HRP20110773T1 - Derivati 2,3,4,9-tetrahidro-1h-karbazola kao antagonisti crth2 receptora - Google Patents
Derivati 2,3,4,9-tetrahidro-1h-karbazola kao antagonisti crth2 receptora Download PDFInfo
- Publication number
- HRP20110773T1 HRP20110773T1 HR20110773T HRP20110773T HRP20110773T1 HR P20110773 T1 HRP20110773 T1 HR P20110773T1 HR 20110773 T HR20110773 T HR 20110773T HR P20110773 T HRP20110773 T HR P20110773T HR P20110773 T1 HRP20110773 T1 HR P20110773T1
- Authority
- HR
- Croatia
- Prior art keywords
- tetrahydro
- carbazol
- acetic acid
- phenyl
- carbamoyl
- Prior art date
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- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title claims abstract 3
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- -1 di-substituted phenyl ring Chemical group 0.000 claims abstract 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract 22
- 150000002367 halogens Chemical class 0.000 claims abstract 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 150000003839 salts Chemical class 0.000 claims abstract 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 125000003118 aryl group Chemical group 0.000 claims abstract 12
- 239000000203 mixture Substances 0.000 claims abstract 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 9
- 125000001424 substituent group Chemical group 0.000 claims abstract 9
- 125000004122 cyclic group Chemical group 0.000 claims abstract 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims abstract 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 3
- 125000005110 aryl thio group Chemical group 0.000 claims abstract 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 239000001301 oxygen Chemical group 0.000 claims abstract 3
- 239000011593 sulfur Chemical group 0.000 claims abstract 3
- 229910052717 sulfur Chemical group 0.000 claims abstract 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 230000000877 morphologic effect Effects 0.000 claims abstract 2
- 125000003367 polycyclic group Chemical group 0.000 claims abstract 2
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- XZYGGTLGXGSLPT-UHFFFAOYSA-N 2-[3-(azocane-1-carbonyl)-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC(F)=CC=C3N(CC(=O)O)C=2CCC1C(=O)N1CCCCCCC1 XZYGGTLGXGSLPT-UHFFFAOYSA-N 0.000 claims 2
- QQZISNGDLSONNX-UHFFFAOYSA-N 2-[3-[benzhydryl(methyl)carbamoyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(F)C=C22)CC(O)=O)=C2CC1C(=O)N(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 QQZISNGDLSONNX-UHFFFAOYSA-N 0.000 claims 2
- FHHSYNMECGZZSU-UHFFFAOYSA-N 2-[3-[benzyl(2-phenylethyl)carbamoyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC(F)=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=CC=CC=1)CCC1=CC=CC=C1 FHHSYNMECGZZSU-UHFFFAOYSA-N 0.000 claims 2
- IPZLIVBDUQBIHY-UHFFFAOYSA-N 2-[3-[benzyl(propan-2-yl)carbamoyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(F)C=C22)CC(O)=O)=C2CC1C(=O)N(C(C)C)CC1=CC=CC=C1 IPZLIVBDUQBIHY-UHFFFAOYSA-N 0.000 claims 2
- DPIHYVCVIWWCKW-PPUHSXQSSA-N 2-[3-[benzyl-[(1r)-1-phenylethyl]carbamoyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(F)C=C22)CC(O)=O)=C2CC1C(=O)N([C@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 DPIHYVCVIWWCKW-PPUHSXQSSA-N 0.000 claims 2
- DPIHYVCVIWWCKW-AJZOCDQUSA-N 2-[3-[benzyl-[(1s)-1-phenylethyl]carbamoyl]-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(F)C=C22)CC(O)=O)=C2CC1C(=O)N([C@@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 DPIHYVCVIWWCKW-AJZOCDQUSA-N 0.000 claims 2
- ACUGWZFIPQASQS-UHFFFAOYSA-N 2-[6-fluoro-3-[4-(4-fluorophenyl)piperazine-1-carbonyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC(F)=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 ACUGWZFIPQASQS-UHFFFAOYSA-N 0.000 claims 2
- DNSIYOXARUHZSL-IURRXHLWSA-N 2-[6-fluoro-3-[[(1r)-1-phenylethyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1([C@H](NC(=O)C2CC3=C(N(C4=CC=C(F)C=C43)CC(O)=O)CC2)C)=CC=CC=C1 DNSIYOXARUHZSL-IURRXHLWSA-N 0.000 claims 2
- AIHSLEKYDKNXQO-UHFFFAOYSA-N 2-[6-fluoro-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(F)C=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 AIHSLEKYDKNXQO-UHFFFAOYSA-N 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 claims 1
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004562 2,3-dihydroindol-1-yl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 1
- GOGIWYONEIGXAK-UHFFFAOYSA-N 2-(3-phenylmethoxycarbonyl-1,2,3,4-tetrahydrocarbazol-9-yl)acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)OCC1=CC=CC=C1 GOGIWYONEIGXAK-UHFFFAOYSA-N 0.000 claims 1
- KXBJQRMEBPETNH-CQSZACIVSA-N 2-[(3r)-3-[(4-chlorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound O=C([C@H]1CC2=C(N(C3=CC=CC=C32)CC(O)=O)CC1)N(C)C1=CC=C(Cl)C=C1 KXBJQRMEBPETNH-CQSZACIVSA-N 0.000 claims 1
- KXBJQRMEBPETNH-AWEZNQCLSA-N 2-[(3s)-3-[(4-chlorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound O=C([C@@H]1CC2=C(N(C3=CC=CC=C32)CC(O)=O)CC1)N(C)C1=CC=C(Cl)C=C1 KXBJQRMEBPETNH-AWEZNQCLSA-N 0.000 claims 1
- GYTZHWTWXJNXPX-UHFFFAOYSA-N 2-[3-(1,3-benzodioxol-5-ylmethylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1=C2OCOC2=CC(CNC(=O)C2CCC=3N(C4=CC=CC=C4C=3C2)CC(=O)O)=C1 GYTZHWTWXJNXPX-UHFFFAOYSA-N 0.000 claims 1
- STFCNMAIGLQTIJ-UHFFFAOYSA-N 2-[3-(1,3-dihydrobenzo[de]isoquinoline-2-carbonyl)-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1=CC(CN(C(=O)C2(CC3=C(N(C4=CC=CC=C43)CC(O)=O)CC2)C)C2)=C3C2=CC=CC3=C1 STFCNMAIGLQTIJ-UHFFFAOYSA-N 0.000 claims 1
- PKAWUOFRJSQCEK-UHFFFAOYSA-N 2-[3-(11,12-dihydro-6h-benzo[c][1]benzazocine-5-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C2=CC=CC=C2CCC2=CC=CC=C2N1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 PKAWUOFRJSQCEK-UHFFFAOYSA-N 0.000 claims 1
- HVMHKCAKHREXMW-UHFFFAOYSA-N 2-[3-(2,2-diphenylethylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 HVMHKCAKHREXMW-UHFFFAOYSA-N 0.000 claims 1
- JUXNJEFWMLKAHQ-UHFFFAOYSA-N 2-[3-(2,3-dihydroindole-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2N1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 JUXNJEFWMLKAHQ-UHFFFAOYSA-N 0.000 claims 1
- QQHYFPRRARQRBI-UHFFFAOYSA-N 2-[3-(2,3-dihydroindole-1-carbonyl)-3-ethyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2N1C(=O)C1(CC)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 QQHYFPRRARQRBI-UHFFFAOYSA-N 0.000 claims 1
- PYAAXRUWUZECJX-UHFFFAOYSA-N 2-[3-(2,3-dihydroindole-1-carbonyl)-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2N1C(=O)C1(C)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 PYAAXRUWUZECJX-UHFFFAOYSA-N 0.000 claims 1
- XKXDDWZLTQCWJY-UHFFFAOYSA-N 2-[3-(2,3-dihydroindole-1-carbonyl)-3-propyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2N1C(=O)C1(CCC)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 XKXDDWZLTQCWJY-UHFFFAOYSA-N 0.000 claims 1
- WYCYCYPKQBMHLY-UHFFFAOYSA-N 2-[3-(2,3-dihydroindole-1-carbonyl)-6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2N1C(=O)C1CCC(N(C2=CC=C(F)C=C22)CC(=O)O)=C2C1 WYCYCYPKQBMHLY-UHFFFAOYSA-N 0.000 claims 1
- RUHIBBIMWZOREF-UHFFFAOYSA-N 2-[3-(3,4-dihydro-1h-isoquinoline-2-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2CN1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 RUHIBBIMWZOREF-UHFFFAOYSA-N 0.000 claims 1
- WPHHWFGRQREMNM-UHFFFAOYSA-N 2-[3-(3,4-dihydro-2h-quinoline-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CCC2=CC=CC=C2N1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 WPHHWFGRQREMNM-UHFFFAOYSA-N 0.000 claims 1
- BITMNVNPGYAATO-UHFFFAOYSA-N 2-[3-(3,4-dihydro-2h-quinoline-1-carbonyl)-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CCC2=CC=CC=C2N1C(=O)C1(C)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 BITMNVNPGYAATO-UHFFFAOYSA-N 0.000 claims 1
- SIRFPRQAILCXJR-UHFFFAOYSA-N 2-[3-(4-benzhydrylpiperazine-1-carbonyl)-8-chloro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC(Cl)=C3N(CC(=O)O)C=2CCC1C(=O)N(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 SIRFPRQAILCXJR-UHFFFAOYSA-N 0.000 claims 1
- IHLMGHQSFSXEPC-UHFFFAOYSA-N 2-[3-(6,11-dihydrobenzo[c][1]benzazepine-5-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C2=CC=CC=C2CC2=CC=CC=C2N1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 IHLMGHQSFSXEPC-UHFFFAOYSA-N 0.000 claims 1
- WSSIXFCPQDRJRS-UHFFFAOYSA-N 2-[3-(6,11-dihydrobenzo[c][1]benzazepine-5-carbonyl)-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1C2=CC=CC=C2CC2=CC=CC=C2N1C(=O)C1(C)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 WSSIXFCPQDRJRS-UHFFFAOYSA-N 0.000 claims 1
- PDNHAARPTHVLNH-UHFFFAOYSA-N 2-[3-(6,7-dimethoxy-3,4-dihydro-1h-isoquinoline-2-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(CC2)=C1CC2C(=O)N1CCC(C=C(C(=C2)OC)OC)=C2C1 PDNHAARPTHVLNH-UHFFFAOYSA-N 0.000 claims 1
- HYQPMPRHLQLIHP-UHFFFAOYSA-N 2-[3-(benzhydrylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 HYQPMPRHLQLIHP-UHFFFAOYSA-N 0.000 claims 1
- OHDWVPABSYGHCR-UHFFFAOYSA-N 2-[3-(benzhydrylcarbamoyl)-3-ethyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CC)C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 OHDWVPABSYGHCR-UHFFFAOYSA-N 0.000 claims 1
- GVZVAXFRDKINFO-UHFFFAOYSA-N 2-[3-(benzhydrylcarbamoyl)-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 GVZVAXFRDKINFO-UHFFFAOYSA-N 0.000 claims 1
- FPGYNTJNQGZXND-UHFFFAOYSA-N 2-[3-(benzhydrylcarbamoyl)-3-propyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CCC)C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 FPGYNTJNQGZXND-UHFFFAOYSA-N 0.000 claims 1
- JIHRDVPBEWCPEH-UHFFFAOYSA-N 2-[3-(benzhydrylcarbamoyl)-8-chloro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC(Cl)=C3N(CC(=O)O)C=2CCC1C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 JIHRDVPBEWCPEH-UHFFFAOYSA-N 0.000 claims 1
- YTNSYBDHNSVAAD-UHFFFAOYSA-N 2-[3-(benzo[b][1]benzazepine-11-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C12=CC=CC=C2C=CC2=CC=CC=C2N1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 YTNSYBDHNSVAAD-UHFFFAOYSA-N 0.000 claims 1
- VDLNPKBMAJGTEF-UHFFFAOYSA-N 2-[3-(dibenzylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 VDLNPKBMAJGTEF-UHFFFAOYSA-N 0.000 claims 1
- HUXWTTSNVWINFN-UHFFFAOYSA-N 2-[3-(phenylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NC1=CC=CC=C1 HUXWTTSNVWINFN-UHFFFAOYSA-N 0.000 claims 1
- CARDSDAEBPDWAB-UHFFFAOYSA-N 2-[3-(phenylcarbamoyl)-3-propyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CCC)C(=O)NC1=CC=CC=C1 CARDSDAEBPDWAB-UHFFFAOYSA-N 0.000 claims 1
- COFXVISULUXJAI-LDCVWXEPSA-N 2-[3-[(1r)-1-phenylethoxy]carbonyl-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1([C@H](OC(=O)C2CC3=C(N(C4=CC=CC=C43)CC(O)=O)CC2)C)=CC=CC=C1 COFXVISULUXJAI-LDCVWXEPSA-N 0.000 claims 1
- QDPMRJNSNRIUNH-UHFFFAOYSA-N 2-[3-[(2,3-dichlorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=CC(Cl)=C1Cl QDPMRJNSNRIUNH-UHFFFAOYSA-N 0.000 claims 1
- AGTHPTHBIDVRLK-UHFFFAOYSA-N 2-[3-[(2,4-dichlorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=C(Cl)C=C1Cl AGTHPTHBIDVRLK-UHFFFAOYSA-N 0.000 claims 1
- VWFIUSJOPJZNDK-UHFFFAOYSA-N 2-[3-[(2,4-difluorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=C(F)C=C1F VWFIUSJOPJZNDK-UHFFFAOYSA-N 0.000 claims 1
- VZNHTFNQHSSJND-UHFFFAOYSA-N 2-[3-[(2,6-difluorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=C(F)C=CC=C1F VZNHTFNQHSSJND-UHFFFAOYSA-N 0.000 claims 1
- QTNXBZXJKXWOMG-UHFFFAOYSA-N 2-[3-[(2-benzylphenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NC1=CC=CC=C1CC1=CC=CC=C1 QTNXBZXJKXWOMG-UHFFFAOYSA-N 0.000 claims 1
- AXBMCSOPUFKDJM-UHFFFAOYSA-N 2-[3-[(2-benzylphenyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NC1=CC=CC=C1CC1=CC=CC=C1 AXBMCSOPUFKDJM-UHFFFAOYSA-N 0.000 claims 1
- PVBZSBJQPDGTQR-UHFFFAOYSA-N 2-[3-[(2-chlorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=CC=C1Cl PVBZSBJQPDGTQR-UHFFFAOYSA-N 0.000 claims 1
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- FFBXTPAMCZZDPZ-UHFFFAOYSA-N 2-[3-[(2-fluorophenyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NC1=CC=CC=C1F FFBXTPAMCZZDPZ-UHFFFAOYSA-N 0.000 claims 1
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- WUJIQHDUCHOUFN-UHFFFAOYSA-N 2-[3-[(2-fluorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=CC=C1F WUJIQHDUCHOUFN-UHFFFAOYSA-N 0.000 claims 1
- MDFZUBLSNMNYMF-UHFFFAOYSA-N 2-[3-[(2-methoxy-5-phenylphenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1=C(NC(=O)C2CC3=C(N(C4=CC=CC=C43)CC(O)=O)CC2)C(OC)=CC=C1C1=CC=CC=C1 MDFZUBLSNMNYMF-UHFFFAOYSA-N 0.000 claims 1
- OSABOECUSSXKOT-UHFFFAOYSA-N 2-[3-[(2-methoxyphenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound COC1=CC=CC=C1NC(=O)C1CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 OSABOECUSSXKOT-UHFFFAOYSA-N 0.000 claims 1
- NXVVUTVSKUPCPN-UHFFFAOYSA-N 2-[3-[(3,4-dichlorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 NXVVUTVSKUPCPN-UHFFFAOYSA-N 0.000 claims 1
- UOIOTWFGVSZQLS-UHFFFAOYSA-N 2-[3-[(3,4-dichlorophenyl)-methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 UOIOTWFGVSZQLS-UHFFFAOYSA-N 0.000 claims 1
- IHPZWSKXDNJAHB-UHFFFAOYSA-N 2-[3-[(3,4-dichlorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=C(Cl)C(Cl)=C1 IHPZWSKXDNJAHB-UHFFFAOYSA-N 0.000 claims 1
- YNQJJDIPRIQBQJ-UHFFFAOYSA-N 2-[3-[(3,5-difluorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC(F)=CC(F)=C1 YNQJJDIPRIQBQJ-UHFFFAOYSA-N 0.000 claims 1
- HVXNSYQVISAZCL-UHFFFAOYSA-N 2-[3-[(3-benzoylphenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NC(C=1)=CC=CC=1C(=O)C1=CC=CC=C1 HVXNSYQVISAZCL-UHFFFAOYSA-N 0.000 claims 1
- GWEDRWCBBAVJCW-UHFFFAOYSA-N 2-[3-[(3-chlorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC(Cl)=C1 GWEDRWCBBAVJCW-UHFFFAOYSA-N 0.000 claims 1
- CJNTWYOIOVTHEW-UHFFFAOYSA-N 2-[3-[(3-chlorophenyl)-methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)C1=CC=CC(Cl)=C1 CJNTWYOIOVTHEW-UHFFFAOYSA-N 0.000 claims 1
- IESADJAKBYABRN-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC(F)=C1 IESADJAKBYABRN-UHFFFAOYSA-N 0.000 claims 1
- YVDKZMNCPLXUGN-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NC1=CC=CC(F)=C1 YVDKZMNCPLXUGN-UHFFFAOYSA-N 0.000 claims 1
- MAFYELFFPSMWLJ-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NC1=CC=CC(F)=C1 MAFYELFFPSMWLJ-UHFFFAOYSA-N 0.000 claims 1
- AFTBBFIEVKZIFC-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)carbamoyl]-3-propyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CCC)C(=O)NC1=CC=CC(F)=C1 AFTBBFIEVKZIFC-UHFFFAOYSA-N 0.000 claims 1
- KXBJQRMEBPETNH-UHFFFAOYSA-N 2-[3-[(4-chlorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=C(Cl)C=C1 KXBJQRMEBPETNH-UHFFFAOYSA-N 0.000 claims 1
- DKAMUVRSSDHCSL-UHFFFAOYSA-N 2-[3-[(4-chlorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=C(Cl)C=C1 DKAMUVRSSDHCSL-UHFFFAOYSA-N 0.000 claims 1
- JGGYIPMGTJFGLJ-UHFFFAOYSA-N 2-[3-[(4-fluorophenyl)-methylcarbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=C(F)C=C1 JGGYIPMGTJFGLJ-UHFFFAOYSA-N 0.000 claims 1
- ONDNQTKSMOXAAR-UHFFFAOYSA-N 2-[3-[(4-fluorophenyl)-methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)C1=CC=C(F)C=C1 ONDNQTKSMOXAAR-UHFFFAOYSA-N 0.000 claims 1
- DDORZGMPJCNVDD-UHFFFAOYSA-N 2-[3-[(4-fluorophenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)NC1=CC=C(F)C=C1 DDORZGMPJCNVDD-UHFFFAOYSA-N 0.000 claims 1
- RAGXPCYZHVEMCE-UHFFFAOYSA-N 2-[3-[(4-fluorophenyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NC1=CC=C(F)C=C1 RAGXPCYZHVEMCE-UHFFFAOYSA-N 0.000 claims 1
- NMDHRJVZTROJFP-UHFFFAOYSA-N 2-[3-[(4-fluorophenyl)carbamoyl]-3-propyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CCC)C(=O)NC1=CC=C(F)C=C1 NMDHRJVZTROJFP-UHFFFAOYSA-N 0.000 claims 1
- AUVSHYOYNGLCGO-UHFFFAOYSA-N 2-[3-[(4-fluorophenyl)methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=C(F)C=C1 AUVSHYOYNGLCGO-UHFFFAOYSA-N 0.000 claims 1
- CPYRTFFKVCPLSN-UHFFFAOYSA-N 2-[3-[(5-chloro-2-methoxyphenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 CPYRTFFKVCPLSN-UHFFFAOYSA-N 0.000 claims 1
- IOAUEEHBILFCEK-UHFFFAOYSA-N 2-[3-[4-(4-fluorophenyl)piperazine-1-carbonyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 IOAUEEHBILFCEK-UHFFFAOYSA-N 0.000 claims 1
- IVFBXEXOEHUGMB-UHFFFAOYSA-N 2-[3-[7-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carbonyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CCC2=CC=C(C(F)(F)F)C=C2N1C(=O)C1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 IVFBXEXOEHUGMB-UHFFFAOYSA-N 0.000 claims 1
- BWGRZNUQJMZYFG-UHFFFAOYSA-N 2-[3-[[2-(difluoromethoxy)phenyl]methylcarbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NCC1=CC=CC=C1OC(F)F BWGRZNUQJMZYFG-UHFFFAOYSA-N 0.000 claims 1
- GYEDYJYRKNQWLN-UHFFFAOYSA-N 2-[3-[benzhydryl(methyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 GYEDYJYRKNQWLN-UHFFFAOYSA-N 0.000 claims 1
- UQNGUWDNUFPGHX-UHFFFAOYSA-N 2-[3-[benzhydryl(methyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 UQNGUWDNUFPGHX-UHFFFAOYSA-N 0.000 claims 1
- KPVNMVREBKMCEX-UHFFFAOYSA-N 2-[3-[benzhydryl(methyl)carbamoyl]-8-chloro-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=C(Cl)C=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 KPVNMVREBKMCEX-UHFFFAOYSA-N 0.000 claims 1
- RFQMDFHKAMFLHV-UHFFFAOYSA-N 2-[3-[benzyl(2-cyanoethyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CCC#N)CC1=CC=CC=C1 RFQMDFHKAMFLHV-UHFFFAOYSA-N 0.000 claims 1
- AZJHZIWHGVUSQO-UHFFFAOYSA-N 2-[3-[benzyl(2-cyanoethyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CCC#N)CC1=CC=CC=C1 AZJHZIWHGVUSQO-UHFFFAOYSA-N 0.000 claims 1
- HFNKRXVXKBEMNJ-UHFFFAOYSA-N 2-[3-[benzyl(2-phenylethyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=CC=CC=1)CCC1=CC=CC=C1 HFNKRXVXKBEMNJ-UHFFFAOYSA-N 0.000 claims 1
- NGEBOAKDJIILFU-UHFFFAOYSA-N 2-[3-[benzyl(2-phenylethyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C=CC=CC=1)CCC1=CC=CC=C1 NGEBOAKDJIILFU-UHFFFAOYSA-N 0.000 claims 1
- HLBGNNKEZMIUGX-UHFFFAOYSA-N 2-[3-[benzyl(butyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CCCC)CC1=CC=CC=C1 HLBGNNKEZMIUGX-UHFFFAOYSA-N 0.000 claims 1
- XNRWKCSETYTWRJ-UHFFFAOYSA-N 2-[3-[benzyl(cyanomethyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC#N)CC1=CC=CC=C1 XNRWKCSETYTWRJ-UHFFFAOYSA-N 0.000 claims 1
- DWXDTXDLYQHLSC-UHFFFAOYSA-N 2-[3-[benzyl(ethyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC)CC1=CC=CC=C1 DWXDTXDLYQHLSC-UHFFFAOYSA-N 0.000 claims 1
- CZCFDCPETMZXPH-UHFFFAOYSA-N 2-[3-[benzyl(methyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)CC1=CC=CC=C1 CZCFDCPETMZXPH-UHFFFAOYSA-N 0.000 claims 1
- YALGDFRAFYGRAM-UHFFFAOYSA-N 2-[3-[benzyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 YALGDFRAFYGRAM-UHFFFAOYSA-N 0.000 claims 1
- KGMROJZPPANDNJ-UHFFFAOYSA-N 2-[3-[benzyl(phenyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 KGMROJZPPANDNJ-UHFFFAOYSA-N 0.000 claims 1
- KXDRZERGRDJYHW-UHFFFAOYSA-N 2-[3-[benzyl(propan-2-yl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C(C)C)CC1=CC=CC=C1 KXDRZERGRDJYHW-UHFFFAOYSA-N 0.000 claims 1
- ZEKCAHDDTLXELM-UHFFFAOYSA-N 2-[3-[benzyl(propan-2-yl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C(C)C)CC1=CC=CC=C1 ZEKCAHDDTLXELM-UHFFFAOYSA-N 0.000 claims 1
- YYQRSTZFCROPLB-CILPGNKCSA-N 2-[3-[benzyl-[(1r)-1-phenylethyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N([C@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 YYQRSTZFCROPLB-CILPGNKCSA-N 0.000 claims 1
- YFXFHBVBMXKNRV-HJZHLRNFSA-N 2-[3-[benzyl-[(1r)-1-phenylethyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N([C@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 YFXFHBVBMXKNRV-HJZHLRNFSA-N 0.000 claims 1
- YYQRSTZFCROPLB-XEGCMXMBSA-N 2-[3-[benzyl-[(1s)-1-phenylethyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N([C@@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 YYQRSTZFCROPLB-XEGCMXMBSA-N 0.000 claims 1
- QMRUXUSHTPZITI-UHFFFAOYSA-N 2-[3-[benzyl-[(2,5-difluorophenyl)methyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C(=CC=C(F)C=1)F)CC1=CC=CC=C1 QMRUXUSHTPZITI-UHFFFAOYSA-N 0.000 claims 1
- XZGUVUFKEBDRSU-UHFFFAOYSA-N 2-[3-[benzyl-[(2,5-difluorophenyl)methyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C(=CC=C(F)C=1)F)CC1=CC=CC=C1 XZGUVUFKEBDRSU-UHFFFAOYSA-N 0.000 claims 1
- DDEXZRWASXBCSW-UHFFFAOYSA-N 2-[3-[benzyl-[(3,5-difluorophenyl)methyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=C(F)C=C(F)C=1)CC1=CC=CC=C1 DDEXZRWASXBCSW-UHFFFAOYSA-N 0.000 claims 1
- PHDQSCONKMUMDV-UHFFFAOYSA-N 2-[3-[benzyl-[(3,5-difluorophenyl)methyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C=C(F)C=C(F)C=1)CC1=CC=CC=C1 PHDQSCONKMUMDV-UHFFFAOYSA-N 0.000 claims 1
- QDDGXBNRELUOIJ-UHFFFAOYSA-N 2-[3-[benzyl-[(3-fluorophenyl)methyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=C(F)C=CC=1)CC1=CC=CC=C1 QDDGXBNRELUOIJ-UHFFFAOYSA-N 0.000 claims 1
- JQOAYYKPJRZBMC-UHFFFAOYSA-N 2-[3-[benzyl-[(3-fluorophenyl)methyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C=C(F)C=CC=1)CC1=CC=CC=C1 JQOAYYKPJRZBMC-UHFFFAOYSA-N 0.000 claims 1
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- JRLOGICUPYGMEA-UHFFFAOYSA-N 2-[3-[benzyl-[(4-chloro-2-fluorophenyl)methyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C(=CC(Cl)=CC=1)F)CC1=CC=CC=C1 JRLOGICUPYGMEA-UHFFFAOYSA-N 0.000 claims 1
- RTJLUGBGPMGMNA-UHFFFAOYSA-N 2-[3-[benzyl-[(4-fluorophenyl)methyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=CC(F)=CC=1)CC1=CC=CC=C1 RTJLUGBGPMGMNA-UHFFFAOYSA-N 0.000 claims 1
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- RQIIHGXNQKTERU-UHFFFAOYSA-N 2-[3-[benzyl-[2-(2,6-dichlorophenyl)ethyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C=CC=CC=1)CCC1=C(Cl)C=CC=C1Cl RQIIHGXNQKTERU-UHFFFAOYSA-N 0.000 claims 1
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- RCXQKTXYPWPUBD-UHFFFAOYSA-N 2-[3-[benzyl-[2-(3-fluorophenyl)ethyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C=CC=CC=1)CCC1=CC=CC(F)=C1 RCXQKTXYPWPUBD-UHFFFAOYSA-N 0.000 claims 1
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- QXAWNWMIFSFLQN-UHFFFAOYSA-N 2-[3-[benzyl-[2-(4-fluorophenyl)ethyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=CC=CC=1)CCC1=CC=C(F)C=C1 QXAWNWMIFSFLQN-UHFFFAOYSA-N 0.000 claims 1
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- CHNYJHQCXQPCQT-UHFFFAOYSA-N 2-[3-[benzyl-[[2-(trifluoromethyl)phenyl]methyl]carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(CC=1C(=CC=CC=1)C(F)(F)F)CC1=CC=CC=C1 CHNYJHQCXQPCQT-UHFFFAOYSA-N 0.000 claims 1
- UDDXIMBXSNAVHL-UHFFFAOYSA-N 2-[3-[benzyl-[[3-(trifluoromethyl)phenyl]methyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCC1C(=O)N(CC=1C=C(C=CC=1)C(F)(F)F)CC1=CC=CC=C1 UDDXIMBXSNAVHL-UHFFFAOYSA-N 0.000 claims 1
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- UNAJWEICGRIWJK-UHFFFAOYSA-N 2-[3-[cyclohexyl(phenyl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C=1C=CC=CC=1)C1CCCCC1 UNAJWEICGRIWJK-UHFFFAOYSA-N 0.000 claims 1
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- HCRCBWLXZLMJLN-UHFFFAOYSA-N 2-[3-[ethyl(naphthalen-1-yl)carbamoyl]-3-methyl-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1=CC=C2C(N(C(=O)C3(C)CC4=C(N(C5=CC=CC=C54)CC(O)=O)CC3)CC)=CC=CC2=C1 HCRCBWLXZLMJLN-UHFFFAOYSA-N 0.000 claims 1
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- HSJXZPCBXVHZFF-UHFFFAOYSA-N 2-[3-[ethyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(CC)C1=CC=C(OC(F)(F)F)C=C1 HSJXZPCBXVHZFF-UHFFFAOYSA-N 0.000 claims 1
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- MORVHPCBRAKGKD-UHFFFAOYSA-N 2-[3-[methyl-(2-methylphenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1C MORVHPCBRAKGKD-UHFFFAOYSA-N 0.000 claims 1
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- KUHJBORJWOBFDJ-UHFFFAOYSA-N 2-[3-ethyl-3-[(3-fluorophenyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CC)C(=O)NC1=CC=CC(F)=C1 KUHJBORJWOBFDJ-UHFFFAOYSA-N 0.000 claims 1
- CSZXHXPDHCWUKP-UHFFFAOYSA-N 2-[3-ethyl-3-[(4-fluorophenyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CC)C(=O)NC1=CC=C(F)C=C1 CSZXHXPDHCWUKP-UHFFFAOYSA-N 0.000 claims 1
- JQRXDQQTLXAVEV-UHFFFAOYSA-N 2-[3-ethyl-3-[methyl(phenyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(CC)C(=O)N(C)C1=CC=CC=C1 JQRXDQQTLXAVEV-UHFFFAOYSA-N 0.000 claims 1
- NACVFFNMFQBHTN-UHFFFAOYSA-N 2-[3-methyl-3-(naphthalen-1-ylmethylcarbamoyl)-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1=CC=C2C(CNC(=O)C3(CC4=C(N(C5=CC=CC=C54)CC(O)=O)CC3)C)=CC=CC2=C1 NACVFFNMFQBHTN-UHFFFAOYSA-N 0.000 claims 1
- PRDBTTSXUGNBCC-UHFFFAOYSA-N 2-[3-methyl-3-(phenylcarbamoyl)-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)NC1=CC=CC=C1 PRDBTTSXUGNBCC-UHFFFAOYSA-N 0.000 claims 1
- DXSCNAXIPZWCAI-UHFFFAOYSA-N 2-[3-methyl-3-[(2-methylsulfanylphenyl)methylcarbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound CSC1=CC=CC=C1CNC(=O)C1(C)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 DXSCNAXIPZWCAI-UHFFFAOYSA-N 0.000 claims 1
- FPEGCQKINVUSFJ-UHFFFAOYSA-N 2-[3-methyl-3-[(4-pentylphenyl)methylcarbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1(C)CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 FPEGCQKINVUSFJ-UHFFFAOYSA-N 0.000 claims 1
- OUSLFGZHODXDCS-UHFFFAOYSA-N 2-[3-methyl-3-[methyl(phenyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)C1=CC=CC=C1 OUSLFGZHODXDCS-UHFFFAOYSA-N 0.000 claims 1
- HMMINQTVNRESJZ-UHFFFAOYSA-N 2-[3-methyl-3-[methyl-(2-methylphenyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C)C1=CC=CC=C1C HMMINQTVNRESJZ-UHFFFAOYSA-N 0.000 claims 1
- KPYKIKABJIETRH-UHFFFAOYSA-N 2-[3-methyl-3-[phenyl(2-phenylethyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C=1C=CC=CC=1)CCC1=CC=CC=C1 KPYKIKABJIETRH-UHFFFAOYSA-N 0.000 claims 1
- ZPKFRPWRALYOGS-UHFFFAOYSA-N 2-[3-methyl-3-[phenyl(3-phenylpropyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C=1C=CC=CC=1)CCCC1=CC=CC=C1 ZPKFRPWRALYOGS-UHFFFAOYSA-N 0.000 claims 1
- VTFAFSUGTOXXDV-UHFFFAOYSA-N 2-[3-methyl-3-[phenyl(propan-2-yl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C(C)C)C1=CC=CC=C1 VTFAFSUGTOXXDV-UHFFFAOYSA-N 0.000 claims 1
- MLLSNLQKXNGRSF-UHFFFAOYSA-N 2-[3-methyl-3-[phenyl(thiophen-3-ylmethyl)carbamoyl]-2,4-dihydro-1h-carbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=CC=C22)CC(O)=O)=C2CC1(C)C(=O)N(C=1C=CC=CC=1)CC=1C=CSC=1 MLLSNLQKXNGRSF-UHFFFAOYSA-N 0.000 claims 1
- CANGIYSPIOPEFC-UHFFFAOYSA-N 2-[6-bromo-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(Br)C=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 CANGIYSPIOPEFC-UHFFFAOYSA-N 0.000 claims 1
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- ORQPLAJHTWGVTP-UHFFFAOYSA-N 2-[6-cyano-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(C=C22)C#N)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 ORQPLAJHTWGVTP-UHFFFAOYSA-N 0.000 claims 1
- LNUFCGFIZBQTGA-UHFFFAOYSA-N 2-[6-iodo-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(I)C=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 LNUFCGFIZBQTGA-UHFFFAOYSA-N 0.000 claims 1
- XNFLYRQAOMHMNY-UHFFFAOYSA-N 2-[6-methoxy-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC(OC)=CC=C3N(CC(O)=O)C=2CCC1C(=O)N(C)C1=CC=CC=C1 XNFLYRQAOMHMNY-UHFFFAOYSA-N 0.000 claims 1
- OEWQOQXUJANSCE-UHFFFAOYSA-N 2-[6-methyl-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC=C(C)C=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 OEWQOQXUJANSCE-UHFFFAOYSA-N 0.000 claims 1
- REDSNJHNOXFTQK-UHFFFAOYSA-N 2-[7-chloro-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC(Cl)=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 REDSNJHNOXFTQK-UHFFFAOYSA-N 0.000 claims 1
- KEBFDVKIAPEZHP-UHFFFAOYSA-N 2-[7-methyl-3-[methyl(phenyl)carbamoyl]-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC(N(C2=CC(C)=CC=C22)CC(O)=O)=C2CC1C(=O)N(C)C1=CC=CC=C1 KEBFDVKIAPEZHP-UHFFFAOYSA-N 0.000 claims 1
- HGTHQVQHYSHUKP-UHFFFAOYSA-N 2-[8-chloro-3-(2,2-diphenylethylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C=2C3=CC=CC(Cl)=C3N(CC(=O)O)C=2CCC1C(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 HGTHQVQHYSHUKP-UHFFFAOYSA-N 0.000 claims 1
- JTOKVIITSQGXTA-UHFFFAOYSA-N 2-[8-chloro-3-(2,3-dihydro-1h-inden-2-ylcarbamoyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1CCC(N(C2=C(Cl)C=CC=C22)CC(=O)O)=C2C1 JTOKVIITSQGXTA-UHFFFAOYSA-N 0.000 claims 1
- ZRCHEFBVPFYICW-UHFFFAOYSA-N 2-[8-chloro-3-(2,3-dihydroindole-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]acetic acid Chemical compound C1CC2=CC=CC=C2N1C(=O)C1CCC(N(C2=C(Cl)C=CC=C22)CC(=O)O)=C2C1 ZRCHEFBVPFYICW-UHFFFAOYSA-N 0.000 claims 1
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- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
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- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 208000016557 Acute basophilic leukemia Diseases 0.000 claims 1
- 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims 1
- 206010002199 Anaphylactic shock Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
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- 239000002253 acid Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
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- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 1
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- 125000005164 aryl thioalkyl group Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- XXRGLCKZBCIEKO-DLMDZQPMSA-N azocine Chemical compound C/1=C/C=C\N=C/C=C\1 XXRGLCKZBCIEKO-DLMDZQPMSA-N 0.000 claims 1
- 210000003651 basophil Anatomy 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 150000007655 dibenzoazepines Chemical group 0.000 claims 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003979 eosinophil Anatomy 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000020932 food allergy Nutrition 0.000 claims 1
- 125000004967 formylalkyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 210000003630 histaminocyte Anatomy 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 206010024378 leukocytosis Diseases 0.000 claims 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001326 naphthylalkyl group Chemical group 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- 230000009885 systemic effect Effects 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
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Classifications
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- 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
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
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- Immunology (AREA)
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- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2004014719 | 2004-12-27 | ||
| PCT/IB2005/054380 WO2006070325A2 (en) | 2004-12-27 | 2005-12-22 | 2,3,4,9-tetrahydro-1h-carbazole derivatives as crth2 receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110773T1 true HRP20110773T1 (hr) | 2011-11-30 |
Family
ID=36499938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110773T HRP20110773T1 (hr) | 2004-12-27 | 2011-10-24 | Derivati 2,3,4,9-tetrahidro-1h-karbazola kao antagonisti crth2 receptora |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8039474B2 (es) |
| EP (1) | EP1833791B1 (es) |
| JP (1) | JP5137240B2 (es) |
| KR (1) | KR101329903B1 (es) |
| CN (1) | CN101084190B (es) |
| AR (1) | AR052549A1 (es) |
| AT (1) | ATE518834T1 (es) |
| AU (1) | AU2005320964B2 (es) |
| BR (1) | BRPI0519280A2 (es) |
| CA (1) | CA2594280C (es) |
| CY (1) | CY1112376T1 (es) |
| DK (1) | DK1833791T3 (es) |
| ES (1) | ES2369782T3 (es) |
| HK (1) | HK1111698A1 (es) |
| HR (1) | HRP20110773T1 (es) |
| IL (1) | IL184233A0 (es) |
| MX (1) | MX2007007691A (es) |
| MY (1) | MY144897A (es) |
| NO (1) | NO20073059L (es) |
| NZ (1) | NZ556657A (es) |
| PL (1) | PL1833791T3 (es) |
| PT (1) | PT1833791E (es) |
| RU (1) | RU2404163C2 (es) |
| SI (1) | SI1833791T1 (es) |
| TW (1) | TW200633978A (es) |
| WO (1) | WO2006070325A2 (es) |
| ZA (1) | ZA200705085B (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4051398B2 (ja) | 2004-03-11 | 2008-02-20 | アクテリオン ファマシューティカルズ リミテッド | テトラヒドロピリドインドール誘導体 |
| PL2051962T3 (pl) * | 2006-08-07 | 2012-03-30 | Actelion Pharmaceuticals Ltd | Pochodne kwasu (3-amino-1,2,3,4-tetrahydro-9h-karbazol-9-ilo)-octowego |
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