JP2017530185A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017530185A5 JP2017530185A5 JP2017518989A JP2017518989A JP2017530185A5 JP 2017530185 A5 JP2017530185 A5 JP 2017530185A5 JP 2017518989 A JP2017518989 A JP 2017518989A JP 2017518989 A JP2017518989 A JP 2017518989A JP 2017530185 A5 JP2017530185 A5 JP 2017530185A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dichlorophenyl
- dihydroisoquinolin
- ethanone
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 alkyl amides Chemical class 0.000 claims description 169
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 13
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 5
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 5
- 230000001548 androgenic effect Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- JRSXZJXUCSYNGP-UHFFFAOYSA-N 1-methyl-n-(2-methylphenyl)-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1CC2=CC=CC=C2C(C)N1C(=O)NC1=CC=CC=C1C JRSXZJXUCSYNGP-UHFFFAOYSA-N 0.000 claims description 3
- OFKDYCMYTGQBIX-UHFFFAOYSA-N N-(2,3-dichlorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C=CC=C1Cl)NC(=O)N1C(C2=CC=CC=C2CC1)C OFKDYCMYTGQBIX-UHFFFAOYSA-N 0.000 claims description 3
- MQGBDRZWPMGKLY-UHFFFAOYSA-N N-(2,4-dichlorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C=CC(=C1)Cl)NC(=O)N1C(C2=CC=CC=C2CC1)C MQGBDRZWPMGKLY-UHFFFAOYSA-N 0.000 claims description 3
- NNAGIUAAGNEDIR-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound CC1=C(C(=CC=C1)C)NC(=O)N1C(C2=CC=CC=C2CC1)C NNAGIUAAGNEDIR-UHFFFAOYSA-N 0.000 claims description 3
- NNCYHQAVFRGUBF-UHFFFAOYSA-N N-(2-bromophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound BrC1=C(C=CC=C1)NC(=O)N1C(C2=CC=CC=C2CC1)C NNCYHQAVFRGUBF-UHFFFAOYSA-N 0.000 claims description 3
- BERXXVMLFCHFAQ-UHFFFAOYSA-N N-(2-fluorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound FC1=C(C=CC=C1)NC(=O)N1C(C2=CC=CC=C2CC1)C BERXXVMLFCHFAQ-UHFFFAOYSA-N 0.000 claims description 3
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- VLCPQJCYZTXACO-CYBMUJFWSA-N 2-(2-fluorophenyl)-1-[(1r)-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound N1([C@@H](C2=CC=CC=C2CC1)C)C(=O)CC1=CC=CC=C1F VLCPQJCYZTXACO-CYBMUJFWSA-N 0.000 claims description 2
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 2
- 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 11
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 2
- XZMCEPFQBRRENA-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1-(4,4-difluoro-1-methyl-1,3-dihydroisoquinolin-2-yl)ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1C(C2=CC=CC=C2C(C1)(F)F)C XZMCEPFQBRRENA-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010024264 Lethargy Diseases 0.000 claims 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims 2
- 201000002832 Lewy body dementia Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 230000007000 age related cognitive decline Effects 0.000 claims 2
- 230000000561 anti-psychotic effect Effects 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000001149 cognitive effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- VJGXOACAPIGNKO-LLVKDONJSA-N (1R)-N-(2,6-dichlorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1[C@@H](C2=CC=CC=C2CC1)C VJGXOACAPIGNKO-LLVKDONJSA-N 0.000 claims 1
- OGJAIHIWVZHTBR-NSHDSACASA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-1,3-dihydroisoquinolin-4-one Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2C(C1)=O)C OGJAIHIWVZHTBR-NSHDSACASA-N 0.000 claims 1
- QGYITPQJFPCDLU-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinoline-5-carbonitrile Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C#N)C QGYITPQJFPCDLU-LBPRGKRZSA-N 0.000 claims 1
- YBILZOWIRBPGHP-NSHDSACASA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)N)C YBILZOWIRBPGHP-NSHDSACASA-N 0.000 claims 1
- LFJQMFBGPGANMS-NSHDSACASA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)(=O)N)C LFJQMFBGPGANMS-NSHDSACASA-N 0.000 claims 1
- ALWVFJCCPZFJJH-KRWDZBQOSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N,N-di(propan-2-yl)-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)N(C(C)C)C(C)C)C ALWVFJCCPZFJJH-KRWDZBQOSA-N 0.000 claims 1
- PMXIQDLWZGKMRF-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-(1H-1,2,4-triazol-5-yl)-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)NC1=NN=CN1)C PMXIQDLWZGKMRF-LBPRGKRZSA-N 0.000 claims 1
- WRGTTXFYNFHYGU-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-(1H-1,2,4-triazol-5-yl)-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)(=O)NC1=NN=CN1)C WRGTTXFYNFHYGU-LBPRGKRZSA-N 0.000 claims 1
- XJXXMWCYUJMTOU-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)NCC(F)(F)F)C XJXXMWCYUJMTOU-LBPRGKRZSA-N 0.000 claims 1
- UJXVKMDZSPTBHW-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)(=O)NCC(F)(F)F)C UJXVKMDZSPTBHW-LBPRGKRZSA-N 0.000 claims 1
- GNEBWGGAWPGZMM-AWEZNQCLSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-propan-2-yl-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)NC(C)C)C GNEBWGGAWPGZMM-AWEZNQCLSA-N 0.000 claims 1
- JGKLARRANXRQIR-AWEZNQCLSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-propan-2-yl-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)(=O)NC(C)C)C JGKLARRANXRQIR-AWEZNQCLSA-N 0.000 claims 1
- REIKCVUSKMBFKX-HNNXBMFYSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-N-pyridin-2-yl-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)NC1=NC=CC=C1)C REIKCVUSKMBFKX-HNNXBMFYSA-N 0.000 claims 1
- HMWWXWYWVDLTSE-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-N,1-dimethyl-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)NC)C HMWWXWYWVDLTSE-LBPRGKRZSA-N 0.000 claims 1
- KAPXIZGAXGHGPX-LBPRGKRZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-N,1-dimethyl-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)(=O)NC)C KAPXIZGAXGHGPX-LBPRGKRZSA-N 0.000 claims 1
- SRLTXOBTZZNBCQ-ZDUSSCGKSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-N,N,1-trimethyl-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)N(C)C)C SRLTXOBTZZNBCQ-ZDUSSCGKSA-N 0.000 claims 1
- ATUSKDMTCNISHY-NGXIVSIZSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-N,N,1-trimethyl-3,4-dihydro-1H-isoquinoline-5-sulfinamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)N(C)C)C ATUSKDMTCNISHY-NGXIVSIZSA-N 0.000 claims 1
- BRVQQHPKPWSRQU-ZDUSSCGKSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-N-ethyl-1-methyl-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)C(=O)NCC)C BRVQQHPKPWSRQU-ZDUSSCGKSA-N 0.000 claims 1
- BHEZRSYREDPXOA-ZDUSSCGKSA-N (1S)-2-[2-(2,6-dichlorophenyl)acetyl]-N-ethyl-1-methyl-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C=2C=CC=C(C=2CC1)S(=O)(=O)NCC)C BHEZRSYREDPXOA-ZDUSSCGKSA-N 0.000 claims 1
- VJGXOACAPIGNKO-NSHDSACASA-N (1S)-N-(2,6-dichlorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1[C@H](C2=CC=CC=C2CC1)C VJGXOACAPIGNKO-NSHDSACASA-N 0.000 claims 1
- CMWLWNUPWSLAMB-NSHDSACASA-N (1S)-N-(2,6-dichlorophenyl)-1-methyl-5-methylsulfonyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)C)C CMWLWNUPWSLAMB-NSHDSACASA-N 0.000 claims 1
- OTYALRNHSCZPDG-NSHDSACASA-N (1S)-N-(2,6-dichlorophenyl)-5-(hydroxymethyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1[C@H](C2=CC=CC(=C2CC1)CO)C OTYALRNHSCZPDG-NSHDSACASA-N 0.000 claims 1
- JGSWXBCVCWXNII-NSHDSACASA-N (1S)-N-(2,6-dichlorophenyl)-5-(methanesulfonamido)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1[C@H](C2=CC=CC(=C2CC1)NS(=O)(=O)C)C JGSWXBCVCWXNII-NSHDSACASA-N 0.000 claims 1
- NNAGIUAAGNEDIR-HNNXBMFYSA-N (1S)-N-(2,6-dimethylphenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound CC1=C(C(=CC=C1)C)NC(=O)N1[C@H](C2=CC=CC=C2CC1)C NNAGIUAAGNEDIR-HNNXBMFYSA-N 0.000 claims 1
- QOAUXJGHYDWTRN-LBPRGKRZSA-N (1S)-N-(2-bromo-6-methoxyphenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound BrC1=C(C(=CC=C1)OC)NC(=O)N1[C@H](C2=CC=CC=C2CC1)C QOAUXJGHYDWTRN-LBPRGKRZSA-N 0.000 claims 1
- NNCYHQAVFRGUBF-LBPRGKRZSA-N (1S)-N-(2-bromophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound BrC1=C(C=CC=C1)NC(=O)N1[C@H](C2=CC=CC=C2CC1)C NNCYHQAVFRGUBF-LBPRGKRZSA-N 0.000 claims 1
- YWSALMYNNFUEEZ-ZDUSSCGKSA-N (1S)-N-(2-chloro-6-methylphenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)N1[C@H](C2=CC=CC=C2CC1)C YWSALMYNNFUEEZ-ZDUSSCGKSA-N 0.000 claims 1
- OXEUWLUBSNWQEA-NSHDSACASA-N (1S)-N-(5-bromo-2-chlorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound C[C@@H]1N(CCC2=C1C=CC=C2)C(=O)NC1=C(Cl)C=CC(Br)=C1 OXEUWLUBSNWQEA-NSHDSACASA-N 0.000 claims 1
- WBUIHUIBJWJQBY-ZDUSSCGKSA-N (1S)-N-(cyanomethyl)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinoline-5-sulfonamide Chemical compound C(#N)CNS(=O)(=O)C=1C=2CCN([C@H](C=2C=CC=1)C)C(CC1=C(C=CC=C1Cl)Cl)=O WBUIHUIBJWJQBY-ZDUSSCGKSA-N 0.000 claims 1
- XMZUHDZJOKXWTP-BONVTDFDSA-N (1S,4R)-N-(2,6-dichlorophenyl)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound C[C@@H]1N(C[C@H](O)C2=C1C=CC=C2)C(=O)NC1=C(Cl)C=CC=C1Cl XMZUHDZJOKXWTP-BONVTDFDSA-N 0.000 claims 1
- XMZUHDZJOKXWTP-ZUZCIYMTSA-N (1S,4S)-N-(2,6-dichlorophenyl)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1[C@H](C2=CC=CC=C2[C@@H](C1)O)C XMZUHDZJOKXWTP-ZUZCIYMTSA-N 0.000 claims 1
- ODCVVYDDMMVPKU-LBPRGKRZSA-N 1-[(1S)-5-(2-amino-1,1-difluoroethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2,6-dichlorophenyl)ethanone Chemical compound NCC(F)(F)C1=C2CCN([C@H](C2=CC=C1)C)C(CC1=C(C=CC=C1Cl)Cl)=O ODCVVYDDMMVPKU-LBPRGKRZSA-N 0.000 claims 1
- UBWUVVWDCGFYPD-AWEZNQCLSA-N 1-[(1S)-5-(6-aminopyridin-3-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2,6-dichlorophenyl)ethanone Chemical compound NC1=CC=C(C=N1)C1=C2CCN([C@H](C2=CC=C1)C)C(CC1=C(C=CC=C1Cl)Cl)=O UBWUVVWDCGFYPD-AWEZNQCLSA-N 0.000 claims 1
- YLMYMDDZTDMHJH-NSHDSACASA-N 1-[(1S)-5-amino-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2,6-dichlorophenyl)ethanone Chemical compound NC1=C2CCN([C@H](C2=CC=C1)C)C(CC1=C(C=CC=C1Cl)Cl)=O YLMYMDDZTDMHJH-NSHDSACASA-N 0.000 claims 1
- TXWXJJUQVRTLIH-ZDUSSCGKSA-N 1-[[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methyl]-3-methylurea Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CNC(=O)NC)C TXWXJJUQVRTLIH-ZDUSSCGKSA-N 0.000 claims 1
- QOSVHEYJMYRRHR-LBPRGKRZSA-N 2,4-dichloro-3-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC1=C(C#N)C=CC(=C1CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)Cl QOSVHEYJMYRRHR-LBPRGKRZSA-N 0.000 claims 1
- ASLJDBYXXGCHTK-LBPRGKRZSA-N 2-(2,6-dichloro-3-methylsulfanylphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1SC)Cl)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C ASLJDBYXXGCHTK-LBPRGKRZSA-N 0.000 claims 1
- SCNQMAWDBYZJGR-UNHBDAOFSA-N 2-(2,6-dichloro-3-methylsulfinylphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1S(=O)C)Cl)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C SCNQMAWDBYZJGR-UNHBDAOFSA-N 0.000 claims 1
- RDKYJKZEYXPWSS-DYZYQPBXSA-N 2-(2,6-dichloro-4-fluorophenyl)-1-[(1S,4S)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC(=C1)F)Cl)CC(=O)N1[C@H](C2=CC=CC=C2[C@@H](C1)O)C RDKYJKZEYXPWSS-DYZYQPBXSA-N 0.000 claims 1
- LEQWSDJJUWAZLL-UNHBDAOFSA-N 2-(2,6-dichloro-4-methylsulfinylphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC(=C1)S(=O)C)Cl)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C LEQWSDJJUWAZLL-UNHBDAOFSA-N 0.000 claims 1
- GAWZRMSXMKMAIC-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1-(1,4,4-trimethyl-1,3-dihydroisoquinolin-2-yl)ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1C(C2=CC=CC=C2C(C1)(C)C)C GAWZRMSXMKMAIC-UHFFFAOYSA-N 0.000 claims 1
- SUTPENAAFLOLOK-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1-(1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1C(C2=CC=CC=C2CC1)C SUTPENAAFLOLOK-UHFFFAOYSA-N 0.000 claims 1
- SUTPENAAFLOLOK-GFCCVEGCSA-N 2-(2,6-dichlorophenyl)-1-[(1R)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@@H](C2=CC=CC=C2CC1)C SUTPENAAFLOLOK-GFCCVEGCSA-N 0.000 claims 1
- SUTPENAAFLOLOK-LBPRGKRZSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C SUTPENAAFLOLOK-LBPRGKRZSA-N 0.000 claims 1
- CFNCYPFRVSGCJL-RSXQAXDFSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-4-methylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2C(C1)S(=O)(=O)C)C CFNCYPFRVSGCJL-RSXQAXDFSA-N 0.000 claims 1
- AFUYOGBIZRNGDR-AWEZNQCLSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(1-methylsulfonyl-4,5-dihydroimidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1N(CCN=1)S(=O)(=O)C)C AFUYOGBIZRNGDR-AWEZNQCLSA-N 0.000 claims 1
- YVQHJIFZMQPQOS-LYKKTTPLSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(2-methylpyrrolidine-1-carbonyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(=O)N1C(CCC1)C)C YVQHJIFZMQPQOS-LYKKTTPLSA-N 0.000 claims 1
- FEOHHTHXZNSXGV-ZDUSSCGKSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(methylsulfanylmethyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CSC)C FEOHHTHXZNSXGV-ZDUSSCGKSA-N 0.000 claims 1
- CPMBPUWIZFWXNZ-ZDUSSCGKSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(methylsulfonylmethyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CS(=O)(=O)C)C CPMBPUWIZFWXNZ-ZDUSSCGKSA-N 0.000 claims 1
- VKSUHOAKXKOXDP-HNNXBMFYSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(morpholine-4-carbonyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(=O)N1CCOCC1)C VKSUHOAKXKOXDP-HNNXBMFYSA-N 0.000 claims 1
- XYSIMJUAGAQTAN-INIZCTEOSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(pyridin-3-ylmethylsulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)CC=1C=NC=CC=1)C XYSIMJUAGAQTAN-INIZCTEOSA-N 0.000 claims 1
- KAVCXHLEYQACFH-HNNXBMFYSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(=O)N1CCCC1)C KAVCXHLEYQACFH-HNNXBMFYSA-N 0.000 claims 1
- SCYLEYZRTZGLGE-WLRWDXFRSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-[(1S)-2,2,2-trifluoro-1-hydroxyethyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)[C@@H](C(F)(F)F)O)C SCYLEYZRTZGLGE-WLRWDXFRSA-N 0.000 claims 1
- DGSDYFKMUVULTA-HNNXBMFYSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-[(5-methyl-1,2-oxazol-3-yl)methylsulfonyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)CC1=NOC(=C1)C)C DGSDYFKMUVULTA-HNNXBMFYSA-N 0.000 claims 1
- MWYJFWWXQVDBOI-VDBVYFBLSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-[(S)-methylsulfinyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)[S@@](=O)C)C MWYJFWWXQVDBOI-VDBVYFBLSA-N 0.000 claims 1
- SVWOSUUMPFKLAJ-HNNXBMFYSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-[4-(trifluoromethyl)piperidine-1-carbonyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(=O)N1CCC(CC1)C(F)(F)F)C SVWOSUUMPFKLAJ-HNNXBMFYSA-N 0.000 claims 1
- MWYJFWWXQVDBOI-UNHBDAOFSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-methylsulfinyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound C[C@@H]1N(CCC2=C1C=CC=C2S(C)=O)C(=O)CC1=C(Cl)C=CC=C1Cl MWYJFWWXQVDBOI-UNHBDAOFSA-N 0.000 claims 1
- VBNNLDHIWIOGMO-LBPRGKRZSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-methylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)C)C VBNNLDHIWIOGMO-LBPRGKRZSA-N 0.000 claims 1
- JGDIVOCPXSSABP-AWEZNQCLSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-propan-2-ylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)C(C)C)C JGDIVOCPXSSABP-AWEZNQCLSA-N 0.000 claims 1
- AYCNHQPMNMXORF-HNNXBMFYSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-1-methyl-5-pyrrolidin-1-ylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)N1CCCC1)C AYCNHQPMNMXORF-HNNXBMFYSA-N 0.000 claims 1
- WNSOYBPPJVGOFN-LBPRGKRZSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(1,1-difluoro-2-hydroxyethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(CO)(F)F)C WNSOYBPPJVGOFN-LBPRGKRZSA-N 0.000 claims 1
- FZDGCNULRKUOLW-INIZCTEOSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(1,1-difluoro-2-morpholin-4-ylethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(CN1CCOCC1)(F)F)C FZDGCNULRKUOLW-INIZCTEOSA-N 0.000 claims 1
- NOXFPDLKIOZYRD-UEWDXFNNSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(1-hydroxyethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(C)O)C NOXFPDLKIOZYRD-UEWDXFNNSA-N 0.000 claims 1
- UTVSMDMIJAHLDK-AWEZNQCLSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(3-hydroxypropyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CCCO)C UTVSMDMIJAHLDK-AWEZNQCLSA-N 0.000 claims 1
- FOTUCWKUQVKSQZ-NGXIVSIZSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(N,S-dimethylsulfonimidoyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=NC)C)C FOTUCWKUQVKSQZ-NGXIVSIZSA-N 0.000 claims 1
- DYWZGNMAVPSQII-DCXKMBIZSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(N-ethyl-S-methylsulfonimidoyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=NCC)C)C DYWZGNMAVPSQII-DCXKMBIZSA-N 0.000 claims 1
- DPLHZOFCAIMEMK-LBPRGKRZSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(hydroxymethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CO)C DPLHZOFCAIMEMK-LBPRGKRZSA-N 0.000 claims 1
- RHNUMGCBWWLSAK-ZDUSSCGKSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-(methoxymethylsulfonyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)COC)C RHNUMGCBWWLSAK-ZDUSSCGKSA-N 0.000 claims 1
- SZPWNAAVXPXAHQ-GJZGRUSLSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-[(3S)-3-hydroxypyrrolidine-1-carbonyl]-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(=O)N1C[C@H](CC1)O)C SZPWNAAVXPXAHQ-GJZGRUSLSA-N 0.000 claims 1
- KJTOLQGGDJPVCE-ZDUSSCGKSA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-ethylsulfonyl-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)CC)C KJTOLQGGDJPVCE-ZDUSSCGKSA-N 0.000 claims 1
- MVYAHFYNYPHPEM-NSHDSACASA-N 2-(2,6-dichlorophenyl)-1-[(1S)-5-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)O)C MVYAHFYNYPHPEM-NSHDSACASA-N 0.000 claims 1
- QSPAZLKGXQHBEQ-GTNSWQLSSA-N 2-(2,6-dichlorophenyl)-1-[(1S,4R)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2[C@H](C1)O)C QSPAZLKGXQHBEQ-GTNSWQLSSA-N 0.000 claims 1
- QSPAZLKGXQHBEQ-APPDUMDISA-N 2-(2,6-dichlorophenyl)-1-[(1S,4S)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2[C@@H](C1)O)C QSPAZLKGXQHBEQ-APPDUMDISA-N 0.000 claims 1
- QUYRYOXULZRZSQ-KPZWWZAWSA-N 2-(2,6-dichlorophenyl)-1-[(1S,4S)-4-methoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2[C@@H](C1)OC)C QUYRYOXULZRZSQ-KPZWWZAWSA-N 0.000 claims 1
- HVRLTTNNEXNMRN-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1C(C2=CC=CC(=C2CC1)C=1C(=NOC=1C)C)C HVRLTTNNEXNMRN-UHFFFAOYSA-N 0.000 claims 1
- INRYRGOCXKASRB-ZDUSSCGKSA-N 2-(2-bromo-6-methoxyphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound BrC1=C(C(=CC=C1)OC)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C INRYRGOCXKASRB-ZDUSSCGKSA-N 0.000 claims 1
- UNVMEDILGAIEPM-IFGYVTRGSA-N 2-(2-chloro-6-fluorophenyl)-1-[(1S)-1-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)F)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(C(F)(F)F)O)C UNVMEDILGAIEPM-IFGYVTRGSA-N 0.000 claims 1
- LZMAIRDYFYWONZ-ZDUSSCGKSA-N 2-(2-chloro-6-methoxyphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)OC)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C LZMAIRDYFYWONZ-ZDUSSCGKSA-N 0.000 claims 1
- HZRJBMRCAHZXOW-ZDUSSCGKSA-N 2-(2-chloro-6-methylsulfanylphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)SC)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C HZRJBMRCAHZXOW-ZDUSSCGKSA-N 0.000 claims 1
- PWPVXQSWLIJMPU-LNHXHEARSA-N 2-(2-chloro-6-methylsulfinylphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound C[C@@H]1N(CCC2=C1C=CC=C2)C(=O)CC1=C(Cl)C=CC=C1S(C)=O PWPVXQSWLIJMPU-LNHXHEARSA-N 0.000 claims 1
- KAYRYAJECIEJHR-ZDUSSCGKSA-N 2-(2-chloro-6-methylsulfonylphenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound C[C@@H]1N(CCC2=C1C=CC=C2)C(=O)CC1=C(Cl)C=CC=C1S(C)(=O)=O KAYRYAJECIEJHR-ZDUSSCGKSA-N 0.000 claims 1
- ZGWQBQQCISAIDW-NSHDSACASA-N 2-(3,5-dichloro-2-methoxypyridin-4-yl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C(=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)Cl)OC ZGWQBQQCISAIDW-NSHDSACASA-N 0.000 claims 1
- ZIDZNAHLMAQBRM-NSHDSACASA-N 2-(3,5-dichloropyridin-4-yl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)Cl ZIDZNAHLMAQBRM-NSHDSACASA-N 0.000 claims 1
- WTAUFGSBTGSXFK-YPMLDQLKSA-N 2-(3,5-dichloropyridin-4-yl)-1-[(1S)-1-methyl-5-[(1S)-2,2,2-trifluoro-1-hydroxyethyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC(=C2CC1)[C@@H](C(F)(F)F)O)C)Cl WTAUFGSBTGSXFK-YPMLDQLKSA-N 0.000 claims 1
- JNBWVGWWYDYITI-NSHDSACASA-N 2-(3,5-dichloropyridin-4-yl)-1-[(1S)-1-methyl-5-methylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)C)C)Cl JNBWVGWWYDYITI-NSHDSACASA-N 0.000 claims 1
- AYOOQYTVFQAVDM-NSHDSACASA-N 2-(3,5-dichloropyridin-4-yl)-1-[(1S)-5-(hydroxymethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CO)C)Cl AYOOQYTVFQAVDM-NSHDSACASA-N 0.000 claims 1
- UFEWTFQRSUQGSI-QFYYESIMSA-N 2-(3,5-dichloropyridin-4-yl)-1-[(1S,4R)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC=C2[C@H](C1)O)C)Cl UFEWTFQRSUQGSI-QFYYESIMSA-N 0.000 claims 1
- QBQVRHDUTRBWDJ-NSHDSACASA-N 2-(3-bromo-2,6-dichlorophenyl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound BrC=1C(=C(C(=CC=1)Cl)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)Cl QBQVRHDUTRBWDJ-NSHDSACASA-N 0.000 claims 1
- NLWJAVIIJGNCTA-ZDUSSCGKSA-N 2-(3-chloro-5-methylpyridin-4-yl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C=NC=C(C=1CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)C NLWJAVIIJGNCTA-ZDUSSCGKSA-N 0.000 claims 1
- ORKVGCYXPPIWMJ-ZOWNYOTGSA-N 2-(5-chloro-1-methylsulfonylpyrrolo[2,3-b]pyridin-4-yl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C[C@@H]1N(CCc2ccccc12)C(=O)Cc1c(Cl)cnc2n(ccc12)S(C)(=O)=O ORKVGCYXPPIWMJ-ZOWNYOTGSA-N 0.000 claims 1
- UOIJYYJIKGKMLE-QKVFXAPYSA-N 2-(5-chloro-1H-indol-4-yl)-1-[(1S)-1-methyl-5-[(1S)-2,2,2-trifluoro-1-hydroxyethyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C(=C2C=CNC2=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)[C@@H](C(F)(F)F)O)C UOIJYYJIKGKMLE-QKVFXAPYSA-N 0.000 claims 1
- RIIZCSYXYIHVNK-LBPRGKRZSA-N 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC=1C(=C2C(=NC=1)NC=C2)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C RIIZCSYXYIHVNK-LBPRGKRZSA-N 0.000 claims 1
- GDYSUYMONIMNBB-NSHDSACASA-N 2-[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]-2,2-difluoroacetamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(C(=O)N)(F)F)C GDYSUYMONIMNBB-NSHDSACASA-N 0.000 claims 1
- GCXKWDABQWNELY-LBPRGKRZSA-N 2-[2,6-dichloro-3-(hydroxymethyl)phenyl]-1-[(1S)-1-methyl-5-methylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1CO)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)C)C GCXKWDABQWNELY-LBPRGKRZSA-N 0.000 claims 1
- PVIKUJDBAVWCCH-UHFFFAOYSA-N 2-[2,6-dichloro-4-(hydroxymethyl)phenyl]-1-(1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone Chemical compound ClC1=C(C(=CC(=C1)CO)Cl)CC(=O)N1C(C2=CC=CC=C2CC1)C PVIKUJDBAVWCCH-UHFFFAOYSA-N 0.000 claims 1
- SVPHHUOSSDYMME-RSAXXLAASA-N 2-[2-[(1S)-5-(2-aminopyridin-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]-3-chlorobenzonitrile 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C[C@@H]1N(CCc2c1cccc2-c1ccnc(N)c1)C(=O)Cc1c(Cl)cccc1C#N SVPHHUOSSDYMME-RSAXXLAASA-N 0.000 claims 1
- ZYGVZSNQYAYAAU-RSAXXLAASA-N 2-[2-[(1S)-5-(6-aminopyridin-3-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]-3-chlorobenzonitrile 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C[C@@H]1N(CCc2c1cccc2-c1ccc(N)nc1)C(=O)Cc1c(Cl)cccc1C#N ZYGVZSNQYAYAAU-RSAXXLAASA-N 0.000 claims 1
- KLPNLXOCKXDAKZ-UQKRIMTDSA-N 2-[2-chloro-6-(1H-pyrazol-4-yl)phenyl]-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C[C@@H]1N(CCc2ccccc12)C(=O)Cc1c(Cl)cccc1-c1cn[nH]c1 KLPNLXOCKXDAKZ-UQKRIMTDSA-N 0.000 claims 1
- DNEXEDCVTLMTOH-ZDUSSCGKSA-N 2-[2-chloro-6-(hydroxymethyl)phenyl]-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)CO)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C DNEXEDCVTLMTOH-ZDUSSCGKSA-N 0.000 claims 1
- VEICFIKQSUFLLL-AWEZNQCLSA-N 2-[2-chloro-6-(methylsulfonylmethyl)phenyl]-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)CS(=O)(=O)C)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C VEICFIKQSUFLLL-AWEZNQCLSA-N 0.000 claims 1
- BMAJZCGKOCATRJ-LBPRGKRZSA-N 2-[2-chloro-6-(trifluoromethyl)phenyl]-1-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound ClC1=C(C(=CC=C1)C(F)(F)F)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C BMAJZCGKOCATRJ-LBPRGKRZSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- UQMJQPDEDGRSRW-JTQLQIEISA-N 3,5-dichloro-4-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]-1H-pyridin-2-one Chemical compound ClC=1C(NC=C(C=1CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)Cl)=O UQMJQPDEDGRSRW-JTQLQIEISA-N 0.000 claims 1
- IHWJRMOYVWXYJG-ZDUSSCGKSA-N 3-chloro-2-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C IHWJRMOYVWXYJG-ZDUSSCGKSA-N 0.000 claims 1
- LKUBULRTNSPQHF-HNNXBMFYSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-(1-methylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C=NN(C=1)C)C LKUBULRTNSPQHF-HNNXBMFYSA-N 0.000 claims 1
- PPAVDNOISOGVED-AWEZNQCLSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-(1H-pyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C=NNC=1)C PPAVDNOISOGVED-AWEZNQCLSA-N 0.000 claims 1
- DBJKODBKVNXIDA-FKIZINRSSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-[(1R)-2,2,2-trifluoro-1-hydroxyethyl]-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)[C@H](C(F)(F)F)O)C DBJKODBKVNXIDA-FKIZINRSSA-N 0.000 claims 1
- DBJKODBKVNXIDA-YUNKPMOVSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-[(1S)-2,2,2-trifluoro-1-hydroxyethyl]-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound C[C@@H]1N(CCC2=C1C=CC=C2[C@H](O)C(F)(F)F)C(=O)CC1=C(C=CC=C1Cl)C#N DBJKODBKVNXIDA-YUNKPMOVSA-N 0.000 claims 1
- HCSANWUAUOUNMC-ZDUSSCGKSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-[5-(trifluoromethyl)-1H-pyrazol-4-yl]-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C(=NNC=1)C(F)(F)F)C HCSANWUAUOUNMC-ZDUSSCGKSA-N 0.000 claims 1
- WTEDLVUUFKFFHK-ZDUSSCGKSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-methylsulfonyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)S(=O)(=O)C)C WTEDLVUUFKFFHK-ZDUSSCGKSA-N 0.000 claims 1
- OUZHRNRLBJNLDA-INIZCTEOSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-pyridin-2-yl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C1=NC=CC=C1)C OUZHRNRLBJNLDA-INIZCTEOSA-N 0.000 claims 1
- PJUCPHICQBSRFK-INIZCTEOSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-pyridin-3-yl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C=NC=CC=1)C PJUCPHICQBSRFK-INIZCTEOSA-N 0.000 claims 1
- XTVJWXOAESOVGM-INIZCTEOSA-N 3-chloro-2-[2-[(1S)-1-methyl-5-pyridin-4-yl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C1=CC=NC=C1)C XTVJWXOAESOVGM-INIZCTEOSA-N 0.000 claims 1
- JRMASVMQKUTZAX-HNNXBMFYSA-N 3-chloro-2-[2-[(1S)-5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C(=NOC=1C)C)C JRMASVMQKUTZAX-HNNXBMFYSA-N 0.000 claims 1
- NDVSSADFNGSALM-INIZCTEOSA-N 3-chloro-2-[2-[(1S)-5-(3,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C(=NNC=1C)C)C NDVSSADFNGSALM-INIZCTEOSA-N 0.000 claims 1
- QYJDNVVOIRSNCU-SGTLLEGYSA-N 3-chloro-2-[2-[(1S,4R)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC=C2[C@H](C1)O)C QYJDNVVOIRSNCU-SGTLLEGYSA-N 0.000 claims 1
- QYJDNVVOIRSNCU-KPZWWZAWSA-N 3-chloro-2-[2-[(1S,4S)-4-hydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound ClC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC=C2[C@@H](C1)O)C QYJDNVVOIRSNCU-KPZWWZAWSA-N 0.000 claims 1
- IVLFCHTXVGNPJW-AWEZNQCLSA-N 3-methoxy-2-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]benzonitrile Chemical compound COC=1C(=C(C#N)C=CC=1)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C IVLFCHTXVGNPJW-AWEZNQCLSA-N 0.000 claims 1
- SCCQNOIYGRUXTH-AWEZNQCLSA-N 4-[(1S)-2-[2-(2-chloro-6-cyanophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]-1H-pyrazole-5-carbonitrile Chemical compound ClC1=C(C(=CC=C1)C#N)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C=1C(=NNC=1)C#N)C SCCQNOIYGRUXTH-AWEZNQCLSA-N 0.000 claims 1
- PVDDJNAOTDZFOR-LBPRGKRZSA-N 5-chloro-4-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]pyridine-3-carbonitrile Chemical compound ClC=1C(=C(C=NC=1)C#N)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C PVDDJNAOTDZFOR-LBPRGKRZSA-N 0.000 claims 1
- ZNDJCSCCKDYWSU-SZQRVLIRSA-N 6-[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]morpholin-3-one Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C1OCC(NC1)=O)C ZNDJCSCCKDYWSU-SZQRVLIRSA-N 0.000 claims 1
- GZGWGDPOVWXTGK-STQMWFEESA-N C[C@H]1C2=CC=CC=C2[C@@H](CN1C(=O)CC3=C(C=CC=C3Cl)Cl)COC(=O)O Chemical compound C[C@H]1C2=CC=CC=C2[C@@H](CN1C(=O)CC3=C(C=CC=C3Cl)Cl)COC(=O)O GZGWGDPOVWXTGK-STQMWFEESA-N 0.000 claims 1
- XLOFQUZCAQKBBX-STQMWFEESA-N C[C@H]1C2=CC=CC=C2[C@H](CN1C(=O)CC3=C(C=CC=C3Cl)Cl)CNC(=O)O Chemical compound C[C@H]1C2=CC=CC=C2[C@H](CN1C(=O)CC3=C(C=CC=C3Cl)Cl)CNC(=O)O XLOFQUZCAQKBBX-STQMWFEESA-N 0.000 claims 1
- GZGWGDPOVWXTGK-QWHCGFSZSA-N C[C@H]1C2=CC=CC=C2[C@H](CN1C(=O)CC3=C(C=CC=C3Cl)Cl)COC(=O)O Chemical compound C[C@H]1C2=CC=CC=C2[C@H](CN1C(=O)CC3=C(C=CC=C3Cl)Cl)COC(=O)O GZGWGDPOVWXTGK-QWHCGFSZSA-N 0.000 claims 1
- VJGXOACAPIGNKO-UHFFFAOYSA-N N-(2,6-dichlorophenyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)N1C(C2=CC=CC=C2CC1)C VJGXOACAPIGNKO-UHFFFAOYSA-N 0.000 claims 1
- IPNHPNIATOHDNN-GFCCVEGCSA-N N-[(1R)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@@H](C2=CC=CC(=C2CC1)NS(=O)(=O)C)C IPNHPNIATOHDNN-GFCCVEGCSA-N 0.000 claims 1
- IPNHPNIATOHDNN-LBPRGKRZSA-N N-[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)NS(=O)(=O)C)C IPNHPNIATOHDNN-LBPRGKRZSA-N 0.000 claims 1
- IEFSMNYTIJENAD-ZDUSSCGKSA-N N-[(1S)-2-[2-(2-chloro-6-cyanophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)C#N)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)NS(=O)(=O)C)C IEFSMNYTIJENAD-ZDUSSCGKSA-N 0.000 claims 1
- ZGIVRTJLYCOXEN-AWEZNQCLSA-N N-[(1S)-2-[2-(2-chloro-6-methylphenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)C)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)NS(=O)(=O)C)C ZGIVRTJLYCOXEN-AWEZNQCLSA-N 0.000 claims 1
- KLOIHOZALSMYAE-LBPRGKRZSA-N N-[2,4-dichloro-3-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]phenyl]methanesulfonamide Chemical compound ClC1=C(C=CC(=C1CC(=O)N1[C@H](C2=CC=CC=C2CC1)C)Cl)NS(=O)(=O)C KLOIHOZALSMYAE-LBPRGKRZSA-N 0.000 claims 1
- JGHZNARWTIMBRF-ZDUSSCGKSA-N N-[2-[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]-2,2-difluoroethyl]acetamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)C(CNC(C)=O)(F)F)C JGHZNARWTIMBRF-ZDUSSCGKSA-N 0.000 claims 1
- XCMCCVHUFKZTSL-AWEZNQCLSA-N N-[2-[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]ethyl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CCNS(=O)(=O)C)C XCMCCVHUFKZTSL-AWEZNQCLSA-N 0.000 claims 1
- QOJIEXOWJGSHOR-UHFFFAOYSA-N N-[2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-7-yl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1C(C2=CC(=CC=C2CC1)NS(=O)(=O)C)C QOJIEXOWJGSHOR-UHFFFAOYSA-N 0.000 claims 1
- SEZMJKDPBUXSKD-ZDUSSCGKSA-N N-[3-chloro-2-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]phenyl]acetamide Chemical compound ClC=1C(=C(C=CC=1)NC(C)=O)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C SEZMJKDPBUXSKD-ZDUSSCGKSA-N 0.000 claims 1
- DJDVRMKDRBYGFH-ZDUSSCGKSA-N N-[3-chloro-2-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]phenyl]methanesulfonamide Chemical compound ClC=1C(=C(C=CC=1)NS(=O)(=O)C)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C DJDVRMKDRBYGFH-ZDUSSCGKSA-N 0.000 claims 1
- KXOWBRJAIKQBMP-ZDUSSCGKSA-N N-[[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methyl]acetamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CNC(C)=O)C KXOWBRJAIKQBMP-ZDUSSCGKSA-N 0.000 claims 1
- MYTWVYBKMJPILA-ZDUSSCGKSA-N N-[[(1S)-2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methyl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1[C@H](C2=CC=CC(=C2CC1)CNS(=O)(=O)C)C MYTWVYBKMJPILA-ZDUSSCGKSA-N 0.000 claims 1
- MYTWVYBKMJPILA-UHFFFAOYSA-N N-[[2-[2-(2,6-dichlorophenyl)acetyl]-1-methyl-3,4-dihydro-1H-isoquinolin-5-yl]methyl]methanesulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CC(=O)N1C(C2=CC=CC(=C2CC1)CNS(=O)(=O)C)C MYTWVYBKMJPILA-UHFFFAOYSA-N 0.000 claims 1
- IQFZDZTWJZTELA-AWEZNQCLSA-N N-[[3-chloro-2-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]phenyl]methyl]acetamide Chemical compound ClC=1C(=C(CNC(C)=O)C=CC=1)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C IQFZDZTWJZTELA-AWEZNQCLSA-N 0.000 claims 1
- DNIGFIYWEYFMPH-AWEZNQCLSA-N N-[[3-chloro-2-[2-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxoethyl]phenyl]methyl]methanesulfonamide Chemical compound ClC=1C(=C(CNS(=O)(=O)C)C=CC=1)CC(=O)N1[C@H](C2=CC=CC=C2CC1)C DNIGFIYWEYFMPH-AWEZNQCLSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14188174 | 2014-10-08 | ||
| EP14188174.8 | 2014-10-08 | ||
| PCT/EP2015/073053 WO2016055479A1 (en) | 2014-10-08 | 2015-10-06 | Tetrahydroisoquinoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017530185A JP2017530185A (ja) | 2017-10-12 |
| JP2017530185A5 true JP2017530185A5 (enExample) | 2019-10-03 |
| JP6622299B2 JP6622299B2 (ja) | 2019-12-18 |
Family
ID=51790569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017518989A Active JP6622299B2 (ja) | 2014-10-08 | 2015-10-06 | テトラヒドロイソキノリン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US10105359B2 (enExample) |
| EP (1) | EP3204359B1 (enExample) |
| JP (1) | JP6622299B2 (enExample) |
| CN (1) | CN107001278B (enExample) |
| BR (1) | BR112017007123B1 (enExample) |
| CA (1) | CA2963951C (enExample) |
| CY (1) | CY1123417T1 (enExample) |
| DK (1) | DK3204359T3 (enExample) |
| EA (1) | EA035544B1 (enExample) |
| ES (1) | ES2821821T3 (enExample) |
| HR (1) | HRP20201469T1 (enExample) |
| HU (1) | HUE050664T2 (enExample) |
| LT (1) | LT3204359T (enExample) |
| PL (1) | PL3204359T3 (enExample) |
| PT (1) | PT3204359T (enExample) |
| RS (1) | RS60933B1 (enExample) |
| SI (1) | SI3204359T1 (enExample) |
| WO (1) | WO2016055479A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017144633A1 (en) * | 2016-02-25 | 2017-08-31 | Asceneuron S. A. | Glycosidase inhibitors |
| ES2819841T3 (es) | 2016-04-13 | 2021-04-19 | UCB Biopharma SRL | Derivados de tetrahidroisoquinolina |
| CN107698433A (zh) * | 2017-09-12 | 2018-02-16 | 潍坊滨海石油化工有限公司 | 苯乙酸的制备方法 |
| WO2019105913A1 (en) | 2017-12-01 | 2019-06-06 | Ucb Biopharma Sprl | Imaging agents |
| TWI725408B (zh) * | 2018-04-20 | 2021-04-21 | 美商美國禮來大藥廠 | 多巴胺d1受體正向異位調節劑 |
| SG11202112537YA (en) | 2019-07-01 | 2021-12-30 | UCB Biopharma SRL | A substituted tetrahydroisoquinoline derivative as a d1 positive allosteric modulator |
| KR20220029687A (ko) * | 2019-07-01 | 2022-03-08 | 유씨비 바이오파마 에스알엘 | D1 양성 알로스테릭 조절제로서의 치환된 테트라히드로이소퀴놀린 유도체 |
| JP2023522980A (ja) * | 2020-04-24 | 2023-06-01 | ザ・リージエンツ・オブ・ザ・ユニバーシテイー・オブ・カリフオルニア | Ｎｕｒｒ１受容体調節因子及びその使用 |
| CN111943930B (zh) * | 2020-08-25 | 2022-11-01 | 南京三元阳普医药科技有限公司 | Lasmiditan的合成工艺 |
| RS65365B1 (sr) * | 2020-10-07 | 2024-04-30 | Lilly Co Eli | Derivati fenil-3,4-dihidroizohinolin-2(1h)-il-etan-1-ona kao pozitivni alosterni modulatori dopamin d1 receptora |
| CN116507332A (zh) * | 2020-12-03 | 2023-07-28 | Ucb生物制药有限责任公司 | 八氢异喹啉基衍生物 |
| ES2999070T3 (en) * | 2020-12-18 | 2025-02-24 | UCB Biopharma SRL | A substituted tetrahydroisoquinoline derivative as a d1 positive allosteric modulator |
| US20240083925A1 (en) * | 2020-12-18 | 2024-03-14 | UCB Biopharma SRL | Prodrugs of 2-(3,5-Dichloro-1-methyl-indazol-4-yl)-1-[(1S,3R)-3-(hydroxymethyl)-5-(1-hydroxy-1-methyl-ethyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone |
| CA3201298A1 (en) * | 2020-12-18 | 2022-06-23 | UCB Biopharma SRL | Amorphous solid dispersions |
| US20240083875A1 (en) | 2020-12-18 | 2024-03-14 | UCB Biopharma SRL | Dihydroisoquinolinyl derivatives |
| KR20230154967A (ko) | 2021-03-08 | 2023-11-09 | 일라이 릴리 앤드 캄파니 | 환각 및 치매 관련 정신병의 치료에서 메비달렌 및 다른 d1 양성 알로스테릭 조절제의 용도 |
| WO2022192255A1 (en) | 2021-03-09 | 2022-09-15 | Eli Lilly And Company | Use of mevidalen and other d1 positive allosteric modulators for slowing of parkinson's disease progression |
| CN114671810B (zh) * | 2022-03-21 | 2024-03-22 | 济南鸿湾生物技术有限公司 | 一种咪唑苯脲的制备方法 |
| CN115611768B (zh) * | 2022-11-14 | 2024-03-05 | 郑州大学 | 一种3,4-二氯苯腈的合成方法 |
| CN118724764B (zh) * | 2024-06-07 | 2025-11-18 | 绍兴文理学院 | 一种芳基伯磺酰胺类化合物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766131A (en) * | 1980-10-17 | 1988-08-23 | Pennwalt Corporation | 2-amino (or hydroxy) phenethyl-1,2,3,4-tetrahydroisoquinolines as analgesics |
| EA006082B1 (ru) * | 2001-12-19 | 2005-08-25 | Х. Лундбекк А/С | Производные 3,4-дигидро-1h-изохинолин-2-ила |
| PT1749001E (pt) * | 2004-04-29 | 2010-05-31 | Aventis Pharma Inc | 3-piperidinilisocroman-5-oles como agonistas da dopamina |
| MX2009009415A (es) * | 2007-03-01 | 2009-09-11 | Janssen Pharmaceutica Nv | Compuestos de tetrahidroisoquinolina como moduladores del receptor h3 de la histamina. |
-
2015
- 2015-10-06 HU HUE15775688A patent/HUE050664T2/hu unknown
- 2015-10-06 SI SI201531348T patent/SI3204359T1/sl unknown
- 2015-10-06 CA CA2963951A patent/CA2963951C/en active Active
- 2015-10-06 WO PCT/EP2015/073053 patent/WO2016055479A1/en not_active Ceased
- 2015-10-06 RS RS20201139A patent/RS60933B1/sr unknown
- 2015-10-06 JP JP2017518989A patent/JP6622299B2/ja active Active
- 2015-10-06 US US15/517,795 patent/US10105359B2/en active Active
- 2015-10-06 EA EA201790785A patent/EA035544B1/ru not_active IP Right Cessation
- 2015-10-06 LT LTEP15775688.3T patent/LT3204359T/lt unknown
- 2015-10-06 DK DK15775688.3T patent/DK3204359T3/da active
- 2015-10-06 PL PL15775688.3T patent/PL3204359T3/pl unknown
- 2015-10-06 PT PT157756883T patent/PT3204359T/pt unknown
- 2015-10-06 CN CN201580064005.3A patent/CN107001278B/zh not_active Expired - Fee Related
- 2015-10-06 EP EP15775688.3A patent/EP3204359B1/en active Active
- 2015-10-06 BR BR112017007123-1A patent/BR112017007123B1/pt not_active IP Right Cessation
- 2015-10-06 ES ES15775688T patent/ES2821821T3/es active Active
- 2015-10-06 HR HRP20201469TT patent/HRP20201469T1/hr unknown
-
2020
- 2020-09-30 CY CY20201100923T patent/CY1123417T1/el unknown