUZLPADSVBADNN-UHFFFAOYSA-N n-benzyl-2-fluoro-5-methoxyaniline Chemical compound COC1=CC=C(F)C(NCC=2C=CC=CC=2)=C1 BUZLPADSVBADNN-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
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 2
229910000105 potassium hydride Inorganic materials 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000004366 reverse phase liquid chromatography Methods 0.000 description 2
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230000010933 acylation Effects 0.000 description 1
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229910052786 argon Inorganic materials 0.000 description 1
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230000002917 arthritic effect Effects 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
YCNIBOIOWCTRCL-UHFFFAOYSA-N azane;2,2,2-trifluoroacetic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)F YCNIBOIOWCTRCL-UHFFFAOYSA-N 0.000 description 1
XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000010367 cloning Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004802 cyanophenyl group Chemical group 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
MWPIIMNHWGOFBL-UHFFFAOYSA-N dichloromethane;toluene Chemical compound ClCCl.CC1=CC=CC=C1 MWPIIMNHWGOFBL-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
UDRZOTKSRMNJBZ-UHFFFAOYSA-N ethyl 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1C1=C(OC)C=CC(C)=C1N2CC1=CC=CC=C1 UDRZOTKSRMNJBZ-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
239000011888 foil Substances 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
URPRVBIULYUOOY-UHFFFAOYSA-N lithium;phenylmethoxymethylbenzene Chemical compound [Li].C=1C=CC=CC=1COCC1=CC=CC=C1 URPRVBIULYUOOY-UHFFFAOYSA-N 0.000 description 1
239000012528 membrane Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
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 1
SDXJUKFDGCMOHO-UHFFFAOYSA-N methyl 2-(9-benzyl-5-carbamoyl-2-methoxycarbazol-4-yl)oxyacetate Chemical compound C12=CC=CC(C(N)=O)=C2C=2C(OCC(=O)OC)=CC(OC)=CC=2N1CC1=CC=CC=C1 SDXJUKFDGCMOHO-UHFFFAOYSA-N 0.000 description 1
YSCQNQWTIHYXKX-UHFFFAOYSA-N methyl 2-[(5-carbamoyl-1-chloro-9h-carbazol-4-yl)oxy]acetate Chemical compound N1C2=CC=CC(C(N)=O)=C2C2=C1C(Cl)=CC=C2OCC(=O)OC YSCQNQWTIHYXKX-UHFFFAOYSA-N 0.000 description 1
ANUWEGZYNYTFIU-UHFFFAOYSA-N methyl 2-[(9-benzyl-5-carbamoyl-1-fluoro-5,6,7,8-tetrahydrocarbazol-4-yl)oxy]acetate Chemical compound C1=2CCCC(C(N)=O)C=2C=2C(OCC(=O)OC)=CC=C(F)C=2N1CC1=CC=CC=C1 ANUWEGZYNYTFIU-UHFFFAOYSA-N 0.000 description 1
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
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 1
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

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Neurology (AREA)
Orthopedic Medicine & Surgery (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Diabetes (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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19991821A 1998-04-17 1999-04-16 Substituerte tricykliske forbindelser NO314400B1 (no)

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Application Number	Priority Date	Filing Date	Title
US6232898A	1998-04-17	1998-04-17

Publications (3)

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NO991821D0 NO991821D0 (no)	1999-04-16
NO991821L NO991821L (no)	1999-10-18
NO314400B1 true NO314400B1 (no)	2003-03-17

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NO19991822A NO312240B1 (no)	1998-04-17	1999-04-16	Substituerte tricykliske forbindelser, preparater inneholdende forbindelsene samt forbindelsenes anvendelse

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EP (2)	EP0950657B1 (fr)
JP (2)	JP4435330B2 (fr)
KR (2)	KR19990083232A (fr)
CN (1)	CN1149193C (fr)
AR (2)	AR018593A1 (fr)
AT (2)	ATE268756T1 (fr)
AU (2)	AU753547B2 (fr)
BR (2)	BR9901279A (fr)
CA (2)	CA2269246C (fr)
CO (2)	CO5031247A1 (fr)
CZ (2)	CZ136999A3 (fr)
DE (2)	DE69917833T2 (fr)
DK (1)	DK0950657T3 (fr)
DZ (1)	DZ2769A1 (fr)
EA (2)	EA002347B1 (fr)
ES (2)	ES2226286T3 (fr)
HU (2)	HUP9901220A3 (fr)
ID (2)	ID23287A (fr)
IL (2)	IL129485A0 (fr)
NO (2)	NO314400B1 (fr)
NZ (3)	NZ335251A (fr)
PE (2)	PE20000476A1 (fr)
PL (2)	PL332566A1 (fr)
PT (1)	PT950657E (fr)
SG (2)	SG81976A1 (fr)
SI (1)	SI0950657T1 (fr)
TR (2)	TR199900853A2 (fr)
TW (1)	TWI238160B (fr)
YU (2)	YU19199A (fr)
ZA (2)	ZA992772B (fr)

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JP2001513555A (ja) *	1997-08-28	2001-09-04	イーライ・リリー・アンド・カンパニー	非リウマチ様関節炎の処置方法
DZ2769A1 (fr) *	1998-04-17	2003-12-01	Lilly Co Eli	Composés tricycliques substitués.
CA2358492A1 (fr) *	1998-12-21	2000-06-29	Eli Lilly And Company	Polytherapie destinee au traitement de la septicemie
US6706752B1 (en)	1999-07-19	2004-03-16	Eli Lilly And Company	sPLA2 inhibitors
JP2003505372A (ja) *	1999-07-19	2003-02-12	イーライ・リリー・アンド・カンパニー	ｓＰＬＡ２インヒビター
WO2002000255A1 (fr) *	2000-06-29	2002-01-03	Shionogi & Co., Ltd.	Remedes contre le cancer
WO2002000257A1 (fr) *	2000-06-29	2002-01-03	Shionogi & Co., Ltd.	Remedes a la maladie d'alzheimer
WO2002000256A1 (fr) *	2000-06-29	2002-01-03	Shionogi & Co., Ltd.	Remedes contre la cirrhose
EP1303262A2 (fr) *	2000-07-14	2003-04-23	Eli Lilly And Company	Utilisation d'un inhibiteur de de la spla2 pour le traitement de la septicite
EP1345898A2 (fr)	2000-12-18	2003-09-24	Eli Lilly And Company	Derives tetracycliques de carbazole et leur utilisation comme inhibiteurs de splaz
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 (fr) *	2007-04-27	2008-11-05	AEterna Zentaris GmbH	Nouveaux dérivés de tétrahydrocarbazole en tant que ligands de récepteurs couplés à la protéine G
CA2719721C (fr)	2008-03-26	2012-12-18	Daiichi Sankyo Company, Limited	Derive de tetrahydroisoquinoline
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1999
- 1999-04-14 DZ DZ990069A patent/DZ2769A1/fr active
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- 1999-04-16 HU HU9901220A patent/HUP9901220A3/hu unknown
- 1999-04-16 BR BR9901279-0A patent/BR9901279A/pt not_active IP Right Cessation
- 1999-04-16 KR KR1019990013436A patent/KR19990083232A/ko not_active Withdrawn
- 1999-04-16 TR TR1999/00853A patent/TR199900853A2/xx unknown
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- 1999-04-16 AT AT99302941T patent/ATE268756T1/de not_active IP Right Cessation
- 1999-04-16 PT PT99302967T patent/PT950657E/pt unknown
- 1999-04-16 PE PE1999000320A patent/PE20000476A1/es not_active Application Discontinuation
- 1999-04-16 PE PE1999000314A patent/PE20000432A1/es not_active Application Discontinuation
- 1999-04-16 PL PL99332566A patent/PL332566A1/xx not_active Application Discontinuation
- 1999-04-16 CO CO99022884A patent/CO5031247A1/es unknown
- 1999-04-16 JP JP15240099A patent/JP4435330B2/ja not_active Expired - Fee Related
- 1999-04-16 AU AU23819/99A patent/AU753547B2/en not_active Ceased
- 1999-04-16 EP EP99302967A patent/EP0950657B1/fr not_active Expired - Lifetime
- 1999-04-16 NO NO19991821A patent/NO314400B1/no not_active IP Right Cessation
- 1999-04-16 CZ CZ991369A patent/CZ136999A3/cs unknown
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- 1999-04-16 AR ARP990101771A patent/AR018593A1/es active IP Right Grant
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- 1999-04-16 CA CA002269246A patent/CA2269246C/fr not_active Expired - Fee Related
- 1999-04-16 EP EP99302941A patent/EP0952149B1/fr not_active Expired - Lifetime
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- 1999-04-16 JP JP11109629A patent/JPH11322713A/ja not_active Withdrawn
- 1999-04-16 CA CA002269262A patent/CA2269262A1/fr not_active Abandoned
- 1999-04-16 AU AU23817/99A patent/AU753436B2/en not_active Ceased
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Also Published As

Publication number	Publication date
AU2381999A (en)	1999-10-28
NO312240B1 (no)	2002-04-15
EA199900301A2 (ru)	1999-10-28
AR018593A1 (es)	2001-11-28
YU19199A (sh)	2002-08-12
ATE268756T1 (de)	2004-06-15
HU9901220D0 (en)	1999-06-28
ID23761A (id)	2000-05-11
CZ136999A3 (cs)	1999-11-17
KR19990083232A (ko)	1999-11-25
PE20000432A1 (es)	2000-05-23
NO991822D0 (no)	1999-04-16
CO5011054A1 (es)	2001-02-28
DK0950657T3 (da)	2004-11-22
JPH11322713A (ja)	1999-11-24
DZ2769A1 (fr)	2003-12-01
NO991821L (no)	1999-10-18
TWI238160B (en)	2005-08-21
ES2226286T3 (es)	2005-03-16
CA2269246C (fr)	2009-08-25
EP0950657B1 (fr)	2004-07-14
ATE271037T1 (de)	2004-07-15
AU2381799A (en)	1999-10-28
ID23287A (id)	2000-04-05
CZ137099A3 (cs)	1999-11-17
BR9901279A (pt)	2000-05-02
ZA992772B (en)	2002-07-16
EA199900303A3 (ru)	2000-04-24
JP2000026416A (ja)	2000-01-25
BR9902365A (pt)	2001-04-24
KR19990083233A (ko)	1999-11-25
IL129485A0 (en)	2000-02-29
PL332565A1 (en)	1999-10-25
SI0950657T1 (en)	2005-02-28
EP0950657A3 (fr)	2001-08-16
ES2222663T3 (es)	2005-02-01
DE69918590D1 (de)	2004-08-19
YU18999A (sh)	2002-08-12
PE20000476A1 (es)	2000-06-02
HU9901221A (hu)	2000-04-28
TR199900853A3 (tr)	1999-11-22
EP0952149A2 (fr)	1999-10-27
CN1253948A (zh)	2000-05-24
EA002816B1 (ru)	2002-10-31
PT950657E (pt)	2004-11-30
DE69917833D1 (de)	2004-07-15
AU753436B2 (en)	2002-10-17
CN1149193C (zh)	2004-05-12
NZ335251A (en)	2000-11-24
EA199900301A3 (ru)	2000-04-24
JP4435330B2 (ja)	2010-03-17
EA199900303A2 (ru)	1999-10-28
CO5031247A1 (es)	2001-04-27
HUP9901220A3 (en)	2001-11-28
HU9901220A (hu)	2000-04-28
EP0952149A3 (fr)	2001-08-16
DE69917833T2 (de)	2005-07-14
EA002347B1 (ru)	2002-04-25
EP0952149B1 (fr)	2004-06-09
HUP9901221A3 (en)	2001-11-28
TR199900853A2 (xx)	1999-11-22
SG81977A1 (en)	2001-07-24
DE69918590T2 (de)	2005-07-21
NZ507564A (en)	2002-10-25
IL129483A0 (en)	2000-02-29
ZA992771B (en)	2002-04-18
HU9901221D0 (en)	1999-06-28
AU753547B2 (en)	2002-10-24
PL332566A1 (en)	1999-10-25
CA2269246A1 (fr)	1999-10-17
NO991822L (no)	1999-10-18
SG81976A1 (en)	2001-07-24
EP0950657A2 (fr)	1999-10-20
KR100586761B1 (ko)	2006-06-08
AR018186A1 (es)	2001-10-31
NO991821D0 (no)	1999-04-16
CA2269262A1 (fr)	1999-10-17
NZ335253A (en)	2000-11-24
TR199900843A2 (xx)	2000-02-21

Legal Events

Date	Code	Title	Description
2004-12-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO314400B1 (no)	2003-03-17	Substituerte tricykliske forbindelser
EP0772592B1 (fr)	2003-05-02	INHIBITEURS DE PLAs 2 A FONCTIONNALITE 1H-INDOLE EN POSITION 1
AU2009247262B2 (en)	2013-01-31	Amide compound
US6177440B1 (en)	2001-01-23	Substituted tricyclics
US8884016B2 (en)	2014-11-11	Apixaban preparation process
US5684034A (en)	1997-11-04	1H-indole-3-acetamide sPLA2 inhibitors
JP3241381B2 (ja)	2001-12-25	三環性キノキサリンジオン化合物
NO314899B1 (no)	2003-06-10	Substituerte tricykliske forbindelser samt preparater inneholdende forbindelsene
NO177139B (no)	1995-04-18	Analogifremgangsmåte for fremstilling av terapeutisk aktive 3-amidoindolylderivater
JP2001503055A5 (fr)	2009-09-17
EP0950661B1 (fr)	2003-11-12	Composés tricycliques substitués pour le traitement des maladies induites par sPLA2
US20050026988A1 (en)	2005-02-03	Cyclopenta'b! indole derivatives as spla inhibitors
US6713645B1 (en)	2004-03-30	Substituted tricyclics
DE60208065T2 (de)	2006-07-13	Cyclohept'b! indolderivate als spla2-inhibitoren
JP3162572B2 (ja)	2001-05-08	インドロイルグアニジン誘導体
EP1395554B1 (fr)	2007-02-14	Carbazoles substitues comme inhibiteurs de spla2
JP2004518659A5 (fr)	2005-12-22
WO2001014384A1 (fr)	2001-03-01	Derives dihydrobenzofuran tricycliques, leur procede de preparation et agents
NO175680B (no)	1994-08-08	Fremgangsmåte for fremstilling av en 3-alkylert indol
HK1024912A (en)	2000-10-27	Substituted carbazoles, process for their preparation and their use as spla2 inhibitors
HK1024911A (en)	2000-10-27	Substituted carbazoles, process for their preparation and their use as spla2 inhibitors
MXPA99003587A (es)	2000-07-01	Compuestos triciclicos substituidos