CA2618888A1 - Acyltryptophanols - Google Patents
Acyltryptophanols Download PDFInfo
- Publication number
- CA2618888A1 CA2618888A1 CA002618888A CA2618888A CA2618888A1 CA 2618888 A1 CA2618888 A1 CA 2618888A1 CA 002618888 A CA002618888 A CA 002618888A CA 2618888 A CA2618888 A CA 2618888A CA 2618888 A1 CA2618888 A1 CA 2618888A1
- Authority
- CA
- Canada
- Prior art keywords
- indol
- ethyl
- carboxylic acid
- hydroxymethyl
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 230000035558 fertility Effects 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 3
- -1 cyano, hydroxy, amino Chemical group 0.000 claims description 915
- 125000003118 aryl group Chemical group 0.000 claims description 883
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 461
- 150000001408 amides Chemical class 0.000 claims description 219
- 239000002253 acid Substances 0.000 claims description 125
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 238000000034 method Methods 0.000 claims description 93
- UDQCRUSSQAXPJY-SECBINFHSA-N (2r)-2-amino-3-(1h-indol-3-yl)propan-1-ol Chemical compound C1=CC=C2C(C[C@H](CO)N)=CNC2=C1 UDQCRUSSQAXPJY-SECBINFHSA-N 0.000 claims description 81
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 78
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000003368 amide group Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- IHRRZJBDASDGSN-UHFFFAOYSA-N 5-(4-carboxyphenyl)-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 IHRRZJBDASDGSN-UHFFFAOYSA-N 0.000 claims description 16
- UDQCRUSSQAXPJY-VIFPVBQESA-N (2s)-2-amino-3-(1h-indol-3-yl)propan-1-ol Chemical class C1=CC=C2C(C[C@@H](CO)N)=CNC2=C1 UDQCRUSSQAXPJY-VIFPVBQESA-N 0.000 claims description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- RNFWRHMJKHHARO-UHFFFAOYSA-N 4-(3-carboxy-4-propoxyphenyl)-2-chlorobenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=C(C(O)=O)C(Cl)=C1 RNFWRHMJKHHARO-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- QJUWRKCCZCHCSW-UHFFFAOYSA-N 5-(3-carboxyphenyl)-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=CC(C(O)=O)=C1 QJUWRKCCZCHCSW-UHFFFAOYSA-N 0.000 claims description 6
- 238000010640 amide synthesis reaction Methods 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- VWEBEGUKOJAQHO-OAHLLOKOSA-N 5-bromo-2-ethoxy-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]benzamide Chemical compound CCOC1=CC=C(Br)C=C1C(=O)N[C@@H](CO)CC1=CNC2=CC=CC=C12 VWEBEGUKOJAQHO-OAHLLOKOSA-N 0.000 claims description 5
- GVWZOHCRCIZRJC-UHFFFAOYSA-N 6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 GVWZOHCRCIZRJC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- MVKDRQGJIZRKMS-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1C1=CC(OC)=CC=C1OC MVKDRQGJIZRKMS-UHFFFAOYSA-N 0.000 claims description 4
- AHPKLZHEOLAGBH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC=C(OC)C(OC)=C1 AHPKLZHEOLAGBH-UHFFFAOYSA-N 0.000 claims description 4
- ZHMOUFNQOCNKFH-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)quinoline-4-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(C=2N=C3C=CC=CC3=C(C(O)=O)C=2)=C1 ZHMOUFNQOCNKFH-UHFFFAOYSA-N 0.000 claims description 4
- JMINLRNQEQPSQF-GQCTYLIASA-N 2-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1\C=C\C1=CC=C(OC)C(OC)=C1 JMINLRNQEQPSQF-GQCTYLIASA-N 0.000 claims description 4
- DJUGVJNNVDZYJY-UHFFFAOYSA-N 5-(3-carboxy-5-fluorophenyl)-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC(F)=CC(C(O)=O)=C1 DJUGVJNNVDZYJY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- MUGDLJMARICTGJ-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1C(=O)N[C@@H](CO)CC1=CNC2=CC=CC=C12 MUGDLJMARICTGJ-LJQANCHMSA-N 0.000 claims description 4
- OSNDDMIESOZTFT-AVKWCDSFSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-[2-[(3,4,5-trimethoxyphenyl)methoxy]phenyl]propanamide Chemical compound COC1=C(OC)C(OC)=CC(COC=2C(=CC=CC=2)C(C)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 OSNDDMIESOZTFT-AVKWCDSFSA-N 0.000 claims description 4
- XNGICTBETJUBPC-HSZRJFAPSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-5-[4-(hydroxymethyl)phenyl]-2-propoxybenzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(CO)C=C1 XNGICTBETJUBPC-HSZRJFAPSA-N 0.000 claims description 4
- UHEBAVPPISSUOL-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-6-methoxyquinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC=CC(O)=C1 UHEBAVPPISSUOL-UHFFFAOYSA-N 0.000 claims description 3
- BUUDAWXFLYKBSX-HXUWFJFHSA-N 2-(4-chloro-3-methylphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound C1=C(Cl)C(C)=CC(C=2N=C3C=CC=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 BUUDAWXFLYKBSX-HXUWFJFHSA-N 0.000 claims description 3
- MMVARAJLTBCVOB-UHFFFAOYSA-N 2-[2-[(3,4,5-trimethoxyphenyl)methoxy]phenyl]propanoic acid Chemical compound COC1=C(OC)C(OC)=CC(COC=2C(=CC=CC=2)C(C)C(O)=O)=C1 MMVARAJLTBCVOB-UHFFFAOYSA-N 0.000 claims description 3
- UXINVXZOYWCOJW-UHFFFAOYSA-N 2-amino-3-(5-fluoro-1h-indol-3-yl)propan-1-ol Chemical compound C1=C(F)C=C2C(CC(CO)N)=CNC2=C1 UXINVXZOYWCOJW-UHFFFAOYSA-N 0.000 claims description 3
- PUOCXKWXBSFIIC-UHFFFAOYSA-N 2-ethoxy-5-(3-methoxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC=C1C1=CC=CC(OC)=C1 PUOCXKWXBSFIIC-UHFFFAOYSA-N 0.000 claims description 3
- PSIQOHAKCWUAJB-UHFFFAOYSA-N 2-hydroxy-5-(3,4,5-trimethoxyphenyl)benzoic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(C(O)=CC=2)C(O)=O)=C1 PSIQOHAKCWUAJB-UHFFFAOYSA-N 0.000 claims description 3
- NFHOPCREVMHGOH-UHFFFAOYSA-N 2-methoxy-5-(3-methoxyphenyl)benzoic acid Chemical compound COC1=CC=CC(C=2C=C(C(OC)=CC=2)C(O)=O)=C1 NFHOPCREVMHGOH-UHFFFAOYSA-N 0.000 claims description 3
- AIRIPHYCXWJIOW-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-2-methoxybenzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(OC)C(C(O)=O)=C1 AIRIPHYCXWJIOW-UHFFFAOYSA-N 0.000 claims description 3
- CAYBPDDYISIAJG-UHFFFAOYSA-N 5-phenyl-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=CC=C1 CAYBPDDYISIAJG-UHFFFAOYSA-N 0.000 claims description 3
- SXJFAWMKEIQWDM-HXUWFJFHSA-N 6-amino-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(N)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 SXJFAWMKEIQWDM-HXUWFJFHSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- QDQSIGNHRHNRKE-SNVBAGLBSA-N (2r)-2-amino-3-(1-methylindol-3-yl)propan-1-ol Chemical compound C1=CC=C2N(C)C=C(C[C@@H](N)CO)C2=C1 QDQSIGNHRHNRKE-SNVBAGLBSA-N 0.000 claims description 2
- HFWXSNNQARNZHK-UHFFFAOYSA-N 1-methoxy-4-(3,4,5-trimethoxyphenyl)cyclohexa-2,4-diene-1-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2C=CC(OC)(CC=2)C(O)=O)=C1 HFWXSNNQARNZHK-UHFFFAOYSA-N 0.000 claims description 2
- VKTDHGSBLIWYGG-GOSISDBHSA-N 2-(2,5-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-5-methoxybenzamide Chemical compound N([C@@H](CO)CC=1C2=CC=CC=C2NC=1)C(=O)C1=CC(OC)=CC=C1C1=CC(OC)=CC=C1OC VKTDHGSBLIWYGG-GOSISDBHSA-N 0.000 claims description 2
- QZBUYUFVMJZUFK-GOSISDBHSA-N 2-(2,5-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]benzamide Chemical compound COC1=CC=C(OC)C(C=2C(=CC=CC=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 QZBUYUFVMJZUFK-GOSISDBHSA-N 0.000 claims description 2
- SMJUUSFLYVEWEA-UHFFFAOYSA-N 2-(3,4,5-trifluorophenyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SMJUUSFLYVEWEA-UHFFFAOYSA-N 0.000 claims description 2
- KJVBOCSWECLACJ-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2SC=C(N=2)C(O)=O)=C1 KJVBOCSWECLACJ-UHFFFAOYSA-N 0.000 claims description 2
- ANMMTUGOJDVLLQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methylbenzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C)C=CC=C1C(O)=O ANMMTUGOJDVLLQ-UHFFFAOYSA-N 0.000 claims description 2
- HRGXEGKDPWGCFS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1C1=CC=C(OC)C(OC)=C1 HRGXEGKDPWGCFS-UHFFFAOYSA-N 0.000 claims description 2
- UEJWSHFSBXUNHR-LJQANCHMSA-N 2-(3,4-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-5-methoxybenzamide Chemical compound N([C@@H](CO)CC=1C2=CC=CC=C2NC=1)C(=O)C1=CC(OC)=CC=C1C1=CC=C(OC)C(OC)=C1 UEJWSHFSBXUNHR-LJQANCHMSA-N 0.000 claims description 2
- JCIXGDCUXFJWNX-OAQYLSRUSA-N 2-(3,4-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-3-methylquinoline-4-carboxamide Chemical compound CC1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C2=CC(OC)=CC=C2N=C1C1=CC=C(OC)C(OC)=C1 JCIXGDCUXFJWNX-OAQYLSRUSA-N 0.000 claims description 2
- BMPFOXPPUQEHPB-LJQANCHMSA-N 2-(3,4-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=CC=C1C(=O)N[C@@H](CO)CC1=CNC2=CC=CC=C12 BMPFOXPPUQEHPB-LJQANCHMSA-N 0.000 claims description 2
- LVERPCFCTGLVSP-HXUWFJFHSA-N 2-(3,4-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C(C=CC=C2)C2=N1 LVERPCFCTGLVSP-HXUWFJFHSA-N 0.000 claims description 2
- LVERPCFCTGLVSP-FQEVSTJZSA-N 2-(3,4-dimethoxyphenyl)-n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C(=O)N[C@H](CO)CC=2C3=CC=CC=C3NC=2)=C(C=CC=C2)C2=N1 LVERPCFCTGLVSP-FQEVSTJZSA-N 0.000 claims description 2
- YEEOQKNBTLLPHJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=CC=C1C(O)=O YEEOQKNBTLLPHJ-UHFFFAOYSA-N 0.000 claims description 2
- UBYGJSBZQUJOCS-UHFFFAOYSA-N 2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC(F)=C(OC)C(F)=C1 UBYGJSBZQUJOCS-UHFFFAOYSA-N 0.000 claims description 2
- MOJFONSQPPMBAW-OAQYLSRUSA-N 2-(3,5-difluoro-4-methoxyphenyl)-n-[(2r)-1-hydroxy-3-(1-propan-2-ylindol-3-yl)propan-2-yl]-6-methoxyquinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(C(C)C)C=2)C2=CC(OC)=CC=C2N=C1C1=CC(F)=C(OC)C(F)=C1 MOJFONSQPPMBAW-OAQYLSRUSA-N 0.000 claims description 2
- PFCIQEZGLWFOFJ-GOSISDBHSA-N 2-(3,5-difluoro-4-methoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxyquinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C2=CC(OC)=CC=C2N=C1C1=CC(F)=C(OC)C(F)=C1 PFCIQEZGLWFOFJ-GOSISDBHSA-N 0.000 claims description 2
- NUWNNKFUIGYILM-HXUWFJFHSA-N 2-(3,5-dimethoxyphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound COC1=CC(OC)=CC(C=2N=C3C=CC=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 NUWNNKFUIGYILM-HXUWFJFHSA-N 0.000 claims description 2
- PMYWHQSNWLBYCO-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound COC1=CC(OC)=CC(C=2N=C3C=CC=CC3=C(C(O)=O)C=2)=C1 PMYWHQSNWLBYCO-UHFFFAOYSA-N 0.000 claims description 2
- WCUUPYUZAQBRMU-UHFFFAOYSA-N 2-(3-cyanopropoxy)-5-(3,4,5-trimethoxyphenyl)benzoic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(C(OCCCC#N)=CC=2)C(O)=O)=C1 WCUUPYUZAQBRMU-UHFFFAOYSA-N 0.000 claims description 2
- WKZYFADQYZBVSV-UHFFFAOYSA-N 2-(3-ethylphenyl)-6-methoxyquinoline-4-carboxylic acid Chemical compound CCC1=CC=CC(C=2N=C3C=CC(OC)=CC3=C(C(O)=O)C=2)=C1 WKZYFADQYZBVSV-UHFFFAOYSA-N 0.000 claims description 2
- FHWDCKPKWBYLJV-JOCHJYFZSA-N 2-(3-ethylphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxyquinoline-4-carboxamide Chemical compound CCC1=CC=CC(C=2N=C3C=CC(OC)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 FHWDCKPKWBYLJV-JOCHJYFZSA-N 0.000 claims description 2
- GVUQENXVMGBDBI-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1C1=CC=C(OC)C(F)=C1 GVUQENXVMGBDBI-UHFFFAOYSA-N 0.000 claims description 2
- CIPVDERRKPTLRA-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6,8-dimethylquinoline-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(O)=O)=C(C=C(C)C=C2C)C2=N1 CIPVDERRKPTLRA-UHFFFAOYSA-N 0.000 claims description 2
- WHOGPEAOFUQMBB-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-(trifluoromethoxy)quinoline-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(O)=O)=C(C=C(OC(F)(F)F)C=C2)C2=N1 WHOGPEAOFUQMBB-UHFFFAOYSA-N 0.000 claims description 2
- XJNNWSRVIDOHPS-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-iodoquinazoline-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=NC(C(O)=O)=C(C=C(I)C=C2)C2=N1 XJNNWSRVIDOHPS-UHFFFAOYSA-N 0.000 claims description 2
- NOJWVURXZADETK-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-iodoquinoline-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(O)=O)=C(C=C(I)C=C2)C2=N1 NOJWVURXZADETK-UHFFFAOYSA-N 0.000 claims description 2
- MKKNOFAPGWTHNA-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid Chemical compound N1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC=C(OC)C(F)=C1 MKKNOFAPGWTHNA-UHFFFAOYSA-N 0.000 claims description 2
- HOWSYYUOKVLPRA-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC=C(OC)C(F)=C1 HOWSYYUOKVLPRA-UHFFFAOYSA-N 0.000 claims description 2
- RIWSSNGEHPCPCQ-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-methylpyridine-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(O)=O)=CC(C)=N1 RIWSSNGEHPCPCQ-UHFFFAOYSA-N 0.000 claims description 2
- ARTKGSJEDDIBMK-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-methylpyrimidine-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=NC(C)=CC(C(O)=O)=N1 ARTKGSJEDDIBMK-UHFFFAOYSA-N 0.000 claims description 2
- JUMWJVINNGQMHP-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-6-methylquinoline-4-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(O)=O)=C(C=C(C)C=C2)C2=N1 JUMWJVINNGQMHP-UHFFFAOYSA-N 0.000 claims description 2
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- DLFPEFDATPDVTR-UHFFFAOYSA-N 5-[3-(dimethylsulfamoyl)phenyl]-n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(S(=O)(=O)N(C)C)=C1 DLFPEFDATPDVTR-UHFFFAOYSA-N 0.000 claims description 2
- DSGKZOLETPURGH-UHFFFAOYSA-N 5-[3-(methylcarbamoyl)phenyl]-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=CC(C(=O)NC)=C1 DSGKZOLETPURGH-UHFFFAOYSA-N 0.000 claims description 2
- OJZGUKDYTSRHAD-XMMPIXPASA-N 5-[3-[2-(dimethylamino)ethoxy]phenyl]-2-ethoxy-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]benzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCC)=CC=C1C1=CC=CC(OCCN(C)C)=C1 OJZGUKDYTSRHAD-XMMPIXPASA-N 0.000 claims description 2
- QGRWWSJXUNCGJV-UHFFFAOYSA-N 5-[3-[butyl(methylcarbamoyl)amino]phenyl]-2-cyclopentyloxybenzoic acid Chemical compound CCCCN(C(=O)NC)C1=CC=CC(C=2C=C(C(OC3CCCC3)=CC=2)C(O)=O)=C1 QGRWWSJXUNCGJV-UHFFFAOYSA-N 0.000 claims description 2
- WCCGAOGPULHNLK-RUZDIDTESA-N 5-[3-[butyl(methylcarbamoyl)amino]phenyl]-2-ethoxy-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]benzamide Chemical compound CCCCN(C(=O)NC)C1=CC=CC(C=2C=C(C(OCC)=CC=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 WCCGAOGPULHNLK-RUZDIDTESA-N 0.000 claims description 2
- HHMXGMQXNWBYKD-UHFFFAOYSA-N 5-[3-[butyl(methylcarbamoyl)amino]phenyl]-2-methoxy-3-methylbenzoic acid Chemical compound CCCCN(C(=O)NC)C1=CC=CC(C=2C=C(C(OC)=C(C)C=2)C(O)=O)=C1 HHMXGMQXNWBYKD-UHFFFAOYSA-N 0.000 claims description 2
- PJYNUZAVKJDQFH-UHFFFAOYSA-N 5-[3-[butyl(methylcarbamoyl)amino]phenyl]-2-methoxybenzoic acid Chemical compound CCCCN(C(=O)NC)C1=CC=CC(C=2C=C(C(OC)=CC=2)C(O)=O)=C1 PJYNUZAVKJDQFH-UHFFFAOYSA-N 0.000 claims description 2
- HQDOIAKNWOCCKX-UHFFFAOYSA-N 5-[3-[butyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenyl]-2-propoxybenzoic acid Chemical compound CCCCN(C(=O)OC(C)(C)C)C1=CC=CC(C=2C=C(C(OCCC)=CC=2)C(O)=O)=C1 HQDOIAKNWOCCKX-UHFFFAOYSA-N 0.000 claims description 2
- HQGAGTBSNGWIQL-HSZRJFAPSA-N 5-[4-(cyanomethyl)phenyl]-2-ethoxy-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]benzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCC)=CC=C1C1=CC=C(CC#N)C=C1 HQGAGTBSNGWIQL-HSZRJFAPSA-N 0.000 claims description 2
- PZUZIRLZKOEMKN-RUZDIDTESA-N 5-[4-(cyanomethyl)phenyl]-n-[(2r)-1-hydroxy-3-(1-methylindol-3-yl)propan-2-yl]-2-propoxybenzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(C)C=2)C(OCCC)=CC=C1C1=CC=C(CC#N)C=C1 PZUZIRLZKOEMKN-RUZDIDTESA-N 0.000 claims description 2
- XIOKSSWAVXZKLB-HSZRJFAPSA-N 5-[4-(dimethylamino)phenyl]-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-propoxybenzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(N(C)C)C=C1 XIOKSSWAVXZKLB-HSZRJFAPSA-N 0.000 claims description 2
- FEYDMYAPMKIWQS-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(N(C)C)C=C1 FEYDMYAPMKIWQS-UHFFFAOYSA-N 0.000 claims description 2
- WWRWUGCLRLKALC-HSZRJFAPSA-N 5-[4-(dimethylsulfamoyl)phenyl]-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-propoxybenzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 WWRWUGCLRLKALC-HSZRJFAPSA-N 0.000 claims description 2
- CHJIFMLMDFTNML-UHFFFAOYSA-N 5-[4-(dimethylsulfamoyl)phenyl]-n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 CHJIFMLMDFTNML-UHFFFAOYSA-N 0.000 claims description 2
- SVJICGTYNVAZMQ-LLVKDONJSA-N 5-bromo-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-4-methoxythiophene-3-carboxamide Chemical compound COC1=C(Br)SC=C1C(=O)N[C@@H](CO)CC1=CNC2=CC=CC=C12 SVJICGTYNVAZMQ-LLVKDONJSA-N 0.000 claims description 2
- YERUHCZAHLZZFK-UHFFFAOYSA-N 5-methoxy-2-(3,4,5-trifluorophenyl)benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1C1=CC(F)=C(F)C(F)=C1 YERUHCZAHLZZFK-UHFFFAOYSA-N 0.000 claims description 2
- WENSKPWTFNQPRW-UHFFFAOYSA-N 5-methoxy-2-(3-propan-2-ylphenyl)benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1C1=CC=CC(C(C)C)=C1 WENSKPWTFNQPRW-UHFFFAOYSA-N 0.000 claims description 2
- ZDZONSIVUHZSKM-XMMPIXPASA-N 6-(4-hydroxybut-1-ynyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)C#CCCO)=C1 ZDZONSIVUHZSKM-XMMPIXPASA-N 0.000 claims description 2
- VWDUAMCLXCMAEK-UHFFFAOYSA-N 6-(4-methoxyphenyl)pyrimidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(C(O)=O)=NC=N1 VWDUAMCLXCMAEK-UHFFFAOYSA-N 0.000 claims description 2
- MKJCJJZVJWTNQW-GOSISDBHSA-N 6-bromo-2-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound S1C(C)=NC(C)=C1C1=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C(C=C(Br)C=C2)C2=N1 MKJCJJZVJWTNQW-GOSISDBHSA-N 0.000 claims description 2
- WEKZZSIOPXMVNW-UHFFFAOYSA-N 6-bromo-2-(2,4-dimethyl-1,3-thiazol-5-yl)quinoline-4-carboxylic acid Chemical compound S1C(C)=NC(C)=C1C1=CC(C(O)=O)=C(C=C(Br)C=C2)C2=N1 WEKZZSIOPXMVNW-UHFFFAOYSA-N 0.000 claims description 2
- SENFUICUVRWPLJ-CYBMUJFWSA-N 6-bromo-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-1h-benzimidazole-4-carboxamide Chemical compound N([C@H](CC=1C2=CC=CC=C2NC=1)CO)C(=O)C1=CC(Br)=CC2=C1N=CN2 SENFUICUVRWPLJ-CYBMUJFWSA-N 0.000 claims description 2
- UDBCEANUDMJODE-LJQANCHMSA-N 6-bromo-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)-1,8-naphthyridine-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3N=CC(Br)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 UDBCEANUDMJODE-LJQANCHMSA-N 0.000 claims description 2
- QNGDHTVSEUPCJW-HXUWFJFHSA-N 6-bromo-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(Br)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 QNGDHTVSEUPCJW-HXUWFJFHSA-N 0.000 claims description 2
- ZWXXRURKWGRUSA-MRXNPFEDSA-N 6-bromo-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-8-carboxamide Chemical compound C1=CN=C2C(C(=O)N[C@H](CC=3C4=CC=CC=C4NC=3)CO)=CC(Br)=CC2=C1 ZWXXRURKWGRUSA-MRXNPFEDSA-N 0.000 claims description 2
- IOJUDFWPSOPARH-UHFFFAOYSA-N 6-fluoro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(F)=CC3=C(C(O)=O)C=2)=C1 IOJUDFWPSOPARH-UHFFFAOYSA-N 0.000 claims description 2
- XKYROHLQMWKIMF-HXUWFJFHSA-N 6-fluoro-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(F)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 XKYROHLQMWKIMF-HXUWFJFHSA-N 0.000 claims description 2
- KPNCVRZUBOJCNN-UHFFFAOYSA-N 6-iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(I)=CC3=C(C(O)=O)C=2)=C1 KPNCVRZUBOJCNN-UHFFFAOYSA-N 0.000 claims description 2
- ZZKOEMJDKDRZKF-UHFFFAOYSA-N 6-methoxy-2-(2,3,4-trimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1=CC=C(OC)C(OC)=C1OC ZZKOEMJDKDRZKF-UHFFFAOYSA-N 0.000 claims description 2
- CNIZFNUNUJKQOE-UHFFFAOYSA-N 6-methoxy-2-(4-methoxy-1-benzofuran-2-yl)quinoline-4-carboxylic acid Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(C(O)=O)=C3)OC)=CC2=C1OC CNIZFNUNUJKQOE-UHFFFAOYSA-N 0.000 claims description 2
- YIMJUNZXXKDNRL-UHFFFAOYSA-N 6-methoxy-2-(5-methoxy-1-benzofuran-2-yl)quinoline-4-carboxylic acid Chemical compound C1=C(OC)C=CC2=NC(C=3OC4=CC=C(C=C4C=3)OC)=CC(C(O)=O)=C21 YIMJUNZXXKDNRL-UHFFFAOYSA-N 0.000 claims description 2
- KRWFLHVYBJOMLS-UHFFFAOYSA-N 6-methoxy-2-(5-methyl-1-benzofuran-2-yl)quinoline-4-carboxylic acid Chemical compound CC1=CC=C2OC(C3=NC4=CC=C(C=C4C(C(O)=O)=C3)OC)=CC2=C1 KRWFLHVYBJOMLS-UHFFFAOYSA-N 0.000 claims description 2
- QWMBXSBYODXLLZ-UHFFFAOYSA-N 6-methoxy-2-(6-methoxy-1-benzofuran-2-yl)quinoline-4-carboxylic acid Chemical compound C1=C(OC)C=CC2=NC(C3=CC4=CC=C(C=C4O3)OC)=CC(C(O)=O)=C21 QWMBXSBYODXLLZ-UHFFFAOYSA-N 0.000 claims description 2
- FZHZYTMPZJNWDE-UHFFFAOYSA-N 6-methoxy-2-(7-methyl-1-benzofuran-2-yl)quinoline-4-carboxylic acid Chemical compound C1=CC(C)=C2OC(C3=NC4=CC=C(C=C4C(C(O)=O)=C3)OC)=CC2=C1 FZHZYTMPZJNWDE-UHFFFAOYSA-N 0.000 claims description 2
- JRCAUBGQYGZGBU-UHFFFAOYSA-N 6-methoxy-2-[5-(trifluoromethoxy)-1-benzofuran-2-yl]quinoline-4-carboxylic acid Chemical compound FC(F)(F)OC1=CC=C2OC(C3=NC4=CC=C(C=C4C(C(O)=O)=C3)OC)=CC2=C1 JRCAUBGQYGZGBU-UHFFFAOYSA-N 0.000 claims description 2
- HIKZKGZNKNLBCR-UHFFFAOYSA-N 6-methyl-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(C)=CC3=C(C(O)=O)C=2)=C1 HIKZKGZNKNLBCR-UHFFFAOYSA-N 0.000 claims description 2
- FNFPFSCFQKVEDM-UHFFFAOYSA-N 6-nitro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(=CC3=C(C(O)=O)C=2)[N+]([O-])=O)=C1 FNFPFSCFQKVEDM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- AUVPHFRRYUJCJL-MUUNZHRXSA-N methyl (2r)-2-[[2-(3-fluoro-4-methoxyphenyl)-6-(trifluoromethoxy)quinoline-4-carbonyl]amino]-3-(1-propan-2-ylindol-3-yl)propanoate Chemical compound N([C@H](CC=1C2=CC=CC=C2N(C(C)C)C=1)C(=O)OC)C(=O)C(C1=CC(OC(F)(F)F)=CC=C1N=1)=CC=1C1=CC=C(OC)C(F)=C1 AUVPHFRRYUJCJL-MUUNZHRXSA-N 0.000 claims description 2
- YJKVJOBINWMLAG-MUUNZHRXSA-N methyl (2r)-2-[[2-(7-methoxy-1-benzofuran-2-yl)-6-(trifluoromethoxy)quinoline-4-carbonyl]amino]-3-(1-propan-2-ylindol-3-yl)propanoate Chemical compound C1=CC(OC)=C2OC(C=3C=C(C4=CC(OC(F)(F)F)=CC=C4N=3)C(=O)N[C@H](CC=3C4=CC=CC=C4N(C(C)C)C=3)C(=O)OC)=CC2=C1 YJKVJOBINWMLAG-MUUNZHRXSA-N 0.000 claims description 2
- SHHVNFDWCNBOTM-GDLZYMKVSA-N methyl (2r)-2-[[6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carbonyl]amino]-3-(1-propan-2-ylindol-3-yl)propanoate Chemical compound N([C@H](CC=1C2=CC=CC=C2N(C(C)C)C=1)C(=O)OC)C(=O)C(C1=CC(OC)=CC=C1N=1)=CC=1C1=CC(OC)=C(OC)C(OC)=C1 SHHVNFDWCNBOTM-GDLZYMKVSA-N 0.000 claims description 2
- RFVLOGSYFIRWDO-GDLZYMKVSA-N methyl (2r)-2-[[6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carbonyl]amino]-3-(1-propylindol-3-yl)propanoate Chemical compound N([C@H](CC1=CN(C2=CC=CC=C21)CCC)C(=O)OC)C(=O)C(C1=CC(OC)=CC=C1N=1)=CC=1C1=CC(OC)=C(OC)C(OC)=C1 RFVLOGSYFIRWDO-GDLZYMKVSA-N 0.000 claims description 2
- OHPBJRRNXJECEQ-SSEXGKCCSA-N methyl (2r)-2-[[6-methoxy-2-(3-methoxyphenyl)quinoline-4-carbonyl]amino]-3-(1-propan-2-ylindol-3-yl)propanoate Chemical compound N([C@H](CC=1C2=CC=CC=C2N(C(C)C)C=1)C(=O)OC)C(=O)C(C1=CC(OC)=CC=C1N=1)=CC=1C1=CC=CC(OC)=C1 OHPBJRRNXJECEQ-SSEXGKCCSA-N 0.000 claims description 2
- XDMAFCXUCGCRJI-JGCGQSQUSA-N methyl (2r)-3-(1-hexylindol-3-yl)-2-[[6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carbonyl]amino]propanoate Chemical compound N([C@H](CC1=CN(C2=CC=CC=C21)CCCCCC)C(=O)OC)C(=O)C(C1=CC(OC)=CC=C1N=1)=CC=1C1=CC(OC)=C(OC)C(OC)=C1 XDMAFCXUCGCRJI-JGCGQSQUSA-N 0.000 claims description 2
- SJHUMLLGELEZSO-HXUWFJFHSA-N methyl 2-[3-[[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]carbamoyl]phenyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 SJHUMLLGELEZSO-HXUWFJFHSA-N 0.000 claims description 2
- DIQJGPDVSIORNQ-JOCHJYFZSA-N methyl 3-[4-ethoxy-3-[[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]carbamoyl]phenyl]benzoate Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCC)=CC=C1C1=CC=CC(C(=O)OC)=C1 DIQJGPDVSIORNQ-JOCHJYFZSA-N 0.000 claims description 2
- YKKUHXALCYGWHP-HSZRJFAPSA-N methyl 4-[3-[[(2r)-1-hydroxy-3-(1-methylindol-3-yl)propan-2-yl]carbamoyl]-4-propoxyphenyl]-2-methoxybenzoate Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(C)C=2)C(OCCC)=CC=C1C1=CC=C(C(=O)OC)C(OC)=C1 YKKUHXALCYGWHP-HSZRJFAPSA-N 0.000 claims description 2
- LVTQGVHFMJKTPZ-JOCHJYFZSA-N methyl 4-[3-[[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]carbamoyl]-4-propoxyphenyl]-2-methoxybenzoate Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(C(=O)OC)C(OC)=C1 LVTQGVHFMJKTPZ-JOCHJYFZSA-N 0.000 claims description 2
- WGXMZFQLUHFROI-UHFFFAOYSA-N methyl 4-[3-[[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]carbamoyl]-4-propoxyphenyl]-2-methoxybenzoate Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(C(=O)OC)C(OC)=C1 WGXMZFQLUHFROI-UHFFFAOYSA-N 0.000 claims description 2
- RVWZOMHNKOGKDD-XMMPIXPASA-N n-[(2r)-1-(1-butylindol-3-yl)-3-hydroxypropan-2-yl]-3-(3-fluoro-4-methoxyphenyl)benzamide Chemical compound N([C@@H](CO)CC1=CN(C2=CC=CC=C21)CCCC)C(=O)C(C=1)=CC=CC=1C1=CC=C(OC)C(F)=C1 RVWZOMHNKOGKDD-XMMPIXPASA-N 0.000 claims description 2
- ALYLWRDCSITXNL-HXUWFJFHSA-N n-[(2r)-1-(1-ethylindol-3-yl)-3-hydroxypropan-2-yl]-2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxamide Chemical compound N([C@@H](CO)CC1=CN(C2=CC=CC=C21)CC)C(=O)C(C1=CC(OC)=CC=C1N=1)=NC=1C1=CC=C(OC)C(F)=C1 ALYLWRDCSITXNL-HXUWFJFHSA-N 0.000 claims description 2
- BNTXBJWAPPLIBJ-JOCHJYFZSA-N n-[(2r)-1-(1-ethylindol-3-yl)-3-hydroxypropan-2-yl]-3-(3-fluoro-4-methoxyphenyl)benzamide Chemical compound N([C@@H](CO)CC1=CN(C2=CC=CC=C21)CC)C(=O)C(C=1)=CC=CC=1C1=CC=C(OC)C(F)=C1 BNTXBJWAPPLIBJ-JOCHJYFZSA-N 0.000 claims description 2
- CYYAMCSZFHNFDP-JOCHJYFZSA-N n-[(2r)-1-(1-ethylindol-3-yl)-3-hydroxypropan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound N([C@@H](CO)CC1=CN(C2=CC=CC=C21)CC)C(=O)C(C1=CC(OC)=CC=C1N=1)=CC=1C1=CC(OC)=C(OC)C(OC)=C1 CYYAMCSZFHNFDP-JOCHJYFZSA-N 0.000 claims description 2
- DWWKMSBZAOUJIY-HXUWFJFHSA-N n-[(2r)-1-(6-chloro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=C(Cl)C=C3NC=2)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 DWWKMSBZAOUJIY-HXUWFJFHSA-N 0.000 claims description 2
- PBUGGYXRKXDZPG-XMMPIXPASA-N n-[(2r)-1-[1-(3-cyanopropyl)indol-3-yl]-3-hydroxypropan-2-yl]-3-(3-fluoro-4-methoxyphenyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(CCCC#N)C=2)=C1 PBUGGYXRKXDZPG-XMMPIXPASA-N 0.000 claims description 2
- VTBRWWZLAPKRGF-RUZDIDTESA-N n-[(2r)-1-[1-(4-cyanobutyl)indol-3-yl]-3-hydroxypropan-2-yl]-3-(3-fluoro-4-methoxyphenyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(CCCCC#N)C=2)=C1 VTBRWWZLAPKRGF-RUZDIDTESA-N 0.000 claims description 2
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- RJYICORQSYVIEF-OAQYLSRUSA-N n-[(2r)-1-hydroxy-3-(1-methylindol-3-yl)propan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(C)C=2)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 RJYICORQSYVIEF-OAQYLSRUSA-N 0.000 claims description 2
- XUXDGTPDBHYORH-JOCHJYFZSA-N n-[(2r)-1-hydroxy-3-(1-propan-2-ylindol-3-yl)propan-2-yl]-2-(7-methoxy-1-benzofuran-2-yl)-6-(trifluoromethoxy)quinoline-4-carboxamide Chemical compound C1=C(OC(F)(F)F)C=CC2=NC(C3=CC=4C=CC=C(C=4O3)OC)=CC(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4N(C(C)C)C=3)=C21 XUXDGTPDBHYORH-JOCHJYFZSA-N 0.000 claims description 2
- DPXUBGUKOCEBMI-HSZRJFAPSA-N n-[(2r)-1-hydroxy-3-(1-propan-2-ylindol-3-yl)propan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(C(C)C)C=2)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 DPXUBGUKOCEBMI-HSZRJFAPSA-N 0.000 claims description 2
- INCJCIFJPIOITA-HSZRJFAPSA-N n-[(2r)-1-hydroxy-3-(1-propan-2-ylindol-3-yl)propan-2-yl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=CC=CC(C=2N=C3C=CC(OC)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4N(C(C)C)C=3)C=2)=C1 INCJCIFJPIOITA-HSZRJFAPSA-N 0.000 claims description 2
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- QBVZYAABVWJAEN-GOSISDBHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(2,3,4-trimethoxyphenyl)benzamide Chemical compound COC1=C(OC)C(OC)=CC=C1C1=CC=CC=C1C(=O)N[C@@H](CO)CC1=CNC2=CC=CC=C12 QBVZYAABVWJAEN-GOSISDBHSA-N 0.000 claims description 2
- XCWGRFNMQCALDA-MRXNPFEDSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trifluorophenyl)benzamide Chemical compound N([C@H](CC=1C2=CC=CC=C2NC=1)CO)C(=O)C1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 XCWGRFNMQCALDA-MRXNPFEDSA-N 0.000 claims description 2
- HESNCOYZUBEXHW-MRXNPFEDSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2SC=C(N=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 HESNCOYZUBEXHW-MRXNPFEDSA-N 0.000 claims description 2
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- SGUSHPZPMPOUMJ-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 SGUSHPZPMPOUMJ-HXUWFJFHSA-N 0.000 claims description 2
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- JWTMELDPIANIMH-XMMPIXPASA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3-methylbut-2-enoxy)-5-(3,4,5-trimethoxyphenyl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(C(OCC=C(C)C)=CC=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 JWTMELDPIANIMH-XMMPIXPASA-N 0.000 claims description 2
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- ULZVPOZPMMUMGP-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(4-methoxyphenyl)quinazoline-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C(C=CC=C2)C2=N1 ULZVPOZPMMUMGP-LJQANCHMSA-N 0.000 claims description 2
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- AHZSDEXUVYARMT-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(7-methoxy-1-benzofuran-2-yl)-6-(trifluoromethoxy)quinoline-4-carboxamide Chemical compound C1=C(OC(F)(F)F)C=CC2=NC(C3=CC=4C=CC=C(C=4O3)OC)=CC(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)=C21 AHZSDEXUVYARMT-LJQANCHMSA-N 0.000 claims description 2
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- RQYPECHEATXZAN-JOCHJYFZSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-propan-2-yloxy-5-(3,4,5-trimethoxyphenyl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(C(OC(C)C)=CC=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 RQYPECHEATXZAN-JOCHJYFZSA-N 0.000 claims description 2
- IEGJQWLTGVVKGK-JOCHJYFZSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-propoxy-5-(3,4,5-trimethoxyphenyl)benzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC(OC)=C(OC)C(OC)=C1 IEGJQWLTGVVKGK-JOCHJYFZSA-N 0.000 claims description 2
- CDBINYKPTCHARV-JOCHJYFZSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-propoxy-5-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(C(F)(F)F)=C1 CDBINYKPTCHARV-JOCHJYFZSA-N 0.000 claims description 2
- JJZKNGOWFUCABU-JOCHJYFZSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-propoxy-5-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(C(F)(F)F)C=C1 JJZKNGOWFUCABU-JOCHJYFZSA-N 0.000 claims description 2
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- WXBPQULRFRPPFP-XMMPIXPASA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-(3-methoxyprop-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C2=CC(C#CCOC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 WXBPQULRFRPPFP-XMMPIXPASA-N 0.000 claims description 2
- DBHPHNCUNMXKAO-QGZVFWFLSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-(4-methoxyphenyl)pyrimidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=NC=N1 DBHPHNCUNMXKAO-QGZVFWFLSA-N 0.000 claims description 2
- PGXVDTOEJVEUEH-RUZDIDTESA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-(5-hydroxypent-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)C#CCCCO)=C1 PGXVDTOEJVEUEH-RUZDIDTESA-N 0.000 claims description 2
- XSCFFDKKBLSGKM-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(I)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 XSCFFDKKBLSGKM-HXUWFJFHSA-N 0.000 claims description 2
- XYYVXZWRSCSSPP-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(2,3,4-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C2=CC(OC)=CC=C2N=C1C1=CC=C(OC)C(OC)=C1OC XYYVXZWRSCSSPP-LJQANCHMSA-N 0.000 claims description 2
- MPZDWIZVHKMISH-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 MPZDWIZVHKMISH-HXUWFJFHSA-N 0.000 claims description 2
- DTGQIXYBJCBUFL-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(4-methoxy-1-benzofuran-2-yl)quinoline-4-carboxamide Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(C(=O)N[C@@H](CO)CC=4C5=CC=CC=C5NC=4)=C3)OC)=CC2=C1OC DTGQIXYBJCBUFL-LJQANCHMSA-N 0.000 claims description 2
- SZSIPUOOVITXBZ-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(5-methoxy-1-benzofuran-2-yl)quinoline-4-carboxamide Chemical compound C1=C(OC)C=CC2=NC(C=3OC4=CC=C(C=C4C=3)OC)=CC(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)=C21 SZSIPUOOVITXBZ-HXUWFJFHSA-N 0.000 claims description 2
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- VNXKJCJINUQBLZ-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(6-methoxy-1-benzofuran-2-yl)quinoline-4-carboxamide Chemical compound C1=C(OC)C=CC2=NC(C3=CC4=CC=C(C=C4O3)OC)=CC(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)=C21 VNXKJCJINUQBLZ-HXUWFJFHSA-N 0.000 claims description 2
- WIIJMLHMTHBPJX-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(7-methoxy-1-benzofuran-2-yl)quinoline-4-carboxamide Chemical compound C1=CC(OC)=C2OC(C3=NC4=CC=C(C=C4C(C(=O)N[C@@H](CO)CC=4C5=CC=CC=C5NC=4)=C3)OC)=CC2=C1 WIIJMLHMTHBPJX-HXUWFJFHSA-N 0.000 claims description 2
- XBZNUNHECZLCAW-OAQYLSRUSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(7-methyl-1-benzofuran-2-yl)quinoline-4-carboxamide Chemical compound C1=CC(C)=C2OC(C3=NC4=CC=C(C=C4C(C(=O)N[C@@H](CO)CC=4C5=CC=CC=C5NC=4)=C3)OC)=CC2=C1 XBZNUNHECZLCAW-OAQYLSRUSA-N 0.000 claims description 2
- HESKJJLLIZVDEV-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methoxy-2-[5-(trifluoromethoxy)-1-benzofuran-2-yl]quinoline-4-carboxamide Chemical compound FC(F)(F)OC1=CC=C2OC(C3=NC4=CC=C(C=C4C(C(=O)N[C@@H](CO)CC=4C5=CC=CC=C5NC=4)=C3)OC)=CC2=C1 HESKJJLLIZVDEV-LJQANCHMSA-N 0.000 claims description 2
- ROCXXBXRSMUWMT-OAQYLSRUSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-methyl-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(C)=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 ROCXXBXRSMUWMT-OAQYLSRUSA-N 0.000 claims description 2
- OTYDRQVYQLEWLB-LJQANCHMSA-N n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-6-nitro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC(=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)[N+]([O-])=O)=C1 OTYDRQVYQLEWLB-LJQANCHMSA-N 0.000 claims description 2
- BVTFXTGWFGNVJM-HXUWFJFHSA-N n-[(2r)-1-hydroxy-3-(2-methyl-1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2C)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 BVTFXTGWFGNVJM-HXUWFJFHSA-N 0.000 claims description 2
- BLQLKKUCXBFTQQ-GDLZYMKVSA-N n-[(2r)-3-hydroxy-1-(1h-indol-3-yl)-3-methylbutan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC=CC3=C(C(=O)N[C@H](CC=3C4=CC=CC=C4NC=3)C(C)(C)O)C=2)=C1 BLQLKKUCXBFTQQ-GDLZYMKVSA-N 0.000 claims description 2
- PBBQGKZLEDVDNQ-SSEXGKCCSA-N n-[(2r)-3-hydroxy-1-(1h-indol-3-yl)-3-methylbutan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(C)(C)O)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 PBBQGKZLEDVDNQ-SSEXGKCCSA-N 0.000 claims description 2
- SGUSHPZPMPOUMJ-FQEVSTJZSA-N n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC=CC3=C(C(=O)N[C@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 SGUSHPZPMPOUMJ-FQEVSTJZSA-N 0.000 claims description 2
- WJPZEXKUMLLHOY-UHFFFAOYSA-N n-[1-(1-ethyl-5-fluoroindol-3-yl)-3-hydroxypropan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C12=CC(F)=CC=C2N(CC)C=C1CC(CO)NC(=O)C(C1=CC(OC)=CC=C1N=1)=CC=1C1=CC(OC)=C(OC)C(OC)=C1 WJPZEXKUMLLHOY-UHFFFAOYSA-N 0.000 claims description 2
- XXBONWAGQRQBID-UHFFFAOYSA-N n-[1-(5,6-difluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-ethoxy-5-(3-methoxyphenyl)benzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=C(F)C=C3NC=2)C(OCC)=CC=C1C1=CC=CC(OC)=C1 XXBONWAGQRQBID-UHFFFAOYSA-N 0.000 claims description 2
- DNAIXYZUFJOQHK-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxy-5-(3-propoxyphenyl)benzamide Chemical compound CCCOC1=CC=CC(C=2C=C(C(OCCC)=CC=2)C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)=C1 DNAIXYZUFJOQHK-UHFFFAOYSA-N 0.000 claims description 2
- RRGCIGSFLVZGGO-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxy-5-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(C(F)(F)F)=C1 RRGCIGSFLVZGGO-UHFFFAOYSA-N 0.000 claims description 2
- SHWQYYOOOCGBLZ-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxy-5-pyridin-3-ylbenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CN=C1 SHWQYYOOOCGBLZ-UHFFFAOYSA-N 0.000 claims description 2
- ZHJCACIOFIGNJD-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxy-5-quinolin-3-ylbenzamide Chemical compound C1=CC=CC2=CC(C3=CC=C(C(=C3)C(=O)NC(CO)CC=3C4=CC(F)=CC=C4NC=3)OCCC)=CN=C21 ZHJCACIOFIGNJD-UHFFFAOYSA-N 0.000 claims description 2
- JIWLUUVOBJIEDQ-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-2-propoxy-5-quinolin-6-ylbenzamide Chemical compound N1=CC=CC2=CC(C3=CC=C(C(=C3)C(=O)NC(CO)CC=3C4=CC(F)=CC=C4NC=3)OCCC)=CC=C21 JIWLUUVOBJIEDQ-UHFFFAOYSA-N 0.000 claims description 2
- BOWFJHVJVVQLEE-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-(3-methylsulfanylphenyl)-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(SC)=C1 BOWFJHVJVVQLEE-UHFFFAOYSA-N 0.000 claims description 2
- HFWRUMHWNGHXBE-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-(3-methylsulfonylphenyl)-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 HFWRUMHWNGHXBE-UHFFFAOYSA-N 0.000 claims description 2
- CJUPZRMSLIHPRT-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-(3-propan-2-ylphenyl)-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(C(C)C)=C1 CJUPZRMSLIHPRT-UHFFFAOYSA-N 0.000 claims description 2
- XQASTFYXHYMKCV-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-(4-propan-2-ylsulfonylphenyl)-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(S(=O)(=O)C(C)C)C=C1 XQASTFYXHYMKCV-UHFFFAOYSA-N 0.000 claims description 2
- PGZDESQBNUQEQR-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-(6-fluoro-5-methylpyridin-3-yl)-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CN=C(F)C(C)=C1 PGZDESQBNUQEQR-UHFFFAOYSA-N 0.000 claims description 2
- SPBBCBHWGSUXOT-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-(6-methoxypyridin-3-yl)-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=C(OC)N=C1 SPBBCBHWGSUXOT-UHFFFAOYSA-N 0.000 claims description 2
- KHXQUTSUPXNRLM-ONEGZZNKSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-[(e)-2-(4-fluorophenyl)ethenyl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1\C=C\C1=CC=C(F)C=C1 KHXQUTSUPXNRLM-ONEGZZNKSA-N 0.000 claims description 2
- KZUFRWQMUSXYFK-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-[3-(hydroxymethyl)phenyl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(CO)=C1 KZUFRWQMUSXYFK-UHFFFAOYSA-N 0.000 claims description 2
- SJFAGUJRGGINSX-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-[3-(methanesulfonamido)phenyl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(NS(C)(=O)=O)=C1 SJFAGUJRGGINSX-UHFFFAOYSA-N 0.000 claims description 2
- OFOMQYXOHOSJQY-UHFFFAOYSA-N n-[1-(5-fluoro-1h-indol-3-yl)-3-hydroxypropan-2-yl]-5-[3-(methylsulfamoyl)phenyl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC(F)=CC=C3NC=2)C(OCCC)=CC=C1C1=CC=CC(S(=O)(=O)NC)=C1 OFOMQYXOHOSJQY-UHFFFAOYSA-N 0.000 claims description 2
- KTJCABHGHSAEAS-UHFFFAOYSA-N n-[1-hydroxy-3-(6-methyl-1h-indol-3-yl)propan-2-yl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide Chemical compound C1=C(C(=O)NC(CO)CC=2C3=CC=C(C)C=C3NC=2)C2=CC(OC)=CC=C2N=C1C1=CC(OC)=C(OC)C(OC)=C1 KTJCABHGHSAEAS-UHFFFAOYSA-N 0.000 claims description 2
- IWRBYSYRCVKCOI-MUUNZHRXSA-N tert-butyl n-butyl-n-[3-[3-[[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]carbamoyl]-4-propoxyphenyl]phenyl]carbamate Chemical compound CCCCN(C(=O)OC(C)(C)C)C1=CC=CC(C=2C=C(C(OCCC)=CC=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 IWRBYSYRCVKCOI-MUUNZHRXSA-N 0.000 claims description 2
- ABZVZAZGAFPDOO-HHHXNRCGSA-N tert-butyl n-butyl-n-[3-[4-ethoxy-3-[[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]carbamoyl]phenyl]phenyl]carbamate Chemical compound CCCCN(C(=O)OC(C)(C)C)C1=CC=CC(C=2C=C(C(OCC)=CC=2)C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C1 ABZVZAZGAFPDOO-HHHXNRCGSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- FNQLBIDFHVGJEG-UHFFFAOYSA-N 2-propoxy-5-[3-(2,2,2-trifluoroethoxy)phenyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=CC(OCC(F)(F)F)=C1 FNQLBIDFHVGJEG-UHFFFAOYSA-N 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- ABVXWURYEFNCII-HXUWFJFHSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound O1CCOC2=CC(C=3C=C(C4=CC=CC=C4N=3)C(=O)N[C@H](CC=3C4=CC=CC=C4NC=3)CO)=CC=C21 ABVXWURYEFNCII-HXUWFJFHSA-N 0.000 claims 1
- CZCCWANSDBVVHB-OAQYLSRUSA-N 2-(2,3-dihydro-1-benzofuran-5-yl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound C1=C2OCCC2=CC(C=2C=C(C3=CC=CC=C3N=2)C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)CO)=C1 CZCCWANSDBVVHB-OAQYLSRUSA-N 0.000 claims 1
- AVABRJACYGCGHW-JOCHJYFZSA-N 2-(3,4-dimethylphenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound C1=C(C)C(C)=CC=C1C1=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3NC=2)=C(C=CC=C2)C2=N1 AVABRJACYGCGHW-JOCHJYFZSA-N 0.000 claims 1
- IPLVVKSDLXGTDQ-JOCHJYFZSA-N 2-(3-acetamidophenyl)-n-[(2r)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]quinoline-4-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2N=C3C=CC=CC3=C(C(=O)N[C@@H](CO)CC=3C4=CC=CC=C4NC=3)C=2)=C1 IPLVVKSDLXGTDQ-JOCHJYFZSA-N 0.000 claims 1
- INRUCUXYOLKMIF-PPRAREMJSA-N 2-(3-cyanopropoxy)-N-[(1R)-1-hydroxy-2-(1H-indol-3-yl)propyl]-5-(3,4,5-trimethoxyphenyl)benzamide Chemical compound O[C@H](C(C1=CNC2=CC=CC=C12)C)NC(=O)C=1C=C(C=CC1OCCCC#N)C1=CC(=C(C(=C1)OC)OC)OC INRUCUXYOLKMIF-PPRAREMJSA-N 0.000 claims 1
- VVGKNOCHVZNGJE-OAQYLSRUSA-N 2-(3-fluoro-4-methoxyphenyl)-n-[(2r)-1-hydroxy-3-(1-propan-2-ylindol-3-yl)propan-2-yl]-6-(trifluoromethoxy)quinoline-4-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(=O)N[C@@H](CO)CC=2C3=CC=CC=C3N(C(C)C)C=2)=C(C=C(OC(F)(F)F)C=C2)C2=N1 VVGKNOCHVZNGJE-OAQYLSRUSA-N 0.000 claims 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical class N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- 230000001646 thyrotropic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229940100640 transdermal system Drugs 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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 1
- 238000002255 vaccination Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P15/18—Feminine contraceptives
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- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70674305P | 2005-08-10 | 2005-08-10 | |
| DE102005038632.6 | 2005-08-10 | ||
| DE102005038632A DE102005038632B4 (de) | 2005-08-10 | 2005-08-10 | Acyltryptophanole |
| US60/706,743 | 2005-08-10 | ||
| PCT/EP2006/007949 WO2007017289A2 (fr) | 2005-08-10 | 2006-08-08 | Acyltryptophanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2618888A1 true CA2618888A1 (fr) | 2007-02-15 |
Family
ID=37116073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002618888A Abandoned CA2618888A1 (fr) | 2005-08-10 | 2006-08-08 | Acyltryptophanols |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1912970A2 (fr) |
| JP (1) | JP2009504597A (fr) |
| CA (1) | CA2618888A1 (fr) |
| WO (1) | WO2007017289A2 (fr) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7504401B2 (en) | 2003-08-29 | 2009-03-17 | Locus Pharmaceuticals, Inc. | Anti-cancer agents and uses thereof |
| TW200806290A (en) * | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted biaryl compounds for inflammation and immune-related uses |
| CA2669104A1 (fr) * | 2006-11-21 | 2008-05-29 | University Of Virginia Patent Foundation | Analogues d'hydrindane ayant une activite agoniste de recepteur de sphingosine-1-phosphate |
| US20080221195A1 (en) * | 2006-12-13 | 2008-09-11 | Lars Wortmann | 1,2-diarylacetylene derivatives of acyltryptophanols |
| EP1956016A1 (fr) * | 2006-12-15 | 2008-08-13 | Bayer Schering Pharma Aktiengesellschaft | Acyltryptophanols |
| WO2008071455A1 (fr) * | 2006-12-15 | 2008-06-19 | Bayer Schering Pharma Aktiengesellschaft | Acyltryptophanols bicycliques |
| EP1964834A1 (fr) * | 2007-03-01 | 2008-09-03 | Bayer Schering Pharma Aktiengesellschaft | Sulphonyltryptophanols |
| GB0705656D0 (en) * | 2007-03-23 | 2007-05-02 | Addex Pharmaceuticals Sa | Novel compounds E1 |
| EP1975159A1 (fr) * | 2007-03-27 | 2008-10-01 | Bayer Schering Pharma Aktiengesellschaft | 2,3,4,9-Tetrahydro-1H-carbazoles |
| EP1985612A1 (fr) * | 2007-04-26 | 2008-10-29 | Bayer Schering Pharma Aktiengesellschaft | N-Acyl-gamma-amino-alcools substitués d'aryméthylène |
| EP2019102A1 (fr) * | 2007-07-24 | 2009-01-28 | Bayer Schering Pharma AG | Acyltryptophanols à alkylacétylène substitué |
| EP2018859A1 (fr) * | 2007-07-26 | 2009-01-28 | Bayer Schering Pharma Aktiengesellschaft | N-acyl-bêta-amino alcools à arylméthylène substitué |
| EP2020404A1 (fr) * | 2007-08-01 | 2009-02-04 | Bayer Schering Pharma Aktiengesellschaft | N-Acyl Tryptamines à substitution cyanométhyle |
| EP2025669A1 (fr) * | 2007-08-14 | 2009-02-18 | Bayer Schering Pharma Aktiengesellschaft | N-acyltryptophanols à substitution alpha-alkyle |
| JP5693452B2 (ja) | 2008-08-04 | 2015-04-01 | シーエイチディーアイ ファウンデーション,インコーポレーテッド | 特定のキヌレニン−3−モノオキシゲナーゼインヒビター、医薬組成物およびそれらの使用方法 |
| MX2011004570A (es) * | 2008-10-31 | 2011-06-17 | Merck Sharp & Dohme | Antagonistas del receptor p2x3 para el tratamiento del dolor. |
| CA2787365A1 (fr) | 2010-01-25 | 2011-07-28 | Chdi Foundation, Inc. | Certains inhibiteurs de kynurenine-3-monooxygenase, compositions pharmaceutiques, et procedes d'utilisation de ceux-ci |
| US20120174381A1 (en) | 2011-01-10 | 2012-07-12 | David Messick | Apparatus and method for frame crimping |
| CN103562379A (zh) * | 2011-05-19 | 2014-02-05 | 国立大学法人德岛大学 | 细胞分化诱导剂以及分化诱导方法 |
| KR20140072037A (ko) | 2011-08-30 | 2014-06-12 | 씨에이치디아이 파운데이션, 인코포레이티드 | 키뉴레닌-3-모노옥시게나제 억제제, 약학적 조성물 및 이의 사용 방법 |
| SI2750677T1 (sl) | 2011-08-30 | 2017-10-30 | Chdi Foundation, Inc. | Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe |
| ES2585653T3 (es) | 2011-09-22 | 2016-10-07 | Merck Sharp & Dohme B.V. | Antagonistas del receptor de FSH |
| EP2763986B1 (fr) * | 2011-09-22 | 2017-06-07 | Merck Sharp & Dohme B.V. | Antagonistes du récepteur de la fsh |
| AU2015289492B2 (en) | 2014-07-17 | 2020-02-20 | Chdi Foundation, Inc. | Methods and compositions for treating HIV-related disorders |
| BR112017013465A2 (pt) * | 2014-12-24 | 2018-03-06 | Lg Chem, Ltd | derivado de biarila, e, composição farmacêutica. |
| CN119241381A (zh) | 2019-12-26 | 2025-01-03 | 吉尔伽美什制药公司 | 芳基环己基胺衍生物及其在精神障碍的治疗中的用途 |
| KR20260008838A (ko) | 2020-02-18 | 2026-01-16 | 길가메쉬 파마슈티컬스, 인코포레이티드 | 기분 장애 치료에 사용되기 위한 특이적 트립타민 |
| CN111606774A (zh) * | 2020-07-01 | 2020-09-01 | 云南民族大学 | 一种高效制备苯乙烯类及氘代苯乙烯类化合物的方法 |
| US12331020B2 (en) | 2020-12-31 | 2025-06-17 | 1280225 B.C. Ltd. | Method of synthesizing indole compounds |
| US12180158B1 (en) | 2023-08-03 | 2024-12-31 | Gilgamesh Pharmaceuticals, Inc. | Crystalline fumarate salts of n-ethyl-2-(5-fluoro-1H-indol-3-yl)-n-methylethan-1-amine |
| US12129234B1 (en) | 2023-08-03 | 2024-10-29 | Gilgamesh Pharmaceuticals, Inc. | Crystalline salts of N-ethyl-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000058277A1 (fr) * | 1999-03-31 | 2000-10-05 | American Home Products Corporation | Acides sulfoniques aryles et derives tels que les antagonistes fsh |
| AU3714100A (en) * | 1999-03-31 | 2000-10-16 | American Home Products Corporation | 7-amino-4-hydroxy-3-(4-methoxy-phenylazo)-naphthalene-2-sulf onic acid derivatives as fsh antagonists |
| ATE277913T1 (de) * | 2001-01-19 | 2004-10-15 | Pharmacopeia Inc | Bisarylderivate mit fsh rezeptor modulierender aktivität |
| CZ20042A3 (en) * | 2001-07-02 | 2004-04-14 | Akzo Nobel N. V. | Tetrahydroquinoline derivatives |
| BRPI0408365B8 (pt) * | 2003-03-14 | 2021-05-25 | Avidex Ltd | compostos heterocíclicos de imunomodulação |
-
2006
- 2006-08-08 CA CA002618888A patent/CA2618888A1/fr not_active Abandoned
- 2006-08-08 JP JP2008525491A patent/JP2009504597A/ja active Pending
- 2006-08-08 WO PCT/EP2006/007949 patent/WO2007017289A2/fr not_active Ceased
- 2006-08-08 EP EP06776768A patent/EP1912970A2/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007017289A2 (fr) | 2007-02-15 |
| JP2009504597A (ja) | 2009-02-05 |
| EP1912970A2 (fr) | 2008-04-23 |
| WO2007017289A3 (fr) | 2007-05-31 |
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