NO20004892L - Kinolin-4-yl-derivater I - Google Patents
Kinolin-4-yl-derivater IInfo
- Publication number
- NO20004892L NO20004892L NO20004892A NO20004892A NO20004892L NO 20004892 L NO20004892 L NO 20004892L NO 20004892 A NO20004892 A NO 20004892A NO 20004892 A NO20004892 A NO 20004892A NO 20004892 L NO20004892 L NO 20004892L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- quinolin
- methoxy
- propan
- chloro
- Prior art date
Links
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 184
- -1 hydroxy, amino Chemical group 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 230000004770 neurodegeneration Effects 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 7
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- YYLWPIXZTNVPLE-UHFFFAOYSA-N 1-amino-3-[[2-(4-methoxyphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCC(O)CN)=C(C=CC=C2)C2=N1 YYLWPIXZTNVPLE-UHFFFAOYSA-N 0.000 claims description 3
- LFPSNZFRCSVPHA-UHFFFAOYSA-N 1-amino-3-[[7-methoxy-2-(4-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(NCC(O)CN)=CC=1C1=CC=C(C)C=C1 LFPSNZFRCSVPHA-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- JZVZLICYCUZMOT-ZDUSSCGKSA-N (2s)-1-[[2-(3-chloro-4-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound N=1C2=CC=CC=C2C(NC[C@@H](O)C)=CC=1C1=CC=C(C)C(Cl)=C1 JZVZLICYCUZMOT-ZDUSSCGKSA-N 0.000 claims description 2
- MNXUXICIMVJTRG-AWEZNQCLSA-N (2s)-1-[[2-(4-methoxy-3-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1=C(C)C(OC)=CC=C1C1=CC(NC[C@H](C)O)=C(C=CC=C2)C2=N1 MNXUXICIMVJTRG-AWEZNQCLSA-N 0.000 claims description 2
- SLEGUCQUVMBHIC-UHFFFAOYSA-N 1-(2-phenylquinolin-4-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CNC(C)C)=CC=1C1=CC=CC=C1 SLEGUCQUVMBHIC-UHFFFAOYSA-N 0.000 claims description 2
- HJPCSUFHQXLWME-UHFFFAOYSA-N 1-(7-methoxy-2-phenylquinolin-4-yl)oxy-3-(methylamino)propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=CC=C1 HJPCSUFHQXLWME-UHFFFAOYSA-N 0.000 claims description 2
- NTRCTOSWBGKJJT-UHFFFAOYSA-N 1-(cyclobutylamino)-3-(2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1OCC(O)CNC1CCC1 NTRCTOSWBGKJJT-UHFFFAOYSA-N 0.000 claims description 2
- ITRQUARAZQAGON-UHFFFAOYSA-N 1-(cyclopentylamino)-3-(2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1OCC(O)CNC1CCCC1 ITRQUARAZQAGON-UHFFFAOYSA-N 0.000 claims description 2
- HUGMYBRIUBHLLZ-UHFFFAOYSA-N 1-(methylamino)-3-(7-methyl-2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound N=1C2=CC(C)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=CC=C1 HUGMYBRIUBHLLZ-UHFFFAOYSA-N 0.000 claims description 2
- MLNUFIMLFJTBRP-UHFFFAOYSA-N 1-(methylamino)-3-[2-(4-methylphenyl)quinolin-4-yl]oxypropan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(C)C=C1 MLNUFIMLFJTBRP-UHFFFAOYSA-N 0.000 claims description 2
- SYDIGZPCXFAHPV-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)-7-methylquinolin-4-yl]oxy-3-(methylamino)propan-2-ol Chemical compound N=1C2=CC(C)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(OC)C=C1 SYDIGZPCXFAHPV-UHFFFAOYSA-N 0.000 claims description 2
- KDOZIHYZDYKRKG-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)quinolin-4-yl]oxy-3-(methylamino)propan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(OC)C=C1 KDOZIHYZDYKRKG-UHFFFAOYSA-N 0.000 claims description 2
- MVTSRVCQUBOQER-UHFFFAOYSA-N 1-[7-methoxy-2-(4-methylphenyl)quinolin-4-yl]oxy-3-(methylamino)propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(C)C=C1 MVTSRVCQUBOQER-UHFFFAOYSA-N 0.000 claims description 2
- ZXFFICKRQVKFDH-UHFFFAOYSA-N 1-amino-3-(2-phenylquinolin-4-yl)oxypropan-2-ol Chemical compound N=1C2=CC=CC=C2C(OCC(O)CN)=CC=1C1=CC=CC=C1 ZXFFICKRQVKFDH-UHFFFAOYSA-N 0.000 claims description 2
- YNNOGKJEUMGWHX-UHFFFAOYSA-N 1-amino-3-[[2-(4-methylphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1=CC(C)=CC=C1C1=CC(NCC(O)CN)=C(C=CC=C2)C2=N1 YNNOGKJEUMGWHX-UHFFFAOYSA-N 0.000 claims description 2
- GEKIARRHTXRYNN-UHFFFAOYSA-N 1-amino-3-[[7-methoxy-2-(4-methoxyphenyl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCC(O)CN)=C(C=CC(OC)=C2)C2=N1 GEKIARRHTXRYNN-UHFFFAOYSA-N 0.000 claims description 2
- LXBAEGKBCVHTGA-UHFFFAOYSA-N 2-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]ethanol Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCCO)=C1 LXBAEGKBCVHTGA-UHFFFAOYSA-N 0.000 claims description 2
- PNFBNNDNLLGKLE-UHFFFAOYSA-N 2-[[2-(4-methoxyphenyl)-7-methylquinolin-4-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCO)=C(C=CC(C)=C2)C2=N1 PNFBNNDNLLGKLE-UHFFFAOYSA-N 0.000 claims description 2
- RVXYSGFHWJGYCX-UHFFFAOYSA-N 2-[[7-methoxy-2-(4-methoxyphenyl)quinolin-4-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCO)=C(C=CC(OC)=C2)C2=N1 RVXYSGFHWJGYCX-UHFFFAOYSA-N 0.000 claims description 2
- FBJVPWUZWFKALU-UHFFFAOYSA-N 2-[[7-methyl-2-(4-methylphenyl)quinolin-4-yl]amino]ethanol Chemical compound C1=CC(C)=CC=C1C1=CC(NCCO)=C(C=CC(C)=C2)C2=N1 FBJVPWUZWFKALU-UHFFFAOYSA-N 0.000 claims description 2
- XPNJWYYAPBKDAQ-UHFFFAOYSA-N 2-amino-1-(6-chloro-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=CC=C(Cl)C=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 XPNJWYYAPBKDAQ-UHFFFAOYSA-N 0.000 claims description 2
- JJDMFYFYSVVGPI-UHFFFAOYSA-N 2-amino-1-(6-methoxy-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=CC=C(OC)C=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 JJDMFYFYSVVGPI-UHFFFAOYSA-N 0.000 claims description 2
- YFBMGEUUCADRTG-UHFFFAOYSA-N 2-amino-1-(6-methyl-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=CC=C(C)C=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 YFBMGEUUCADRTG-UHFFFAOYSA-N 0.000 claims description 2
- VVTQNXBVHXWXIY-UHFFFAOYSA-N 2-amino-1-(8-methoxy-2-phenylquinolin-4-yl)butan-1-ol Chemical compound N=1C2=C(OC)C=CC=C2C(C(O)C(N)CC)=CC=1C1=CC=CC=C1 VVTQNXBVHXWXIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- GGOIZDJNKGSNQN-UHFFFAOYSA-N 3-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]propane-1,2-diol Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCC(O)CO)=C1 GGOIZDJNKGSNQN-UHFFFAOYSA-N 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 3
- CRDAHLMJAKVTDA-UHFFFAOYSA-N 1-(7-methoxy-2-phenylquinolin-4-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(OCC(O)CNC(C)C)=CC=1C1=CC=CC=C1 CRDAHLMJAKVTDA-UHFFFAOYSA-N 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 53
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 32
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000007429 general method Methods 0.000 description 16
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- DLFBWXQGVIOCRY-UHFFFAOYSA-N 4-chloro-2-(4-methoxyphenyl)quinoline Chemical compound C1=CC(OC)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 DLFBWXQGVIOCRY-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- OVSABFHALRRNLF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-2-phenylquinoline Chemical compound C1OC1COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 OVSABFHALRRNLF-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- HXKKHQJGJAFBHI-VKHMYHEASA-N (2s)-1-aminopropan-2-ol Chemical compound C[C@H](O)CN HXKKHQJGJAFBHI-VKHMYHEASA-N 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 6
- GLVDSTVYOFXBKT-UHFFFAOYSA-N 4-chloro-2-phenylquinoline Chemical compound N=1C2=CC=CC=C2C(Cl)=CC=1C1=CC=CC=C1 GLVDSTVYOFXBKT-UHFFFAOYSA-N 0.000 description 6
- BAZSITKSXXHTNS-UHFFFAOYSA-N 4-chloro-7-methoxy-2-phenylquinoline Chemical compound N=1C2=CC(OC)=CC=C2C(Cl)=CC=1C1=CC=CC=C1 BAZSITKSXXHTNS-UHFFFAOYSA-N 0.000 description 6
- UKTYNFPTZDSBLR-UHFFFAOYSA-N 4-chloro-7-methoxyquinoline Chemical compound ClC1=CC=NC2=CC(OC)=CC=C21 UKTYNFPTZDSBLR-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 5
- DEZGFDSJNAWRSM-UHFFFAOYSA-N 4-chloro-2-(3,4-dihydro-1h-isoquinolin-2-yl)quinoline Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(Cl)=C1 DEZGFDSJNAWRSM-UHFFFAOYSA-N 0.000 description 5
- IBKWKEIVRXSSFH-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)quinoline Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 IBKWKEIVRXSSFH-UHFFFAOYSA-N 0.000 description 5
- PTDZYJPNFDIGTA-UHFFFAOYSA-N 4-chloro-2-(4-methylphenyl)quinoline Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 PTDZYJPNFDIGTA-UHFFFAOYSA-N 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LGDAXOKCIHVGNS-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yl)-1h-quinolin-4-one Chemical compound C1=C2CCCC2=CC(C2=CC(C3=CC=CC=C3N2)=O)=C1 LGDAXOKCIHVGNS-UHFFFAOYSA-N 0.000 description 4
- HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical class C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 description 4
- PBFVBGHVSMSCDU-UHFFFAOYSA-N 4-chloro-2-(3,4-dichlorophenyl)quinoline Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 PBFVBGHVSMSCDU-UHFFFAOYSA-N 0.000 description 4
- AJKZAFJJETUNKL-UHFFFAOYSA-N 4-chloro-2-(4-methoxyphenyl)-7-methylquinoline Chemical compound C1=CC(OC)=CC=C1C1=CC(Cl)=C(C=CC(C)=C2)C2=N1 AJKZAFJJETUNKL-UHFFFAOYSA-N 0.000 description 4
- 150000005653 4-chloroquinolines Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NBRYIPVCVKSBDY-UHFFFAOYSA-N 1-amino-3-[(2-phenylquinolin-4-yl)amino]propan-2-ol Chemical compound N=1C2=CC=CC=C2C(NCC(O)CN)=CC=1C1=CC=CC=C1 NBRYIPVCVKSBDY-UHFFFAOYSA-N 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PCHBNMXAFNHKRD-UHFFFAOYSA-N 4,7-dichloro-2-phenylquinoline Chemical compound N=1C2=CC(Cl)=CC=C2C(Cl)=CC=1C1=CC=CC=C1 PCHBNMXAFNHKRD-UHFFFAOYSA-N 0.000 description 3
- WYJZPPGXNYPNBS-UHFFFAOYSA-N 4-chloro-2-(3,4-dichlorophenyl)-7-methoxyquinoline Chemical compound N=1C2=CC(OC)=CC=C2C(Cl)=CC=1C1=CC=C(Cl)C(Cl)=C1 WYJZPPGXNYPNBS-UHFFFAOYSA-N 0.000 description 3
- GCONYZCKEIQWBE-UHFFFAOYSA-N 4-chloro-2-(3-chloro-4-methylphenyl)quinoline Chemical compound C1=C(Cl)C(C)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 GCONYZCKEIQWBE-UHFFFAOYSA-N 0.000 description 3
- UCSCCRFRBUMBNC-UHFFFAOYSA-N 4-chloro-2-(3-methylphenyl)quinoline Chemical compound CC1=CC=CC(C=2N=C3C=CC=CC3=C(Cl)C=2)=C1 UCSCCRFRBUMBNC-UHFFFAOYSA-N 0.000 description 3
- UOWMPESDTCKCRZ-UHFFFAOYSA-N 4-chloro-2-(4-methoxy-3-methylphenyl)quinoline Chemical compound C1=C(C)C(OC)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 UOWMPESDTCKCRZ-UHFFFAOYSA-N 0.000 description 3
- PGXSUMNDBHSJQP-UHFFFAOYSA-N 4-chloro-2-phenylquinolin-6-ol Chemical compound C1=C(Cl)C2=CC(O)=CC=C2N=C1C1=CC=CC=C1 PGXSUMNDBHSJQP-UHFFFAOYSA-N 0.000 description 3
- YDVXMZBCVQSCKN-UHFFFAOYSA-N 4-chloro-7-methoxy-2-(4-methoxyphenyl)quinoline Chemical compound C1=CC(OC)=CC=C1C1=CC(Cl)=C(C=CC(OC)=C2)C2=N1 YDVXMZBCVQSCKN-UHFFFAOYSA-N 0.000 description 3
- SKJUSEMBPAYCIS-UHFFFAOYSA-N 4-chloro-7-methoxy-2-(4-methylphenyl)quinoline Chemical compound N=1C2=CC(OC)=CC=C2C(Cl)=CC=1C1=CC=C(C)C=C1 SKJUSEMBPAYCIS-UHFFFAOYSA-N 0.000 description 3
- MEBFVLBGIOGSTK-UHFFFAOYSA-N 4-chloro-7-methyl-2-(4-methylphenyl)quinoline Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=C(C=CC(C)=C2)C2=N1 MEBFVLBGIOGSTK-UHFFFAOYSA-N 0.000 description 3
- RZWXKIREBJOMAK-UHFFFAOYSA-N 4-chloro-7-methyl-2-phenylquinoline Chemical compound N=1C2=CC(C)=CC=C2C(Cl)=CC=1C1=CC=CC=C1 RZWXKIREBJOMAK-UHFFFAOYSA-N 0.000 description 3
- SLBWENCMEQRYEG-UHFFFAOYSA-N 4-chloro-7-methylquinoline Chemical compound ClC1=CC=NC2=CC(C)=CC=C21 SLBWENCMEQRYEG-UHFFFAOYSA-N 0.000 description 3
- YCHPHWONKDEUAB-UHFFFAOYSA-N 4-chloro-8-methoxy-2-phenylquinoline Chemical compound N1=C2C(OC)=CC=CC2=C(Cl)C=C1C1=CC=CC=C1 YCHPHWONKDEUAB-UHFFFAOYSA-N 0.000 description 3
- WHFKEBBQPCDRND-UHFFFAOYSA-N 4-chloroquinolin-2-amine Chemical compound C1=CC=CC2=NC(N)=CC(Cl)=C21 WHFKEBBQPCDRND-UHFFFAOYSA-N 0.000 description 3
- LVFPUONZZHIVEZ-UHFFFAOYSA-N 7-methoxy-4-(oxiran-2-ylmethoxy)-2-phenylquinoline Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC(OC)=CC=C2C=1OCC1CO1 LVFPUONZZHIVEZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 101100364301 Schizosaccharomyces pombe (strain 972 / ATCC 24843) rsv1 gene Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- NDGORELJNZRQMI-UHFFFAOYSA-N (3-methyl-2-phenyl-1,3-oxazolidin-5-yl)methanol Chemical compound CN1CC(CO)OC1C1=CC=CC=C1 NDGORELJNZRQMI-UHFFFAOYSA-N 0.000 description 2
- JHHZLHWJQPUNKB-SCSAIBSYSA-N (3r)-pyrrolidin-3-ol Chemical compound O[C@@H]1CCNC1 JHHZLHWJQPUNKB-SCSAIBSYSA-N 0.000 description 2
- GBZFILBGEYHYAE-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2CC(C(=O)Cl)CCC2=C1 GBZFILBGEYHYAE-UHFFFAOYSA-N 0.000 description 2
- NADPFZNWCQIJJW-UHFFFAOYSA-N 1,2-dichloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1Cl NADPFZNWCQIJJW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QIDAFVGPTLOALB-UHFFFAOYSA-N 1-amino-3-(dimethylamino)propan-2-ol Chemical compound CN(C)CC(O)CN QIDAFVGPTLOALB-UHFFFAOYSA-N 0.000 description 2
- VOQTZJYNVJFIJW-UHFFFAOYSA-N 1-amino-3-piperidin-1-ylpropan-2-ol Chemical compound NCC(O)CN1CCCCC1 VOQTZJYNVJFIJW-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
- QNBJYUUUYZVIJP-UHFFFAOYSA-N 2,4-dichloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC(Cl)=C21 QNBJYUUUYZVIJP-UHFFFAOYSA-N 0.000 description 2
- DROXNHBXUPXQEI-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-chloroquinoline Chemical compound C1=CC=C2OC(C=3C=C(C4=CC=CC=C4N=3)Cl)=CC2=C1 DROXNHBXUPXQEI-UHFFFAOYSA-N 0.000 description 2
- YKUDSEKRLNZNTN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1h-quinolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=CC=CC=C2N1 YKUDSEKRLNZNTN-UHFFFAOYSA-N 0.000 description 2
- NVCGFYHQUFDVMO-UHFFFAOYSA-N 2-(4-methylphenyl)-1h-quinolin-4-one Chemical compound C1=CC(C)=CC=C1C1=CC(=O)C2=CC=CC=C2N1 NVCGFYHQUFDVMO-UHFFFAOYSA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- PUNLRQSULOEJRZ-UHFFFAOYSA-N 2-chloro-4-(3,4-dihydro-1h-isoquinolin-2-yl)quinoline Chemical compound C1=CC=CC2=NC(Cl)=CC(N3CC4=CC=CC=C4CC3)=C21 PUNLRQSULOEJRZ-UHFFFAOYSA-N 0.000 description 2
- JGABMVVOXLQCKZ-UHFFFAOYSA-N 2-phenyl-1h-quinolin-4-one Chemical compound N=1C2=CC=CC=C2C(O)=CC=1C1=CC=CC=C1 JGABMVVOXLQCKZ-UHFFFAOYSA-N 0.000 description 2
- RXVRHCKOPYAVCI-UHFFFAOYSA-N 3-[(6-nitro-2-phenylquinolin-4-yl)amino]propane-1,2-diol;hydrochloride Chemical compound Cl.N=1C2=CC=C([N+]([O-])=O)C=C2C(NCC(O)CO)=CC=1C1=CC=CC=C1 RXVRHCKOPYAVCI-UHFFFAOYSA-N 0.000 description 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
- UDLRGQOHGYWLCS-UHFFFAOYSA-N 4-bromo-1-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Br)C=C1C UDLRGQOHGYWLCS-UHFFFAOYSA-N 0.000 description 2
- FPIQNBOUYZLESW-UHFFFAOYSA-N 4-bromo-2-chloro-1-methoxybenzene Chemical compound COC1=CC=C(Br)C=C1Cl FPIQNBOUYZLESW-UHFFFAOYSA-N 0.000 description 2
- AFKIVQRKJQDCKH-UHFFFAOYSA-N 4-chloro-2-(3,4-dihydro-2h-chromen-6-yl)quinoline Chemical compound O1CCCC2=CC(C=3C=C(C4=CC=CC=C4N=3)Cl)=CC=C21 AFKIVQRKJQDCKH-UHFFFAOYSA-N 0.000 description 2
- YXCJZLGFRQARSS-UHFFFAOYSA-N 4-chloro-2-(3,4-dimethylphenyl)quinoline Chemical compound C1=C(C)C(C)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 YXCJZLGFRQARSS-UHFFFAOYSA-N 0.000 description 2
- CTCHZYWDILPYNO-UHFFFAOYSA-N 4-chloro-2-(3-chloro-4-methoxyphenyl)quinoline Chemical compound C1=C(Cl)C(OC)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 CTCHZYWDILPYNO-UHFFFAOYSA-N 0.000 description 2
- IZHIWNXLIZRTII-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)-7-methoxyquinoline Chemical compound N=1C2=CC(OC)=CC=C2C(Cl)=CC=1C1=CC=C(Cl)C=C1 IZHIWNXLIZRTII-UHFFFAOYSA-N 0.000 description 2
- XADFIGOIKFUDDJ-UHFFFAOYSA-N 4-chloro-2-(5,6,7,8-tetrahydronaphthalen-2-yl)quinoline Chemical compound C1CCCC2=CC(C=3C=C(C4=CC=CC=C4N=3)Cl)=CC=C21 XADFIGOIKFUDDJ-UHFFFAOYSA-N 0.000 description 2
- BUHAFKVIZOHVJG-ZHACJKMWSA-N 4-chloro-2-[(e)-2-phenylethenyl]quinoline Chemical compound N=1C2=CC=CC=C2C(Cl)=CC=1\C=C\C1=CC=CC=C1 BUHAFKVIZOHVJG-ZHACJKMWSA-N 0.000 description 2
- BBUGKMLYBHHBET-UHFFFAOYSA-N 4-chloro-2-[4-(trifluoromethyl)phenyl]quinoline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 BBUGKMLYBHHBET-UHFFFAOYSA-N 0.000 description 2
- HSHAMDJWVQMNPD-UHFFFAOYSA-N 4-chloro-2-naphthalen-2-ylquinoline Chemical compound C1=CC=CC2=CC(C=3C=C(C4=CC=CC=C4N=3)Cl)=CC=C21 HSHAMDJWVQMNPD-UHFFFAOYSA-N 0.000 description 2
- VJNMZGNHJHTTAY-UHFFFAOYSA-N 4-chloro-2-phenylquinolin-7-ol Chemical compound N=1C2=CC(O)=CC=C2C(Cl)=CC=1C1=CC=CC=C1 VJNMZGNHJHTTAY-UHFFFAOYSA-N 0.000 description 2
- QNGGBZPZQMGCGM-UHFFFAOYSA-N 4-chloro-2-thiophen-3-ylquinoline Chemical compound N=1C2=CC=CC=C2C(Cl)=CC=1C=1C=CSC=1 QNGGBZPZQMGCGM-UHFFFAOYSA-N 0.000 description 2
- JUDKYVTYOZVODY-UHFFFAOYSA-N 4-chloro-6-methoxy-2-phenylquinoline Chemical compound C1=C(Cl)C2=CC(OC)=CC=C2N=C1C1=CC=CC=C1 JUDKYVTYOZVODY-UHFFFAOYSA-N 0.000 description 2
- FIHGQXXSZUZTOF-UHFFFAOYSA-N 4-chloro-6-nitro-2-phenylquinoline Chemical compound C1=C(Cl)C2=CC([N+](=O)[O-])=CC=C2N=C1C1=CC=CC=C1 FIHGQXXSZUZTOF-UHFFFAOYSA-N 0.000 description 2
- KICNWZGIWHDCDO-UHFFFAOYSA-N 5-[[[2-(4-methoxyphenyl)quinolin-4-yl]amino]methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC(NCC2OC(=O)NC2)=C(C=CC=C2)C2=N1 KICNWZGIWHDCDO-UHFFFAOYSA-N 0.000 description 2
- BSLVNOLUEJOXMR-UHFFFAOYSA-N 5-iodo-2,3-dihydro-1-benzofuran Chemical compound IC1=CC=C2OCCC2=C1 BSLVNOLUEJOXMR-UHFFFAOYSA-N 0.000 description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
- KPFDABVKWKOIME-UHFFFAOYSA-N 6-bromo-3,4-dihydro-2h-chromene Chemical compound O1CCCC2=CC(Br)=CC=C21 KPFDABVKWKOIME-UHFFFAOYSA-N 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241001664469 Tibicina haematodes Species 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 230000021617 central nervous system development Effects 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- MRXFPPLCDBADGB-UHFFFAOYSA-N ethyl 3-oxo-3-(1,2,3,4-tetrahydronaphthalen-2-yl)propanoate Chemical compound C1=CC=C2CC(C(=O)CC(=O)OCC)CCC2=C1 MRXFPPLCDBADGB-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 230000007996 neuronal plasticity Effects 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-BYPYZUCNSA-N (3s)-pyrrolidin-3-ol Chemical compound O[C@H]1CCNC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- HCMWPTFPUCPKQM-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2CCCC2=C1 HCMWPTFPUCPKQM-UHFFFAOYSA-N 0.000 description 1
- VEPUKHYQNXSSKV-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=CC(C(=O)C)=CC=C21 VEPUKHYQNXSSKV-UHFFFAOYSA-N 0.000 description 1
- YZFRXBPDCJWCMP-UHFFFAOYSA-N 1-(7-methoxy-2-phenylquinolin-4-yl)oxy-3-(methylamino)propan-2-ol;hydrochloride Chemical compound Cl.N=1C2=CC(OC)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=CC=C1 YZFRXBPDCJWCMP-UHFFFAOYSA-N 0.000 description 1
- MRGCOYFAWORBLE-UHFFFAOYSA-N 1-(methylamino)-3-(7-methyl-2-phenylquinolin-4-yl)oxypropan-2-ol;hydrochloride Chemical compound Cl.N=1C2=CC(C)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=CC=C1 MRGCOYFAWORBLE-UHFFFAOYSA-N 0.000 description 1
- PCKBHPAVKSQTPK-UHFFFAOYSA-N 1-[(2-phenylquinolin-4-yl)amino]propan-2-ol;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(NCC(O)C)=CC=1C1=CC=CC=C1 PCKBHPAVKSQTPK-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- FHLOUPIUJOXFBJ-UHFFFAOYSA-N 1-[7-methoxy-2-(4-methoxyphenyl)quinolin-4-yl]oxy-3-(methylamino)propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(OCC(O)CNC)=CC=1C1=CC=C(OC)C=C1 FHLOUPIUJOXFBJ-UHFFFAOYSA-N 0.000 description 1
- KIETUYDSVKYOFL-UHFFFAOYSA-N 1-[[2-(4-methoxyphenyl)quinolin-4-yl]amino]-3-(methylamino)propan-2-ol;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(NCC(O)CNC)=CC=1C1=CC=C(OC)C=C1 KIETUYDSVKYOFL-UHFFFAOYSA-N 0.000 description 1
- ZGKKREYJWMDTRZ-UHFFFAOYSA-N 1-amino-3-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]propan-2-ol Chemical compound C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCC(O)CN)=C1 ZGKKREYJWMDTRZ-UHFFFAOYSA-N 0.000 description 1
- WMAHVHCZQZEWMF-UHFFFAOYSA-N 1-amino-3-[[2-(4-chlorophenyl)-7-methoxyquinolin-4-yl]amino]propan-2-ol Chemical compound N=1C2=CC(OC)=CC=C2C(NCC(O)CN)=CC=1C1=CC=C(Cl)C=C1 WMAHVHCZQZEWMF-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- KMJPEUBICDVSRJ-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydronaphthalen-2-yl)-1h-quinolin-4-one Chemical compound C1CC2=CC=CC=C2CC1C1=CC(=O)C2=CC=CC=C2N1 KMJPEUBICDVSRJ-UHFFFAOYSA-N 0.000 description 1
- NDTLCRXBNZEZPF-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)-4-chloroquinoline Chemical compound C1=CC=C2SC(C=3C=C(C4=CC=CC=C4N=3)Cl)=CC2=C1 NDTLCRXBNZEZPF-UHFFFAOYSA-N 0.000 description 1
- QKAULRVMAHGGMT-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(oxiran-2-ylmethoxy)quinoline Chemical compound C1=CC(C)=CC=C1C1=CC(OCC2OC2)=C(C=CC=C2)C2=N1 QKAULRVMAHGGMT-UHFFFAOYSA-N 0.000 description 1
- JFAKVLNGHYMAKJ-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydronaphthalen-2-yl)-1h-quinolin-4-one Chemical compound C1CCCC2=CC(C3=CC(C4=CC=CC=C4N3)=O)=CC=C21 JFAKVLNGHYMAKJ-UHFFFAOYSA-N 0.000 description 1
- AKPFVQVQPBWFEP-UHFFFAOYSA-N 2-[(2-phenylquinolin-4-yl)amino]ethanol;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(NCCO)=CC=1C1=CC=CC=C1 AKPFVQVQPBWFEP-UHFFFAOYSA-N 0.000 description 1
- HITHSBQHVMCMBT-UHFFFAOYSA-N 2-[[2-(3,4-dihydro-1h-isoquinolin-2-yl)quinolin-4-yl]amino]ethanol;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(NCCO)=C1 HITHSBQHVMCMBT-UHFFFAOYSA-N 0.000 description 1
- RCJCIFFCWMBGHU-UHFFFAOYSA-N 2-[[2-(4-methylphenyl)quinolin-4-yl]amino]ethanol;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C1=CC(NCCO)=C(C=CC=C2)C2=N1 RCJCIFFCWMBGHU-UHFFFAOYSA-N 0.000 description 1
- BZDXKAKEVDLBQF-UHFFFAOYSA-N 2-[[7-methoxy-2-(4-methylphenyl)quinolin-4-yl]amino]ethanol;hydrochloride Chemical compound Cl.N=1C2=CC(OC)=CC=C2C(NCCO)=CC=1C1=CC=C(C)C=C1 BZDXKAKEVDLBQF-UHFFFAOYSA-N 0.000 description 1
- PJYASWQMTNNSSL-UHFFFAOYSA-N 2-chloro-4-iodo-1-methylbenzene Chemical compound CC1=CC=C(I)C=C1Cl PJYASWQMTNNSSL-UHFFFAOYSA-N 0.000 description 1
- QVCRGJALYOLXDC-UHFFFAOYSA-N 2-chloroquinolin-4-amine Chemical class C1=CC=C2C(N)=CC(Cl)=NC2=C1 QVCRGJALYOLXDC-UHFFFAOYSA-N 0.000 description 1
- 150000005642 2-chloroquinolines Chemical class 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- GWUFXDHSKANUKS-UHFFFAOYSA-N 3-[(2-phenylquinolin-4-yl)amino]propane-1,2-diol;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(NCC(O)CO)=CC=1C1=CC=CC=C1 GWUFXDHSKANUKS-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- GMJCROAEROEJSA-UHFFFAOYSA-N 3-[[2-(2-phenylethyl)quinolin-4-yl]amino]propane-1,2-diol;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(NCC(O)CO)=CC=1CCC1=CC=CC=C1 GMJCROAEROEJSA-UHFFFAOYSA-N 0.000 description 1
- NHAPDLFYVGXXGK-ZHACJKMWSA-N 3-[[2-[(e)-2-phenylethenyl]quinolin-4-yl]amino]propane-1,2-diol Chemical compound N=1C2=CC=CC=C2C(NCC(O)CO)=CC=1\C=C\C1=CC=CC=C1 NHAPDLFYVGXXGK-ZHACJKMWSA-N 0.000 description 1
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MCSRZYDBKCSVHK-UHFFFAOYSA-N 4-(4-chloroquinolin-2-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 MCSRZYDBKCSVHK-UHFFFAOYSA-N 0.000 description 1
- QOGHRLGTXVMRLM-UHFFFAOYSA-N 4-bromo-1,2-dimethylbenzene Chemical group CC1=CC=C(Br)C=C1C QOGHRLGTXVMRLM-UHFFFAOYSA-N 0.000 description 1
- XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- SRVXIKUVPAOPMM-UHFFFAOYSA-N 4-chloro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)quinoline Chemical compound C1CC2=CC=CC=C2CC1C1=NC2=CC=CC=C2C(Cl)=C1 SRVXIKUVPAOPMM-UHFFFAOYSA-N 0.000 description 1
- OQPNQUYBIWRBFK-UHFFFAOYSA-N 4-chloro-2-(1,3-dihydroisoindol-2-yl)quinoline Chemical compound C1C2=CC=CC=C2CN1C1=NC2=CC=CC=C2C(Cl)=C1 OQPNQUYBIWRBFK-UHFFFAOYSA-N 0.000 description 1
- BMOXBLYDUIRUBW-UHFFFAOYSA-N 4-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)quinoline Chemical compound C1=C2OCCC2=CC(C=2C=C(C3=CC=CC=C3N=2)Cl)=C1 BMOXBLYDUIRUBW-UHFFFAOYSA-N 0.000 description 1
- MVGGSCQHEDYQIE-UHFFFAOYSA-N 4-chloro-2-(2,3-dihydro-1h-inden-5-yl)quinoline Chemical compound C1=C2CCCC2=CC(C=2C=C(C3=CC=CC=C3N=2)Cl)=C1 MVGGSCQHEDYQIE-UHFFFAOYSA-N 0.000 description 1
- HQAIROMRVBVWSK-UHFFFAOYSA-N 4-chloro-2-methylquinoline Chemical compound C1=CC=CC2=NC(C)=CC(Cl)=C21 HQAIROMRVBVWSK-UHFFFAOYSA-N 0.000 description 1
- CKTQPWIDUQGUGG-UHFFFAOYSA-N 4-chloro-6-fluoroquinoline Chemical compound N1=CC=C(Cl)C2=CC(F)=CC=C21 CKTQPWIDUQGUGG-UHFFFAOYSA-N 0.000 description 1
- BEOVBLPXVFICSP-UHFFFAOYSA-N 4-chloro-6-methoxyquinoline Chemical compound N1=CC=C(Cl)C2=CC(OC)=CC=C21 BEOVBLPXVFICSP-UHFFFAOYSA-N 0.000 description 1
- NUIMKHDPMIPYFI-UHFFFAOYSA-N 4-chloro-8-fluoroquinoline Chemical compound C1=CN=C2C(F)=CC=CC2=C1Cl NUIMKHDPMIPYFI-UHFFFAOYSA-N 0.000 description 1
- LCYDNBWXXPOMQL-UHFFFAOYSA-N 4-chloro-8-methoxyquinoline Chemical compound C1=CN=C2C(OC)=CC=CC2=C1Cl LCYDNBWXXPOMQL-UHFFFAOYSA-N 0.000 description 1
- QXNPFPJBKLAQJG-UHFFFAOYSA-N 4-chloroquinolin-6-ol Chemical compound N1=CC=C(Cl)C2=CC(O)=CC=C21 QXNPFPJBKLAQJG-UHFFFAOYSA-N 0.000 description 1
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 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
- XCGXQBSXFYIKNB-UHFFFAOYSA-N 5-[[(2-phenylquinolin-4-yl)amino]methyl]-1,3-oxazolidin-2-one Chemical compound O1C(=O)NCC1CNC1=CC(C=2C=CC=CC=2)=NC2=CC=CC=C12 XCGXQBSXFYIKNB-UHFFFAOYSA-N 0.000 description 1
- CYORHGWKIKCGTL-UHFFFAOYSA-N 5-[[[2-(4-chlorophenyl)-7-methoxyquinolin-4-yl]amino]methyl]-1,3-oxazolidin-2-one Chemical compound C=1C(C=2C=CC(Cl)=CC=2)=NC2=CC(OC)=CC=C2C=1NCC1CNC(=O)O1 CYORHGWKIKCGTL-UHFFFAOYSA-N 0.000 description 1
- QTBATKXDYFVWDJ-UHFFFAOYSA-N 5-[[[7-methoxy-2-(4-methylphenyl)quinolin-4-yl]amino]methyl]-1,3-oxazolidin-2-one Chemical compound C=1C(C=2C=CC(C)=CC=2)=NC2=CC(OC)=CC=C2C=1NCC1CNC(=O)O1 QTBATKXDYFVWDJ-UHFFFAOYSA-N 0.000 description 1
- YKZPWHOKZPODTO-UHFFFAOYSA-N 6-fluoro-2-phenyl-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(F)=CC=C2NC=1C1=CC=CC=C1 YKZPWHOKZPODTO-UHFFFAOYSA-N 0.000 description 1
- PEULGLADSYTCSB-UHFFFAOYSA-N 6-fluoro-4-(oxiran-2-ylmethoxy)-2-phenylquinoline Chemical compound C12=CC(F)=CC=C2N=C(C=2C=CC=CC=2)C=C1OCC1CO1 PEULGLADSYTCSB-UHFFFAOYSA-N 0.000 description 1
- JZVUAOCDNFNSGQ-UHFFFAOYSA-N 7-methoxy-2-phenyl-1h-quinolin-4-one Chemical compound N=1C2=CC(OC)=CC=C2C(O)=CC=1C1=CC=CC=C1 JZVUAOCDNFNSGQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ITBOMYQKVMBJAP-UHFFFAOYSA-N 8-methoxy-2-phenyl-1h-quinolin-4-one Chemical compound COC1=CC=CC(C(C=2)=O)=C1NC=2C1=CC=CC=C1 ITBOMYQKVMBJAP-UHFFFAOYSA-N 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- HVVNJUAVDAZWCB-RXMQYKEDSA-N D-prolinol Chemical compound OC[C@H]1CCCN1 HVVNJUAVDAZWCB-RXMQYKEDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- WVZSEUPGUDIELE-HTAPYJJXSA-N Ro 25-6981 Chemical compound C([C@H](C)[C@@H](O)C=1C=CC(O)=CC=1)N(CC1)CCC1CC1=CC=CC=C1 WVZSEUPGUDIELE-HTAPYJJXSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000001767 medulla oblongata Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- HIDLBJFPRKCUNF-UHFFFAOYSA-N n-[2-hydroxy-3-[(2-phenylquinolin-4-yl)amino]propyl]-2-phenylacetamide Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1NCC(O)CNC(=O)CC1=CC=CC=C1 HIDLBJFPRKCUNF-UHFFFAOYSA-N 0.000 description 1
- JCJVCTJUFQJDSF-UHFFFAOYSA-N n-[2-hydroxy-3-[(2-phenylquinolin-4-yl)amino]propyl]-2-phenylacetamide;hydrochloride Chemical compound Cl.C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1NCC(O)CNC(=O)CC1=CC=CC=C1 JCJVCTJUFQJDSF-UHFFFAOYSA-N 0.000 description 1
- RIWPOMQRSHYWGM-UHFFFAOYSA-N n-[2-hydroxy-3-[(2-phenylquinolin-4-yl)amino]propyl]-3-phenylpropanamide Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1NCC(O)CNC(=O)CCC1=CC=CC=C1 RIWPOMQRSHYWGM-UHFFFAOYSA-N 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99119539 | 1999-10-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20004892D0 NO20004892D0 (no) | 2000-09-29 |
| NO20004892L true NO20004892L (no) | 2001-04-02 |
Family
ID=8239107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20004892A NO20004892L (no) | 1999-10-01 | 2000-09-29 | Kinolin-4-yl-derivater I |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6440995B1 (cs) |
| JP (1) | JP3523174B2 (cs) |
| KR (1) | KR100398561B1 (cs) |
| CN (1) | CN1181059C (cs) |
| AR (1) | AR025882A1 (cs) |
| AT (1) | ATE281436T1 (cs) |
| AU (1) | AU774363B2 (cs) |
| BR (1) | BR0004548A (cs) |
| CA (1) | CA2321324A1 (cs) |
| CO (1) | CO5200789A1 (cs) |
| CZ (1) | CZ20003575A3 (cs) |
| DE (1) | DE60015471T2 (cs) |
| ES (1) | ES2230017T3 (cs) |
| HR (1) | HRP20000639A2 (cs) |
| HU (1) | HUP0003861A3 (cs) |
| ID (1) | ID27525A (cs) |
| IL (1) | IL138777A0 (cs) |
| MA (1) | MA26752A1 (cs) |
| NO (1) | NO20004892L (cs) |
| NZ (1) | NZ507141A (cs) |
| PE (1) | PE20010648A1 (cs) |
| PL (1) | PL342876A1 (cs) |
| PT (1) | PT1088818E (cs) |
| SG (1) | SG164268A1 (cs) |
| TR (1) | TR200002831A2 (cs) |
| ZA (1) | ZA200005239B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6831087B2 (en) * | 2001-11-09 | 2004-12-14 | Hoffmann-La Roche Inc. | Pyridine substituted isoquinoline derivatives |
| ATE309988T1 (de) * | 2002-02-13 | 2005-12-15 | Hoffmann La Roche | Neue pyridin- und quinolin-derivate |
| EP1773343A4 (en) * | 2004-07-13 | 2009-05-13 | Glaxo Group Ltd | ANTIBACTERIAL AGENTS |
| WO2009042907A1 (en) * | 2007-09-27 | 2009-04-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| JP6527534B2 (ja) * | 2014-06-16 | 2019-06-05 | ファンダシオン パラ ラ インベスティガシオン メディカ アプリカダＦｕｎｄａｃｉｏｎ Ｐａｒａ Ｌａ Ｉｎｖｅｓｔｉｇａｓｉｏｎ Ｍｅｄｉｃａ Ａｐｌｉｃａｄａ | ヒストンメチルトランスフェラーゼ及びｄｎａメチルトランスフェラーゼの二重阻害剤としての新規化合物 |
| WO2016061280A1 (en) | 2014-10-14 | 2016-04-21 | La Jolla Institute Of Allergy & Immunology | Inhibitors of low molecular weight protein tyrosine phosphatase and uses thereof |
| KR20170074178A (ko) * | 2015-12-21 | 2017-06-29 | 제이엔씨 주식회사 | 중합성 액정 화합물, 조성물, 그 액정 중합막류 및 이들의 용도 |
| CN105646462B (zh) * | 2016-01-19 | 2019-04-05 | 河南大学 | 芸香宁碱衍生物、其制备方法及应用 |
| WO2018204176A1 (en) | 2017-05-01 | 2018-11-08 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitors of low molecular weight protein tyrosine phosphatase (lmptp) and uses thereof |
| EP4313308A1 (en) * | 2021-03-26 | 2024-02-07 | Cedilla Therapeutics, Inc. | Tead inhibitors and uses thereof |
| JP2023139414A (ja) * | 2022-03-22 | 2023-10-04 | 東レ株式会社 | フェナントロリン誘導体の製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE440008C (de) | 1924-03-29 | 1927-05-04 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Chinolinderivaten |
| US4560692A (en) | 1984-07-18 | 1985-12-24 | Hoffmann-La Roche Inc. | 4-Piperidino-2-phenylquinolines |
| GB9125515D0 (en) | 1991-11-29 | 1992-01-29 | Merck Sharp & Dohme | Therapeutic agents |
| US5441963A (en) | 1991-12-20 | 1995-08-15 | Merrell Dow Pharmaceuticals | Potentiation of NMDA antagonists |
-
2000
- 2000-09-11 US US09/658,934 patent/US6440995B1/en not_active Expired - Fee Related
- 2000-09-26 MA MA26068A patent/MA26752A1/fr unknown
- 2000-09-26 AT AT00120890T patent/ATE281436T1/de not_active IP Right Cessation
- 2000-09-26 PT PT00120890T patent/PT1088818E/pt unknown
- 2000-09-26 DE DE60015471T patent/DE60015471T2/de not_active Expired - Fee Related
- 2000-09-26 NZ NZ507141A patent/NZ507141A/en unknown
- 2000-09-26 ES ES00120890T patent/ES2230017T3/es not_active Expired - Lifetime
- 2000-09-27 CA CA002321324A patent/CA2321324A1/en not_active Abandoned
- 2000-09-27 CO CO00073351A patent/CO5200789A1/es not_active Application Discontinuation
- 2000-09-27 SG SG200005551-7A patent/SG164268A1/en unknown
- 2000-09-27 CZ CZ20003575A patent/CZ20003575A3/cs unknown
- 2000-09-27 AU AU61324/00A patent/AU774363B2/en not_active Ceased
- 2000-09-28 CN CNB001292013A patent/CN1181059C/zh not_active Expired - Fee Related
- 2000-09-28 ZA ZA200005239A patent/ZA200005239B/xx unknown
- 2000-09-28 HR HR20000639A patent/HRP20000639A2/hr not_active Application Discontinuation
- 2000-09-28 PE PE2000001024A patent/PE20010648A1/es not_active Application Discontinuation
- 2000-09-28 AR ARP000105102A patent/AR025882A1/es not_active Application Discontinuation
- 2000-09-28 IL IL13877700A patent/IL138777A0/xx unknown
- 2000-09-29 PL PL00342876A patent/PL342876A1/xx not_active Application Discontinuation
- 2000-09-29 ID IDP20000849D patent/ID27525A/id unknown
- 2000-09-29 NO NO20004892A patent/NO20004892L/no unknown
- 2000-09-29 BR BR0004548-9A patent/BR0004548A/pt not_active IP Right Cessation
- 2000-09-29 HU HU0003861A patent/HUP0003861A3/hu unknown
- 2000-09-29 KR KR10-2000-0057259A patent/KR100398561B1/ko not_active Expired - Fee Related
- 2000-09-29 JP JP2000298078A patent/JP3523174B2/ja not_active Expired - Fee Related
- 2000-09-29 TR TR2000/02831A patent/TR200002831A2/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR200002831A3 (tr) | 2001-04-20 |
| ES2230017T3 (es) | 2005-05-01 |
| DE60015471T2 (de) | 2005-10-27 |
| CN1290698A (zh) | 2001-04-11 |
| CA2321324A1 (en) | 2001-04-01 |
| JP2001097952A (ja) | 2001-04-10 |
| JP3523174B2 (ja) | 2004-04-26 |
| AU6132400A (en) | 2001-04-05 |
| PL342876A1 (en) | 2001-04-09 |
| DE60015471D1 (de) | 2004-12-09 |
| PT1088818E (pt) | 2005-03-31 |
| HU0003861D0 (en) | 2000-12-28 |
| US6440995B1 (en) | 2002-08-27 |
| CN1181059C (zh) | 2004-12-22 |
| MA26752A1 (fr) | 2004-12-20 |
| CZ20003575A3 (cs) | 2001-11-14 |
| HUP0003861A3 (en) | 2002-09-30 |
| PE20010648A1 (es) | 2001-06-13 |
| ATE281436T1 (de) | 2004-11-15 |
| NZ507141A (en) | 2002-05-31 |
| NO20004892D0 (no) | 2000-09-29 |
| ZA200005239B (en) | 2001-04-16 |
| SG164268A1 (en) | 2010-09-29 |
| HRP20000639A2 (en) | 2001-06-30 |
| IL138777A0 (en) | 2001-10-31 |
| HUP0003861A2 (hu) | 2001-10-28 |
| ID27525A (id) | 2001-04-12 |
| TR200002831A2 (tr) | 2001-04-20 |
| BR0004548A (pt) | 2001-05-29 |
| KR20010050738A (ko) | 2001-06-15 |
| KR100398561B1 (ko) | 2003-09-19 |
| AR025882A1 (es) | 2002-12-18 |
| AU774363B2 (en) | 2004-06-24 |
| CO5200789A1 (es) | 2002-09-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6288068B1 (en) | Muscarinic antagonists | |
| FI94413C (fi) | Menetelmä valmistaa terapeuttisesti aktiivisia 2-(1-piperatsinyyli)-4-fenyylisykloalkanopyridiinijohdannaisia | |
| JP5932779B2 (ja) | シグマ受容体阻害剤としてのピラゾール化合物 | |
| JPH02191256A (ja) | カルボスチリル誘導体及び該誘導体を含有する精神分裂病治療剤 | |
| JPS59219260A (ja) | 新規なナフタレン−およびアザナフタレン−カルボキサミド誘導体、それを含有する製薬学的組成物、並びにそれらの製造法 | |
| CA2400657A1 (en) | Derivatives of quinoline as alpha-2 antagonists | |
| NO20004892L (no) | Kinolin-4-yl-derivater I | |
| SK280812B6 (sk) | 1,3-substituované cykloalkány a 1,3-substituované cykloalkény, spôsoby ich prípravy a farmaceutické prípravky na ich báze | |
| EP1088818B1 (en) | Quinolin-4-yl derivatives | |
| FI85266B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,4-disubstituerade piperazinderivat. | |
| JP3385318B2 (ja) | キノリン−４−イル誘導体ｉｉ | |
| HU211307A9 (en) | Tropolone derivatives and pharmaceutical composition thereof for preventing and treating ischemic diseases | |
| NO155137B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive derivater av 2-(4-piperidyl)-1-(4-kinolyl)-etanon. | |
| US5756517A (en) | Use of bisquinoline compounds in the treatment of cerebral disorders | |
| MXPA00009584A (en) | Quinolin-4-yl derivatives | |
| US6441175B1 (en) | 1-(N'-arylalkylaminoalkyl)aminoisoquinolines: a new class of dopamine receptor subtype | |
| JPH07165720A (ja) | カルボスチリル誘導体及び該誘導体を含有する精神分裂病治療剤 | |
| US20010046991A1 (en) | Derivatives of quinoline as alpha-2 antagonists | |
| CZ20003630A3 (cs) | 4-Chinolinové deriváty | |
| JPH07304740A (ja) | カルボスチリル誘導体 | |
| JPH07304741A (ja) | カルボスチリル誘導体及び該誘導体を含有する精神分裂病治療剤 | |
| JP2008524274A (ja) | テトラリン及びインダン誘導体、並びにそれらの使用 |