JP2020529419A5 - - Google Patents
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- Publication number
- JP2020529419A5 JP2020529419A5 JP2020505414A JP2020505414A JP2020529419A5 JP 2020529419 A5 JP2020529419 A5 JP 2020529419A5 JP 2020505414 A JP2020505414 A JP 2020505414A JP 2020505414 A JP2020505414 A JP 2020505414A JP 2020529419 A5 JP2020529419 A5 JP 2020529419A5
- Authority
- JP
- Japan
- Prior art keywords
- methaneamine
- isochroman
- hydrochloride
- methyl
- pyridin
- 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
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- OAJYDRUKDNYVAT-INIZCTEOSA-N CNC[C@@H]1OCCCC2=C1C=CC=C2C1=NC=CN=C1 Chemical compound CNC[C@@H]1OCCCC2=C1C=CC=C2C1=NC=CN=C1 OAJYDRUKDNYVAT-INIZCTEOSA-N 0.000 claims description 2
- JSEIDBRHHIBQHP-HNNXBMFYSA-N N1=C(C=NC=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN Chemical compound N1=C(C=NC=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN JSEIDBRHHIBQHP-HNNXBMFYSA-N 0.000 claims description 2
- ISVMISBAMCIJMA-UHFFFAOYSA-N N1=CC=C(C=C1)C1=C2CCOC(C2=CC=C1)CNCC Chemical compound N1=CC=C(C=C1)C1=C2CCOC(C2=CC=C1)CNCC ISVMISBAMCIJMA-UHFFFAOYSA-N 0.000 claims description 2
- ZMMLHOJJKMZKIQ-HNNXBMFYSA-N N1=CN=C(C=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN Chemical compound N1=CN=C(C=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN ZMMLHOJJKMZKIQ-HNNXBMFYSA-N 0.000 claims description 2
- ZMMLHOJJKMZKIQ-OAHLLOKOSA-N N1=CN=C(C=C1)C1=CC=CC=2[C@H](OCCCC=21)CN Chemical compound N1=CN=C(C=C1)C1=CC=CC=2[C@H](OCCCC=21)CN ZMMLHOJJKMZKIQ-OAHLLOKOSA-N 0.000 claims description 2
- GXOUFCPOHOJJQE-AWEZNQCLSA-N O1N=CC(=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN Chemical compound O1N=CC(=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN GXOUFCPOHOJJQE-AWEZNQCLSA-N 0.000 claims description 2
- GXOUFCPOHOJJQE-CQSZACIVSA-N O1N=CC(=C1)C1=CC=CC=2[C@H](OCCCC=21)CN Chemical compound O1N=CC(=C1)C1=CC=CC=2[C@H](OCCCC=21)CN GXOUFCPOHOJJQE-CQSZACIVSA-N 0.000 claims description 2
- 125000004250 isochroman-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])OC2([H])* 0.000 claims 128
- -1 Acetoxy, Nitro, Amino Chemical group 0.000 claims 104
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims 87
- 150000001875 compounds Chemical class 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- RPHFGEHBXPSYLK-UHFFFAOYSA-N methanamine;dihydrochloride Chemical compound Cl.Cl.NC RPHFGEHBXPSYLK-UHFFFAOYSA-N 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 206010015037 epilepsy Diseases 0.000 claims 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 4
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 4
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- WZFYVLITWYLKET-UHFFFAOYSA-N carboxy(methyl)azanium;chloride Chemical compound Cl.CNC(O)=O WZFYVLITWYLKET-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- SGQLCKFYRFFILX-UQKRIMTDSA-N C1CC2=C(C=CC=C2[C@@H](OC1)CN)C3=CC=NO3.Cl Chemical compound C1CC2=C(C=CC=C2[C@@H](OC1)CN)C3=CC=NO3.Cl SGQLCKFYRFFILX-UQKRIMTDSA-N 0.000 claims 1
- FDUPNUKHWNVVBA-ZOWNYOTGSA-N C1CC2=C(C=CC=C2[C@@H](OC1)CN)C3=CN=CO3.Cl Chemical compound C1CC2=C(C=CC=C2[C@@H](OC1)CN)C3=CN=CO3.Cl FDUPNUKHWNVVBA-ZOWNYOTGSA-N 0.000 claims 1
- SGQLCKFYRFFILX-PFEQFJNWSA-N C1CC2=C(C=CC=C2[C@H](OC1)CN)C3=CC=NO3.Cl Chemical compound C1CC2=C(C=CC=C2[C@H](OC1)CN)C3=CC=NO3.Cl SGQLCKFYRFFILX-PFEQFJNWSA-N 0.000 claims 1
- FDUPNUKHWNVVBA-BTQNPOSSSA-N C1CC2=C(C=CC=C2[C@H](OC1)CN)C3=CN=CO3.Cl Chemical compound C1CC2=C(C=CC=C2[C@H](OC1)CN)C3=CN=CO3.Cl FDUPNUKHWNVVBA-BTQNPOSSSA-N 0.000 claims 1
- LZADPNMPICUKTO-LBPRGKRZSA-N CNC[C@@H]1OCC2=C(C=CC=C12)C1=CN=CS1 Chemical compound CNC[C@@H]1OCC2=C(C=CC=C12)C1=CN=CS1 LZADPNMPICUKTO-LBPRGKRZSA-N 0.000 claims 1
- CKZUHVJSJXOHPP-AWEZNQCLSA-N CNC[C@@H]1OCC2=C(C=CC=C12)C1=NC=CN=C1 Chemical compound CNC[C@@H]1OCC2=C(C=CC=C12)C1=NC=CN=C1 CKZUHVJSJXOHPP-AWEZNQCLSA-N 0.000 claims 1
- ZBHJTCIEGVHSKX-AWEZNQCLSA-N CNC[C@@H]1OCC2=C(C=CC=C12)C1=NC=NC=C1 Chemical compound CNC[C@@H]1OCC2=C(C=CC=C12)C1=NC=NC=C1 ZBHJTCIEGVHSKX-AWEZNQCLSA-N 0.000 claims 1
- WYRAVUIZDQVKKS-KRWDZBQOSA-N CNC[C@@H]1OCCCC2=C1C=CC=C2C1=CC=NC=C1 Chemical compound CNC[C@@H]1OCCCC2=C1C=CC=C2C1=CC=NC=C1 WYRAVUIZDQVKKS-KRWDZBQOSA-N 0.000 claims 1
- WURFPXAADCULAU-HNNXBMFYSA-N CNC[C@@H]1OCCCC2=C1C=CC=C2C1=CON=C1 Chemical compound CNC[C@@H]1OCCCC2=C1C=CC=C2C1=CON=C1 WURFPXAADCULAU-HNNXBMFYSA-N 0.000 claims 1
- MBONJNFSABDBMJ-KRWDZBQOSA-N CNC[C@@H]1OCCCC2=C1C=CC=C2C=1C=NC=CC=1 Chemical compound CNC[C@@H]1OCCCC2=C1C=CC=C2C=1C=NC=CC=1 MBONJNFSABDBMJ-KRWDZBQOSA-N 0.000 claims 1
- LZADPNMPICUKTO-GFCCVEGCSA-N CNC[C@H]1OCC2=C(C=CC=C12)C1=CN=CS1 Chemical compound CNC[C@H]1OCC2=C(C=CC=C12)C1=CN=CS1 LZADPNMPICUKTO-GFCCVEGCSA-N 0.000 claims 1
- CKZUHVJSJXOHPP-CQSZACIVSA-N CNC[C@H]1OCC2=C(C=CC=C12)C1=NC=CN=C1 Chemical compound CNC[C@H]1OCC2=C(C=CC=C12)C1=NC=CN=C1 CKZUHVJSJXOHPP-CQSZACIVSA-N 0.000 claims 1
- ZBHJTCIEGVHSKX-CQSZACIVSA-N CNC[C@H]1OCC2=C(C=CC=C12)C1=NC=NC=C1 Chemical compound CNC[C@H]1OCC2=C(C=CC=C12)C1=NC=NC=C1 ZBHJTCIEGVHSKX-CQSZACIVSA-N 0.000 claims 1
- WYRAVUIZDQVKKS-QGZVFWFLSA-N CNC[C@H]1OCCCC2=C1C=CC=C2C1=CC=NC=C1 Chemical compound CNC[C@H]1OCCCC2=C1C=CC=C2C1=CC=NC=C1 WYRAVUIZDQVKKS-QGZVFWFLSA-N 0.000 claims 1
- WURFPXAADCULAU-OAHLLOKOSA-N CNC[C@H]1OCCCC2=C1C=CC=C2C1=CON=C1 Chemical compound CNC[C@H]1OCCCC2=C1C=CC=C2C1=CON=C1 WURFPXAADCULAU-OAHLLOKOSA-N 0.000 claims 1
- OAJYDRUKDNYVAT-MRXNPFEDSA-N CNC[C@H]1OCCCC2=C1C=CC=C2C1=NC=CN=C1 Chemical compound CNC[C@H]1OCCCC2=C1C=CC=C2C1=NC=CN=C1 OAJYDRUKDNYVAT-MRXNPFEDSA-N 0.000 claims 1
- MBONJNFSABDBMJ-QGZVFWFLSA-N CNC[C@H]1OCCCC2=C1C=CC=C2C=1C=NC=CC=1 Chemical compound CNC[C@H]1OCCCC2=C1C=CC=C2C=1C=NC=CC=1 MBONJNFSABDBMJ-QGZVFWFLSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- OMNFJMKYTOHIQR-FERBBOLQSA-N Cl.C(NC1CC1)[C@@H]1OCCc2c1cccc2-c1ccncc1 Chemical compound Cl.C(NC1CC1)[C@@H]1OCCc2c1cccc2-c1ccncc1 OMNFJMKYTOHIQR-FERBBOLQSA-N 0.000 claims 1
- OMNFJMKYTOHIQR-GMUIIQOCSA-N Cl.C(NC1CC1)[C@H]1OCCc2c1cccc2-c1ccncc1 Chemical compound Cl.C(NC1CC1)[C@H]1OCCc2c1cccc2-c1ccncc1 OMNFJMKYTOHIQR-GMUIIQOCSA-N 0.000 claims 1
- UGUDRJDRNJMGRZ-LMOVPXPDSA-N Cl.CCNC[C@@H]1OCCc2c1cccc2-c1ccncc1 Chemical compound Cl.CCNC[C@@H]1OCCc2c1cccc2-c1ccncc1 UGUDRJDRNJMGRZ-LMOVPXPDSA-N 0.000 claims 1
- UGUDRJDRNJMGRZ-UNTBIKODSA-N Cl.CCNC[C@H]1OCCc2c1cccc2-c1ccncc1 Chemical compound Cl.CCNC[C@H]1OCCc2c1cccc2-c1ccncc1 UGUDRJDRNJMGRZ-UNTBIKODSA-N 0.000 claims 1
- RSICQIIFYOAJPD-LMOVPXPDSA-N Cl.CNC[C@@H]1OCCCc2c1cccc2-c1ccccn1 Chemical compound Cl.CNC[C@@H]1OCCCc2c1cccc2-c1ccccn1 RSICQIIFYOAJPD-LMOVPXPDSA-N 0.000 claims 1
- IUYNGVIUDDOAOL-NTISSMGPSA-N Cl.CNC[C@@H]1OCCCc2c1cccc2-c1ccncn1 Chemical compound Cl.CNC[C@@H]1OCCCc2c1cccc2-c1ccncn1 IUYNGVIUDDOAOL-NTISSMGPSA-N 0.000 claims 1
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- 206010012335 Dependence Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000019430 Motor disease Diseases 0.000 claims 1
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| CN117177977A (zh) * | 2021-04-10 | 2023-12-05 | 住友制药株式会社 | 二环吡啶衍生物 |
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- 2018-08-01 JP JP2020505414A patent/JP7191085B2/ja active Active
- 2018-08-01 SG SG11202000669VA patent/SG11202000669VA/en unknown
- 2018-08-01 KR KR1020207006086A patent/KR20200036008A/ko not_active Withdrawn
- 2018-08-01 BR BR112020001433-8A patent/BR112020001433A2/pt not_active Application Discontinuation
- 2018-08-01 MX MX2020000523A patent/MX2020000523A/es unknown
- 2018-08-01 CA CA3070993A patent/CA3070993C/en active Active
- 2018-08-01 WO PCT/US2018/044854 patent/WO2019028165A1/en not_active Ceased
- 2018-08-01 EA EA202090414A patent/EA202090414A1/ru unknown
- 2018-08-01 CN CN201880047336.XA patent/CN111183138A/zh active Pending
- 2018-08-01 AU AU2018312559A patent/AU2018312559B2/en not_active Ceased
- 2018-08-01 EP EP18756100.6A patent/EP3661929B1/en active Active
- 2018-08-01 US US16/051,863 patent/US10780074B2/en active Active
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2020
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- 2020-08-12 US US16/991,771 patent/US11491133B2/en active Active
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