JP2020529419A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- GKFGWFLXOQTVDX-UQKRIMTDSA-N Cl.CNC[C@@H]1OCCCc2c1cccc2-c1cncs1 Chemical compound Cl.CNC[C@@H]1OCCCc2c1cccc2-c1cncs1 GKFGWFLXOQTVDX-UQKRIMTDSA-N 0.000 claims 1
- DOSJVVWOGCHHNS-LMOVPXPDSA-N Cl.CNC[C@@H]1OCCc2c1cccc2-c1ccccc1 Chemical compound Cl.CNC[C@@H]1OCCc2c1cccc2-c1ccccc1 DOSJVVWOGCHHNS-LMOVPXPDSA-N 0.000 claims 1
- HDRCGUHHRPUDCA-RSAXXLAASA-N Cl.CNC[C@@H]1OCc2c1cccc2-c1cccnc1 Chemical compound Cl.CNC[C@@H]1OCc2c1cccc2-c1cccnc1 HDRCGUHHRPUDCA-RSAXXLAASA-N 0.000 claims 1
- QHQXACQMCVWBED-RSAXXLAASA-N Cl.CNC[C@@H]1OCc2c1cccc2-c1ccncc1 Chemical compound Cl.CNC[C@@H]1OCc2c1cccc2-c1ccncc1 QHQXACQMCVWBED-RSAXXLAASA-N 0.000 claims 1
- RSICQIIFYOAJPD-UNTBIKODSA-N Cl.CNC[C@H]1OCCCc2c1cccc2-c1ccccn1 Chemical compound Cl.CNC[C@H]1OCCCc2c1cccc2-c1ccccn1 RSICQIIFYOAJPD-UNTBIKODSA-N 0.000 claims 1
- IUYNGVIUDDOAOL-PKLMIRHRSA-N Cl.CNC[C@H]1OCCCc2c1cccc2-c1ccncn1 Chemical compound Cl.CNC[C@H]1OCCCc2c1cccc2-c1ccncn1 IUYNGVIUDDOAOL-PKLMIRHRSA-N 0.000 claims 1
- GKFGWFLXOQTVDX-PFEQFJNWSA-N Cl.CNC[C@H]1OCCCc2c1cccc2-c1cncs1 Chemical compound Cl.CNC[C@H]1OCCCc2c1cccc2-c1cncs1 GKFGWFLXOQTVDX-PFEQFJNWSA-N 0.000 claims 1
- DOSJVVWOGCHHNS-UNTBIKODSA-N Cl.CNC[C@H]1OCCc2c1cccc2-c1ccccc1 Chemical compound Cl.CNC[C@H]1OCCc2c1cccc2-c1ccccc1 DOSJVVWOGCHHNS-UNTBIKODSA-N 0.000 claims 1
- HDRCGUHHRPUDCA-XFULWGLBSA-N Cl.CNC[C@H]1OCc2c1cccc2-c1cccnc1 Chemical compound Cl.CNC[C@H]1OCc2c1cccc2-c1cccnc1 HDRCGUHHRPUDCA-XFULWGLBSA-N 0.000 claims 1
- QHQXACQMCVWBED-XFULWGLBSA-N Cl.CNC[C@H]1OCc2c1cccc2-c1ccncc1 Chemical compound Cl.CNC[C@H]1OCc2c1cccc2-c1ccncc1 QHQXACQMCVWBED-XFULWGLBSA-N 0.000 claims 1
- UWWADOIEQBXRBI-NTEVMMBTSA-N Cl.Cl.CNC[C@@H]1OCCCc2c1cccc2-c1ccnc(C)c1 Chemical compound Cl.Cl.CNC[C@@H]1OCCCc2c1cccc2-c1ccnc(C)c1 UWWADOIEQBXRBI-NTEVMMBTSA-N 0.000 claims 1
- UWWADOIEQBXRBI-JPKZNVRTSA-N Cl.Cl.CNC[C@H]1OCCCc2c1cccc2-c1ccnc(C)c1 Chemical compound Cl.Cl.CNC[C@H]1OCCCc2c1cccc2-c1ccnc(C)c1 UWWADOIEQBXRBI-JPKZNVRTSA-N 0.000 claims 1
- AQKNMERRPVLDRQ-ZEECNFPPSA-N Cl.Cl.Cc1cc(ccn1)-c1cccc2[C@@H](CN)OCCCc12 Chemical compound Cl.Cl.Cc1cc(ccn1)-c1cccc2[C@@H](CN)OCCCc12 AQKNMERRPVLDRQ-ZEECNFPPSA-N 0.000 claims 1
- AQKNMERRPVLDRQ-RMRYJAPISA-N Cl.Cl.Cc1cc(ccn1)-c1cccc2[C@H](CN)OCCCc12 Chemical compound Cl.Cl.Cc1cc(ccn1)-c1cccc2[C@H](CN)OCCCc12 AQKNMERRPVLDRQ-RMRYJAPISA-N 0.000 claims 1
- HAMWHXOIHFHCMK-NTISSMGPSA-N Cl.NC[C@@H]1OCCCc2c1cccc2-c1ccccn1 Chemical compound Cl.NC[C@@H]1OCCCc2c1cccc2-c1ccccn1 HAMWHXOIHFHCMK-NTISSMGPSA-N 0.000 claims 1
- PQHUFNPRVHLNMB-ZOWNYOTGSA-N Cl.NC[C@@H]1OCCCc2c1cccc2-c1cncs1 Chemical compound Cl.NC[C@@H]1OCCCc2c1cccc2-c1cncs1 PQHUFNPRVHLNMB-ZOWNYOTGSA-N 0.000 claims 1
- WIVYGYCDSQTDNB-NTISSMGPSA-N Cl.NC[C@@H]1OCCc2c1cccc2-c1ccccc1 Chemical compound Cl.NC[C@@H]1OCCc2c1cccc2-c1ccccc1 WIVYGYCDSQTDNB-NTISSMGPSA-N 0.000 claims 1
- HGDAUESOVWFXAP-UQKRIMTDSA-N Cl.NC[C@@H]1OCc2c1cccc2-c1cccnc1 Chemical compound Cl.NC[C@@H]1OCc2c1cccc2-c1cccnc1 HGDAUESOVWFXAP-UQKRIMTDSA-N 0.000 claims 1
- HQVQHMRJPABFNX-UQKRIMTDSA-N Cl.NC[C@@H]1OCc2c1cccc2-c1ccncc1 Chemical compound Cl.NC[C@@H]1OCc2c1cccc2-c1ccncc1 HQVQHMRJPABFNX-UQKRIMTDSA-N 0.000 claims 1
- HAMWHXOIHFHCMK-PKLMIRHRSA-N Cl.NC[C@H]1OCCCc2c1cccc2-c1ccccn1 Chemical compound Cl.NC[C@H]1OCCCc2c1cccc2-c1ccccn1 HAMWHXOIHFHCMK-PKLMIRHRSA-N 0.000 claims 1
- PQHUFNPRVHLNMB-BTQNPOSSSA-N Cl.NC[C@H]1OCCCc2c1cccc2-c1cncs1 Chemical compound Cl.NC[C@H]1OCCCc2c1cccc2-c1cncs1 PQHUFNPRVHLNMB-BTQNPOSSSA-N 0.000 claims 1
- WIVYGYCDSQTDNB-PKLMIRHRSA-N Cl.NC[C@H]1OCCc2c1cccc2-c1ccccc1 Chemical compound Cl.NC[C@H]1OCCc2c1cccc2-c1ccccc1 WIVYGYCDSQTDNB-PKLMIRHRSA-N 0.000 claims 1
- HGDAUESOVWFXAP-PFEQFJNWSA-N Cl.NC[C@H]1OCc2c1cccc2-c1cccnc1 Chemical compound Cl.NC[C@H]1OCc2c1cccc2-c1cccnc1 HGDAUESOVWFXAP-PFEQFJNWSA-N 0.000 claims 1
- HQVQHMRJPABFNX-PFEQFJNWSA-N Cl.NC[C@H]1OCc2c1cccc2-c1ccncc1 Chemical compound Cl.NC[C@H]1OCc2c1cccc2-c1ccncc1 HQVQHMRJPABFNX-PFEQFJNWSA-N 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000019430 Motor disease Diseases 0.000 claims 1
- DRCHHYRPIRFNCI-CQSZACIVSA-N N1=C(C=CC=C1)C1=C2CO[C@@H](C2=CC=C1)CN Chemical compound N1=C(C=CC=C1)C1=C2CO[C@@H](C2=CC=C1)CN DRCHHYRPIRFNCI-CQSZACIVSA-N 0.000 claims 1
- DRCHHYRPIRFNCI-AWEZNQCLSA-N N1=C(C=CC=C1)C1=C2CO[C@H](C2=CC=C1)CN Chemical compound N1=C(C=CC=C1)C1=C2CO[C@H](C2=CC=C1)CN DRCHHYRPIRFNCI-AWEZNQCLSA-N 0.000 claims 1
- QBIZSKKOLCTBEV-CYBMUJFWSA-N N1=C(C=NC=C1)C1=C2CO[C@@H](C2=CC=C1)CN Chemical compound N1=C(C=NC=C1)C1=C2CO[C@@H](C2=CC=C1)CN QBIZSKKOLCTBEV-CYBMUJFWSA-N 0.000 claims 1
- QBIZSKKOLCTBEV-ZDUSSCGKSA-N N1=C(C=NC=C1)C1=C2CO[C@H](C2=CC=C1)CN Chemical compound N1=C(C=NC=C1)C1=C2CO[C@H](C2=CC=C1)CN QBIZSKKOLCTBEV-ZDUSSCGKSA-N 0.000 claims 1
- JSEIDBRHHIBQHP-OAHLLOKOSA-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-OAHLLOKOSA-N 0.000 claims 1
- WZAQDLOFIWJDJL-INIZCTEOSA-N N1=CC(=CC=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN Chemical compound N1=CC(=CC=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN WZAQDLOFIWJDJL-INIZCTEOSA-N 0.000 claims 1
- WZAQDLOFIWJDJL-MRXNPFEDSA-N N1=CC(=CC=C1)C1=CC=CC=2[C@H](OCCCC=21)CN Chemical compound N1=CC(=CC=C1)C1=CC=CC=2[C@H](OCCCC=21)CN WZAQDLOFIWJDJL-MRXNPFEDSA-N 0.000 claims 1
- XIHGEFTUFLZXAU-INIZCTEOSA-N N1=CC=C(C=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN Chemical compound N1=CC=C(C=C1)C1=CC=CC=2[C@@H](OCCCC=21)CN XIHGEFTUFLZXAU-INIZCTEOSA-N 0.000 claims 1
- XIHGEFTUFLZXAU-MRXNPFEDSA-N N1=CC=C(C=C1)C1=CC=CC=2[C@H](OCCCC=21)CN Chemical compound N1=CC=C(C=C1)C1=CC=CC=2[C@H](OCCCC=21)CN XIHGEFTUFLZXAU-MRXNPFEDSA-N 0.000 claims 1
- OLKRMTXPWZDTIH-CYBMUJFWSA-N N1=CN=C(C=C1)C1=C2CO[C@@H](C2=CC=C1)CN Chemical compound N1=CN=C(C=C1)C1=C2CO[C@@H](C2=CC=C1)CN OLKRMTXPWZDTIH-CYBMUJFWSA-N 0.000 claims 1
- OLKRMTXPWZDTIH-ZDUSSCGKSA-N N1=CN=C(C=C1)C1=C2CO[C@H](C2=CC=C1)CN Chemical compound N1=CN=C(C=C1)C1=C2CO[C@H](C2=CC=C1)CN OLKRMTXPWZDTIH-ZDUSSCGKSA-N 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- JVTADAOUTKJRAX-LLVKDONJSA-N S1C=NC=C1C1=C2CO[C@@H](C2=CC=C1)CN Chemical compound S1C=NC=C1C1=C2CO[C@@H](C2=CC=C1)CN JVTADAOUTKJRAX-LLVKDONJSA-N 0.000 claims 1
- JVTADAOUTKJRAX-NSHDSACASA-N S1C=NC=C1C1=C2CO[C@H](C2=CC=C1)CN Chemical compound S1C=NC=C1C1=C2CO[C@H](C2=CC=C1)CN JVTADAOUTKJRAX-NSHDSACASA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000013404 behavioral symptom Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000025307 bipolar depression Diseases 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000003104 endogenous depression Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 0 C*(C)(CN(*)*)C(c1c2c(*)c(*)c(*)c1*)O*C2(*)O* Chemical compound C*(C)(CN(*)*)C(c1c2c(*)c(*)c(*)c1*)O*C2(*)O* 0.000 description 62
- RHMFEKPUAJCXQR-QGZVFWFLSA-N CN(C)C[C@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CN(C)C[C@H](c1ccc2)OCCc1c2-c1ccncc1 RHMFEKPUAJCXQR-QGZVFWFLSA-N 0.000 description 3
- ISVMISBAMCIJMA-KRWDZBQOSA-N CCNC[C@@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CCNC[C@@H](c1ccc2)OCCc1c2-c1ccncc1 ISVMISBAMCIJMA-KRWDZBQOSA-N 0.000 description 2
- ISVMISBAMCIJMA-QGZVFWFLSA-N CCNC[C@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CCNC[C@H](c1ccc2)OCCc1c2-c1ccncc1 ISVMISBAMCIJMA-QGZVFWFLSA-N 0.000 description 2
- RHMFEKPUAJCXQR-UHFFFAOYSA-N CN(C)CC(c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CN(C)CC(c1ccc2)OCCc1c2-c1ccncc1 RHMFEKPUAJCXQR-UHFFFAOYSA-N 0.000 description 2
- ZWSGVGGSNWUJCX-INIZCTEOSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1ccncc1 ZWSGVGGSNWUJCX-INIZCTEOSA-N 0.000 description 2
- ZWSGVGGSNWUJCX-MRXNPFEDSA-N CNC[C@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1ccncc1 ZWSGVGGSNWUJCX-MRXNPFEDSA-N 0.000 description 2
- HAOGNAYABVWBCH-MRXNPFEDSA-N CNC[C@H](c1ccc2)OCCc1c2-c1ncccc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1ncccc1 HAOGNAYABVWBCH-MRXNPFEDSA-N 0.000 description 2
- VVBGSVUTWBGTCG-HNNXBMFYSA-N NC[C@@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound NC[C@@H](c1ccc2)OCCc1c2-c1ccncc1 VVBGSVUTWBGTCG-HNNXBMFYSA-N 0.000 description 2
- VVBGSVUTWBGTCG-OAHLLOKOSA-N NC[C@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1ccncc1 VVBGSVUTWBGTCG-OAHLLOKOSA-N 0.000 description 2
- GZHLNPAGWJMQTA-OAHLLOKOSA-N NC[C@H](c1ccc2)OCCc1c2-c1ncccc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1ncccc1 GZHLNPAGWJMQTA-OAHLLOKOSA-N 0.000 description 2
- OKMSNFKOXRWYJN-GOSISDBHSA-N C([C@H](c1ccc2)OCCc1c2-c1ccncc1)NC1CC1 Chemical compound C([C@H](c1ccc2)OCCc1c2-c1ccncc1)NC1CC1 OKMSNFKOXRWYJN-GOSISDBHSA-N 0.000 description 1
- UETFVRPRBLJCOT-MSOGKRANSA-N C/C=C(/C(/C)=N/OC#C)\C1=C(C)[C@H](CN)OCC1 Chemical compound C/C=C(/C(/C)=N/OC#C)\C1=C(C)[C@H](CN)OCC1 UETFVRPRBLJCOT-MSOGKRANSA-N 0.000 description 1
- RZTYSDLFOVQXEI-JBJDWBBVSA-N C/C=C(/c1c[nH]cn1)\C(CCO[C@H]1CN)=C1C=C Chemical compound C/C=C(/c1c[nH]cn1)\C(CCO[C@H]1CN)=C1C=C RZTYSDLFOVQXEI-JBJDWBBVSA-N 0.000 description 1
- VQVMGTQLPPZYIG-XPMGFOTESA-N C/C=C(/c1c[o]cn1)\C(CCO[C@@H]1CNC)=C1C#C Chemical compound C/C=C(/c1c[o]cn1)\C(CCO[C@@H]1CNC)=C1C#C VQVMGTQLPPZYIG-XPMGFOTESA-N 0.000 description 1
- VPXDTOZXJGAACB-MYLOROHHSA-N C/C=C(\C=C(\C)/N=C)/c1c(CCO[C@@H]2CNC)c2ccc1 Chemical compound C/C=C(\C=C(\C)/N=C)/c1c(CCO[C@@H]2CNC)c2ccc1 VPXDTOZXJGAACB-MYLOROHHSA-N 0.000 description 1
- REHGLHCTSAGPBV-PLNGDYQASA-N C/C=C\C(C(CNC)OCC1)=C1C(c1ncc[nH]1)=C Chemical compound C/C=C\C(C(CNC)OCC1)=C1C(c1ncc[nH]1)=C REHGLHCTSAGPBV-PLNGDYQASA-N 0.000 description 1
- XQPAIIQAEZZFNN-WSNITJDQSA-N C/C=C\C([C@H](CNC)OCC1)=C1C(c1cnc[s]1)=C Chemical compound C/C=C\C([C@H](CNC)OCC1)=C1C(c1cnc[s]1)=C XQPAIIQAEZZFNN-WSNITJDQSA-N 0.000 description 1
- WZQBVDRBERNAMD-YWCUFVOSSA-N CC1C=CC([C@@H](CN)OCCC2)=C2C1c1cnccn1 Chemical compound CC1C=CC([C@@H](CN)OCCC2)=C2C1c1cnccn1 WZQBVDRBERNAMD-YWCUFVOSSA-N 0.000 description 1
- BDIWSJPWFJLYJS-CUMGRINNSA-N CC1N=CC=NC1c1c(CO[C@H]2CNC)c2ccc1 Chemical compound CC1N=CC=NC1c1c(CO[C@H]2CNC)c2ccc1 BDIWSJPWFJLYJS-CUMGRINNSA-N 0.000 description 1
- WWIFQKWJDOXLKH-UHFFFAOYSA-O CC=C(c1cnc[s]1)C(CCCOC1C[NH3+])=C1C=C Chemical compound CC=C(c1cnc[s]1)C(CCCOC1C[NH3+])=C1C=C WWIFQKWJDOXLKH-UHFFFAOYSA-O 0.000 description 1
- RJNMVAXNJXNVFR-ZDUSSCGKSA-N CCO[C@@H](CN)c1cccc(-c2cnc[o]2)c1C Chemical compound CCO[C@@H](CN)c1cccc(-c2cnc[o]2)c1C RJNMVAXNJXNVFR-ZDUSSCGKSA-N 0.000 description 1
- RHMFEKPUAJCXQR-KRWDZBQOSA-N CN(C)C[C@@H](c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CN(C)C[C@@H](c1ccc2)OCCc1c2-c1ccncc1 RHMFEKPUAJCXQR-KRWDZBQOSA-N 0.000 description 1
- UZHNRVTUWWODAD-UHFFFAOYSA-N CNC(C1)C1(c1ccc2)OCCCc1c2-c1ccn[o]1 Chemical compound CNC(C1)C1(c1ccc2)OCCCc1c2-c1ccn[o]1 UZHNRVTUWWODAD-UHFFFAOYSA-N 0.000 description 1
- MGDUXCGFIUKYMQ-UHFFFAOYSA-N CNCC(c1c2)OCCc1ccc2-c1ncncc1 Chemical compound CNCC(c1c2)OCCc1ccc2-c1ncncc1 MGDUXCGFIUKYMQ-UHFFFAOYSA-N 0.000 description 1
- XLGGFEUDFARXGE-UHFFFAOYSA-N CNCC(c1ccc2)OCCc1c2-c1c[o]nc1 Chemical compound CNCC(c1ccc2)OCCc1c2-c1c[o]nc1 XLGGFEUDFARXGE-UHFFFAOYSA-N 0.000 description 1
- ZWSGVGGSNWUJCX-UHFFFAOYSA-N CNCC(c1ccc2)OCCc1c2-c1ccncc1 Chemical compound CNCC(c1ccc2)OCCc1c2-c1ccncc1 ZWSGVGGSNWUJCX-UHFFFAOYSA-N 0.000 description 1
- CXHMNKQVTDPGRY-UHFFFAOYSA-N CNCC(c1ccc2)OCCc1c2-c1cnc[s]1 Chemical compound CNCC(c1ccc2)OCCc1c2-c1cnc[s]1 CXHMNKQVTDPGRY-UHFFFAOYSA-N 0.000 description 1
- WXGLZJCTKWGYCP-UHFFFAOYSA-N CNCC(c1ccc2)OCCc1c2-c1cnncc1 Chemical compound CNCC(c1ccc2)OCCc1c2-c1cnncc1 WXGLZJCTKWGYCP-UHFFFAOYSA-N 0.000 description 1
- HAOGNAYABVWBCH-UHFFFAOYSA-N CNCC(c1ccc2)OCCc1c2-c1ncccc1 Chemical compound CNCC(c1ccc2)OCCc1c2-c1ncccc1 HAOGNAYABVWBCH-UHFFFAOYSA-N 0.000 description 1
- BEORYSXZTYWOJO-UHFFFAOYSA-N CNCC(c1ccc2)OCCc1c2-c1ncncc1 Chemical compound CNCC(c1ccc2)OCCc1c2-c1ncncc1 BEORYSXZTYWOJO-UHFFFAOYSA-N 0.000 description 1
- HNNJHMQKCOHIAZ-UHFFFAOYSA-N CNCC1OCCC2=C1C=CCC2c1cnccn1 Chemical compound CNCC1OCCC2=C1C=CCC2c1cnccn1 HNNJHMQKCOHIAZ-UHFFFAOYSA-N 0.000 description 1
- UZFIOCRYPPMYFZ-AWEZNQCLSA-N CNC[C@@H](c1ccc2)OCCCc1c2-c1cnc[o]1 Chemical compound CNC[C@@H](c1ccc2)OCCCc1c2-c1cnc[o]1 UZFIOCRYPPMYFZ-AWEZNQCLSA-N 0.000 description 1
- DWLDWOVJNRDJSB-AWEZNQCLSA-N CNC[C@@H](c1ccc2)OCCCc1c2-c1cnc[s]1 Chemical compound CNC[C@@H](c1ccc2)OCCCc1c2-c1cnc[s]1 DWLDWOVJNRDJSB-AWEZNQCLSA-N 0.000 description 1
- KAHHALSNBQNRTP-INIZCTEOSA-N CNC[C@@H](c1ccc2)OCCCc1c2-c1ncncc1 Chemical compound CNC[C@@H](c1ccc2)OCCCc1c2-c1ncncc1 KAHHALSNBQNRTP-INIZCTEOSA-N 0.000 description 1
- XPWWPURAQZMPBW-ZDUSSCGKSA-N CNC[C@@H](c1ccc2)OCCc1c2-[n]1cnnc1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-[n]1cnnc1 XPWWPURAQZMPBW-ZDUSSCGKSA-N 0.000 description 1
- UVDQKESSGDFTIR-AWEZNQCLSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1c[nH]nc1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1c[nH]nc1 UVDQKESSGDFTIR-AWEZNQCLSA-N 0.000 description 1
- PIOYZCYGCMYGMC-ZDUSSCGKSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1cnc[o]1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1cnc[o]1 PIOYZCYGCMYGMC-ZDUSSCGKSA-N 0.000 description 1
- YJPXLGQWGPWPCU-HNNXBMFYSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1cnccn1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1cnccn1 YJPXLGQWGPWPCU-HNNXBMFYSA-N 0.000 description 1
- WXGLZJCTKWGYCP-HNNXBMFYSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1cnncc1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1cnncc1 WXGLZJCTKWGYCP-HNNXBMFYSA-N 0.000 description 1
- IPPXMXNOVSZHSB-AWEZNQCLSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1n[o]cc1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1n[o]cc1 IPPXMXNOVSZHSB-AWEZNQCLSA-N 0.000 description 1
- GRAJNSQUHJJWIJ-ZDUSSCGKSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1ncc[o]1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1ncc[o]1 GRAJNSQUHJJWIJ-ZDUSSCGKSA-N 0.000 description 1
- BEORYSXZTYWOJO-HNNXBMFYSA-N CNC[C@@H](c1ccc2)OCCc1c2-c1ncncc1 Chemical compound CNC[C@@H](c1ccc2)OCCc1c2-c1ncncc1 BEORYSXZTYWOJO-HNNXBMFYSA-N 0.000 description 1
- QUSNKZDBAXBOGB-OAHLLOKOSA-N CNC[C@H](c1ccc2)OCCCc1c2-c1ccn[o]1 Chemical compound CNC[C@H](c1ccc2)OCCCc1c2-c1ccn[o]1 QUSNKZDBAXBOGB-OAHLLOKOSA-N 0.000 description 1
- DWLDWOVJNRDJSB-CQSZACIVSA-N CNC[C@H](c1ccc2)OCCCc1c2-c1cnc[s]1 Chemical compound CNC[C@H](c1ccc2)OCCCc1c2-c1cnc[s]1 DWLDWOVJNRDJSB-CQSZACIVSA-N 0.000 description 1
- KAHHALSNBQNRTP-MRXNPFEDSA-N CNC[C@H](c1ccc2)OCCCc1c2-c1ncncc1 Chemical compound CNC[C@H](c1ccc2)OCCCc1c2-c1ncncc1 KAHHALSNBQNRTP-MRXNPFEDSA-N 0.000 description 1
- GNUQFLLMEZMTHR-CQSZACIVSA-N CNC[C@H](c1ccc2)OCCc1c2-[n]1nccc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-[n]1nccc1 GNUQFLLMEZMTHR-CQSZACIVSA-N 0.000 description 1
- IDXLLWZUBMSKAM-QGZVFWFLSA-N CNC[C@H](c1ccc2)OCCc1c2-c1ccccc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1ccccc1 IDXLLWZUBMSKAM-QGZVFWFLSA-N 0.000 description 1
- ARTWCOLGUOHCJP-CQSZACIVSA-N CNC[C@H](c1ccc2)OCCc1c2-c1ccn[o]1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1ccn[o]1 ARTWCOLGUOHCJP-CQSZACIVSA-N 0.000 description 1
- CXHMNKQVTDPGRY-CYBMUJFWSA-N CNC[C@H](c1ccc2)OCCc1c2-c1cnc[s]1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1cnc[s]1 CXHMNKQVTDPGRY-CYBMUJFWSA-N 0.000 description 1
- DQOWUSBPSFITII-MRXNPFEDSA-N CNC[C@H](c1ccc2)OCCc1c2-c1cnccc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1cnccc1 DQOWUSBPSFITII-MRXNPFEDSA-N 0.000 description 1
- WXGLZJCTKWGYCP-OAHLLOKOSA-N CNC[C@H](c1ccc2)OCCc1c2-c1cnncc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1cnncc1 WXGLZJCTKWGYCP-OAHLLOKOSA-N 0.000 description 1
- IPPXMXNOVSZHSB-CQSZACIVSA-N CNC[C@H](c1ccc2)OCCc1c2-c1n[o]cc1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1n[o]cc1 IPPXMXNOVSZHSB-CQSZACIVSA-N 0.000 description 1
- DCOTWPWIXLDDHK-CYBMUJFWSA-N CNC[C@H](c1ccc2)OCCc1c2-c1ncc[nH]1 Chemical compound CNC[C@H](c1ccc2)OCCc1c2-c1ncc[nH]1 DCOTWPWIXLDDHK-CYBMUJFWSA-N 0.000 description 1
- MZHUOHDIHIAQOY-OAHLLOKOSA-N CNC[C@H]1OCCC(C2)=C1C=CC=C2c1c[nH]cn1 Chemical compound CNC[C@H]1OCCC(C2)=C1C=CC=C2c1c[nH]cn1 MZHUOHDIHIAQOY-OAHLLOKOSA-N 0.000 description 1
- XLGGFEUDFARXGE-CQSZACIVSA-N CNC[C@H]1OCCc2c1cccc2-c1c[o]nc1 Chemical compound CNC[C@H]1OCCc2c1cccc2-c1c[o]nc1 XLGGFEUDFARXGE-CQSZACIVSA-N 0.000 description 1
- KZDNWKVKDLTDHB-KRWDZBQOSA-N Cc1cc(-c2c(CCO[C@H]3CN)c3ccc2)cc(C)n1 Chemical compound Cc1cc(-c2c(CCO[C@H]3CN)c3ccc2)cc(C)n1 KZDNWKVKDLTDHB-KRWDZBQOSA-N 0.000 description 1
- TZALQHZABTWYAR-QGZVFWFLSA-N Cc1nccc(-c2c(CCCO[C@@H]3CN)c3ccc2)c1 Chemical compound Cc1nccc(-c2c(CCCO[C@@H]3CN)c3ccc2)c1 TZALQHZABTWYAR-QGZVFWFLSA-N 0.000 description 1
- XJVOVDSVAUOXCJ-GOSISDBHSA-N Cc1nccc(-c2c(CCCO[C@@H]3CNC)c3ccc2)c1 Chemical compound Cc1nccc(-c2c(CCCO[C@@H]3CNC)c3ccc2)c1 XJVOVDSVAUOXCJ-GOSISDBHSA-N 0.000 description 1
- VAUJJBXDQULSKW-MRXNPFEDSA-N Cc1nccc(-c2c(CCO[C@@H]3CN)c3ccc2)c1 Chemical compound Cc1nccc(-c2c(CCO[C@@H]3CN)c3ccc2)c1 VAUJJBXDQULSKW-MRXNPFEDSA-N 0.000 description 1
- VAUJJBXDQULSKW-INIZCTEOSA-N Cc1nccc(-c2c(CCO[C@H]3CN)c3ccc2)c1 Chemical compound Cc1nccc(-c2c(CCO[C@H]3CN)c3ccc2)c1 VAUJJBXDQULSKW-INIZCTEOSA-N 0.000 description 1
- VBDXZYSHLYSHLC-KRWDZBQOSA-N Cc1nccc(-c2c(CCO[C@H]3CNC)c3ccc2)c1 Chemical compound Cc1nccc(-c2c(CCO[C@H]3CNC)c3ccc2)c1 VBDXZYSHLYSHLC-KRWDZBQOSA-N 0.000 description 1
- AQYOLTXQBYHPBX-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1cccnn1 Chemical compound NCC(c1ccc2)OCCc1c2-c1cccnn1 AQYOLTXQBYHPBX-UHFFFAOYSA-N 0.000 description 1
- VVBGSVUTWBGTCG-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1ccncc1 Chemical compound NCC(c1ccc2)OCCc1c2-c1ccncc1 VVBGSVUTWBGTCG-UHFFFAOYSA-N 0.000 description 1
- ITWNCCJEWGAJEU-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1cnc[s]1 Chemical compound NCC(c1ccc2)OCCc1c2-c1cnc[s]1 ITWNCCJEWGAJEU-UHFFFAOYSA-N 0.000 description 1
- NQBVAJAKZGKOPM-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1cnccc1 Chemical compound NCC(c1ccc2)OCCc1c2-c1cnccc1 NQBVAJAKZGKOPM-UHFFFAOYSA-N 0.000 description 1
- WSZBILGVMCLFNK-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1cnccn1 Chemical compound NCC(c1ccc2)OCCc1c2-c1cnccn1 WSZBILGVMCLFNK-UHFFFAOYSA-N 0.000 description 1
- XYRVATVHFMGOES-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1ncc[nH]1 Chemical compound NCC(c1ccc2)OCCc1c2-c1ncc[nH]1 XYRVATVHFMGOES-UHFFFAOYSA-N 0.000 description 1
- GZHLNPAGWJMQTA-UHFFFAOYSA-N NCC(c1ccc2)OCCc1c2-c1ncccc1 Chemical compound NCC(c1ccc2)OCCc1c2-c1ncccc1 GZHLNPAGWJMQTA-UHFFFAOYSA-N 0.000 description 1
- XDKWDXLJNUHBQZ-UHFFFAOYSA-N NCC1OCCc(cc2)c1cc2-c1ncncc1 Chemical compound NCC1OCCc(cc2)c1cc2-c1ncncc1 XDKWDXLJNUHBQZ-UHFFFAOYSA-N 0.000 description 1
- IUMRGYSIBGPGAI-AWEZNQCLSA-N NC[C@@H](c1ccc2)OCCCc1c2-c1ccn[o]1 Chemical compound NC[C@@H](c1ccc2)OCCCc1c2-c1ccn[o]1 IUMRGYSIBGPGAI-AWEZNQCLSA-N 0.000 description 1
- OMZBIGWLGDIKPT-ZDUSSCGKSA-N NC[C@@H](c1ccc2)OCCCc1c2-c1cnc[o]1 Chemical compound NC[C@@H](c1ccc2)OCCCc1c2-c1cnc[o]1 OMZBIGWLGDIKPT-ZDUSSCGKSA-N 0.000 description 1
- ZKNURQCAULJISA-ZDUSSCGKSA-N NC[C@@H](c1ccc2)OCCc1c2-c1c[nH]nc1 Chemical compound NC[C@@H](c1ccc2)OCCc1c2-c1c[nH]nc1 ZKNURQCAULJISA-ZDUSSCGKSA-N 0.000 description 1
- ITWNCCJEWGAJEU-LBPRGKRZSA-N NC[C@@H](c1ccc2)OCCc1c2-c1cnc[s]1 Chemical compound NC[C@@H](c1ccc2)OCCc1c2-c1cnc[s]1 ITWNCCJEWGAJEU-LBPRGKRZSA-N 0.000 description 1
- OTHYENXSAUFRTA-AWEZNQCLSA-N NC[C@@H](c1ccc2)OCCc1c2-c1cnncc1 Chemical compound NC[C@@H](c1ccc2)OCCc1c2-c1cnncc1 OTHYENXSAUFRTA-AWEZNQCLSA-N 0.000 description 1
- KSMLRAMOZIIJPK-LBPRGKRZSA-N NC[C@@H](c1ccc2)OCCc1c2-c1ncc[o]1 Chemical compound NC[C@@H](c1ccc2)OCCc1c2-c1ncc[o]1 KSMLRAMOZIIJPK-LBPRGKRZSA-N 0.000 description 1
- RKGIMVPUGKKTPK-AWEZNQCLSA-N NC[C@@H](c1ccc2)OCCc1c2-c1ncncc1 Chemical compound NC[C@@H](c1ccc2)OCCc1c2-c1ncncc1 RKGIMVPUGKKTPK-AWEZNQCLSA-N 0.000 description 1
- OMZBIGWLGDIKPT-CYBMUJFWSA-N NC[C@H](c1ccc2)OCCCc1c2-c1cnc[o]1 Chemical compound NC[C@H](c1ccc2)OCCCc1c2-c1cnc[o]1 OMZBIGWLGDIKPT-CYBMUJFWSA-N 0.000 description 1
- ZYEVHKATZIUGJI-CYBMUJFWSA-N NC[C@H](c1ccc2)OCCCc1c2-c1cnc[s]1 Chemical compound NC[C@H](c1ccc2)OCCCc1c2-c1cnc[s]1 ZYEVHKATZIUGJI-CYBMUJFWSA-N 0.000 description 1
- WBZGRQQSBUZPFL-MRXNPFEDSA-N NC[C@H](c1ccc2)OCCCc1c2-c1ncccc1 Chemical compound NC[C@H](c1ccc2)OCCCc1c2-c1ncccc1 WBZGRQQSBUZPFL-MRXNPFEDSA-N 0.000 description 1
- WVZNTAKTGXXZRR-CYBMUJFWSA-N NC[C@H](c1ccc2)OCCc1c2-c1c[nH]cn1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1c[nH]cn1 WVZNTAKTGXXZRR-CYBMUJFWSA-N 0.000 description 1
- PXOJGCAKYPJVTC-CYBMUJFWSA-N NC[C@H](c1ccc2)OCCc1c2-c1c[o]cn1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1c[o]cn1 PXOJGCAKYPJVTC-CYBMUJFWSA-N 0.000 description 1
- RNURLLFFAZCZTG-CYBMUJFWSA-N NC[C@H](c1ccc2)OCCc1c2-c1c[o]nc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1c[o]nc1 RNURLLFFAZCZTG-CYBMUJFWSA-N 0.000 description 1
- QAMOSDYDPIDUIP-MRXNPFEDSA-N NC[C@H](c1ccc2)OCCc1c2-c1ccccc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1ccccc1 QAMOSDYDPIDUIP-MRXNPFEDSA-N 0.000 description 1
- ITWNCCJEWGAJEU-GFCCVEGCSA-N NC[C@H](c1ccc2)OCCc1c2-c1cnc[s]1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1cnc[s]1 ITWNCCJEWGAJEU-GFCCVEGCSA-N 0.000 description 1
- OTHYENXSAUFRTA-CQSZACIVSA-N NC[C@H](c1ccc2)OCCc1c2-c1cnncc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1cnncc1 OTHYENXSAUFRTA-CQSZACIVSA-N 0.000 description 1
- HVCNDMFOCZUOPJ-CYBMUJFWSA-N NC[C@H](c1ccc2)OCCc1c2-c1n[o]cc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1n[o]cc1 HVCNDMFOCZUOPJ-CYBMUJFWSA-N 0.000 description 1
- XYRVATVHFMGOES-GFCCVEGCSA-N NC[C@H](c1ccc2)OCCc1c2-c1ncc[nH]1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1ncc[nH]1 XYRVATVHFMGOES-GFCCVEGCSA-N 0.000 description 1
- RKGIMVPUGKKTPK-CQSZACIVSA-N NC[C@H](c1ccc2)OCCc1c2-c1ncncc1 Chemical compound NC[C@H](c1ccc2)OCCc1c2-c1ncncc1 RKGIMVPUGKKTPK-CQSZACIVSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762540249P | 2017-08-02 | 2017-08-02 | |
| US62/540,249 | 2017-08-02 | ||
| PCT/US2018/044854 WO2019028165A1 (en) | 2017-08-02 | 2018-08-01 | ISOCHROMAN COMPOUNDS AND USES THEREOF |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020529419A JP2020529419A (ja) | 2020-10-08 |
| JP2020529419A5 true JP2020529419A5 (enExample) | 2021-09-09 |
| JP7191085B2 JP7191085B2 (ja) | 2022-12-16 |
Family
ID=63245089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020505414A Active JP7191085B2 (ja) | 2017-08-02 | 2018-08-01 | イソクロマン化合物およびその使用 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10780074B2 (enExample) |
| EP (1) | EP3661929B1 (enExample) |
| JP (1) | JP7191085B2 (enExample) |
| KR (1) | KR20200036008A (enExample) |
| CN (1) | CN111183138A (enExample) |
| AU (1) | AU2018312559B2 (enExample) |
| BR (1) | BR112020001433A2 (enExample) |
| CA (1) | CA3070993C (enExample) |
| EA (1) | EA202090414A1 (enExample) |
| IL (1) | IL272200A (enExample) |
| MX (1) | MX2020000523A (enExample) |
| SG (1) | SG11202000669VA (enExample) |
| WO (1) | WO2019028165A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2017301769B2 (en) | 2016-07-29 | 2022-07-28 | Pgi Drug Discovery Llc | Compounds and compositions and uses thereof |
| SG10202100751YA (en) | 2016-07-29 | 2021-03-30 | Sunovion Pharmaceuticals Inc | Compounds and compositions and uses thereof |
| SG11202000669VA (en) | 2017-08-02 | 2020-02-27 | Sunovion Pharmaceuticals Inc | Isochroman compounds and uses thereof |
| JP7703449B2 (ja) | 2019-03-14 | 2025-07-07 | スミトモ・ファーマ・アメリカ・インコーポレイテッド | イソクロマニル化合物の塩およびその結晶体、ならびにそれらの製造方法、治療用途および医薬組成物 |
| CN117177977A (zh) * | 2021-04-10 | 2023-12-05 | 住友制药株式会社 | 二环吡啶衍生物 |
| US12077546B2 (en) | 2021-04-10 | 2024-09-03 | Sumitomo Pharma Co., Ltd. | Bicyclic pyridine derivative |
| JP2024513500A (ja) * | 2021-04-10 | 2024-03-25 | サノビオン ファーマシューティカルズ インク | Ｔａａｒ１及びセロトニン調節剤、及び医薬組成物、並びにそれらの使用方法 |
| AU2022254568A1 (en) | 2021-04-10 | 2023-11-16 | Sumitomo Pharma Co., Ltd. | Bicyclic pyridine derivative |
| JP2025534292A (ja) * | 2022-09-26 | 2025-10-15 | ピージーアイ ドラッグ ディスカバリー エルエルシー | 中枢神経系疾患又は障害の治療のための化合物 |
Family Cites Families (218)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB984365A (en) | 1961-10-03 | 1965-02-24 | Ici Ltd | Pyrimidine derivatives |
| US3470179A (en) | 1966-06-14 | 1969-09-30 | Sandoz Ag | 4-substituted-3,4-dihydroquinazolines |
| US3549624A (en) | 1967-08-17 | 1970-12-22 | Pfizer & Co C | 2-substituted-2-delta**2-tetrahydropyrimidines and delta**2-im |
| US3438995A (en) | 1968-01-08 | 1969-04-15 | Melville Sahyun | Diazaheterocyclic substituted benz-oxaheterocyclic compounds |
| US3536809A (en) | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3551427A (en) | 1969-05-09 | 1970-12-29 | Sandoz Ag | 4-thienyl-2-(1h)-quinazolones |
| US4036842A (en) | 1972-05-16 | 1977-07-19 | American Home Products Corporation | Process for preparing polycyclic heterocycles having a pyran ring |
| US4021451A (en) | 1972-05-16 | 1977-05-03 | American Home Products Corporation | Process for preparing polycyclic heterocycles having a pyran ring |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US3995052A (en) | 1973-07-09 | 1976-11-30 | Ayerst Mckenna And Harrison Ltd. | Indenopyran- and indenothiopyranalkylamines III in the treatment of depression |
| US4041169A (en) | 1975-03-05 | 1977-08-09 | Ayerst Mckenna And Harrison Ltd. | Pharmaceutical method for using pyrano-and thiopyranoindole derivatives |
| US4021452A (en) | 1975-04-23 | 1977-05-03 | American Cyanamid Company | 2,5-Dihydro-2,5-dialkoxyfuran derivatives |
| JPS5919549B2 (ja) | 1976-01-01 | 1984-05-07 | 武田薬品工業株式会社 | 異節環状化合物 |
| US4008719A (en) | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| US4127665A (en) | 1978-01-18 | 1978-11-28 | Pfizer Inc. | Thienohydantoin derivatives |
| US4556656A (en) | 1978-10-23 | 1985-12-03 | The Upjohn Company | 2-Benzoxepins |
| FR2459239A1 (fr) | 1979-06-20 | 1981-01-09 | Logeais Labor Jacques | Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique |
| US4500543A (en) * | 1982-06-01 | 1985-02-19 | Abbott Laboratories | Substituted 1-aminomethyl-phthalans |
| IE58110B1 (en) | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| PH30676A (en) | 1986-07-22 | 1997-09-16 | Boehringer Ingelhein Kg | Hetrazepine compounds which have useful pharmaceutical utility |
| JPH049367Y2 (enExample) | 1986-12-27 | 1992-03-09 | ||
| JPS646267A (en) | 1987-02-04 | 1989-01-10 | Daiichi Seiyaku Co | 2-benzopyran derivative |
| EP0305332A3 (de) | 1987-08-26 | 1990-04-04 | Ciba-Geigy Ag | Imidazol-Derivate |
| PT90001B (pt) | 1988-03-16 | 1994-06-30 | Zambeletti Spa L | Processo para a preparacao de derivados heterociclicos de etilenodiamina |
| US5073543A (en) | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
| DE3827727A1 (de) | 1988-08-16 | 1990-02-22 | Boehringer Ingelheim Kg | Anellierte tetrahydropyridinessigsaeurederivate, verfahren zu deren herstellung und verwendung solcher verbindungen zur kardioprotektion |
| GB8824400D0 (en) | 1988-10-18 | 1988-11-23 | Glaxo Group Ltd | Chemical compounds |
| EP0368175A1 (de) | 1988-11-06 | 1990-05-16 | Boehringer Ingelheim Kg | 3S,7S-3-(Morpholinocarbonyl)-5-(2-chlorphenyl)-7,10-dimethyl-3,4-dihydro-2H,7H-cyclopenta[4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin. |
| GB8827479D0 (en) | 1988-11-24 | 1988-12-29 | Zambeletti Spa L | Novel compounds |
| IT1229203B (it) | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
| US5621133A (en) | 1989-05-31 | 1997-04-15 | Deninno; Michael P. | Dopamine agonists |
| US4994486A (en) | 1989-05-31 | 1991-02-19 | Abbott Laboratories | Dopaminergic compounds |
| US4963568A (en) | 1989-05-31 | 1990-10-16 | Abbott Laboratories | Dopamine agonists |
| EP0416740A3 (en) | 1989-08-08 | 1991-08-28 | Beecham Group P.L.C. | Novel compounds with renin-inhibiting activity |
| JPH0735373B2 (ja) | 1989-08-11 | 1995-04-19 | 三共株式会社 | カルボン酸アミド化合物 |
| US5120548A (en) | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
| GB8926560D0 (en) | 1989-11-24 | 1990-01-17 | Zambeletti Spa L | Pharmaceuticals |
| DE3940477A1 (de) | 1989-12-07 | 1991-06-13 | Bayer Ag | Hetaryl-substituierte pyridinylpyrimidin-derivate |
| US5032598A (en) | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
| GB8927872D0 (en) | 1989-12-08 | 1990-02-14 | Beecham Group Plc | Pharmaceuticals |
| US5420151A (en) | 1989-12-22 | 1995-05-30 | Aktiebolaget Astra | Chroman derivatives |
| JPH03223277A (ja) | 1989-12-29 | 1991-10-02 | Yoshitomi Pharmaceut Ind Ltd | ベンゾチオフェン誘導体 |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| ZA912744B (en) | 1990-03-23 | 1992-02-26 | Zambeletti Spa L | Pharmaceuticals |
| US5733566A (en) | 1990-05-15 | 1998-03-31 | Alkermes Controlled Therapeutics Inc. Ii | Controlled release of antiparasitic agents in animals |
| US5238939A (en) | 1990-05-25 | 1993-08-24 | Akzo N.V. | Isochromane derivatives |
| GB9018139D0 (en) | 1990-08-17 | 1990-10-03 | Pfizer Ltd | Therapeutic agents |
| NZ240155A (en) | 1990-10-29 | 1992-10-28 | Ishihara Sangyo Kaisha | Heterocyclyl acyl and (hexahydro) indanyl acyl substituted hydrazine derivatives, preparation thereof and pesticidal compositions |
| DE4104257A1 (de) | 1991-02-13 | 1992-08-20 | Boehringer Ingelheim Kg | Verwendung von anellierten tetrahydropyridinessigsaeurederivaten fuer die behandlung neurologischer erkrankungen |
| GB9104839D0 (en) | 1991-03-07 | 1991-04-17 | Zambeletti Spa L | Novel compounds |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| HRP920935A2 (en) | 1991-10-08 | 1995-08-31 | Astra Ab | New therapeutically active compound |
| US5288749A (en) | 1991-12-20 | 1994-02-22 | Abbott Laboratories | Tertiary and secondary amines as alpha-2 antagonists and serotonin uptake inhibitors |
| US5580578A (en) | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| PH31294A (en) | 1992-02-13 | 1998-07-06 | Thomae Gmbh Dr K | Benzimidazolyl derivatives, pharmaceutical compositions containing these compounds and process for preparing them. |
| JP3223277B2 (ja) | 1992-04-10 | 2001-10-29 | カシオ計算機株式会社 | 楽音制御装置 |
| FR2692264B1 (fr) | 1992-06-12 | 1994-08-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| IT1255178B (it) | 1992-06-26 | 1995-10-20 | Pierrel Spa | N(eter0)-aril-n(etero)-tetralinalchil piperazine aventi attivita' serotoninergica,dopaminergica e adrenergica |
| DE59308842D1 (de) | 1992-12-02 | 1998-09-10 | Ciba Geigy Ag | Selektiv-herbizides Mittel |
| US5591767A (en) | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| TW334423B (en) | 1993-10-22 | 1998-06-21 | Hoffmann La Roche | Tricyclic 1-aminoethylpyrrole-derivatives |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| FR2723091B1 (fr) | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
| WO1996038435A1 (en) * | 1995-05-30 | 1996-12-05 | Abbott Laboratories | Dopamine agonists |
| FR2734819B1 (fr) | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant |
| SE9702563D0 (sv) | 1997-07-02 | 1997-07-02 | Astra Ab | Compounds |
| DE19751949A1 (de) * | 1997-11-24 | 1999-05-27 | Bayer Ag | Verwendung von substituierten Aminomethyl-Chromanen zur Verhinderung der neuronalen Degeneration und zur Förderung der neuronalen Regeneration |
| WO1999046267A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| WO1999046237A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases |
| US6262044B1 (en) | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
| AU2713599A (en) | 1998-03-12 | 1999-09-27 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| DE19817262A1 (de) | 1998-04-18 | 1999-10-21 | Bayer Ag | Neue 2-heterocyclisch substituierte Dihydropyrimidine |
| DE19817265A1 (de) | 1998-04-18 | 1999-10-21 | Bayer Ag | Verwendung von Dihydropyrimidinen als Arzneimittel und neue Stoffe |
| WO2000000487A1 (en) | 1998-06-30 | 2000-01-06 | Eli Lilly And Company | 5-ht1f agonists |
| AU6325599A (en) | 1998-10-21 | 2000-05-08 | Dr. Reddy's Research Foundation | New compounds, their preparation and use |
| CA2354875A1 (en) | 1998-12-14 | 2000-06-22 | Fujisawa Pharmaceutical Co., Ltd. | Piperazine derivatives |
| EP1147113B1 (en) | 1999-01-19 | 2006-06-07 | Neurosearch A/S | Fused heterocyclic compounds and their use in the treatment of neurodegenerative diseases |
| US6313309B1 (en) | 1999-04-05 | 2001-11-06 | Ortho-Mcneil Pharmaceutical, Inc. | 4-thionaphthyl—1H—imidazoles which are usefulα22-adrenoceptoR agonists/ antagonists |
| AU4589800A (en) | 1999-05-05 | 2000-11-21 | Darwin Discovery Limited | 9-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,9-dihydropurin-6-one derivatives as pde7inhibitors |
| GB9914025D0 (en) | 1999-06-17 | 1999-08-18 | Zeneca Ltd | Chemical compounds |
| WO2001017516A2 (en) | 1999-09-10 | 2001-03-15 | Novo Nordisk A/S | Method of inhibiting protein tyrosine phosphatase 1b and/or t-cell protein tyrosine phosphatase and/or other ptpases with an asp residue at position 48 |
| WO2001019831A1 (en) | 1999-09-10 | 2001-03-22 | Novo Nordisk A/S | MODULATORS OF PROTEIN TYROSINE PHOSPHATASES (PTPases) |
| WO2001032610A1 (en) | 1999-10-29 | 2001-05-10 | Kaken Pharmaceutical Co., Ltd. | Urea derivative, process for producing the same, and medicine containing the urea derivative |
| AR030537A1 (es) | 1999-11-05 | 2003-08-27 | Abbott Lab | Acidos quinolincarboxilicos y naftiridincarboxilico antibacterianos |
| KR100521735B1 (ko) | 2000-02-25 | 2005-10-17 | 에프. 호프만-라 로슈 아게 | 아데노신 수용체 조절인자 |
| HUP0300382A3 (en) | 2000-03-29 | 2006-11-28 | Cyclacel Ltd | 2-substituted 4-heteroaryl-pyrimidines and their use in the treatmetn of proliferative disorders and pharmaceutical compositions containing the compounds |
| IL152023A0 (en) | 2000-04-26 | 2003-04-10 | Eisai Co Ltd | Compounds having adenosine a2 receptor antagonism and pharmaceutical compositions containing the same |
| US7112594B2 (en) | 2000-08-09 | 2006-09-26 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| WO2002022614A1 (en) | 2000-09-12 | 2002-03-21 | Sankyo Company,Limited | Quinolizine derivatives |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002066443A2 (en) | 2001-02-21 | 2002-08-29 | Ono Pharmaceutical Co., Ltd. | 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives |
| WO2002083667A2 (en) | 2001-04-13 | 2002-10-24 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| WO2002102387A1 (en) | 2001-06-18 | 2002-12-27 | H. Lundbeck A/S | Treatment of neuropathic pain |
| EP1409476B1 (en) | 2001-07-11 | 2004-12-15 | Eli Lilly And Company | Pharmaceutical compounds with serotonin receptor activity |
| DE60202296D1 (de) | 2001-07-11 | 2005-01-20 | Lilly Co Eli | Pharmazeutische verbindungen mit serotonin rezeptor aktivität |
| MXPA04003954A (es) | 2001-10-26 | 2004-11-29 | Aventis Pharma Inc | Bencimidazoles. |
| JP2003261566A (ja) | 2002-03-11 | 2003-09-19 | Sankyo Co Ltd | キノリジンを含有する医薬 |
| DE60325956D1 (de) | 2002-04-10 | 2009-03-12 | Dongbu Hitek Co Ltd | Benzopyranderivate, die mit sekundären aminen einschliesslich tetrazol substituiert sind, verfahren etzungen, die diese enthalten |
| TW200930291A (en) | 2002-04-29 | 2009-07-16 | Bayer Cropscience Ag | Pesticidal heterocycles |
| US7276522B2 (en) | 2002-05-21 | 2007-10-02 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones, 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| US7323485B2 (en) | 2002-05-21 | 2008-01-29 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| US7091232B2 (en) | 2002-05-21 | 2006-08-15 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| US7358269B2 (en) | 2002-05-21 | 2008-04-15 | Allergan, Inc. | 2-((2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)methyl)-3,4-dihydronapthalen-1(2H)-one |
| SE0202134D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Therapeutic agents |
| US20050113450A1 (en) | 2002-08-23 | 2005-05-26 | Atli Thorarensen | Antibacterial agents |
| UY27967A1 (es) | 2002-09-10 | 2004-05-31 | Pfizer | Acetil 2-hindroxi-1,3-diaminoalcanos |
| CN100384824C (zh) | 2002-09-10 | 2008-04-30 | 艾伦药物公司 | 乙酰基2-羟基-1,3-二氨基烷烃 |
| CA2502541A1 (en) | 2002-10-16 | 2004-04-29 | Isis Innovation Limited | Asparaginyl hydroxylases and modulators thereof |
| GB0224316D0 (en) | 2002-10-18 | 2002-11-27 | Syngenta Participations Ag | Chemical compounds |
| EP1587482A4 (en) | 2003-01-31 | 2010-08-25 | Technion Res & Dev Foundation | INFLAMMATORY COMPOSITIONS AND ITS USES |
| TWI422583B (zh) | 2003-03-07 | 2014-01-11 | 參天製藥股份有限公司 | 具有以４-吡啶烷硫基為取代基之新穎化合物 |
| JP2004269449A (ja) | 2003-03-11 | 2004-09-30 | Ishihara Sangyo Kaisha Ltd | ベンズアミド誘導体、それらの製造方法及びそれらを含有する有害生物防除剤 |
| WO2004080476A1 (en) | 2003-03-12 | 2004-09-23 | University Of North Carolina At Chapel Hill | Use of secretin in the treatment of schizophrenia |
| US7205318B2 (en) | 2003-03-18 | 2007-04-17 | Bristol-Myers Squibb Company | Lactam-containing cyclic diamines and derivatives as a factor Xa inhibitors |
| CN100475793C (zh) | 2003-03-31 | 2009-04-08 | 大正制药株式会社 | 喹唑啉衍生物及其制备药物的用途 |
| JP4516064B2 (ja) | 2003-04-04 | 2010-08-04 | ノバルティス アーゲー | 気道疾患の処置のためのキノリン−２−オン誘導体 |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| WO2004112719A2 (en) | 2003-06-19 | 2004-12-29 | Smithkline Beecham Corporation | Chemical compounds |
| US20050032873A1 (en) | 2003-07-30 | 2005-02-10 | Wyeth | 3-Amino chroman and 2-amino tetralin derivatives |
| CN1860112A (zh) | 2003-07-30 | 2006-11-08 | 惠氏公司 | 3－氨基苯并二氢吡喃和2－氨基四氢化萘衍生物 |
| DE10347385A1 (de) | 2003-10-08 | 2005-05-12 | Schering Ag | Umgelagerte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
| JP2005145859A (ja) | 2003-11-13 | 2005-06-09 | Nippon Steel Chem Co Ltd | 脱水素化方法及び芳香族複素環化合物の製造方法 |
| DE10360793A1 (de) | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| EP1715855A4 (en) | 2004-01-29 | 2010-06-16 | Elixir Pharmaceuticals Inc | ANTIVIRAL DRUGS |
| DE102004004974A1 (de) | 2004-01-31 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Thieno-Iminosäure-Derivate als Inhibitoren von Matrix-Metalloproteinasen |
| GB0403155D0 (en) | 2004-02-12 | 2004-03-17 | Vernalis Res Ltd | Chemical compounds |
| JP2007528403A (ja) | 2004-03-09 | 2007-10-11 | エラン ファーマシューティカルズ，インコーポレイテッド | 二環式アスパラギン酸プロテアーゼ阻害薬を用いるアミロイドーシスの処置方法 |
| KR100553398B1 (ko) | 2004-03-12 | 2006-02-16 | 한미약품 주식회사 | 티에노[3,2-ｃ]피리딘 유도체의 제조 방법 및 이에사용되는 중간체 |
| WO2005095326A2 (en) | 2004-03-25 | 2005-10-13 | Elan Pharmaceuticals, Inc. | 2-amino- and 2-thio-substituted 1,3-diaminopropanes |
| DK1749001T3 (da) * | 2004-04-29 | 2010-06-28 | Aventis Pharma Inc | 3-piperidinylisochroman-5-ol som dopaminagonister |
| KR20070046150A (ko) | 2004-07-28 | 2007-05-02 | 아이알엠 엘엘씨 | 스테로이드 호르몬 핵 수용체의 조절제로서의 화합물 및조성물 |
| SE0401970D0 (sv) | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Novel compounds |
| SE0401971D0 (sv) | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Piperidne derivatives |
| EP1634873A1 (en) | 2004-08-27 | 2006-03-15 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
| FR2875230A1 (fr) | 2004-09-13 | 2006-03-17 | Sanofi Aventis Sa | Derives de pyrazole condense, leur preparation et leur application en therapeutique |
| JP2006117568A (ja) | 2004-10-20 | 2006-05-11 | Mitsubishi Pharma Corp | チオフェン環を有する新規アミド誘導体及びその医薬としての用途 |
| WO2006053274A2 (en) | 2004-11-15 | 2006-05-18 | Bristol-Myers Squibb Company | 2-amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| WO2006066172A1 (en) | 2004-12-17 | 2006-06-22 | Amgen, Inc. | Aminopyrimidine compounds and methods of use |
| DE102004063227A1 (de) | 2004-12-22 | 2006-07-06 | Schering Ag | Tricylische Aminoalkohole, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
| AU2006214233A1 (en) | 2005-02-17 | 2006-08-24 | Wyeth | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| US7884109B2 (en) | 2005-04-05 | 2011-02-08 | Wyeth Llc | Purine and imidazopyridine derivatives for immunosuppression |
| BRPI0610027A2 (pt) | 2005-04-22 | 2010-05-18 | Wyeth Corp | derivados de cromano e cromeno e usos dos mesmos |
| EP1873153B1 (en) | 2005-04-22 | 2010-07-07 | Daiichi Sankyo Company, Limited | 3-azetidinecarboxylic acid derivatives for use as immunosuppressants |
| DE602006010540D1 (de) | 2005-05-04 | 2009-12-31 | Hoffmann La Roche | (3,4-dihydro-chinazolin-2-yl)-(2-aryloxy-ethyl)-amine mit aktivität am 5-ht-rezeptor |
| WO2007001939A1 (en) | 2005-06-27 | 2007-01-04 | Janssen Pharmaceutica N.V. | Tetrahydro-pyranopyrazole compounds displaying cannabinoid modulating activities |
| WO2007002681A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
| JP2009505948A (ja) | 2005-07-11 | 2009-02-12 | デブジェン エヌブイ | キナーゼ阻害剤としてのアミド誘導体 |
| US7598255B2 (en) | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| TW200800201A (en) | 2005-11-18 | 2008-01-01 | Lilly Co Eli | Pyrimidinyl benzothiophene compounds |
| US7745484B2 (en) | 2005-11-21 | 2010-06-29 | Amgen Inc. | Beta-secretase modulators and methods of use |
| WO2007095586A2 (en) | 2006-02-14 | 2007-08-23 | The Trustees Of Columbia University In The City Of New York | Neuronal pain pathway modulators |
| WO2007102999A2 (en) | 2006-02-21 | 2007-09-13 | Ampla Pharmaceuticals Inc. | Cb1 antagonists and inverse agonists |
| EP1829869A1 (en) | 2006-03-02 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | 4,5,6,7-Tetrahydrobenzo[b]thiophene derivatives and their use as sigma receptor ligands |
| CN101421280A (zh) | 2006-04-12 | 2009-04-29 | 惠氏公司 | 作为5-羟色胺-6配体的经取代二氢[1,4]噁嗪并[2.3.4-hi]吲唑衍生物 |
| JPWO2007126041A1 (ja) | 2006-04-28 | 2009-09-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ベンゾイソオキサゾール化合物 |
| WO2008011557A2 (en) | 2006-07-20 | 2008-01-24 | Borchardt Allen J | Heteroaryl inhibitors of rho kinase |
| CA2667082A1 (en) | 2006-10-04 | 2008-04-10 | Schering Corporation | Bicyclic and tricyclic derivatives as thrombin receptor antagonists |
| US7960569B2 (en) | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| WO2008058342A1 (en) | 2006-11-15 | 2008-05-22 | Genetic Technologies Limited | Compounds, compositions and methods for controlling invertebrate pests |
| WO2009008906A2 (en) | 2007-02-06 | 2009-01-15 | The Trustees Of The University Of Pennsylvania | Therapeutic compounds for blocking dna synthesis of pox viruses |
| CA2678180A1 (en) | 2007-02-13 | 2008-12-04 | Northeastern University | Methods and compositions for improving immune responses |
| US8012986B2 (en) | 2007-04-02 | 2011-09-06 | Hoffmann-La Roche Inc. | Pyridine and pyrimidine derivatives as MGLUR2 antagonists |
| US7598417B2 (en) | 2007-04-12 | 2009-10-06 | Allergan, Inc. | Substituted fluoroethyl ureas as alpha 2 adrenergic agents |
| EP1982714A1 (en) | 2007-04-16 | 2008-10-22 | Laboratorios del Dr. Esteve S.A. | Pyrano-pyrazole-amines |
| EP1982987A1 (en) | 2007-04-16 | 2008-10-22 | Laboratorios del Dr. Esteve S.A. | Spiro-pyrano-pyrazole derivatives |
| EP2002834A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryl/Hetarylamide als Modulatoren des EP2-Rezeptors |
| EP2020414A1 (en) | 2007-06-20 | 2009-02-04 | Laboratorios del Dr. Esteve S.A. | spiro[piperidine-4,4'-thieno[3,2-c]pyran] derivatives and related compounds as inhibitors of the sigma receptor for the treatment of psychosis |
| US8338623B2 (en) | 2007-07-09 | 2012-12-25 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| US8022209B2 (en) | 2007-09-12 | 2011-09-20 | Janssen Pharmaceutica Nv | Substituted nitrogen-containing heteroaryl derivatives useful as modulators of the histamine H4 receptor |
| KR101103118B1 (ko) | 2007-11-02 | 2012-01-04 | 동아제약주식회사 | 신규한 1,3-디히드로-5-이소벤조퓨란카르보니트릴 유도체 화합물 및 이를 함유하는 조루증 치료용 약학조성물 |
| US8158792B2 (en) | 2007-11-21 | 2012-04-17 | Janssen Pharmaceutica N.V. | Spiropiperidines for use as tryptase inhibitors |
| US7973051B2 (en) | 2007-11-30 | 2011-07-05 | Hoffman-La Roche Inc. | Aminothiazoles as FBPase inhibitors for diabetes |
| EP2230230A4 (en) | 2007-12-07 | 2011-03-16 | Nissan Chemical Ind Ltd | SUBSTITUTED DIHYDROAZOL COMPOUND AND PESTICIDES |
| CN101468986B (zh) | 2007-12-26 | 2010-12-29 | 香港南北兄弟国际投资有限公司 | 一种二氢嘧啶消旋化合物的拆分方法 |
| CN101468987B (zh) | 2007-12-26 | 2011-06-08 | 香港南北兄弟国际投资有限公司 | 2-杂环取代的二氢嘧啶消旋化合物的拆分方法 |
| WO2009085256A1 (en) | 2007-12-27 | 2009-07-09 | Panacos Pharmaceuticals, Inc. | Anti-hiv compounds |
| EP2149552A1 (de) * | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma AG | 5,6 substituierte Benzamid-Derivate als Modulatoren des EP2-Rezeptors |
| CN101759710B (zh) | 2008-10-06 | 2011-10-05 | 山东轩竹医药科技有限公司 | 含有取代的氮杂环的头孢菌素衍生物 |
| WO2010053583A2 (en) | 2008-11-10 | 2010-05-14 | Dana Farber Cancer Institute | Small molecule cd4 mimetics and uses thereof |
| CA2750935A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| WO2010093425A1 (en) | 2009-02-11 | 2010-08-19 | Sepracor Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| TW201117812A (en) | 2009-08-05 | 2011-06-01 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
| WO2011036889A1 (ja) | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| KR101368130B1 (ko) | 2009-11-16 | 2014-02-27 | 일라이 릴리 앤드 캄파니 | Ｏｒｌ―１ 수용체 길항제로서의 스피로피페리딘 화합물 |
| UA107943C2 (xx) | 2009-11-16 | 2015-03-10 | Lilly Co Eli | Сполуки спіропіперидину як антагоністи рецептора orl-1 |
| WO2011068171A1 (ja) | 2009-12-03 | 2011-06-09 | 第一三共株式会社 | 二環性含窒素飽和へテロ環誘導体 |
| CA2781716A1 (en) | 2009-12-04 | 2011-06-09 | Sunovion Pharmaceuticals Inc. | Multicyclic thieno compounds and use thereof for the treatment of a neurological disorder |
| PL2520575T3 (pl) | 2009-12-28 | 2017-05-31 | General Incorporated Association Pharma Valley Project Supporting Organization | Związek 1,3,4-oksadiazolo-2-karboksyamidowy |
| WO2011094740A2 (en) | 2010-02-01 | 2011-08-04 | Sgl Carbon Se | Defensive, ceramic based, applioue armor, device for providing anti-projectile armoring protection and process for producing ceramic based projectile armor with hollow geometry |
| EP2377850A1 (en) | 2010-03-30 | 2011-10-19 | Pharmeste S.r.l. | TRPV1 vanilloid receptor antagonists with a bicyclic portion |
| US8895608B2 (en) | 2010-04-23 | 2014-11-25 | Kineta, Inc. | Sulfonamide anti-viral compounds |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CA2820078C (en) | 2010-12-16 | 2019-02-12 | F. Hoffmann-La Roche Ag | Tricyclic pi3k inhibitor compounds and methods of use |
| JP5715713B2 (ja) | 2011-03-10 | 2015-05-13 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 可溶性グアニル酸シクラーゼ活性化因子 |
| CN102731574B (zh) | 2011-03-30 | 2016-03-02 | 中国人民解放军军事医学科学院毒物药物研究所 | 噻吩并吡啶类α-胺基苄基膦酸酯、其制备方法及用途 |
| WO2013010453A1 (en) | 2011-07-15 | 2013-01-24 | Abbott Laboratories | Chemoking receptor antagonists |
| BR112014007851A2 (pt) | 2011-10-05 | 2017-04-18 | Hoffmann La Roche | ciclo-hexil-4h,6h-oxa-2,3,10b-triaza-benzo[e]azulenos como antagonistas de v1a |
| US9365588B2 (en) | 2011-11-04 | 2016-06-14 | Vertex Pharmaceuticals Incorporated | Benzoxazines as modulators of ion channels |
| AU2012357169B2 (en) | 2011-12-22 | 2017-03-30 | Merck Patent Gmbh | Tetraaza-cyclopenta[a]indenyl and their use as positive allosteric modulators |
| US10189825B2 (en) | 2012-02-08 | 2019-01-29 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| MX2014014911A (es) | 2012-06-20 | 2015-05-15 | Univ Vanderbilt | Análogos de alcoxi pirazol bicíclico sustituido como moduladores alostéricos de receptores de mglur5. |
| EP2920166B1 (en) | 2012-11-13 | 2016-11-02 | Array Biopharma, Inc. | Bicyclic urea, thiourea, guanidine and cyanoguanidine compounds useful for the treatment of pain |
| WO2014106238A1 (en) | 2012-12-31 | 2014-07-03 | Fang, Qun, Kevin | Heterocyclic compounds and methods of use thereof |
| JP2014214130A (ja) | 2013-04-26 | 2014-11-17 | 大正製薬株式会社 | ジヒドロイミダゾオキサゾール誘導体を含有する医薬 |
| EA201791804A1 (ru) | 2015-02-11 | 2018-02-28 | Суновион Фармасьютикалз Инк. | Соединения 1-гетероциклил изохроманила и аналоги для лечения расстройств цнс |
| CA2976092A1 (en) | 2015-02-11 | 2016-08-18 | Sunovion Pharmaceuticals Inc. | Fused dihydro-4h-pyrazolo[5,1-c][1,4]oxazinyl compounds and analogs for treating cns disorders |
| AU2017301769B2 (en) * | 2016-07-29 | 2022-07-28 | Pgi Drug Discovery Llc | Compounds and compositions and uses thereof |
| SG10202100751YA (en) | 2016-07-29 | 2021-03-30 | Sunovion Pharmaceuticals Inc | Compounds and compositions and uses thereof |
| AU2018220509B2 (en) | 2017-02-16 | 2022-04-28 | Sumitomo Pharma America, Inc. | Methods of treating schizophrenia |
| SG11202000669VA (en) | 2017-08-02 | 2020-02-27 | Sunovion Pharmaceuticals Inc | Isochroman compounds and uses thereof |
| CA3091292A1 (en) | 2018-02-16 | 2019-08-22 | Sunovion Pharmaceuticals Inc. | Salts, crystal forms, and production methods thereof |
| US20210008030A1 (en) | 2018-02-16 | 2021-01-14 | Sunovion Pharmaceuticals Inc. | Methods of treating social function disorders |
| JP2022511509A (ja) | 2018-12-06 | 2022-01-31 | サノビオン ファーマシューティカルズ インク | 神経障害および神経障害の処置方法 |
-
2018
- 2018-08-01 SG SG11202000669VA patent/SG11202000669VA/en unknown
- 2018-08-01 CA CA3070993A patent/CA3070993C/en active Active
- 2018-08-01 EA EA202090414A patent/EA202090414A1/ru unknown
- 2018-08-01 EP EP18756100.6A patent/EP3661929B1/en active Active
- 2018-08-01 AU AU2018312559A patent/AU2018312559B2/en not_active Ceased
- 2018-08-01 US US16/051,863 patent/US10780074B2/en active Active
- 2018-08-01 MX MX2020000523A patent/MX2020000523A/es unknown
- 2018-08-01 CN CN201880047336.XA patent/CN111183138A/zh active Pending
- 2018-08-01 JP JP2020505414A patent/JP7191085B2/ja active Active
- 2018-08-01 KR KR1020207006086A patent/KR20200036008A/ko not_active Withdrawn
- 2018-08-01 WO PCT/US2018/044854 patent/WO2019028165A1/en not_active Ceased
- 2018-08-01 BR BR112020001433-8A patent/BR112020001433A2/pt not_active Application Discontinuation
-
2020
- 2020-01-23 IL IL272200A patent/IL272200A/en unknown
- 2020-08-12 US US16/991,771 patent/US11491133B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020529419A5 (enExample) | ||
| JP7261264B2 (ja) | 新規化合物 | |
| US11197867B2 (en) | Aminopyrimidinyl compounds | |
| JP5864589B2 (ja) | 細菌トポイソメラーゼｉｉ阻害性２−エチルカルバモイルアミノ−１，３−ベンゾチアゾール−５−イル類 | |
| AU2018201953A1 (en) | Certain amino-pyridazines, compositions thereof, and methods of their use | |
| JP2021526551A (ja) | キナーゼ阻害剤としてのヘテロ環式化合物、ヘテロ環式化合物を含む組成物、及びそれらを使用する方法 | |
| JP2016514124A (ja) | 変異ｉｄｈの阻害薬としての３−ピリミジン−４−イル−オキサゾリジン−２−オン | |
| JP2011520896A5 (enExample) | ||
| JP2016523911A5 (enExample) | ||
| KR20170020522A (ko) | 인돌린-2-온 또는 피롤로-피리딘-2-온 유도체 | |
| JP2020502230A5 (enExample) | ||
| JP2019537581A5 (enExample) | ||
| JPWO2020239953A5 (enExample) | ||
| RU2013142924A (ru) | Вещества, ингибирующие переносчик глицина | |
| HK1240929B (zh) | 新化合物 | |
| HK1240929A1 (en) | Novel compounds | |
| BR112017005887B1 (pt) | Composto, método para produção e uso do mesmo, bem como composição farmacêutica | |
| HK1241857B (zh) | 作为jak抑制剂的氨基嘧啶基化合物 | |
| OA18225A (en) | Aminopyrimidinyl compounds as Jak inhibitors. |