JP2015529192A5

JP2015529192A5 -

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Publication number: JP2015529192A5
Authority: JP; Japan
Prior art keywords: alkyl; dihydro; benzodiazepine; carboxamide; phenyl
Prior art date: 2013-08-13
Legal status : Granted

Application number

JP2015526970A

Other languages

English (en)

Japanese (ja)

Other versions

JP6333251B2 (ja

JP2015529192A (ja

Filing date

2013-08-13

Publication date

2018-02-08

2013-08-13 Application filed filed Critical

2013-08-13 Priority claimed from PCT/EP2013/066931 external-priority patent/WO2014026997A1/de

2015-10-05 Publication of JP2015529192A publication Critical patent/JP2015529192A/ja

2018-02-08 Publication of JP2015529192A5 publication Critical patent/JP2015529192A5/ja

2018-05-30 Application granted granted Critical

2018-05-30 Publication of JP6333251B2 publication Critical patent/JP6333251B2/ja

Status Expired - Fee Related legal-status Critical Current

2033-08-13 Anticipated expiration legal-status Critical

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-1 cyano, carboxyl Chemical group 0.000 claims description 336
125000006413 ring segment Chemical group 0.000 claims description 250
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 209
229910052736 halogen Inorganic materials 0.000 claims description 196
150000002367 halogens Chemical group 0.000 claims description 196
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 164
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 158
125000001424 substituent group Chemical group 0.000 claims description 157
229910052739 hydrogen Inorganic materials 0.000 claims description 145
239000001257 hydrogen Substances 0.000 claims description 145
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 136
125000005843 halogen group Chemical group 0.000 claims description 108
125000004093 cyano group Chemical group *C#N 0.000 claims description 104
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 81
229910052801 chlorine Inorganic materials 0.000 claims description 78
239000000460 chlorine Substances 0.000 claims description 78
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 73
229910052731 fluorine Inorganic materials 0.000 claims description 67
239000011737 fluorine Substances 0.000 claims description 67
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 65
125000001153 fluoro group Chemical group F* 0.000 claims description 62
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
125000004076 pyridyl group Chemical group 0.000 claims description 58
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 55
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 55
229910052794 bromium Inorganic materials 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 44
125000000623 heterocyclic group Chemical group 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 44
239000012453 solvate Substances 0.000 claims description 44
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 39
125000004043 oxo group Chemical group O=* 0.000 claims description 38
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 37
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 32
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
125000004193 piperazinyl group Chemical group 0.000 claims description 29
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 28
125000002757 morpholinyl group Chemical group 0.000 claims description 28
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000004430 oxygen atom Chemical group O* 0.000 claims description 22
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 21
125000003386 piperidinyl group Chemical group 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 17
125000002950 monocyclic group Chemical group 0.000 claims description 16
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 15
125000005059 halophenyl group Chemical group 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 11
125000006379 fluoropyridyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000003226 pyrazolyl group Chemical group 0.000 claims description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 6
125000006317 cyclopropyl amino group Chemical group 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 65
150000003857 carboxamides Chemical class 0.000 claims 53
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
125000004568 thiomorpholinyl group Chemical group 0.000 claims 9
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 8
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 7
125000000842 isoxazolyl group Chemical group 0.000 claims 7
125000000160 oxazolidinyl group Chemical group 0.000 claims 7
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 7
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 6
125000001425 triazolyl group Chemical group 0.000 claims 6
125000002393 azetidinyl group Chemical group 0.000 claims 5
125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 5
125000004432 carbon atom Chemical group C* 0.000 claims 5
125000001309 chloro group Chemical group Cl* 0.000 claims 5
SESYXUWPTXSJBV-UHFFFAOYSA-N [amino(hydroxy)-lambda3-chloranyl]formonitrile Chemical compound NCl(O)C#N SESYXUWPTXSJBV-UHFFFAOYSA-N 0.000 claims 4
125000005959 diazepanyl group Chemical group 0.000 claims 4
201000010099 disease Diseases 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
125000001207 fluorophenyl group Chemical group 0.000 claims 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
125000001984 thiazolidinyl group Chemical group 0.000 claims 4
PJOUURZOYJMYPA-UHFFFAOYSA-N OClC#N Chemical compound OClC#N PJOUURZOYJMYPA-UHFFFAOYSA-N 0.000 claims 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
125000004965 chloroalkyl group Chemical group 0.000 claims 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
125000002883 imidazolyl group Chemical group 0.000 claims 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
125000001715 oxadiazolyl group Chemical group 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
125000000714 pyrimidinyl group Chemical group 0.000 claims 3
125000000168 pyrrolyl group Chemical group 0.000 claims 3
125000003831 tetrazolyl group Chemical group 0.000 claims 3
125000000335 thiazolyl group Chemical group 0.000 claims 3
125000001544 thienyl group Chemical group 0.000 claims 3
JAEQPUOTZYKLOU-KRWDZBQOSA-N (4S)-1-[4-(4-hydroxy-4-methylpiperidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound OC1(CCN(CC1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C JAEQPUOTZYKLOU-KRWDZBQOSA-N 0.000 claims 2
JAEQPUOTZYKLOU-QGZVFWFLSA-N (4r)-1-[4-(4-hydroxy-4-methylpiperidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1CCC(C)(O)CC1 JAEQPUOTZYKLOU-QGZVFWFLSA-N 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
JAEQPUOTZYKLOU-UHFFFAOYSA-N 1-[4-(4-hydroxy-4-methylpiperidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCC(C)(O)CC1 JAEQPUOTZYKLOU-UHFFFAOYSA-N 0.000 claims 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
UVCCMWQEFMGGFL-UHFFFAOYSA-N 7,8-dimethoxy-1-[4-(3-methoxyazetidin-1-yl)phenyl]-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CC(OC)C1 UVCCMWQEFMGGFL-UHFFFAOYSA-N 0.000 claims 2
HUBNGODXYNKURM-UHFFFAOYSA-N 7-chloro-1-(4-chlorophenyl)-n,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC(F)(F)F)=C(Cl)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 HUBNGODXYNKURM-UHFFFAOYSA-N 0.000 claims 2
239000005973 Carvone Substances 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
125000006001 difluoroethyl group Chemical group 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
239000000203 mixture Substances 0.000 claims 2
FJUKBDRJUMGMMY-GFCCVEGCSA-N (4R)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC)c(OC)cc2C[C@H]1C FJUKBDRJUMGMMY-GFCCVEGCSA-N 0.000 claims 1
XAUMIWJFGTVNKQ-CYBMUJFWSA-N (4R)-1-(4-chlorophenyl)-N,4,8-trimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C=C2)C)C)C(=O)NC XAUMIWJFGTVNKQ-CYBMUJFWSA-N 0.000 claims 1
MVAHTFLZMOQYDC-LLVKDONJSA-N (4R)-1-(4-chlorophenyl)-N,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C=C2)OC(F)(F)F)C)C(=O)NC MVAHTFLZMOQYDC-LLVKDONJSA-N 0.000 claims 1
JAPYRZRQVTWQPV-OAHLLOKOSA-N (4R)-1-(4-chlorophenyl)-N,4-dimethyl-8-morpholin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C=C2)N2CCOCC2)C)C(=O)NC JAPYRZRQVTWQPV-OAHLLOKOSA-N 0.000 claims 1
LVOZKSSVIPZABA-CQSZACIVSA-N (4R)-1-[4-(2,4-dimethyl-1,3-thiazol-5-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC=1SC(=C(N1)C)C1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC LVOZKSSVIPZABA-CQSZACIVSA-N 0.000 claims 1
LUFRZKPVUCTMLL-CQSZACIVSA-N (4R)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C LUFRZKPVUCTMLL-CQSZACIVSA-N 0.000 claims 1
JVTTUZQEDRLPJQ-QGZVFWFLSA-N (4R)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4-dimethyl-8-morpholin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(C2=CC=C(C=C2)C2=C(C)ON=C2C)C2=C(C[C@H]1C)C=CC(=C2)N1CCOCC1 JVTTUZQEDRLPJQ-QGZVFWFLSA-N 0.000 claims 1
ZDRURUMITWYFTN-CQSZACIVSA-N (4R)-1-[4-(3-fluoroazetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1CN(C1)C1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ZDRURUMITWYFTN-CQSZACIVSA-N 0.000 claims 1
SRUSJOIHVSHPAK-OAHLLOKOSA-N (4R)-1-[4-(azetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N1(CCC1)C1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC SRUSJOIHVSHPAK-OAHLLOKOSA-N 0.000 claims 1
ONNQNUAUYFRDQK-GOSISDBHSA-N (4R)-1-[4-[3-(4-fluorophenyl)pyrazol-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=CC=C(C=C1)C1=NN(C=C1)C1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ONNQNUAUYFRDQK-GOSISDBHSA-N 0.000 claims 1
RMQQVUOTOWBNTB-GOSISDBHSA-N (4R)-1-[4-[4-(dimethylamino)piperidin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CN(C1CCN(CC1)C1=CC=C(C=C1)C1=NN([C@@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C RMQQVUOTOWBNTB-GOSISDBHSA-N 0.000 claims 1
NPQSRNGURRYZDG-MRXNPFEDSA-N (4R)-7,8-dimethoxy-N,4-dimethyl-1-(4-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)N2CCOCC2)C(=O)NC)C)C1)OC NPQSRNGURRYZDG-MRXNPFEDSA-N 0.000 claims 1
JGCATJICLCFSEV-MRXNPFEDSA-N (4R)-7,8-dimethoxy-N,4-dimethyl-1-[4-(4-methyl-2-oxopiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)N2C(CN(CC2)C)=O)C(=O)NC)C)C1)OC JGCATJICLCFSEV-MRXNPFEDSA-N 0.000 claims 1
VNWOTAZEIJOBBW-QGZVFWFLSA-N (4R)-7,8-dimethoxy-N,4-dimethyl-1-[4-[4-(methylcarbamoyl)piperidin-1-yl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)N2CCC(CC2)C(NC)=O)C(=O)NC)C)C1)OC VNWOTAZEIJOBBW-QGZVFWFLSA-N 0.000 claims 1
QQENNSOEIIPWGC-CYBMUJFWSA-N (4R)-7-(difluoromethoxy)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC(OC=1C(=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)C=2C(=NOC2C)C)C(=O)NC)C)C1)OC)F QQENNSOEIIPWGC-CYBMUJFWSA-N 0.000 claims 1
CSDIIHOAJVAHHD-MRXNPFEDSA-N (4R)-7-(difluoromethoxy)-8-methoxy-N,4-dimethyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC(OC=1C(=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)N2CCN(CC2)C)C(=O)NC)C)C1)OC)F CSDIIHOAJVAHHD-MRXNPFEDSA-N 0.000 claims 1
RJFPYIZAIZXRQR-GFCCVEGCSA-N (4R)-7-chloro-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC=1C(=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)C=2C(=NOC2C)C)C(=O)NC)C)C1)OC(F)(F)F RJFPYIZAIZXRQR-GFCCVEGCSA-N 0.000 claims 1
SNKUBVXLWUOEPC-LLVKDONJSA-N (4R)-8-bromo-1-(4-chlorophenyl)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound BrC1=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)Cl)C(=O)NC)C)C=C1 SNKUBVXLWUOEPC-LLVKDONJSA-N 0.000 claims 1
VVMJEFWIDBTRQV-LLVKDONJSA-N (4R)-8-chloro-1-(4-chlorophenyl)-7-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(Cl)c(OC)cc2C[C@H]1C VVMJEFWIDBTRQV-LLVKDONJSA-N 0.000 claims 1
RHZBQXXNYNUUAA-CYBMUJFWSA-N (4R)-8-chloro-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC2=C(C[C@H](N(N=C2C2=CC=C(C=C2)C=2C(=NOC2C)C)C(=O)NC)C)C=C1OC RHZBQXXNYNUUAA-CYBMUJFWSA-N 0.000 claims 1
PHZKFXUAHTVWFV-CQSZACIVSA-N (4R)-8-tert-butyl-1-(4-chlorophenyl)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(ccc2C[C@H]1C)C(C)(C)C PHZKFXUAHTVWFV-CQSZACIVSA-N 0.000 claims 1
KPBTZKZVLXSZMJ-MRXNPFEDSA-N (4R)-N,4-dimethyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(cc2)N2CCN(C)CC2)c2cc(OC(F)(F)F)ccc2C[C@H]1C KPBTZKZVLXSZMJ-MRXNPFEDSA-N 0.000 claims 1
FJUKBDRJUMGMMY-LBPRGKRZSA-N (4S)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC)c(OC)cc2C[C@@H]1C FJUKBDRJUMGMMY-LBPRGKRZSA-N 0.000 claims 1
VEIXXVJKOAJEOO-LBPRGKRZSA-N (4S)-1-(4-bromophenyl)-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC)ccc2C[C@@H]1C VEIXXVJKOAJEOO-LBPRGKRZSA-N 0.000 claims 1
XAUMIWJFGTVNKQ-ZDUSSCGKSA-N (4S)-1-(4-chlorophenyl)-N,4,8-trimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C=C2)C)C)C(=O)NC XAUMIWJFGTVNKQ-ZDUSSCGKSA-N 0.000 claims 1
MVAHTFLZMOQYDC-NSHDSACASA-N (4S)-1-(4-chlorophenyl)-N,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C=C2)OC(F)(F)F)C)C(=O)NC MVAHTFLZMOQYDC-NSHDSACASA-N 0.000 claims 1
BGOGYMGFOKKAOF-IBGZPJMESA-N (4S)-1-(4-chlorophenyl)-N,4-dimethyl-8-[3-(4-methylpiperazin-1-yl)propoxy]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C=C2)OCCCN2CCN(CC2)C)C)C(=O)NC BGOGYMGFOKKAOF-IBGZPJMESA-N 0.000 claims 1
JAPYRZRQVTWQPV-HNNXBMFYSA-N (4S)-1-(4-chlorophenyl)-N,4-dimethyl-8-morpholin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C=C2)N2CCOCC2)C)C(=O)NC JAPYRZRQVTWQPV-HNNXBMFYSA-N 0.000 claims 1
LVOZKSSVIPZABA-AWEZNQCLSA-N (4S)-1-[4-(2,4-dimethyl-1,3-thiazol-5-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC=1SC(=C(N1)C)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC LVOZKSSVIPZABA-AWEZNQCLSA-N 0.000 claims 1
LUFRZKPVUCTMLL-AWEZNQCLSA-N (4S)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C LUFRZKPVUCTMLL-AWEZNQCLSA-N 0.000 claims 1
ZDRURUMITWYFTN-AWEZNQCLSA-N (4S)-1-[4-(3-fluoroazetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1CN(C1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ZDRURUMITWYFTN-AWEZNQCLSA-N 0.000 claims 1
VRRWTCUDSZFECD-HNNXBMFYSA-N (4S)-1-[4-(3-hydroxy-3-methylazetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound OC1(CN(C1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C VRRWTCUDSZFECD-HNNXBMFYSA-N 0.000 claims 1
NAMYBRJRBNIRIQ-FQEVSTJZSA-N (4S)-1-[4-(5-cyclopropyl-3-phenylpyrazol-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C1(CC1)C1=CC(=NN1C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C2=CC=CC=C2 NAMYBRJRBNIRIQ-FQEVSTJZSA-N 0.000 claims 1
SRUSJOIHVSHPAK-HNNXBMFYSA-N (4S)-1-[4-(azetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N1(CCC1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC SRUSJOIHVSHPAK-HNNXBMFYSA-N 0.000 claims 1
PGTQCUTXMNXDNK-OKZBNKHCSA-N (4S)-1-[4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(cc2)N2C[C@H](C)O[C@H](C)C2)c2cc(OC)c(OC)cc2C[C@@H]1C PGTQCUTXMNXDNK-OKZBNKHCSA-N 0.000 claims 1
KUXDMRAONOYXDM-KXBFYZLASA-N (4S)-1-[4-[(3S)-3-hydroxypyrrolidin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound O[C@@H]1CN(CC1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC KUXDMRAONOYXDM-KXBFYZLASA-N 0.000 claims 1
ONNQNUAUYFRDQK-SFHVURJKSA-N (4S)-1-[4-[3-(4-fluorophenyl)pyrazol-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=CC=C(C=C1)C1=NN(C=C1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ONNQNUAUYFRDQK-SFHVURJKSA-N 0.000 claims 1
RMQQVUOTOWBNTB-SFHVURJKSA-N (4S)-1-[4-[4-(dimethylamino)piperidin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CN(C1CCN(CC1)C1=CC=C(C=C1)C1=NN([C@H](CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C RMQQVUOTOWBNTB-SFHVURJKSA-N 0.000 claims 1
GTCPNBUMUTYGMM-IBGZPJMESA-N (4S)-4-ethyl-7,8-dimethoxy-N-methyl-1-(4-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC[C@H]1Cc2cc(OC)c(OC)cc2C(=NN1C(=O)NC)c1ccc(cc1)N1CCOCC1 GTCPNBUMUTYGMM-IBGZPJMESA-N 0.000 claims 1
NPQSRNGURRYZDG-INIZCTEOSA-N (4S)-7,8-dimethoxy-N,4-dimethyl-1-(4-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)N2CCOCC2)C(=O)NC)C)C1)OC NPQSRNGURRYZDG-INIZCTEOSA-N 0.000 claims 1
UTHKZGZVFZXNSZ-INIZCTEOSA-N (4S)-7,8-dimethoxy-N,4-dimethyl-1-(4-piperazin-1-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)N2CCNCC2)C(=O)NC)C)C1)OC UTHKZGZVFZXNSZ-INIZCTEOSA-N 0.000 claims 1
AUSGEPFKFFOZTQ-AWEZNQCLSA-N (4S)-7,8-dimethoxy-N,4-dimethyl-1-[4-(1-methyltriazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)C=2N=NN(C2)C)C(=O)NC)C)C1)OC AUSGEPFKFFOZTQ-AWEZNQCLSA-N 0.000 claims 1
MVBCISMWUBFARK-IBGZPJMESA-N (4S)-7,8-dimethoxy-N,4-dimethyl-1-[4-(5-methyl-3-phenylpyrazol-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)N2N=C(C=C2C)C2=CC=CC=C2)C(=O)NC)C)C1)OC MVBCISMWUBFARK-IBGZPJMESA-N 0.000 claims 1
QQENNSOEIIPWGC-ZDUSSCGKSA-N (4S)-7-(difluoromethoxy)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC(OC=1C(=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)C=2C(=NOC2C)C)C(=O)NC)C)C1)OC)F QQENNSOEIIPWGC-ZDUSSCGKSA-N 0.000 claims 1
CSDIIHOAJVAHHD-INIZCTEOSA-N (4S)-7-(difluoromethoxy)-8-methoxy-N,4-dimethyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC(OC=1C(=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)N2CCN(CC2)C)C(=O)NC)C)C1)OC)F CSDIIHOAJVAHHD-INIZCTEOSA-N 0.000 claims 1
RJFPYIZAIZXRQR-LBPRGKRZSA-N (4S)-7-chloro-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(C2=CC=C(C=C2)C2=C(C)ON=C2C)C2=C(C[C@@H]1C)C=C(Cl)C(OC(F)(F)F)=C2 RJFPYIZAIZXRQR-LBPRGKRZSA-N 0.000 claims 1
SNKUBVXLWUOEPC-NSHDSACASA-N (4S)-8-bromo-1-(4-chlorophenyl)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(Br)ccc2C[C@@H]1C SNKUBVXLWUOEPC-NSHDSACASA-N 0.000 claims 1
VVMJEFWIDBTRQV-NSHDSACASA-N (4S)-8-chloro-1-(4-chlorophenyl)-7-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(Cl)c(OC)cc2C[C@@H]1C VVMJEFWIDBTRQV-NSHDSACASA-N 0.000 claims 1
ZCWQBVYVLQXFPW-JTQLQIEISA-N (4S)-8-chloro-1-(4-chlorophenyl)-N,4-dimethyl-7-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(Cl)c(OC(F)(F)F)cc2C[C@@H]1C ZCWQBVYVLQXFPW-JTQLQIEISA-N 0.000 claims 1
NPYUOJOFPHEJPP-INIZCTEOSA-N (4S)-8-methoxy-N,4-dimethyl-1-(4-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC1=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)N2CCOCC2)C(=O)NC)C)C=C1 NPYUOJOFPHEJPP-INIZCTEOSA-N 0.000 claims 1
VOPJXSOPLUDTMP-HNNXBMFYSA-N (4S)-8-methoxy-N,4-dimethyl-1-[4-(1-methylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC1=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)C=2C=NN(C2)C)C(=O)NC)C)C=C1 VOPJXSOPLUDTMP-HNNXBMFYSA-N 0.000 claims 1
ATCJTSJPZIFWHZ-HNNXBMFYSA-N (4S)-8-methoxy-N,4-dimethyl-1-[4-(3-oxomorpholin-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC1=CC2=C(C[C@@H](N(N=C2C2=CC=C(C=C2)N2C(COCC2)=O)C(=O)NC)C)C=C1 ATCJTSJPZIFWHZ-HNNXBMFYSA-N 0.000 claims 1
PHZKFXUAHTVWFV-AWEZNQCLSA-N (4S)-8-tert-butyl-1-(4-chlorophenyl)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(ccc2C[C@@H]1C)C(C)(C)C PHZKFXUAHTVWFV-AWEZNQCLSA-N 0.000 claims 1
KPBTZKZVLXSZMJ-INIZCTEOSA-N (4S)-N,4-dimethyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(cc2)N2CCN(C)CC2)c2cc(OC(F)(F)F)ccc2C[C@@H]1C KPBTZKZVLXSZMJ-INIZCTEOSA-N 0.000 claims 1
VRRWTCUDSZFECD-OAHLLOKOSA-N (4r)-1-[4-(3-hydroxy-3-methylazetidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1CC(C)(O)C1 VRRWTCUDSZFECD-OAHLLOKOSA-N 0.000 claims 1
IIWHBPLCRMEBBT-LJQANCHMSA-N (4r)-4-ethyl-7,8-dimethoxy-n-methyl-1-(4-piperazin-1-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C([C@H](N(N=1)C(=O)NC)CC)C2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCNCC1 IIWHBPLCRMEBBT-LJQANCHMSA-N 0.000 claims 1
CKERAYAJLNUKGL-HXUWFJFHSA-N (4r)-4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C([C@H](N(N=1)C(=O)NC)CC)C2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCN(S(C)(=O)=O)CC1 CKERAYAJLNUKGL-HXUWFJFHSA-N 0.000 claims 1
GEBVCSMARNXRFJ-OAHLLOKOSA-N (4r)-7,8-dimethoxy-n,4-dimethyl-1-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1C=1C(C)=NN(C)C=1C GEBVCSMARNXRFJ-OAHLLOKOSA-N 0.000 claims 1
UHLLYESSLFHDJE-CQSZACIVSA-N (4r)-n,4-dimethyl-8-(trifluoromethoxy)-1-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@@H](CC1=CC=C(OC(F)(F)F)C=C11)C)N=C1C(C=C1)=CC=C1C=1C(C)=NN(C)C=1C UHLLYESSLFHDJE-CQSZACIVSA-N 0.000 claims 1
KDPVVCOKPRPFTR-ZDUSSCGKSA-N (4s)-1-(4-chlorophenyl)-n,4-dimethyl-7-(2-oxo-1,3-oxazolidin-3-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(=CC=C11)N2C(OCC2)=O)C)N=C1C1=CC=C(Cl)C=C1 KDPVVCOKPRPFTR-ZDUSSCGKSA-N 0.000 claims 1
SMWPGJJESJLTIK-INIZCTEOSA-N (4s)-1-[3-bromo-4-(4-methylpiperazin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1Br)=CC=C1N1CCN(C)CC1 SMWPGJJESJLTIK-INIZCTEOSA-N 0.000 claims 1
RDYPWCXHSFYPQA-KRWDZBQOSA-N (4s)-1-[3-cyano-4-(4-methylpiperazin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1C#N)=CC=C1N1CCN(C)CC1 RDYPWCXHSFYPQA-KRWDZBQOSA-N 0.000 claims 1
QLEGFNBPEXPBRT-AWEZNQCLSA-N (4s)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-8-methoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1C=1C(C)=NOC=1C QLEGFNBPEXPBRT-AWEZNQCLSA-N 0.000 claims 1
YKAHDSJCXVTGOQ-KRWDZBQOSA-N (4s)-1-[4-(3,5-dimethylpyrazol-1-yl)phenyl]-8-methoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1N=C(C)C=C1C YKAHDSJCXVTGOQ-KRWDZBQOSA-N 0.000 claims 1
RJKDXRJDQNJVOJ-KRWDZBQOSA-N (4s)-1-[4-(3-cyclopropyl-5-ethylpyrazol-1-yl)phenyl]-8-methoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C=2C=CC(=CC=2)C=2C3=CC(OC)=CC=C3C[C@H](C)N(N=2)C(=O)NC)C(CC)=CC=1C1CC1 RJKDXRJDQNJVOJ-KRWDZBQOSA-N 0.000 claims 1
HPKUCPBGPDLLSU-IBGZPJMESA-N (4s)-1-[4-(3-cyclopropyl-5-pyridin-2-ylpyrazol-1-yl)phenyl]-8-methoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1N=C(C2CC2)C=C1C1=CC=CC=N1 HPKUCPBGPDLLSU-IBGZPJMESA-N 0.000 claims 1
RHPYMFVZUJVIOQ-KRWDZBQOSA-N (4s)-1-[4-(5-cyclopropyl-3-ethylpyrazol-1-yl)phenyl]-8-methoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C=1C=C(C=2C3=CC(OC)=CC=C3C[C@H](C)N(N=2)C(=O)NC)C=CC=1N1N=C(CC)C=C1C1CC1 RHPYMFVZUJVIOQ-KRWDZBQOSA-N 0.000 claims 1
DPENFFRGVSQXPT-IBGZPJMESA-N (4s)-1-[4-(5-cyclopropyl-3-pyridin-2-ylpyrazol-1-yl)phenyl]-8-methoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1N=C(C=2N=CC=CC=2)C=C1C1CC1 DPENFFRGVSQXPT-IBGZPJMESA-N 0.000 claims 1
YXCQHAAYZHTAHB-KSZLIROESA-N (4s)-1-[4-[(3s,5r)-3,5-dimethylpiperazin-1-yl]phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1C[C@H](C)N[C@H](C)C1 YXCQHAAYZHTAHB-KSZLIROESA-N 0.000 claims 1
IIWHBPLCRMEBBT-IBGZPJMESA-N (4s)-4-ethyl-7,8-dimethoxy-n-methyl-1-(4-piperazin-1-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C([C@@H](N(N=1)C(=O)NC)CC)C2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCNCC1 IIWHBPLCRMEBBT-IBGZPJMESA-N 0.000 claims 1
YKPZZGLYAUXPPY-FQEVSTJZSA-N (4s)-4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C([C@@H](N(N=1)C(=O)NC)CC)C2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCN(C)CC1 YKPZZGLYAUXPPY-FQEVSTJZSA-N 0.000 claims 1
CKERAYAJLNUKGL-FQEVSTJZSA-N (4s)-4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C([C@@H](N(N=1)C(=O)NC)CC)C2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCN(S(C)(=O)=O)CC1 CKERAYAJLNUKGL-FQEVSTJZSA-N 0.000 claims 1
GEBVCSMARNXRFJ-HNNXBMFYSA-N (4s)-7,8-dimethoxy-n,4-dimethyl-1-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1C=1C(C)=NN(C)C=1C GEBVCSMARNXRFJ-HNNXBMFYSA-N 0.000 claims 1
OAWXLCKGNRISLZ-KRWDZBQOSA-N (4s)-7,8-dimethoxy-n,4-dimethyl-1-[4-(4-methyl-2-oxo-1,4-diazepan-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1CCCN(C)CC1=O OAWXLCKGNRISLZ-KRWDZBQOSA-N 0.000 claims 1
JGCATJICLCFSEV-INIZCTEOSA-N (4s)-7,8-dimethoxy-n,4-dimethyl-1-[4-(4-methyl-2-oxopiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1CCN(C)CC1=O JGCATJICLCFSEV-INIZCTEOSA-N 0.000 claims 1
VHMHXYGNKKHLOU-INIZCTEOSA-N (4s)-8-methoxy-1-[4-[3-(methoxymethyl)-5-methylpyrazol-1-yl]phenyl]-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1N=C(COC)C=C1C VHMHXYGNKKHLOU-INIZCTEOSA-N 0.000 claims 1
GPFFZGAEXNBVEK-KRWDZBQOSA-N (4s)-8-methoxy-1-[4-[5-(methoxymethyl)-3-methylpyrazol-1-yl]phenyl]-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1N=C(C)C=C1COC GPFFZGAEXNBVEK-KRWDZBQOSA-N 0.000 claims 1
FGDBNCWEETYHSC-AWEZNQCLSA-N (4s)-8-methoxy-n,4-dimethyl-1-[4-(1,2-oxazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1C=1C=NOC=1 FGDBNCWEETYHSC-AWEZNQCLSA-N 0.000 claims 1
BQGVWBXFWNYZEK-AWEZNQCLSA-N (4s)-8-methoxy-n,4-dimethyl-1-[4-(1h-pyrazol-5-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1C1=CC=NN1 BQGVWBXFWNYZEK-AWEZNQCLSA-N 0.000 claims 1
OQLCMGVUPVNESN-HNNXBMFYSA-N (4s)-8-methoxy-n,4-dimethyl-1-[4-(2-methylpyrazol-3-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1C1=CC=NN1C OQLCMGVUPVNESN-HNNXBMFYSA-N 0.000 claims 1
JKCBHKMSVWKCSQ-ZDUSSCGKSA-N (4s)-8-methoxy-n,4-dimethyl-1-[4-(tetrazol-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1C=NN=N1 JKCBHKMSVWKCSQ-ZDUSSCGKSA-N 0.000 claims 1
UHLLYESSLFHDJE-AWEZNQCLSA-N (4s)-n,4-dimethyl-8-(trifluoromethoxy)-1-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N([C@H](CC1=CC=C(OC(F)(F)F)C=C11)C)N=C1C(C=C1)=CC=C1C=1C(C)=NN(C)C=1C UHLLYESSLFHDJE-AWEZNQCLSA-N 0.000 claims 1
PXVRYVKRCYRXMJ-SFHVURJKSA-N (4s)-n-ethyl-7,8-dimethoxy-4-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCNC(=O)N([C@H](CC1=CC(OC)=C(OC)C=C11)C)N=C1C(C=C1)=CC=C1N1CCN(C)CC1 PXVRYVKRCYRXMJ-SFHVURJKSA-N 0.000 claims 1
XHLSSEYCKJYVNE-UHFFFAOYSA-N 1-(3-bromo-4-fluorophenyl)-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(F)C(Br)=C1 XHLSSEYCKJYVNE-UHFFFAOYSA-N 0.000 claims 1
XZYAZUWVZBESLZ-UHFFFAOYSA-N 1-(3-bromophenyl)-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=CC(Br)=C1 XZYAZUWVZBESLZ-UHFFFAOYSA-N 0.000 claims 1
OUEKEIZYJYAMLY-UHFFFAOYSA-N 1-(4-bromophenyl)-4-ethyl-7,8-dimethoxy-N-methyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCC1Cc2cc(OC)c(OC)cc2C(=NN1C(=O)NC)c1ccc(Br)cc1 OUEKEIZYJYAMLY-UHFFFAOYSA-N 0.000 claims 1
IAJSXDSQAYGWRL-UHFFFAOYSA-N 1-(4-bromophenyl)-7,8-bis(difluoromethoxy)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC(F)F)c(OC(F)F)cc2CC1C IAJSXDSQAYGWRL-UHFFFAOYSA-N 0.000 claims 1
PTYOCYVNWPQFEC-UHFFFAOYSA-N 1-(4-bromophenyl)-7,8-diethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCOc1cc2CC(C)N(N=C(c3ccc(Br)cc3)c2cc1OCC)C(=O)NC PTYOCYVNWPQFEC-UHFFFAOYSA-N 0.000 claims 1
AWGQTKLRWZOYTG-UHFFFAOYSA-N 1-(4-bromophenyl)-7,8-dihydroxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(O)c(O)cc2CC1C AWGQTKLRWZOYTG-UHFFFAOYSA-N 0.000 claims 1
ZFQRJKODMANARY-UHFFFAOYSA-N 1-(4-bromophenyl)-7,8-dimethoxy-N-methyl-4-propan-2-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC)c(OC)cc2CC1C(C)C ZFQRJKODMANARY-UHFFFAOYSA-N 0.000 claims 1
FJUKBDRJUMGMMY-UHFFFAOYSA-N 1-(4-bromophenyl)-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Br)C=C1 FJUKBDRJUMGMMY-UHFFFAOYSA-N 0.000 claims 1
AARDJPUSMQDQHD-UHFFFAOYSA-N 1-(4-bromophenyl)-7-(difluoromethoxy)-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound BrC1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC(F)F)OC)C)C(=O)NC AARDJPUSMQDQHD-UHFFFAOYSA-N 0.000 claims 1
IYMYNCIIPKBZCX-UHFFFAOYSA-N 1-(4-bromophenyl)-7-hydroxy-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC)c(O)cc2CC1C IYMYNCIIPKBZCX-UHFFFAOYSA-N 0.000 claims 1
ZRGNOTAPYUBVTL-UHFFFAOYSA-N 1-(4-bromophenyl)-N-ethyl-7,8-dimethoxy-4-methyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCNC(=O)N1N=C(c2ccc(Br)cc2)c2cc(OC)c(OC)cc2CC1C ZRGNOTAPYUBVTL-UHFFFAOYSA-N 0.000 claims 1
KCANSIWLRYISCV-UHFFFAOYSA-N 1-(4-chlorophenyl)-7-(3,5-dimethyl-1,2-oxazol-4-yl)-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(C3=C(ON=C3C)C)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 KCANSIWLRYISCV-UHFFFAOYSA-N 0.000 claims 1
CIIKBPFATWLYGY-UHFFFAOYSA-N 1-(4-chlorophenyl)-7-(4-fluorophenyl)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2ccc(cc2CC1C)-c1ccc(F)cc1 CIIKBPFATWLYGY-UHFFFAOYSA-N 0.000 claims 1
LFAOJAVKFOSDPL-UHFFFAOYSA-N 1-(4-chlorophenyl)-7-cyano-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(C2=CC=C(Cl)C=C2)C2=C(CC1C)C=C(C#N)C(OC)=C2 LFAOJAVKFOSDPL-UHFFFAOYSA-N 0.000 claims 1
HCGJMHTZBSZOSV-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-(3,5-dimethylpyrazol-1-yl)-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(N3C(=CC(C)=N3)C)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 HCGJMHTZBSZOSV-UHFFFAOYSA-N 0.000 claims 1
LBHJVAHATMRZIP-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-cyclopropyl-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(C3CC3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 LBHJVAHATMRZIP-UHFFFAOYSA-N 0.000 claims 1
CXYGUZTWOCUILI-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-hydroxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(O)ccc2CC1C CXYGUZTWOCUILI-UHFFFAOYSA-N 0.000 claims 1
ZLXBGGKQDNRCPA-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-methoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(OC)ccc2CC1C ZLXBGGKQDNRCPA-UHFFFAOYSA-N 0.000 claims 1
VOWICFDROBFRIK-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-methoxy-N,4-dimethyl-7-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2cc(OC)c(OC(F)(F)F)cc2CC1C VOWICFDROBFRIK-UHFFFAOYSA-N 0.000 claims 1
XAUMIWJFGTVNKQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4,8-trimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)C)C)C(=O)NC XAUMIWJFGTVNKQ-UHFFFAOYSA-N 0.000 claims 1
PVXFQUDILGERQX-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4-dimethyl-7-(6-oxo-1H-pyridin-3-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2ccc(cc2CC1C)-c1ccc(O)nc1 PVXFQUDILGERQX-UHFFFAOYSA-N 0.000 claims 1
HZIXMEDAZJOITP-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4-dimethyl-7-morpholin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2ccc(cc2CC1C)N1CCOCC1 HZIXMEDAZJOITP-UHFFFAOYSA-N 0.000 claims 1
RVVFKMFKBZARON-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4-dimethyl-7-pyridin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(c2ccc(Cl)cc2)c2ccc(cc2CC1C)-c1ccncc1 RVVFKMFKBZARON-UHFFFAOYSA-N 0.000 claims 1
ODFAHDARADIJSK-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4-dimethyl-8-(2-morpholin-4-ylethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)OCCN2CCOCC2)C)C(=O)NC ODFAHDARADIJSK-UHFFFAOYSA-N 0.000 claims 1
ZIORHBAJMSNICU-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4-dimethyl-8-(4-methylpiperazin-1-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)N2CCN(CC2)C)C)C(=O)NC ZIORHBAJMSNICU-UHFFFAOYSA-N 0.000 claims 1
BLHLMVOTWJRLDJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-N,4-dimethyl-8-[2-(4-methylpiperazin-1-yl)ethoxy]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)OCCN2CCN(CC2)C)C)C(=O)NC BLHLMVOTWJRLDJ-UHFFFAOYSA-N 0.000 claims 1
RQJVPAPEFLVQSA-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-7-(1-methyltriazol-4-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(C=3N=NN(C)C=3)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 RQJVPAPEFLVQSA-UHFFFAOYSA-N 0.000 claims 1
KDPVVCOKPRPFTR-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-7-(2-oxo-1,3-oxazolidin-3-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(N3C(OCC3)=O)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 KDPVVCOKPRPFTR-UHFFFAOYSA-N 0.000 claims 1
SLKRSEJGVKFKIT-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-7-(2-oxopiperidin-1-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(N3C(CCCC3)=O)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 SLKRSEJGVKFKIT-UHFFFAOYSA-N 0.000 claims 1
GBKLPTZYTATVTR-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-7-(4-methylpiperazin-1-yl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(N3CCN(C)CC3)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 GBKLPTZYTATVTR-UHFFFAOYSA-N 0.000 claims 1
MGFRZTGEDZXNBM-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-7-pyrrolidin-1-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(N3CCCC3)C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 MGFRZTGEDZXNBM-UHFFFAOYSA-N 0.000 claims 1
AMFRSWDEJJBDJY-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-(2-pyrrolidin-1-ylethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OCCN3CCCC3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 AMFRSWDEJJBDJY-UHFFFAOYSA-N 0.000 claims 1
SKCMLPGXWYMSOE-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-(3-morpholin-4-ylpropoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OCCCN3CCOCC3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 SKCMLPGXWYMSOE-UHFFFAOYSA-N 0.000 claims 1
MVAHTFLZMOQYDC-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC(F)(F)F)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 MVAHTFLZMOQYDC-UHFFFAOYSA-N 0.000 claims 1
BGOGYMGFOKKAOF-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-[3-(4-methylpiperazin-1-yl)propoxy]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OCCCN3CCN(C)CC3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 BGOGYMGFOKKAOF-UHFFFAOYSA-N 0.000 claims 1
IGQGCTMPRICFDO-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-[4-(methylsulfamoyl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(C=3C=CC(=CC=3)S(=O)(=O)NC)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 IGQGCTMPRICFDO-UHFFFAOYSA-N 0.000 claims 1
JAPYRZRQVTWQPV-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-morpholin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(N3CCOCC3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 JAPYRZRQVTWQPV-UHFFFAOYSA-N 0.000 claims 1
KXZZMXOALKEWGH-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-piperidin-1-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(N3CCCCC3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 KXZZMXOALKEWGH-UHFFFAOYSA-N 0.000 claims 1
PZCXKAXTECSTJU-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,4-dimethyl-8-pyridin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(C=3C=CN=CC=3)=CC=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(Cl)C=C1 PZCXKAXTECSTJU-UHFFFAOYSA-N 0.000 claims 1
LAAJMPVAHRCEIU-UHFFFAOYSA-N 1-(4-fluoro-3-morpholin-4-ylphenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=C(C=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)N2CCOCC2 LAAJMPVAHRCEIU-UHFFFAOYSA-N 0.000 claims 1
QFKMKDHGKRANCC-KRWDZBQOSA-N 1-[(4s)-7,8-dimethoxy-4-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepin-3-yl]ethanone Chemical compound CC(=O)N([C@@H](C)CC=1C=C(C(=CC=11)OC)OC)N=C1C(C=C1)=CC=C1N1CCN(C)CC1 QFKMKDHGKRANCC-KRWDZBQOSA-N 0.000 claims 1
XJLJDRPQTUQYPZ-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-7,8-dimethoxy-4-methyl-4,5-dihydro-2,3-benzodiazepin-3-yl]ethanone Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(C)N(C(C)=O)N=C1C1=CC=C(Br)C=C1 XJLJDRPQTUQYPZ-UHFFFAOYSA-N 0.000 claims 1
NWQKGEIEFXZFBU-UHFFFAOYSA-N 1-[1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7,8-dimethoxy-4-methyl-4,5-dihydro-2,3-benzodiazepin-3-yl]ethanone Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(C)N(C(C)=O)N=C1C(C=C1)=CC=C1C=1C(C)=NOC=1C NWQKGEIEFXZFBU-UHFFFAOYSA-N 0.000 claims 1
XJVCYALNQJAAEH-UHFFFAOYSA-N 1-[2,4-dibromo-5-(4-methylpiperazin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C(=CC=1Br)Br)=CC=1N1CCN(C)CC1 XJVCYALNQJAAEH-UHFFFAOYSA-N 0.000 claims 1
CMFGADYGKJVDEP-UHFFFAOYSA-N 1-[3-(3,3-difluoroazetidin-1-yl)-4-fluorophenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(C2=CC(N3CC(F)(F)C3)=C(F)C=C2)C2=C(CC1C)C=C(OC)C(OC)=C2 CMFGADYGKJVDEP-UHFFFAOYSA-N 0.000 claims 1
PFGCHOLEXIESKZ-UHFFFAOYSA-N 1-[3-(3,3-difluoroazetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1(CN(C1)C=1C=C(C=CC1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)F PFGCHOLEXIESKZ-UHFFFAOYSA-N 0.000 claims 1
BTVOSNWRZGPNBZ-UHFFFAOYSA-N 1-[3-(3,5-dimethyl-1,2-oxazol-4-yl)-4-fluorophenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=1)=CC=C(F)C=1C=1C(C)=NOC=1C BTVOSNWRZGPNBZ-UHFFFAOYSA-N 0.000 claims 1
WXFLXTSDECBMFI-UHFFFAOYSA-N 1-[3-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=1)=CC=CC=1C=1C(C)=NOC=1C WXFLXTSDECBMFI-UHFFFAOYSA-N 0.000 claims 1
TYWSXDVELVAJSX-UHFFFAOYSA-N 1-[3-(azetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N1(CCC1)C=1C=C(C=CC1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC TYWSXDVELVAJSX-UHFFFAOYSA-N 0.000 claims 1
UUEAKICRGSCBRU-UHFFFAOYSA-N 1-[4-(2,3-dimethylimidazol-4-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CN1C(=NC=C1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C UUEAKICRGSCBRU-UHFFFAOYSA-N 0.000 claims 1
QQISTRSVAAIHJT-UHFFFAOYSA-N 1-[4-(2,4-dichlorophenyl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=C(Cl)C=C1Cl QQISTRSVAAIHJT-UHFFFAOYSA-N 0.000 claims 1
VKNZQFSNSSJZOA-UHFFFAOYSA-N 1-[4-(2,4-difluorophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC VKNZQFSNSSJZOA-UHFFFAOYSA-N 0.000 claims 1
LVOZKSSVIPZABA-UHFFFAOYSA-N 1-[4-(2,4-dimethyl-1,3-thiazol-5-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C=1SC(C)=NC=1C LVOZKSSVIPZABA-UHFFFAOYSA-N 0.000 claims 1
VYYHRDOCPVUAJA-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC VYYHRDOCPVUAJA-UHFFFAOYSA-N 0.000 claims 1
YSCZPZXFJXKJDA-UHFFFAOYSA-N 1-[4-(2-cyanophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC YSCZPZXFJXKJDA-UHFFFAOYSA-N 0.000 claims 1
JQESLRKKIWVGNZ-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC JQESLRKKIWVGNZ-UHFFFAOYSA-N 0.000 claims 1
CDFDNAHVAIPXPY-UHFFFAOYSA-N 1-[4-(3,3-difluoroazetidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CC(F)(F)C1 CDFDNAHVAIPXPY-UHFFFAOYSA-N 0.000 claims 1
NZKPCKYXSQWGOT-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2,4-triazol-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NN(C(=N1)C)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC NZKPCKYXSQWGOT-UHFFFAOYSA-N 0.000 claims 1
OEJBKZYIXFUYIK-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-4-ethyl-7,8-dimethoxy-n-methyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1C=1C(C)=NOC=1C OEJBKZYIXFUYIK-UHFFFAOYSA-N 0.000 claims 1
VPRZNMOVVIGOCT-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7,8-diethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OCC)OCC)C)C(=O)NC)C VPRZNMOVVIGOCT-UHFFFAOYSA-N 0.000 claims 1
LUFRZKPVUCTMLL-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C=1C(C)=NOC=1C LUFRZKPVUCTMLL-UHFFFAOYSA-N 0.000 claims 1
WNWINTRQQDNGSE-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-8-(3,5-dimethylpyrazol-1-yl)-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)N2N=C(C=C2C)C)C)C(=O)NC)C WNWINTRQQDNGSE-UHFFFAOYSA-N 0.000 claims 1
SAQGMSJAIGSBBP-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-8-hydroxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(O)=CC=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C=1C(C)=NOC=1C SAQGMSJAIGSBBP-UHFFFAOYSA-N 0.000 claims 1
NMZBTHZCHZRLIK-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4,8-trimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)C)C)C(=O)NC)C NMZBTHZCHZRLIK-UHFFFAOYSA-N 0.000 claims 1
BOCVNUPZEQYYEN-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4-dimethyl-8-(3-morpholin-4-ylpropoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)OCCCN2CCOCC2)C)C(=O)NC)C BOCVNUPZEQYYEN-UHFFFAOYSA-N 0.000 claims 1
JVTTUZQEDRLPJQ-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4-dimethyl-8-morpholin-4-yl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C=C2)N2CCOCC2)C)C(=O)NC)C JVTTUZQEDRLPJQ-UHFFFAOYSA-N 0.000 claims 1
OXNNTRMUDOKTFO-UHFFFAOYSA-N 1-[4-(3-carbamoylphenyl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=CC(C(N)=O)=C1 OXNNTRMUDOKTFO-UHFFFAOYSA-N 0.000 claims 1
ZLDPOMFRFWCWSU-UHFFFAOYSA-N 1-[4-(3-cyanophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C(#N)C=1C=C(C=CC1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ZLDPOMFRFWCWSU-UHFFFAOYSA-N 0.000 claims 1
PDUUWSOXKGSSEU-UHFFFAOYSA-N 1-[4-(3-fluoro-5-hydroxyphenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC=1C=C(C=C(C1)O)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC PDUUWSOXKGSSEU-UHFFFAOYSA-N 0.000 claims 1
VYMXLXHXUSCNCY-UHFFFAOYSA-N 1-[4-(3-fluoro-5-methylphenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC=1C=C(C=C(C1)C)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC VYMXLXHXUSCNCY-UHFFFAOYSA-N 0.000 claims 1
ZDRURUMITWYFTN-UHFFFAOYSA-N 1-[4-(3-fluoroazetidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1CN(C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ZDRURUMITWYFTN-UHFFFAOYSA-N 0.000 claims 1
PSVRGWXCEVQFNS-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC=1C=C(C=CC1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC PSVRGWXCEVQFNS-UHFFFAOYSA-N 0.000 claims 1
VRRWTCUDSZFECD-UHFFFAOYSA-N 1-[4-(3-hydroxy-3-methylazetidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CC(C)(O)C1 VRRWTCUDSZFECD-UHFFFAOYSA-N 0.000 claims 1
RRMCJIAMPXSTGK-UHFFFAOYSA-N 1-[4-(3-hydroxyazetidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CC(O)C1 RRMCJIAMPXSTGK-UHFFFAOYSA-N 0.000 claims 1
TVWPNBBGAHUHTK-UHFFFAOYSA-N 1-[4-(4-acetylpiperazin-1-yl)phenyl]-4-ethyl-7,8-dimethoxy-n-methyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCN(C(C)=O)CC1 TVWPNBBGAHUHTK-UHFFFAOYSA-N 0.000 claims 1
AHXWGPPTSZMJOU-UHFFFAOYSA-N 1-[4-(4-acetylpiperazin-1-yl)phenyl]-n,4-dimethyl-7-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(OC(F)(F)F)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCN(C(C)=O)CC1 AHXWGPPTSZMJOU-UHFFFAOYSA-N 0.000 claims 1
FKJLWQOEQJCEPL-UHFFFAOYSA-N 1-[4-(4-benzyl-2-oxopiperazin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N(C(C1)=O)CCN1CC1=CC=CC=C1 FKJLWQOEQJCEPL-UHFFFAOYSA-N 0.000 claims 1
YUFKQXNACOYDFC-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 YUFKQXNACOYDFC-UHFFFAOYSA-N 0.000 claims 1
UYKDRULKSYBEFA-UHFFFAOYSA-N 1-[4-(4-cyanophenyl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC UYKDRULKSYBEFA-UHFFFAOYSA-N 0.000 claims 1
QIPXHQPEGCFBQE-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=C(F)C=C1 QIPXHQPEGCFBQE-UHFFFAOYSA-N 0.000 claims 1
GOUXWYFDGHOSSS-UHFFFAOYSA-N 1-[4-(4-hydroxypiperidin-1-yl)phenyl]-n,4-dimethyl-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC(F)(F)F)=CC=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCC(O)CC1 GOUXWYFDGHOSSS-UHFFFAOYSA-N 0.000 claims 1
NAMYBRJRBNIRIQ-UHFFFAOYSA-N 1-[4-(5-cyclopropyl-3-phenylpyrazol-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C1(CC1)C1=CC(=NN1C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C2=CC=CC=C2 NAMYBRJRBNIRIQ-UHFFFAOYSA-N 0.000 claims 1
SRUSJOIHVSHPAK-UHFFFAOYSA-N 1-[4-(azetidin-1-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCC1 SRUSJOIHVSHPAK-UHFFFAOYSA-N 0.000 claims 1
RQYIKWFRMYYYGA-BLAYRMRBSA-N 1-[4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C[C@@H]1N(C[C@H](NC1)C)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC RQYIKWFRMYYYGA-BLAYRMRBSA-N 0.000 claims 1
KUXDMRAONOYXDM-FUBQLUNQSA-N 1-[4-[(3s)-3-hydroxypyrrolidin-1-yl]phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CC[C@H](O)C1 KUXDMRAONOYXDM-FUBQLUNQSA-N 0.000 claims 1
KRQSIMXBYQOQAE-UHFFFAOYSA-N 1-[4-[2-(hydroxymethyl)phenyl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound OCC1=C(C=CC=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC KRQSIMXBYQOQAE-UHFFFAOYSA-N 0.000 claims 1
IQMMAUCMUHPOBF-UHFFFAOYSA-N 1-[4-[2-(methanesulfonamido)phenyl]phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=CC=C1NS(C)(=O)=O IQMMAUCMUHPOBF-UHFFFAOYSA-N 0.000 claims 1
ONNQNUAUYFRDQK-UHFFFAOYSA-N 1-[4-[3-(4-fluorophenyl)pyrazol-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=CC=C(C=C1)C1=NN(C=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ONNQNUAUYFRDQK-UHFFFAOYSA-N 0.000 claims 1
YCMFVGPKGJSGID-UHFFFAOYSA-N 1-[4-[3-(methanesulfonamido)phenyl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)NS(=O)(=O)C)C(=O)NC)C)C1)OC YCMFVGPKGJSGID-UHFFFAOYSA-N 0.000 claims 1
MWHOKDGHBWPVRL-UHFFFAOYSA-N 1-[4-[3-[2-(dimethylamino)ethylcarbamoyl]phenyl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CN(CCNC(=O)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C MWHOKDGHBWPVRL-UHFFFAOYSA-N 0.000 claims 1
DTHDWYGQNBSDSI-UHFFFAOYSA-N 1-[4-[4-(2,2-difluoroethyl)piperazin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC(CN1CCN(CC1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)F DTHDWYGQNBSDSI-UHFFFAOYSA-N 0.000 claims 1
CMFHHGDMUMYHQA-UHFFFAOYSA-N 1-[4-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound OC(C(=O)N1CCN(CC1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)(C)C CMFHHGDMUMYHQA-UHFFFAOYSA-N 0.000 claims 1
QNDWCQWTOWZCMA-UHFFFAOYSA-N 1-[4-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound OCCN1CCN(CC1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC QNDWCQWTOWZCMA-UHFFFAOYSA-N 0.000 claims 1
HNEABLKAJSSLQV-UHFFFAOYSA-N 1-[4-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl]-n,4-dimethyl-7-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(OC(F)(F)F)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCN(CCO)CC1 HNEABLKAJSSLQV-UHFFFAOYSA-N 0.000 claims 1
UCSQTSGENAPCMO-UHFFFAOYSA-N 1-[4-[4-(2-hydroxyethyl)piperidin-1-yl]phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCC(CCO)CC1 UCSQTSGENAPCMO-UHFFFAOYSA-N 0.000 claims 1
ZNAFVQCXDRQQQT-UHFFFAOYSA-N 1-[4-[4-(5-chlorothiophen-2-yl)phenyl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound ClC1=CC=C(S1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC ZNAFVQCXDRQQQT-UHFFFAOYSA-N 0.000 claims 1
RWDZQEWWDLNUGK-UHFFFAOYSA-N 1-[4-[4-(cyclopropylsulfamoyl)phenyl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C1(CC1)NS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC RWDZQEWWDLNUGK-UHFFFAOYSA-N 0.000 claims 1
RMQQVUOTOWBNTB-UHFFFAOYSA-N 1-[4-[4-(dimethylamino)piperidin-1-yl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CN(C1CCN(CC1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C RMQQVUOTOWBNTB-UHFFFAOYSA-N 0.000 claims 1
MUBXZHJIVWSTGU-UHFFFAOYSA-N 1-[4-[4-(hydroxymethyl)phenyl]phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound OCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC MUBXZHJIVWSTGU-UHFFFAOYSA-N 0.000 claims 1
HXOGVHZMVYEICY-UHFFFAOYSA-N 1-[4-[4-(methanesulfonamido)phenyl]phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=C(NS(C)(=O)=O)C=C1 HXOGVHZMVYEICY-UHFFFAOYSA-N 0.000 claims 1
WKABZPVBAODNFD-UHFFFAOYSA-N 1-[4-fluoro-3-(1,3,5-trimethylpyrazol-4-yl)phenyl]-7,8-dimethoxy-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=1)=CC=C(F)C=1C=1C(C)=NN(C)C=1C WKABZPVBAODNFD-UHFFFAOYSA-N 0.000 claims 1
QEOGOPFYAVNLAR-UHFFFAOYSA-N 1-[4-fluoro-3-(1-methylpyrazol-4-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=C(C=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)C=2C=NN(C2)C QEOGOPFYAVNLAR-UHFFFAOYSA-N 0.000 claims 1
MPEOKEBELRYMFM-UHFFFAOYSA-N 1-[4-fluoro-3-(4-hydroxypiperidin-1-yl)phenyl]-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC1=C(C=C(C=C1)C1=NN(C(CC2=C1C=C(C(=C2)OC)OC)C)C(=O)NC)N2CCC(CC2)O MPEOKEBELRYMFM-UHFFFAOYSA-N 0.000 claims 1
QFKMKDHGKRANCC-UHFFFAOYSA-N 1-[7,8-dimethoxy-4-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepin-3-yl]ethanone Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(C)N(C(C)=O)N=C1C(C=C1)=CC=C1N1CCN(C)CC1 QFKMKDHGKRANCC-UHFFFAOYSA-N 0.000 claims 1
WANXIXPGWJEENE-UHFFFAOYSA-N 1-[7,8-dimethoxy-4-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepin-3-yl]propan-1-one Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)CC)N=C1C(C=C1)=CC=C1N1CCN(C)CC1 WANXIXPGWJEENE-UHFFFAOYSA-N 0.000 claims 1
MTVQVHJOJPZPCS-UHFFFAOYSA-N 1-[8-tert-butyl-1-(4-chlorophenyl)-4-methyl-4,5-dihydro-2,3-benzodiazepin-3-yl]ethanone Chemical compound N=1N(C(C)=O)C(C)CC2=CC=C(C(C)(C)C)C=C2C=1C1=CC=C(Cl)C=C1 MTVQVHJOJPZPCS-UHFFFAOYSA-N 0.000 claims 1
HRMYCTVQXTYORS-UHFFFAOYSA-N 2-cyclopropyl-7,8-dimethoxy-4-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-1,3,4,5-tetrahydro-2,3-benzodiazepine Chemical class C=1C=C(N2CCN(C)CC2)C=CC=1C1C=2C=C(OC)C(OC)=CC=2CC(C)NN1C1CC1 HRMYCTVQXTYORS-UHFFFAOYSA-N 0.000 claims 1
VYQMBYMEBUTSHF-UHFFFAOYSA-N 4-ethyl-1-[4-(3-fluoroazetidin-1-yl)phenyl]-7,8-dimethoxy-n-methyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CC(F)C1 VYQMBYMEBUTSHF-UHFFFAOYSA-N 0.000 claims 1
RAUHTCWAYWYVPV-UHFFFAOYSA-N 4-ethyl-1-[4-(4-fluorophenyl)phenyl]-7,8-dimethoxy-N-methyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCC1Cc2cc(OC)c(OC)cc2C(=NN1C(=O)NC)c1ccc(cc1)-c1ccc(F)cc1 RAUHTCWAYWYVPV-UHFFFAOYSA-N 0.000 claims 1
GTCPNBUMUTYGMM-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-N-methyl-1-(4-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCC1Cc2cc(OC)c(OC)cc2C(=NN1C(=O)NC)c1ccc(cc1)N1CCOCC1 GTCPNBUMUTYGMM-UHFFFAOYSA-N 0.000 claims 1
ZWJHMLKCIKPILS-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-N-methyl-1-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCC1Cc2cc(OC)c(OC)cc2C(=NN1C(=O)NC)c1ccc(cc1)N1CCOC1=O ZWJHMLKCIKPILS-UHFFFAOYSA-N 0.000 claims 1
LXBAEIFOMPMODU-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-N-methyl-1-[4-(3-oxomorpholin-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CCC1Cc2cc(OC)c(OC)cc2C(=NN1C(=O)NC)c1ccc(cc1)N1CCOCC1=O LXBAEIFOMPMODU-UHFFFAOYSA-N 0.000 claims 1
IIWHBPLCRMEBBT-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-(4-piperazin-1-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCNCC1 IIWHBPLCRMEBBT-UHFFFAOYSA-N 0.000 claims 1
YLZJSPVVMNZDOV-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1C=1C(C)=NN(C)C=1C YLZJSPVVMNZDOV-UHFFFAOYSA-N 0.000 claims 1
CMCOLQVPMOCHMC-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(1-methyltriazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1C1=CN(C)N=N1 CMCOLQVPMOCHMC-UHFFFAOYSA-N 0.000 claims 1
YOUXOKPGDSYEAR-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCCCC1=O YOUXOKPGDSYEAR-UHFFFAOYSA-N 0.000 claims 1
YGULGXDVVBBOBE-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(2-oxopyrrolidin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCCC1=O YGULGXDVVBBOBE-UHFFFAOYSA-N 0.000 claims 1
YKPZZGLYAUXPPY-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCN(C)CC1 YKPZZGLYAUXPPY-UHFFFAOYSA-N 0.000 claims 1
CKERAYAJLNUKGL-UHFFFAOYSA-N 4-ethyl-7,8-dimethoxy-n-methyl-1-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound N=1N(C(=O)NC)C(CC)CC2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1N1CCN(S(C)(=O)=O)CC1 CKERAYAJLNUKGL-UHFFFAOYSA-N 0.000 claims 1
NLJFTASPDRFPGO-UHFFFAOYSA-N 5-[4-[7,8-dimethoxy-4-methyl-3-(methylcarbamoyl)-4,5-dihydro-2,3-benzodiazepin-1-yl]phenyl]thiophene-2-carboxylic acid Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=C(C(O)=O)S1 NLJFTASPDRFPGO-UHFFFAOYSA-N 0.000 claims 1
DQRSQHVJZVTTGY-UHFFFAOYSA-N 7,8-bis(difluoromethoxy)-1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound FC(OC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C=2C(=NOC2C)C)C(=O)NC)C)C1)OC(F)F)F DQRSQHVJZVTTGY-UHFFFAOYSA-N 0.000 claims 1
RTTOAKRWKWSXDG-UHFFFAOYSA-N 7,8-dimethoxy-1-[4-(2-methoxyphenyl)phenyl]-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(C2=CC=C(C=C2)C2=C(OC)C=CC=C2)C2=CC(OC)=C(OC)C=C2CC1C RTTOAKRWKWSXDG-UHFFFAOYSA-N 0.000 claims 1
AKFLJWDACFCAHG-UHFFFAOYSA-N 7,8-dimethoxy-1-[4-(3-methoxyphenyl)phenyl]-N,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)OC)C(=O)NC)C)C1)OC AKFLJWDACFCAHG-UHFFFAOYSA-N 0.000 claims 1
MDVXYZUNKGAFLX-UHFFFAOYSA-N 7,8-dimethoxy-1-[4-(4-methoxyphenyl)phenyl]-n,4-dimethyl-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=C(OC)C=C1 MDVXYZUNKGAFLX-UHFFFAOYSA-N 0.000 claims 1
CUNYPDKIWBRHFR-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-(3-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC(=CC=C2)N2CCOCC2)C(=O)NC)C)C1)OC CUNYPDKIWBRHFR-UHFFFAOYSA-N 0.000 claims 1
UTHKZGZVFZXNSZ-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-(4-piperazin-1-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2CCNCC2)C(=O)NC)C)C1)OC UTHKZGZVFZXNSZ-UHFFFAOYSA-N 0.000 claims 1
CZBLTFKOMSMBDH-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-(4-piperidin-1-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2CCCCC2)C(=O)NC)C)C1)OC CZBLTFKOMSMBDH-UHFFFAOYSA-N 0.000 claims 1
PUNVBJKNAQZIIS-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-(4-pyridin-3-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C=2C=NC=CC2)C(=O)NC)C)C1)OC PUNVBJKNAQZIIS-UHFFFAOYSA-N 0.000 claims 1
YNJOFBJUYAXDIQ-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-(4-pyrimidin-5-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C=2C=NC=NC2)C(=O)NC)C)C1)OC YNJOFBJUYAXDIQ-UHFFFAOYSA-N 0.000 claims 1
OFARABCNCAKDNE-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[3-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC(=CC=C2)C=2C(=NN(C2C)C)C)C(=O)NC)C)C1)OC OFARABCNCAKDNE-UHFFFAOYSA-N 0.000 claims 1
AWNHQZBGOKCVIN-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[3-(1-methylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC(=CC=C2)C=2C=NN(C2)C)C(=O)NC)C)C1)OC AWNHQZBGOKCVIN-UHFFFAOYSA-N 0.000 claims 1
FZTJHCRQMIHJMR-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(1,2,4-triazol-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2N=CN=C2)C(=O)NC)C)C1)OC FZTJHCRQMIHJMR-UHFFFAOYSA-N 0.000 claims 1
DBGYIBIBCLSANP-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(1-methylpyrrol-2-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C=2N(C=CC2)C)C(=O)NC)C)C1)OC DBGYIBIBCLSANP-UHFFFAOYSA-N 0.000 claims 1
KARWDXYDKONLAM-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(1H-pyrazol-5-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=NNC=C2)C(=O)NC)C)C1)OC KARWDXYDKONLAM-UHFFFAOYSA-N 0.000 claims 1
AKRHFEUVWLCJNF-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(2-methylpyrazol-3-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC=NN2C)C(=O)NC)C)C1)OC AKRHFEUVWLCJNF-UHFFFAOYSA-N 0.000 claims 1
UOSONIPZIOSFTK-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(3-sulfamoylphenyl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)S(N)(=O)=O)C(=O)NC)C)C1)OC UOSONIPZIOSFTK-UHFFFAOYSA-N 0.000 claims 1
LKQMDKYKSIZJRH-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(4-methylsulfonylphenyl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC=C(C=C2)S(=O)(=O)C)C(=O)NC)C)C1)OC LKQMDKYKSIZJRH-UHFFFAOYSA-N 0.000 claims 1
DRPWZYTYSMCSMR-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2CCN(CC2)S(=O)(=O)C)C(=O)NC)C)C1)OC DRPWZYTYSMCSMR-UHFFFAOYSA-N 0.000 claims 1
HBBHQPYLOJQNTK-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(4-morpholin-4-ylphenyl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC=C(C=C2)N2CCOCC2)C(=O)NC)C)C1)OC HBBHQPYLOJQNTK-UHFFFAOYSA-N 0.000 claims 1
SYYRKQDUFKQQCL-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(4-nitrophenyl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC=C(C=C2)[N+](=O)[O-])C(=O)NC)C)C1)OC SYYRKQDUFKQQCL-UHFFFAOYSA-N 0.000 claims 1
CVOLNTXNUQTBQN-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2N=CN=C2C)C(=O)NC)C)C1)OC CVOLNTXNUQTBQN-UHFFFAOYSA-N 0.000 claims 1
MVBCISMWUBFARK-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-(5-methyl-3-phenylpyrazol-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2N=C(C=C2C)C2=CC=CC=C2)C(=O)NC)C)C1)OC MVBCISMWUBFARK-UHFFFAOYSA-N 0.000 claims 1
ZWOWVFXXJOFLAK-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[3-(methylsulfamoyl)phenyl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)S(NC)(=O)=O)C(=O)NC)C)C1)OC ZWOWVFXXJOFLAK-UHFFFAOYSA-N 0.000 claims 1
JHLJQHVINBKOAO-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[3-(morpholine-4-carbonyl)phenyl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)C(=O)N2CCOCC2)C(=O)NC)C)C1)OC JHLJQHVINBKOAO-UHFFFAOYSA-N 0.000 claims 1
FGHRRLVGCJUXGA-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[3-(piperidine-1-carbonyl)phenyl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)C(=O)N2CCCCC2)C(=O)NC)C)C1)OC FGHRRLVGCJUXGA-UHFFFAOYSA-N 0.000 claims 1
QLIPOLJHAJSDRF-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[3-(pyrrolidine-1-carbonyl)phenyl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC(=CC=C2)C(=O)N2CCCC2)C(=O)NC)C)C1)OC QLIPOLJHAJSDRF-UHFFFAOYSA-N 0.000 claims 1
YKFQZHDQSXUBCZ-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[3-phenyl-5-(trifluoromethyl)pyrazol-1-yl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2N=C(C=C2C(F)(F)F)C2=CC=CC=C2)C(=O)NC)C)C1)OC YKFQZHDQSXUBCZ-UHFFFAOYSA-N 0.000 claims 1
QSYMSVYVSRAFEC-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[4-(2,2,2-trifluoroacetyl)piperazin-1-yl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound CNC(=O)N1N=C(C2=CC=C(C=C2)N2CCN(CC2)C(=O)C(F)(F)F)C2=C(CC1C)C=C(OC)C(OC)=C2 QSYMSVYVSRAFEC-UHFFFAOYSA-N 0.000 claims 1
DVMUBQCFFUPAAL-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2CCN(CC2)CC(F)(F)F)C(=O)NC)C)C1)OC DVMUBQCFFUPAAL-UHFFFAOYSA-N 0.000 claims 1
XCQZHUPSJINTRJ-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[4-(methylsulfamoyl)phenyl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C2=CC=C(C=C2)S(NC)(=O)=O)C(=O)NC)C)C1)OC XCQZHUPSJINTRJ-UHFFFAOYSA-N 0.000 claims 1
REOGNNADXNVRAO-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)N2N=C(C=C2C)C(F)(F)F)C(=O)NC)C)C1)OC REOGNNADXNVRAO-UHFFFAOYSA-N 0.000 claims 1
SKUACLMMLHPQSX-UHFFFAOYSA-N 7,8-dimethoxy-N,4-dimethyl-1-[4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound COC=1C(=CC2=C(CC(N(N=C2C2=CC=C(C=C2)C=2C=NC(=CC2)C(F)(F)F)C(=O)NC)C)C1)OC SKUACLMMLHPQSX-UHFFFAOYSA-N 0.000 claims 1
LBLJTEJVPNXQKZ-UHFFFAOYSA-N 7,8-dimethoxy-N-methyl-4-propan-2-yl-1-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C(C)(C)C1N(N=C(C2=C(C1)C=C(C(=C2)OC)OC)C2=CC=C(C=C2)C=2C(=NN(C2C)C)C)C(=O)NC LBLJTEJVPNXQKZ-UHFFFAOYSA-N 0.000 claims 1
NPQSRNGURRYZDG-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-(4-morpholin-4-ylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCOCC1 NPQSRNGURRYZDG-UHFFFAOYSA-N 0.000 claims 1
QYTKGAXXMIBUKI-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-(4-phenylphenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 QYTKGAXXMIBUKI-UHFFFAOYSA-N 0.000 claims 1
VLZSNRWGRCUFKQ-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-[3-(2-methylpyrazol-3-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=1)=CC=CC=1C1=CC=NN1C VLZSNRWGRCUFKQ-UHFFFAOYSA-N 0.000 claims 1
FLKWTRHXBNBSGP-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-[4-(1,2-oxazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C=1C=NOC=1 FLKWTRHXBNBSGP-UHFFFAOYSA-N 0.000 claims 1
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AUSGEPFKFFOZTQ-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-[4-(1-methyltriazol-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1C1=CN(C)N=N1 AUSGEPFKFFOZTQ-UHFFFAOYSA-N 0.000 claims 1
ITXIDOOMPDCULR-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-[4-(2-methyl-3-oxomorpholin-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCOC(C)C1=O ITXIDOOMPDCULR-UHFFFAOYSA-N 0.000 claims 1
AQZDMZDWIQNIAN-UHFFFAOYSA-N 7,8-dimethoxy-n,4-dimethyl-1-[4-(2-methyl-5-oxomorpholin-4-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CC(C)OCC1=O AQZDMZDWIQNIAN-UHFFFAOYSA-N 0.000 claims 1
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KPBTZKZVLXSZMJ-UHFFFAOYSA-N n,4-dimethyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-8-(trifluoromethoxy)-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC(F)(F)F)=CC=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCN(C)CC1 KPBTZKZVLXSZMJ-UHFFFAOYSA-N 0.000 claims 1
BHALJROXZFYJFY-UHFFFAOYSA-N n,4-dimethyl-7-(4-methyl-3-oxopiperazin-1-yl)-1-[4-(4-methyl-3-oxopiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC=C(N3CC(=O)N(C)CC3)C=C2CC(C)N(C(=O)NC)N=C1C(C=C1)=CC=C1N1CCN(C)C(=O)C1 BHALJROXZFYJFY-UHFFFAOYSA-N 0.000 claims 1
PXVRYVKRCYRXMJ-UHFFFAOYSA-N n-ethyl-7,8-dimethoxy-4-methyl-1-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-2,3-benzodiazepine-3-carboxamide Chemical compound C12=CC(OC)=C(OC)C=C2CC(C)N(C(=O)NCC)N=C1C(C=C1)=CC=C1N1CCN(C)CC1 PXVRYVKRCYRXMJ-UHFFFAOYSA-N 0.000 claims 1
230000001613 neoplastic effect Effects 0.000 claims 1
230000004770 neurodegeneration Effects 0.000 claims 1
208000015122 neurodegenerative disease Diseases 0.000 claims 1
230000035479 physiological effects, processes and functions Effects 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
208000019553 vascular disease Diseases 0.000 claims 1
230000009385 viral infection Effects 0.000 claims 1
239000002904 solvent Substances 0.000 description 5
125000004183 alkoxy alkyl group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2

JP2015526970A 2012-08-16 2013-08-13 ２，３−ベンゾジアゼピン類 Expired - Fee Related JP6333251B2 (ja)