JP2011526282A5 - - Google Patents
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- JP2011526282A5 JP2011526282A5 JP2011516574A JP2011516574A JP2011526282A5 JP 2011526282 A5 JP2011526282 A5 JP 2011526282A5 JP 2011516574 A JP2011516574 A JP 2011516574A JP 2011516574 A JP2011516574 A JP 2011516574A JP 2011526282 A5 JP2011526282 A5 JP 2011526282A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- cycloalkyl
- alkyl
- compound
- benzo
- 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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- 150000001875 compounds Chemical class 0.000 claims description 126
- -1 tetrahydroquinolyl Chemical group 0.000 claims description 62
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000005605 benzo group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 230000002996 emotional effect Effects 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000000698 schizophrenic effect Effects 0.000 claims description 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
- 208000014094 Dystonic disease Diseases 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000010118 dystonia Diseases 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
- 201000003631 narcolepsy Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 2
- 208000015891 sexual disease Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- XAWPSRJAJAOWID-UHFFFAOYSA-N 1-methyl-3-(4-oxopiperidin-1-yl)-4-[4-(quinolin-2-ylmethoxy)phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1C(=O)N(C)C(=O)C=1N1CCC(=O)CC1 XAWPSRJAJAOWID-UHFFFAOYSA-N 0.000 claims 1
- QMTSOSIYCBNSGT-UHFFFAOYSA-N 1-methyl-3-morpholin-4-yl-4-[4-(quinolin-2-ylmethoxy)phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1C(=O)N(C)C(=O)C=1N1CCOCC1 QMTSOSIYCBNSGT-UHFFFAOYSA-N 0.000 claims 1
- AZIILQLLFMOMOD-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,3-dimethyl-5-[4-(quinolin-2-ylmethoxy)phenyl]imidazol-2-one Chemical compound C1=CC(OC)=CC=C1C(N(C(=O)N1C)C)=C1C(C=C1)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 AZIILQLLFMOMOD-UHFFFAOYSA-N 0.000 claims 1
- KITCZNNLGGJVJK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,5,5-trimethyl-3-[4-(quinolin-2-ylmethoxy)phenyl]pyrrol-2-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)C(=O)N(C)C1(C)C KITCZNNLGGJVJK-UHFFFAOYSA-N 0.000 claims 1
- GDVDWTFSOBWQBD-UHFFFAOYSA-N 4-(4-methoxyphenyl)-5,5-dimethyl-3-[4-(quinolin-2-ylmethoxy)phenyl]-1h-pyrrol-2-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)C(=O)NC1(C)C GDVDWTFSOBWQBD-UHFFFAOYSA-N 0.000 claims 1
- PMEYPGMSMZQPFB-UHFFFAOYSA-N 4-(4-methoxyphenyl)-5,5-dimethyl-3-[4-(quinolin-2-ylmethoxy)phenyl]furan-2-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)C(=O)OC1(C)C PMEYPGMSMZQPFB-UHFFFAOYSA-N 0.000 claims 1
- YPKWRGUWVLBHFC-UHFFFAOYSA-N 5,5-dimethyl-4-pyridin-4-yl-3-[4-(quinolin-2-ylmethoxy)phenyl]-1h-pyrrol-2-one Chemical compound CC1(C)NC(=O)C(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)=C1C1=CC=NC=C1 YPKWRGUWVLBHFC-UHFFFAOYSA-N 0.000 claims 1
- CREHZYPJXWVELF-UHFFFAOYSA-N 5,5-dimethyl-4-pyridin-4-yl-3-[4-(quinolin-2-ylmethoxy)phenyl]furan-2-one Chemical compound CC1(C)OC(=O)C(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)=C1C1=CC=NC=C1 CREHZYPJXWVELF-UHFFFAOYSA-N 0.000 claims 1
- 206010034158 Pathological gambling Diseases 0.000 claims 1
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 1
- 230000000391 smoking effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004001 thioalkyl group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 229940005529 antipsychotics Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229960004372 aripiprazole Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- KPUFNLPDWGSMGZ-UHFFFAOYSA-N carboxy(nitro)azanide Chemical group OC(=O)[N-][N+]([O-])=O KPUFNLPDWGSMGZ-UHFFFAOYSA-N 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229960000652 sertindole Drugs 0.000 description 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7559408P | 2008-06-25 | 2008-06-25 | |
| US61/075,594 | 2008-06-25 | ||
| US10916208P | 2008-10-28 | 2008-10-28 | |
| US61/109,162 | 2008-10-28 | ||
| US13886608P | 2008-12-18 | 2008-12-18 | |
| US61/138,866 | 2008-12-18 | ||
| US17641309P | 2009-05-07 | 2009-05-07 | |
| US61/176,413 | 2009-05-07 | ||
| PCT/US2009/048426 WO2009158393A1 (en) | 2008-06-25 | 2009-06-24 | 1, 2 disubstituted heterocyclic compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014241945A Division JP5820921B2 (ja) | 2008-06-25 | 2014-11-28 | １，２−二置換複素環式化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011526282A JP2011526282A (ja) | 2011-10-06 |
| JP2011526282A5 true JP2011526282A5 (enExample) | 2012-08-09 |
| JP5658664B2 JP5658664B2 (ja) | 2015-01-28 |
Family
ID=41119866
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011516574A Expired - Fee Related JP5658664B2 (ja) | 2008-06-25 | 2009-06-24 | １，２−二置換複素環式化合物 |
| JP2011516650A Pending JP2011526295A (ja) | 2008-06-25 | 2009-06-25 | ５員および６員複素環化合物 |
| JP2014241945A Expired - Fee Related JP5820921B2 (ja) | 2008-06-25 | 2014-11-28 | １，２−二置換複素環式化合物 |
| JP2015197316A Pending JP2016014061A (ja) | 2008-06-25 | 2015-10-05 | １，２−二置換複素環式化合物 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011516650A Pending JP2011526295A (ja) | 2008-06-25 | 2009-06-25 | ５員および６員複素環化合物 |
| JP2014241945A Expired - Fee Related JP5820921B2 (ja) | 2008-06-25 | 2014-11-28 | １，２−二置換複素環式化合物 |
| JP2015197316A Pending JP2016014061A (ja) | 2008-06-25 | 2015-10-05 | １，２−二置換複素環式化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (7) | US8071595B2 (enExample) |
| EP (2) | EP2297133B1 (enExample) |
| JP (4) | JP5658664B2 (enExample) |
| KR (2) | KR20110031355A (enExample) |
| CN (2) | CN102131801B (enExample) |
| AU (2) | AU2009262241B2 (enExample) |
| BR (2) | BRPI0914772A2 (enExample) |
| CA (2) | CA2729259A1 (enExample) |
| MX (2) | MX2011000175A (enExample) |
| TW (2) | TWI458723B (enExample) |
| WO (2) | WO2009158393A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5627574B2 (ja) * | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| BRPI0914772A2 (pt) | 2008-06-25 | 2015-10-20 | Envivo Pharmaceuticals Inc | compostos heterocíclicos 1,2-dissubstituídos |
| CA2761032A1 (en) | 2009-05-07 | 2010-11-11 | Envivo Pharmaceuticals, Inc. | Phenoxymethyl heterocyclic compounds |
| MA33451B1 (fr) | 2009-06-26 | 2012-07-03 | Novartis Ag | Dérivés d'imidazolidin-2-one 1,3-disubstitués en tant qu'inhibiteurs de cyp 17 |
| EP2601192B1 (en) * | 2010-08-04 | 2017-03-01 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| US8883788B2 (en) | 2010-08-04 | 2014-11-11 | Takeda Pharmaceutical Company Limited | Fused heterocyclic ring compound |
| AU2011305568B2 (en) | 2010-09-20 | 2015-12-10 | Ironwood Pharmaceuticals, Inc. | Imidazotriazinone compounds |
| CN107141309A (zh) | 2011-01-11 | 2017-09-08 | 桑诺维恩药品公司 | 杂芳基化合物及其使用方法 |
| MX2013009575A (es) | 2011-02-18 | 2014-10-14 | Exonhit Therapeutics Sa | Derivados de 6, 7-dialcoxi-3-isoquinolinol sustituidos como inhibidores de fosfodiesterasa 10 (pdei0a). |
| EA023064B1 (ru) | 2011-04-28 | 2016-04-29 | Новартис Аг | ИНГИБИТОРЫ 17α-ГИДРОКСИЛАЗЫ/C-ЛИАЗЫ |
| WO2013047411A1 (ja) * | 2011-09-29 | 2013-04-04 | 富士フイルム株式会社 | 新規なトリアジン誘導体、紫外線吸収剤 |
| HK1206726A1 (en) | 2012-03-19 | 2016-01-15 | Ironwood Pharmaceuticals, Inc. | Imidazotriazinone compounds |
| WO2013185284A1 (en) | 2012-06-12 | 2013-12-19 | Abbott Laboratories | Pyridinone and pyridazinone derivatives |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| TW201512201A (zh) * | 2013-03-14 | 2015-04-01 | Forum Pharmaceuticals Inc | 化合物的多晶型及鹽類 |
| US9464076B2 (en) | 2013-03-15 | 2016-10-11 | Daiichi Sankyo Company, Limited | Benzothiophene derivative |
| TWI634114B (zh) * | 2013-05-08 | 2018-09-01 | 永恒生物科技公司 | 作為激酶抑制劑之呋喃酮化合物 |
| CN105324376B (zh) | 2013-06-27 | 2017-06-23 | 辉瑞大药厂 | 杂芳族化合物及其作为多巴胺d1配体的用途 |
| US10039764B2 (en) | 2013-07-12 | 2018-08-07 | 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) |
| US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
| CN104211638A (zh) * | 2014-08-13 | 2014-12-17 | 李增 | 一种脂肪氨基取代的芸香碱类衍生物及其制备和作为抗阿尔兹海默症的药物中的应用 |
| CN104610134B (zh) * | 2015-01-29 | 2017-01-25 | 安徽星宇化工有限公司 | 一种6‑甲基‑2‑吡啶基甲醇的制备方法 |
| WO2016183266A1 (en) | 2015-05-13 | 2016-11-17 | Enanta Pharmaceuticals, Inc. | Ehpatitis b antiviral agents |
| US10179131B2 (en) * | 2015-07-13 | 2019-01-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| KR102398439B1 (ko) | 2016-03-07 | 2022-05-16 | 이난타 파마슈티칼스, 인코포레이티드 | B형 간염 항바이러스제 |
| ES3053505T3 (en) * | 2017-03-23 | 2026-01-22 | Clavius Pharmaceuticals Llc | Tri-substituted imidazoles for the inhibition of tgf beta and methods of treatment |
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| US10729688B2 (en) | 2018-03-29 | 2020-08-04 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| US12077548B2 (en) | 2018-08-22 | 2024-09-03 | Clavius Pharmaceuticals, LLC. | Substituted imidazoles for the inhibition of TGF-β and methods of treatment |
| CA3113235A1 (en) | 2018-09-21 | 2020-03-26 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| IL283190B2 (en) | 2018-11-21 | 2025-08-01 | Enanta Pharm Inc | Functionalized heterocycles as antiviral agents |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| US11236111B2 (en) | 2019-06-03 | 2022-02-01 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
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| KR102811543B1 (ko) | 2019-10-16 | 2025-05-23 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
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| TW202304303A (zh) * | 2021-04-13 | 2023-02-01 | 美商富曼西公司 | 殺真菌之吡啶酮 |
| AU2022359222A1 (en) | 2021-10-09 | 2024-03-21 | Joint Stock Company "Pharmasyntez" | A new class of antiviral drugs |
| WO2024119067A1 (en) | 2022-12-02 | 2024-06-06 | Neumora Therapeutics, Inc. | Methods of treating neurological disorders |
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| IL153851A0 (en) * | 2000-07-27 | 2003-07-31 | Hoffmann La Roche | 3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta |
| US20030032579A1 (en) * | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| US20060111368A1 (en) | 2002-06-26 | 2006-05-25 | Kyowa Hakko Kogyo Co., Ltd. | Phosphodiesterase inhibitor |
| EA012211B1 (ru) * | 2005-01-07 | 2009-08-28 | Пфайзер Продактс Инк. | Гетероароматические соединения хинолинов и их применение в качестве ингибиторов pde10 |
| JP2007145819A (ja) * | 2005-10-28 | 2007-06-14 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| NL2000397C2 (nl) * | 2006-01-05 | 2007-10-30 | Pfizer Prod Inc | Bicyclische heteroarylverbindingen als PDE10 inhibitoren. |
| EP1845098A1 (en) * | 2006-03-29 | 2007-10-17 | Ferrer Internacional, S.A. | Imidazo[1,2-b]pyridazines, their processes of preparation and their use as GABA receptor ligands |
| JP2009535394A (ja) * | 2006-05-02 | 2009-10-01 | ファイザー・プロダクツ・インク | Ｐｄｅ１０阻害剤としての二環式ヘテロアリール化合物 |
| WO2008033455A2 (en) | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Biphenyl and heteroaryl phenyl derivatives as protein tyrosine phosphatases inhibitors |
| RU2439062C2 (ru) * | 2006-10-19 | 2012-01-10 | Ф.Хоффманн-Ля Рош Аг | Производные имидазолона и имидазолидинона как 11в-hsd1 ингибиторы при диабете |
| FR2928924B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 6-heteroaryle-imidazo°1,2-a! pyridines, leur preparation et leur application en therapeutique |
| BRPI0914772A2 (pt) | 2008-06-25 | 2015-10-20 | Envivo Pharmaceuticals Inc | compostos heterocíclicos 1,2-dissubstituídos |
| CA2761032A1 (en) * | 2009-05-07 | 2010-11-11 | Envivo Pharmaceuticals, Inc. | Phenoxymethyl heterocyclic compounds |
| US8614234B2 (en) * | 2009-09-03 | 2013-12-24 | Allergan, Inc. | Compounds as tyrosine kinase modulators |
| ES2879314T3 (es) * | 2010-08-18 | 2021-11-22 | Biosplice Therapeutics Inc | Dicetonas e hidroxicetonas como activadores de la vía de señalización de catenina |
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- 2009-06-24 EP EP09770926.5A patent/EP2297133B1/en active Active
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- 2009-06-25 MX MX2011000176A patent/MX2011000176A/es not_active Application Discontinuation
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- 2009-06-25 KR KR1020117001893A patent/KR20110029153A/ko not_active Withdrawn
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