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

Info

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

2002-02-06

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• 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
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• 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
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• 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
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• 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
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• 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
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• 238000005292 vacuum distillation Methods 0.000 description 1
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