JP2016520515A5 - - Google Patents
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- JP2016520515A5 JP2016520515A5 JP2016501157A JP2016501157A JP2016520515A5 JP 2016520515 A5 JP2016520515 A5 JP 2016520515A5 JP 2016501157 A JP2016501157 A JP 2016501157A JP 2016501157 A JP2016501157 A JP 2016501157A JP 2016520515 A5 JP2016520515 A5 JP 2016520515A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- lower alkyl
- heterocycle
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 63
- -1 formamide Chemical compound 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 28
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
- 101001098868 Homo sapiens Proprotein convertase subtilisin/kexin type 9 Proteins 0.000 claims description 14
- 102100038955 Proprotein convertase subtilisin/kexin type 9 Human genes 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims 43
- 125000000623 heterocyclic group Chemical group 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 38
- 125000003342 alkenyl group Chemical group 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 12
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 12
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 12
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 12
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 6
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 6
- BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000002723 alicyclic group Chemical group 0.000 claims 3
- 125000005518 carboxamido group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- HOVRQUHNZHBKKJ-UHFFFAOYSA-N 4-(carbamoylamino)benzoic acid Chemical compound NC(=O)NC1=CC=C(C(O)=O)C=C1 HOVRQUHNZHBKKJ-UHFFFAOYSA-N 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 101001051093 Homo sapiens Low-density lipoprotein receptor Proteins 0.000 description 8
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 108010028554 LDL Cholesterol Proteins 0.000 description 3
- 239000002299 complementary DNA Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012894 fetal calf serum Substances 0.000 description 3
- 235000009200 high fat diet Nutrition 0.000 description 3
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
- 230000003827 upregulation Effects 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000013218 HFD mouse model Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000006143 cell culture medium Substances 0.000 description 2
- 230000003833 cell viability Effects 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical class ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- KIAPYAZGXJCKQL-UHFFFAOYSA-N 2-[n-[(2-methylpropan-2-yl)oxycarbonyl]anilino]acetic acid Chemical compound CC(C)(C)OC(=O)N(CC(O)=O)C1=CC=CC=C1 KIAPYAZGXJCKQL-UHFFFAOYSA-N 0.000 description 1
- RIMRLBGNCLMSNH-UHFFFAOYSA-N 2-phenylpiperazine Chemical compound C1NCCNC1C1=CC=CC=C1 RIMRLBGNCLMSNH-UHFFFAOYSA-N 0.000 description 1
- WKFFHKBGGZHQAX-UHFFFAOYSA-N 3-phenylpiperazin-2-one Chemical compound O=C1NCCNC1C1=CC=CC=C1 WKFFHKBGGZHQAX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BFJKMQNJQCJCAI-UHFFFAOYSA-N 4-(carbamoylamino)benzenesulfonyl chloride Chemical compound NC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 BFJKMQNJQCJCAI-UHFFFAOYSA-N 0.000 description 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229940122392 PCSK9 inhibitor Drugs 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SAXHIDRUJXPDOD-UHFFFAOYSA-N ethyl hydroxy(phenyl)acetate Chemical compound CCOC(=O)C(O)C1=CC=CC=C1 SAXHIDRUJXPDOD-UHFFFAOYSA-N 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 102000053786 human PCSK9 Human genes 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- FQDDBYGPHUUTRN-UHFFFAOYSA-N methyl 4-isocyanatobenzoate Chemical compound COC(=O)C1=CC=C(N=C=O)C=C1 FQDDBYGPHUUTRN-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361789867P | 2013-03-15 | 2013-03-15 | |
| US61/789,867 | 2013-03-15 | ||
| PCT/US2014/023135 WO2014150395A1 (en) | 2013-03-15 | 2014-03-11 | Anti-pcsk9 compounds and methods for the treatment and/or prevention of cardiovascular diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016520515A JP2016520515A (ja) | 2016-07-14 |
| JP2016520515A5 true JP2016520515A5 (enExample) | 2017-04-13 |
Family
ID=51580758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016501157A Pending JP2016520515A (ja) | 2013-03-15 | 2014-03-11 | 抗ｐｃｓｋ９化合物および心血管疾患の治療および／または予防のための方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US10131637B2 (enExample) |
| EP (1) | EP2968318A4 (enExample) |
| JP (1) | JP2016520515A (enExample) |
| CN (1) | CN105473141A (enExample) |
| AU (1) | AU2014237198A1 (enExample) |
| BR (1) | BR112015023193A2 (enExample) |
| CA (1) | CA2904662A1 (enExample) |
| WO (1) | WO2014150395A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2861582T3 (en) | 2012-05-17 | 2016-08-22 | Array Biopharma Inc | A process for preparing hydroxylated compounds cyclopentylpyrimidin |
| ES2588878T3 (es) | 2012-05-17 | 2016-11-07 | Array Biopharma, Inc. | Proceso para preparar compuestos de ciclopentilpirimidina hidroxilada |
| EP2850200A1 (en) | 2012-05-17 | 2015-03-25 | Genentech, Inc. | Process of making hydroxylated cyclopentapyrimidine compounds and salts thereof |
| SG11201407618VA (en) | 2012-05-17 | 2015-01-29 | Genentech Inc | Amorphous form of an akt inhibiting pyrimidinyl - cyclopentane compound, compositions and methods thereof |
| KR102074535B1 (ko) | 2012-05-17 | 2020-02-06 | 제넨테크, 인크. | 아미노산 화합물의 제조 방법 |
| US10821106B2 (en) | 2015-08-21 | 2020-11-03 | Srx Cardio, Llc | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate PCSK9 protein activity |
| HK1260897A1 (zh) | 2015-08-21 | 2019-12-27 | Portola Pharmaceuticals, Inc. | 使用四氢异喹啉小分子来结合并调节pcsk9的蛋白活性的组合物和方法 |
| US10568882B2 (en) | 2015-08-21 | 2020-02-25 | Srx Cardio, Llc | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators and their use |
| CN105214087B (zh) | 2015-10-29 | 2017-12-26 | 陈敏 | Pcsk9单克隆抗体在制备治疗炎症免疫性疾病药物中的应用 |
| US12282014B2 (en) | 2015-11-19 | 2025-04-22 | Dana-Farber Cancer Institute, Inc. | Methods of identifying compounds that interfere with ERG-driven misguidance of BAF complexes in TMPRSS2-ERG driven prostate cancers |
| WO2017147328A1 (en) * | 2016-02-23 | 2017-08-31 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| AU2017281332A1 (en) | 2016-06-24 | 2018-12-20 | F. Hoffmann-La Roche Ag | Compositions and methods for treating cardiovascular disease |
| TW201823222A (zh) * | 2016-12-23 | 2018-07-01 | 財團法人生物技術開發中心 | 化合物、醫藥組成物及其用途 |
| US11091466B2 (en) | 2017-03-17 | 2021-08-17 | Cardio Therapeutics Pty Ltd | Heterocyclic inhibitors of PCSK9 |
| EP3746124A4 (en) * | 2018-01-30 | 2021-10-27 | Foghorn Therapeutics Inc. | COMPOUNDS AND THEIR USES |
| WO2020005869A2 (en) | 2018-06-25 | 2020-01-02 | Duke University | Compositions and methods for the treatment of cancer characterized with pcsk9 expression |
| WO2020081588A1 (en) | 2018-10-17 | 2020-04-23 | Dana-Farber Cancer Institute, Inc. | Swi/snf family chromatin remodeling complexes and uses thereof |
| UY38485A (es) | 2018-11-27 | 2020-06-30 | Novartis Ag | Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación |
| US20230089867A1 (en) * | 2018-11-27 | 2023-03-23 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| WO2020110011A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic peptides as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorders |
| CN119060040A (zh) | 2019-01-18 | 2024-12-03 | 阿斯利康(瑞典)有限公司 | Pcsk9抑制剂及其使用方法 |
| US12384776B2 (en) | 2019-01-29 | 2025-08-12 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| MX2021014015A (es) | 2019-05-17 | 2022-02-21 | Regeneron Pharma | Metodos basados en el genoma para reducir el riesgo cardiovascular. |
| JP7561195B2 (ja) | 2020-01-29 | 2024-10-03 | フォグホーン セラピューティクス インコーポレイテッド | 化合物及びその使用 |
| US12383555B2 (en) | 2020-05-20 | 2025-08-12 | Foghorn Therapeutics Inc. | Methods of treating cancers |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017313A (en) | 1974-09-30 | 1977-04-12 | E. I. Du Pont De Nemours And Company | Photosensitive composition containing a leuco dye, a photosensitizer, an aromatic aldehyde and a secondary or tertiary amine and the use thereof in a direct-print process |
| DE3021590A1 (de) | 1980-06-09 | 1981-12-17 | Hoechst Ag, 6000 Frankfurt | 4-halogen-5-(halogenmethyl-phenyl)-oxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltenden strahlungsempfindliche massen |
| AU5723500A (en) * | 1999-05-24 | 2000-12-12 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| DE10063008A1 (de) | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
| US20050288340A1 (en) | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| EP2007717A1 (en) | 2006-04-11 | 2008-12-31 | Actelion Pharmaceuticals Ltd. | Novel sulfonamide compounds |
| WO2008125623A2 (en) * | 2007-04-13 | 2008-10-23 | Novartis Ag | Molecules and methods for modulating proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| US20090275053A1 (en) | 2008-04-30 | 2009-11-05 | Board Of Regents, The University Of Texas System | Cell-based pcsk9 screening assay |
| US9085527B2 (en) * | 2008-07-08 | 2015-07-21 | Catabasis Pharmaceuticals, Inc. | Fatty acid acylated salicylates and their uses |
| WO2011006000A1 (en) * | 2009-07-08 | 2011-01-13 | Haiyan Liu | Berberine derivatives useful for modulating lipid levels and their methods of synthesis |
| CN102596941A (zh) * | 2009-10-01 | 2012-07-18 | 卡迪拉保健有限公司 | 用于治疗血脂异常和相关疾病的化合物 |
| WO2012044090A2 (ko) * | 2010-09-29 | 2012-04-05 | 크리스탈지노믹스(주) | 단백질 키나제 억제 활성을 갖는 신규한 아미노퀴나졸린 화합물 |
| CN107243078A (zh) * | 2012-05-25 | 2017-10-13 | 克塔巴西斯制药有限公司 | 使前蛋白转化酶枯草溶菌素/kexin 9型（pcsk9）减少的方法 |
| AR092924A1 (es) * | 2012-10-09 | 2015-05-06 | Sanofi Sa | Derivados de pirrolidinona como moduladores de gpr119 para el tratamiento de diabetes, obesidad, dislipidemia y trastornos relacionados |
-
2014
- 2014-03-11 US US14/767,126 patent/US10131637B2/en active Active
- 2014-03-11 EP EP14768980.6A patent/EP2968318A4/en not_active Withdrawn
- 2014-03-11 WO PCT/US2014/023135 patent/WO2014150395A1/en not_active Ceased
- 2014-03-11 CA CA2904662A patent/CA2904662A1/en not_active Abandoned
- 2014-03-11 CN CN201480016207.6A patent/CN105473141A/zh active Pending
- 2014-03-11 BR BR112015023193A patent/BR112015023193A2/pt active Search and Examination
- 2014-03-11 AU AU2014237198A patent/AU2014237198A1/en not_active Abandoned
- 2014-03-11 JP JP2016501157A patent/JP2016520515A/ja active Pending
-
2017
- 2017-12-01 US US15/829,028 patent/US20180079730A1/en not_active Abandoned
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