JP2009538853A5 - - Google Patents
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- JP2009538853A5 JP2009538853A5 JP2009512482A JP2009512482A JP2009538853A5 JP 2009538853 A5 JP2009538853 A5 JP 2009538853A5 JP 2009512482 A JP2009512482 A JP 2009512482A JP 2009512482 A JP2009512482 A JP 2009512482A JP 2009538853 A5 JP2009538853 A5 JP 2009538853A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- imidazo
- pyrazine
- methoxy
- methyl
- 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.)
- Pending
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 35
- 208000035475 disorder Diseases 0.000 claims 34
- -1 4-isopropyloxy-8-methoxy-3-methyl-1-propyl-imidazo [1,5-a] pyrido [3,2-e] pyrazine 8-methoxy-1,3-dimethyl-4- (2,3,6-trifluorobenzyloxy) -imidazo [1,5-a] pyrido [3,2-e] pyrazine Chemical compound 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000004122 cyclic group Chemical group 0.000 claims 17
- 208000028017 Psychotic disease Diseases 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical group 0.000 claims 14
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 10
- 201000000980 schizophrenia Diseases 0.000 claims 8
- 230000003542 behavioural effect Effects 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 206010026749 Mania Diseases 0.000 claims 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000008451 emotion Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
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- 208000012239 Developmental disease Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 208000013403 hyperactivity Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000000926 neurological effect Effects 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000020016 psychiatric disease Diseases 0.000 claims 3
- 230000001107 psychogenic effect Effects 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
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- 241000124008 Mammalia Species 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 2
- 208000020114 Schizophrenia and other psychotic disease Diseases 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
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- 229910052763 palladium Inorganic materials 0.000 claims 2
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000000698 schizophrenic effect Effects 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- MHLWHSGDDQJVTO-UHFFFAOYSA-N 1-(4-methoxy-11-methyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraen-10-yl)-3-propan-2-ylurea Chemical compound N12CN(OC)C=C2C=NC2=C1N(CCC)CC(C)=C2NC(=O)NC(C)C MHLWHSGDDQJVTO-UHFFFAOYSA-N 0.000 claims 1
- SKKJBUVASPYLCP-UHFFFAOYSA-N 10-cyclopentyloxy-13-ethyl-4-methoxy-11-methyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene 13-ethyl-4-methoxy-11-methyl-10-propoxy-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound N1=CC2=CN(OC)CN2C2=C1C(OCCC)=C(C)CN2CC.N12CN(OC)C=C2C=NC2=C1N(CC)CC(C)=C2OC1CCCC1 SKKJBUVASPYLCP-UHFFFAOYSA-N 0.000 claims 1
- XNISOERFESPZHR-UHFFFAOYSA-N 10-ethyl-4-methoxy-11-methyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene 4-methoxy-10,11-dimethyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound N12CN(OC)C=C2C=NC2=C1N(CCC)CC(C)=C2C.N12CN(OC)C=C2C=NC2=C1N(CCC)CC(C)=C2CC XNISOERFESPZHR-UHFFFAOYSA-N 0.000 claims 1
- XEQRRFBPNRKREH-UHFFFAOYSA-N 12-methoxy-10,11-dimethyl-4-(4-methyl-2-propylimidazol-1-yl)-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound CCCN1C(OC)C(C)=C(C)C(N=CC2=C3)=C1N2CN3N1C=C(C)N=C1CCC XEQRRFBPNRKREH-UHFFFAOYSA-N 0.000 claims 1
- HDEZRZBDCNJDLJ-UHFFFAOYSA-N 12-methoxy-10,11-dimethyl-4-(4-methylpiperazin-1-yl)-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound CCCN1C(OC)C(C)=C(C)C(N=CC2=C3)=C1N2CN3N1CCN(C)CC1 HDEZRZBDCNJDLJ-UHFFFAOYSA-N 0.000 claims 1
- VODYAHMSBGDIQH-UHFFFAOYSA-N 13-ethyl-4-methoxy-11-methyl-10-methylsulfanyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene 4-methoxy-11-methyl-10-methylsulfanyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound N12CN(OC)C=C2C=NC2=C1N(CC)CC(C)=C2SC.N12CN(OC)C=C2C=NC2=C1N(CCC)CC(C)=C2SC VODYAHMSBGDIQH-UHFFFAOYSA-N 0.000 claims 1
- PGDQQHOVGFSIGS-UHFFFAOYSA-N 13-ethyl-4-methoxy-11-methyl-10-methylsulfinyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene 4-methoxy-11-methyl-10-methylsulfonyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound N12CN(OC)C=C2C=NC2=C1N(CC)CC(C)=C2S(C)=O.N12CN(OC)C=C2C=NC2=C1N(CCC)CC(C)=C2S(C)(=O)=O PGDQQHOVGFSIGS-UHFFFAOYSA-N 0.000 claims 1
- ZFESMIUEBMKAHN-UHFFFAOYSA-N 13-ethyl-4-methoxy-11-methyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene 4-methoxy-11-methyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound C(C)N1CC(=CC=2N=CC=3N(C21)CN(C3)OC)C.CON3CN2C(C=NC1=C2N(CC(=C1)C)CCC)=C3 ZFESMIUEBMKAHN-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims 1
- CNDQETATHMBYDH-UHFFFAOYSA-N 4-(2-ethyl-4-methylimidazol-1-yl)-12-methoxy-10,11-dimethyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound CCCN1C(OC)C(C)=C(C)C(N=CC2=C3)=C1N2CN3N1C=C(C)N=C1CC CNDQETATHMBYDH-UHFFFAOYSA-N 0.000 claims 1
- HBUHADWINCSDBW-UHFFFAOYSA-N 4-methoxy-10,11,13-trimethyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraene Chemical compound CN1CC(C)=C(C)C2=C1N1CN(OC)C=C1C=N2 HBUHADWINCSDBW-UHFFFAOYSA-N 0.000 claims 1
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 claims 1
- 206010054196 Affect lability Diseases 0.000 claims 1
- 208000017194 Affective disease Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 208000036640 Asperger disease Diseases 0.000 claims 1
- 201000006062 Asperger syndrome Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 206010006362 Brief psychotic disorder, with postpartum onset Diseases 0.000 claims 1
- CUNOIBNJEWZQLY-UHFFFAOYSA-N C(C)N1CC(=C(C=2N=CC=3N(C21)CN(C3)OC)OC(C)C)C.COC3=C(C=NC2=C3N=CC=3N2CN(C3)OC)C Chemical compound C(C)N1CC(=C(C=2N=CC=3N(C21)CN(C3)OC)OC(C)C)C.COC3=C(C=NC2=C3N=CC=3N2CN(C3)OC)C CUNOIBNJEWZQLY-UHFFFAOYSA-N 0.000 claims 1
- SUUZQBPJXAPCMG-UHFFFAOYSA-N C(C)OC(=O)[Mg]C(F)F Chemical compound C(C)OC(=O)[Mg]C(F)F SUUZQBPJXAPCMG-UHFFFAOYSA-N 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- XZYWJSFVJBKGTK-UHFFFAOYSA-N COC1=C(CN(C2=C1N=CC=1N2CN(C1)OC)C)C.COC1=C(CN(C2=C1N=CC=1N2CN(C1)OC)CC)C Chemical compound COC1=C(CN(C2=C1N=CC=1N2CN(C1)OC)C)C.COC1=C(CN(C2=C1N=CC=1N2CN(C1)OC)CC)C XZYWJSFVJBKGTK-UHFFFAOYSA-N 0.000 claims 1
- UOJDUUNYGYQDEO-UHFFFAOYSA-N COC1=CCN(C2=C1N=CC=1N2CN(C1)OC)CCC.COC1=C(CN(C2=C1N=CC=1N2CN(C1)OC)CCC)C Chemical compound COC1=CCN(C2=C1N=CC=1N2CN(C1)OC)CCC.COC1=C(CN(C2=C1N=CC=1N2CN(C1)OC)CCC)C UOJDUUNYGYQDEO-UHFFFAOYSA-N 0.000 claims 1
- XJCQRSXQWMNSPO-UHFFFAOYSA-N CON1CN2C(C=NC3=C2N(CC(=C3NC(=O)N)C)CCC)=C1.CON1CN3C(C=NC2=C3N(CC(=C2NC(=O)NC)C)CCC)=C1 Chemical compound CON1CN2C(C=NC3=C2N(CC(=C3NC(=O)N)C)CCC)=C1.CON1CN3C(C=NC2=C3N(CC(=C2NC(=O)NC)C)CCC)=C1 XJCQRSXQWMNSPO-UHFFFAOYSA-N 0.000 claims 1
- KINZNAKMKMXZSU-UHFFFAOYSA-N CON1CN2C(C=NC3=C2N(CC(=C3NC(=O)OC)C)CCC)=C1.N1=CC=NC3=C1C=CC=N3 Chemical compound CON1CN2C(C=NC3=C2N(CC(=C3NC(=O)OC)C)CCC)=C1.N1=CC=NC3=C1C=CC=N3 KINZNAKMKMXZSU-UHFFFAOYSA-N 0.000 claims 1
- GJNBAHWMXFEVEJ-UHFFFAOYSA-N CON1CN2C(C=NC3=C2N=CC(=C3SC)C)=C1.CN1CC(=C(C=3N=CC=2N(C31)CN(C2)OC)SC)C Chemical compound CON1CN2C(C=NC3=C2N=CC(=C3SC)C)=C1.CN1CC(=C(C=3N=CC=2N(C31)CN(C2)OC)SC)C GJNBAHWMXFEVEJ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
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- VYQHVJLYCVBMPP-UHFFFAOYSA-N N-(4-methoxy-11-methyl-13-phenyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraen-10-yl)methanesulfonamide Chemical compound C=1N(OC)CN2C=1C=NC(C(=C(C)C1)NS(C)(=O)=O)=C2N1C1=CC=CC=C1 VYQHVJLYCVBMPP-UHFFFAOYSA-N 0.000 claims 1
- SPQOJNXJTIXEIH-UHFFFAOYSA-N N-(4-methoxy-11-methyl-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraen-10-yl)-4-methylbenzenesulfonamide Chemical compound N12CN(OC)C=C2C=NC2=C1N(CCC)CC(C)=C2NS(=O)(=O)C1=CC=C(C)C=C1 SPQOJNXJTIXEIH-UHFFFAOYSA-N 0.000 claims 1
- PYLLDDLPBABELC-UHFFFAOYSA-N N-[11-methyl-4-(4-methyl-2-propylimidazol-1-yl)-13-propyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraen-10-yl]methanesulfonamide Chemical compound CCCN1CC(C)=C(NS(C)(=O)=O)C(N=CC2=C3)=C1N2CN3N1C=C(C)N=C1CCC PYLLDDLPBABELC-UHFFFAOYSA-N 0.000 claims 1
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- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 208000018724 torsion dystonia Diseases 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| JP2009538853A JP2009538853A (ja) | 2009-11-12 |
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| TW200815436A (en) * | 2006-05-30 | 2008-04-01 | Elbion Ag | 4-amino-pyrido[3,2-e]pyrazines, their use as inhibitors of phosphodiesterase 10, and processes for preparing them |
| CA2671980C (en) * | 2006-12-13 | 2015-05-05 | Aska Pharmaceutical Co., Ltd. | Quinoxaline derivatives |
| US20090143392A1 (en) * | 2007-11-30 | 2009-06-04 | Elbion Gmbh | Methods of Treating Obesity and Metabolic Disorders |
| US20090143361A1 (en) * | 2007-11-30 | 2009-06-04 | Elbion Gmbh | Pyrido[3,2-E]Pyrazines, Process For Preparing The Same, And Their Use As Inhibitors Of Phosphodiesterase 10 |
| KR20100110804A (ko) * | 2007-11-30 | 2010-10-13 | 와이어쓰 엘엘씨 | 포스포디에스테라제 10의 저해물질로서의 아릴 및 헤테로아릴 융합된 이미다조[1,5-ａ]피라진 |
| EA018927B1 (ru) * | 2008-05-07 | 2013-11-29 | Х. Лундбекк А/С | Способ лечения когнитивного расстройства, ассоциированного с шизофренией |
| US20100120762A1 (en) * | 2008-11-07 | 2010-05-13 | Wyeth | Triazine derivatives as inhibitors of phosphodiesterases |
| CN103108548A (zh) * | 2010-07-20 | 2013-05-15 | 昔勒尼药品公司 | 使用环酰胺衍生物治疗σ受体介导的病症的方法 |
| WO2012012542A1 (en) * | 2010-07-20 | 2012-01-26 | Cyrenaic Pharmaceuticals, Inc. | Methods of use of cyclic amide derivatives to treat schizophrenia |
| US9540379B2 (en) | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| CN103476757A (zh) | 2011-02-18 | 2013-12-25 | 阿勒根公司 | 作为磷酸二酯酶10(pde10a)的抑制剂的取代的6,7-二烷氧基-3-异喹啉醇衍生物 |
| US9938269B2 (en) | 2011-06-30 | 2018-04-10 | Abbvie Inc. | Inhibitor compounds of phosphodiesterase type 10A |
| JP2014526453A (ja) * | 2011-09-09 | 2014-10-06 | ハー・ルンドベック・アクチエゼルスカベット | ピリジン化合物およびそれらの使用 |
| US20130116241A1 (en) | 2011-11-09 | 2013-05-09 | Abbvie Inc. | Novel inhibitor compounds of phosphodiesterase type 10a |
| AU2012334011A1 (en) | 2011-11-09 | 2014-05-15 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic carboxamides useful as inhibitors of phosphodiesterase type 10A |
| MX361539B (es) | 2012-04-25 | 2018-12-10 | Takeda Pharmaceuticals Co | Compuesto heterociclico nitrogenado. |
| EP2873669A4 (en) * | 2012-07-13 | 2015-11-25 | Takeda Pharmaceutical | HETEROCYCLIC CONNECTION |
| US20140045856A1 (en) * | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| UY34980A (es) | 2012-08-17 | 2014-03-31 | Abbvie Inc | Nuevos compuestos inhibidores de la fosfodiesterasa del tipo 10a |
| EP2895489B1 (en) | 2012-09-17 | 2017-10-18 | AbbVie Deutschland GmbH & Co. KG | Novel inhibitor compounds of phosphodiesterase type 10a |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| US9790203B2 (en) | 2012-11-26 | 2017-10-17 | Abbvie Inc. | Inhibitor compounds of phosphodiesterase type 10A |
| US9200005B2 (en) | 2013-03-13 | 2015-12-01 | AbbVie Deutschland GmbH & Co. KG | Inhibitor compounds of phosphodiesterase type 10A |
| EP2975031A4 (en) | 2013-03-14 | 2017-04-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| CN105209462A (zh) | 2013-03-14 | 2015-12-30 | 艾伯维德国有限责任两合公司 | 磷酸二酯酶10a型的新型抑制剂化合物 |
| JP6427491B2 (ja) | 2013-07-03 | 2018-11-21 | 武田薬品工業株式会社 | 複素環化合物 |
| ES2950424T3 (es) | 2013-07-03 | 2023-10-09 | Takeda Pharmaceuticals Co | Compuesto de amida |
| WO2015006689A1 (en) | 2013-07-12 | 2015-01-15 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using pde10a inhibitors and methods to measure pde10a expression |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| US10189841B2 (en) | 2015-11-20 | 2019-01-29 | Forma Therapeutics, Inc. | Purinones as ubiquitin-specific protease 1 inhibitors |
| IL308650B2 (en) | 2017-06-21 | 2025-08-01 | Minerva Neurosciences Inc | Gastro-resistant controlled release oral dosage forms |
| WO2020065583A1 (en) | 2018-09-28 | 2020-04-02 | Takeda Pharmaceutical Company Limited | Balipodect for treating or preventing autism spectrum disorders |
| CN114524808B (zh) * | 2022-02-21 | 2023-10-24 | 深圳市儿童医院 | 一种吡唑衍生物及其作为pde10抑制剂的用途 |
| CN114524806B (zh) * | 2022-02-22 | 2024-09-03 | 深圳市儿童医院 | 一种三氮唑衍生物及其作为pde10抑制剂的用途 |
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|---|---|---|---|---|
| US5055465A (en) * | 1989-05-31 | 1991-10-08 | Berlex Laboratories, Inc. | Imidazoquinoxalinones, their aza analogs and process for their preparation |
| AU657986B2 (en) * | 1991-06-14 | 1995-03-30 | Pharmacia & Upjohn Company | Imidazo(1,5-a)quinoxalines |
| DE19510965A1 (de) * | 1995-03-24 | 1996-09-26 | Asta Medica Ag | Neue Pyrido/3,2-e/pyrazinone mit antiasthmatischer Wirksamkeit und Verfahren zu deren Herstellung |
| US20030032579A1 (en) * | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| IL149106A0 (en) | 2001-04-20 | 2002-11-10 | Pfizer Prod Inc | Therapeutic use of selective pde10 inhibitors |
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- 2007-05-29 RU RU2008152440/04A patent/RU2008152440A/ru not_active Application Discontinuation
- 2007-05-29 EP EP07725639A patent/EP2021342A1/en not_active Withdrawn
- 2007-05-29 CN CNA2007800193040A patent/CN101454324A/zh active Pending
- 2007-05-29 KR KR1020087031860A patent/KR20090013834A/ko not_active Withdrawn
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- 2007-05-29 AU AU2007267392A patent/AU2007267392A1/en not_active Abandoned
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- 2008-11-27 GT GT200800265A patent/GT200800265A/es unknown
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2009
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