JP2018520096A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018520096A5 JP2018520096A5 JP2017559303A JP2017559303A JP2018520096A5 JP 2018520096 A5 JP2018520096 A5 JP 2018520096A5 JP 2017559303 A JP2017559303 A JP 2017559303A JP 2017559303 A JP2017559303 A JP 2017559303A JP 2018520096 A5 JP2018520096 A5 JP 2018520096A5
- Authority
- JP
- Japan
- Prior art keywords
- indol
- benzoic acid
- phenylethynyl
- ethynyl
- ylmethyl
- 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.)
- Granted
Links
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 101150059079 EBNA1 gene Proteins 0.000 claims description 7
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 206010025323 Lymphomas Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- MYWYYAAUMMNIOG-UHFFFAOYSA-N 3-[2-[4-[(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)carbamoyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC=1SC2=C(N=1)CCC(C2)NC(=O)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 MYWYYAAUMMNIOG-UHFFFAOYSA-N 0.000 claims description 3
- JEEHRIGAEVQDCF-UHFFFAOYSA-N 3-[2-[4-[[(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)amino]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC=1SC2=C(N=1)CCC(C2)NCC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 JEEHRIGAEVQDCF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
- 206010002412 Angiocentric lymphomas Diseases 0.000 claims description 3
- 206010015108 Epstein-Barr virus infection Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 206010002449 angioimmunoblastic T-cell lymphoma Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 238000007918 intramuscular administration Methods 0.000 claims description 3
- 238000007913 intrathecal administration Methods 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 238000007920 subcutaneous administration Methods 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- HHDMHECJXMFMBX-UHFFFAOYSA-N 2-(1H-indazol-6-yl)-3-[2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1N=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)S(=O)(=O)C HHDMHECJXMFMBX-UHFFFAOYSA-N 0.000 claims description 2
- RVCNLOKYKLEMPX-UHFFFAOYSA-N 2-(1H-indol-5-yl)-3-[2-[4-[(4-methoxypiperidin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC(=CC=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCC(CC1)OC RVCNLOKYKLEMPX-UHFFFAOYSA-N 0.000 claims description 2
- SQOSJFNLUXNXQC-UHFFFAOYSA-N 2-(1H-indol-5-yl)-3-[2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC(=CC=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)C SQOSJFNLUXNXQC-UHFFFAOYSA-N 0.000 claims description 2
- LYZWSYAINGBGQI-UHFFFAOYSA-N 2-(1H-indol-5-yl)-3-[2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC(=CC=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)S(=O)(=O)C LYZWSYAINGBGQI-UHFFFAOYSA-N 0.000 claims description 2
- SKMHFEWRYJMQAT-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)S(=O)(=O)C SKMHFEWRYJMQAT-UHFFFAOYSA-N 0.000 claims description 2
- OPJBJDBCKLUSAZ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-7-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)S(=O)(=O)C OPJBJDBCKLUSAZ-UHFFFAOYSA-N 0.000 claims description 2
- UMSGIJSSVASIBX-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-propan-2-ylsulfonyl-1,3-dihydroisoindol-5-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CN(CC2=CC=1)S(=O)(=O)C(C)C UMSGIJSSVASIBX-UHFFFAOYSA-N 0.000 claims description 2
- WLQKJZZVNXMDMB-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-propan-2-ylsulfonyl-3,4-dihydro-1H-isoquinolin-6-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)S(=O)(=O)C(C)C WLQKJZZVNXMDMB-UHFFFAOYSA-N 0.000 claims description 2
- LGPAIUMTKPAZNA-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-propan-2-ylsulfonyl-3,4-dihydro-1H-isoquinolin-7-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)S(=O)(=O)C(C)C LGPAIUMTKPAZNA-UHFFFAOYSA-N 0.000 claims description 2
- AWPRYKLDTKDLGI-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-propanoyl-3,4-dihydro-1H-isoquinolin-6-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)C(CC)=O AWPRYKLDTKDLGI-UHFFFAOYSA-N 0.000 claims description 2
- COMIPLCOFHUAEI-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(2-propanoyl-3,4-dihydro-1H-isoquinolin-7-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)C(CC)=O COMIPLCOFHUAEI-UHFFFAOYSA-N 0.000 claims description 2
- FGONZUHFKCKVNN-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=NC=2NCCCC=2C=1 FGONZUHFKCKVNN-UHFFFAOYSA-N 0.000 claims description 2
- NGFLLLPSSNUFSW-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(2-morpholin-4-ylethyl)indol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C=CN(C2=CC=1)CCN1CCOCC1 NGFLLLPSSNUFSW-UHFFFAOYSA-N 0.000 claims description 2
- MAERRVATLNTPKP-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(2-morpholin-4-ylethyl)indol-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2C=CN(C2=C1)CCN1CCOCC1 MAERRVATLNTPKP-UHFFFAOYSA-N 0.000 claims description 2
- FHIMDFIGVVVTAS-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(2-morpholin-4-ylethyl)pyrrolo[2,3-b]pyridin-3-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CN(C2=NC=CC=C21)CCN1CCOCC1 FHIMDFIGVVVTAS-UHFFFAOYSA-N 0.000 claims description 2
- CDRBVBXEHNUWLN-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(2-morpholin-4-ylethyl)pyrrolo[2,3-b]pyridin-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C(=NC=1)N(C=C2)CCN1CCOCC1 CDRBVBXEHNUWLN-UHFFFAOYSA-N 0.000 claims description 2
- CLSOANBDFMDBQE-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(3-morpholin-4-ylpropyl)indol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C=CN(C2=CC=1)CCCN1CCOCC1 CLSOANBDFMDBQE-UHFFFAOYSA-N 0.000 claims description 2
- CDLXQLQDCNIHAU-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(3-morpholin-4-ylpropyl)indol-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2C=CN(C2=C1)CCCN1CCOCC1 CDLXQLQDCNIHAU-UHFFFAOYSA-N 0.000 claims description 2
- CJOVXOLRFGWYNV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(3-morpholin-4-ylpropyl)pyrrolo[2,3-b]pyridin-3-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CN(C2=NC=CC=C21)CCCN1CCOCC1 CJOVXOLRFGWYNV-UHFFFAOYSA-N 0.000 claims description 2
- NCWVDKVBVDXCKG-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(3-morpholin-4-ylpropyl)pyrrolo[2,3-b]pyridin-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C(=NC=1)N(C=C2)CCCN1CCOCC1 NCWVDKVBVDXCKG-UHFFFAOYSA-N 0.000 claims description 2
- GIECNKDRPYERMN-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(oxan-4-ylmethyl)indol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C=CN(C2=CC=1)CC1CCOCC1 GIECNKDRPYERMN-UHFFFAOYSA-N 0.000 claims description 2
- BQITWTGJAMPXRP-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-(oxan-4-ylmethyl)pyrrolo[2,3-b]pyridin-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C(=NC=1)N(C=C2)CC1CCOCC1 BQITWTGJAMPXRP-UHFFFAOYSA-N 0.000 claims description 2
- MOPSBALTZLPPBC-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-[(1-methylsulfonylpiperidin-4-yl)methyl]indol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C=CN(C2=CC=1)CC1CCN(CC1)S(=O)(=O)C MOPSBALTZLPPBC-UHFFFAOYSA-N 0.000 claims description 2
- BGYUOQDFWKYVOL-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[1-[(1-methylsulfonylpiperidin-4-yl)methyl]pyrrolo[2,3-b]pyridin-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2C(=NC=1)N(C=C2)CC1CCN(CC1)S(=O)(=O)C BGYUOQDFWKYVOL-UHFFFAOYSA-N 0.000 claims description 2
- JQWCIJDPAMHEBY-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-(1-methylsulfonylazetidin-3-yl)-1,3-dihydroisoindol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CN(CC2=CC=1)C1CN(C1)S(=O)(=O)C JQWCIJDPAMHEBY-UHFFFAOYSA-N 0.000 claims description 2
- OIPPWJPLJSQUKP-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-(1-methylsulfonylazetidin-3-yl)-3,4-dihydro-1H-isoquinolin-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)C1CN(C1)S(=O)(=O)C OIPPWJPLJSQUKP-UHFFFAOYSA-N 0.000 claims description 2
- PFNXQRKTORGYMC-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-(1-methylsulfonylpyrrolidin-3-yl)-1,3-dihydroisoindol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CN(CC2=CC=1)C1CN(CC1)S(=O)(=O)C PFNXQRKTORGYMC-UHFFFAOYSA-N 0.000 claims description 2
- JNIZOGSCXXBIOR-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-(1-methylsulfonylpyrrolidin-3-yl)-3,4-dihydro-1H-isoquinolin-7-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)C1CN(CC1)S(=O)(=O)C JNIZOGSCXXBIOR-UHFFFAOYSA-N 0.000 claims description 2
- RDCJXIRUSHVNTR-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-(morpholin-4-ylmethyl)-1H-indol-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2C=C(NC2=C1)CN1CCOCC1 RDCJXIRUSHVNTR-UHFFFAOYSA-N 0.000 claims description 2
- UZCBOSBMRRUQSQ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-(propylcarbamoyl)-1H-indol-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2C=C(NC2=C1)C(NCCC)=O UZCBOSBMRRUQSQ-UHFFFAOYSA-N 0.000 claims description 2
- VSQIMJALGACDOF-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylazetidin-3-yl)methyl]-1,3-dihydroisoindol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CN(CC2=CC=1)CC1CN(C1)S(=O)(=O)C VSQIMJALGACDOF-UHFFFAOYSA-N 0.000 claims description 2
- WIHLUWNCNZKPLV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylazetidin-3-yl)methyl]-3,4-dihydro-1H-isoquinolin-7-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)CC1CN(C1)S(=O)(=O)C WIHLUWNCNZKPLV-UHFFFAOYSA-N 0.000 claims description 2
- CAJBHVNXXPNDOW-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylpiperidin-4-yl)methyl]-1,3-dihydroisoindol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CN(CC2=CC=1)CC1CCN(CC1)S(=O)(=O)C CAJBHVNXXPNDOW-UHFFFAOYSA-N 0.000 claims description 2
- MJDOXPKGEBBLME-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylpiperidin-4-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)CC1CCN(CC1)S(=O)(=O)C MJDOXPKGEBBLME-UHFFFAOYSA-N 0.000 claims description 2
- YNAMSFNEAHOXIE-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylpyrrolidin-3-yl)methyl]-1,3-dihydroisoindol-5-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CN(CC2=CC=1)CC1CN(CC1)S(=O)(=O)C YNAMSFNEAHOXIE-UHFFFAOYSA-N 0.000 claims description 2
- CSYVZCYHZGYDDC-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylpyrrolidin-3-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)CC1CN(CC1)S(=O)(=O)C CSYVZCYHZGYDDC-UHFFFAOYSA-N 0.000 claims description 2
- NNJUHRMDLGUJDO-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylpyrrolidin-3-yl)methyl]-3,4-dihydro-1H-isoquinolin-7-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)CC1CN(CC1)S(=O)(=O)C NNJUHRMDLGUJDO-UHFFFAOYSA-N 0.000 claims description 2
- QQVDFVDFDXALJV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(4-methoxypiperidin-1-yl)methyl]-4-oxo-3H-quinazolin-6-yl]ethynyl]benzoic acid Chemical compound COC1CCN(CC1)CC=1NC2=CC=C(C=C2C(N=1)=O)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 QQVDFVDFDXALJV-UHFFFAOYSA-N 0.000 claims description 2
- CXZZTVMSYXBXGB-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[[3-(methanesulfonamido)phenyl]methyl]-3,4-dihydro-1H-isoquinolin-7-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2CCN(CC2=C1)CC1=CC(=CC=C1)NS(=O)(=O)C CXZZTVMSYXBXGB-UHFFFAOYSA-N 0.000 claims description 2
- BWAZVQRHSWJHIV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-(1,3-oxazol-5-yl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=CC=C1)C1=CN=CO1 BWAZVQRHSWJHIV-UHFFFAOYSA-N 0.000 claims description 2
- FUGVGMJSIGIMEH-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-(2-methoxyethyl)-4-oxopyrido[2,3-d]pyrimidin-6-yl]ethynyl]benzoic acid Chemical compound COCCN1C=NC2=C(C1=O)C=C(C=N2)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 FUGVGMJSIGIMEH-UHFFFAOYSA-N 0.000 claims description 2
- OTNDXUPSAOCXGV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-(2H-tetrazol-5-yl)phenyl]ethynyl]benzoic acid Chemical compound N=1NN=NC=1C=1C=C(C=CC=1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 OTNDXUPSAOCXGV-UHFFFAOYSA-N 0.000 claims description 2
- TZIFOSBLTCRQQI-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-(morpholin-4-ylmethyl)-1H-indol-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2C(=CNC2=C1)CN1CCOCC1 TZIFOSBLTCRQQI-UHFFFAOYSA-N 0.000 claims description 2
- WKUJQCZAIBEVMG-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-[(2-methoxy-6-methylphenyl)carbamoyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=CC=C1)C(NC1=C(C=CC=C1C)OC)=O WKUJQCZAIBEVMG-UHFFFAOYSA-N 0.000 claims description 2
- MUWPEDJNEDRHOY-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-[(4-methylsulfonylpiperazin-1-yl)methyl]-1H-indol-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C2C(=CNC2=C1)CN1CCN(CC1)S(=O)(=O)C MUWPEDJNEDRHOY-UHFFFAOYSA-N 0.000 claims description 2
- QTEDZEZOFSDHFH-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-[2-(methanesulfonamido)-1,3-thiazol-4-yl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=CC=C1)C=1N=C(SC=1)NS(=O)(=O)C QTEDZEZOFSDHFH-UHFFFAOYSA-N 0.000 claims description 2
- WVIPJZFBKQHTNQ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-methoxy-4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=C(C=C1)CN1CCOCC1)OC WVIPJZFBKQHTNQ-UHFFFAOYSA-N 0.000 claims description 2
- LMFQQMHFEOQNIZ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-methoxy-4-[(4-morpholin-4-ylpiperidin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=C(C=C1)CN1CCC(CC1)N1CCOCC1)OC LMFQQMHFEOQNIZ-UHFFFAOYSA-N 0.000 claims description 2
- IENFPNNWYNFNDG-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(1,3-oxazol-5-yl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C1=CN=CO1 IENFPNNWYNFNDG-UHFFFAOYSA-N 0.000 claims description 2
- KCCWZINCMQRQLR-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(2H-tetrazol-5-yl)phenyl]ethynyl]benzoic acid Chemical compound N=1NN=NC=1C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 KCCWZINCMQRQLR-UHFFFAOYSA-N 0.000 claims description 2
- ABXSSRGOPBQYRI-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(4-methoxypiperidine-1-carbonyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C(=O)N1CCC(CC1)OC ABXSSRGOPBQYRI-UHFFFAOYSA-N 0.000 claims description 2
- LWNMMVNXWPSQRX-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(4-methylpiperazine-1-carbonyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C(=O)N1CCN(CC1)C LWNMMVNXWPSQRX-UHFFFAOYSA-N 0.000 claims description 2
- JEDZXGGMGLFXME-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(6-oxo-1H-pyridazin-3-yl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C1=NNC(C=C1)=O JEDZXGGMGLFXME-UHFFFAOYSA-N 0.000 claims description 2
- AWAMGASZNAVMOZ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCOCC1 AWAMGASZNAVMOZ-UHFFFAOYSA-N 0.000 claims description 2
- VUJZFNSWCNSGDV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(oxan-4-yloxymethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1CCOCC1 VUJZFNSWCNSGDV-UHFFFAOYSA-N 0.000 claims description 2
- BHSLRKOLNSOXBQ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(oxane-4-carbonyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C(=O)C1CCOCC1 BHSLRKOLNSOXBQ-UHFFFAOYSA-N 0.000 claims description 2
- WCJPRWXITFLSBN-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(phenoxymethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC=CC=C1 WCJPRWXITFLSBN-UHFFFAOYSA-N 0.000 claims description 2
- QGSLXJUZTKKKOT-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(piperazin-1-ylmethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCNCC1 QGSLXJUZTKKKOT-UHFFFAOYSA-N 0.000 claims description 2
- NATAEIYIVLTZTF-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(propan-2-yloxymethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC(C)C NATAEIYIVLTZTF-UHFFFAOYSA-N 0.000 claims description 2
- MTPQHWLOCAQMJW-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(pyridin-3-yloxymethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC=1C=NC=CC=1 MTPQHWLOCAQMJW-UHFFFAOYSA-N 0.000 claims description 2
- RYNRCLJIIHYCEU-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-(pyrimidin-5-yloxymethyl)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC=1C=NC=NC=1 RYNRCLJIIHYCEU-UHFFFAOYSA-N 0.000 claims description 2
- MVMMYUCPTULLDM-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(1-methylsulfonylpiperidin-4-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CC1CCN(CC1)S(=O)(=O)C MVMMYUCPTULLDM-UHFFFAOYSA-N 0.000 claims description 2
- UTVXZSXJVJKDKX-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(1-propan-2-ylsulfonylpiperidin-4-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CC1CCN(CC1)S(=O)(=O)C(C)C UTVXZSXJVJKDKX-UHFFFAOYSA-N 0.000 claims description 2
- NQDAQKIYTJVJJA-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(2-methylsulfonylphenoxy)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=C(C=CC=C1)S(=O)(=O)C NQDAQKIYTJVJJA-UHFFFAOYSA-N 0.000 claims description 2
- AHESMBVFFVAFLF-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(3-methoxyphenoxy)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC(=CC=C1)OC AHESMBVFFVAFLF-UHFFFAOYSA-N 0.000 claims description 2
- VVNLWSVVJJILIX-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(3-methoxypyrrolidin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CC(CC1)OC VVNLWSVVJJILIX-UHFFFAOYSA-N 0.000 claims description 2
- PYDHIJRUSFNKJQ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(3-methylsulfonylphenoxy)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC(=CC=C1)S(=O)(=O)C PYDHIJRUSFNKJQ-UHFFFAOYSA-N 0.000 claims description 2
- YCWCDSLXROLNLL-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-methoxyphenoxy)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC=C(C=C1)OC YCWCDSLXROLNLL-UHFFFAOYSA-N 0.000 claims description 2
- POMUHOPBNCQZPE-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-methoxypiperidin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCC(CC1)OC POMUHOPBNCQZPE-UHFFFAOYSA-N 0.000 claims description 2
- HMSWQKRXTAPZJT-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-methyl-1,4-diazepan-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CCC1)C HMSWQKRXTAPZJT-UHFFFAOYSA-N 0.000 claims description 2
- VPUWPQIICXFYFK-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)C VPUWPQIICXFYFK-UHFFFAOYSA-N 0.000 claims description 2
- AWKHCYOMHNNETO-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-methylsulfonylphenoxy)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC=C(C=C1)S(=O)(=O)C AWKHCYOMHNNETO-UHFFFAOYSA-N 0.000 claims description 2
- IOUPEYQTHGABIK-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)S(=O)(=O)C IOUPEYQTHGABIK-UHFFFAOYSA-N 0.000 claims description 2
- GAUDGJJJFSPNSM-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-oxocyclohexyl)carbamoyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C(NC1CCC(CC1)=O)=O GAUDGJJJFSPNSM-UHFFFAOYSA-N 0.000 claims description 2
- ZNLKVKTVSZDEPE-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)C(C)C ZNLKVKTVSZDEPE-UHFFFAOYSA-N 0.000 claims description 2
- FSCCQPBSFNSTFV-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-propan-2-ylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)S(=O)(=O)C(C)C FSCCQPBSFNSTFV-UHFFFAOYSA-N 0.000 claims description 2
- QWAFWTZVBXWKNT-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-pyrazin-2-ylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)C1=NC=CN=C1 QWAFWTZVBXWKNT-UHFFFAOYSA-N 0.000 claims description 2
- SPYAZKXNUSPUAC-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(4-sulfamoylpiperazin-1-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)S(N)(=O)=O SPYAZKXNUSPUAC-UHFFFAOYSA-N 0.000 claims description 2
- LAHKGPQYCYERCA-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(5-methylsulfonyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CC2CN(CC2C1)S(=O)(=O)C LAHKGPQYCYERCA-UHFFFAOYSA-N 0.000 claims description 2
- KCDMCFMDJMUHJS-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[(7-methylsulfonyl-2,7-diazaspiro[3.5]nonan-2-yl)methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CC2(C1)CCN(CC2)S(=O)(=O)C KCDMCFMDJMUHJS-UHFFFAOYSA-N 0.000 claims description 2
- RYWQKXMBCXPMGJ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[2-(methanesulfonamido)-1,3-thiazol-4-yl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)C=1N=C(SC=1)NS(=O)(=O)C RYWQKXMBCXPMGJ-UHFFFAOYSA-N 0.000 claims description 2
- XUBSIYATIQEYAZ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[2-(oxan-4-yl)ethoxy]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)OCCC1CCOCC1 XUBSIYATIQEYAZ-UHFFFAOYSA-N 0.000 claims description 2
- NMVTXGPXHRXICH-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[(4-oxocyclohexanecarbonyl)amino]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CNC(=O)C1CCC(CC1)=O NMVTXGPXHRXICH-UHFFFAOYSA-N 0.000 claims description 2
- QEOBIEMNEOSRJL-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[1-(trifluoromethylsulfonyl)piperidin-4-yl]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CC1CCN(CC1)S(=O)(=O)C(F)(F)F QEOBIEMNEOSRJL-UHFFFAOYSA-N 0.000 claims description 2
- LSCAHHFGASPIQL-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[2-(trifluoromethyl)phenoxy]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=C(C=CC=C1)C(F)(F)F LSCAHHFGASPIQL-UHFFFAOYSA-N 0.000 claims description 2
- AABYQVMWTNXOHY-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[3-(trifluoromethyl)phenoxy]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC(=CC=C1)C(F)(F)F AABYQVMWTNXOHY-UHFFFAOYSA-N 0.000 claims description 2
- JXFYBUHDWPBLBW-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CC(CCC1)C(F)(F)F JXFYBUHDWPBLBW-UHFFFAOYSA-N 0.000 claims description 2
- NAHHVGXAXPWJHS-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[4-(1,3-thiazol-2-yl)piperazin-1-yl]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN1CCN(CC1)C=1SC=CN=1 NAHHVGXAXPWJHS-UHFFFAOYSA-N 0.000 claims description 2
- RMVRPYHHYHZXKF-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[4-(trifluoromethyl)phenoxy]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)COC1=CC=C(C=C1)C(F)(F)F RMVRPYHHYHZXKF-UHFFFAOYSA-N 0.000 claims description 2
- XCMGNOFCQPEQBC-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-oxo-2-(trifluoromethyl)-3H-quinazolin-6-yl]ethynyl]benzoic acid Chemical compound FC(C1=NC2=CC=C(C=C2C(N1)=O)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)(F)F XCMGNOFCQPEQBC-UHFFFAOYSA-N 0.000 claims description 2
- KZYKRTVYDSKVBV-UHFFFAOYSA-N 2-amino-4-[4-[2-[3-carboxy-2-(1H-indol-6-yl)phenyl]ethynyl]phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound NC=1SC(=C(N=1)C1=CC=C(C=C1)C#CC1=C(C(=CC=C1)C(=O)O)C1=CC=C2C=CNC2=C1)C(=O)O KZYKRTVYDSKVBV-UHFFFAOYSA-N 0.000 claims description 2
- IZMWWWIVJZRSGM-UHFFFAOYSA-N 3-[2-(2-acetyl-1,3-dihydroisoindol-5-yl)ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)(=O)N1CC2=CC=C(C=C2C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 IZMWWWIVJZRSGM-UHFFFAOYSA-N 0.000 claims description 2
- SISQHXNSJGOONX-UHFFFAOYSA-N 3-[2-(2-acetyl-3,4-dihydro-1H-isoquinolin-6-yl)ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)(=O)N1CC2=CC=C(C=C2CC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 SISQHXNSJGOONX-UHFFFAOYSA-N 0.000 claims description 2
- OVZDRNHRRWYARV-UHFFFAOYSA-N 3-[2-[1-(4-ethoxy-2-methylbutyl)-6-fluoroindol-5-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)OCCC(CN1C=CC2=CC(=C(C=C12)F)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C OVZDRNHRRWYARV-UHFFFAOYSA-N 0.000 claims description 2
- OSQWELUSTCHWHF-UHFFFAOYSA-N 3-[2-[1-[2-(dimethylamino)ethyl]pyrrolo[2,3-b]pyridin-3-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(CCN1C=C(C=2C1=NC=CC=2)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C OSQWELUSTCHWHF-UHFFFAOYSA-N 0.000 claims description 2
- NQUGMBDLJNMQAP-UHFFFAOYSA-N 3-[2-[1-[2-(dimethylamino)ethyl]pyrrolo[2,3-b]pyridin-5-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(CCN1C=CC=2C1=NC=C(C=2)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C NQUGMBDLJNMQAP-UHFFFAOYSA-N 0.000 claims description 2
- BMUKNTCVYFLFAT-UHFFFAOYSA-N 3-[2-[1-[3-(dimethylamino)propyl]pyrrolo[2,3-b]pyridin-3-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(CCCN1C=C(C=2C1=NC=CC=2)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C BMUKNTCVYFLFAT-UHFFFAOYSA-N 0.000 claims description 2
- BGDPQBPEPSLHIR-UHFFFAOYSA-N 3-[2-[1-[3-(dimethylamino)propyl]pyrrolo[2,3-b]pyridin-5-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(CCCN1C=CC=2C1=NC=C(C=2)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C BGDPQBPEPSLHIR-UHFFFAOYSA-N 0.000 claims description 2
- SVRCOOHBECCBBB-UHFFFAOYSA-N 3-[2-[2-[(1-acetylpyrrolidin-3-yl)methyl]-3,4-dihydro-1H-isoquinolin-7-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)(=O)N1CC(CC1)CN1CC2=CC(=CC=C2CC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 SVRCOOHBECCBBB-UHFFFAOYSA-N 0.000 claims description 2
- BKFNYMPKFZVWQY-UHFFFAOYSA-N 3-[2-[2-fluoro-4-(oxan-4-yloxymethyl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1=C(C=CC(=C1)COC1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 BKFNYMPKFZVWQY-UHFFFAOYSA-N 0.000 claims description 2
- VFQMIYHLLBTHHC-UHFFFAOYSA-N 3-[2-[3-(2-amino-1,3-thiazol-4-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC=1SC=C(N=1)C=1C=C(C=CC=1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 VFQMIYHLLBTHHC-UHFFFAOYSA-N 0.000 claims description 2
- JGHMLDVGNZBDQV-UHFFFAOYSA-N 3-[2-[3-(3,3-dimethyl-2-oxoazetidin-1-yl)phenyl]ethynyl]-2-pyrrol-1-ylbenzoic acid Chemical compound CC1(C)CN(C1=O)C1=CC=CC(=C1)C#CC1=CC=CC(C(O)=O)=C1N1C=CC=C1 JGHMLDVGNZBDQV-UHFFFAOYSA-N 0.000 claims description 2
- DJYILMBJPQKXNY-UHFFFAOYSA-N 3-[2-[3-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=CC=C1)CN1CC2=CC=CC=C2CC1 DJYILMBJPQKXNY-UHFFFAOYSA-N 0.000 claims description 2
- GUFRWCQDUZELPA-UHFFFAOYSA-N 3-[2-[3-(3-amino-1H-pyrazol-5-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC1=CC(=NN1)C=1C=C(C=CC=1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 GUFRWCQDUZELPA-UHFFFAOYSA-N 0.000 claims description 2
- RIYLLHKUVSWFMI-UHFFFAOYSA-N 3-[2-[3-[[4-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]carbamoyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound O=S1(CCN(CC1)C1=CC=C(C=C1)NC(=O)C=1C=C(C=CC=1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)=O RIYLLHKUVSWFMI-UHFFFAOYSA-N 0.000 claims description 2
- HFVBIHBHGRKHRO-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(4-morpholin-4-ylpiperidine-1-carbonyl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OC=1C=C(C=CC=1C(=O)N1CCC(CC1)N1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 HFVBIHBHGRKHRO-UHFFFAOYSA-N 0.000 claims description 2
- SWJXPYJQEMRAGK-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(morpholine-4-carbonyl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OC=1C=C(C=CC=1C(=O)N1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 SWJXPYJQEMRAGK-UHFFFAOYSA-N 0.000 claims description 2
- KTRHDLJRFGSXAL-UHFFFAOYSA-N 3-[2-[4-(2-amino-1,3-oxazol-5-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC=1OC(=CN=1)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 KTRHDLJRFGSXAL-UHFFFAOYSA-N 0.000 claims description 2
- SAMLCRHUQMXMTB-UHFFFAOYSA-N 3-[2-[4-(2-amino-1,3-thiazol-4-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC=1SC=C(N=1)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 SAMLCRHUQMXMTB-UHFFFAOYSA-N 0.000 claims description 2
- PYMAZKBGWZYOPA-UHFFFAOYSA-N 3-[2-[4-(2-amino-5-methoxycarbonyl-1,3-thiazol-4-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound COC(=O)C1=C(N=C(S1)N)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 PYMAZKBGWZYOPA-UHFFFAOYSA-N 0.000 claims description 2
- CHEGYYFVXNSVQV-UHFFFAOYSA-N 3-[2-[4-(2-hydroxypropan-2-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OC(C)(C)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 CHEGYYFVXNSVQV-UHFFFAOYSA-N 0.000 claims description 2
- DMVHAOXEPYWTNL-UHFFFAOYSA-N 3-[2-[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C1N(CCC2=CC=CC=C12)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 DMVHAOXEPYWTNL-UHFFFAOYSA-N 0.000 claims description 2
- MUFROQMEWWUGAS-UHFFFAOYSA-N 3-[2-[4-(3-amino-1H-pyrazol-5-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC1=NNC(=C1)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 MUFROQMEWWUGAS-UHFFFAOYSA-N 0.000 claims description 2
- QYRMOTJWXZQKSN-UHFFFAOYSA-N 3-[2-[4-(5-amino-1,3,4-thiadiazol-2-yl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC1=NN=C(S1)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 QYRMOTJWXZQKSN-UHFFFAOYSA-N 0.000 claims description 2
- PSJFHFOPLSOLCK-UHFFFAOYSA-N 3-[2-[4-(benzamidomethyl)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C1=CC=CC=C1)(=O)NCC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 PSJFHFOPLSOLCK-UHFFFAOYSA-N 0.000 claims description 2
- SYAOBLTWUCRKHY-UHFFFAOYSA-N 3-[2-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound O=S1(CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)=O SYAOBLTWUCRKHY-UHFFFAOYSA-N 0.000 claims description 2
- LLKTXEXAWAVEMT-UHFFFAOYSA-N 3-[2-[4-[(1-acetylpiperidin-4-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)(=O)N1CCC(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 LLKTXEXAWAVEMT-UHFFFAOYSA-N 0.000 claims description 2
- UTJWKUPHNOINDU-UHFFFAOYSA-N 3-[2-[4-[(2-cyanophenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(#N)C1=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=CC=C1 UTJWKUPHNOINDU-UHFFFAOYSA-N 0.000 claims description 2
- QWODASCZKHNMMN-UHFFFAOYSA-N 3-[2-[4-[(2-fluorophenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=CC=C1 QWODASCZKHNMMN-UHFFFAOYSA-N 0.000 claims description 2
- NIFJHJDSXPCBQM-UHFFFAOYSA-N 3-[2-[4-[(3,3-difluoropiperidin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1(CN(CCC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)F NIFJHJDSXPCBQM-UHFFFAOYSA-N 0.000 claims description 2
- SMFAFLOVZBYOEO-UHFFFAOYSA-N 3-[2-[4-[(3,4-dichlorophenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound ClC=1C=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=CC=1Cl SMFAFLOVZBYOEO-UHFFFAOYSA-N 0.000 claims description 2
- TWEXJRGYRAECLD-UHFFFAOYSA-N 3-[2-[4-[(3-carbamoylphenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(N)(=O)C=1C=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=CC=1 TWEXJRGYRAECLD-UHFFFAOYSA-N 0.000 claims description 2
- MAJBASYGWNVWLU-UHFFFAOYSA-N 3-[2-[4-[(3-chlorophenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound ClC=1C=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=CC=1 MAJBASYGWNVWLU-UHFFFAOYSA-N 0.000 claims description 2
- CQBWTYJICZTCHM-UHFFFAOYSA-N 3-[2-[4-[(3-cyanophenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(#N)C=1C=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=CC=1 CQBWTYJICZTCHM-UHFFFAOYSA-N 0.000 claims description 2
- SCVLNKRGFHZTEI-UHFFFAOYSA-N 3-[2-[4-[(3-hydroxyazetidin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OC1CN(C1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 SCVLNKRGFHZTEI-UHFFFAOYSA-N 0.000 claims description 2
- HDCOVGYCJXCBGY-UHFFFAOYSA-N 3-[2-[4-[(4,4-difluoropiperidin-1-yl)methyl]-3-methoxyphenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1(CCN(CC1)CC1=C(C=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)OC)F HDCOVGYCJXCBGY-UHFFFAOYSA-N 0.000 claims description 2
- RNXLRAJVQFLNOK-UHFFFAOYSA-N 3-[2-[4-[(4,4-difluoropiperidin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-5-yl)benzoic acid Chemical compound FC1(CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C=1C=C2C=CNC2=CC=1)F RNXLRAJVQFLNOK-UHFFFAOYSA-N 0.000 claims description 2
- PGOAFRJFGQIPBK-UHFFFAOYSA-N 3-[2-[4-[(4,4-difluoropiperidin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1(CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)F PGOAFRJFGQIPBK-UHFFFAOYSA-N 0.000 claims description 2
- MEGICJUCCIZPHU-UHFFFAOYSA-N 3-[2-[4-[(4-carbamoylphenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(N)(=O)C1=CC=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=C1 MEGICJUCCIZPHU-UHFFFAOYSA-N 0.000 claims description 2
- AXJBOACFQWILQG-UHFFFAOYSA-N 3-[2-[4-[(4-cyanophenoxy)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(#N)C1=CC=C(OCC2=CC=C(C=C2)C#CC=2C(=C(C(=O)O)C=CC=2)C2=CC=C3C=CNC3=C2)C=C1 AXJBOACFQWILQG-UHFFFAOYSA-N 0.000 claims description 2
- MRPXSFNKQRJAQZ-UHFFFAOYSA-N 3-[2-[4-[(4-cyclohexylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C1(CCCCC1)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 MRPXSFNKQRJAQZ-UHFFFAOYSA-N 0.000 claims description 2
- CTCLBWSUSAYRQD-UHFFFAOYSA-N 3-[2-[4-[(4-cyclopentylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C1(CCCC1)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 CTCLBWSUSAYRQD-UHFFFAOYSA-N 0.000 claims description 2
- PVADOAVHWHARSW-UHFFFAOYSA-N 3-[2-[4-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C1(CC1)S(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 PVADOAVHWHARSW-UHFFFAOYSA-N 0.000 claims description 2
- JLYRYZUYCZAZTL-UHFFFAOYSA-N 3-[2-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 JLYRYZUYCZAZTL-UHFFFAOYSA-N 0.000 claims description 2
- ICCRUDPOXRVKAG-UHFFFAOYSA-N 3-[2-[4-[(4-ethylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)S(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 ICCRUDPOXRVKAG-UHFFFAOYSA-N 0.000 claims description 2
- KWPIRLGEQFHIJS-UHFFFAOYSA-N 3-[2-[4-[(4-hydroxypiperidin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OC1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 KWPIRLGEQFHIJS-UHFFFAOYSA-N 0.000 claims description 2
- CZBMJYURZCVGDS-UHFFFAOYSA-N 3-[2-[4-[(4-methoxypiperidin-1-yl)methyl]phenyl]ethynyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound COC1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C=1C=C2C(=NC=1)NC=C2 CZBMJYURZCVGDS-UHFFFAOYSA-N 0.000 claims description 2
- VEFXQESAZQCJKU-UHFFFAOYSA-N 3-[2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound CN1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C=1C=C2C(=NC=1)NC=C2 VEFXQESAZQCJKU-UHFFFAOYSA-N 0.000 claims description 2
- VUMNFPQQGWRMPS-UHFFFAOYSA-N 3-[2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound CS(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C=1C=C2C(=NC=1)NC=C2 VUMNFPQQGWRMPS-UHFFFAOYSA-N 0.000 claims description 2
- AUXHNKWTXFGXSO-UHFFFAOYSA-N 3-[2-[4-[(dimethylamino)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(C)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 AUXHNKWTXFGXSO-UHFFFAOYSA-N 0.000 claims description 2
- ORSVZNANHXTGSJ-UHFFFAOYSA-N 3-[2-[4-[3-(hydroxymethyl)oxetan-3-yl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OCC1(COC1)C1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 ORSVZNANHXTGSJ-UHFFFAOYSA-N 0.000 claims description 2
- JSHRSAVRLWVHIY-UHFFFAOYSA-N 3-[2-[4-[[2-(dimethylamino)ethyl-methylamino]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(CCN(C)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C JSHRSAVRLWVHIY-UHFFFAOYSA-N 0.000 claims description 2
- WKPQHLMEHLCMRD-UHFFFAOYSA-N 3-[2-[4-[[4-(2-hydroxyethyl)piperidin-1-yl]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OCCC1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 WKPQHLMEHLCMRD-UHFFFAOYSA-N 0.000 claims description 2
- BQWPNWPDBQRVJW-UHFFFAOYSA-N 3-[2-[4-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 BQWPNWPDBQRVJW-UHFFFAOYSA-N 0.000 claims description 2
- AZFZSHNXRXSTAA-UHFFFAOYSA-N 3-[2-[4-[[4-(cyclopropanecarbonyl)piperazin-1-yl]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C1(CC1)C(=O)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 AZFZSHNXRXSTAA-UHFFFAOYSA-N 0.000 claims description 2
- IOYQBAGLDAVPPN-UHFFFAOYSA-N 3-[2-[4-[[4-(dimethylcarbamoyl)piperazin-1-yl]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(C(=O)N1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)C IOYQBAGLDAVPPN-UHFFFAOYSA-N 0.000 claims description 2
- VIZFIKVINIAZIP-UHFFFAOYSA-N 3-[2-[4-[[4-(dimethylcarbamoyl)piperidin-1-yl]methyl]-3-methoxyphenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound CN(C(=O)C1CCN(CC1)CC1=C(C=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)OC)C VIZFIKVINIAZIP-UHFFFAOYSA-N 0.000 claims description 2
- ZVYPAXPYXFNPNA-UHFFFAOYSA-N 3-[2-[4-[[4-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OCC1CCN(CC1)CC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 ZVYPAXPYXFNPNA-UHFFFAOYSA-N 0.000 claims description 2
- ZOVHWIBYLVZFAH-UHFFFAOYSA-N 3-[2-[6-fluoro-3-(morpholin-4-ylmethyl)-1H-indol-5-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1=C(C=C2C(=CNC2=C1)CN1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 ZOVHWIBYLVZFAH-UHFFFAOYSA-N 0.000 claims description 2
- HQKRTZZXCIYQDQ-UHFFFAOYSA-N 3-[2-[7-fluoro-1-(oxan-4-ylmethyl)indol-6-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC=1C(=CC=C2C=CN(C=12)CC1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 HQKRTZZXCIYQDQ-UHFFFAOYSA-N 0.000 claims description 2
- HGSBHLVDLDNFJX-UHFFFAOYSA-N 3-[2-[7-fluoro-3-(morpholin-4-ylmethyl)-1H-indol-6-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC=1C(=CC=C2C(=CNC=12)CN1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 HGSBHLVDLDNFJX-UHFFFAOYSA-N 0.000 claims description 2
- MSLVMOUJPQDKNJ-UHFFFAOYSA-N 6-[2-[2-[4-(oxan-4-yloxymethyl)phenyl]ethynyl]-6-(2H-tetrazol-5-yl)phenyl]-1H-indole Chemical compound O1CCC(CC1)OCC1=CC=C(C=C1)C#CC1=C(C(=CC=C1)C1=NN=NN1)C1=CC=C2C=CNC2=C1 MSLVMOUJPQDKNJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 206010073478 Anaplastic large-cell lymphoma Diseases 0.000 claims description 2
- 208000036170 B-Cell Marginal Zone Lymphoma Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 claims description 2
- 206010007953 Central nervous system lymphoma Diseases 0.000 claims description 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 206010053574 Immunoblastic lymphoma Diseases 0.000 claims description 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 2
- 208000032004 Large-Cell Anaplastic Lymphoma Diseases 0.000 claims description 2
- 208000018142 Leiomyosarcoma Diseases 0.000 claims description 2
- 208000030289 Lymphoproliferative disease Diseases 0.000 claims description 2
- 201000003791 MALT lymphoma Diseases 0.000 claims description 2
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims description 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 2
- 206010029461 Nodal marginal zone B-cell lymphomas Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 206010036711 Primary mediastinal large B-cell lymphomas Diseases 0.000 claims description 2
- 206010038802 Reticuloendothelial system stimulated Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 201000003444 follicular lymphoma Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 206010066957 hepatosplenic T-cell lymphoma Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 201000006747 infectious mononucleosis Diseases 0.000 claims description 2
- 210000002751 lymph Anatomy 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 2
- 210000000822 natural killer cell Anatomy 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 210000004180 plasmocyte Anatomy 0.000 claims description 2
- 208000017805 post-transplant lymphoproliferative disease Diseases 0.000 claims description 2
- 208000016800 primary central nervous system lymphoma Diseases 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 206010062113 splenic marginal zone lymphoma Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- SXMKYGICIGZSLH-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[(1-methylsulfonylazetidin-3-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)CC1CN(C1)S(=O)(=O)C SXMKYGICIGZSLH-UHFFFAOYSA-N 0.000 claims 1
- FPAGHLWFFGJRNH-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[3-[3-(methanesulfonamido)phenyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=CC=C1)C1=CC(=CC=C1)NS(=O)(=O)C FPAGHLWFFGJRNH-UHFFFAOYSA-N 0.000 claims 1
- KWGPMEFQYOZPRK-UHFFFAOYSA-N 3-[2-[1-[(1,1-dioxothian-4-yl)methyl]-6-fluoroindol-5-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound O=S1(CCC(CC1)CN1C=CC2=CC(=C(C=C12)F)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)=O KWGPMEFQYOZPRK-UHFFFAOYSA-N 0.000 claims 1
- KPELZQOGHLEBET-UHFFFAOYSA-N 3-[2-[4-[(1,1-dioxothian-4-yl)oxymethyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound OC(=O)c1cccc(C#Cc2ccc(COC3CCS(=O)(=O)CC3)cc2)c1-c1ccc2cc[nH]c2c1 KPELZQOGHLEBET-UHFFFAOYSA-N 0.000 claims 1
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000002971 Immunoblastic Lymphadenopathy Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 claims 1
- 208000022766 lymph node neoplasm Diseases 0.000 claims 1
- 208000006116 lymphomatoid granulomatosis Diseases 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 210000004303 peritoneum Anatomy 0.000 claims 1
- 210000004224 pleura Anatomy 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 210000001215 vagina Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- QWEYNXHDCCMAAJ-UHFFFAOYSA-N 2-(1,3-benzothiazol-5-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound S1C=NC2=C1C=CC(=C2)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 QWEYNXHDCCMAAJ-UHFFFAOYSA-N 0.000 description 1
- UTESSWMDJJYDKG-UHFFFAOYSA-N 2-(1,3-benzothiazol-6-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound S1C=NC2=C1C=C(C=C2)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 UTESSWMDJJYDKG-UHFFFAOYSA-N 0.000 description 1
- RJJFPJLBFRWRJQ-UHFFFAOYSA-N 2-(1,8-naphthyridin-2-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound N1=C(C=CC2=CC=CN=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 RJJFPJLBFRWRJQ-UHFFFAOYSA-N 0.000 description 1
- HKUSYXUBWHCAQC-UHFFFAOYSA-N 2-(1,8-naphthyridin-3-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound N1=CC(=CC2=CC=CN=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 HKUSYXUBWHCAQC-UHFFFAOYSA-N 0.000 description 1
- VMEYEKCRSXUKQO-UHFFFAOYSA-N 2-(1-methylpyrrolo[2,3-b]pyridin-6-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound CN1C=CC=2C1=NC(=CC=2)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 VMEYEKCRSXUKQO-UHFFFAOYSA-N 0.000 description 1
- GPTBPINLHZOQQL-UHFFFAOYSA-N 2-(1H-indol-5-yl)-3-[2-[4-(oxan-4-yloxy)phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC(=CC=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)OC1CCOCC1 GPTBPINLHZOQQL-UHFFFAOYSA-N 0.000 description 1
- CBDKGEHWFRUPDR-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-(3-sulfamoylphenyl)ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC(=CC=C1)S(N)(=O)=O CBDKGEHWFRUPDR-UHFFFAOYSA-N 0.000 description 1
- YCDFQNWNYFATOY-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[2-[[3-(methanesulfonamido)phenyl]methyl]-3,4-dihydro-1H-isoquinolin-6-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=C2CCN(CC2=CC=1)CC1=CC(=CC=C1)NS(=O)(=O)C YCDFQNWNYFATOY-UHFFFAOYSA-N 0.000 description 1
- QFUVNCFCTFUKCU-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[4-[[2-methoxyethyl(methyl)amino]methyl]phenyl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)CN(C)CCOC QFUVNCFCTFUKCU-UHFFFAOYSA-N 0.000 description 1
- NFAPCTGXTVGKTM-UHFFFAOYSA-N 2-(1H-indol-6-yl)-3-[2-[6-(oxan-4-yloxy)pyridin-3-yl]ethynyl]benzoic acid Chemical compound N1C=CC2=CC=C(C=C12)C1=C(C(=O)O)C=CC=C1C#CC=1C=NC(=CC=1)OC1CCOCC1 NFAPCTGXTVGKTM-UHFFFAOYSA-N 0.000 description 1
- DOPYCEDMFIVJCZ-UHFFFAOYSA-N 2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound N1C=CC=2C1=NC=C(C=2)C1=C(C(=O)O)C=CC=C1 DOPYCEDMFIVJCZ-UHFFFAOYSA-N 0.000 description 1
- GVWHSZWPCYMGHS-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-5-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound CC=1SC2=C(N=1)C=C(C=C2)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 GVWHSZWPCYMGHS-UHFFFAOYSA-N 0.000 description 1
- YHZFGJBJWPCGGH-UHFFFAOYSA-N 2-(4-methoxy-1H-indol-6-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound COC1=C2C=CNC2=CC(=C1)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 YHZFGJBJWPCGGH-UHFFFAOYSA-N 0.000 description 1
- BFMKKXQGTZYZGZ-UHFFFAOYSA-N 2-(5-fluoro-1H-indol-6-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound FC=1C=C2C=CNC2=CC=1C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 BFMKKXQGTZYZGZ-UHFFFAOYSA-N 0.000 description 1
- KZODBHXNUWLDKN-UHFFFAOYSA-N 2-(6-fluoro-1H-indol-5-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound FC1=C(C=C2C=CNC2=C1)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 KZODBHXNUWLDKN-UHFFFAOYSA-N 0.000 description 1
- NDURDOZDFNHDNW-UHFFFAOYSA-N 2-(7-fluoro-1H-indol-6-yl)-3-(2-phenylethynyl)benzoic acid Chemical compound FC=1C(=CC=C2C=CNC=12)C1=C(C(=O)O)C=CC=C1C#CC1=CC=CC=C1 NDURDOZDFNHDNW-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JSAPZTGMBQIGBM-UHFFFAOYSA-N 3-(2-phenylethynyl)-2-(1H-pyrrolo[2,3-b]pyridin-6-yl)benzoic acid Chemical compound C1(=CC=CC=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C(=N1)NC=C2 JSAPZTGMBQIGBM-UHFFFAOYSA-N 0.000 description 1
- ZJWPKRKUNMOXKN-UHFFFAOYSA-N 3-[2-(4-amino-3-sulfamoylphenyl)ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound NC1=C(C=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)S(N)(=O)=O ZJWPKRKUNMOXKN-UHFFFAOYSA-N 0.000 description 1
- DXWNLPVSWJNKIH-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)ethynyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound FC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C=1C=C2C(=NC=1)NC=C2 DXWNLPVSWJNKIH-UHFFFAOYSA-N 0.000 description 1
- PKAZHOIVXMZAEV-UHFFFAOYSA-N 3-[2-(4-methoxyphenyl)ethynyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound COC1=CC=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C=1C=C2C(=NC=1)NC=C2 PKAZHOIVXMZAEV-UHFFFAOYSA-N 0.000 description 1
- AJOGMXFQIIFBDV-UHFFFAOYSA-N 3-[2-[1-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propyl]indol-5-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound O=S1(CCN(CC1)CCCN1C=CC2=CC(=CC=C12)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)=O AJOGMXFQIIFBDV-UHFFFAOYSA-N 0.000 description 1
- RLAHDXZSHKAYRX-UHFFFAOYSA-N 3-[2-[1-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propyl]indol-6-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound O=S1(CCN(CC1)CCCN1C=CC2=CC=C(C=C12)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)=O RLAHDXZSHKAYRX-UHFFFAOYSA-N 0.000 description 1
- UFNCBZBXMAWHMA-UHFFFAOYSA-N 3-[2-[2-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-1H-indol-6-yl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound O=S1(CCN(CC1)CC=1NC2=CC(=CC=C2C=1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)=O UFNCBZBXMAWHMA-UHFFFAOYSA-N 0.000 description 1
- AOQYKSMYFXXKRX-UHFFFAOYSA-N 3-[2-[3-[(4-ethoxycarbonylpiperazin-1-yl)methyl]phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)OC(=O)N1CCN(CC1)CC=1C=C(C=CC=1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 AOQYKSMYFXXKRX-UHFFFAOYSA-N 0.000 description 1
- HWGLBFQEFKZSPJ-UHFFFAOYSA-N 3-[2-[3-acetamido-4-(oxan-4-yloxy)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(C)(=O)NC=1C=C(C=CC=1OC1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 HWGLBFQEFKZSPJ-UHFFFAOYSA-N 0.000 description 1
- ADDXRZBZDYQSHQ-UHFFFAOYSA-N 3-[2-[3-cyano-4-(oxan-4-yloxy)phenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound C(#N)C=1C=C(C=CC=1OC1CCOCC1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1 ADDXRZBZDYQSHQ-UHFFFAOYSA-N 0.000 description 1
- JPQCPXRDNRAQMM-UHFFFAOYSA-N 3-[2-[4-(4,4-difluoropiperidine-1-carbonyl)-3-hydroxyphenyl]ethynyl]-2-(1H-indol-6-yl)benzoic acid Chemical compound FC1(CCN(CC1)C(=O)C1=C(C=C(C=C1)C#CC=1C(=C(C(=O)O)C=CC=1)C1=CC=C2C=CNC2=C1)O)F JPQCPXRDNRAQMM-UHFFFAOYSA-N 0.000 description 1
- WAMAHFQHBUXIJK-UHFFFAOYSA-N 3-[2-[4-(oxan-4-yloxy)phenyl]ethynyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid Chemical compound N1C=CC=2C1=NC=C(C=2)C1=C(C(=O)O)C=CC=C1C#CC1=CC=C(C=C1)OC1CCOCC1 WAMAHFQHBUXIJK-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 208000008771 Lymphadenopathy Diseases 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 206010065857 Primary Effusion Lymphoma Diseases 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 208000033779 X-linked lymphoproliferative disease Diseases 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 208000018555 lymphatic system disease Diseases 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562161490P | 2015-05-14 | 2015-05-14 | |
| US62/161,490 | 2015-05-14 | ||
| PCT/US2016/032574 WO2016183534A1 (en) | 2015-05-14 | 2016-05-14 | Ebna1 inhibitors and methods using same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018520096A JP2018520096A (ja) | 2018-07-26 |
| JP2018520096A5 true JP2018520096A5 (enExample) | 2019-06-06 |
| JP6771491B2 JP6771491B2 (ja) | 2020-10-21 |
Family
ID=57249496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017559303A Active JP6771491B2 (ja) | 2015-05-14 | 2016-05-14 | Ｅｂｎａ１阻害剤およびその使用方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US10442763B2 (enExample) |
| EP (1) | EP3294705B1 (enExample) |
| JP (1) | JP6771491B2 (enExample) |
| KR (1) | KR102616818B1 (enExample) |
| CN (2) | CN113149885A (enExample) |
| AU (1) | AU2016262572B2 (enExample) |
| BR (1) | BR112017024481B1 (enExample) |
| CA (1) | CA2985348C (enExample) |
| MX (1) | MX2017014550A (enExample) |
| SG (1) | SG11201708820TA (enExample) |
| WO (1) | WO2016183534A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102616818B1 (ko) | 2015-05-14 | 2023-12-22 | 더 위스타 인스티튜트 오브 아나토미 앤드 바이올로지 | Ebna1 억제제 및 그의 사용 방법 |
| AR113299A1 (es) | 2017-06-02 | 2020-04-08 | Hoffmann La Roche | Compuestos de isoindolina |
| ES2927480T3 (es) * | 2017-06-02 | 2022-11-07 | Hoffmann La Roche | Compuestos de isoindolina-acetileno para el tratamiento del cáncer |
| CN112543634A (zh) * | 2018-05-17 | 2021-03-23 | 威斯达研究所 | Ebna1抑制剂晶体形式及其制备和使用方法 |
| EP3814351A1 (en) | 2018-06-29 | 2021-05-05 | F. Hoffmann-La Roche AG | Compounds |
| CN109336857A (zh) * | 2018-11-13 | 2019-02-15 | 南方医科大学 | 一种含取代联苯的黄酮及其应用 |
| MX2021015889A (es) | 2019-06-21 | 2022-02-03 | Hoffmann La Roche | Nuevos inhibidores de egfr. |
| WO2020254572A1 (en) | 2019-06-21 | 2020-12-24 | F. Hoffmann-La Roche Ag | Egfr inhibitors for the treatment of cancer |
| CN113754541B (zh) * | 2020-06-02 | 2025-01-03 | 深圳湾实验室 | 靶向eb病毒核抗原蛋白的小分子抑制剂、制备方法及其应用 |
| CN116135850A (zh) * | 2021-11-16 | 2023-05-19 | 深圳湾实验室 | 抗鼻咽癌的小分子抑制剂、化合物的制备方法及其应用 |
| WO2024050408A1 (en) * | 2022-08-30 | 2024-03-07 | The Wistar Institute Of Anatomy And Biology | Development of a novel ebna-1 degrader targeting through mdm2 |
| CN117586230B (zh) * | 2023-10-20 | 2024-09-24 | 南方医科大学深圳医院 | 降解ebna1的protac化合物及其制备方法和应用 |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56117398A (en) | 1980-02-18 | 1981-09-14 | Nec Corp | Data processor |
| HU190007B (en) | 1982-05-06 | 1986-08-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for producing new aromatic prostacylin analogues |
| US5169645A (en) | 1989-10-31 | 1992-12-08 | Duquesne University Of The Holy Ghost | Directly compressible granules having improved flow properties |
| DE3936297A1 (de) | 1989-11-01 | 1991-05-02 | Bayer Ag | Verfahren zur herstellung von symmetrischen diarylacetylenen |
| DE4039448A1 (de) | 1990-12-11 | 1992-06-17 | Rhein Chemie Rheinau Gmbh | Polyurethan-katalysatoren |
| US5356919A (en) | 1991-05-30 | 1994-10-18 | G. D. Searle & Co. | Leukotriene B4 synthesis inhibitors |
| US6166028A (en) | 1998-12-09 | 2000-12-26 | American Home Products Corporation | Diaminopuridine-containing thiourea inhibitors of herpes viruses |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| DE10021246A1 (de) | 2000-04-25 | 2001-10-31 | Schering Ag | Substituierte Benzoesäureamide und deren Verwendung als Arzneimittel |
| MXPA02011400A (es) | 2000-05-22 | 2003-05-23 | Aventis Pharm Prod Inc | Derivados de arimetilamina para uso como inhibidores de triptasa. |
| ES2284138T3 (es) | 2000-05-31 | 2007-11-01 | Santen Pharmaceutical Co., Ltd. | Inhibidores de la produccion de tnf-alfa para el tratamiento de enfermedades autoinmunes. |
| US6811983B2 (en) | 2001-07-26 | 2004-11-02 | Wisconsin Alumni Research Foundation | Method of identifying inhibitors of EBNA-1 |
| JPWO2003024913A1 (ja) * | 2001-09-17 | 2004-12-24 | 第一サントリーファーマ株式会社 | ＮＦ−κＢ阻害作用を有する置換安息香酸誘導体 |
| US20030187026A1 (en) * | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| US20040044041A1 (en) | 2002-08-06 | 2004-03-04 | Kuduk Scott D. | 2-(Biarylalkyl)amino-3-(cyanoalkanoylamino)pyridine derivatives |
| US7361743B2 (en) | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
| CN1288117C (zh) | 2004-04-02 | 2006-12-06 | 中国科学院上海有机化学研究所 | 端基炔烃和芳基卤化物的偶联反应 |
| CA2570213C (en) * | 2004-07-02 | 2014-02-18 | The Walter And Eliza Hall Institute Of Medical Research | Alpha-helical mimetics |
| JP2008506702A (ja) | 2004-07-14 | 2008-03-06 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎を治療するための方法 |
| JP4787254B2 (ja) | 2004-08-05 | 2011-10-05 | エフ．ホフマン−ラ ロシュ アーゲー | インドール、インダゾールまたはインドリン誘導体 |
| WO2006124581A2 (en) | 2005-05-12 | 2006-11-23 | Wyeth | Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (fsh-r) antagonists |
| TWI473808B (zh) | 2005-06-22 | 2015-02-21 | Plexxikon Inc | 用於激酶調節的化合物及方法及其適應症 |
| WO2007002587A2 (en) * | 2005-06-24 | 2007-01-04 | The Brigham And Women's Hospital, Inc. | Inhibitors of epstein barr virus nuclear antigen 1 |
| WO2007023242A1 (en) | 2005-08-24 | 2007-03-01 | Merz Pharma Gmbh & Co. Kgaa | Tetrahydroquinolinones and their use as modulators of metabotropic glutamate receptors |
| US8022217B2 (en) | 2006-07-31 | 2011-09-20 | Cadila Healthcare Limited | Compounds suitable as modulators of HDL |
| US7956216B2 (en) | 2006-12-21 | 2011-06-07 | The Walter And Eliza Hall Institute Of Medical Research | Alpha-helical mimetics |
| BRPI0919920A2 (pt) | 2008-10-22 | 2016-02-16 | Acucela Inc | compostos para tratamento de doenças e desordens oftálmicas |
| AU2010212970A1 (en) | 2009-02-12 | 2011-08-18 | Merck Serono S.A. | Phenoxy acetic acid derivatives |
| WO2010100475A1 (en) | 2009-03-02 | 2010-09-10 | Astrazeneca Ab | Hydroxamic acid derivatives as gram-negative antibacterial agents |
| US8927576B2 (en) | 2009-04-06 | 2015-01-06 | PTC Therpeutics, Inc. | HCV inhibitor and therapeutic agent combinations |
| US20100273772A1 (en) | 2009-04-23 | 2010-10-28 | Wyeth Llc | Bisaryl Alkynylamides as Negative Allosteric Modulators of Metabotropic Glutamate Receptor 5 (MGLUR5) |
| PT2427416E (pt) | 2009-05-04 | 2016-06-15 | Prometic Pharma Smt Ltd | Compostos aromáticos substituídos e seus usos farmacêuticos |
| EP2519517B1 (en) * | 2009-12-29 | 2015-03-25 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
| WO2011082098A1 (en) | 2009-12-30 | 2011-07-07 | The Rockefeller University | Lysine and arginine methyltransferase inhibitors for treating cancer |
| US8735384B2 (en) | 2010-01-19 | 2014-05-27 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| BR112013018212B1 (pt) | 2011-01-21 | 2021-12-14 | Sun Pharma Advanced Research Company Ltd | Inibidores de tirosino quinase contendo diarilacettleno hidrazida |
| EP2714941A4 (en) * | 2011-05-24 | 2014-12-03 | Wistar Inst | COMPOSITIONS AND METHODS FOR MODULATING THE EFFECT OF THE EPSTEIN-BARR NUCLEAR ANTIGEN 1 |
| GB201113538D0 (en) * | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| WO2014011840A1 (en) | 2012-07-12 | 2014-01-16 | Abbvie Inc. | Crystalline forms of an hcv inhibitor |
| EP2968276A4 (en) | 2013-03-15 | 2017-02-15 | President and Fellows of Harvard College | Hybrid necroptosis inhibitors |
| US9637505B2 (en) | 2013-03-15 | 2017-05-02 | Dow Agrosciences Llc | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides |
| MX2016006325A (es) * | 2013-11-15 | 2016-12-02 | Wistar Inst | Inhibidores del antígeno nuclear 1 de epstein-barr, y su método de uso. |
| KR102616818B1 (ko) | 2015-05-14 | 2023-12-22 | 더 위스타 인스티튜트 오브 아나토미 앤드 바이올로지 | Ebna1 억제제 및 그의 사용 방법 |
-
2016
- 2016-05-14 KR KR1020177035828A patent/KR102616818B1/ko active Active
- 2016-05-14 CN CN202110223995.8A patent/CN113149885A/zh active Pending
- 2016-05-14 CA CA2985348A patent/CA2985348C/en active Active
- 2016-05-14 MX MX2017014550A patent/MX2017014550A/es unknown
- 2016-05-14 JP JP2017559303A patent/JP6771491B2/ja active Active
- 2016-05-14 BR BR112017024481-0A patent/BR112017024481B1/pt active IP Right Grant
- 2016-05-14 SG SG11201708820TA patent/SG11201708820TA/en unknown
- 2016-05-14 US US15/571,223 patent/US10442763B2/en active Active
- 2016-05-14 AU AU2016262572A patent/AU2016262572B2/en active Active
- 2016-05-14 EP EP16793664.0A patent/EP3294705B1/en active Active
- 2016-05-14 CN CN201680041102.5A patent/CN107848964B/zh active Active
- 2016-05-14 WO PCT/US2016/032574 patent/WO2016183534A1/en not_active Ceased
-
2019
- 2019-09-16 US US16/571,896 patent/US10981867B2/en active Active
-
2021
- 2021-04-16 US US17/232,511 patent/US11912659B2/en active Active
-
2024
- 2024-01-09 US US18/408,389 patent/US20240246909A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018520096A5 (enExample) | ||
| US11912659B2 (en) | EBNA1 inhibitors and methods using same | |
| JP5865519B2 (ja) | イミダゾピロリジノン化合物 | |
| RU2515972C2 (ru) | Диазакарбазолы и способы применения | |
| JP2016172739A5 (enExample) | ||
| JP2011515462A5 (enExample) | ||
| JP2003535887A5 (enExample) | ||
| US20180289685A1 (en) | Combinations of inhibitors of irak4 with inhibitors of btk | |
| JP2006503010A5 (enExample) | ||
| CA2848148A1 (en) | Benzonitrile derivatives as kinase inhibitors | |
| JP2008513514A5 (enExample) | ||
| CN114430740A (zh) | Egfr抑制剂、组合物及其制备方法 | |
| JP2006520805A5 (enExample) | ||
| RU2014151009A (ru) | Пиразолопиримидоновые и пиразолопиридоновые ингибиторы танкиразы | |
| JP2005537312A5 (enExample) | ||
| JP2010535799A5 (enExample) | ||
| JP2004525965A5 (enExample) | ||
| JP2016514711A5 (enExample) | ||
| WO2013117645A1 (en) | Imidazo [4, 5 -c] pyridine derivatives useful for the treatment of degenerative and inflammatory diseases | |
| WO2022011274A1 (en) | Substituted 1,6-naphthyridine inhibitors of cdk5 | |
| JP2010508328A5 (enExample) | ||
| HK40056148A (en) | Ebna1 inhibitors and methods using same | |
| HK1249497B (en) | Ebna1 inhibitors and methods using same |