TWI465431B - 活化ampk(腺苷單磷酸活化的蛋白質激酶)之吲哚和吲唑類化合物 - Google Patents
活化ampk(腺苷單磷酸活化的蛋白質激酶)之吲哚和吲唑類化合物 Download PDFInfo
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- TWI465431B TWI465431B TW102112379A TW102112379A TWI465431B TW I465431 B TWI465431 B TW I465431B TW 102112379 A TW102112379 A TW 102112379A TW 102112379 A TW102112379 A TW 102112379A TW I465431 B TWI465431 B TW I465431B
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- alkyl
- alkoxy
- hydroxy
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 2
- 101100321932 Rattus norvegicus Prkaa2 gene Proteins 0.000 title 1
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 898
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 553
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 473
- 229910052731 fluorine Inorganic materials 0.000 claims description 425
- 229910052739 hydrogen Inorganic materials 0.000 claims description 326
- 150000001875 compounds Chemical class 0.000 claims description 307
- 150000003839 salts Chemical class 0.000 claims description 282
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 269
- 125000001424 substituent group Chemical group 0.000 claims description 249
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 239
- -1 hydroxy-substituted cyclobutyl group Chemical group 0.000 claims description 215
- 125000003118 aryl group Chemical class 0.000 claims description 197
- 229910052801 chlorine Inorganic materials 0.000 claims description 179
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 173
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 163
- 125000000623 heterocyclic group Chemical group 0.000 claims description 143
- 239000000126 substance Substances 0.000 claims description 136
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 83
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 66
- 125000000468 ketone group Chemical group 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 57
- 125000002757 morpholinyl group Chemical group 0.000 claims description 56
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 56
- 125000001425 triazolyl group Chemical group 0.000 claims description 56
- 125000002393 azetidinyl group Chemical group 0.000 claims description 55
- 125000003386 piperidinyl group Chemical group 0.000 claims description 54
- 125000004193 piperazinyl group Chemical group 0.000 claims description 53
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 49
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 43
- 241000124008 Mammalia Species 0.000 claims description 30
- 125000003566 oxetanyl group Chemical group 0.000 claims description 26
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 229930194542 Keto Natural products 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 6
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 6
- 208000033626 Renal failure acute Diseases 0.000 claims description 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
- 201000011040 acute kidney failure Diseases 0.000 claims description 6
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 208000020832 chronic kidney disease Diseases 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QROCFHQHLVJSBH-UHFFFAOYSA-N 4,6-difluoro-5-[4-[1-(hydroxymethyl)cyclobutyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=C3C(C(O)=O)=CNC3=CC=2F)F)C=CC=1C1(CO)CCC1 QROCFHQHLVJSBH-UHFFFAOYSA-N 0.000 claims 2
- YVBSJPQSGAJIPG-UHFFFAOYSA-N 4,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(C(C)(CO)C)=CC=C1C1=C(F)C=C(NC=C2C(O)=O)C2=C1F YVBSJPQSGAJIPG-UHFFFAOYSA-N 0.000 claims 1
- VPUNMIRZXILGLE-UHFFFAOYSA-N 4,6-difluoro-5-[4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound FC1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1(O)CCC1 VPUNMIRZXILGLE-UHFFFAOYSA-N 0.000 claims 1
- JQJNGAWEMYQJIQ-UHFFFAOYSA-N 4,6-difluoro-5-[4-(oxan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound FC1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1CCCCO1 JQJNGAWEMYQJIQ-UHFFFAOYSA-N 0.000 claims 1
- CZRBSHRHFKGINR-UHFFFAOYSA-N 4,6-difluoro-5-[4-[1-(hydroxymethyl)cyclopropyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=C3C(C(O)=O)=CNC3=CC=2F)F)C=CC=1C1(CO)CC1 CZRBSHRHFKGINR-UHFFFAOYSA-N 0.000 claims 1
- HFTSUSPGKRQUGS-UHFFFAOYSA-N 6-chloro-5-[2-fluoro-4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C(=C1)F)=CC=C1C1(O)CCC1 HFTSUSPGKRQUGS-UHFFFAOYSA-N 0.000 claims 1
- AVSRVMKWMOGUGW-UHFFFAOYSA-N 6-chloro-5-[3-fluoro-4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C(F)C(C(C)(CO)C)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O AVSRVMKWMOGUGW-UHFFFAOYSA-N 0.000 claims 1
- VJRMUMYLSWYBNV-UHFFFAOYSA-N 6-chloro-5-[3-fluoro-4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1F)=CC=C1C1(O)CCC1 VJRMUMYLSWYBNV-UHFFFAOYSA-N 0.000 claims 1
- YFGODCGRXUUSOT-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxyphenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C(C(C)(C)CO)C(OC)=CC(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)=C1 YFGODCGRXUUSOT-UHFFFAOYSA-N 0.000 claims 1
- BUXGLMHGEKZJGD-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(C(C)(CO)C)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O BUXGLMHGEKZJGD-UHFFFAOYSA-N 0.000 claims 1
- KMRDDGOECBQZPA-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxycyclobutyl)-3-methoxyphenyl]-1h-indole-3-carboxylic acid Chemical compound COC1=CC(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)=CC=C1C1(O)CCC1 KMRDDGOECBQZPA-UHFFFAOYSA-N 0.000 claims 1
- FHQXLWCFSUSXBF-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1C1(O)CCC1 FHQXLWCFSUSXBF-UHFFFAOYSA-N 0.000 claims 1
- BYVGXWXQSUMVRV-UHFFFAOYSA-N 6-chloro-5-[4-(1-methylsulfonylazetidin-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound CS(=O)(=O)N1CCC1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=C1 BYVGXWXQSUMVRV-UHFFFAOYSA-N 0.000 claims 1
- YGKWXCWHOYVSAU-UHFFFAOYSA-N 6-chloro-5-[4-(2-hydroxyethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(OCCO)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O YGKWXCWHOYVSAU-UHFFFAOYSA-N 0.000 claims 1
- ZCTWOZZJNVDFFT-UHFFFAOYSA-N 6-chloro-5-[4-(2-hydroxyethyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(CCO)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O ZCTWOZZJNVDFFT-UHFFFAOYSA-N 0.000 claims 1
- QZIZUCHLAKADOE-UHFFFAOYSA-N 6-chloro-5-[4-(2-hydroxyphenyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1C1=CC=CC=C1O QZIZUCHLAKADOE-UHFFFAOYSA-N 0.000 claims 1
- RQZSOXIQLVNMAF-UHFFFAOYSA-N 6-chloro-5-[4-(3-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1C(O)CC1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=C1 RQZSOXIQLVNMAF-UHFFFAOYSA-N 0.000 claims 1
- CNLIFFPPUZLKBG-UHFFFAOYSA-N 6-chloro-5-[4-(3-hydroxypropoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(OCCCO)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O CNLIFFPPUZLKBG-UHFFFAOYSA-N 0.000 claims 1
- RHWVKZPITKBHLD-UHFFFAOYSA-N 6-chloro-5-[4-(3-morpholin-4-ylpropoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCCN1CCOCC1 RHWVKZPITKBHLD-UHFFFAOYSA-N 0.000 claims 1
- NGSWNDMVAWOGHF-UHFFFAOYSA-N 6-chloro-5-[4-(3-piperazin-1-ylpropoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCCN1CCNCC1 NGSWNDMVAWOGHF-UHFFFAOYSA-N 0.000 claims 1
- DKFPQQPTLZDFBM-UHFFFAOYSA-N 6-chloro-5-[4-(oxetan-2-ylmethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCC1CCO1 DKFPQQPTLZDFBM-UHFFFAOYSA-N 0.000 claims 1
- GKPYSXKYDOSNMQ-LJQANCHMSA-N 6-chloro-5-[4-[(2r)-oxan-2-yl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1[C@H]1CCCCO1 GKPYSXKYDOSNMQ-LJQANCHMSA-N 0.000 claims 1
- MJIQWOBJTBDAGR-UHFFFAOYSA-N 6-chloro-5-[4-[1-(hydroxymethyl)cyclobutyl]-3-methoxyphenyl]-1h-indole-3-carboxylic acid Chemical compound COC1=CC(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)=CC=C1C1(CO)CCC1 MJIQWOBJTBDAGR-UHFFFAOYSA-N 0.000 claims 1
- OSNPJCNKGDNYRY-UHFFFAOYSA-N 6-chloro-5-[4-[1-(hydroxymethyl)cyclobutyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=CC=1C1(CO)CCC1 OSNPJCNKGDNYRY-UHFFFAOYSA-N 0.000 claims 1
- OAOIRGKGPZPGRA-UHFFFAOYSA-N 6-chloro-5-[4-[2-(1,2,4-triazol-1-yl)ethoxy]phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCN1C=NC=N1 OAOIRGKGPZPGRA-UHFFFAOYSA-N 0.000 claims 1
- OCYUCPMTHRRWDS-UHFFFAOYSA-N 6-fluoro-5-[4-(2-hydroxyphenyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1=CC=CC=C1O OCYUCPMTHRRWDS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
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- 125000005843 halogen group Chemical group 0.000 description 243
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 84
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 55
- 125000004076 pyridyl group Chemical group 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 47
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 45
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- 125000003545 alkoxy group Chemical group 0.000 description 20
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI644899B (zh) | 2013-02-04 | 2018-12-21 | 健生藥品公司 | Flap調節劑 |
| WO2014121055A2 (en) | 2013-02-04 | 2014-08-07 | Janssen Pharmaceutica Nv | Flap modulators |
| WO2014133008A1 (ja) | 2013-02-27 | 2014-09-04 | 塩野義製薬株式会社 | Ampk活性化作用を有するインドールおよびアザインドール誘導体 |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| JP6435923B2 (ja) * | 2014-03-07 | 2018-12-12 | Jnc株式会社 | ジヒドロピラン化合物、液晶組成物および液晶表示素子 |
| AU2015309863B2 (en) | 2014-08-27 | 2019-12-05 | Shionogi & Co., Ltd. | Azaindole derivative having AMPK-activating effect |
| SG10201902963PA (en) | 2014-10-06 | 2019-05-30 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| WO2016092413A1 (en) * | 2014-12-10 | 2016-06-16 | Pfizer Inc. | Indole and indazole compounds that activate ampk |
| EP3224245B1 (en) | 2014-12-24 | 2018-09-12 | National Institute Of Biological Sciences, Beijing | Necrosis inhibitors |
| EP3310773B1 (en) | 2015-06-18 | 2020-12-02 | 89Bio Ltd. | Substituted 4-benzyl and 4-benzoyl piperidine derivatives |
| CN107847765B (zh) * | 2015-06-18 | 2021-05-04 | 89生物有限公司 | 1,4-取代的哌啶衍生物 |
| WO2017011917A1 (en) * | 2015-07-23 | 2017-01-26 | Thrasos Therapeutics Inc. | Methods for treating and preventing polycystic kidney diseases (pkd) using amp-activated protein kinase (ampk) modulators and activators |
| WO2017146186A1 (ja) | 2016-02-26 | 2017-08-31 | 塩野義製薬株式会社 | Ampk活性化作用を有する5-フェニルアザインドール誘導体 |
| AU2017240685B2 (en) | 2016-03-31 | 2021-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| ES2886587T3 (es) | 2016-04-15 | 2021-12-20 | Cancer Research Tech Ltd | Compuestos heterocíclicos como inhibidores de la quinasa RET |
| EP4104837A3 (en) * | 2016-04-15 | 2023-04-26 | Cancer Research Technology Limited | Heterocyclic compounds as ret kinase inhibitors |
| CN109311848B (zh) | 2016-06-07 | 2022-02-01 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
| WO2018002215A1 (en) | 2016-06-30 | 2018-01-04 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of cardiomyopathies |
| GEP20217329B (en) | 2016-09-30 | 2021-12-10 | Vertex Pharma | Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| HUE052205T2 (hu) | 2016-12-09 | 2021-04-28 | Vertex Pharma | Cisztás fibrózis transzmembrán vezetõképesség szabályzó modulátora, gyógyszerészeti készítmények, kezelési eljárások és eljárás a modulátor elõállítására |
| SMT202400385T1 (it) | 2017-03-23 | 2024-11-15 | Jacobio Pharmaceuticals Co Ltd | Nuovi derivati eterociclici utili come inibitori di shp2 |
| GB201705971D0 (en) | 2017-04-13 | 2017-05-31 | Cancer Res Tech Ltd | Inhibitor compounds |
| BR112019025801A2 (pt) | 2017-06-08 | 2020-07-07 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| BR112020000941A2 (pt) | 2017-07-17 | 2020-07-21 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| US11434201B2 (en) | 2017-08-02 | 2022-09-06 | Vertex Pharmaceuticals Incorporated | Processes for preparing pyrrolidine compounds |
| CA3078893A1 (en) | 2017-10-19 | 2019-04-25 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of cftr modulators |
| CA3085006A1 (en) | 2017-12-08 | 2019-06-13 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| US11760701B2 (en) | 2018-02-27 | 2023-09-19 | The Research Foundation For The State University Of New Yrok | Difluoromethoxylation and trifluoromethoxylation compositions and methods for synthesizing same |
| KR102224550B1 (ko) * | 2018-04-02 | 2021-03-09 | 울산대학교 산학협력단 | 신규한 에테르 화합물, 및 광 산화환원 촉매를 이용하여 활성화된 알켄 화합물로부터 에테르 화합물을 제조하는 방법 |
| EP3774825A1 (en) | 2018-04-13 | 2021-02-17 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| CN108572223B (zh) * | 2018-04-23 | 2021-01-26 | 南京明捷生物医药检测有限公司 | 一种测定多肽中活性诱导物质的方法 |
| SG11202102684VA (en) | 2018-09-18 | 2021-04-29 | 1 Globe Biomedical Co Ltd | Treatment for non-alcoholic fatty liver disease |
| US20210393623A1 (en) | 2018-09-26 | 2021-12-23 | Jacobio Pharmaceuticals Co., Ltd. | Novel Heterocyclic Derivatives Useful as SHP2 Inhibitors |
| KR20210110636A (ko) * | 2018-12-31 | 2021-09-08 | 더 보드 어브 트러스티스 어브 더 리랜드 스탠포드 주니어 유니버시티 | 미토콘드리아 기능이상을 치료하기 위한 방법 및 제형 |
| WO2020201263A1 (en) | 2019-04-01 | 2020-10-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment and prevention of cardiac remodeling |
| CN112441900B (zh) * | 2019-09-05 | 2024-07-23 | 浙江中科创越药业有限公司 | 4-联苯乙酸的制备方法 |
| CN111333486A (zh) * | 2020-04-08 | 2020-06-26 | 南京优氟医药科技有限公司 | 一种2-甲基-2-(4-氯苯基)-1,3-丙二醇的生产工艺 |
| AU2021275038A1 (en) | 2020-05-19 | 2022-12-22 | Kallyope, Inc. | AMPK activators |
| CN111423379B (zh) * | 2020-05-21 | 2021-08-03 | 湖南科技大学 | 取代3-吲唑类Mcl-1蛋白抑制剂及制备方法和应用 |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
| WO2022072397A1 (en) * | 2020-09-30 | 2022-04-07 | Bioverativ Therapeutics Inc. | Ampk activators and methods of use thereof |
| WO2025021039A1 (zh) * | 2023-07-21 | 2025-01-30 | 深圳众格生物科技有限公司 | Ampk激动剂及其用途 |
| WO2025045185A1 (zh) * | 2023-08-31 | 2025-03-06 | 深圳众格生物科技有限公司 | 芳基或杂芳基取代的氨基甲酸酯类化合物及其衍生物和用途 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999043654A2 (en) * | 1998-02-25 | 1999-09-02 | Genetics Institute, Inc. | Inhibitors of phospholipase enzymes |
| WO2003082271A2 (en) * | 2002-04-03 | 2003-10-09 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| WO2005014554A1 (en) * | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
| US20070129404A1 (en) * | 2003-10-15 | 2007-06-07 | Masahiko Hagihara | Novel indazole derivatives |
| EP1844771A2 (en) * | 2001-06-20 | 2007-10-17 | Wyeth | Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| WO2010064875A2 (en) * | 2008-12-05 | 2010-06-10 | Korea Institute Of Science And Technology | Novel indazole derivatives or pharmaceutically acceptable salts thereof as protein kinase inhibitors for proliferative diseases treatment, and a pharmaceutical composition containing the same as an active ingredient |
Family Cites Families (275)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010061B1 (en) | 1978-09-25 | 1983-07-13 | Stuart John Mc Farlane | Pharmaceutical preparations containing a mollusc extract |
| JP2602037B2 (ja) | 1987-10-31 | 1997-04-23 | 持田製薬株式会社 | 1−アシル−2,3−ジヒドロ−4(1h)−キノリノン−4−オキシム誘導体、その製法およびそれらを主成分とする利尿、降圧、抗浮腫および腹水除去用医薬組成物 |
| GB8814277D0 (en) | 1988-06-16 | 1988-07-20 | Glaxo Group Ltd | Chemical compounds |
| JPH02264757A (ja) | 1989-04-06 | 1990-10-29 | Nippon Steel Chem Co Ltd | ニトロインドール類の製造方法 |
| US5210092A (en) | 1990-09-25 | 1993-05-11 | Fujisawa Pharmaceutical Co., Ltd. | Angiotensin ii antagonizing heterocyclic derivatives |
| US5215994A (en) | 1990-09-25 | 1993-06-01 | Fujisawa Pharmaceutical Co., Ltd. | Angiotenin II antagonizing heterocyclic derivatives |
| US5354759A (en) | 1991-09-12 | 1994-10-11 | Fujisawa Pharmaceutical Co., Ltd. | Angiotenin II antagonizing heterocyclic compounds |
| WO1993006082A1 (en) | 1991-09-13 | 1993-04-01 | Merck & Co., Inc. | Process for the preparation of 4-substituted-1,4-dihydropyridines |
| DE4136489A1 (de) | 1991-11-06 | 1993-05-13 | Bayer Ag | Neue diethylentriamin-derivate und deren verwendung zu diagnostischen und therapeutischen zwecken |
| TW212798B (enExample) | 1991-11-25 | 1993-09-11 | Takeda Pharm Industry Co Ltd | |
| CA2083891A1 (en) | 1991-12-03 | 1993-06-04 | Angus Murray Macleod | Heterocyclic compounds, compositions containing them and their use in therapy |
| AU658729B2 (en) | 1992-03-27 | 1995-04-27 | Kyoto Pharmaceutical Industries, Ltd. | 3-(1H-imidazol-1-ylmethyl)-1H-indole derivatives |
| JP3229654B2 (ja) | 1992-06-05 | 2001-11-19 | ティーディーケイ株式会社 | 有機el素子用化合物および有機el素子 |
| US5616537A (en) | 1992-07-03 | 1997-04-01 | Kumiai Chemical Industry Co., Ltd. | Condensed heterocyclic derivatives and herbicides |
| GB2271991A (en) | 1992-11-02 | 1994-05-04 | Merck Sharp & Dohme | N-(2-oxo-1H-1,4-benzodiazepin-3-yl)-ureas |
| EP0639573A1 (de) | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
| US5354763A (en) | 1993-11-17 | 1994-10-11 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
| CA2183084A1 (en) | 1994-02-10 | 1995-08-17 | John Eugene Macor | 5-heteroarylindole derivatives |
| NZ290199A (en) | 1994-07-27 | 1999-06-29 | Sankyo Co | Nitrogen containing heterocyclic compounds, selective allosteric effectors to regulate m1 receptors |
| FR2723739B1 (fr) | 1994-08-19 | 1997-02-14 | Sanofi Sa | Derives de glycinamide, procedes pour leur preparation et medicaments les contenant. |
| JPH08225535A (ja) | 1994-11-15 | 1996-09-03 | Dai Ichi Seiyaku Co Ltd | インダゾール誘導体 |
| EP0717143A1 (de) | 1994-12-16 | 1996-06-19 | Lignozym GmbH | Mehrkomponentensystem zum Verändern, Abbau oder Bleichen von Lignin, ligninhaltigen Materialien oder ähnlichen Stoffen sowie Verfahren zu seiner Anwendung |
| EP0820441B1 (en) | 1995-04-10 | 2002-06-26 | Fujisawa Pharmaceutical Co., Ltd. | INDOLE DERIVATIVES AS cGMP-PDE INHIBITORS |
| WO1997010214A1 (en) | 1995-09-14 | 1997-03-20 | Shionogi & Co., Ltd. | Novel phenylacetic acid derivatives and medicinal composition containing the same |
| WO1997045425A1 (en) | 1996-05-27 | 1997-12-04 | Fujisawa Pharmaceutical Co., Ltd. | New indolyl and benzofuranyl carboxamides as inhibitors of nitric oxide production |
| US5629325A (en) | 1996-06-06 | 1997-05-13 | Abbott Laboratories | 3-pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission |
| US5861398A (en) | 1996-08-26 | 1999-01-19 | Alanex Corporation | Benzoperimidine-carboxylic acids and derivatives thereof |
| WO1998028292A1 (en) | 1996-12-23 | 1998-07-02 | Smithkline Beecham Corporation | Novel piperidine containing compounds |
| CA2282593A1 (en) | 1997-03-31 | 1998-10-08 | Du Pont Pharmaceuticals Company | Indazoles of cyclic ureas useful as hiv protease inhibitors |
| EP0901786B1 (en) | 1997-08-11 | 2007-06-13 | Pfizer Products Inc. | Solid pharmaceutical dispersions with enhanced bioavailability |
| SE9704545D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| SE9704544D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| DE69918799D1 (de) | 1998-01-14 | 2004-08-26 | Uab Res Foundation Birmingham | Verfahren zur herstellung und screening von inhibitoren des bakteriellen nad synthetase enzyms, verbindungen daraus und methoden zur behandlung bakterieller und mikrobieller infektionen mit diesen inhibitoren |
| CA2260499A1 (en) | 1998-01-29 | 1999-07-29 | Sumitomo Pharmaceuticals Company Limited | Pharmaceutical compositions for the treatment of ischemic brain damage |
| JP2002515488A (ja) | 1998-05-15 | 2002-05-28 | ギルフォード ファーマシューティカルズ インコーポレイテッド | カルボキサミド化合物、組成物、及びparp活性の抑制方法 |
| AU4981199A (en) | 1998-07-08 | 2000-02-01 | Gregory N. Beatch | Compositions and methods for modulating sexual activity |
| HRP20010030A2 (en) | 1998-07-15 | 2001-12-31 | Teijin Ltd | Thiobenzimidazole derivatives |
| DE19842354A1 (de) | 1998-09-16 | 2000-03-23 | Bayer Ag | Isothiazolcarbonsäureamide |
| FR2783520B1 (fr) | 1998-09-21 | 2000-11-10 | Oreal | Nouveaux 4-hydroxyindoles cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procede de teinture |
| WO2000028993A1 (en) | 1998-11-19 | 2000-05-25 | Nortran Pharmaceuticals, Inc. | Serotonin ligands as pro-erectile compounds |
| AR021509A1 (es) | 1998-12-08 | 2002-07-24 | Lundbeck & Co As H | Derivados de benzofurano, su preparacion y uso |
| CZ27399A3 (cs) | 1999-01-26 | 2000-08-16 | Ústav Experimentální Botaniky Av Čr | Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv |
| WO2001032621A1 (en) | 1999-10-29 | 2001-05-10 | Wakunaga Pharmaceutical Co., Ltd. | Novel indole derivatives and drugs containing the same as the active ingredient |
| CN1105722C (zh) | 1999-11-12 | 2003-04-16 | 中国科学院上海药物研究所 | 含氮杂环基的青蒿素衍生物及其制备方法 |
| MXPA02011376A (es) | 2000-05-22 | 2004-02-26 | Leo Pharma As | Benzofenonas como inhibidores de il-1beta y tnf-alfa. |
| US6995268B2 (en) | 2000-06-20 | 2006-02-07 | Wayne State University | N- and O-substituted 4-[2-(diphenylmethoxy)-ethyl]-1- (phenyl) methyl) piperidine analogs and methods of treating CNS disorders therewith |
| JP2002017387A (ja) | 2000-07-06 | 2002-01-22 | Mitsubishi Rayon Co Ltd | インドール誘導体の製造法 |
| JP2002017386A (ja) | 2000-07-06 | 2002-01-22 | Mitsubishi Rayon Co Ltd | インドール−3−カルボン酸誘導体の製造法 |
| WO2002018363A2 (en) | 2000-08-29 | 2002-03-07 | Abbott Laboratories | 3-phenyl-propanoic acid derivatives as protein tyrosine phosphatase inhibitors |
| DE10046934A1 (de) | 2000-09-21 | 2002-04-18 | Consortium Elektrochem Ind | Verfahren zur fermentativen Herstellung von nicht-proteinogenen L-Aminosäuren |
| WO2002034744A1 (en) | 2000-10-25 | 2002-05-02 | Astrazeneca Ab | Quinazoline derivatives |
| HUP0302718A3 (en) | 2000-11-01 | 2011-03-28 | Merck Patent Gmbh | Methods and compositions for the treatment of diseases of the eye |
| WO2002040481A2 (en) | 2000-11-20 | 2002-05-23 | Millennium Pharmaceuticals, Inc. | Adenine based inhibitors of adenylyl cyclase, pharmaceutical compositions and method of use thereof |
| US6387992B1 (en) | 2000-11-27 | 2002-05-14 | Ciba Specialty Chemicals Corporation | Substituted 5-heteroaryl-2-(2-hydroxyphenyl)-2h-benzotriazole UV absorbers, a process for preparation thereof and compositions stabilized therewith |
| GB0031315D0 (en) | 2000-12-21 | 2001-02-07 | Glaxo Group Ltd | Indole derivatives |
| US20040087620A1 (en) | 2001-01-18 | 2004-05-06 | Tatsuo Tsuri | Terphenyl compounds bearing substituted amino groups |
| WO2002057237A1 (en) | 2001-01-22 | 2002-07-25 | Shionogi & Co., Ltd. | Hetero-tricyclic compounds having substituted amino groups |
| AU2002303084B2 (en) | 2001-02-02 | 2006-05-25 | Pharmacopiea, Inc. | 3,4-di-substituted cyclobutene-1, 2 -diones as CXC chemokine receptor antagonists |
| JP4104983B2 (ja) | 2001-02-28 | 2008-06-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン−4受容体作動薬としてのアシル化ピペリジン誘導体 |
| WO2002072549A1 (en) | 2001-03-12 | 2002-09-19 | Millennium Pharmaceuticals, Inc. | Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor |
| GB0106586D0 (en) | 2001-03-16 | 2001-05-09 | Smithkline Beecham Plc | Novel compounds |
| CA2444031C (en) | 2001-04-16 | 2012-02-21 | Schering Corporation | 3,4-di-substituted cyclobutene-1,2-diones as cxc-chemokine receptor ligands |
| JPWO2002100833A1 (ja) | 2001-06-12 | 2004-09-24 | 住友製薬株式会社 | Rhoキナーゼ阻害剤 |
| PL366624A1 (en) | 2001-07-05 | 2005-02-07 | Synaptic Pharmaceutical Corporation | Substituted anilinic piperidines as mch selective antagonists |
| DK1411926T3 (da) | 2001-08-01 | 2005-08-29 | Merck Patent Gmbh | Integrininhibitorer til behandling af öjensygdomme |
| EP1424336A4 (en) | 2001-09-03 | 2004-11-10 | Takeda Chemical Industries Ltd | 1,3-BENZOTHIAZINE DERIVATIVES AND THEIR USE |
| EP1434775A1 (en) | 2001-10-12 | 2004-07-07 | Schering Corporation | 3,4-di-substituted maleimide compounds as cxc-chemokine receptor antagonists |
| FR2831536A1 (fr) | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
| CA2464333C (en) | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| EP1441725A1 (en) | 2001-10-26 | 2004-08-04 | Aventis Pharmaceuticals Inc. | Benzimidazoles and analogues and their use as protein kinases inhibitors |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| TWI317634B (en) | 2001-12-13 | 2009-12-01 | Nat Health Research Institutes | Aroyl indoles compounds |
| SE0104331D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Novel compounds |
| JP2003192716A (ja) | 2001-12-27 | 2003-07-09 | Mitsui Chemicals Inc | オレフィン重合用触媒および該触媒を用いたオレフィンの重合方法 |
| CA2477208C (en) | 2002-02-21 | 2010-11-30 | Asahi Kasei Pharma Corporation | Substituted phenylalkanoic acid derivatives and use thereof |
| EP1478437B1 (en) | 2002-02-27 | 2005-08-31 | Pfizer Products Inc. | Acc inhibitors |
| JP2005530804A (ja) | 2002-05-14 | 2005-10-13 | ベイラー カレッジ オブ メディスン | Her2発現の小分子阻害剤 |
| AU2003239508A1 (en) | 2002-05-21 | 2003-12-12 | Bristol-Myers Squibb Company | Indole compounds useful as impdh inhibitors |
| US20050261164A1 (en) | 2002-07-09 | 2005-11-24 | Fujisawa Pharmaceutical Co., Ltd. | Remedy for urinary frequency and urinary incontinence |
| US6972336B2 (en) | 2002-07-18 | 2005-12-06 | Novartis Ag | N-alkylation of indole derivatives |
| JP2006502133A (ja) | 2002-08-10 | 2006-01-19 | アステックス、セラピューティックス、リミテッド | サイクリン依存キナーゼ(cdk)インヒビターとしての3−(カルボニル)1h−インダゾール化合物 |
| FR2845382A1 (fr) | 2002-10-02 | 2004-04-09 | Sanofi Synthelabo | Derives d'indazolecarboxamides, leur preparation et leur utilisation en therapeutique |
| FR2846656B1 (fr) | 2002-11-05 | 2004-12-24 | Servier Lab | Nouveaux derives d'imidazopyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP2316831B1 (en) | 2002-11-21 | 2013-03-06 | Novartis AG | 2-(morpholin-4-yl)pyrimidines as phosphotidylinositol (PI) 3-kinase inhibitors and their use in the treatment of cancer |
| IS7839A (is) | 2002-11-22 | 2004-05-23 | Merck Frosst Canada Ltd. | 4-oxó-1-(3-setið fenýl-1,4-díhýdró-1,8-naftýridín-3-karboxamíð fosfódíesterasa-4 hindrar |
| BRPI0318799B8 (pt) | 2002-11-28 | 2021-05-25 | Suven Life Sciences Ltd | processo para a preparação de um composto |
| AU2003303681A1 (en) | 2003-01-06 | 2004-08-10 | Eli Lilly And Company | Fused heterocyclic derivates as ppar modulators |
| EP1585726A1 (en) | 2003-01-06 | 2005-10-19 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
| CL2004000234A1 (es) | 2003-02-12 | 2005-04-15 | Biogen Idec Inc | Compuestos derivados 3-(piridin-2-il)-4-heteroaril-pirazol sustituidos, antagonistas de aik5 y/o aik4; composicion farmaceutica y uso del compuesto en el tratamiento de desordenes fibroticos como esclerodermia, lupus nefritico, cicatrizacion de herid |
| ITMI20030287A1 (it) | 2003-02-18 | 2004-08-19 | Acraf | Indazolammidi dotate di attivita' analgesica metodo, per |
| JP4472691B2 (ja) | 2003-02-21 | 2010-06-02 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | 神経変性疾患の処置のための1−フェニルアルカンカルボン酸誘導体 |
| JP2004284998A (ja) | 2003-03-24 | 2004-10-14 | Taoka Chem Co Ltd | 1−アルキルインドール類の製造方法 |
| JP2004284997A (ja) | 2003-03-24 | 2004-10-14 | Taoka Chem Co Ltd | 高純度インドールカルボン酸類の製造方法 |
| EP1615697A2 (en) | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | New pyrazolo[1,5-a] pyrimidine derivatives and pharmaceutical use thereof |
| WO2004089415A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | COMBINATIONS OF AN 11β-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITOR AND A GLUCOCORTICOID RECEPTOR AGONIST |
| JP4629657B2 (ja) | 2003-04-11 | 2011-02-09 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | 11β−ヒドロキシステロイドデヒドロゲナーゼ1型化活性化合物 |
| WO2004089416A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Combination of an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent |
| ATE455547T1 (de) | 2003-04-11 | 2010-02-15 | High Point Pharmaceuticals Llc | Pharmazeutische verwendungen von kondensierten 1, 2,4-triazolen |
| EP1615637A1 (en) | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | Pharmaceutical use of substituted 1,2,4-triazoles |
| EP1628970A2 (en) | 2003-04-30 | 2006-03-01 | The Institutes of Pharmaceutical Discovery, LLC | Heterocycle substituted carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
| US7119205B2 (en) | 2003-05-16 | 2006-10-10 | Abbott Laboratories | Thienopyridones as AMPK activators for the treatment of diabetes and obesity |
| US7429596B2 (en) | 2003-06-20 | 2008-09-30 | The Regents Of The University Of California | 1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use thereof |
| JP2009513513A (ja) | 2003-07-04 | 2009-04-02 | グラクソスミスクライン・ソシエタ・ペル・アチオニ | Orl−1受容体リガンドとしての置換インドール |
| CA2535665A1 (en) | 2003-08-14 | 2005-02-24 | Asahi Kasei Pharma Corporation | Substituted arylalkanoic acid derivative and use thereof |
| JP4458819B2 (ja) | 2003-11-13 | 2010-04-28 | 株式会社リコー | アゾ置換インドール化合物及びこれを用いた光記録媒体 |
| 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 |
| WO2005063767A2 (en) | 2003-12-22 | 2005-07-14 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| US20050234095A1 (en) | 2004-03-25 | 2005-10-20 | Wenge Xie | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| WO2005097203A2 (en) | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Serum protein conjugates of ion channel modulating compounds and uses thereof |
| JP4510500B2 (ja) | 2004-04-15 | 2010-07-21 | 株式会社リコー | アゾ置換インドール化合物及びアゾ金属キレート化合物、並びに光記録媒体 |
| US7632831B2 (en) | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| ES2327857T3 (es) | 2004-05-12 | 2009-11-04 | Pfizer Products Inc. | Derivados de prolina y su uso como inhibidores de la dipeptidil peptidasa iv. |
| BRPI0510273A (pt) | 2004-05-25 | 2007-10-30 | Pfizer Prod Inc | derivados de tetraazabenzo[e]azuleno e análogos destes |
| WO2005121137A1 (en) | 2004-06-03 | 2005-12-22 | Brandeis University | Asymmetric michael and aldol addition using bifunctional cinchona-alkaloid-based catalysts |
| DE602005009209D1 (de) | 2004-06-18 | 2008-10-02 | Biolipox Ab | Zur behandlung von entzündungen geeignete indole |
| US20080146616A1 (en) | 2004-06-18 | 2008-06-19 | Kristofer Olofsson | Indoles Useful in the Treatment of Inflammation |
| US20080146811A1 (en) | 2004-07-23 | 2008-06-19 | Hongfeng Deng | Compounds and Methods For Treatment of Thrombosis |
| US8193205B2 (en) | 2004-07-28 | 2012-06-05 | Janssen Pharmaceutica N.V. | Substituted indolyl alkyl amino derivatives as novel inhibitors of histone deacetylase |
| US20070015771A1 (en) | 2004-07-29 | 2007-01-18 | Threshold Pharmaceuticals, Inc. | Lonidamine analogs |
| JP2006045119A (ja) | 2004-08-04 | 2006-02-16 | Toray Ind Inc | ピラジン誘導体及びそれを有効成分とする腎炎治療薬 |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| CA2580767A1 (en) | 2004-09-17 | 2006-03-30 | Whitehead Institute For Biomedical Research | Compounds, compositions and methods of inhibiting alpha-synuclein toxicity |
| WO2006038606A1 (ja) | 2004-10-05 | 2006-04-13 | Shionogi & Co., Ltd. | ビアリール誘導体 |
| WO2006044509A2 (en) | 2004-10-15 | 2006-04-27 | Biogen Idec Ma Inc. | Methods of treating vascular injuries |
| JP2006131519A (ja) | 2004-11-04 | 2006-05-25 | Idemitsu Kosan Co Ltd | 縮合環含有化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
| DE102004054666A1 (de) | 2004-11-12 | 2006-05-18 | Bayer Cropscience Gmbh | Substituierte Pyrazol-3-carboxamide, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| TW200626130A (en) | 2004-11-15 | 2006-08-01 | Shionogi & Co | 5-membered heterocycle derivatives |
| RU2418797C2 (ru) | 2004-12-22 | 2011-05-20 | Мемори Фармасьютиклз Корпорейшн | Лиганды никотинового рецептора альфа-7, их получение и применение |
| EP1844023A1 (en) | 2004-12-31 | 2007-10-17 | Sk Chemicals Co., Ltd. | Quinazoline derivatives for the treatment and prevention of diabetes and obesity |
| PA8660701A1 (es) | 2005-02-04 | 2006-09-22 | Pfizer Prod Inc | Agonistas de pyy y sus usos |
| FR2882054B1 (fr) | 2005-02-17 | 2007-04-13 | Sanofi Aventis Sa | Derives de 1,5-diarylpyrrole, leur preparation et leur application en therapeutique |
| CN101213191B (zh) | 2005-03-30 | 2011-08-24 | (株)大熊制药 | 抗真菌三唑衍生物 |
| WO2006110516A1 (en) | 2005-04-11 | 2006-10-19 | Abbott Laboratories | Acylhydrazide p2x7 antagonists and uses thereof |
| WO2006115188A1 (ja) | 2005-04-22 | 2006-11-02 | Daiichi Sankyo Company, Limited | ヘテロ環化合物 |
| WO2006125119A1 (en) | 2005-05-17 | 2006-11-23 | Sarcode Corporation | Compositions and methods for treatment of eye disorders |
| WO2006130453A1 (en) | 2005-05-27 | 2006-12-07 | Brandeis University | Asymmetric aldol additions using bifunctional cinchona-alkaloid-based catalysts |
| WO2006130437A2 (en) | 2005-05-27 | 2006-12-07 | Brandeis University | Asymmetric carbon-carbon-bond-forming reactions catalyzed by bifunctional cinchona alkaloids |
| ATE530519T1 (de) | 2005-06-03 | 2011-11-15 | Abbott Lab | Cyclobutylaminderivate |
| WO2006133559A1 (en) | 2005-06-14 | 2006-12-21 | Merck Frosst Canada Ltd. | Reversible inhibitors of monoamine oxidase a and b |
| WO2007002461A1 (en) | 2005-06-23 | 2007-01-04 | Dr. Reddy's Laboratories Ltd. | 3,4-substituted thiazoles as ampk activators |
| RS50821B (sr) | 2005-06-27 | 2010-08-31 | Sanofi-Aventis | Derivati pirazolopiridina kao inhibitori beta-adrenergičnog receptora kinaze 1 |
| JP2009500351A (ja) | 2005-07-04 | 2009-01-08 | ドクター レディズ ラボラトリーズ リミテッド | Ampkアクチベータとしてのチアゾール誘導体 |
| JP2007015952A (ja) | 2005-07-06 | 2007-01-25 | Shionogi & Co Ltd | ナフタレン誘導体 |
| EP1754483A1 (en) | 2005-08-18 | 2007-02-21 | Merck Sante | Use of thienopyridone derivatives as AMPK activators and pharmaceutical compositions containing them |
| EP1931632A4 (en) | 2005-08-18 | 2011-05-11 | Microbia Inc | USEFUL INDOOR CONNECTIONS |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| WO2007056281A2 (en) | 2005-11-03 | 2007-05-18 | Ilypsa, Inc. | Multivalent indole compounds and use thereof as phospholipase-a2 inhibitors |
| AU2006311851A1 (en) | 2005-11-03 | 2007-05-18 | Ilypsa, Inc. | Azaindole compounds and use thereof as phospholipase-A2 inhibitors |
| WO2007056279A2 (en) | 2005-11-03 | 2007-05-18 | Ilypsa, Inc. | Phospholipase inhibitors, including multi-valent phospholipase inhibitors, and use thereof, including as lumen-localized phospholipase inhibitors |
| US7932248B2 (en) | 2005-11-09 | 2011-04-26 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| WO2007058504A1 (en) | 2005-11-21 | 2007-05-24 | Lg Life Sciences, Ltd. | Novel compounds as agonist for ppar gamma and ppar alpha, method for preparation of the same, and pharmaceutical composition containing the same |
| CN1978445B (zh) | 2005-12-02 | 2010-09-01 | 中国科学院上海药物研究所 | 一种可用作人源腺苷单核苷酸激活蛋白激酶激活剂的化合物及其制备方法和应用 |
| US8163749B2 (en) | 2005-12-14 | 2012-04-24 | Bristol-Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| NZ568595A (en) | 2005-12-14 | 2010-04-30 | Bristol Myers Squibb Co | Arylpropionamide, arylacrylamide, arylpropynamide, or arylmethylurea analogs as factor Xla inhibitors |
| WO2007079173A2 (en) | 2005-12-30 | 2007-07-12 | Emergent Biosolutions Inc. | Novel 2-heteroaryloxy-phenol derivatives as antibacterial agents |
| EP1984360B1 (en) | 2006-02-03 | 2014-01-15 | Eli Lilly & Company | Compounds and methods for modulating FX-receptors |
| GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2006271A4 (en) | 2006-03-30 | 2011-08-10 | Asahi Kasei Pharma Corp | SUBSTITUTED BICYCLIC CYCLIC DERIVATIVE AND USE THEREOF |
| US8008481B2 (en) | 2006-03-31 | 2011-08-30 | Ericsson Anna M | Indazole compounds |
| RU2450006C2 (ru) | 2006-04-18 | 2012-05-10 | Эбботт Лэборетриз | Антагонисты ванилоидного рецептора подтипа 1(vr1) и их применение |
| NL2000581C2 (nl) | 2006-04-20 | 2008-01-03 | Pfizer Prod Inc | Aangecondenseerde fenylamidoheterocyclische verbindingen. |
| AU2007253950B2 (en) | 2006-05-19 | 2012-05-03 | Abbott Laboratories | CNS active fused bicycloheterocycle substituted azabicyclic alkane derivatives |
| PL2029547T3 (pl) | 2006-05-24 | 2010-09-30 | Lilly Co Eli | Agoniści FXR |
| CA2653424A1 (en) | 2006-06-08 | 2007-12-13 | Ube Industries, Ltd. | Novel indazole derivative having spiro ring structure in side chain |
| EP2046741B1 (en) | 2006-07-03 | 2012-10-31 | Proximagen Ltd. | Indoles as 5-ht6 modulators |
| FR2903695B1 (fr) | 2006-07-13 | 2008-10-24 | Merck Sante Soc Par Actions Si | Utilisation de derives d'imidazole activateurs de l'ampk, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| KR100826108B1 (ko) | 2006-08-04 | 2008-04-29 | 한국화학연구원 | 퓨란-2-카복실산 유도체 및 그의 제조 방법 |
| WO2008019357A2 (en) | 2006-08-07 | 2008-02-14 | Ironwood Pharmaceuticals, Inc. | Indole compounds |
| JP2008063278A (ja) | 2006-09-07 | 2008-03-21 | Fujifilm Finechemicals Co Ltd | 1−ピリジン−4−イル−インドール類の製造方法 |
| JP2008106037A (ja) | 2006-09-29 | 2008-05-08 | Osaka Prefecture Univ | インドール化合物の製造方法およびインドール化合物 |
| WO2008054748A2 (en) | 2006-10-31 | 2008-05-08 | Arena Pharmaceuticals, Inc. | Indazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| EP2097420B1 (en) | 2006-11-29 | 2012-04-04 | Pfizer Products Inc. | Spiroketone inhibitors of acetyl-coa carboxylase |
| KR20090127867A (ko) | 2006-12-05 | 2009-12-14 | 네이셔널 치아오 텅 유니버시티 | 인다졸 화합물 |
| WO2008072850A1 (en) | 2006-12-11 | 2008-06-19 | Amorepacific Corporation | Triazine derivatives having inhibitory activity against acetyl-coa carboxylase |
| CL2007003609A1 (es) | 2006-12-14 | 2008-07-25 | Bayer Schering Pharma Ag | Compuestos derivados de dihidropiridinas sustituidas; proceso de preparacion; compuestos intermediarios; composicion farmaceutica; proceso para producir la composicion farmaceutica; y uso en el tratamiento de una enfermedad mejorada con la inhibicion |
| CA2672205A1 (en) | 2006-12-18 | 2008-06-26 | Ambrx, Inc. | Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides |
| EA200900798A1 (ru) | 2006-12-22 | 2010-10-29 | Новартис Аг | Производные индол-4-илпиримидинил-2-иламина и их применение в качестве ингибиторов циклинзависимой киназы |
| EP2079694B1 (en) | 2006-12-28 | 2017-03-01 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| PE20081559A1 (es) | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| EP2120952A4 (en) | 2007-01-15 | 2011-09-21 | Us Of America As Represented By The Secretary Of The Army On Behalf Of The U S Army Res Inst Of Infe | ANTIVIRAL COMPOUNDS AND METHODS OF USE |
| DE102007002717A1 (de) | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Heterocyclische Indazolderivate |
| JP2008179567A (ja) | 2007-01-25 | 2008-08-07 | Toray Ind Inc | ピラジン誘導体を有効成分とする抗がん剤 |
| AR065093A1 (es) | 2007-02-05 | 2009-05-13 | Merck Frosst Canada Ltd | Compuestos farmacéuticos inhibidores de la biosintesis de leucotrienos |
| JP2010518125A (ja) | 2007-02-12 | 2010-05-27 | インターミューン・インコーポレーテッド | C型肝炎ウイルス複製の新規な阻害剤 |
| JP5107589B2 (ja) | 2007-02-13 | 2012-12-26 | 旭化成株式会社 | インドール誘導体 |
| JP2008208074A (ja) | 2007-02-27 | 2008-09-11 | Toray Ind Inc | ピラジン誘導体を有効成分とする抗がん剤 |
| JP2008222576A (ja) | 2007-03-09 | 2008-09-25 | Japan Enviro Chemicals Ltd | インドール化合物の製造方法 |
| WO2008110863A1 (en) | 2007-03-15 | 2008-09-18 | Glenmark Pharmaceuticals S.A. | Indazole derivatives and their use as vanilloid receptor ligands |
| WO2008118822A1 (en) | 2007-03-23 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US20100152210A1 (en) | 2007-03-28 | 2010-06-17 | Neuro Search A/S/ | Purinyl derivatives and their use as potassium channel modulators |
| WO2008136642A1 (en) | 2007-05-07 | 2008-11-13 | Mazence Inc. | Naphthoquinone-based pharmaceutical composition for treatment or prevention of diseases involving obesity, diabetes, metabolic syndrome, neuro-degenerative diseases and mitochondria dysfunction diseases |
| WO2008150899A1 (en) | 2007-05-29 | 2008-12-11 | Emory University | Combination therapies for treatment of cancer and inflammatory diseases |
| FR2917735B1 (fr) | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
| TW200906823A (en) | 2007-07-16 | 2009-02-16 | Lilly Co Eli | Compounds and methods for modulating FXR |
| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| AR067770A1 (es) | 2007-08-03 | 2009-10-21 | Betagenon Ab | Derivados de tiazol y ditiazol para el tratamiento de diabetes |
| KR20090016804A (ko) | 2007-08-13 | 2009-02-18 | 주식회사 티지 바이오텍 | 신규 벤질에스테르계 화합물 및 이를 유효성분으로함유하는 비만, 당뇨 및 고지혈증의 예방 및 치료용 조성물 |
| WO2009026107A1 (en) | 2007-08-17 | 2009-02-26 | Portola Pharmaceuticals, Inc. | Protein kinase inhibitors |
| CN101821252A (zh) | 2007-08-29 | 2010-09-01 | 先灵公司 | 取代的吲哚衍生物及其使用方法 |
| TW200924751A (en) | 2007-08-29 | 2009-06-16 | Schering Corp | 2,3-substituted indole derivatives and methods of use thereof |
| EP2203436A1 (en) | 2007-09-17 | 2010-07-07 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| EP2215075B1 (en) | 2007-10-26 | 2013-12-11 | Janssen Pharmaceutica, N.V. | Quinolinone derivatives as parp inhibitors |
| US20090124680A1 (en) | 2007-10-31 | 2009-05-14 | Mazence Inc. | Use of prodrug composition containing naphthoquinone-based compound for manufacture of medicament for treatment or prevention of diseases involving metabolic syndrome |
| MX2010005355A (es) | 2007-11-16 | 2010-06-02 | Schering Corp | Derivados de indol sustituidos con 3-aminosulfonilo y metodos de uso de los mismos. |
| KR101573091B1 (ko) | 2007-11-16 | 2015-11-30 | 리겔 파마슈티칼스, 인크. | 대사성 장애를 위한 카르복스아미드, 술폰아미드 및 아민 화합물 |
| EP2226315A4 (en) | 2007-12-28 | 2012-01-25 | Carna Biosciences Inc | 2-aminoquinazoline DERIVATIVE |
| JP5339565B2 (ja) | 2008-01-31 | 2013-11-13 | 国立大学法人横浜国立大学 | 流体機械 |
| NZ587165A (en) | 2008-02-04 | 2012-03-30 | Mercury Therapeutics Inc | Ampk modulators |
| WO2009115874A2 (en) | 2008-03-17 | 2009-09-24 | Matrix Laboratories Ltd. | Novel heterocyclic compounds, pharmaceutical compositions containing them and processes for their preparation |
| US20110021556A1 (en) | 2008-03-20 | 2011-01-27 | Hoffman-La Roche, Inc. | Pyrrolidinyl derivatives and uses thereof |
| WO2009120783A1 (en) | 2008-03-25 | 2009-10-01 | The Johns Hopkins University | High affinity inhibitors of hepatitis c virus ns3/4a protease |
| ES2395347T3 (es) | 2008-03-27 | 2013-02-12 | Janssen Pharmaceutica, N.V. | Derivados de indolilalquilamino sustituidos con aza-biciclohexilo como inhibidores novedosos de histona desacetilasa |
| UA103321C2 (ru) | 2008-04-11 | 2013-10-10 | Мерк Патент Гмбх | Производные тиенопиридона как активаторы amp-активированной протеинкиназы (амрк) |
| CA2722139C (en) | 2008-04-23 | 2017-04-11 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
| MY160357A (en) | 2008-05-05 | 2017-02-28 | Merck Patent Gmbh | Thienopyridone derivatives as amp-activated protein kinase (ampk) activators |
| GB0808282D0 (en) | 2008-05-07 | 2008-06-11 | Medical Res Council | Compounds for use in stabilizing p53 mutants |
| EP2297164A1 (en) | 2008-05-28 | 2011-03-23 | Pfizer Inc. | Pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| EP2297163B1 (en) | 2008-05-28 | 2015-07-08 | Pfizer Inc. | Pyrazolospiroketone acetyl-CoA carboxylase inhibitors |
| WO2009152909A1 (en) | 2008-06-16 | 2009-12-23 | Merck Patent Gmbh | Quinoxalinedione derivatives |
| AR072184A1 (es) | 2008-06-20 | 2010-08-11 | Glaxo Group Ltd | Derivados de oxadiazol como agonistas del receptor s1p1 |
| DE102008031480A1 (de) | 2008-07-03 | 2010-01-07 | Merck Patent Gmbh | Salze enthaltend ein Pyrimidincarbonsäure-Derivat |
| JP2011528363A (ja) | 2008-07-16 | 2011-11-17 | キング・ファーマシューティカルズ・リサーチ・アンド・デベロプメント・インコーポレイティッド | アテローム性動脈硬化症の治療 |
| WO2010010186A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | Novel compounds useful for the treatment of degenerative and inflammatory diseases |
| WO2010013161A1 (en) | 2008-07-29 | 2010-02-04 | Pfizer Inc. | Fluorinated heteroaryls |
| ATE540040T1 (de) | 2008-08-28 | 2012-01-15 | Pfizer | Dioxabicycloä3.2.1üoctan-2,3,4-triolderivate |
| WO2010036910A1 (en) | 2008-09-26 | 2010-04-01 | Yoshikazu Ohta | Heart protection by administering an amp-activated protein kinase activator |
| KR20110061640A (ko) | 2008-09-26 | 2011-06-09 | 에프. 호프만-라 로슈 아게 | Hcv 치료용 피린 또는 피라진 유도체 |
| US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| JP2012507530A (ja) | 2008-10-29 | 2012-03-29 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病剤である新規な環状ベンズイミダゾール誘導体 |
| EP2362731B1 (en) | 2008-10-31 | 2016-04-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010056041A2 (ko) | 2008-11-13 | 2010-05-20 | 주식회사 머젠스 | 허혈 또는 허혈 재관류에 의해 유발되는 심장질환의 치료 및 예방을 위한 약제 조성물 |
| WO2010058858A1 (ja) | 2008-11-21 | 2010-05-27 | ラクオリア創薬株式会社 | 5-ht2b受容体拮抗活性を有する新規ピラゾール-3-カルボキサミド誘導体 |
| US20110237633A1 (en) | 2008-12-11 | 2011-09-29 | Bijoy Panicker | Small molecule modulators of hepatocyte growth factor (scatter factor) activity |
| US8741923B2 (en) | 2008-12-18 | 2014-06-03 | Merck Serono Sa | Oxadiazole fused heterocyclic derivatives useful for the treatment of multiple sclerosis |
| WO2010073011A2 (en) | 2008-12-23 | 2010-07-01 | Betagenon Ab | Compounds useful as medicaments |
| CA2772760A1 (en) | 2008-12-23 | 2010-07-01 | President And Fellows Of Harvard College | Small molecule inhibitors of necroptosis |
| NZ594556A (en) | 2009-01-28 | 2013-11-29 | Rigel Pharmaceuticals Inc | Carboxamide compounds and methods for using the same |
| WO2010086613A1 (en) | 2009-01-30 | 2010-08-05 | Betagenon Ab | Compounds useful as inhibitors as ampk |
| WO2010086820A1 (en) | 2009-02-02 | 2010-08-05 | Pfizer Inc. | 4-amino-5-oxo-7, 8-dihydropyrimido [5,4-f] [1,4] oxazepin-6 (5h) -yl) phenyl derivatives, pharmaceutical compositions and uses thereof |
| US20100210682A1 (en) | 2009-02-19 | 2010-08-19 | Abbott Laboratories | Repeated Dosing of TRPV1 Antagonists |
| EP2406230A1 (en) | 2009-03-11 | 2012-01-18 | Pfizer Inc. | Substituted indazole amides and their use as glucokinase activators |
| UA99882C2 (uk) | 2009-03-11 | 2012-10-10 | Пфайзер Інк. | Похідні бензофуранілу, фармацевтична композиція та спосіб лікування захворювань (варіанти) |
| WO2010106457A2 (en) | 2009-03-20 | 2010-09-23 | Pfizer Inc. | 3-oxa-7-azabicyclo[3.3.1]nonanes |
| CA2750353C (en) | 2009-03-24 | 2016-08-16 | Sumitomo Chemical Company, Limited | Method for manufacturing a boronic acid ester compound |
| BRPI1013392A2 (pt) | 2009-03-31 | 2016-03-29 | Renascience Co Ltd | inibidor do inibidor-1 do ativador do plasminogênio |
| WO2010118009A1 (en) | 2009-04-06 | 2010-10-14 | Ptc Therapeutics, Inc. | Hcv inhibitor and therapeutic agent combinations |
| EP2427448A1 (en) | 2009-05-08 | 2012-03-14 | Pfizer Inc. | Gpr 119 modulators |
| WO2010128425A1 (en) | 2009-05-08 | 2010-11-11 | Pfizer Inc. | Gpr 119 modulators |
| NZ596467A (en) | 2009-06-05 | 2014-01-31 | Pfizer | L- ( piperidin-4-yl) -pyrazole derivatives as gpr 119 modulators |
| ES2567753T3 (es) | 2009-07-08 | 2016-04-26 | Baltic Bio Ab | Derivados de 1,2,4-tiazolidin-3-ona y su uso en el tratamiento del cáncer |
| WO2011005611A1 (en) | 2009-07-09 | 2011-01-13 | Merck Sharp & Dohme Corp. | Neuromedin u receptor agonists and uses thereof |
| US8742100B2 (en) | 2009-07-30 | 2014-06-03 | National University Of Singapore | Small molecule inhibitors of isoprenylcysteine carboxyl methyltransferase with potential anticancer activity |
| GB0915892D0 (en) | 2009-09-10 | 2009-10-14 | Smithkline Beecham Corp | Compounds |
| WO2011032320A1 (en) | 2009-09-21 | 2011-03-24 | F. Hoffmann-La Roche Ag | Novel alkene oxindole derivatives |
| WO2011069298A1 (en) | 2009-12-11 | 2011-06-16 | F. Hoffmann-La Roche Ag | Novel cyclopropane indolinone derivatives |
| JP2013047189A (ja) | 2009-12-25 | 2013-03-07 | Kyorin Pharmaceutical Co Ltd | 新規パラバン酸誘導体及びそれらを有効成分とする医薬 |
| HRP20140035T1 (hr) | 2009-12-29 | 2014-02-14 | Poxel | Tieno[2,3-b]piridindion aktivatori ampk i njihove terapijske uporabe |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| WO2011123681A1 (en) | 2010-03-31 | 2011-10-06 | Rigel Pharmaceuticals, Inc. | Methods for using carboxamide, sulfonamide and amine compounds |
| US8344137B2 (en) | 2010-04-14 | 2013-01-01 | Hoffman-La Roche Inc. | 3,3-dimethyl tetrahydroquinoline derivatives |
| EP2566868A1 (en) | 2010-05-05 | 2013-03-13 | GlaxoSmithKline LLC | Pyrrolo [3, 2 -d]pyrimidin-3 -yl derivatives used as activators of ampk |
| US8592594B2 (en) | 2010-07-02 | 2013-11-26 | Hoffmann-La Roche Inc. | Tetrahydro-quinoline derivatives |
| CA2806341C (en) | 2010-07-29 | 2020-03-24 | Rigel Pharmaceuticals, Inc. | Ampk-activating heterocyclic compounds and methods for using the same |
| KR101190141B1 (ko) | 2010-08-24 | 2012-10-12 | 서울대학교산학협력단 | Ampk를 활성화시키는 화합물을 함유하는 약학조성물 |
| JP2013230986A (ja) | 2010-08-25 | 2013-11-14 | Kyorin Pharmaceutical Co Ltd | 新規ヒダントイン誘導体及びそれらを有効成分とする医薬 |
| WO2012027548A1 (en) | 2010-08-25 | 2012-03-01 | The Feinstein Institute For Medical Research | Compounds and methods for prevention and treatment of alzheimer's and other diseases |
| CN103209981B (zh) | 2010-09-10 | 2016-12-28 | 盐野义制药株式会社 | 具有ampk活化作用的杂环稠合咪唑衍生物 |
| WO2012040499A2 (en) | 2010-09-22 | 2012-03-29 | Surface Logix, Inc. | Metabolic inhibitors |
| US8546427B2 (en) | 2010-10-20 | 2013-10-01 | Hoffmann-La Roche Inc. | Tetrahydroquinoline derivatives |
| US8809369B2 (en) | 2011-01-26 | 2014-08-19 | Hoffmann-La Roche Inc. | Tetrahydroquinoline derivatives |
| SG192941A1 (en) | 2011-02-25 | 2013-09-30 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| WO2012119979A1 (en) | 2011-03-07 | 2012-09-13 | Glaxosmithkline Llc | 1H-PYROLLO[3,2-d]PYRIMIDINEDIONE DERIVATIVES |
| KR101624020B1 (ko) | 2011-03-07 | 2016-05-24 | 글락소스미스클라인 엘엘씨 | 퀴놀리논 유도체 |
| RU2014105624A (ru) | 2011-08-12 | 2015-09-20 | Ф. Хоффманн-Ля Рош Аг | Соединения индазола, способ их применения и фармацевтическая композиция |
| US9611249B2 (en) | 2012-02-12 | 2017-04-04 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1H-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999043654A2 (en) * | 1998-02-25 | 1999-09-02 | Genetics Institute, Inc. | Inhibitors of phospholipase enzymes |
| EP1844771A2 (en) * | 2001-06-20 | 2007-10-17 | Wyeth | Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| WO2003082271A2 (en) * | 2002-04-03 | 2003-10-09 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| WO2005014554A1 (en) * | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
| US20070129404A1 (en) * | 2003-10-15 | 2007-06-07 | Masahiko Hagihara | Novel indazole derivatives |
| WO2010064875A2 (en) * | 2008-12-05 | 2010-06-10 | Korea Institute Of Science And Technology | Novel indazole derivatives or pharmaceutically acceptable salts thereof as protein kinase inhibitors for proliferative diseases treatment, and a pharmaceutical composition containing the same as an active ingredient |
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