JP5728099B2 - 抗糖尿病剤として有用な新規環状アザベンゾイミダゾール誘導体 - Google Patents
抗糖尿病剤として有用な新規環状アザベンゾイミダゾール誘導体 Download PDFInfo
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- JP5728099B2 JP5728099B2 JP2013555544A JP2013555544A JP5728099B2 JP 5728099 B2 JP5728099 B2 JP 5728099B2 JP 2013555544 A JP2013555544 A JP 2013555544A JP 2013555544 A JP2013555544 A JP 2013555544A JP 5728099 B2 JP5728099 B2 JP 5728099B2
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- alkyl
- phenyl
- cycloalkyl
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- 0 ***c1nc2c(*)nc(*)c(*)c2[n]1* Chemical compound ***c1nc2c(*)nc(*)c(*)c2[n]1* 0.000 description 5
Classifications
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- 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
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- 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
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161446551P | 2011-02-25 | 2011-02-25 | |
| US61/446,551 | 2011-02-25 | ||
| PCT/US2012/026261 WO2012116145A1 (en) | 2011-02-25 | 2012-02-23 | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015013034A Division JP2015096550A (ja) | 2011-02-25 | 2015-01-27 | 抗糖尿病剤として有用な新規環状アザベンゾイミダゾール誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014506598A JP2014506598A (ja) | 2014-03-17 |
| JP5728099B2 true JP5728099B2 (ja) | 2015-06-03 |
Family
ID=46721223
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013555544A Active JP5728099B2 (ja) | 2011-02-25 | 2012-02-23 | 抗糖尿病剤として有用な新規環状アザベンゾイミダゾール誘導体 |
| JP2015013034A Pending JP2015096550A (ja) | 2011-02-25 | 2015-01-27 | 抗糖尿病剤として有用な新規環状アザベンゾイミダゾール誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015013034A Pending JP2015096550A (ja) | 2011-02-25 | 2015-01-27 | 抗糖尿病剤として有用な新規環状アザベンゾイミダゾール誘導体 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8796258B2 (enExample) |
| EP (2) | EP2677869B1 (enExample) |
| JP (2) | JP5728099B2 (enExample) |
| KR (2) | KR20150075120A (enExample) |
| CN (2) | CN105001219A (enExample) |
| AU (1) | AU2012220595B2 (enExample) |
| BR (2) | BR112013021236B1 (enExample) |
| CA (1) | CA2826649C (enExample) |
| CL (1) | CL2013002414A1 (enExample) |
| CO (1) | CO6751268A2 (enExample) |
| CR (1) | CR20130409A (enExample) |
| DO (1) | DOP2013000193A (enExample) |
| EA (2) | EA201690035A1 (enExample) |
| EC (1) | ECSP13012900A (enExample) |
| ES (1) | ES2652662T3 (enExample) |
| GT (1) | GT201300208A (enExample) |
| IL (1) | IL227640A0 (enExample) |
| MA (1) | MA34916B1 (enExample) |
| MX (1) | MX348131B (enExample) |
| MY (1) | MY159058A (enExample) |
| NI (1) | NI201300074A (enExample) |
| PE (1) | PE20140859A1 (enExample) |
| PH (1) | PH12013501686A1 (enExample) |
| SG (1) | SG192941A1 (enExample) |
| TN (1) | TN2013000309A1 (enExample) |
| WO (1) | WO2012116145A1 (enExample) |
| ZA (1) | ZA201306057B (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2012033149A1 (ja) * | 2010-09-10 | 2012-03-15 | 塩野義製薬株式会社 | Ampk活性化作用を有するヘテロ環縮合イミダゾール誘導体 |
| EP2733141B1 (en) * | 2011-07-15 | 2019-01-09 | Shionogi & Co., Ltd. | Azabenzimidazole derivative having ampk-activating activity |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| RU2015109706A (ru) * | 2012-08-22 | 2016-10-10 | Мерк Шарп И Доум Корп. | Новые производные азабензимидазол гексагидрофуро[3, 2-в]фурана |
| EP2888008B1 (en) * | 2012-08-22 | 2018-12-26 | Merck Sharp & Dohme Corp. | Novel azabenzimidazole tetrahydrofuran derivatives |
| WO2014031465A1 (en) * | 2012-08-22 | 2014-02-27 | Merck Sharp & Dohme Corp. | Novel azabenzimidazole tetrahydropyran derivatives |
| WO2014069426A1 (ja) * | 2012-10-31 | 2014-05-08 | 塩野義製薬株式会社 | Ampk活性化作用を有するベンズイミダゾールおよびアザベンズイミダゾール誘導体 |
| TWI644899B (zh) | 2013-02-04 | 2018-12-21 | 健生藥品公司 | Flap調節劑 |
| EP3070085B1 (en) | 2013-02-04 | 2019-01-09 | Janssen Pharmaceutica NV | Flap modulators |
| CA2903657A1 (en) | 2013-02-27 | 2014-09-04 | Shionogi & Co., Ltd. | Indole and azaindole derivatives each having ampk-activating activity |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| DK3022210T3 (en) | 2013-07-17 | 2018-06-06 | Boehringer Ingelheim Int | NEW AZABENZIMIDAZOLD DERIVATIVES. |
| WO2015063011A1 (en) * | 2013-10-31 | 2015-05-07 | Boehringer Ingelheim International Gmbh | Azabenzimidazole derivatives |
| KR101532211B1 (ko) * | 2014-04-30 | 2015-06-30 | 세종대학교산학협력단 | Ampk 억제기능에 기반한 뇌졸중 치료용 약학적 조성물 및 방법 |
| WO2016001224A1 (en) * | 2014-06-30 | 2016-01-07 | Debiopharm International S.A. | Novel activators of amp-activated protein kinases |
| EP3180338B1 (en) * | 2014-08-11 | 2018-05-09 | Boehringer Ingelheim International GmbH | Azabenzimidazole derivatives as amp protein kinase agonistes |
| AU2015309863B2 (en) | 2014-08-27 | 2019-12-05 | Shionogi & Co., Ltd. | Azaindole derivative having AMPK-activating effect |
| KR20170077131A (ko) | 2014-10-28 | 2017-07-05 | 시오노기세야쿠 가부시키가이샤 | Ampk 활성화 작용을 갖는 복소환 유도체 |
| JP6612881B2 (ja) * | 2015-01-16 | 2019-11-27 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規なアザベンゾイミダゾール誘導体 |
| US10307402B2 (en) | 2015-01-16 | 2019-06-04 | Boehringer Ingelheim International Gmbh | Azabenzimidazole derivatives as agonists of the AMP-activated protein kinase |
| HUE049938T2 (hu) * | 2015-03-23 | 2020-11-30 | Jounce Therapeutics Inc | Icos elleni antitestek |
| WO2017103670A1 (en) * | 2015-12-14 | 2017-06-22 | Zenith Epigenetics Lid. | 1h-imidazo[4,5-b]pyridinyl and 2-oxo-2,3-dihydro-1h-imidazo[4,5-b]pyridinyl heterocyclic bet bromodomain inhibitors |
| JPWO2017146186A1 (ja) | 2016-02-26 | 2018-12-20 | 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 |
| US10526345B2 (en) * | 2016-04-08 | 2020-01-07 | Mankind Pharma Ltd. | Compounds as GPR119 agonists |
| US10208030B2 (en) * | 2016-04-08 | 2019-02-19 | Mankind Pharma Ltd. | GPR119 agonist compounds |
| US10954229B2 (en) | 2016-04-08 | 2021-03-23 | Mankind Pharma Ltd. | GPR119 agonist compounds |
| WO2017188288A1 (ja) * | 2016-04-26 | 2017-11-02 | 塩野義製薬株式会社 | Ampk活性化作用を有する5-置換アザベンズイミダゾール誘導体 |
| CN109476661A (zh) | 2016-05-20 | 2019-03-15 | 盐野义制药株式会社 | 具有ampk活化作用的5-取代苯并咪唑及5-取代氮杂苯并咪唑衍生物 |
| ES2937789T3 (es) * | 2016-08-19 | 2023-03-31 | Rigel Pharmaceuticals Inc | Activadores de AMPK directos de benzimidazol |
| MA56480B1 (fr) | 2016-12-16 | 2022-12-30 | Pfizer | Agonistes du récepteur glp-1 et leurs utilisations |
| CN108727267B (zh) * | 2017-05-26 | 2022-05-13 | 江苏新元素医药科技有限公司 | 一类urat1抑制剂及其应用 |
| CN108558876B (zh) * | 2018-05-28 | 2020-08-04 | 中南大学 | 吡唑[3,4-b]并吡啶类衍生物及其制备方法和应用 |
| CU20210042A7 (es) | 2018-11-22 | 2022-01-13 | Qilu Regor Therapeutics Inc | Compuestos agonistas de glp-1r y composiciones farmacéuticas que lo contienen |
| US10954221B2 (en) | 2019-04-12 | 2021-03-23 | Qilu Regor Therapeutics Inc. | GLP-1R agonists and uses thereof |
| JP2023526625A (ja) * | 2020-05-19 | 2023-06-22 | キャリーオペ,インク. | Ampkアクチベーター |
| CN116390925A (zh) | 2020-06-26 | 2023-07-04 | 卡尔优普公司 | Ampk活化剂 |
| US20250263402A1 (en) * | 2020-10-12 | 2025-08-21 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | Benzimidazolone glp-1 receptor agonist and use thereof |
| US20240180882A1 (en) * | 2021-03-08 | 2024-06-06 | The Regents Of The University Of California | Compounds for protection of noise-induced hearing-loss |
| US12404348B2 (en) | 2021-11-19 | 2025-09-02 | The Brigham And Women's Hospital, Inc. | Bifunctional chimeric molecules for labeling of kinases with target binding moieties and methods of use thereof |
| UY40035A (es) * | 2021-11-23 | 2023-05-31 | Kallyope Inc | Activadores de la ampk |
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| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3630200A (en) | 1969-06-09 | 1971-12-28 | Alza Corp | Ocular insert |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US3914250A (en) | 1974-08-01 | 1975-10-21 | American Home Prod | 1,4-Diazepino{8 6,5,4-jk{9 carbazoles |
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