JP2013521288A5 - - Google Patents
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- JP2013521288A5 JP2013521288A5 JP2012556126A JP2012556126A JP2013521288A5 JP 2013521288 A5 JP2013521288 A5 JP 2013521288A5 JP 2012556126 A JP2012556126 A JP 2012556126A JP 2012556126 A JP2012556126 A JP 2012556126A JP 2013521288 A5 JP2013521288 A5 JP 2013521288A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- aryl
- alkyl
- heterocyclyl
- phenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 3
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 3
- HFBYUIVABHNWMU-UHFFFAOYSA-N 2-[2-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-4-yl]-5-hydroxy-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(N=CC=2)C=2C(=C3C=CNC3=NC=2)Cl)=N1 HFBYUIVABHNWMU-UHFFFAOYSA-N 0.000 claims 2
- KATAWXUHALYMBH-UHFFFAOYSA-N 5-hydroxy-2-[2-(1H-indol-4-yl)pyridin-4-yl]-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(N=CC=2)C=2C=3C=CNC=3C=CC=2)=N1 KATAWXUHALYMBH-UHFFFAOYSA-N 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 claims 2
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 claims 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 claims 2
- 101000600903 Homo sapiens Substance-P receptor Proteins 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims 2
- -1 OR 2 Chemical group 0.000 claims 2
- 102100037346 Substance-P receptor Human genes 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 239000000164 antipsychotic agent Substances 0.000 claims 2
- 229940005529 antipsychotics Drugs 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000002899 monoamine oxidase inhibitor Substances 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 2
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- LPVHTTWQCGEDEQ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-hydroxy-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=C(Cl)C(Cl)=C1 LPVHTTWQCGEDEQ-UHFFFAOYSA-N 0.000 claims 1
- YFHLRKWDSAYBJF-UHFFFAOYSA-N 2-[2-(1-benzylpyrazol-4-yl)pyridin-4-yl]-5-hydroxy-1H-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=NC(C2=CN(CC=3C=CC=CC=3)N=C2)=C1 YFHLRKWDSAYBJF-UHFFFAOYSA-N 0.000 claims 1
- KKNUFGQSBOGSGC-UHFFFAOYSA-N 2-[2-(3-fluoro-4-phenylphenyl)pyridin-4-yl]-5-hydroxy-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(N=CC=2)C=2C=C(F)C(=CC=2)C=2C=CC=CC=2)=N1 KKNUFGQSBOGSGC-UHFFFAOYSA-N 0.000 claims 1
- QQSXEMLMBTYFKG-UHFFFAOYSA-N 2-[2-[3-(difluoromethoxy)phenyl]pyridin-4-yl]-5-hydroxy-1H-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=NC(C=2C=C(OC(F)F)C=CC=2)=C1 QQSXEMLMBTYFKG-UHFFFAOYSA-N 0.000 claims 1
- UYCZQZGBXOJRLJ-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)phenyl]-5-hydroxy-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=CC(C=2OC3=CC=CC=C3C=2)=C1 UYCZQZGBXOJRLJ-UHFFFAOYSA-N 0.000 claims 1
- VENRNROBSMWJOI-UHFFFAOYSA-N 2-[3-(1-benzothiophen-3-yl)phenyl]-5-hydroxy-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(C=CC=2)C=2C3=CC=CC=C3SC=2)=N1 VENRNROBSMWJOI-UHFFFAOYSA-N 0.000 claims 1
- DRHHCJBPWAWGFE-UHFFFAOYSA-N 2-[3-(2,4-dichlorophenyl)phenyl]-5-hydroxy-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=CC(C=2C(=CC(Cl)=CC=2)Cl)=C1 DRHHCJBPWAWGFE-UHFFFAOYSA-N 0.000 claims 1
- BLIWUALRIJJADO-UHFFFAOYSA-N 2-[3-(3h-benzimidazol-5-yl)phenyl]-5-hydroxy-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(C=CC=2)C=2C=C3N=CNC3=CC=2)=N1 BLIWUALRIJJADO-UHFFFAOYSA-N 0.000 claims 1
- OTBMRWHZJMHEPU-UHFFFAOYSA-N 2-[3-[2-bromo-4-(trifluoromethyl)phenoxy]phenyl]-5-hydroxy-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(OC=3C(=CC(=CC=3)C(F)(F)F)Br)C=CC=2)=N1 OTBMRWHZJMHEPU-UHFFFAOYSA-N 0.000 claims 1
- BESHXQPCRPHKTJ-UHFFFAOYSA-N 2-[4-chloro-3-(trifluoromethyl)phenyl]-5-hydroxy-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(C(Cl)=CC=2)C(F)(F)F)=N1 BESHXQPCRPHKTJ-UHFFFAOYSA-N 0.000 claims 1
- TUNMXAZRNVOLDG-UHFFFAOYSA-N 2-fluoro-5-(5-hydroxy-6-oxo-1h-pyrimidin-2-yl)benzonitrile Chemical compound N1C(=O)C(O)=CN=C1C1=CC=C(F)C(C#N)=C1 TUNMXAZRNVOLDG-UHFFFAOYSA-N 0.000 claims 1
- IACKRGCNAQZMIU-UHFFFAOYSA-N 5-hydroxy-2-(3-isoquinolin-5-ylphenyl)-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(C=CC=2)C=2C3=CC=NC=C3C=CC=2)=N1 IACKRGCNAQZMIU-UHFFFAOYSA-N 0.000 claims 1
- OOJRDSJPKZIEAY-UHFFFAOYSA-N 5-hydroxy-2-(3-pyridazin-3-ylphenyl)-1H-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=CC(C=2N=NC=CC=2)=C1 OOJRDSJPKZIEAY-UHFFFAOYSA-N 0.000 claims 1
- HYVYADZZQLBHJZ-UHFFFAOYSA-N 5-hydroxy-2-(3-pyridin-3-ylphenyl)-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=CC(C=2C=NC=CC=2)=C1 HYVYADZZQLBHJZ-UHFFFAOYSA-N 0.000 claims 1
- CENSFAAHRJURFI-UHFFFAOYSA-N 5-hydroxy-2-[2-[1-(3-methylbutyl)pyrazol-4-yl]pyridin-4-yl]-1H-pyrimidin-6-one Chemical compound C1=NN(CCC(C)C)C=C1C1=CC(C=2NC(=O)C(O)=CN=2)=CC=N1 CENSFAAHRJURFI-UHFFFAOYSA-N 0.000 claims 1
- MONCLOFWGGTUNW-UHFFFAOYSA-N 5-hydroxy-2-[3-(1,3-thiazol-4-yl)phenyl]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=CC(C=2N=CSC=2)=C1 MONCLOFWGGTUNW-UHFFFAOYSA-N 0.000 claims 1
- KWQQBUJEAGMQJV-UHFFFAOYSA-N 5-hydroxy-2-[3-(1h-indol-4-yl)phenyl]-3-methylpyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(C=CC=2)C=2C=3C=CNC=3C=CC=2)=N1 KWQQBUJEAGMQJV-UHFFFAOYSA-N 0.000 claims 1
- CMFVPGSVGJIZGE-UHFFFAOYSA-N 5-hydroxy-2-[3-(2-methoxy-1,3-thiazol-5-yl)phenyl]-1h-pyrimidin-6-one Chemical compound S1C(OC)=NC=C1C1=CC=CC(C=2NC(=O)C(O)=CN=2)=C1 CMFVPGSVGJIZGE-UHFFFAOYSA-N 0.000 claims 1
- PWRXYUJJILWYNW-UHFFFAOYSA-N 5-hydroxy-2-[3-(2-phenylethynyl)phenyl]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=CC(C#CC=2C=CC=CC=2)=C1 PWRXYUJJILWYNW-UHFFFAOYSA-N 0.000 claims 1
- TVHMMAYJPULDQY-UHFFFAOYSA-N 5-hydroxy-2-[3-(4-methoxyphenoxy)phenyl]-3-methylpyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC(C=2N(C(=O)C(O)=CN=2)C)=C1 TVHMMAYJPULDQY-UHFFFAOYSA-N 0.000 claims 1
- FFEVCZSBKMQQIP-UHFFFAOYSA-N 5-hydroxy-2-[3-(6-methoxypyrazin-2-yl)phenyl]-1H-pyrimidin-6-one Chemical compound COC1=CN=CC(C=2C=C(C=CC=2)C=2NC(=O)C(O)=CN=2)=N1 FFEVCZSBKMQQIP-UHFFFAOYSA-N 0.000 claims 1
- ZABWLHSHNHMVBN-UHFFFAOYSA-N 5-hydroxy-2-[4-(trifluoromethyl)phenyl]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(O)=CN=C1C1=CC=C(C(F)(F)F)C=C1 ZABWLHSHNHMVBN-UHFFFAOYSA-N 0.000 claims 1
- OMZDYGTZUBRJEF-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-(3-phenoxyphenyl)pyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(OC=3C=CC=CC=3)C=CC=2)=N1 OMZDYGTZUBRJEF-UHFFFAOYSA-N 0.000 claims 1
- XFQLJHLLJPLAPL-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-(3-phenylphenyl)pyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(C=CC=2)C=2C=CC=CC=2)=N1 XFQLJHLLJPLAPL-UHFFFAOYSA-N 0.000 claims 1
- NUMGVMNXCZJKJB-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-(4-phenoxyphenyl)pyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 NUMGVMNXCZJKJB-UHFFFAOYSA-N 0.000 claims 1
- VPJYTFXSFAFIHS-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-(4-phenylmethoxyphenyl)pyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 VPJYTFXSFAFIHS-UHFFFAOYSA-N 0.000 claims 1
- ADYPVOJWPWYSHV-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-[2-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-4-yl]pyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(N=CC=2)C=2C=C3C=CNC3=NC=2)=N1 ADYPVOJWPWYSHV-UHFFFAOYSA-N 0.000 claims 1
- UQDMTOXFCIBLQD-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-[3-(4-methyl-2,3-dihydropyrido[3,2-b][1,4]oxazin-7-yl)phenyl]pyrimidin-4-one Chemical compound C=1N=C2N(C)CCOC2=CC=1C(C=1)=CC=CC=1C1=NC=C(O)C(=O)N1C UQDMTOXFCIBLQD-UHFFFAOYSA-N 0.000 claims 1
- OGDUFEGAVPGIMC-UHFFFAOYSA-N 5-hydroxy-3-methyl-2-[3-[3-(trifluoromethyl)phenoxy]phenyl]pyrimidin-4-one Chemical compound C1=C(O)C(=O)N(C)C(C=2C=C(OC=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=N1 OGDUFEGAVPGIMC-UHFFFAOYSA-N 0.000 claims 1
- ZYOSEPWKINTHBG-UHFFFAOYSA-N 6-chloro-5-hydroxy-3-methyl-2-(4-phenoxyphenyl)pyrimidin-4-one Chemical compound ClC1=C(O)C(=O)N(C)C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 ZYOSEPWKINTHBG-UHFFFAOYSA-N 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 206010056465 Food craving Diseases 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 102000010909 Monoamine Oxidase Human genes 0.000 claims 1
- 108010062431 Monoamine oxidase Proteins 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims 1
- 229940089973 Sodium channel antagonist Drugs 0.000 claims 1
- 239000000674 adrenergic antagonist Substances 0.000 claims 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 claims 1
- 229960002870 gabapentin Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229960001078 lithium Drugs 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IVPXXHZLXUXUEH-UHFFFAOYSA-N n-[3-(5-hydroxy-6-oxo-1h-pyrimidin-2-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2NC(=O)C(O)=CN=2)=C1 IVPXXHZLXUXUEH-UHFFFAOYSA-N 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 229940072228 neurontin Drugs 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229960002748 norepinephrine Drugs 0.000 claims 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
- 229940127240 opiate Drugs 0.000 claims 1
- 239000003402 opiate agonist Substances 0.000 claims 1
- 239000003401 opiate antagonist Substances 0.000 claims 1
- 239000012660 pharmacological inhibitor Substances 0.000 claims 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims 1
- 229960001233 pregabalin Drugs 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 239000003195 sodium channel blocking agent Substances 0.000 claims 1
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 229940102566 valproate Drugs 0.000 claims 1
- 230000004584 weight gain Effects 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
- 0 *C(N=C(*)N(*)C1=O)=C1O Chemical compound *C(N=C(*)N(*)C1=O)=C1O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31038610P | 2010-03-04 | 2010-03-04 | |
| US61/310,386 | 2010-03-04 | ||
| PCT/US2011/026424 WO2011109267A1 (en) | 2010-03-04 | 2011-02-28 | Inhibitors of catechol o-methyl transferase and their use in the treatment of psychotic disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013521288A JP2013521288A (ja) | 2013-06-10 |
| JP2013521288A5 true JP2013521288A5 (cg-RX-API-DMAC10.html) | 2014-04-17 |
| JP5937971B2 JP5937971B2 (ja) | 2016-06-22 |
Family
ID=44542514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012556126A Active JP5937971B2 (ja) | 2010-03-04 | 2011-02-28 | カテコールｏ−メチルトランスフェラーゼの阻害剤および精神障害の治療におけるその使用 |
Country Status (17)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| UA111861C2 (uk) | 2011-11-15 | 2016-06-24 | Такеда Фармасьютікал Компані Лімітед | Ароматична гетероциклічна сполука дигідрокси |
| TWI638802B (zh) | 2012-05-24 | 2018-10-21 | 芬蘭商奧利安公司 | 兒茶酚ｏ－甲基轉移酶活性抑制化合物 |
| RU2701156C9 (ru) | 2012-07-18 | 2019-12-18 | Саншайн Лейк Фарма Ко., Лтд. | Азотсодержащие гетероциклические производные и их применение в фармацевтических препаратах |
| US9573938B2 (en) * | 2012-09-11 | 2017-02-21 | Rutgers, The State University Of New Jersey | Therapeutic hydroxypyridinones, hydroxypyrimidinones and hydroxypyridazinones |
| GB201222711D0 (en) | 2012-12-17 | 2013-01-30 | Takeda Pharmaceutical | Novel compounds |
| RU2642779C2 (ru) | 2012-12-27 | 2018-01-26 | Ф.Хоффманн-Ля Рош Аг | Ингибиторы сомт |
| PT3421462T (pt) | 2013-06-27 | 2023-06-29 | Pfizer | Compostos heteroaromáticos e a sua utilização como ligandos de d1 de dopamina |
| ES2663806T3 (es) | 2013-12-19 | 2018-04-17 | unshine Lake Pharma Co., Ltd. | Derivados heterocíclicos nitrogenados y su aplicación en el tratamiento de la fibrosis tisular |
| PL236355B1 (pl) | 2015-04-02 | 2021-01-11 | Celon Pharma Spolka Akcyjna | Pochodne 7-(morfolin-4-ylo)pirazolo[1,5-α]pirymidyny jako inhibitory kinazy PI3 |
| EP3303347B1 (en) * | 2015-06-08 | 2020-05-06 | The Regents of the University of California | Use of h3k9me3 modulation for enhancing cognitive function |
| EP3892278B1 (en) | 2018-12-06 | 2024-02-28 | Daiichi Sankyo Company, Limited | Cycloalkane-1,3-diamine derivative |
| CN113499525A (zh) * | 2021-08-25 | 2021-10-15 | 骆艳 | 一种针对发展性阅读障碍儿童的训练系统 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3631045A (en) * | 1969-11-04 | 1971-12-28 | American Home Prod | 4 5-diamino-7h-pyrrolo(2 3-d)pyrimidine derivatives |
| US3910913A (en) * | 1969-11-04 | 1975-10-07 | American Home Prod | 4,5-Diamino-7H-pyrrolo{8 2,3-d{9 pyrimidine derivatives |
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