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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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 |
| DE68923891T2 (de) | 1988-03-16 | 1996-02-22 | Smithkline Beecham Farm | Heterocyclische Derivate. |
| 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. |
| US4963568A (en) | 1989-05-31 | 1990-10-16 | Abbott Laboratories | Dopamine agonists |
| US4994486A (en) * | 1989-05-31 | 1991-02-19 | Abbott Laboratories | Dopaminergic compounds |
| US5621133A (en) | 1989-05-31 | 1997-04-15 | Deninno; Michael P. | 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) |
| US6262044B1 (en) | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
| CN1300291A (zh) | 1998-03-12 | 2001-06-20 | 诺沃挪第克公司 | 蛋白质酪氨酸磷酸酶(ptp酶)的调节物 |
| EP1080068A1 (en) | 1998-03-12 | 2001-03-07 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases |
| 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 |
| ATE252572T1 (de) | 1998-06-30 | 2003-11-15 | Lilly Co Eli | 5-ht1f agonisten |
| EP1123292A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| KR20010086104A (ko) | 1998-12-14 | 2001-09-07 | 후지야마 아키라 | 피페라진 유도체 |
| DE60028538T2 (de) | 1999-01-19 | 2007-06-21 | Neurosearch A/S | Kondensierte heterocyclische verbindungen und ihre verwendung zur behandlung von neurodegenerativen erkrankungen |
| 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 |
| AU7476800A (en) | 1999-09-10 | 2001-04-10 | 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 |
| ATE309250T1 (de) | 1999-09-10 | 2005-11-15 | Novo Nordisk As | Modulatoren der protein tyrosin phosphatase (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 |
| EP1261327B1 (en) | 2000-02-25 | 2005-04-27 | F.Hoffmann-La Roche Ag | Adenosine receptor modulators |
| IL151946A0 (en) | 2000-03-29 | 2003-04-10 | Cyclacel Ltd | 2-substituted 4-heteroaryl-pyrimidines and their use in the treatment of proliferative disorders |
| WO2001080893A1 (en) | 2000-04-26 | 2001-11-01 | Eisai Co., Ltd. | Medicinal compositions promoting bowel movement |
| AU2001277731A1 (en) | 2000-08-09 | 2002-02-18 | Welfide Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| AU2001286191A1 (en) | 2000-09-12 | 2002-03-26 | 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 |
| DE60214701T2 (de) | 2001-04-13 | 2007-09-13 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von c-jun-n-terminalen-kinasen (jnk) und anderen proteinkinasen |
| WO2002102387A1 (en) | 2001-06-18 | 2002-12-27 | H. Lundbeck A/S | Treatment of neuropathic pain |
| WO2003006455A1 (en) | 2001-07-11 | 2003-01-23 | 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 |
| JP4237639B2 (ja) | 2002-04-10 | 2009-03-11 | ドンブ ハンノン ケミカル カンパニー リミテッド | テトラゾールを含む二次アミンで置換されたベンゾピラン誘導体、その製造方法及びそれを含む製薬組成物 |
| TW200306783A (en) | 2002-04-29 | 2003-12-01 | Fmc Corp | Pesticidal heterocycles |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| MXPA05004033A (es) | 2002-10-16 | 2005-06-08 | Isis Innovation | Hidroxilasas de asparaginil y moduladores de las mismas. |
| GB0224316D0 (en) | 2002-10-18 | 2002-11-27 | Syngenta Participations Ag | Chemical compounds |
| WO2004066912A2 (en) | 2003-01-31 | 2004-08-12 | Technion Research & Development Foundation Ltd. | Anti-inflammatory compositions and uses thereof |
| EP2527326B1 (en) | 2003-03-07 | 2014-10-08 | Santen Pharmaceutical Co., Ltd | Novel compounds having 4-pyridylalkylthio group as substituent |
| 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 |
| WO2004087142A1 (en) | 2003-04-04 | 2004-10-14 | Novartis Ag | Quinoline-2-one-derivatives for the treatment of airways diseases |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| EP1633740B1 (en) | 2003-06-19 | 2011-11-09 | GlaxoSmithKline LLC | 5-(acylamino)indazole derivatives as kinase inhibitors |
| 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 |
| US20050032873A1 (en) | 2003-07-30 | 2005-02-10 | Wyeth | 3-Amino chroman and 2-amino tetralin derivatives |
| 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 |
| AU2005208938A1 (en) | 2004-01-29 | 2005-08-11 | Elixir Pharmaceuticals, Inc | Anti-viral therapeutics |
| 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 |
| US20050239832A1 (en) | 2004-03-09 | 2005-10-27 | Varghese John | Methods of treatment of amyloidosis using bi-cyclic aspartyl protease inhibitors |
| KR100553398B1 (ko) | 2004-03-12 | 2006-02-16 | 한미약품 주식회사 | 티에노[3,2-ｃ]피리딘 유도체의 제조 방법 및 이에사용되는 중간체 |
| BRPI0509186A (pt) | 2004-03-25 | 2007-08-28 | Elan Pharm Inc | 1,3-diaminopropanos 2-amino-e 2-tio-substituìdos |
| JP4685861B2 (ja) * | 2004-04-29 | 2011-05-18 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | ドーパミンアゴニストとしての３−ピペリジニルイソクロマン−５−オール |
| AU2005267798A1 (en) | 2004-07-28 | 2006-02-09 | Irm Llc | Compounds and compositions as modulators of steroid hormone nuclear receptors |
| 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 |
| AU2005316312B2 (en) | 2004-12-17 | 2009-10-22 | 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 |
| TW200640931A (en) | 2005-02-17 | 2006-12-01 | Wyeth Corp | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| US7884109B2 (en) | 2005-04-05 | 2011-02-08 | Wyeth Llc | Purine and imidazopyridine derivatives for immunosuppression |
| CA2605594A1 (en) | 2005-04-22 | 2006-11-02 | Daiichi Sankyo Company, Limited | Heterocyclic compound |
| TW200716595A (en) | 2005-04-22 | 2007-05-01 | Wyeth Corp | Chromane and chromene derivatives and uses thereof |
| AU2006243244A1 (en) | 2005-05-04 | 2006-11-09 | F. Hoffmann-La Roche Ag | (3,4-dihydro-quinazolin-2-yl)-(2-aryloxy-ethyl)-amines having an activity on the 5-HT receptor |
| WO2007001939A1 (en) | 2005-06-27 | 2007-01-04 | Janssen Pharmaceutica N.V. | Tetrahydro-pyranopyrazole compounds displaying cannabinoid modulating activities |
| KR20080030630A (ko) | 2005-06-27 | 2008-04-04 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기 전도성 중합체 조성물 |
| BRPI0615524A2 (pt) | 2005-07-11 | 2010-04-06 | Devgen Nv | derivados da amida como inibidores da quinase |
| 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 |
| JP2009528999A (ja) | 2006-02-21 | 2009-08-13 | アンプラ ファーマシューティカルズ インコーポレイテッド | Ｃｂ１アンタゴニストおよび逆アゴニスト |
| 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 |
| EP2004659A1 (en) | 2006-04-12 | 2008-12-24 | Wyeth | Substituted-dihydro[1,4]oxazino[2,3,4-hi]indazole derivatives as 5-hydroxytryptamine-6 ligands |
| 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 |
| US20080021026A1 (en) | 2006-07-20 | 2008-01-24 | Mehmet Kahraman | Benzothiophene inhibitors of rho kinase |
| WO2008042422A2 (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 |
| WO2009035671A1 (en) | 2007-09-12 | 2009-03-19 | Janssen Pharmaceutica N.V. | 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 |
| CA2706391A1 (en) | 2007-11-21 | 2009-05-28 | 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 |
| JPWO2009072621A1 (ja) | 2007-12-07 | 2011-04-28 | 日産化学工業株式会社 | 置換ジヒドロアゾール化合物及び有害生物防除剤 |
| 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 |
| 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 |
| 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 |
| US9776963B2 (en) | 2008-11-10 | 2017-10-03 | The Trustees Of The University Of Pennsylvania | Small molecule CD4 mimetics and uses thereof |
| CN102395585A (zh) | 2009-01-30 | 2012-03-28 | 米伦纽姆医药公司 | 杂芳基化合物和其作为pi3k抑制剂的用途 |
| KR20110132564A (ko) | 2009-02-11 | 2011-12-08 | 선오비온 파마슈티컬스 인코포레이티드 | 히스타민 ｈ3 역 작용제 및 길항제, 및 이의 사용 방법 |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| 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 |
| WO2011017389A1 (en) | 2009-08-05 | 2011-02-10 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv |
| WO2011036889A1 (ja) | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| UA107943C2 (xx) | 2009-11-16 | 2015-03-10 | Lilly Co Eli | Сполуки спіропіперидину як антагоністи рецептора orl-1 |
| SI2501704T1 (sl) | 2009-11-16 | 2013-11-29 | Eli Lilly Company | Spojine spiropiperidina kot antagonisti oral-1 receptorja |
| 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 |
| NZ767139A (en) | 2009-12-04 | 2022-08-26 | Sunovion Pharmaceuticals Inc | Multicyclic compounds and methods of use thereof |
| ES2610248T3 (es) | 2009-12-28 | 2017-04-26 | General Incorporated Association Pharma Valley Project Supporting Organisation | Compuesto de 1,3,4-oxadiazol-2-carboxamida |
| EP2531804B1 (en) | 2010-02-01 | 2018-08-29 | SGL Carbon SE | Ceramic based armor and process for producing said armor |
| EP2377850A1 (en) | 2010-03-30 | 2011-10-19 | Pharmeste S.r.l. | TRPV1 vanilloid receptor antagonists with a bicyclic portion |
| EP2560636A4 (en) | 2010-04-23 | 2013-11-27 | Kineta Inc | ANTIVIRAL CONNECTIONS |
| 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 |
| KR20140099556A (ko) | 2010-12-16 | 2014-08-12 | 에프. 호프만-라 로슈 아게 | 트라이사이클릭 pi3k 억제제 화합물 및 이의 사용 방법 |
| US8569339B2 (en) | 2011-03-10 | 2013-10-29 | Boehringer Ingelheim International Gmbh | Soluble guanylate cyclase activators |
| 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 |
| MX2014003600A (es) | 2011-10-05 | 2014-04-25 | Hoffmann La Roche | Ciclohexil-4h,6h-5-oxa-2,3,10b-triaza-benzo[e]azulenos como antagonistas v1a. |
| WO2013067248A1 (en) | 2011-11-04 | 2013-05-10 | Vertex Pharmaceuticals Incorporated | Benzoxazines as modulators of ion channels |
| CN104039789B (zh) | 2011-12-22 | 2016-09-07 | 默克专利股份有限公司 | 四氮杂-环戊二烯并[a]茚基及其作为正向变构调节剂的用途 |
| US10189825B2 (en) | 2012-02-08 | 2019-01-29 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| BR112014031899A8 (pt) | 2012-06-20 | 2017-10-24 | Univ Vanderbilt | composto, composição farmacêutica, e, método para tratamento de um distúrbio |
| HRP20161613T1 (hr) | 2012-11-13 | 2017-01-13 | Array Biopharma, Inc. | Tvari bicikličke ureje, tioureje, gvanidina i cijanogvanidina korisne za liječenje boli |
| EP2938341B1 (en) | 2012-12-31 | 2018-09-05 | Sunovion Pharmaceuticals Inc. | 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 |
| CN107567454B (zh) | 2015-02-11 | 2020-02-18 | 赛诺维信制药公司 | 用于治疗cns障碍的稠合二氢-4h-吡唑并[5,1-c][1,4]噁嗪基化合物及其类似物 |
| US10196403B2 (en) * | 2016-07-29 | 2019-02-05 | Sunovion Pharmaceuticals Inc. | Compounds and compositions and uses thereof |
| KR20190065246A (ko) | 2016-07-29 | 2019-06-11 | 선오비온 파마슈티컬스 인코포레이티드 | 화합물 및 조성물 및 이들의 용도 |
| WO2018151861A1 (en) | 2017-02-16 | 2018-08-23 | Sunovion Pharamaceuticials Inc. | Methods of treating schizophrenia |
| JP7191085B2 (ja) | 2017-08-02 | 2022-12-16 | サノビオン ファーマシューティカルズ インク | イソクロマン化合物およびその使用 |
| US20210008030A1 (en) | 2018-02-16 | 2021-01-14 | Sunovion Pharmaceuticals Inc. | Methods of treating social function disorders |
| EP3752508A1 (en) | 2018-02-16 | 2020-12-23 | Sunovion Pharmaceuticals Inc. | Salts, crystal forms, and production methods thereof |
| US20200179336A1 (en) | 2018-12-06 | 2020-06-11 | Sunovion Pharmaceuticals Inc. | Methods of treating neurological and psychiatric disorders |
-
2018
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- 2018-08-01 AU AU2018312559A patent/AU2018312559B2/en not_active Ceased
- 2018-08-01 WO PCT/US2018/044854 patent/WO2019028165A1/en not_active Ceased
- 2018-08-01 EP EP18756100.6A patent/EP3661929B1/en active Active
- 2018-08-01 CA CA3070993A patent/CA3070993C/en active Active
-
2020
- 2020-01-23 IL IL272200A patent/IL272200A/en unknown
- 2020-08-12 US US16/991,771 patent/US11491133B2/en active Active
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