NO327697B1 - Dihydrobenzodiazepin-2-onderivater, farmasoytisk medikament omfattende slike, fremgangsmate for fremstilling av slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdom - Google Patents
Dihydrobenzodiazepin-2-onderivater, farmasoytisk medikament omfattende slike, fremgangsmate for fremstilling av slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdom Download PDFInfo
- Publication number
- NO327697B1 NO327697B1 NO20043237A NO20043237A NO327697B1 NO 327697 B1 NO327697 B1 NO 327697B1 NO 20043237 A NO20043237 A NO 20043237A NO 20043237 A NO20043237 A NO 20043237A NO 327697 B1 NO327697 B1 NO 327697B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- mmol
- methyl
- butyl ester
- trifluoromethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 812
- 238000002360 preparation method Methods 0.000 title claims description 23
- 239000003814 drug Substances 0.000 title claims description 12
- 229940079593 drug Drugs 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 3
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 716
- -1 -NR'R" Chemical group 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000003282 alkyl amino group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 10
- AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- QDKZHQGXPVFLHU-UHFFFAOYSA-N 1,5-benzodiazepin-2-one Chemical compound O=C1C=CN=C2C=CC=CC2=N1 QDKZHQGXPVFLHU-UHFFFAOYSA-N 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- XFCBAUSXXGLTIP-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 XFCBAUSXXGLTIP-UHFFFAOYSA-N 0.000 claims description 3
- HXTQTHUBKDBECJ-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 HXTQTHUBKDBECJ-UHFFFAOYSA-N 0.000 claims description 3
- ZTMGYWMZJBHXBD-UHFFFAOYSA-N 7-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 ZTMGYWMZJBHXBD-UHFFFAOYSA-N 0.000 claims description 3
- RRJHUDLALLDKRL-UHFFFAOYSA-N 8-chloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-methyl-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C)C=C3N=2)=C1 RRJHUDLALLDKRL-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 206010027175 memory impairment Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- NBKPYZLFZCYJJE-UHFFFAOYSA-N 4-(3-pyridin-4-ylphenyl)-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 NBKPYZLFZCYJJE-UHFFFAOYSA-N 0.000 claims description 2
- JYTRCRINABXASK-UHFFFAOYSA-N 4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 JYTRCRINABXASK-UHFFFAOYSA-N 0.000 claims description 2
- GGCAJGPNBPIIQA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethoxy-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 GGCAJGPNBPIIQA-UHFFFAOYSA-N 0.000 claims description 2
- CLEXCUYVRGOQCW-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-methyl-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(C)=C(C=C3N=2)C(F)(F)F)=C1 CLEXCUYVRGOQCW-UHFFFAOYSA-N 0.000 claims description 2
- AFSJGBXRHLXBHV-UHFFFAOYSA-N 4-[3-(2-ethyl-6-methylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 AFSJGBXRHLXBHV-UHFFFAOYSA-N 0.000 claims description 2
- CHTAULFZQPVWNJ-UHFFFAOYSA-N 4-[3-(2-ethylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 CHTAULFZQPVWNJ-UHFFFAOYSA-N 0.000 claims description 2
- XRLZWRIHQVVACZ-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(OC(F)(F)F)=CC=C3N=2)=C1 XRLZWRIHQVVACZ-UHFFFAOYSA-N 0.000 claims description 2
- DFWDFOZNVALGES-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=C1 DFWDFOZNVALGES-UHFFFAOYSA-N 0.000 claims description 2
- PBXFRAFAGCEVSF-UHFFFAOYSA-N 4-[3-(6-cyclopropylpyridin-3-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C(C=N1)=CC=C1C1CC1 PBXFRAFAGCEVSF-UHFFFAOYSA-N 0.000 claims description 2
- MTRZSMDLMJKFMC-UHFFFAOYSA-N 4-[3-(6-methylpyrimidin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=N1 MTRZSMDLMJKFMC-UHFFFAOYSA-N 0.000 claims description 2
- XUPVYWSSTOVIOJ-UHFFFAOYSA-N 4-[3-[2-(hydroxymethyl)pyridin-4-yl]phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(CO)=C1 XUPVYWSSTOVIOJ-UHFFFAOYSA-N 0.000 claims description 2
- CUBHTWLIWFXCKK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 CUBHTWLIWFXCKK-UHFFFAOYSA-N 0.000 claims description 2
- VMEZSFFCHLCBBK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 VMEZSFFCHLCBBK-UHFFFAOYSA-N 0.000 claims description 2
- CCOJJDFNFUBNKN-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 CCOJJDFNFUBNKN-UHFFFAOYSA-N 0.000 claims description 2
- GXQISOFEZQYHPI-UHFFFAOYSA-N 7-[methyl(propyl)amino]-4-(3-pyrazin-2-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)CCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 GXQISOFEZQYHPI-UHFFFAOYSA-N 0.000 claims description 2
- OPUCFSUMZCYZKN-UHFFFAOYSA-N 7-chloro-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(C(F)(F)F)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 OPUCFSUMZCYZKN-UHFFFAOYSA-N 0.000 claims description 2
- QFBDRSIFOKYSDY-UHFFFAOYSA-N 7-ethoxy-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QFBDRSIFOKYSDY-UHFFFAOYSA-N 0.000 claims description 2
- QCDLBZFFNJYTAV-UHFFFAOYSA-N 7-ethyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 QCDLBZFFNJYTAV-UHFFFAOYSA-N 0.000 claims description 2
- BUKFBCKSABZLLT-UHFFFAOYSA-N 7-methyl-4-(2-pyridin-3-ylpyridin-4-yl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=NC=1C1=CC=CN=C1 BUKFBCKSABZLLT-UHFFFAOYSA-N 0.000 claims description 2
- JNFNUQBEVWFFJC-UHFFFAOYSA-N 7-methyl-4-(3-pyrazin-2-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 JNFNUQBEVWFFJC-UHFFFAOYSA-N 0.000 claims description 2
- OQTSPIQICMTNOL-UHFFFAOYSA-N 7-methyl-4-(3-pyridazin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 OQTSPIQICMTNOL-UHFFFAOYSA-N 0.000 claims description 2
- WLGXHFREMLNUDH-UHFFFAOYSA-N 7-methyl-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 WLGXHFREMLNUDH-UHFFFAOYSA-N 0.000 claims description 2
- ZYGZDPKEZBLAHD-UHFFFAOYSA-N 7-methyl-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 ZYGZDPKEZBLAHD-UHFFFAOYSA-N 0.000 claims description 2
- IWRBJKPPNKZIAC-UHFFFAOYSA-N 7-methyl-4-[2-(2-methylpyridin-4-yl)pyridin-4-yl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2N=CC=C(C=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 IWRBJKPPNKZIAC-UHFFFAOYSA-N 0.000 claims description 2
- NZWUYDARLBVUAZ-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=CC=3)C2=C1 NZWUYDARLBVUAZ-UHFFFAOYSA-N 0.000 claims description 2
- DEOUQGPUEWWMNC-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=CN=CC=3)C2=C1 DEOUQGPUEWWMNC-UHFFFAOYSA-N 0.000 claims description 2
- VBTRNVBPGJSEAM-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyrimidin-5-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=NC=3)C2=C1 VBTRNVBPGJSEAM-UHFFFAOYSA-N 0.000 claims description 2
- QHWRKFWOOXWYMW-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[3-(2-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C(=CC=CC=2)F)=C1 QHWRKFWOOXWYMW-UHFFFAOYSA-N 0.000 claims description 2
- JLXAVOQTRVUYKG-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 JLXAVOQTRVUYKG-UHFFFAOYSA-N 0.000 claims description 2
- VOUQMUWKUYFRJK-UHFFFAOYSA-N 8-chloro-4-[3-(6-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 VOUQMUWKUYFRJK-UHFFFAOYSA-N 0.000 claims description 2
- HRSCABPISYBZJE-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyrazin-2-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 HRSCABPISYBZJE-UHFFFAOYSA-N 0.000 claims description 2
- ITPMBZMJFFOBBB-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyridazin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 ITPMBZMJFFOBBB-UHFFFAOYSA-N 0.000 claims description 2
- CWZIXKLALYDKHJ-UHFFFAOYSA-N 8-chloro-7-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C)C=C3N=2)=C1 CWZIXKLALYDKHJ-UHFFFAOYSA-N 0.000 claims description 2
- YJSYRZKLIDMQGG-UHFFFAOYSA-N 8-fluoro-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(F)=CC=C3N=2)=C1 YJSYRZKLIDMQGG-UHFFFAOYSA-N 0.000 claims description 2
- YYEKPNNSPXLPJC-UHFFFAOYSA-N 8-methyl-4-(3-pyridin-3-ylphenyl)-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(C(F)(F)F)C(C)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 YYEKPNNSPXLPJC-UHFFFAOYSA-N 0.000 claims description 2
- QRDOMCFVXRYHRK-UHFFFAOYSA-N 8-methyl-4-(3-pyridin-4-ylphenyl)-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(C(F)(F)F)C(C)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 QRDOMCFVXRYHRK-UHFFFAOYSA-N 0.000 claims description 2
- YCFKJJCPSFWCPF-UHFFFAOYSA-N 8-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(C)=C(C=C3N=2)C(F)(F)F)=C1 YCFKJJCPSFWCPF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- LYTVXCQQTLUEQR-UHFFFAOYSA-N ro4491533 Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 LYTVXCQQTLUEQR-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 9
- UVNQIBJKZJJBQK-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 UVNQIBJKZJJBQK-UHFFFAOYSA-N 0.000 claims 1
- PQWNWLVSPGJPAF-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=C1 PQWNWLVSPGJPAF-UHFFFAOYSA-N 0.000 claims 1
- CMLVJJVYIVBZNH-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 CMLVJJVYIVBZNH-UHFFFAOYSA-N 0.000 claims 1
- AHDAHZZDQMCLJT-UHFFFAOYSA-N 7-chloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(Cl)C=C3N=2)C(F)(F)F)=C1 AHDAHZZDQMCLJT-UHFFFAOYSA-N 0.000 claims 1
- LKVQKLAWCNGKSL-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C(=CC=CC=2)F)=C1 LKVQKLAWCNGKSL-UHFFFAOYSA-N 0.000 claims 1
- QWFYXUVFCJKYON-UHFFFAOYSA-N 8-chloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(Cl)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QWFYXUVFCJKYON-UHFFFAOYSA-N 0.000 claims 1
- ODSWASRHKDESDR-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 ODSWASRHKDESDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 101150115538 nero gene Proteins 0.000 claims 1
- 239000007787 solid Substances 0.000 description 400
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 286
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 252
- 239000000203 mixture Substances 0.000 description 125
- 239000000460 chlorine Substances 0.000 description 118
- 239000006260 foam Substances 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 104
- 235000019439 ethyl acetate Nutrition 0.000 description 103
- 239000003921 oil Substances 0.000 description 94
- 235000019198 oils Nutrition 0.000 description 94
- 239000000243 solution Substances 0.000 description 94
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- WSUXSDFUECNYSX-UHFFFAOYSA-N tert-butyl n-[2-amino-5-methyl-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F WSUXSDFUECNYSX-UHFFFAOYSA-N 0.000 description 78
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 74
- VTSJYKYERZLMEK-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1N VTSJYKYERZLMEK-UHFFFAOYSA-N 0.000 description 73
- RENOIBALUBTYLS-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 RENOIBALUBTYLS-UHFFFAOYSA-N 0.000 description 68
- AEHYHZHQKIYWHR-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyridin-3-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 AEHYHZHQKIYWHR-UHFFFAOYSA-N 0.000 description 67
- SAHCRZHMDWJEMU-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1N SAHCRZHMDWJEMU-UHFFFAOYSA-N 0.000 description 62
- 239000002904 solvent Substances 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 239000000126 substance Substances 0.000 description 54
- UXKVDHBWXZINNK-UHFFFAOYSA-N tert-butyl n-[2-amino-5-ethoxy-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F UXKVDHBWXZINNK-UHFFFAOYSA-N 0.000 description 54
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 52
- HYTGYTLUYPRXTL-UHFFFAOYSA-N tert-butyl 3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 HYTGYTLUYPRXTL-UHFFFAOYSA-N 0.000 description 52
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 239000012267 brine Substances 0.000 description 50
- 239000011734 sodium Substances 0.000 description 50
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 50
- 229920006395 saturated elastomer Polymers 0.000 description 47
- LGAJSDWFYQMSMX-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyridin-4-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 LGAJSDWFYQMSMX-UHFFFAOYSA-N 0.000 description 44
- JNOTVBKCTMWNCH-UHFFFAOYSA-N tert-butyl n-(2-amino-4-chloro-5-methylphenyl)carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1Cl JNOTVBKCTMWNCH-UHFFFAOYSA-N 0.000 description 44
- 238000010898 silica gel chromatography Methods 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 38
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 37
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 34
- MEGIEGFVRNXYSU-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(dimethylamino)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CN(C)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F MEGIEGFVRNXYSU-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 238000005984 hydrogenation reaction Methods 0.000 description 31
- AEYBBZRWQPBSDJ-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyridin-2-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 AEYBBZRWQPBSDJ-UHFFFAOYSA-N 0.000 description 31
- ZTCGGBIFOFASKI-UHFFFAOYSA-N tert-butyl acetate;lithium Chemical compound [Li].CC(=O)OC(C)(C)C ZTCGGBIFOFASKI-UHFFFAOYSA-N 0.000 description 31
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- KXLAIFIPGIZAJM-UHFFFAOYSA-N tert-butyl n-[2-amino-5-chloro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(C(F)(F)F)C=C1N KXLAIFIPGIZAJM-UHFFFAOYSA-N 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000012043 crude product Substances 0.000 description 26
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- FVZIFCWZBOPYIS-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyrazin-2-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 FVZIFCWZBOPYIS-UHFFFAOYSA-N 0.000 description 26
- 229910001868 water Inorganic materials 0.000 description 25
- MHOIZXNWGRDLBM-UHFFFAOYSA-N tert-butyl 3-[3-[2-(oxan-2-yloxymethyl)pyridin-4-yl]phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(COC3OCCCC3)N=CC=2)=C1 MHOIZXNWGRDLBM-UHFFFAOYSA-N 0.000 description 23
- 230000007062 hydrolysis Effects 0.000 description 22
- 238000006460 hydrolysis reaction Methods 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 22
- VXDQRQWDMCRSRI-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 VXDQRQWDMCRSRI-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- RXHRIUDEGZJSQX-UHFFFAOYSA-N tert-butyl 3-[3-(6-cyclopropylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NC(=CC=2)C2CC2)=C1 RXHRIUDEGZJSQX-UHFFFAOYSA-N 0.000 description 21
- VNHPYPILBWQVTL-UHFFFAOYSA-N tert-butyl 3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 VNHPYPILBWQVTL-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 20
- 150000003751 zinc Chemical class 0.000 description 20
- 230000009467 reduction Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 235000019502 Orange oil Nutrition 0.000 description 18
- 239000010502 orange oil Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- RAAXZOKVGWKKCP-UHFFFAOYSA-N tert-butyl n-(2-amino-4-chlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)C=C1N RAAXZOKVGWKKCP-UHFFFAOYSA-N 0.000 description 17
- 150000004702 methyl esters Chemical class 0.000 description 16
- LIZHORPIFTUBCO-UHFFFAOYSA-N tert-butyl n-[2-amino-4-chloro-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1N LIZHORPIFTUBCO-UHFFFAOYSA-N 0.000 description 16
- KYHFBBURZMZTII-UHFFFAOYSA-N tert-butyl n-[2-amino-4-methyl-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CC(N)=C(NC(=O)OC(C)(C)C)C=C1C(F)(F)F KYHFBBURZMZTII-UHFFFAOYSA-N 0.000 description 16
- 238000010626 work up procedure Methods 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000008096 xylene Substances 0.000 description 15
- AAMCWLIPRMIPBN-UHFFFAOYSA-N 5-chloro-2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC(Cl)=C(C(F)(F)F)C=C1[N+]([O-])=O AAMCWLIPRMIPBN-UHFFFAOYSA-N 0.000 description 14
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- MGYGCOIPDVEYEN-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(trifluoromethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(OC(F)(F)F)C=C1N MGYGCOIPDVEYEN-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 13
- CDQRKSLMPFFDHX-UHFFFAOYSA-N tert-butyl 3-[3-(2-ethylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(CC)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 CDQRKSLMPFFDHX-UHFFFAOYSA-N 0.000 description 13
- WHHWCCNXCHLQEH-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC1=NC=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 WHHWCCNXCHLQEH-UHFFFAOYSA-N 0.000 description 13
- MGHZFNOACJPPHG-UHFFFAOYSA-N tert-butyl 3-[3-(6-methoxypyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 MGHZFNOACJPPHG-UHFFFAOYSA-N 0.000 description 13
- METWENWZQQGEMV-UHFFFAOYSA-N tert-butyl 3-[3-[2-(2-methylpropyl)pyridin-4-yl]phenyl]-3-oxopropanoate Chemical compound C1=NC(CC(C)C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 METWENWZQQGEMV-UHFFFAOYSA-N 0.000 description 13
- GLJQKVXUTVKHRW-UHFFFAOYSA-N tert-butyl 3-[3-[2-methyl-6-(oxan-2-yloxymethyl)pyridin-4-yl]phenyl]-3-oxopropanoate Chemical compound N=1C(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=CC=1COC1CCCCO1 GLJQKVXUTVKHRW-UHFFFAOYSA-N 0.000 description 13
- AJVDKRZLKICPOP-UHFFFAOYSA-N tert-butyl 3-oxo-3-[3-(2-propan-2-ylpyridin-4-yl)phenyl]propanoate Chemical compound C1=NC(C(C)C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 AJVDKRZLKICPOP-UHFFFAOYSA-N 0.000 description 13
- MLHCDZJYGMFMKX-UHFFFAOYSA-N tert-butyl n-(2-amino-5-chloro-4-methylphenyl)carbamate Chemical compound CC1=CC(N)=C(NC(=O)OC(C)(C)C)C=C1Cl MLHCDZJYGMFMKX-UHFFFAOYSA-N 0.000 description 13
- HBMYBFUHFGSHSZ-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[methyl(propyl)amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCCN(C)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F HBMYBFUHFGSHSZ-UHFFFAOYSA-N 0.000 description 13
- DBVFWZMQJQMJCB-UHFFFAOYSA-N 3-boronobenzoic acid Chemical compound OB(O)C1=CC=CC(C(O)=O)=C1 DBVFWZMQJQMJCB-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- ZDROZOXDJUOZLN-UHFFFAOYSA-N tert-butyl 3-[3-(2-cyclopropylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)C2CC2)=C1 ZDROZOXDJUOZLN-UHFFFAOYSA-N 0.000 description 12
- SENKMKTXVVCGLI-UHFFFAOYSA-N tert-butyl n-[2-amino-5-ethyl-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F SENKMKTXVVCGLI-UHFFFAOYSA-N 0.000 description 12
- HXZFITILXOESLM-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(C(F)(F)F)C=C1[N+]([O-])=O HXZFITILXOESLM-UHFFFAOYSA-N 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 11
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- WETHOPRRFHLLRM-UHFFFAOYSA-N tert-butyl 3-[3-(2,5-dimethylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1C WETHOPRRFHLLRM-UHFFFAOYSA-N 0.000 description 11
- VQHDUUJUTSWHRN-UHFFFAOYSA-N tert-butyl 3-[3-(2-cyanopyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)C#N)=C1 VQHDUUJUTSWHRN-UHFFFAOYSA-N 0.000 description 11
- IUCJRNBYAJYQPW-UHFFFAOYSA-N tert-butyl 3-[3-(6-ethylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(CC)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 IUCJRNBYAJYQPW-UHFFFAOYSA-N 0.000 description 11
- DJNZXUHFFBNUHP-UHFFFAOYSA-N tert-butyl 3-oxo-3-[3-[2-(trifluoromethyl)pyridin-4-yl]phenyl]propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)C(F)(F)F)=C1 DJNZXUHFFBNUHP-UHFFFAOYSA-N 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- IBKSOWUYKOORFF-UHFFFAOYSA-N tert-butyl n-(2-amino-4-fluorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(F)C=C1N IBKSOWUYKOORFF-UHFFFAOYSA-N 0.000 description 11
- IXVYZOXGLKDGON-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=CC=C1N IXVYZOXGLKDGON-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- IYYJHECBPYGIFD-UHFFFAOYSA-N tert-butyl 3-[3-(4-methylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC1=CC=NC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 IYYJHECBPYGIFD-UHFFFAOYSA-N 0.000 description 10
- BFXFJQSBMAHZRB-UHFFFAOYSA-N tert-butyl 3-[3-(5-ethyl-2-methylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CCC1=CN=C(C)C=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 BFXFJQSBMAHZRB-UHFFFAOYSA-N 0.000 description 10
- ULGQMAUZNANTRB-UHFFFAOYSA-N tert-butyl 3-[3-(6-cyclopropyl-4-methylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC1=CC(C2CC2)=NC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 ULGQMAUZNANTRB-UHFFFAOYSA-N 0.000 description 10
- FCIBAVBCBAXBFX-UHFFFAOYSA-N tert-butyl n-(4,5-dichloro-2-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FCIBAVBCBAXBFX-UHFFFAOYSA-N 0.000 description 10
- ARMNFOSONLJIOQ-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2-fluorophenyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC=C1C1=CC=CC=C1F ARMNFOSONLJIOQ-UHFFFAOYSA-N 0.000 description 10
- DZLQKFWFDKHKGB-UHFFFAOYSA-N tert-butyl n-[2-amino-5-propyl-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCCC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F DZLQKFWFDKHKGB-UHFFFAOYSA-N 0.000 description 10
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- VGDIFHLJEDKPRE-UHFFFAOYSA-N tert-butyl 3-[3-(2,3-dimethylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC1=NC=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1C VGDIFHLJEDKPRE-UHFFFAOYSA-N 0.000 description 9
- MDARRQPBDPVCEQ-UHFFFAOYSA-N tert-butyl 3-[3-(2-cyclopentylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)C2CCCC2)=C1 MDARRQPBDPVCEQ-UHFFFAOYSA-N 0.000 description 9
- SKBDWYZPMPDZLF-UHFFFAOYSA-N tert-butyl 3-[3-(4,6-dimethylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(C)=CC(C)=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 SKBDWYZPMPDZLF-UHFFFAOYSA-N 0.000 description 9
- XRLMKPLJDSCXIZ-UHFFFAOYSA-N tert-butyl 3-[3-(6-methylpyrazin-2-yl)phenyl]-3-oxopropanoate Chemical compound CC1=CN=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 XRLMKPLJDSCXIZ-UHFFFAOYSA-N 0.000 description 9
- MLJURMBXXADYSF-UHFFFAOYSA-N tert-butyl 3-oxo-3-[3-(2-pyrrolidin-1-ylpyridin-4-yl)phenyl]propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)N2CCCC2)=C1 MLJURMBXXADYSF-UHFFFAOYSA-N 0.000 description 9
- PONIODBBGZSVNE-UHFFFAOYSA-N tert-butyl 3-oxo-3-[3-(6-propan-2-ylpyridin-3-yl)phenyl]propanoate Chemical compound C1=NC(C(C)C)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 PONIODBBGZSVNE-UHFFFAOYSA-N 0.000 description 9
- MTNSCDUMBKPAFQ-UHFFFAOYSA-N tert-butyl n-(2-amino-5-ethoxyphenyl)carbamate Chemical compound CCOC1=CC=C(N)C(NC(=O)OC(C)(C)C)=C1 MTNSCDUMBKPAFQ-UHFFFAOYSA-N 0.000 description 9
- TYAHZMFHLGQBLK-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(2-methoxyethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound COCCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F TYAHZMFHLGQBLK-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- ITQZETDOZYFRFH-UHFFFAOYSA-N tert-butyl 3-[3-(6-methylpyridazin-3-yl)phenyl]-3-oxopropanoate Chemical compound N1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 ITQZETDOZYFRFH-UHFFFAOYSA-N 0.000 description 8
- ZDTBMFFIPXTZEB-UHFFFAOYSA-N tert-butyl n-(2-amino-4-chloro-5-fluorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(Cl)C=C1N ZDTBMFFIPXTZEB-UHFFFAOYSA-N 0.000 description 8
- APVFXEAPERLLPQ-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(cyclopropylmethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(OCC2CC2)=C1C(F)(F)F APVFXEAPERLLPQ-UHFFFAOYSA-N 0.000 description 8
- BPBNFIQORGDFRH-UHFFFAOYSA-N tert-butyl n-[2-amino-5-ethenyl-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C=C)=C(C(F)(F)F)C=C1N BPBNFIQORGDFRH-UHFFFAOYSA-N 0.000 description 8
- HIZCQCCCJZHWDD-UHFFFAOYSA-N tert-butyl n-[2-amino-5-methoxy-4-(trifluoromethyl)phenyl]carbamate Chemical compound COC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F HIZCQCCCJZHWDD-UHFFFAOYSA-N 0.000 description 8
- IDIHNUHJKRFJHR-UHFFFAOYSA-N tert-butyl n-[2-amino-5-morpholin-4-yl-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(N2CCOCC2)=C1C(F)(F)F IDIHNUHJKRFJHR-UHFFFAOYSA-N 0.000 description 8
- DNMMRDHYNSPUOV-UHFFFAOYSA-N tert-butyl n-[2-amino-5-propoxy-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F DNMMRDHYNSPUOV-UHFFFAOYSA-N 0.000 description 8
- UQOUWWYMUATNBB-UHFFFAOYSA-N tert-butyl n-[5-ethenyl-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C=C)=C(C(F)(F)F)C=C1[N+]([O-])=O UQOUWWYMUATNBB-UHFFFAOYSA-N 0.000 description 8
- IWFHBRFJOHTIPU-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Cl)C=C1N IWFHBRFJOHTIPU-UHFFFAOYSA-N 0.000 description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 235000011150 stannous chloride Nutrition 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- BXORTACACMHLNU-UHFFFAOYSA-N tert-butyl 3-[3-(2-cyclopropyl-6-methylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound N=1C(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=CC=1C1CC1 BXORTACACMHLNU-UHFFFAOYSA-N 0.000 description 7
- ORUCNVQGISYFBE-UHFFFAOYSA-N tert-butyl 3-[3-(2-cyclopropylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C(=NC=CC=2)C2CC2)=C1 ORUCNVQGISYFBE-UHFFFAOYSA-N 0.000 description 7
- TYMSKIYEAHPCAP-UHFFFAOYSA-N tert-butyl 3-[3-(2-ethyl-6-methylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC1=NC(CC)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 TYMSKIYEAHPCAP-UHFFFAOYSA-N 0.000 description 7
- ODHMZZDPQPUAKJ-UHFFFAOYSA-N tert-butyl 3-[3-(2-ethylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CCC1=NC=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 ODHMZZDPQPUAKJ-UHFFFAOYSA-N 0.000 description 7
- XHOQBRVRZSQZSL-UHFFFAOYSA-N tert-butyl 3-[3-(2-morpholin-4-ylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)N2CCOCC2)=C1 XHOQBRVRZSQZSL-UHFFFAOYSA-N 0.000 description 7
- VFGNVWPKPQNCEC-UHFFFAOYSA-N tert-butyl 3-[3-(6-ethyl-4-methylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(CC)=CC(C)=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 VFGNVWPKPQNCEC-UHFFFAOYSA-N 0.000 description 7
- YXSNRJAAMVCCRU-UHFFFAOYSA-N tert-butyl 3-oxo-3-(2-pyridin-3-ylpyridin-4-yl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=NC(C=2C=NC=CC=2)=C1 YXSNRJAAMVCCRU-UHFFFAOYSA-N 0.000 description 7
- ZCGIEZPJGKROLT-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[methyl(2-methylpropyl)amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)CN(C)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F ZCGIEZPJGKROLT-UHFFFAOYSA-N 0.000 description 7
- XMWVNQVJVMIVMK-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[methyl(propan-2-yl)amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)N(C)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F XMWVNQVJVMIVMK-UHFFFAOYSA-N 0.000 description 7
- VTVFCTSEAINUQK-UHFFFAOYSA-N tert-butyl n-[2-amino-5-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(N2CCCC2)=C1C(F)(F)F VTVFCTSEAINUQK-UHFFFAOYSA-N 0.000 description 7
- HIHLPWFEZHZXPD-UHFFFAOYSA-N tert-butyl n-[5-fluoro-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(C(F)(F)F)C=C1[N+]([O-])=O HIHLPWFEZHZXPD-UHFFFAOYSA-N 0.000 description 7
- ZVGANEZTONXZBD-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F ZVGANEZTONXZBD-UHFFFAOYSA-N 0.000 description 7
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 6
- FSGTULQLEVAYRS-UHFFFAOYSA-N 4,5-dichloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FSGTULQLEVAYRS-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 description 6
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 244000309464 bull Species 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 6
- KQSZWASOPSKBCR-UHFFFAOYSA-N tert-butyl n-(2-amino-4-chloro-5-ethoxyphenyl)carbamate Chemical compound CCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1Cl KQSZWASOPSKBCR-UHFFFAOYSA-N 0.000 description 6
- PFSKAXRHTNXDAE-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(6-methoxypyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 PFSKAXRHTNXDAE-UHFFFAOYSA-N 0.000 description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- BYIHXUHOYZDNTR-UHFFFAOYSA-M chlorozinc(1+);cyclopropane Chemical compound [Cl-].[Zn+2].C1C[CH-]1 BYIHXUHOYZDNTR-UHFFFAOYSA-M 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- VRGTZOVDXJAGQG-UHFFFAOYSA-N tert-butyl 3-[3-(2,6-dimethylpyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 VRGTZOVDXJAGQG-UHFFFAOYSA-N 0.000 description 5
- TXHPJZSOYKJQAD-UHFFFAOYSA-N tert-butyl 3-[3-(6-methoxypyridazin-3-yl)phenyl]-3-oxopropanoate Chemical compound N1=NC(OC)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 TXHPJZSOYKJQAD-UHFFFAOYSA-N 0.000 description 5
- YTIIPRKXGSCTTR-UHFFFAOYSA-N tert-butyl 3-[3-[6-(dimethylamino)pyridin-3-yl]phenyl]-3-oxopropanoate Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 YTIIPRKXGSCTTR-UHFFFAOYSA-N 0.000 description 5
- AZWHQMXHERLTQN-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyridazin-4-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NN=CC=2)=C1 AZWHQMXHERLTQN-UHFFFAOYSA-N 0.000 description 5
- JTJFEWDXNKYBOE-UHFFFAOYSA-N tert-butyl n-(2-nitrophenyl)carbamate Chemical class CC(C)(C)OC(=O)NC1=CC=CC=C1[N+]([O-])=O JTJFEWDXNKYBOE-UHFFFAOYSA-N 0.000 description 5
- YJHGAFUPACBMDJ-UHFFFAOYSA-N tert-butyl n-(4-iodo-2-nitrophenyl)carbamate Chemical class CC(C)(C)OC(=O)NC1=CC=C(I)C=C1[N+]([O-])=O YJHGAFUPACBMDJ-UHFFFAOYSA-N 0.000 description 5
- OPMLJIKDTVDKCC-UHFFFAOYSA-N tert-butyl n-[2-amino-4-chloro-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(Cl)C=C1N OPMLJIKDTVDKCC-UHFFFAOYSA-N 0.000 description 5
- KRWKPWWLGUDSOV-UHFFFAOYSA-N tert-butyl n-[2-amino-4-chloro-5-(2-methylpropylamino)phenyl]carbamate Chemical compound CC(C)CNC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1Cl KRWKPWWLGUDSOV-UHFFFAOYSA-N 0.000 description 5
- MIALJKDZAXZUGL-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-nitro-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1[N+]([O-])=O MIALJKDZAXZUGL-UHFFFAOYSA-N 0.000 description 5
- DEPKSCHPMMZBDK-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-nitro-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CC([N+]([O-])=O)=C(NC(=O)OC(C)(C)C)C=C1C(F)(F)F DEPKSCHPMMZBDK-UHFFFAOYSA-N 0.000 description 5
- NLOIEOPPMRZMCT-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 NLOIEOPPMRZMCT-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- DWJIUNKBHIJMPC-UHFFFAOYSA-N (2-bromopyridin-3-yl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CN=C1Br DWJIUNKBHIJMPC-UHFFFAOYSA-N 0.000 description 4
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 4
- WWJLJUAHQHXDGM-UHFFFAOYSA-N 2,5-dibromo-4-methylpyridine Chemical compound CC1=CC(Br)=NC=C1Br WWJLJUAHQHXDGM-UHFFFAOYSA-N 0.000 description 4
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical class COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- JFPJVTNYCURRAB-UHFFFAOYSA-N 2-nitro-n-phenylacetamide Chemical group [O-][N+](=O)CC(=O)NC1=CC=CC=C1 JFPJVTNYCURRAB-UHFFFAOYSA-N 0.000 description 4
- YSPMKEAAPAZVGI-UHFFFAOYSA-N 3-(2-chloropyridin-4-yl)benzonitrile Chemical compound C1=NC(Cl)=CC(C=2C=C(C=CC=2)C#N)=C1 YSPMKEAAPAZVGI-UHFFFAOYSA-N 0.000 description 4
- TZGSWJVPEYRVAR-UHFFFAOYSA-N 3-(3-oxobutanoyl)benzoic acid Chemical compound CC(=O)CC(=O)C1=CC=CC(C(O)=O)=C1 TZGSWJVPEYRVAR-UHFFFAOYSA-N 0.000 description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 description 4
- 208000002193 Pain Diseases 0.000 description 4
- 208000027089 Parkinsonian disease Diseases 0.000 description 4
- 206010034010 Parkinsonism Diseases 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- JKBZNTNUWKVKHT-UHFFFAOYSA-N n-[4-methyl-2-nitro-5-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC(C(F)(F)F)=C(C)C=C1[N+]([O-])=O JKBZNTNUWKVKHT-UHFFFAOYSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 150000002926 oxygen Chemical class 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000008279 sol Substances 0.000 description 4
- RUTRVXDBOSVFFT-UHFFFAOYSA-N tert-butyl n-(2-amino-4-methoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)(C)C)C(N)=C1 RUTRVXDBOSVFFT-UHFFFAOYSA-N 0.000 description 4
- XNDOVDWSIUOOET-UHFFFAOYSA-N tert-butyl n-(2-amino-4-pyrrol-1-ylphenyl)carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC=C1N1C=CC=C1 XNDOVDWSIUOOET-UHFFFAOYSA-N 0.000 description 4
- ATQQUUXZLWAIMY-UHFFFAOYSA-N tert-butyl n-(2-amino-5-methoxyphenyl)carbamate Chemical compound COC1=CC=C(N)C(NC(=O)OC(C)(C)C)=C1 ATQQUUXZLWAIMY-UHFFFAOYSA-N 0.000 description 4
- JXRYXFLIZMKRRS-UHFFFAOYSA-N tert-butyl n-(4-chloro-2-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)C=C1[N+]([O-])=O JXRYXFLIZMKRRS-UHFFFAOYSA-N 0.000 description 4
- NFSLGZQXFGFBOX-UHFFFAOYSA-N tert-butyl n-(4-chloro-5-ethoxy-2-nitrophenyl)carbamate Chemical compound CCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1Cl NFSLGZQXFGFBOX-UHFFFAOYSA-N 0.000 description 4
- UVJVHGAKMRPSSD-UHFFFAOYSA-N tert-butyl n-(4-chloro-5-fluoro-2-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(Cl)C=C1[N+]([O-])=O UVJVHGAKMRPSSD-UHFFFAOYSA-N 0.000 description 4
- XPKGICYJOWIVOQ-UHFFFAOYSA-N tert-butyl n-(4-chloro-5-methyl-2-nitrophenyl)carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1Cl XPKGICYJOWIVOQ-UHFFFAOYSA-N 0.000 description 4
- OPVVNOMDBDQRTM-UHFFFAOYSA-N tert-butyl n-(4-fluoro-2-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(F)C=C1[N+]([O-])=O OPVVNOMDBDQRTM-UHFFFAOYSA-N 0.000 description 4
- GWDPJYWKXCLFHV-UHFFFAOYSA-N tert-butyl n-(4-methoxy-2-nitrophenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)(C)C)C([N+]([O-])=O)=C1 GWDPJYWKXCLFHV-UHFFFAOYSA-N 0.000 description 4
- WDKOTVLVDWHHLW-UHFFFAOYSA-N tert-butyl n-(5-chloro-4-methyl-2-nitrophenyl)carbamate Chemical compound CC1=CC([N+]([O-])=O)=C(NC(=O)OC(C)(C)C)C=C1Cl WDKOTVLVDWHHLW-UHFFFAOYSA-N 0.000 description 4
- YVIUVNPVSMYZJR-UHFFFAOYSA-N tert-butyl n-(5-ethoxy-2-nitrophenyl)carbamate Chemical compound CCOC1=CC=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=C1 YVIUVNPVSMYZJR-UHFFFAOYSA-N 0.000 description 4
- MEALZEDUQMRXBW-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC=C1C#CC1=CC=CC=C1 MEALZEDUQMRXBW-UHFFFAOYSA-N 0.000 description 4
- WIJJMYDKODJPIW-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(dimethylamino)-4-(2-fluorophenyl)phenyl]carbamate Chemical compound CN(C)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=CC=C1F WIJJMYDKODJPIW-UHFFFAOYSA-N 0.000 description 4
- UVNIFGMHLWUQLW-UHFFFAOYSA-N tert-butyl n-[2-amino-5-cyclopropyl-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(C2CC2)=C1C(F)(F)F UVNIFGMHLWUQLW-UHFFFAOYSA-N 0.000 description 4
- YIIBSYFRWRSAFI-UHFFFAOYSA-N tert-butyl n-[2-amino-5-fluoro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(C(F)(F)F)C=C1N YIIBSYFRWRSAFI-UHFFFAOYSA-N 0.000 description 4
- RSVLHUAHSFCCPQ-UHFFFAOYSA-N tert-butyl n-[2-nitro-4-(trifluoromethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(OC(F)(F)F)C=C1[N+]([O-])=O RSVLHUAHSFCCPQ-UHFFFAOYSA-N 0.000 description 4
- PHKCNXWTVZGKLM-UHFFFAOYSA-N tert-butyl n-[2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O PHKCNXWTVZGKLM-UHFFFAOYSA-N 0.000 description 4
- QTNLFONSWIGVPC-UHFFFAOYSA-N tert-butyl n-[2-nitro-5-propoxy-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F QTNLFONSWIGVPC-UHFFFAOYSA-N 0.000 description 4
- GEGYSTYXJJPRBT-UHFFFAOYSA-N tert-butyl n-[2-nitro-5-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(N2CCCC2)=C1C(F)(F)F GEGYSTYXJJPRBT-UHFFFAOYSA-N 0.000 description 4
- NKQMESHTYIOCPN-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-(2-methylpropylamino)-2-nitrophenyl]carbamate Chemical compound CC(C)CNC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1Cl NKQMESHTYIOCPN-UHFFFAOYSA-N 0.000 description 4
- CRWZRJODVOQKTK-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-[methyl(propan-2-yl)amino]-2-nitrophenyl]carbamate Chemical compound CC(C)N(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1Cl CRWZRJODVOQKTK-UHFFFAOYSA-N 0.000 description 4
- XBYNEZWMJVZREW-UHFFFAOYSA-N tert-butyl n-[5-(2-methylpropylamino)-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)CNC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F XBYNEZWMJVZREW-UHFFFAOYSA-N 0.000 description 4
- DBSPUNGWCRETDA-UHFFFAOYSA-N tert-butyl n-[5-(cyclopropylmethoxy)-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(OCC2CC2)=C1C(F)(F)F DBSPUNGWCRETDA-UHFFFAOYSA-N 0.000 description 4
- TUVPLYLIYXHUOQ-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-4-(2-fluorophenyl)-2-nitrophenyl]carbamate Chemical compound CN(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C1=CC=CC=C1F TUVPLYLIYXHUOQ-UHFFFAOYSA-N 0.000 description 4
- OQSOMGNCWKWTNU-UHFFFAOYSA-N tert-butyl n-[5-(hydroxymethyl)-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(CO)=C(C(F)(F)F)C=C1[N+]([O-])=O OQSOMGNCWKWTNU-UHFFFAOYSA-N 0.000 description 4
- HWGMPADHNJRBSZ-UHFFFAOYSA-N tert-butyl n-[5-[methyl(2-methylpropyl)amino]-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)CN(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F HWGMPADHNJRBSZ-UHFFFAOYSA-N 0.000 description 4
- YXPWIJNJDDGHBN-UHFFFAOYSA-N tert-butyl n-[5-cyclopropyl-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(C2CC2)=C1C(F)(F)F YXPWIJNJDDGHBN-UHFFFAOYSA-N 0.000 description 4
- UVKVMHVAPYEAGG-UHFFFAOYSA-N tert-butyl n-[5-ethoxy-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC)=CC=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=CC=2)=C1 UVKVMHVAPYEAGG-UHFFFAOYSA-N 0.000 description 4
- IWYNYIRMZJXRJQ-UHFFFAOYSA-N tert-butyl n-[5-ethoxy-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F IWYNYIRMZJXRJQ-UHFFFAOYSA-N 0.000 description 4
- CCJHZEYABFTNGW-UHFFFAOYSA-N tert-butyl n-[5-morpholin-4-yl-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(N2CCOCC2)=C1C(F)(F)F CCJHZEYABFTNGW-UHFFFAOYSA-N 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 4
- 235000019798 tripotassium phosphate Nutrition 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- YBTKGKVQEXAYEM-UHFFFAOYSA-N 2-bromopyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(Br)=C1 YBTKGKVQEXAYEM-UHFFFAOYSA-N 0.000 description 3
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 3
- OCNHVFNDKJRFOZ-UHFFFAOYSA-N 3-(2-chloro-6-methylpyrimidin-4-yl)benzoic acid Chemical compound ClC1=NC(C)=CC(C=2C=C(C=CC=2)C(O)=O)=N1 OCNHVFNDKJRFOZ-UHFFFAOYSA-N 0.000 description 3
- LZMSCKKGELDRSY-UHFFFAOYSA-N 3-(6-chloropyrimidin-4-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=CN=C(Cl)C=2)=C1 LZMSCKKGELDRSY-UHFFFAOYSA-N 0.000 description 3
- PPWRHKISAQTCCG-UHFFFAOYSA-N 4,5-difluorobenzene-1,2-diamine Chemical compound NC1=CC(F)=C(F)C=C1N PPWRHKISAQTCCG-UHFFFAOYSA-N 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910004373 HOAc Inorganic materials 0.000 description 3
- 101001071429 Homo sapiens Metabotropic glutamate receptor 2 Proteins 0.000 description 3
- 208000007101 Muscle Cramp Diseases 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 150000001805 chlorine compounds Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 3
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- PXVFRKDJZJDKIA-UHFFFAOYSA-N methyl 3-(2-methylpyridin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(C)N=CC=2)=C1 PXVFRKDJZJDKIA-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- FPRARKAQGVXANU-UHFFFAOYSA-N n-[4-methyl-3-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(C(F)(F)F)=C1 FPRARKAQGVXANU-UHFFFAOYSA-N 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- DSKRONAQJOXJJW-UHFFFAOYSA-N tert-butyl 3-[3-(6-cyanopyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NC(=CC=2)C#N)=C1 DSKRONAQJOXJJW-UHFFFAOYSA-N 0.000 description 3
- KCZFBLNQOSFGSH-UHFFFAOYSA-N tert-butyl n-(2-aminophenyl)carbamate Chemical class CC(C)(C)OC(=O)NC1=CC=CC=C1N KCZFBLNQOSFGSH-UHFFFAOYSA-N 0.000 description 3
- IJKLTMRZHAHGDZ-UHFFFAOYSA-N tert-butyl n-(2-nitro-4-pyrrol-1-ylphenyl)carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=C1N1C=CC=C1 IJKLTMRZHAHGDZ-UHFFFAOYSA-N 0.000 description 3
- SFFCGMUSTDBPCP-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 SFFCGMUSTDBPCP-UHFFFAOYSA-N 0.000 description 3
- LHRQEQNDWOPMMP-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 LHRQEQNDWOPMMP-UHFFFAOYSA-N 0.000 description 3
- QSGQLXPYAUJXBX-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-pyrrol-1-ylphenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(C=2)N2C=CC=C2)NC(=O)OC(C)(C)C)=C1 QSGQLXPYAUJXBX-UHFFFAOYSA-N 0.000 description 3
- CRVCIZPQXNRXCZ-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(6-methylpyridazin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound N1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 CRVCIZPQXNRXCZ-UHFFFAOYSA-N 0.000 description 3
- MQOPROVXZLTCGB-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 MQOPROVXZLTCGB-UHFFFAOYSA-N 0.000 description 3
- RXSGWACHXZULCV-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 RXSGWACHXZULCV-UHFFFAOYSA-N 0.000 description 3
- KDSXBEQDPUUIRI-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 KDSXBEQDPUUIRI-UHFFFAOYSA-N 0.000 description 3
- ZLZHNYHPFFPYKL-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-4-pyrrol-1-ylphenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N2C=CC=C2)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CC=CC=N1 ZLZHNYHPFFPYKL-UHFFFAOYSA-N 0.000 description 3
- KEBHZTNBBTUQPP-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 KEBHZTNBBTUQPP-UHFFFAOYSA-N 0.000 description 3
- UNYJIADSXJRCEP-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=CC=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 UNYJIADSXJRCEP-UHFFFAOYSA-N 0.000 description 3
- VYCGZQZPCOTYEU-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 VYCGZQZPCOTYEU-UHFFFAOYSA-N 0.000 description 3
- MMSOUSOYYNDHGP-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 MMSOUSOYYNDHGP-UHFFFAOYSA-N 0.000 description 3
- ZPYDTMSSNAYDNW-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=CC=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 ZPYDTMSSNAYDNW-UHFFFAOYSA-N 0.000 description 3
- KMAGHOMRZMSQFA-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 KMAGHOMRZMSQFA-UHFFFAOYSA-N 0.000 description 3
- XGCMLPMAAYEMRS-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 XGCMLPMAAYEMRS-UHFFFAOYSA-N 0.000 description 3
- NKAPFYHGQINYMV-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=CC=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 NKAPFYHGQINYMV-UHFFFAOYSA-N 0.000 description 3
- ATYYCBDJUSUQJQ-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(OCC(F)(F)F)C=C1N ATYYCBDJUSUQJQ-UHFFFAOYSA-N 0.000 description 3
- XTFQHQUHVPJOCG-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(2-methylpropylamino)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)CNC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C(F)(F)F XTFQHQUHVPJOCG-UHFFFAOYSA-N 0.000 description 3
- MRCLOHDWXPDMGD-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(oxan-2-yloxymethyl)-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(COC2OCCCC2)=C1C(F)(F)F MRCLOHDWXPDMGD-UHFFFAOYSA-N 0.000 description 3
- IBSWABSPOIPRBR-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[cyclopropyl(methyl)amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C=1C(NC(=O)OC(C)(C)C)=C(N)C=C(C(F)(F)F)C=1N(C)C1CC1 IBSWABSPOIPRBR-UHFFFAOYSA-N 0.000 description 3
- RVTRQYWXAXXPJC-UHFFFAOYSA-N tert-butyl n-[2-nitro-4-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(OCC(F)(F)F)C=C1[N+]([O-])=O RVTRQYWXAXXPJC-UHFFFAOYSA-N 0.000 description 3
- GCNITTRPZHHGGU-UHFFFAOYSA-N tert-butyl n-[2-nitro-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=CC=C1[N+]([O-])=O GCNITTRPZHHGGU-UHFFFAOYSA-N 0.000 description 3
- WGLJJWTWJCBCRU-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-[3-(2-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound CC1=NC=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C=2C(=CC=CC=2)F)NC(=O)OC(C)(C)C)=C1 WGLJJWTWJCBCRU-UHFFFAOYSA-N 0.000 description 3
- JLQVKKVHDWNIAP-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(C=2)C=2C(=CC=CC=2)F)NC(=O)OC(C)(C)C)=C1 JLQVKKVHDWNIAP-UHFFFAOYSA-N 0.000 description 3
- XHDUFHOKHSKKEV-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-[3-(6-methoxypyridazin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound N1=NC(OC)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C=2C(=CC=CC=2)F)NC(=O)OC(C)(C)C)=C1 XHDUFHOKHSKKEV-UHFFFAOYSA-N 0.000 description 3
- DOTUXDOIWXTKBF-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C=2C(=CC=CC=2)F)NC(=O)OC(C)(C)C)=C1 DOTUXDOIWXTKBF-UHFFFAOYSA-N 0.000 description 3
- QMOXTFVWICAQHY-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=2C(=CC=CC=2)F)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CN=CC=N1 QMOXTFVWICAQHY-UHFFFAOYSA-N 0.000 description 3
- GBEZKWXCKYONMV-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=2C(=CC=CC=2)F)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CC=CC=N1 GBEZKWXCKYONMV-UHFFFAOYSA-N 0.000 description 3
- NAUFAOLBNQRHAM-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=2C(=CC=CC=2)F)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CC=CN=C1 NAUFAOLBNQRHAM-UHFFFAOYSA-N 0.000 description 3
- DJCJNJXPFYMGCV-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=2C(=CC=CC=2)F)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CN=CN=C1 DJCJNJXPFYMGCV-UHFFFAOYSA-N 0.000 description 3
- RTBRSUJOBOUABD-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(2-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound CC1=NC=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 RTBRSUJOBOUABD-UHFFFAOYSA-N 0.000 description 3
- NQMNOPBAIYEGMC-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(=C(Cl)C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 NQMNOPBAIYEGMC-UHFFFAOYSA-N 0.000 description 3
- ILVKUJPWGPJWDG-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 ILVKUJPWGPJWDG-UHFFFAOYSA-N 0.000 description 3
- XCFCKOVHNVYAJH-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 XCFCKOVHNVYAJH-UHFFFAOYSA-N 0.000 description 3
- CKLQTUKMKLIUDV-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 CKLQTUKMKLIUDV-UHFFFAOYSA-N 0.000 description 3
- DQLSMBHPICEIKM-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 DQLSMBHPICEIKM-UHFFFAOYSA-N 0.000 description 3
- KYRSEBMPYKYBDB-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 KYRSEBMPYKYBDB-UHFFFAOYSA-N 0.000 description 3
- WQOSXOVPDUSLRR-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 WQOSXOVPDUSLRR-UHFFFAOYSA-N 0.000 description 3
- DJIKJHKSXFGROJ-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 DJIKJHKSXFGROJ-UHFFFAOYSA-N 0.000 description 3
- QRNUUOLMGOOOSO-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-nitro-5-(2,2,2-trifluoroethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(Cl)C=C1[N+]([O-])=O QRNUUOLMGOOOSO-UHFFFAOYSA-N 0.000 description 3
- WKBDTTDZYIUVRS-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-(2-methylpropylamino)-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NCC(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=CC=2)=C1 WKBDTTDZYIUVRS-UHFFFAOYSA-N 0.000 description 3
- LMEFLHAIXMTWBA-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-(2-methylpropylamino)-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NCC(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 LMEFLHAIXMTWBA-UHFFFAOYSA-N 0.000 description 3
- XMIUEPJSUSFUQD-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-fluoro-2-[[3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC(F)=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 XMIUEPJSUSFUQD-UHFFFAOYSA-N 0.000 description 3
- WVMRVVSOSSLCAN-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(C)=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 WVMRVVSOSSLCAN-UHFFFAOYSA-N 0.000 description 3
- AIPOKAWCNBBIOZ-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 AIPOKAWCNBBIOZ-UHFFFAOYSA-N 0.000 description 3
- NRXSUYKPHYJPRN-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-oxo-3-(3-pyridazin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NN=CC=2)=C1 NRXSUYKPHYJPRN-UHFFFAOYSA-N 0.000 description 3
- CGVDLYACFJEACR-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 CGVDLYACFJEACR-UHFFFAOYSA-N 0.000 description 3
- LZHQCXTVNUERHN-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 LZHQCXTVNUERHN-UHFFFAOYSA-N 0.000 description 3
- YORWPNQZCXFJON-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 YORWPNQZCXFJON-UHFFFAOYSA-N 0.000 description 3
- NOWYBKYVXKHRQK-UHFFFAOYSA-N tert-butyl n-[4-fluoro-2-[[3-[3-(2-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound CC1=NC=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(F)C=2)NC(=O)OC(C)(C)C)=C1 NOWYBKYVXKHRQK-UHFFFAOYSA-N 0.000 description 3
- XBPWWQMDMWSCAK-UHFFFAOYSA-N tert-butyl n-[4-fluoro-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(F)C=2)NC(=O)OC(C)(C)C)=C1 XBPWWQMDMWSCAK-UHFFFAOYSA-N 0.000 description 3
- JXEYQLQQLRBVLH-UHFFFAOYSA-N tert-butyl n-[4-fluoro-2-[[3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(F)C=2)NC(=O)OC(C)(C)C)=C1 JXEYQLQQLRBVLH-UHFFFAOYSA-N 0.000 description 3
- DYRAPSKBJKDTGN-UHFFFAOYSA-N tert-butyl n-[4-fluoro-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 DYRAPSKBJKDTGN-UHFFFAOYSA-N 0.000 description 3
- NFBDWKSVJXYHCF-UHFFFAOYSA-N tert-butyl n-[4-fluoro-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 NFBDWKSVJXYHCF-UHFFFAOYSA-N 0.000 description 3
- BMKMEBMFUKHEPU-UHFFFAOYSA-N tert-butyl n-[4-methoxy-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)(C)C)C(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=CN=CC=2)=C1 BMKMEBMFUKHEPU-UHFFFAOYSA-N 0.000 description 3
- GOLMVUOFGGPYQG-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(=C(C)C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 GOLMVUOFGGPYQG-UHFFFAOYSA-N 0.000 description 3
- LYSCMLXYTWGONW-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2N=CC=NC=2)=C1NC(=O)OC(C)(C)C LYSCMLXYTWGONW-UHFFFAOYSA-N 0.000 description 3
- IJRGACZLYOYJIX-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=CN=CC=2)=C1NC(=O)OC(C)(C)C IJRGACZLYOYJIX-UHFFFAOYSA-N 0.000 description 3
- MVAPUEXZUCAICG-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=NC=NC=2)=C1NC(=O)OC(C)(C)C MVAPUEXZUCAICG-UHFFFAOYSA-N 0.000 description 3
- NPBMVLZIDMWHLR-UHFFFAOYSA-N tert-butyl n-[5-(2-methoxyethoxy)-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound COCCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F NPBMVLZIDMWHLR-UHFFFAOYSA-N 0.000 description 3
- LMHVQSUVLTZVGO-UHFFFAOYSA-N tert-butyl n-[5-(2-methylpropylamino)-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NCC(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 LMHVQSUVLTZVGO-UHFFFAOYSA-N 0.000 description 3
- XSJNVTIIPMNDRR-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-[3-(2,6-dimethylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C(=NC(C)=CC=2)C)=C1 XSJNVTIIPMNDRR-UHFFFAOYSA-N 0.000 description 3
- HQIQHMVJFHZSNI-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-[3-(2-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C(=NC=CC=2)C)=C1 HQIQHMVJFHZSNI-UHFFFAOYSA-N 0.000 description 3
- QEZOLOLBNJYXCI-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-[3-(6-methoxypyridazin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound N1=NC(OC)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC(=C(C=2)C(F)(F)F)N(C)C)NC(=O)OC(C)(C)C)=C1 QEZOLOLBNJYXCI-UHFFFAOYSA-N 0.000 description 3
- SAQONGYYTBDYNR-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-[3-(6-methylpyridazin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=NC(C)=CC=2)=C1 SAQONGYYTBDYNR-UHFFFAOYSA-N 0.000 description 3
- FGXZSNWJBLESHN-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-[3-(6-methylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC(C)=CC=2)=C1 FGXZSNWJBLESHN-UHFFFAOYSA-N 0.000 description 3
- QEDOJLBFIFQZMO-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 QEDOJLBFIFQZMO-UHFFFAOYSA-N 0.000 description 3
- ZNIWARGZPPIEQD-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 ZNIWARGZPPIEQD-UHFFFAOYSA-N 0.000 description 3
- ZXELKRCHWGUXOM-UHFFFAOYSA-N tert-butyl n-[5-[cyclopropyl(methyl)amino]-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C=1C(NC(=O)OC(C)(C)C)=C(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=C(C(F)(F)F)C=1N(C)C1CC1 ZXELKRCHWGUXOM-UHFFFAOYSA-N 0.000 description 3
- PLLUXTVCAFEEFQ-UHFFFAOYSA-N tert-butyl n-[5-[cyclopropyl(methyl)amino]-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound C=1C(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C(C(F)(F)F)C=1N(C)C1CC1 PLLUXTVCAFEEFQ-UHFFFAOYSA-N 0.000 description 3
- NRYOCASQKQZBJI-UHFFFAOYSA-N tert-butyl n-[5-[methyl(propan-2-yl)amino]-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)N(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F NRYOCASQKQZBJI-UHFFFAOYSA-N 0.000 description 3
- OVHHMYBZOZDCIJ-UHFFFAOYSA-N tert-butyl n-[5-[methyl(propyl)amino]-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)CCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=CC=2)=C1 OVHHMYBZOZDCIJ-UHFFFAOYSA-N 0.000 description 3
- OMXQDZGLFAFFMG-UHFFFAOYSA-N tert-butyl n-[5-[methyl(propyl)amino]-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)CCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 OMXQDZGLFAFFMG-UHFFFAOYSA-N 0.000 description 3
- DHRPZVAAUNBRBI-UHFFFAOYSA-N tert-butyl n-[5-[methyl(propyl)amino]-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)CCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 DHRPZVAAUNBRBI-UHFFFAOYSA-N 0.000 description 3
- IEHXFXJFTUBGTJ-UHFFFAOYSA-N tert-butyl n-[5-[methyl(propyl)amino]-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)CCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 IEHXFXJFTUBGTJ-UHFFFAOYSA-N 0.000 description 3
- KVLYBUAHJPTZFY-UHFFFAOYSA-N tert-butyl n-[5-[methyl(propyl)amino]-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCCN(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F KVLYBUAHJPTZFY-UHFFFAOYSA-N 0.000 description 3
- DPTDZVLRBMCJEJ-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(Cl)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 DPTDZVLRBMCJEJ-UHFFFAOYSA-N 0.000 description 3
- WJYLKMVFCSZNPK-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 WJYLKMVFCSZNPK-UHFFFAOYSA-N 0.000 description 3
- OYYWSCUJQPIHMZ-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 OYYWSCUJQPIHMZ-UHFFFAOYSA-N 0.000 description 3
- ZDUKAULYNYPEQL-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 ZDUKAULYNYPEQL-UHFFFAOYSA-N 0.000 description 3
- UHEVPEPVQWAYOH-UHFFFAOYSA-N tert-butyl n-[5-chloro-4-(2-fluorophenyl)-2-nitrophenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(Cl)=C1C1=CC=CC=C1F UHEVPEPVQWAYOH-UHFFFAOYSA-N 0.000 description 3
- HPOFWGSBPYENNC-UHFFFAOYSA-N tert-butyl n-[5-chloro-4-methyl-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(Cl)=C(C)C=2)NC(=O)OC(C)(C)C)=C1 HPOFWGSBPYENNC-UHFFFAOYSA-N 0.000 description 3
- WGLJQSMQTFHIEH-UHFFFAOYSA-N tert-butyl n-[5-chloro-4-methyl-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2N=CC=NC=2)=C1NC(=O)OC(C)(C)C WGLJQSMQTFHIEH-UHFFFAOYSA-N 0.000 description 3
- DDDVJXUWXZETBH-UHFFFAOYSA-N tert-butyl n-[5-chloro-4-methyl-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=CN=CC=2)=C1NC(=O)OC(C)(C)C DDDVJXUWXZETBH-UHFFFAOYSA-N 0.000 description 3
- FUQBLUYCWKHFPN-UHFFFAOYSA-N tert-butyl n-[5-ethoxy-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=CC=2)=C1 FUQBLUYCWKHFPN-UHFFFAOYSA-N 0.000 description 3
- SJGJDZNIUXMNCV-UHFFFAOYSA-N tert-butyl n-[5-ethoxy-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 SJGJDZNIUXMNCV-UHFFFAOYSA-N 0.000 description 3
- XMGHXUCGDZPXLZ-UHFFFAOYSA-N tert-butyl n-[5-ethoxy-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 XMGHXUCGDZPXLZ-UHFFFAOYSA-N 0.000 description 3
- YVXHXERLALZTGI-UHFFFAOYSA-N tert-butyl n-[5-methoxy-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 YVXHXERLALZTGI-UHFFFAOYSA-N 0.000 description 3
- QGIQVLOARAFBRB-UHFFFAOYSA-N tert-butyl n-[5-methoxy-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OC)=CC=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 QGIQVLOARAFBRB-UHFFFAOYSA-N 0.000 description 3
- IRVVWLJJIFSECZ-UHFFFAOYSA-N tert-butyl n-[5-methoxy-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 IRVVWLJJIFSECZ-UHFFFAOYSA-N 0.000 description 3
- NGJIIVWYRMAPRQ-UHFFFAOYSA-N tert-butyl n-[5-methoxy-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound COC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F NGJIIVWYRMAPRQ-UHFFFAOYSA-N 0.000 description 3
- KUNHRQURSMSVIR-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(C)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 KUNHRQURSMSVIR-UHFFFAOYSA-N 0.000 description 3
- FSBLWWIXPWPBBY-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 FSBLWWIXPWPBBY-UHFFFAOYSA-N 0.000 description 3
- SJJRXNXNPVMPCM-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-oxo-3-(3-pyridazin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NN=CC=2)=C1 SJJRXNXNPVMPCM-UHFFFAOYSA-N 0.000 description 3
- CGOQYJLKCQDQGU-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 CGOQYJLKCQDQGU-UHFFFAOYSA-N 0.000 description 3
- DDHJNGHMBAIKJK-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 DDHJNGHMBAIKJK-UHFFFAOYSA-N 0.000 description 3
- WIHAGHDBEKRQTC-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 WIHAGHDBEKRQTC-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 description 2
- QNIQGMJOZQYBOX-UHFFFAOYSA-N 2,4-dibromo-6-methylpyridine Chemical compound CC1=CC(Br)=CC(Br)=N1 QNIQGMJOZQYBOX-UHFFFAOYSA-N 0.000 description 2
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 2
- YGHDVPXYUQDBER-UHFFFAOYSA-N 2-(3-methylphenyl)acetaldehyde Chemical compound CC1=CC=CC(CC=O)=C1 YGHDVPXYUQDBER-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- SOHDPICLICFSOP-UHFFFAOYSA-N 2-bromo-6-methylpyridine Chemical compound CC1=CC=CC(Br)=N1 SOHDPICLICFSOP-UHFFFAOYSA-N 0.000 description 2
- KJKIPRQNFDUULB-UHFFFAOYSA-N 2-chloro-4-iodopyridine Chemical compound ClC1=CC(I)=CC=N1 KJKIPRQNFDUULB-UHFFFAOYSA-N 0.000 description 2
- VUNAQOGRLGNALG-UHFFFAOYSA-N 2-chloro-5-nitrobenzene-1,4-diamine Chemical compound NC1=CC([N+]([O-])=O)=C(N)C=C1Cl VUNAQOGRLGNALG-UHFFFAOYSA-N 0.000 description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
- ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 description 2
- SNQDIHJPOWWBNA-UHFFFAOYSA-N 2-nitro-4-pyrrol-1-ylaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1N1C=CC=C1 SNQDIHJPOWWBNA-UHFFFAOYSA-N 0.000 description 2
- CHZPJUSFUDUEMZ-UHFFFAOYSA-N 3-acetylbenzoic acid Chemical compound CC(=O)C1=CC=CC(C(O)=O)=C1 CHZPJUSFUDUEMZ-UHFFFAOYSA-N 0.000 description 2
- TUJVGHCSNXCAFE-UHFFFAOYSA-N 3-bromo-2,6-dimethylpyridine Chemical compound CC1=CC=C(Br)C(C)=N1 TUJVGHCSNXCAFE-UHFFFAOYSA-N 0.000 description 2
- AIPWPTPHMIYYOX-UHFFFAOYSA-N 3-bromo-2-methylpyridine Chemical compound CC1=NC=CC=C1Br AIPWPTPHMIYYOX-UHFFFAOYSA-N 0.000 description 2
- GSQZOLXWFQQJHJ-UHFFFAOYSA-N 3-bromo-4-methylpyridine Chemical compound CC1=CC=NC=C1Br GSQZOLXWFQQJHJ-UHFFFAOYSA-N 0.000 description 2
- XBJLKXOOHLLTPG-UHFFFAOYSA-N 3-chloro-6-methoxypyridazine Chemical compound COC1=CC=C(Cl)N=N1 XBJLKXOOHLLTPG-UHFFFAOYSA-N 0.000 description 2
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 2
- YJNILYRQRSSTPP-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 YJNILYRQRSSTPP-UHFFFAOYSA-N 0.000 description 2
- PHCLIPMSNVUELH-UHFFFAOYSA-N 4-bromo-2,3-dimethylpyridine Chemical compound CC1=NC=CC(Br)=C1C PHCLIPMSNVUELH-UHFFFAOYSA-N 0.000 description 2
- CGPIONYVXKQZPW-UHFFFAOYSA-N 4-bromo-2,5-dimethylpyridine Chemical compound CC1=CC(Br)=C(C)C=N1 CGPIONYVXKQZPW-UHFFFAOYSA-N 0.000 description 2
- VTRFAYHJKSKHGY-UHFFFAOYSA-N 4-bromo-2,6-dimethylpyridine Chemical compound CC1=CC(Br)=CC(C)=N1 VTRFAYHJKSKHGY-UHFFFAOYSA-N 0.000 description 2
- TVRGNBFSOZCSSE-UHFFFAOYSA-N 4-bromo-2-ethylpyridine Chemical compound CCC1=CC(Br)=CC=N1 TVRGNBFSOZCSSE-UHFFFAOYSA-N 0.000 description 2
- JFBMFWHEXBLFCR-UHFFFAOYSA-N 4-bromo-2-methylpyridine Chemical compound CC1=CC(Br)=CC=N1 JFBMFWHEXBLFCR-UHFFFAOYSA-N 0.000 description 2
- XZXFBVQHDDLSQB-UHFFFAOYSA-N 4-bromo-5-ethyl-2-methylpyridine Chemical compound CCC1=CN=C(C)C=C1Br XZXFBVQHDDLSQB-UHFFFAOYSA-N 0.000 description 2
- FZINIBTZNSPWQR-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=CC=N1 FZINIBTZNSPWQR-UHFFFAOYSA-N 0.000 description 2
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 2
- PMEPPZBLQNOHJA-UHFFFAOYSA-N 4-chloro-2-propan-2-ylpyridine Chemical compound CC(C)C1=CC(Cl)=CC=N1 PMEPPZBLQNOHJA-UHFFFAOYSA-N 0.000 description 2
- PUGDHSSOXPHLPT-UHFFFAOYSA-N 4-fluoro-2-nitroaniline Chemical compound NC1=CC=C(F)C=C1[N+]([O-])=O PUGDHSSOXPHLPT-UHFFFAOYSA-N 0.000 description 2
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 2
- FYXBQZHNQFVYDC-UHFFFAOYSA-N 5-(2-methoxyethoxy)-2-nitro-4-(trifluoromethyl)aniline Chemical compound COCCOC1=CC(N)=C([N+]([O-])=O)C=C1C(F)(F)F FYXBQZHNQFVYDC-UHFFFAOYSA-N 0.000 description 2
- SLMUXUHXAIPROA-UHFFFAOYSA-N 5-bromo-2,4-dimethylpyridine Chemical compound CC1=CC(C)=C(Br)C=N1 SLMUXUHXAIPROA-UHFFFAOYSA-N 0.000 description 2
- JFTFIPSATYUJLB-UHFFFAOYSA-N 5-bromo-2-ethylpyridine Chemical compound CCC1=CC=C(Br)C=N1 JFTFIPSATYUJLB-UHFFFAOYSA-N 0.000 description 2
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 2
- XIMCGXXYEMOWQP-UHFFFAOYSA-N 5-bromo-n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=C(Br)C=N1 XIMCGXXYEMOWQP-UHFFFAOYSA-N 0.000 description 2
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 2
- DMSHUVBQFSNBBL-UHFFFAOYSA-N 5-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=C(C#N)N=C1 DMSHUVBQFSNBBL-UHFFFAOYSA-N 0.000 description 2
- NWTQJQSOCJKTDD-UHFFFAOYSA-N 5-ethoxy-2-nitroaniline Chemical compound CCOC1=CC=C([N+]([O-])=O)C(N)=C1 NWTQJQSOCJKTDD-UHFFFAOYSA-N 0.000 description 2
- PEDMFCHWOVJDNW-UHFFFAOYSA-N 5-fluoro-2-nitroaniline Chemical compound NC1=CC(F)=CC=C1[N+]([O-])=O PEDMFCHWOVJDNW-UHFFFAOYSA-N 0.000 description 2
- QEHVRGACCVLLNN-UHFFFAOYSA-N 5-methoxy-2-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C(N)=C1 QEHVRGACCVLLNN-UHFFFAOYSA-N 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- 208000012661 Dyskinesia Diseases 0.000 description 2
- 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 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- 206010019196 Head injury Diseases 0.000 description 2
- 208000010496 Heart Arrest Diseases 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 208000013016 Hypoglycemia Diseases 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 206010057852 Nicotine dependence Diseases 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 208000026251 Opioid-Related disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 208000017442 Retinal disease Diseases 0.000 description 2
- 206010038923 Retinopathy Diseases 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 208000025569 Tobacco Use disease Diseases 0.000 description 2
- 206010046543 Urinary incontinence Diseases 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 208000005298 acute pain Diseases 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N alpha-methylpyridine Natural products CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 239000012148 binding buffer Substances 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 230000036770 blood supply Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 230000003925 brain function Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- YFXCNIVBAVFOBX-UHFFFAOYSA-N ethenylboronic acid Chemical compound OB(O)C=C YFXCNIVBAVFOBX-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 231100000040 eye damage Toxicity 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 229940049906 glutamate Drugs 0.000 description 2
- 239000003825 glutamate receptor antagonist Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- OOXYIUJALJLCPZ-UHFFFAOYSA-N methyl 3-(2-morpholin-4-ylpyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N=CC=2)N2CCOCC2)=C1 OOXYIUJALJLCPZ-UHFFFAOYSA-N 0.000 description 2
- KYFWIAFEEMFUHM-UHFFFAOYSA-N methyl 3-[2-(acetyloxymethyl)-6-methylpyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC(C)=O)N=C(C)C=2)=C1 KYFWIAFEEMFUHM-UHFFFAOYSA-N 0.000 description 2
- SFCOEBBIVJLZHE-UHFFFAOYSA-N methyl 3-[2-(acetyloxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC(C)=O)N=CC=2)=C1 SFCOEBBIVJLZHE-UHFFFAOYSA-N 0.000 description 2
- PQAYIKRNJJSXFD-UHFFFAOYSA-N methyl 3-[2-(oxan-2-yloxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC3OCCCC3)N=CC=2)=C1 PQAYIKRNJJSXFD-UHFFFAOYSA-N 0.000 description 2
- BQEJDUQRPNKRJQ-UHFFFAOYSA-N methyl 3-[2-methyl-6-(oxan-2-yloxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC3OCCCC3)N=C(C)C=2)=C1 BQEJDUQRPNKRJQ-UHFFFAOYSA-N 0.000 description 2
- UTGGIQHJOAPIPD-UHFFFAOYSA-N methyl 3-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=CC(C(Cl)=O)=C1 UTGGIQHJOAPIPD-UHFFFAOYSA-N 0.000 description 2
- WSFNTSUFRZCBNQ-UHFFFAOYSA-N methyl 3-pyridin-2-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 WSFNTSUFRZCBNQ-UHFFFAOYSA-N 0.000 description 2
- HLFKAFNNGCVRIQ-UHFFFAOYSA-N methyl 3-pyridin-3-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 HLFKAFNNGCVRIQ-UHFFFAOYSA-N 0.000 description 2
- OURDGCXMAZZEBC-UHFFFAOYSA-N methyl 3-pyridin-4-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 OURDGCXMAZZEBC-UHFFFAOYSA-N 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 2
- SJSQNQIDPZDPOE-UHFFFAOYSA-N n-[2-nitro-4-(2,2,2-trifluoroethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCC(F)(F)F)C=C1[N+]([O-])=O SJSQNQIDPZDPOE-UHFFFAOYSA-N 0.000 description 2
- UCLBQTSVYJDQRU-UHFFFAOYSA-N n-[2-nitro-4-(trifluoromethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)(F)F)C=C1[N+]([O-])=O UCLBQTSVYJDQRU-UHFFFAOYSA-N 0.000 description 2
- ZZGPUMKJSHUVMF-UHFFFAOYSA-N n-[4-chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1[N+]([O-])=O ZZGPUMKJSHUVMF-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 201000005040 opiate dependence Diseases 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- QVBPZZKELHNMDZ-UHFFFAOYSA-M potassium;3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoate Chemical compound [K+].CC(C)(C)OC(=O)CC([O-])=O QVBPZZKELHNMDZ-UHFFFAOYSA-M 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 2
- 208000020431 spinal cord injury Diseases 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 235000012976 tarts Nutrition 0.000 description 2
- XTWPYJCVFMLTLG-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyrimidin-2-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2N=CC=CN=2)=C1 XTWPYJCVFMLTLG-UHFFFAOYSA-N 0.000 description 2
- IGYXAKCOMRSREX-UHFFFAOYSA-N tert-butyl n-(5-methoxy-2-nitrophenyl)carbamate Chemical compound COC1=CC=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=C1 IGYXAKCOMRSREX-UHFFFAOYSA-N 0.000 description 2
- ADNYTMZEEXURPR-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 ADNYTMZEEXURPR-UHFFFAOYSA-N 0.000 description 2
- VBHYKUQKJLBZLV-UHFFFAOYSA-N tert-butyl n-[2-amino-4-[2-(4-fluorophenyl)ethynyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC=C1C#CC1=CC=C(F)C=C1 VBHYKUQKJLBZLV-UHFFFAOYSA-N 0.000 description 2
- YFGINBUYENXRIR-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-[3-(6-methylpyridazin-3-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound N1=NC(C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC=C(C=2)C=2C(=CC=CC=2)F)NC(=O)OC(C)(C)C)=C1 YFGINBUYENXRIR-UHFFFAOYSA-N 0.000 description 2
- BFYRTEGNAYKEFL-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=2C(=CC=CC=2)F)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CC=NC=C1 BFYRTEGNAYKEFL-UHFFFAOYSA-N 0.000 description 2
- HIJGGUTUMXRNPR-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-[methyl(2-methylpropyl)amino]-2-nitrophenyl]carbamate Chemical compound CC(C)CN(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1Cl HIJGGUTUMXRNPR-UHFFFAOYSA-N 0.000 description 2
- QSOKYLAWCXMFLQ-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound CN(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F QSOKYLAWCXMFLQ-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- 239000001993 wax 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
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- NIPKJXCNBRDLKR-UHFFFAOYSA-N (2-amino-4-chlorophenyl)carbamic acid Chemical compound NC1=CC(Cl)=CC=C1NC(O)=O NIPKJXCNBRDLKR-UHFFFAOYSA-N 0.000 description 1
- WSDOBZDGNHRFFO-UHFFFAOYSA-N (2-amino-4-fluorophenyl)carbamic acid Chemical compound NC1=CC(F)=CC=C1NC(O)=O WSDOBZDGNHRFFO-UHFFFAOYSA-N 0.000 description 1
- QNSNYZHVIPAGMO-UHFFFAOYSA-N (2-cyclopropylpyridin-3-yl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CN=C1C1CC1 QNSNYZHVIPAGMO-UHFFFAOYSA-N 0.000 description 1
- QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DBLSHOGCZJWBHQ-UHFFFAOYSA-N (4-fluoro-2-nitrophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(F)C=C1[N+]([O-])=O DBLSHOGCZJWBHQ-UHFFFAOYSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ODRZAZBEQWAOGU-UHFFFAOYSA-N 1,4-dioxin-2-one Chemical compound O=C1COC=CO1 ODRZAZBEQWAOGU-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VJQCNCOGZPSOQZ-UHFFFAOYSA-N 1-Methylguanidine hydrochloride Chemical compound [Cl-].C[NH2+]C(N)=N VJQCNCOGZPSOQZ-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
- JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 description 1
- BTLKROSJMNFSQZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(Cl)=N1 BTLKROSJMNFSQZ-UHFFFAOYSA-N 0.000 description 1
- DYOSAFQUIFEGSK-UHFFFAOYSA-N 2,5-dimethoxy-2,3-dihydrofuran Chemical class COC1CC=C(OC)O1 DYOSAFQUIFEGSK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CKUVSPQGYLELRG-UHFFFAOYSA-N 2-chloro-6-methylpyrazine Chemical compound CC1=CN=CC(Cl)=N1 CKUVSPQGYLELRG-UHFFFAOYSA-N 0.000 description 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
- SNXVQJGWPUOWNB-UHFFFAOYSA-N 2-hydroxy-3-(3-methylphenyl)-2h-furan-5-one Chemical compound CC1=CC=CC(C=2C(OC(=O)C=2)O)=C1 SNXVQJGWPUOWNB-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- GVTXFPNAFWHMMV-UHFFFAOYSA-N 2-nitro-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)aniline Chemical compound NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1[N+]([O-])=O GVTXFPNAFWHMMV-UHFFFAOYSA-N 0.000 description 1
- SAPCIVWKZSLXAM-UHFFFAOYSA-N 2-nitro-5-(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC(OCC(F)(F)F)=CC=C1[N+]([O-])=O SAPCIVWKZSLXAM-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
- FXRURCGCFQTFMI-UHFFFAOYSA-N 3-(2,6-dimethylpyridin-3-yl)benzonitrile Chemical compound CC1=NC(C)=CC=C1C1=CC=CC(C#N)=C1 FXRURCGCFQTFMI-UHFFFAOYSA-N 0.000 description 1
- QKEFOVJZNPELQH-UHFFFAOYSA-N 3-(2-bromoacetyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)CBr)=C1 QKEFOVJZNPELQH-UHFFFAOYSA-N 0.000 description 1
- ZROOMNRYBOECDF-UHFFFAOYSA-N 3-(2-cyclopentylpyridin-4-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C(N=CC=2)C2CCCC2)=C1 ZROOMNRYBOECDF-UHFFFAOYSA-N 0.000 description 1
- DUJMAOVDRZOHGE-UHFFFAOYSA-N 3-(2-cyclopropyl-6-methylpyridin-4-yl)benzonitrile Chemical compound N=1C(C)=CC(C=2C=C(C=CC=2)C#N)=CC=1C1CC1 DUJMAOVDRZOHGE-UHFFFAOYSA-N 0.000 description 1
- WRWYUAYQYDGFHD-UHFFFAOYSA-N 3-(2-cyclopropylpyridin-3-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C(=NC=CC=2)C2CC2)=C1 WRWYUAYQYDGFHD-UHFFFAOYSA-N 0.000 description 1
- VKIAIGUOWACBNH-UHFFFAOYSA-N 3-(2-cyclopropylpyridin-4-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C(N=CC=2)C2CC2)=C1 VKIAIGUOWACBNH-UHFFFAOYSA-N 0.000 description 1
- KCSRSZOSVPDXAX-UHFFFAOYSA-N 3-(2-ethyl-6-methylpyridin-4-yl)benzonitrile Chemical compound CC1=NC(CC)=CC(C=2C=C(C=CC=2)C#N)=C1 KCSRSZOSVPDXAX-UHFFFAOYSA-N 0.000 description 1
- AVZKWDXVYWSCMD-UHFFFAOYSA-N 3-(2-ethylpyridin-3-yl)benzonitrile Chemical compound CCC1=NC=CC=C1C1=CC=CC(C#N)=C1 AVZKWDXVYWSCMD-UHFFFAOYSA-N 0.000 description 1
- GEKMVPPMZHSRKV-UHFFFAOYSA-N 3-(2-morpholin-4-ylpyridin-4-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C(N=CC=2)N2CCOCC2)=C1 GEKMVPPMZHSRKV-UHFFFAOYSA-N 0.000 description 1
- YDEIBHFYEGTOIW-UHFFFAOYSA-N 3-(2-pyrrolidin-1-ylpyridin-4-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C(N=CC=2)N2CCCC2)=C1 YDEIBHFYEGTOIW-UHFFFAOYSA-N 0.000 description 1
- ZDZGFWIYXDXSJY-UHFFFAOYSA-N 3-(4,6-dimethylpyridin-3-yl)benzonitrile Chemical compound C1=NC(C)=CC(C)=C1C1=CC=CC(C#N)=C1 ZDZGFWIYXDXSJY-UHFFFAOYSA-N 0.000 description 1
- AHEVTHNZDVVQBC-UHFFFAOYSA-N 3-(4-methylpyridin-3-yl)benzonitrile Chemical compound CC1=CC=NC=C1C1=CC=CC(C#N)=C1 AHEVTHNZDVVQBC-UHFFFAOYSA-N 0.000 description 1
- DKTXBIIMOGXSQM-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)benzonitrile Chemical compound C1=NC(N)=CC=C1C1=CC=CC(C#N)=C1 DKTXBIIMOGXSQM-UHFFFAOYSA-N 0.000 description 1
- VXSVLEURSYPABD-UHFFFAOYSA-N 3-(6-cyclopropyl-4-methylpyridin-3-yl)benzonitrile Chemical compound CC1=CC(C2CC2)=NC=C1C1=CC=CC(C#N)=C1 VXSVLEURSYPABD-UHFFFAOYSA-N 0.000 description 1
- HTHFGQMBJSBWHT-UHFFFAOYSA-N 3-(6-cyclopropylpyridin-3-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=NC(=CC=2)C2CC2)=C1 HTHFGQMBJSBWHT-UHFFFAOYSA-N 0.000 description 1
- GJMSTQFUMFGYRG-UHFFFAOYSA-N 3-(6-ethyl-4-methylpyridin-3-yl)benzonitrile Chemical compound C1=NC(CC)=CC(C)=C1C1=CC=CC(C#N)=C1 GJMSTQFUMFGYRG-UHFFFAOYSA-N 0.000 description 1
- GQQKNPLHCHVXSL-UHFFFAOYSA-N 3-(6-ethylpyridin-3-yl)benzonitrile Chemical compound C1=NC(CC)=CC=C1C1=CC=CC(C#N)=C1 GQQKNPLHCHVXSL-UHFFFAOYSA-N 0.000 description 1
- SPPVWLFSLKDMAS-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)benzonitrile Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(C#N)=C1 SPPVWLFSLKDMAS-UHFFFAOYSA-N 0.000 description 1
- MJCABNVMZKKFIF-UHFFFAOYSA-N 3-(6-methylpyridin-2-yl)benzonitrile Chemical compound CC1=CC=CC(C=2C=C(C=CC=2)C#N)=N1 MJCABNVMZKKFIF-UHFFFAOYSA-N 0.000 description 1
- QCAKXKJAUSIWKB-UHFFFAOYSA-N 3-(6-propan-2-ylpyridin-3-yl)benzonitrile Chemical compound C1=NC(C(C)C)=CC=C1C1=CC=CC(C#N)=C1 QCAKXKJAUSIWKB-UHFFFAOYSA-N 0.000 description 1
- QPUVFEMYORGPAE-UHFFFAOYSA-N 3-(hydrazinecarbonyl)benzoic acid Chemical compound NNC(=O)C1=CC=CC(C(O)=O)=C1 QPUVFEMYORGPAE-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
- CDVKHUMWDJXCNG-UHFFFAOYSA-N 3-[6-(dimethylamino)pyridin-3-yl]benzonitrile Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=CC(C#N)=C1 CDVKHUMWDJXCNG-UHFFFAOYSA-N 0.000 description 1
- JOXPMEKMQIMKDS-UHFFFAOYSA-N 3-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]benzoic acid Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC=CC(C(O)=O)=C1 JOXPMEKMQIMKDS-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XBOVDQCWXXYOIV-UHFFFAOYSA-N 3-chloro-5-(3-methylphenyl)pyridazine Chemical compound CC1=CC=CC(C=2C=C(Cl)N=NC=2)=C1 XBOVDQCWXXYOIV-UHFFFAOYSA-N 0.000 description 1
- PRORLQAJNJMGAR-UHFFFAOYSA-N 3-chloro-6-methylpyridazine Chemical compound CC1=CC=C(Cl)N=N1 PRORLQAJNJMGAR-UHFFFAOYSA-N 0.000 description 1
- CRRVZRDISHOQQL-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C(F)=C1 CRRVZRDISHOQQL-UHFFFAOYSA-N 0.000 description 1
- ZFOCSCYEBFCSDS-UHFFFAOYSA-N 3-oxaldehydoylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=O)=C1 ZFOCSCYEBFCSDS-UHFFFAOYSA-N 0.000 description 1
- PKQIDSVLSKFZQC-UHFFFAOYSA-N 3-oxobutanal Chemical compound CC(=O)CC=O PKQIDSVLSKFZQC-UHFFFAOYSA-N 0.000 description 1
- AWOBORBXAQGQQD-UHFFFAOYSA-N 3-pyridazin-4-ylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=NN=CC=2)=C1 AWOBORBXAQGQQD-UHFFFAOYSA-N 0.000 description 1
- KLTNGIZIUGYITR-UHFFFAOYSA-N 3-pyrimidin-2-ylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=CC=CN=2)=C1 KLTNGIZIUGYITR-UHFFFAOYSA-N 0.000 description 1
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-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
- BVJVYQLXWNWSRU-UHFFFAOYSA-N 4-(3-methylphenyl)-1h-pyridazin-6-one Chemical compound CC1=CC=CC(C2=CC(=O)NN=C2)=C1 BVJVYQLXWNWSRU-UHFFFAOYSA-N 0.000 description 1
- SJXOZHQWIGFYCU-UHFFFAOYSA-N 4-(3-methylphenyl)pyridazine Chemical compound CC1=CC=CC(C=2C=NN=CC=2)=C1 SJXOZHQWIGFYCU-UHFFFAOYSA-N 0.000 description 1
- XTQHVAXLUHGINO-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-7-(2,2,2-trifluoroethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C2=CC(OCC(F)(F)F)=CC=C2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 XTQHVAXLUHGINO-UHFFFAOYSA-N 0.000 description 1
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 description 1
- PXNOUTUNFINTTA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC(F)(F)F)C=C3N=2)C(F)(F)F)=C1 PXNOUTUNFINTTA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KRNNAUWBHVVWKF-UHFFFAOYSA-N 4-bromo-2-cyclopropyl-6-methylpyridine Chemical compound CC1=CC(Br)=CC(C2CC2)=N1 KRNNAUWBHVVWKF-UHFFFAOYSA-N 0.000 description 1
- WPUFFZAREAXVKG-UHFFFAOYSA-N 4-bromo-2-ethyl-6-methylpyridine Chemical compound CCC1=CC(Br)=CC(C)=N1 WPUFFZAREAXVKG-UHFFFAOYSA-N 0.000 description 1
- HKHDYEPRYRYBJO-UHFFFAOYSA-N 4-chloro-2-(2-methylpropyl)pyridine Chemical compound CC(C)CC1=CC(Cl)=CC=N1 HKHDYEPRYRYBJO-UHFFFAOYSA-N 0.000 description 1
- DTEONTULWKCKED-UHFFFAOYSA-N 4-chloro-2-nitro-5-(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC(OCC(F)(F)F)=C(Cl)C=C1[N+]([O-])=O DTEONTULWKCKED-UHFFFAOYSA-N 0.000 description 1
- ZQNMJROKKGEWDS-UHFFFAOYSA-N 4-chloro-5-ethoxy-2-nitroaniline Chemical compound CCOC1=CC(N)=C([N+]([O-])=O)C=C1Cl ZQNMJROKKGEWDS-UHFFFAOYSA-N 0.000 description 1
- IVUBVUIBVDTNAT-UHFFFAOYSA-N 4-chloro-5-fluoro-2-nitroaniline Chemical compound NC1=CC(F)=C(Cl)C=C1[N+]([O-])=O IVUBVUIBVDTNAT-UHFFFAOYSA-N 0.000 description 1
- JBCDCYFEJQHTTA-UHFFFAOYSA-N 4-methyl-3-(trifluoromethyl)aniline Chemical compound CC1=CC=C(N)C=C1C(F)(F)F JBCDCYFEJQHTTA-UHFFFAOYSA-N 0.000 description 1
- 229940044174 4-phenylenediamine Drugs 0.000 description 1
- VBRYULANOSLPSP-UHFFFAOYSA-N 5-bromo-2-cyclopropyl-4-methylpyridine Chemical compound C1=C(Br)C(C)=CC(C2CC2)=N1 VBRYULANOSLPSP-UHFFFAOYSA-N 0.000 description 1
- WLJWEZIWWHAIEM-UHFFFAOYSA-N 5-bromo-2-cyclopropylpyridine Chemical compound N1=CC(Br)=CC=C1C1CC1 WLJWEZIWWHAIEM-UHFFFAOYSA-N 0.000 description 1
- XNCDFLWWWSYVGR-UHFFFAOYSA-N 5-bromo-2-ethyl-4-methylpyridine Chemical compound CCC1=CC(C)=C(Br)C=N1 XNCDFLWWWSYVGR-UHFFFAOYSA-N 0.000 description 1
- ZDAOSHHGHWFYRW-UHFFFAOYSA-N 5-bromo-2-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=CC=C(Br)C=N1 ZDAOSHHGHWFYRW-UHFFFAOYSA-N 0.000 description 1
- GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- KWHURWOGZQWLTK-UHFFFAOYSA-N 5-chloro-4-iodo-2-nitroaniline Chemical compound NC1=CC(Cl)=C(I)C=C1[N+]([O-])=O KWHURWOGZQWLTK-UHFFFAOYSA-N 0.000 description 1
- BBWHBSDZHSQECL-UHFFFAOYSA-N 5-chloro-4-methyl-2-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=C(N)C=C1Cl BBWHBSDZHSQECL-UHFFFAOYSA-N 0.000 description 1
- VTDFAFMHBFUGLN-UHFFFAOYSA-N 5-cyclopropyl-n-methoxy-2-nitro-4-(trifluoromethyl)aniline Chemical compound C1=C([N+]([O-])=O)C(NOC)=CC(C2CC2)=C1C(F)(F)F VTDFAFMHBFUGLN-UHFFFAOYSA-N 0.000 description 1
- NSUBCFDZJGKSLM-UHFFFAOYSA-N 5-ethoxy-2-nitro-4-(trifluoromethyl)aniline Chemical compound CCOC1=CC(N)=C([N+]([O-])=O)C=C1C(F)(F)F NSUBCFDZJGKSLM-UHFFFAOYSA-N 0.000 description 1
- UTRVMCDXCUQEEJ-UHFFFAOYSA-N 5-fluoro-2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC(F)=C(C(F)(F)F)C=C1[N+]([O-])=O UTRVMCDXCUQEEJ-UHFFFAOYSA-N 0.000 description 1
- HJFCWKRMUCQYHF-UHFFFAOYSA-N 5-methoxy-2-nitro-4-(trifluoromethyl)aniline Chemical compound COC1=CC(N)=C([N+]([O-])=O)C=C1C(F)(F)F HJFCWKRMUCQYHF-UHFFFAOYSA-N 0.000 description 1
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 description 1
- BAXARIOGPJRTLH-UHFFFAOYSA-N 7-(cyclopropylmethoxy)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC4CC4)C=C3N=2)C(F)(F)F)=C1 BAXARIOGPJRTLH-UHFFFAOYSA-N 0.000 description 1
- DZCFLWXSUXKAJI-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 DZCFLWXSUXKAJI-UHFFFAOYSA-N 0.000 description 1
- YQKASQGOPRPMLH-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 YQKASQGOPRPMLH-UHFFFAOYSA-N 0.000 description 1
- RHZYZFRVSNAAOL-UHFFFAOYSA-N 7-ethoxy-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 RHZYZFRVSNAAOL-UHFFFAOYSA-N 0.000 description 1
- XXIAOXVQWLJIRI-UHFFFAOYSA-N 7-ethoxy-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 XXIAOXVQWLJIRI-UHFFFAOYSA-N 0.000 description 1
- XJKJJKMFTRWVGB-UHFFFAOYSA-N 7-methoxy-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 XJKJJKMFTRWVGB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PQMAJJWGJPOQQE-UHFFFAOYSA-N 8-chloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(Cl)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 PQMAJJWGJPOQQE-UHFFFAOYSA-N 0.000 description 1
- PRPOBZJPAWDSGQ-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-4-yl)phenyl]-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C=C3N=2)C(F)(F)F)=C1 PRPOBZJPAWDSGQ-UHFFFAOYSA-N 0.000 description 1
- QPHSKVNFGZIDPN-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QPHSKVNFGZIDPN-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KVLVEFGREJDWDH-UHFFFAOYSA-N CCOC1=CC=C(N)C(NC(O)=O)=C1 Chemical compound CCOC1=CC=C(N)C(NC(O)=O)=C1 KVLVEFGREJDWDH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000080335 Citrus x limonia Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 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
- 108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
- 102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
- 102100038352 Metabotropic glutamate receptor 3 Human genes 0.000 description 1
- 102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 description 1
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 description 1
- 102100038300 Metabotropic glutamate receptor 6 Human genes 0.000 description 1
- 102100038294 Metabotropic glutamate receptor 7 Human genes 0.000 description 1
- 102100037636 Metabotropic glutamate receptor 8 Human genes 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 229930193140 Neomycin Natural products 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 108010006785 Taq Polymerase Proteins 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
- 239000007983 Tris buffer Substances 0.000 description 1
- QTEJMJFZFBNYTF-UHFFFAOYSA-N [5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-nitro-2-(trifluoromethyl)phenyl]methyl acetate Chemical compound CC(=O)OCC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C(F)(F)F QTEJMJFZFBNYTF-UHFFFAOYSA-N 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- ATCKJLDGNXGLAO-UHFFFAOYSA-N bis(trimethylsilyl) propanedioate Chemical compound C[Si](C)(C)OC(=O)CC(=O)O[Si](C)(C)C ATCKJLDGNXGLAO-UHFFFAOYSA-N 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- MATPZHBYOVDBLI-JJYYJPOSSA-N dcg-iv Chemical compound OC(=O)[C@@H](N)C1[C@@H](C(O)=O)[C@@H]1C(O)=O MATPZHBYOVDBLI-JJYYJPOSSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005828 desilylation reaction Methods 0.000 description 1
- ACPFLXJEPKOPGF-UHFFFAOYSA-N diaminomethylidene(dimethyl)azanium;hydrogen sulfate Chemical compound [O-]S([O-])(=O)=O.C[NH+](C)C([NH3+])=N ACPFLXJEPKOPGF-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- VKGUPQJMMDGGPY-UHFFFAOYSA-N ethyl 3-(2-cyanopyridin-4-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2C=C(N=CC=2)C#N)=C1 VKGUPQJMMDGGPY-UHFFFAOYSA-N 0.000 description 1
- JURNESPAKRBWFF-UHFFFAOYSA-N ethyl 3-pyridin-4-ylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 JURNESPAKRBWFF-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- UZNGRHDUJIVHQT-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].C[C-]=C UZNGRHDUJIVHQT-UHFFFAOYSA-M 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
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 108010038421 metabotropic glutamate receptor 2 Proteins 0.000 description 1
- 108010038445 metabotropic glutamate receptor 3 Proteins 0.000 description 1
- 108010038422 metabotropic glutamate receptor 4 Proteins 0.000 description 1
- 108010038450 metabotropic glutamate receptor 6 Proteins 0.000 description 1
- 108010038449 metabotropic glutamate receptor 7 Proteins 0.000 description 1
- 108010038448 metabotropic glutamate receptor 8 Proteins 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VLGJAQOVHJDEAJ-UHFFFAOYSA-N methyl 2-(2-methylpyridin-4-yl)pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C=2C=C(C)N=CC=2)=C1 VLGJAQOVHJDEAJ-UHFFFAOYSA-N 0.000 description 1
- HIFPODUERXROFH-UHFFFAOYSA-N methyl 2-pyridin-3-ylpyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C=2C=NC=CC=2)=C1 HIFPODUERXROFH-UHFFFAOYSA-N 0.000 description 1
- XQGCMTQZYKUNTG-UHFFFAOYSA-N methyl 2-pyridin-4-ylpyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C=2C=CN=CC=2)=C1 XQGCMTQZYKUNTG-UHFFFAOYSA-N 0.000 description 1
- MOROTUNSYIQVSH-UHFFFAOYSA-N methyl 3-(2,6-dimethylpyridin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(C)N=C(C)C=2)=C1 MOROTUNSYIQVSH-UHFFFAOYSA-N 0.000 description 1
- QHVUAQWSFHGQSS-UHFFFAOYSA-N methyl 3-(2-amino-6-methylpyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N)N=C(C)C=2)=C1 QHVUAQWSFHGQSS-UHFFFAOYSA-N 0.000 description 1
- LEKLAXUYPKSYOU-UHFFFAOYSA-N methyl 3-(2-aminopyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N)N=CC=2)=C1 LEKLAXUYPKSYOU-UHFFFAOYSA-N 0.000 description 1
- QDWVBIOMVCNXCM-UHFFFAOYSA-N methyl 3-(2-methylpyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(=NC=CC=2)C)=C1 QDWVBIOMVCNXCM-UHFFFAOYSA-N 0.000 description 1
- JNZREOLYWJGVGK-UHFFFAOYSA-N methyl 3-(2-methylpyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(C)N=CC=2)=C1 JNZREOLYWJGVGK-UHFFFAOYSA-N 0.000 description 1
- BNJAKNOEMIPOET-UHFFFAOYSA-N methyl 3-(3-methyl-1,2,4-triazin-6-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC(C)=NC=2)=C1 BNJAKNOEMIPOET-UHFFFAOYSA-N 0.000 description 1
- ILLWHUXRPCCWQN-UHFFFAOYSA-N methyl 3-(3-oxobutanoyl)benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)CC(C)=O)=C1 ILLWHUXRPCCWQN-UHFFFAOYSA-N 0.000 description 1
- MJXHWGZUDXWAKC-UHFFFAOYSA-N methyl 3-(5,6-dimethyl-1,2,4-triazin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(C)C(C)=NN=2)=C1 MJXHWGZUDXWAKC-UHFFFAOYSA-N 0.000 description 1
- XYYUHALYKYLVPL-UHFFFAOYSA-N methyl 3-(6-cyanopyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=NC(=CC=2)C#N)=C1 XYYUHALYKYLVPL-UHFFFAOYSA-N 0.000 description 1
- KBFWJKJSQVKEPX-UHFFFAOYSA-N methyl 3-(6-methoxypyridazin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC(OC)=CC=2)=C1 KBFWJKJSQVKEPX-UHFFFAOYSA-N 0.000 description 1
- GTLIWFAEWCMGRX-UHFFFAOYSA-N methyl 3-(6-methylpyridazin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC(C)=CC=2)=C1 GTLIWFAEWCMGRX-UHFFFAOYSA-N 0.000 description 1
- HWQAEDWFEPDMOX-UHFFFAOYSA-N methyl 3-(6-methylpyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=NC(C)=CC=2)=C1 HWQAEDWFEPDMOX-UHFFFAOYSA-N 0.000 description 1
- MEXYDEMLZDRPMD-UHFFFAOYSA-N methyl 3-[2-(2-methoxyethylamino)-6-methylpyrimidin-4-yl]benzoate Chemical compound COCCNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 MEXYDEMLZDRPMD-UHFFFAOYSA-N 0.000 description 1
- WFHIGNDVSVSHMV-UHFFFAOYSA-N methyl 3-[2-(dimethylamino)-6-methylpyrimidin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N=C(C)C=2)N(C)C)=C1 WFHIGNDVSVSHMV-UHFFFAOYSA-N 0.000 description 1
- COZADSLTQGYNMK-UHFFFAOYSA-N methyl 3-[2-(hydroxymethyl)-6-methylpyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(CO)N=C(C)C=2)=C1 COZADSLTQGYNMK-UHFFFAOYSA-N 0.000 description 1
- DPKFMXPSGWFMNF-UHFFFAOYSA-N methyl 3-[2-(hydroxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(CO)N=CC=2)=C1 DPKFMXPSGWFMNF-UHFFFAOYSA-N 0.000 description 1
- HQEWXXXBMQMFGM-UHFFFAOYSA-N methyl 3-[6-(2-methoxyethylamino)pyrimidin-4-yl]benzoate Chemical compound C1=NC(NCCOC)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 HQEWXXXBMQMFGM-UHFFFAOYSA-N 0.000 description 1
- DDGIMUOQGSBPPV-UHFFFAOYSA-N methyl 3-[6-(methylamino)pyrimidin-4-yl]benzoate Chemical compound C1=NC(NC)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 DDGIMUOQGSBPPV-UHFFFAOYSA-N 0.000 description 1
- FOCFAZDUCUHPMH-UHFFFAOYSA-N methyl 3-[6-methyl-2-(methylamino)pyrimidin-4-yl]benzoate Chemical compound CNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 FOCFAZDUCUHPMH-UHFFFAOYSA-N 0.000 description 1
- MXLYAEPCQSMXEM-UHFFFAOYSA-N methyl 3-[6-methyl-2-[2-(oxan-2-yloxy)ethylamino]pyrimidin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(NCCOC3OCCCC3)N=C(C)C=2)=C1 MXLYAEPCQSMXEM-UHFFFAOYSA-N 0.000 description 1
- DGMXBVBBCRYAMC-UHFFFAOYSA-N methyl 3-pyridazin-3-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC=CC=2)=C1 DGMXBVBBCRYAMC-UHFFFAOYSA-N 0.000 description 1
- SDICQYDWUUZNSN-UHFFFAOYSA-N methyl 3-pyridazin-4-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2C=NN=CC=2)=C1 SDICQYDWUUZNSN-UHFFFAOYSA-N 0.000 description 1
- IOJFNHUNCBUINL-UHFFFAOYSA-N methyl 3-pyrimidin-2-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=CC=CN=2)=C1 IOJFNHUNCBUINL-UHFFFAOYSA-N 0.000 description 1
- IUJPGEFKXSUZTK-UHFFFAOYSA-N methyl 3-pyrimidin-4-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=CN=CC=2)=C1 IUJPGEFKXSUZTK-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- IXWBEJQARFKXJY-UHFFFAOYSA-N n-(diacetamidomethyl)acetamide Chemical compound CC(=O)NC(NC(C)=O)NC(C)=O IXWBEJQARFKXJY-UHFFFAOYSA-N 0.000 description 1
- HNPCDFJZADHNHD-UHFFFAOYSA-N n-(diformamidomethyl)formamide Chemical compound O=CNC(NC=O)NC=O HNPCDFJZADHNHD-UHFFFAOYSA-N 0.000 description 1
- MSWBHPCGEQZSGS-UHFFFAOYSA-N n-[4-methyl-2-nitro-3-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(C(F)(F)F)=C1[N+]([O-])=O MSWBHPCGEQZSGS-UHFFFAOYSA-N 0.000 description 1
- YCWKZLXTHMGYAO-UHFFFAOYSA-N n-methylcyclopropanamine;hydrochloride Chemical compound Cl.CNC1CC1 YCWKZLXTHMGYAO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- WVUCPRGADMCTBN-UHFFFAOYSA-M potassium;3-ethoxy-3-oxopropanoate Chemical compound [K+].CCOC(=O)CC([O-])=O WVUCPRGADMCTBN-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010839 reverse transcription Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 210000002265 sensory receptor cell Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 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 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Substances [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YINDUFNJIBDMBG-UHFFFAOYSA-N tert-butyl 2-(3-pyridin-3-ylphenyl)propanoate Chemical compound C(C)(C)(C)OC(C(C)C1=CC(=CC=C1)C=1C=NC=CC=1)=O YINDUFNJIBDMBG-UHFFFAOYSA-N 0.000 description 1
- CBFXDNPICGIUQW-UHFFFAOYSA-N tert-butyl 3-[2-(2-methylpyridin-4-yl)pyridin-4-yl]-3-oxopropanoate Chemical compound C1=NC(C)=CC(C=2N=CC=C(C=2)C(=O)CC(=O)OC(C)(C)C)=C1 CBFXDNPICGIUQW-UHFFFAOYSA-N 0.000 description 1
- XCLYJUTTYCFBTK-UHFFFAOYSA-N tert-butyl 3-[3-(2-amino-6-methylpyrimidin-4-yl)phenyl]-3-oxopropanoate Chemical compound NC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 XCLYJUTTYCFBTK-UHFFFAOYSA-N 0.000 description 1
- QNYKTIBNDKKCER-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpyrimidin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC1=NC=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 QNYKTIBNDKKCER-UHFFFAOYSA-N 0.000 description 1
- VTHAHUZLRGYTTR-UHFFFAOYSA-N tert-butyl 3-[3-(3-methyl-1,2,4-triazin-6-yl)phenyl]-3-oxopropanoate Chemical compound N1=NC(C)=NC=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 VTHAHUZLRGYTTR-UHFFFAOYSA-N 0.000 description 1
- PVVAMBBCLKEPCQ-UHFFFAOYSA-N tert-butyl 3-[3-(5,6-dimethyl-1,2,4-triazin-3-yl)phenyl]-3-oxopropanoate Chemical compound N1=C(C)C(C)=NN=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 PVVAMBBCLKEPCQ-UHFFFAOYSA-N 0.000 description 1
- GVSYZOLMZXQDIP-UHFFFAOYSA-N tert-butyl 3-[3-(6-aminopyridin-3-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NC(N)=CC=2)=C1 GVSYZOLMZXQDIP-UHFFFAOYSA-N 0.000 description 1
- TYPORPDTTLXGQY-UHFFFAOYSA-N tert-butyl 3-[3-(6-aminopyrimidin-4-yl)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2N=CN=C(N)C=2)=C1 TYPORPDTTLXGQY-UHFFFAOYSA-N 0.000 description 1
- TWTQPQTZOSMEQJ-UHFFFAOYSA-N tert-butyl 3-[3-(6-methylpyridin-2-yl)phenyl]-3-oxopropanoate Chemical compound CC1=CC=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 TWTQPQTZOSMEQJ-UHFFFAOYSA-N 0.000 description 1
- JUCXDMIFZCZHPQ-UHFFFAOYSA-N tert-butyl 3-[3-(6-methylpyrimidin-4-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 JUCXDMIFZCZHPQ-UHFFFAOYSA-N 0.000 description 1
- VEGBWQVIHPIADF-UHFFFAOYSA-N tert-butyl 3-[3-[2-(2-hydroxyethylamino)-6-methylpyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound OCCNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 VEGBWQVIHPIADF-UHFFFAOYSA-N 0.000 description 1
- GQCIPCOVTBUBPG-UHFFFAOYSA-N tert-butyl 3-[3-[2-(2-methoxyethylamino)-6-methylpyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound COCCNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 GQCIPCOVTBUBPG-UHFFFAOYSA-N 0.000 description 1
- GEDJIAVQNPEMKY-UHFFFAOYSA-N tert-butyl 3-[3-[2-(dimethylamino)-6-methylpyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound CN(C)C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 GEDJIAVQNPEMKY-UHFFFAOYSA-N 0.000 description 1
- UJBVZNVHLIAURS-UHFFFAOYSA-N tert-butyl 3-[3-[6-(2-methoxyethylamino)pyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound C1=NC(NCCOC)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 UJBVZNVHLIAURS-UHFFFAOYSA-N 0.000 description 1
- RJJKENRDTJXFOP-UHFFFAOYSA-N tert-butyl 3-[3-[6-(dimethylamino)pyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound C1=NC(N(C)C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 RJJKENRDTJXFOP-UHFFFAOYSA-N 0.000 description 1
- DPJGGJGAFWKCPC-UHFFFAOYSA-N tert-butyl 3-[3-[6-(methylamino)pyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound C1=NC(NC)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 DPJGGJGAFWKCPC-UHFFFAOYSA-N 0.000 description 1
- FRFQWRUPTGAKSW-UHFFFAOYSA-N tert-butyl 3-[3-[6-methyl-2-(methylamino)pyrimidin-4-yl]phenyl]-3-oxopropanoate Chemical compound CNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=N1 FRFQWRUPTGAKSW-UHFFFAOYSA-N 0.000 description 1
- GTURNVMQYRWABU-UHFFFAOYSA-N tert-butyl 3-oxo-3-(2-pyridin-4-ylpyridin-4-yl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=NC(C=2C=CN=CC=2)=C1 GTURNVMQYRWABU-UHFFFAOYSA-N 0.000 description 1
- ALABSMQGQJARFF-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyrimidin-4-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2N=CN=CC=2)=C1 ALABSMQGQJARFF-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- QVQTWAWBOWEOAQ-UHFFFAOYSA-N tert-butyl 3-oxobutanoate;magnesium Chemical compound [Mg].CC(=O)CC(=O)OC(C)(C)C QVQTWAWBOWEOAQ-UHFFFAOYSA-N 0.000 description 1
- KEXMDZTWGHPURR-UHFFFAOYSA-N tert-butyl N-[5-methoxy-2-nitro-4-(trifluoromethyl)phenyl]carbamate Chemical compound C(C)(C)(C)OC(NC1=C(C=C(C(=C1)OC)C(F)(F)F)[N+](=O)[O-])=O.C(C)(C)(C)OC(NC1=C(C=C(C(=C1)OC)C(F)(F)F)[N+](=O)[O-])=O KEXMDZTWGHPURR-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- XMYXDMJZHVRYKZ-UHFFFAOYSA-N tert-butyl n-(4-ethynyl-2-nitrophenyl)carbamate Chemical class CC(C)(C)OC(=O)NC1=CC=C(C#C)C=C1[N+]([O-])=O XMYXDMJZHVRYKZ-UHFFFAOYSA-N 0.000 description 1
- PXCREFJJZMYUBE-UHFFFAOYSA-N tert-butyl n-(5-chloro-4-iodo-2-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(I)C=C1[N+]([O-])=O PXCREFJJZMYUBE-UHFFFAOYSA-N 0.000 description 1
- OXYOVPMDYQIOJP-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2,3-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1C OXYOVPMDYQIOJP-UHFFFAOYSA-N 0.000 description 1
- PVHJZWMCQJHKPR-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2,3-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(OCC(F)(F)F)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1C PVHJZWMCQJHKPR-UHFFFAOYSA-N 0.000 description 1
- ZPMOASRHQJUYQI-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(OCC(F)(F)F)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 ZPMOASRHQJUYQI-UHFFFAOYSA-N 0.000 description 1
- PRIQPPQWJSNNPD-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-ethoxy-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=C(C)C=2)=C1 PRIQPPQWJSNNPD-UHFFFAOYSA-N 0.000 description 1
- XHHBAOSGAUPSDD-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-propoxy-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=C(C)C=2)=C1 XHHBAOSGAUPSDD-UHFFFAOYSA-N 0.000 description 1
- IMWFWFGJLJXNCI-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2-cyanopyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(2-methoxyethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCCOC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(N=CC=2)C#N)=C1 IMWFWFGJLJXNCI-UHFFFAOYSA-N 0.000 description 1
- BQIUGFNNXUEOFE-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(OCC(F)(F)F)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 BQIUGFNNXUEOFE-UHFFFAOYSA-N 0.000 description 1
- VYJSUUDJBHZGSC-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-(5-ethyl-2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CCC1=CN=C(C)C=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC(OCC(F)(F)F)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 VYJSUUDJBHZGSC-UHFFFAOYSA-N 0.000 description 1
- SBIXCKDHMACYQE-UHFFFAOYSA-N tert-butyl n-[2-[[3-[3-[6-(dimethylamino)pyridin-3-yl]phenyl]-3-oxopropanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=CC(C(=O)CC(=O)NC=2C(=CC(OCC(F)(F)F)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 SBIXCKDHMACYQE-UHFFFAOYSA-N 0.000 description 1
- JZILLAYPTWDNCT-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-4-pyrrol-1-ylphenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N2C=CC=C2)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CN=CC=N1 JZILLAYPTWDNCT-UHFFFAOYSA-N 0.000 description 1
- NUKARNIDMBSYJL-UHFFFAOYSA-N tert-butyl n-[2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 NUKARNIDMBSYJL-UHFFFAOYSA-N 0.000 description 1
- VZQQUUOWRMHQPG-UHFFFAOYSA-N tert-butyl n-[2-amino-4-chloro-5-[methyl(propan-2-yl)amino]phenyl]carbamate Chemical compound CC(C)N(C)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1Cl VZQQUUOWRMHQPG-UHFFFAOYSA-N 0.000 description 1
- OWDYVWOBISSUIH-UHFFFAOYSA-N tert-butyl n-[2-nitro-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC(F)(F)F)=C(C(F)(F)F)C=C1[N+]([O-])=O OWDYVWOBISSUIH-UHFFFAOYSA-N 0.000 description 1
- IKWPHCMXIKWDMJ-UHFFFAOYSA-N tert-butyl n-[2-nitro-5-(oxan-2-yloxymethyl)-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(COC2OCCCC2)=C1C(F)(F)F IKWPHCMXIKWDMJ-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- VMCZDVOUDACLSE-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(=C(Cl)C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 VMCZDVOUDACLSE-UHFFFAOYSA-N 0.000 description 1
- UNLONZXJUYAWEQ-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC=C(Cl)C=2)NC(=O)OC(C)(C)C)=C1 UNLONZXJUYAWEQ-UHFFFAOYSA-N 0.000 description 1
- UBDQBPWZFXVEKM-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyrazin-2-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=NC=2)=C1 UBDQBPWZFXVEKM-UHFFFAOYSA-N 0.000 description 1
- IECAXQHRBQPPOL-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 IECAXQHRBQPPOL-UHFFFAOYSA-N 0.000 description 1
- ZLTHQALFCFVKDR-UHFFFAOYSA-N tert-butyl n-[4-chloro-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 ZLTHQALFCFVKDR-UHFFFAOYSA-N 0.000 description 1
- LTKKKHAMEKOCBW-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-fluoro-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 LTKKKHAMEKOCBW-UHFFFAOYSA-N 0.000 description 1
- XDLKYPSYEBSFAG-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-fluoro-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(Cl)C=C1NC(=O)CC(=O)C1=CC=CC(C=2C=CN=CC=2)=C1 XDLKYPSYEBSFAG-UHFFFAOYSA-N 0.000 description 1
- BIHJRVDCQMDZMI-UHFFFAOYSA-N tert-butyl n-[4-chloro-5-methyl-2-[[3-oxo-3-(3-pyridin-2-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2N=CC=CC=2)=C1 BIHJRVDCQMDZMI-UHFFFAOYSA-N 0.000 description 1
- QBTMCRKXPQESSF-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-[[3-[3-(6-methylpyrazin-2-yl)phenyl]-3-oxopropanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CN=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(=C(C)C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=N1 QBTMCRKXPQESSF-UHFFFAOYSA-N 0.000 description 1
- IAELFJWLPDDCMQ-UHFFFAOYSA-N tert-butyl n-[4-methyl-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-5-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(C)=CC(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1NC(=O)OC(C)(C)C IAELFJWLPDDCMQ-UHFFFAOYSA-N 0.000 description 1
- YLYQVAJQRLJSAF-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=C(C)N=CC=2)=C1 YLYQVAJQRLJSAF-UHFFFAOYSA-N 0.000 description 1
- YJTVVLXUYKAHBA-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-2-[[3-oxo-3-(3-pyrimidin-5-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC=NC=2)=C1 YJTVVLXUYKAHBA-UHFFFAOYSA-N 0.000 description 1
- LXESDSJTWCYMCF-UHFFFAOYSA-N tert-butyl n-[5-(dimethylamino)-4-(2-fluorophenyl)-2-[[3-oxo-3-(3-pyridin-4-ylphenyl)propanoyl]amino]phenyl]carbamate Chemical compound C1=C(C=2C(=CC=CC=2)F)C(N(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C(C=1)=CC=CC=1C1=CC=NC=C1 LXESDSJTWCYMCF-UHFFFAOYSA-N 0.000 description 1
- PJIWZZUXQDIICJ-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-[[3-[3-(2,6-dimethylpyridin-4-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(Cl)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=C1 PJIWZZUXQDIICJ-UHFFFAOYSA-N 0.000 description 1
- ZRIAALBLUUSZKG-UHFFFAOYSA-N tert-butyl n-[5-ethoxy-2-[[3-[3-(6-ethylpyridin-3-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(OCC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C=2C=NC(CC)=CC=2)=C1 ZRIAALBLUUSZKG-UHFFFAOYSA-N 0.000 description 1
- IIUWOZHRPNWKSC-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-[[3-[3-(6-methylpyrazin-2-yl)phenyl]-3-oxopropanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CN=CC(C=2C=C(C=CC=2)C(=O)CC(=O)NC=2C(=CC(C)=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)=N1 IIUWOZHRPNWKSC-UHFFFAOYSA-N 0.000 description 1
- ABFMOBPAZUCWIK-UHFFFAOYSA-N tert-butyl n-[5-morpholin-4-yl-2-[[3-oxo-3-(3-pyridin-3-ylphenyl)propanoyl]amino]-4-(trifluoromethyl)phenyl]carbamate Chemical compound FC(F)(F)C=1C=C(NC(=O)CC(=O)C=2C=C(C=CC=2)C=2C=NC=CC=2)C(NC(=O)OC(C)(C)C)=CC=1N1CCOCC1 ABFMOBPAZUCWIK-UHFFFAOYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- JZSVFMCORWKUOK-UHFFFAOYSA-N tert-butyl n-phenyl-n-(trifluoromethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(C(F)(F)F)C1=CC=CC=C1 JZSVFMCORWKUOK-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- GTJUPSNUGOBNMF-UHFFFAOYSA-M zinc;cyclopentane;bromide Chemical compound Br[Zn+].C1CC[CH-]C1 GTJUPSNUGOBNMF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02002012 | 2002-02-06 | ||
PCT/EP2003/000859 WO2003066623A1 (en) | 2002-02-06 | 2003-01-28 | Dihydrobenzodiazepin-2-one derivatives for the treatment of neurological disorders |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20043237L NO20043237L (no) | 2004-08-02 |
NO327697B1 true NO327697B1 (no) | 2009-09-14 |
Family
ID=27675598
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20043237A NO327697B1 (no) | 2002-02-06 | 2004-08-02 | Dihydrobenzodiazepin-2-onderivater, farmasoytisk medikament omfattende slike, fremgangsmate for fremstilling av slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdom |
Country Status (31)
Country | Link |
---|---|
US (1) | US6949542B2 (ja) |
EP (1) | EP1474416B1 (ja) |
JP (1) | JP4077411B2 (ja) |
KR (1) | KR20040081486A (ja) |
CN (1) | CN100497333C (ja) |
AR (1) | AR038481A1 (ja) |
AT (1) | ATE374196T1 (ja) |
AU (1) | AU2003205695B8 (ja) |
BR (1) | BR0307474A (ja) |
CA (1) | CA2474219C (ja) |
DE (1) | DE60316538T2 (ja) |
DK (1) | DK1474416T3 (ja) |
ES (1) | ES2294264T3 (ja) |
GT (1) | GT200300028A (ja) |
HK (1) | HK1078858A1 (ja) |
HR (1) | HRP20040678A2 (ja) |
IL (1) | IL163102A (ja) |
MX (1) | MXPA04007516A (ja) |
MY (1) | MY176608A (ja) |
NO (1) | NO327697B1 (ja) |
NZ (1) | NZ534122A (ja) |
PA (1) | PA8565901A1 (ja) |
PE (1) | PE20031011A1 (ja) |
PL (1) | PL372425A1 (ja) |
PT (1) | PT1474416E (ja) |
RU (1) | RU2315764C2 (ja) |
SI (1) | SI1474416T1 (ja) |
TW (1) | TWI326599B (ja) |
UY (1) | UY27654A1 (ja) |
WO (1) | WO2003066623A1 (ja) |
ZA (1) | ZA200406032B (ja) |
Families Citing this family (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ20021663A3 (cs) | 1999-10-15 | 2002-09-11 | F. Hoffmann-La Roche Ag | Nové deriváty benzodiazepinu |
AU2004262897B9 (en) * | 2003-07-25 | 2009-12-17 | F. Hoffmann-La Roche Ag | Combination of mGluR2 antagonist and ache inhibitor for treatment of acute and/or chronic neurological disorders |
WO2007039439A1 (en) | 2005-09-27 | 2007-04-12 | F.Hoffmann-La Roche Ag | Oxadiazolyl pyrazolo-pyrimidines as mglur2 antagonists |
TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | 1,4-二取代之3-氰基-吡啶酮衍生物及其作為mGluR2-受體之正向異位性調節劑之用途 |
TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
CN101657432B (zh) * | 2007-04-19 | 2013-04-10 | 弗·哈夫曼-拉罗切有限公司 | 二氢-苯并[b][1,4]二氮杂*-2-酮磺酰胺衍生物 |
CA2697167C (en) | 2007-08-27 | 2013-07-16 | F. Hoffmann-La Roche Ag | Benzimidazole derivatives used as fxr agonists |
TW200927731A (en) | 2007-09-14 | 2009-07-01 | Ortho Mcneil Janssen Pharm | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
WO2009033702A1 (en) | 2007-09-14 | 2009-03-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
PT2203439E (pt) | 2007-09-14 | 2011-02-11 | Ortho Mcneil Janssen Pharm | 4-fenil-3,4,5,6-tetra-hidro-2h,1'h-[1,4']bipiridinil-2'- onas 1',3'-dissubstituídas |
EP2220083B1 (en) | 2007-11-14 | 2017-07-19 | Janssen Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CN102238950B (zh) | 2008-08-04 | 2014-05-07 | Chdi基金会股份有限公司 | 某些犬尿氨酸-3-单加氧酶抑制剂、药物组合物以及使用方法 |
EP2344470B1 (en) | 2008-09-02 | 2013-11-06 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
AU2009304293B2 (en) | 2008-10-16 | 2012-04-26 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
CN102232074B (zh) | 2008-11-28 | 2014-12-03 | 奥梅-杨森制药有限公司 | 作为代谢性谷氨酸盐受体调节剂的吲哚和苯并噁嗪衍生物 |
ES2409006T3 (es) | 2009-05-12 | 2013-06-24 | Janssen Pharmaceuticals Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2 |
MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CA2760741C (en) | 2009-05-12 | 2018-05-01 | Addex Pharma S.A. | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
TWI481601B (zh) | 2009-08-21 | 2015-04-21 | Otsuka Pharma Co Ltd | 含氮化合物及藥學組成物 |
RU2553676C2 (ru) | 2009-08-21 | 2015-06-20 | Оцука Фармасьютикал Ко., Лтд. | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНОГО БЕНЗО[b][1,4]ДИАЗЕПИН-2,4-ДИОНА |
NZ601547A (en) | 2010-01-25 | 2014-04-30 | Chdi Foundation Inc | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
CA2815002C (en) | 2010-11-08 | 2019-10-22 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CN103298810B (zh) | 2010-11-08 | 2016-03-16 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
JP5852665B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
EP2701699B1 (en) | 2011-04-28 | 2019-10-16 | The Broad Institute, Inc. | Inhibitors of histone deacetylase |
CA2847247C (en) | 2011-08-29 | 2019-10-15 | Sanford-Burnham Medical Research Institute | Benzodiazepinones as modulators of metabotropic glutamate receptor functions and neurological uses thereof |
ES2765805T3 (es) | 2011-08-30 | 2020-06-11 | Chdi Foundation Inc | Inhibidores de kinurenina-3-monoxigenasa, composiciones farmacéuticas y métodos de uso de los mismos |
CN103827095A (zh) | 2011-08-30 | 2014-05-28 | Chdi基金会股份有限公司 | 犬尿氨酸-3-单加氧酶抑制剂、其药物组合物及其使用方法 |
US9790184B2 (en) | 2012-07-27 | 2017-10-17 | The Broad Institute, Inc. | Inhibitors of histone deacetylase |
AU2013336863A1 (en) | 2012-10-23 | 2015-03-19 | F. Hoffmann-La Roche Ag | MGlu2/3 antagonists for the treatment of autistic disorders |
WO2014100438A1 (en) | 2012-12-20 | 2014-06-26 | The Broad Institute, Inc. | Cycloalkenyl hydroxamic acid derivatives and their use as histone deacetylase inhibitors |
JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
KR20200036063A (ko) | 2014-01-21 | 2020-04-06 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
JP6629740B2 (ja) | 2014-01-21 | 2020-01-15 | ヤンセン ファーマシューティカ エヌ.ベー. | 代謝型グルタミン酸作動性受容体サブタイプ2の正のアロステリック調節因子またはオルトステリックアゴニストを含む組み合わせ、およびそれらの使用 |
EP3134089A2 (en) | 2014-04-23 | 2017-03-01 | F. Hoffmann-La Roche AG | Mglu2/3 antagonists for the treatment of intellectual disabilities |
CA2950952C (en) | 2014-06-10 | 2023-01-10 | Sanford-Burnham Medical Research Institute | Metabotropic glutamate receptor negative allosteric modulators (nams) and uses thereof |
BR112017000922A2 (pt) | 2014-07-17 | 2018-01-16 | Chdi Foundation, Inc. | métodos e composições para tratar distúrbios relacionados ao hiv |
JP2017206438A (ja) * | 2014-08-22 | 2017-11-24 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | テトラヒドロイミダゾ[1,5−d][1,4]オキサゼピン化合物(TETRAHYDROIMIDAZO[1,5−d][1,4]OXAZEPINECOMPOUND) |
WO2018019721A1 (en) | 2016-07-26 | 2018-02-01 | Basf Se | Herbicidal pyridine compounds |
WO2018019755A1 (en) | 2016-07-26 | 2018-02-01 | Basf Se | Herbicidal pyridine compounds |
CN110407740A (zh) * | 2019-09-04 | 2019-11-05 | 上海毕得医药科技有限公司 | 一种3-溴-2-乙基吡啶的合成方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0389189B1 (en) * | 1989-03-23 | 1994-05-18 | Pfizer Limited | Diazepine antiallergy agents |
ATE250039T1 (de) | 1999-10-15 | 2003-10-15 | Hoffmann La Roche | Benzodiazepinderivate und deren verwendung als metabotrope glutamatrezeptor antagonisten |
CZ20021663A3 (cs) | 1999-10-15 | 2002-09-11 | F. Hoffmann-La Roche Ag | Nové deriváty benzodiazepinu |
-
2003
- 2003-01-24 US US10/350,713 patent/US6949542B2/en not_active Expired - Lifetime
- 2003-01-28 CN CNB038065452A patent/CN100497333C/zh not_active Expired - Fee Related
- 2003-01-28 ES ES03702549T patent/ES2294264T3/es not_active Expired - Lifetime
- 2003-01-28 BR BR0307474-9A patent/BR0307474A/pt not_active Application Discontinuation
- 2003-01-28 MX MXPA04007516A patent/MXPA04007516A/es active IP Right Grant
- 2003-01-28 WO PCT/EP2003/000859 patent/WO2003066623A1/en active IP Right Grant
- 2003-01-28 KR KR10-2004-7012084A patent/KR20040081486A/ko active Search and Examination
- 2003-01-28 DE DE60316538T patent/DE60316538T2/de not_active Expired - Lifetime
- 2003-01-28 RU RU2004126945/04A patent/RU2315764C2/ru not_active IP Right Cessation
- 2003-01-28 NZ NZ534122A patent/NZ534122A/en not_active IP Right Cessation
- 2003-01-28 EP EP03702549A patent/EP1474416B1/en not_active Expired - Lifetime
- 2003-01-28 CA CA2474219A patent/CA2474219C/en not_active Expired - Fee Related
- 2003-01-28 DK DK03702549T patent/DK1474416T3/da active
- 2003-01-28 AT AT03702549T patent/ATE374196T1/de active
- 2003-01-28 PL PL03372425A patent/PL372425A1/xx not_active Application Discontinuation
- 2003-01-28 AU AU2003205695A patent/AU2003205695B8/en not_active Ceased
- 2003-01-28 JP JP2003565996A patent/JP4077411B2/ja not_active Expired - Fee Related
- 2003-01-28 PT PT03702549T patent/PT1474416E/pt unknown
- 2003-01-28 SI SI200331034T patent/SI1474416T1/sl unknown
- 2003-01-30 TW TW092102234A patent/TWI326599B/zh active
- 2003-02-03 PE PE2003000122A patent/PE20031011A1/es not_active Application Discontinuation
- 2003-02-03 GT GT200300028A patent/GT200300028A/es unknown
- 2003-02-04 AR ARP030100334A patent/AR038481A1/es unknown
- 2003-02-05 PA PA20038565901A patent/PA8565901A1/es unknown
- 2003-02-05 UY UY27654A patent/UY27654A1/es not_active Application Discontinuation
- 2003-02-05 MY MYPI20030378A patent/MY176608A/en unknown
-
2004
- 2004-07-19 IL IL163102A patent/IL163102A/en not_active IP Right Cessation
- 2004-07-23 HR HR20040678A patent/HRP20040678A2/hr not_active Application Discontinuation
- 2004-07-28 ZA ZA200406032A patent/ZA200406032B/en unknown
- 2004-08-02 NO NO20043237A patent/NO327697B1/no not_active IP Right Cessation
-
2005
- 2005-11-25 HK HK05110731.8A patent/HK1078858A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO327697B1 (no) | Dihydrobenzodiazepin-2-onderivater, farmasoytisk medikament omfattende slike, fremgangsmate for fremstilling av slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdom | |
TWI834784B (zh) | 經取代之吡唑并嘧啶及經取代之嘌呤以及其作為泛素特異性加工蛋白酶1 ( u s p 1 ) 抑制劑的用途 | |
EP1379511B1 (en) | DIHYDRO-BENZO (b) (1, 4) DIAZEPIN-2-ONE DERIVATIVES AS MGLUR2 ANTAGONISTS II | |
EP1379522B1 (en) | DIHYDRO-BENZO(b)(1,4)DIAZEPIN-2-ONE DERIVATIVES AS MGLUR2 ANTAGONISTS I | |
AU2002312788A1 (en) | Dihydro-benzo [b] [1, 4] diazepin-2-one derivatives as mGluR2 antagonists II | |
EP3049391B1 (en) | Indole and indazole derivatives | |
NO326518B1 (no) | Pyrazolderivater og anvendelse derav, samt farmasoytisk sammensetning | |
JP7311583B2 (ja) | Gaba受容体モジュレーターとしてのジフルオロメチル-フェニルトリアゾール | |
AU2002310912A1 (en) | Dihydro-benzo[b][1,4]diazepin-2-one derivatives as mGluR2 antagonists I | |
AU2010224523A2 (en) | Novel anti-inflammatory agents | |
EP2300435A2 (en) | Heterocyclic compounds as factor ixa inhibitors | |
CN117836294A (zh) | 含芳环类生物拮抗剂、其制备方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |