JPWO2021204896A5 - - Google Patents
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- JPWO2021204896A5 JPWO2021204896A5 JP2022561072A JP2022561072A JPWO2021204896A5 JP WO2021204896 A5 JPWO2021204896 A5 JP WO2021204896A5 JP 2022561072 A JP2022561072 A JP 2022561072A JP 2022561072 A JP2022561072 A JP 2022561072A JP WO2021204896 A5 JPWO2021204896 A5 JP WO2021204896A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- benzenacyclotetradecaphan
- diazepan
- dimethoxy
- dioxa
- 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.)
- Pending
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- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims 52
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 32
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims 26
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 19
- 239000012453 solvate Substances 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims 14
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 12
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 9
- -1 carbonylamino, sulfonylamino Chemical group 0.000 claims 9
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 6
- XNBRWUQWSKXMPW-UHFFFAOYSA-N Tozadenant Chemical group C1=2SC(NC(=O)N3CCC(C)(O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 XNBRWUQWSKXMPW-UHFFFAOYSA-N 0.000 claims 6
- 150000001299 aldehydes Chemical class 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims 6
- 150000001345 alkine derivatives Chemical class 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 6
- 125000005096 aminoalkylaminocarbonyl group Chemical group 0.000 claims 6
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 6
- 235000010233 benzoic acid Nutrition 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000005181 hydroxyalkylaminoalkyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 4
- HQSBCDPYXDGTCL-UHFFFAOYSA-N 3-[(4-amino-3-methylphenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=C(N)C(C)=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 HQSBCDPYXDGTCL-UHFFFAOYSA-N 0.000 claims 3
- BUXIAWLTBSXYSW-UHFFFAOYSA-N 3-[2-amino-6-[1-[[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl]triazol-4-yl]pyrimidin-4-yl]-2-methylbenzonitrile Chemical compound CC1=C(C=CC=C1C1=CC(=NC(N)=N1)C1=CN(CC2=NC(=CC=C2)C(C)(C)O)N=N1)C#N BUXIAWLTBSXYSW-UHFFFAOYSA-N 0.000 claims 3
- NCWQLHHDGDXIJN-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(F)=CC=2)=C1 NCWQLHHDGDXIJN-UHFFFAOYSA-N 0.000 claims 3
- KURQKNMKCGYWRJ-HNNXBMFYSA-N 7-(5-methylfuran-2-yl)-3-[[6-[[(3s)-oxolan-3-yl]oxymethyl]pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(CO[C@@H]2COCC2)=N1 KURQKNMKCGYWRJ-HNNXBMFYSA-N 0.000 claims 3
- QYCCLUSYHJXDEX-UHFFFAOYSA-N 7-amino-10-[2-[4-[2,4-difluoro-5-(2-methylsulfinylethoxy)phenyl]piperazin-1-yl]ethyl]-4-(furan-2-yl)-12-thia-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7-tetraen-11-one Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)SC(N2CCN1CCN(CC1)C1=C(C=C(C(=C1)OCCS(=O)C)F)F)=O QYCCLUSYHJXDEX-UHFFFAOYSA-N 0.000 claims 3
- QYCCLUSYHJXDEX-VQJSHJPSSA-N 7-amino-10-[2-[4-[2,4-difluoro-5-[2-[(R)-methylsulfinyl]ethoxy]phenyl]piperazin-1-yl]ethyl]-4-(furan-2-yl)-12-thia-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7-tetraen-11-one Chemical compound C[S@@+]([O-])CCOc1cc(N2CCN(CCn3c4nc(N)n5nc(nc5c4sc3=O)-c3ccco3)CC2)c(F)cc1F QYCCLUSYHJXDEX-VQJSHJPSSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 101150051188 Adora2a gene Proteins 0.000 claims 3
- 101150078577 Adora2b gene Proteins 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 3
- QYCCLUSYHJXDEX-RWYGWLOXSA-N inupadenant Chemical compound C[S@](=O)CCOc1cc(N2CCN(CCn3c4nc(N)n5nc(nc5c4sc3=O)-c3ccco3)CC2)c(F)cc1F QYCCLUSYHJXDEX-RWYGWLOXSA-N 0.000 claims 3
- 150000002923 oximes Chemical class 0.000 claims 3
- DTYWJKSSUANMHD-UHFFFAOYSA-N preladenant Chemical compound C1=CC(OCCOC)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=N2)CC1 DTYWJKSSUANMHD-UHFFFAOYSA-N 0.000 claims 3
- 229940044551 receptor antagonist Drugs 0.000 claims 3
- 239000002464 receptor antagonist Substances 0.000 claims 3
- ATFXVNUWQOXRRU-UHFFFAOYSA-N taminadenant Chemical compound BrC=1C(N)=NC(N2N=CC=C2)=NC=1N1C=CC=N1 ATFXVNUWQOXRRU-UHFFFAOYSA-N 0.000 claims 3
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 claims 2
- YCENSLDYFDZUMO-UHFFFAOYSA-N 3,4,5-triethoxybenzoic acid Chemical compound CCOC1=CC(C(O)=O)=CC(OCC)=C1OCC YCENSLDYFDZUMO-UHFFFAOYSA-N 0.000 claims 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- JVRUZPDYVLRYQT-NGQZWQHPSA-N (1r,5s)-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid Chemical compound C1OC[C@H]2C(C(=O)O)[C@H]21 JVRUZPDYVLRYQT-NGQZWQHPSA-N 0.000 claims 1
- VYKQDWPBYULGPF-UHFFFAOYSA-N 1-benzyl-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1CC1=CC=CC=C1 VYKQDWPBYULGPF-UHFFFAOYSA-N 0.000 claims 1
- KAJLCBKTWRUQOI-UHFFFAOYSA-N 1-methylbenzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N(C)C=NC2=C1 KAJLCBKTWRUQOI-UHFFFAOYSA-N 0.000 claims 1
- HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 claims 1
- QAOJBHRZQQDFHA-UHFFFAOYSA-N 2,3-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1Cl QAOJBHRZQQDFHA-UHFFFAOYSA-N 0.000 claims 1
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 claims 1
- FSJPCGQVHNWRGI-UHFFFAOYSA-N 2-(oxetan-3-yl)acetic acid Chemical compound OC(=O)CC1COC1 FSJPCGQVHNWRGI-UHFFFAOYSA-N 0.000 claims 1
- VCNCNVOMGXWTBZ-UHFFFAOYSA-N 2-chloro-6-fluoro-3-methylbenzoic acid Chemical compound CC1=CC=C(F)C(C(O)=O)=C1Cl VCNCNVOMGXWTBZ-UHFFFAOYSA-N 0.000 claims 1
- UPWMPIKNUXTWFP-UHFFFAOYSA-N 2-fluoro-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(F)=C1 UPWMPIKNUXTWFP-UHFFFAOYSA-N 0.000 claims 1
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 claims 1
- DUFYYKGNRAMGNG-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound N1C(=O)CCC2=CC(C(=O)O)=CC=C21 DUFYYKGNRAMGNG-UHFFFAOYSA-N 0.000 claims 1
- UWOAWSLEKWLDNR-UHFFFAOYSA-N 3,3-dimethylcyclobutane-1-carboxylic acid Chemical compound CC1(C)CC(C(O)=O)C1 UWOAWSLEKWLDNR-UHFFFAOYSA-N 0.000 claims 1
- VPHHJAOJUJHJKD-UHFFFAOYSA-N 3,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1 VPHHJAOJUJHJKD-UHFFFAOYSA-N 0.000 claims 1
- FPENCTDAQQQKNY-UHFFFAOYSA-N 3,4-difluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1 FPENCTDAQQQKNY-UHFFFAOYSA-N 0.000 claims 1
- CXKCZFDUOYMOOP-UHFFFAOYSA-N 3,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(Cl)=C1 CXKCZFDUOYMOOP-UHFFFAOYSA-N 0.000 claims 1
- GONAVIHGXFBTOZ-UHFFFAOYSA-N 3,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC(F)=C1 GONAVIHGXFBTOZ-UHFFFAOYSA-N 0.000 claims 1
- KIJGYTNIFKJHJQ-UHFFFAOYSA-N 3-(1,2,4-triazol-1-yl)propanoic acid Chemical compound OC(=O)CCN1C=NC=N1 KIJGYTNIFKJHJQ-UHFFFAOYSA-N 0.000 claims 1
- DPISPNNORVOBQY-UHFFFAOYSA-N 3-(2,5-dioxopyrrolidin-1-yl)propanoic acid Chemical compound OC(=O)CCN1C(=O)CCC1=O DPISPNNORVOBQY-UHFFFAOYSA-N 0.000 claims 1
- QCEDXODAYRWQRH-UHFFFAOYSA-N 3-(4-fluorophenoxy)propanoic acid Chemical compound OC(=O)CCOC1=CC=C(F)C=C1 QCEDXODAYRWQRH-UHFFFAOYSA-N 0.000 claims 1
- OKKDGIXOKWOMRD-UHFFFAOYSA-N 3-(difluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC(OC(F)F)=C1 OKKDGIXOKWOMRD-UHFFFAOYSA-N 0.000 claims 1
- WMTYEYUOSFTJBH-UHFFFAOYSA-N 3-(tetrazol-1-yl)propanoic acid Chemical compound OC(=O)CCN1C=NN=N1 WMTYEYUOSFTJBH-UHFFFAOYSA-N 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 1
- PKTSBFXIHLYGEY-UHFFFAOYSA-N 3-chloro-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(Cl)=C1 PKTSBFXIHLYGEY-UHFFFAOYSA-N 0.000 claims 1
- JMHGATOBRPWPBZ-UHFFFAOYSA-N 3-cyano-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(C#N)=C1 JMHGATOBRPWPBZ-UHFFFAOYSA-N 0.000 claims 1
- GYLKKXHEIIFTJH-UHFFFAOYSA-N 3-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC(C#N)=C1 GYLKKXHEIIFTJH-UHFFFAOYSA-N 0.000 claims 1
- BXYQHDXDCJQOFD-UHFFFAOYSA-N 3-cyanopropanoic acid Chemical compound OC(=O)CCC#N BXYQHDXDCJQOFD-UHFFFAOYSA-N 0.000 claims 1
- NSGKIIGVPBTOBF-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(F)=CC(C(F)(F)F)=C1 NSGKIIGVPBTOBF-UHFFFAOYSA-N 0.000 claims 1
- KAWNRNMMEKTYGM-UHFFFAOYSA-N 3-methoxycyclohexane-1-carboxylic acid Chemical compound COC1CCCC(C(O)=O)C1 KAWNRNMMEKTYGM-UHFFFAOYSA-N 0.000 claims 1
- YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-UHFFFAOYSA-N 0.000 claims 1
- QJSRENHDYMAJIL-UHFFFAOYSA-N 3-methyl-5-(trifluoromethyl)benzoic acid Chemical compound CC1=CC(C(O)=O)=CC(C(F)(F)F)=C1 QJSRENHDYMAJIL-UHFFFAOYSA-N 0.000 claims 1
- KUTBMATZUQWFSR-UHFFFAOYSA-N 3-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC(C(O)=O)=C1 KUTBMATZUQWFSR-UHFFFAOYSA-N 0.000 claims 1
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 claims 1
- QSTMEFBMAAWLLV-UHFFFAOYSA-N 3-pyrazol-1-ylpropanoic acid Chemical compound OC(=O)CCN1C=CC=N1 QSTMEFBMAAWLLV-UHFFFAOYSA-N 0.000 claims 1
- FQXQBFUUVCDIRK-UHFFFAOYSA-N 3-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1 FQXQBFUUVCDIRK-UHFFFAOYSA-N 0.000 claims 1
- WTUCTMYLCMVYEX-UHFFFAOYSA-N 4,4,4-trifluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-N 0.000 claims 1
- HYIUDFLDFSIXTR-UHFFFAOYSA-N 4,4-difluorocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(F)(F)CC1 HYIUDFLDFSIXTR-UHFFFAOYSA-N 0.000 claims 1
- XFOJZPTYJMXNKK-UHFFFAOYSA-N 4,5-dichloro-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C=C1F XFOJZPTYJMXNKK-UHFFFAOYSA-N 0.000 claims 1
- MCPBXFWYUHYSIZ-UHFFFAOYSA-N 4-(1,3-oxazol-5-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=CO1 MCPBXFWYUHYSIZ-UHFFFAOYSA-N 0.000 claims 1
- WAIGPJMZARQZDX-UHFFFAOYSA-N 4-(dimethylamino)-4-oxobutanoic acid Chemical compound CN(C)C(=O)CCC(O)=O WAIGPJMZARQZDX-UHFFFAOYSA-N 0.000 claims 1
- RGWXLLFCRBVSBL-UHFFFAOYSA-N 4-(methylamino)-4-oxobutanoic acid Chemical compound CNC(=O)CCC(O)=O RGWXLLFCRBVSBL-UHFFFAOYSA-N 0.000 claims 1
- RATSANVPHHXDCT-UHFFFAOYSA-N 4-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)(F)F)C=C1 RATSANVPHHXDCT-UHFFFAOYSA-N 0.000 claims 1
- LMEAZIIFLVDISW-UHFFFAOYSA-N 4-(trifluoromethyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C(F)(F)F)CC1 LMEAZIIFLVDISW-UHFFFAOYSA-N 0.000 claims 1
- UZTFMUBKZQVKLK-UHFFFAOYSA-N 4-acetamidobutanoic acid Chemical compound CC(=O)NCCCC(O)=O UZTFMUBKZQVKLK-UHFFFAOYSA-N 0.000 claims 1
- HUFXHLPIISLHKJ-UHFFFAOYSA-N 4-bromo-3-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(C#N)=C1 HUFXHLPIISLHKJ-UHFFFAOYSA-N 0.000 claims 1
- ZWKNDLMYSLLMRF-UHFFFAOYSA-N 4-cyano-3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C(F)=C1 ZWKNDLMYSLLMRF-UHFFFAOYSA-N 0.000 claims 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 claims 1
- YXBVMSQDRLXPQV-UHFFFAOYSA-N 4-cyanobutanoic acid Chemical compound OC(=O)CCCC#N YXBVMSQDRLXPQV-UHFFFAOYSA-N 0.000 claims 1
- WZBPZYCJUADXRS-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(F)C(C(F)(F)F)=C1 WZBPZYCJUADXRS-UHFFFAOYSA-N 0.000 claims 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 claims 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 1
- PDDVYCWKVQXOTR-UHFFFAOYSA-N 4-methoxy-2-(trifluoromethoxy)benzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC(F)(F)F)=C1 PDDVYCWKVQXOTR-UHFFFAOYSA-N 0.000 claims 1
- WKILSRYNRQGRMA-UHFFFAOYSA-N 4-methoxycyclohexane-1-carboxylic acid Chemical compound COC1CCC(C(O)=O)CC1 WKILSRYNRQGRMA-UHFFFAOYSA-N 0.000 claims 1
- OJFWUNYQLGJYEO-UHFFFAOYSA-N 4-morpholin-4-yl-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)N1CCOCC1 OJFWUNYQLGJYEO-UHFFFAOYSA-N 0.000 claims 1
- ZVERWTXKKWSSHH-UHFFFAOYSA-N 4-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1 ZVERWTXKKWSSHH-UHFFFAOYSA-N 0.000 claims 1
- SWKPKONEIZGROQ-UHFFFAOYSA-N 4-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(F)(F)F)C=C1 SWKPKONEIZGROQ-UHFFFAOYSA-N 0.000 claims 1
- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 claims 1
- BLHCMGRVFXRYRN-UHFFFAOYSA-N 6-hydroxynicotinic acid Chemical compound OC(=O)C1=CC=C(O)N=C1 BLHCMGRVFXRYRN-UHFFFAOYSA-N 0.000 claims 1
- 102100021469 Equilibrative nucleoside transporter 1 Human genes 0.000 claims 1
- 101000822020 Homo sapiens Equilibrative nucleoside transporter 1 Proteins 0.000 claims 1
- LJLLAWRMBZNPMO-UHFFFAOYSA-N N-acetyl-beta-alanine Chemical compound CC(=O)NCCC(O)=O LJLLAWRMBZNPMO-UHFFFAOYSA-N 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
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| WO2023235464A1 (en) * | 2022-06-01 | 2023-12-07 | Duke University | Novel equilibrative nucleoside transporter inhibitors and methods of making and using same |
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| CN102869631B (zh) | 2010-02-08 | 2016-09-07 | 埃西勒国际通用光学公司 | 包含具有防雾性能的抗反射涂层的光学制品 |
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| TWI801372B (zh) | 2017-03-30 | 2023-05-11 | 比利時商艾特歐斯比利時有限公司 | 作為a2a抑制劑的硫胺甲酸酯衍生物以及用於癌症治療的方法 |
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