JP2018520096A5 - - Google Patents
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- 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
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- -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
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| WO2019222470A1 (en) | 2018-05-17 | 2019-11-21 | The Wistar Institute | Ebna1 inhibitor crystalline forms, and methods of preparing and using same |
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| 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 |
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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 |
| OA12274A (en) | 2000-05-22 | 2006-05-09 | Aventis Pharma Inc | Arylmethylamine derivatives for use as tryptase inhibitors. |
| EP1568692B1 (en) | 2000-05-31 | 2010-09-15 | Santen Pharmaceutical Co., Ltd. | (Pyridinyl)alkyl-amides or -ureas as TNF-alpha production inhibitors |
| US6811983B2 (en) | 2001-07-26 | 2004-11-02 | Wisconsin Alumni Research Foundation | Method of identifying inhibitors of EBNA-1 |
| BR0206036A (pt) * | 2001-09-17 | 2004-01-06 | Daiichi Suntory Pharma Co Ltd | Derivados de ácido benzóico substituìdos tendo ação de inibição de nf-kb |
| 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 |
| NZ551974A (en) * | 2004-07-02 | 2010-01-29 | Inst Medical W & E Hall | Alpha-helical minetics |
| EP1771169A1 (en) | 2004-07-14 | 2007-04-11 | PTC Therapeutics, Inc. | Methods for treating hepatitis c |
| EP1776338A1 (en) | 2004-08-05 | 2007-04-25 | F. Hoffmann-Roche AG | Indole, indazole or indoline derivatives |
| MX2007014085A (es) | 2005-05-12 | 2008-02-07 | Wyeth Corp | Pirrolobenzodiazepinas y derivados de carboxamida heterociclica como antagonistas de receptor de hormona estimulante del foliculo. |
| DK2395004T3 (en) | 2005-06-22 | 2016-03-21 | Plexxikon Inc | Pyrrolo [2,3-b] pyridine derivatives as protein kinase inhibitors |
| 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 |
| EP2049493B1 (en) | 2006-07-31 | 2012-03-21 | 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 |
| WO2010048332A2 (en) | 2008-10-22 | 2010-04-29 | Acucela, Inc. | Compounds for treating ophthalmic diseases and disorders |
| WO2010092043A1 (en) | 2009-02-12 | 2010-08-19 | 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 |
| WO2010124047A1 (en) | 2009-04-23 | 2010-10-28 | Wyeth Llc | Bisaryl alkynylamides as negative allosteric modulators of metabotropic glutamate receptor 5 (mglur5) |
| MX2011011757A (es) | 2009-05-04 | 2012-01-25 | Prometic Biosciences Inc | Compuestos aromaticos substituidos y usos farmaceuticos. |
| EP2937345B1 (en) | 2009-12-29 | 2018-03-21 | 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 |
| AU2012208388C1 (en) | 2011-01-21 | 2017-04-27 | Sun Pharma Advanced Research Company Ltd | Diarylacetylene hydrazide containing tyrosine kinase inhibitors |
| US9309212B2 (en) * | 2011-05-24 | 2016-04-12 | The Wistar Institute | Compositions and methods for modulating the activity of Epstein-Barr nuclear antigen 1 |
| GB201113538D0 (en) * | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| US9469673B2 (en) | 2012-07-12 | 2016-10-18 | Abbvie Inc. | Crystaline forms of HCV inhibitor |
| 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 |
| EP2968276A4 (en) | 2013-03-15 | 2017-02-15 | President and Fellows of Harvard College | Hybrid necroptosis inhibitors |
| MX2016006325A (es) * | 2013-11-15 | 2016-12-02 | Wistar Inst | Inhibidores del antígeno nuclear 1 de epstein-barr, y su método de uso. |
| EP3294705B1 (en) | 2015-05-14 | 2021-07-21 | The Wistar Institute Of Anatomy And Biology | Ebna1 inhibitors and methods using same |
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