CN102725291B - 作为沉默调节蛋白调节剂的双环吡啶和相关的类似物 - Google Patents
作为沉默调节蛋白调节剂的双环吡啶和相关的类似物 Download PDFInfo
- Publication number
- CN102725291B CN102725291B CN201080060180.2A CN201080060180A CN102725291B CN 102725291 B CN102725291 B CN 102725291B CN 201080060180 A CN201080060180 A CN 201080060180A CN 102725291 B CN102725291 B CN 102725291B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- fluorine
- compound
- substituted
- sirtuin
- 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.)
- Expired - Fee Related
Links
- 0 C*(C)c1ccccn1 Chemical compound C*(C)c1ccccn1 0.000 description 31
- ZICRALLMHKILDG-UHFFFAOYSA-N CC(C)c1ccn[nH]1 Chemical compound CC(C)c1ccn[nH]1 ZICRALLMHKILDG-UHFFFAOYSA-N 0.000 description 2
- OTGDCHNSXQUISE-UHFFFAOYSA-N Brc1ccc2OCCNc2n1 Chemical compound Brc1ccc2OCCNc2n1 OTGDCHNSXQUISE-UHFFFAOYSA-N 0.000 description 1
- OAXRKEIAAXLLLO-MFGFFKQHSA-N C=C(c1cc([IH+])ccc1)/N=C(\C(OC1)=C(N)N[C@H]1O)/[ClH+] Chemical compound C=C(c1cc([IH+])ccc1)/N=C(\C(OC1)=C(N)N[C@H]1O)/[ClH+] OAXRKEIAAXLLLO-MFGFFKQHSA-N 0.000 description 1
- NGCGYTPSRNKABQ-QYEKGNEQSA-N CC(C)/C(/C)=C/C=N\NC Chemical compound CC(C)/C(/C)=C/C=N\NC NGCGYTPSRNKABQ-QYEKGNEQSA-N 0.000 description 1
- WVMBISZHWMJNNM-UHFFFAOYSA-N CC(C)c1c[nH]nc1 Chemical compound CC(C)c1c[nH]nc1 WVMBISZHWMJNNM-UHFFFAOYSA-N 0.000 description 1
- GABKDWUBEVLXEW-UHFFFAOYSA-N CC1(CN(C)C2=CC=CNN2)COC1 Chemical compound CC1(CN(C)C2=CC=CNN2)COC1 GABKDWUBEVLXEW-UHFFFAOYSA-N 0.000 description 1
- PXRDDNBENPRBAG-UHFFFAOYSA-N CC1=[I]C=NC(N2CC[U+]CC2)=C1 Chemical compound CC1=[I]C=NC(N2CC[U+]CC2)=C1 PXRDDNBENPRBAG-UHFFFAOYSA-N 0.000 description 1
- FNUWEHVZWXPRIV-UHFFFAOYSA-N CC1NNC11COC1 Chemical compound CC1NNC11COC1 FNUWEHVZWXPRIV-UHFFFAOYSA-N 0.000 description 1
- OLKDHWGNKXDYOQ-UHFFFAOYSA-N CCOC/[U]=C/CNC1=NC(C2=CCCC(C(F)(F)F)=C2)=CCC1[N+]([O-])=O Chemical compound CCOC/[U]=C/CNC1=NC(C2=CCCC(C(F)(F)F)=C2)=CCC1[N+]([O-])=O OLKDHWGNKXDYOQ-UHFFFAOYSA-N 0.000 description 1
- HLBPEOXJBLQZRH-VOMCLLRMSA-N CC[IH]1(CC(C)[C@H](C)C1)C1=CC=CC2C(Br)=C12 Chemical compound CC[IH]1(CC(C)[C@H](C)C1)C1=CC=CC2C(Br)=C12 HLBPEOXJBLQZRH-VOMCLLRMSA-N 0.000 description 1
- HHFJHCXBGHXHLU-UHFFFAOYSA-N Cc(cc1)cc2c1NCCO2 Chemical compound Cc(cc1)cc2c1NCCO2 HHFJHCXBGHXHLU-UHFFFAOYSA-N 0.000 description 1
- GHPODDMCSOYWNE-UHFFFAOYSA-N Cc(cc1)cc2c1OCO2 Chemical compound Cc(cc1)cc2c1OCO2 GHPODDMCSOYWNE-UHFFFAOYSA-N 0.000 description 1
- LRSFUCPDCKILCL-UHFFFAOYSA-N Cc1cccc(N(CC2)CC2F)c1 Chemical compound Cc1cccc(N(CC2)CC2F)c1 LRSFUCPDCKILCL-UHFFFAOYSA-N 0.000 description 1
- XPNMCOGUXSYLBP-UHFFFAOYSA-N Fc1cccc(C([Ar]=C2Cl)=CC[IH]C3=C2OCCN3)c1 Chemical compound Fc1cccc(C([Ar]=C2Cl)=CC[IH]C3=C2OCCN3)c1 XPNMCOGUXSYLBP-UHFFFAOYSA-N 0.000 description 1
- CJTDPUUGKHXTHT-UHFFFAOYSA-N O=C(Nc1ccncc1)N1c(nc(cc2)Br)c2OCC1 Chemical compound O=C(Nc1ccncc1)N1c(nc(cc2)Br)c2OCC1 CJTDPUUGKHXTHT-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
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- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nutrition Science (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25626909P | 2009-10-29 | 2009-10-29 | |
| US61/256,269 | 2009-10-29 | ||
| PCT/US2010/054880 WO2011059839A1 (en) | 2009-10-29 | 2010-10-29 | Bicyclic pyridines and analogs as sirtuin modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102725291A CN102725291A (zh) | 2012-10-10 |
| CN102725291B true CN102725291B (zh) | 2016-12-21 |
Family
ID=43991957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080060180.2A Expired - Fee Related CN102725291B (zh) | 2009-10-29 | 2010-10-29 | 作为沉默调节蛋白调节剂的双环吡啶和相关的类似物 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9556201B2 (enExample) |
| EP (1) | EP2493888B1 (enExample) |
| JP (1) | JP2013509442A (enExample) |
| KR (1) | KR20120092141A (enExample) |
| CN (1) | CN102725291B (enExample) |
| AU (1) | AU2010319842A1 (enExample) |
| BR (1) | BR112012010010A2 (enExample) |
| CA (1) | CA2779303A1 (enExample) |
| ES (1) | ES2574927T3 (enExample) |
| IL (1) | IL219372A0 (enExample) |
| IN (1) | IN2012DN03799A (enExample) |
| MX (1) | MX2012004995A (enExample) |
| RU (1) | RU2550821C2 (enExample) |
| WO (1) | WO2011059839A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101578235B1 (ko) | 2007-12-10 | 2015-12-16 | 노파르티스 아게 | 유기 화합물 |
| CA2738794C (en) | 2008-09-29 | 2016-01-05 | Sirtris Pharmaceuticals, Inc. | Chromenone analogs as sirtuin modulators |
| SG11201406552UA (en) | 2012-04-25 | 2014-11-27 | Takeda Pharmaceutical | Nitrogenated heterocyclic compound |
| US9394315B2 (en) | 2012-05-08 | 2016-07-19 | Lycera Corporation | Tetrahydro[1,8]naphthyridine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| MX367341B (es) | 2012-05-08 | 2019-08-14 | Merck Sharp & Dohme | Tetrahidronaftiridina y compuestos biciclicos relacionados para la inhibicion de la actividad de rorgamma y el tratamiento de enfermedades. |
| US9527841B2 (en) | 2012-07-13 | 2016-12-27 | Takeda Pharmaceutical Company Limited | Substituted pyrido[2,3-b]pyrazines as phosphodiesterase 2A inhibitors |
| BR112015002493A8 (pt) * | 2012-08-30 | 2019-07-30 | Hoffmann La Roche | composto, composição farmacêutica, processo para a preparação de uma composição farmacêutica, kit e uso de um composto” |
| CN102977117A (zh) * | 2012-11-26 | 2013-03-20 | 盛世泰科生物医药技术(苏州)有限公司 | 一种6-溴-2,2-二甲基-2h-吡啶并[3,2-b][1,4]恶嗪-3(4h)-酮的合成方法 |
| GEP201606554B (en) * | 2012-12-26 | 2016-10-10 | Takeda Pharmaceuticals Co | Nitrogenated heterocyclic compound |
| JP6280912B2 (ja) | 2013-03-14 | 2018-02-14 | 武田薬品工業株式会社 | 複素環化合物 |
| RU2015153061A (ru) * | 2013-05-13 | 2017-06-15 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Замещенные связанные мостиковой связью мочевинные аналоги в качестве модуляторов сиртуина |
| WO2016081692A2 (en) * | 2014-11-19 | 2016-05-26 | Glaxosmithkline Llc | Substituted bridged urea analogs as sirtuin modulators |
| WO2015002231A1 (ja) | 2013-07-03 | 2015-01-08 | 武田薬品工業株式会社 | 複素環化合物 |
| EP3018123B1 (en) | 2013-07-03 | 2023-05-10 | Takeda Pharmaceutical Company Limited | Amide compound |
| SI3050878T1 (sl) | 2013-09-24 | 2022-01-31 | Fujifilm Corporation | Nova dušik-vsebujoča spojina ali njena sol ali kovinski kompleks le-te |
| US10172915B2 (en) | 2013-10-20 | 2019-01-08 | Duke University | Methods and compositions for activation of sirtuins with Annexin A1 peptides |
| TR201810944T4 (tr) | 2013-10-25 | 2018-08-27 | Novartis Ag | Fgfr4 inhibitörleri olarak halka-füzyonlu bisiklik piridil türevleri. |
| WO2015095788A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | 2-ACYLAMIDOMETHYL AND SULFONYLAMIDOMETHYL BENZOXAZINE CARBAMATES FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE |
| WO2015095792A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Carbamate benzoxaxine propionic acids and acid derivatives for modulation of rorgamma activity and the treatment of disease |
| WO2015095795A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | TETRAHYDRONAPHTHYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE, AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE |
| CA2935944A1 (en) | 2014-01-09 | 2015-07-16 | The J. David Gladstone Institutes, A Testamentary Trust Established Under The Will Of J. David Gladstone | Substituted benzoxazine and related compounds |
| CA2939305A1 (en) | 2014-02-27 | 2015-09-03 | Lycera Corporation | Adoptive cellular therapy using an agonist of retinoic acid receptor-related orphan receptor gamma & related therapeutic methods |
| JP2017114764A (ja) * | 2014-04-25 | 2017-06-29 | 武田薬品工業株式会社 | 片頭痛治療剤 |
| WO2015171558A2 (en) | 2014-05-05 | 2015-11-12 | Lycera Corporation | BENZENESULFONAMIDO AND RELATED COMPOUNDS FOR USE AS AGONISTS OF RORγ AND THE TREATEMENT OF DISEASE |
| CA2947290A1 (en) | 2014-05-05 | 2015-11-12 | Lycera Corporation | Tetrahydroquinoline sulfonamide and related compounds for use as agonists of rory and the treatment of disease |
| MX2016015997A (es) | 2014-06-02 | 2017-04-05 | Glaxosmithkline Intellectual Property (No 2) Ltd | Preparacion y uso de beta-d-nicotinamida ribosido cristalina. |
| CN106715455A (zh) | 2014-06-06 | 2017-05-24 | 葛兰素史密斯克莱知识产权（第2 号）有限公司 | 烟酰胺核苷类似物及其药物组合物和用途 |
| ES2756748T3 (es) | 2014-10-03 | 2020-04-27 | Novartis Ag | Uso de derivados de piridilo bicíclicos de anillo fusionado como inhibidores de fgfr4 |
| CN107207521A (zh) * | 2014-11-19 | 2017-09-26 | 葛兰素史密斯克莱知识产权（第2 号）有限公司 | 作为沉默调节蛋白调节剂的取代的桥连脲类似物 |
| CA2975997A1 (en) | 2015-02-11 | 2016-08-18 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as rorgammat inhibitors and uses thereof |
| US9802917B2 (en) | 2015-03-25 | 2017-10-31 | Novartis Ag | Particles of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide |
| JP2018515491A (ja) | 2015-05-05 | 2018-06-14 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγの作動薬及び疾患の療法として使用するジヒドロ−２Ｈ−ベンゾ［ｂ］［１，４］オキサジンスルホンアミド及び関連化合物 |
| EP3307738B1 (en) | 2015-06-11 | 2022-04-20 | The Regents of the University of Michigan | Aryl dihydro-2h-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of rory and the treatment of disease |
| WO2017075182A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as rorgammat inhibitors and uses thereof |
| WO2017075185A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| CA3002846A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Substituted bicyclic pyrazole compounds as rorgammat inhibitors and uses thereof |
| CN118994191A (zh) | 2016-02-05 | 2024-11-22 | 戴纳立制药公司 | 受体相互作用蛋白激酶1的抑制剂 |
| CN106243045A (zh) * | 2016-07-27 | 2016-12-21 | 常州大学 | 一种2,5‑二甲氧基‑4‑氨基嘧啶的制备方法 |
| JOP20190053A1 (ar) | 2016-09-23 | 2019-03-21 | Novartis Ag | مركبات أزا إندازول للاستخدام في إصابات الأوتار و/ أو الرباط |
| ES2925173T3 (es) | 2016-11-08 | 2022-10-14 | Bristol Myers Squibb Co | Acidos propiónicos sustituidos en la posición 3 como inhibidores de la integrina alfa V |
| HRP20220636T1 (hr) | 2016-12-09 | 2022-07-22 | Denali Therapeutics Inc. | Spojevi korisni kao inhibitori ripk1 |
| US9969768B1 (en) | 2017-11-16 | 2018-05-15 | King Saud University | Oleanolic acid methyl ester derivatives |
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- 2010-10-29 KR KR1020127013635A patent/KR20120092141A/ko not_active Ceased
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Also Published As
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| KR20120092141A (ko) | 2012-08-20 |
| AU2010319842A1 (en) | 2012-05-17 |
| RU2012122065A (ru) | 2013-12-10 |
| BR112012010010A2 (pt) | 2018-03-20 |
| US20120252780A1 (en) | 2012-10-04 |
| EP2493888A1 (en) | 2012-09-05 |
| JP2013509442A (ja) | 2013-03-14 |
| EP2493888A4 (en) | 2013-05-01 |
| WO2011059839A1 (en) | 2011-05-19 |
| EP2493888B1 (en) | 2016-04-06 |
| CA2779303A1 (en) | 2011-05-19 |
| IL219372A0 (en) | 2012-06-28 |
| CN102725291A (zh) | 2012-10-10 |
| IN2012DN03799A (enExample) | 2015-08-28 |
| US9556201B2 (en) | 2017-01-31 |
| RU2550821C2 (ru) | 2015-05-20 |
| ES2574927T3 (es) | 2016-06-23 |
| MX2012004995A (es) | 2012-10-03 |
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