CN102378574B - 取代的偶氮蒽衍生物、药物组合物及其使用方法 - Google Patents
取代的偶氮蒽衍生物、药物组合物及其使用方法 Download PDFInfo
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- CN102378574B CN102378574B CN2010800152644A CN201080015264A CN102378574B CN 102378574 B CN102378574 B CN 102378574B CN 2010800152644 A CN2010800152644 A CN 2010800152644A CN 201080015264 A CN201080015264 A CN 201080015264A CN 102378574 B CN102378574 B CN 102378574B
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- phenyl
- base
- compound
- carbonyl
- dimethyl
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- 0 *C(*)(*#C)N(*)C([C@]1N(*)Cc2cc(*(CC3)**[C@@]3C3)c3cc2C1)=O Chemical compound *C(*)(*#C)N(*)C([C@]1N(*)Cc2cc(*(CC3)**[C@@]3C3)c3cc2C1)=O 0.000 description 3
- RNERNOZXQRPVHP-ZGAORZAOSA-N CC(C)(C)OC(N(Cc(c(C1)c2)cc3c2OCC(c(cc2)ccc2OCc(cc2)cc(Cl)c2Cl)(O)O3)[C@@H]1C(OC)=O)=O Chemical compound CC(C)(C)OC(N(Cc(c(C1)c2)cc3c2OCC(c(cc2)ccc2OCc(cc2)cc(Cl)c2Cl)(O)O3)[C@@H]1C(OC)=O)=O RNERNOZXQRPVHP-ZGAORZAOSA-N 0.000 description 2
- MAVVNUHCONQFSP-WNJJXGMVSA-N CC(C)(C)OC(N[C@@H](Cc(cc1)cc(OC2)c1O[C@@H]2c(cc1)ccc1OCc(cc1)cc(Cl)c1I)C(OC)=C)=O Chemical compound CC(C)(C)OC(N[C@@H](Cc(cc1)cc(OC2)c1O[C@@H]2c(cc1)ccc1OCc(cc1)cc(Cl)c1I)C(OC)=C)=O MAVVNUHCONQFSP-WNJJXGMVSA-N 0.000 description 1
- CYVWGLODALLLFP-UHFFFAOYSA-N CC(C)(C)[Si](c1ccccc1)(c1ccccc1)OCC(c(cc1)ccc1OCc(cc1)cc(Cl)c1Cl)O Chemical compound CC(C)(C)[Si](c1ccccc1)(c1ccccc1)OCC(c(cc1)ccc1OCc(cc1)cc(Cl)c1Cl)O CYVWGLODALLLFP-UHFFFAOYSA-N 0.000 description 1
- QGNKHRPLTLEGLV-UHFFFAOYSA-N CC(C)C1c2ccncc2NC1 Chemical compound CC(C)C1c2ccncc2NC1 QGNKHRPLTLEGLV-UHFFFAOYSA-N 0.000 description 1
- MZPXSSPINQPKEG-NGCAANIMSA-N CC[C@@H](c1ccccc1)N[C@@H](Cc(cc1)cc(OC2)c1O[C@@H]2c(cc1)ccc1OCc(cc1)cc(Cl)c1Cl)C([O]=C)=O Chemical compound CC[C@@H](c1ccccc1)N[C@@H](Cc(cc1)cc(OC2)c1O[C@@H]2c(cc1)ccc1OCc(cc1)cc(Cl)c1Cl)C([O]=C)=O MZPXSSPINQPKEG-NGCAANIMSA-N 0.000 description 1
- ZPGYXIVFYCKLQK-SFHVURJKSA-N C[C@](Cc(cc1)ccc1-c(cc1)ccc1C#N)(C(OC)=O)N Chemical compound C[C@](Cc(cc1)ccc1-c(cc1)ccc1C#N)(C(OC)=O)N ZPGYXIVFYCKLQK-SFHVURJKSA-N 0.000 description 1
- OCTJYSUNNNNRLF-GOQQBFOMSA-N Cc1c(C)nccc1-c1ccc(C/C(/C(OC)=O)=N/C(C(Cc2c3)NCc2cc2c3OC[C@H](c3cc(OCc(cc4Cl)ccc4Cl)ccc3)O2)=O)cc1 Chemical compound Cc1c(C)nccc1-c1ccc(C/C(/C(OC)=O)=N/C(C(Cc2c3)NCc2cc2c3OC[C@H](c3cc(OCc(cc4Cl)ccc4Cl)ccc3)O2)=O)cc1 OCTJYSUNNNNRLF-GOQQBFOMSA-N 0.000 description 1
- CBZDDKMGJLYWRG-HNNXBMFYSA-N Cc1c(C)nccc1Oc1ccc(C[C@@H](C(OC)=O)N)cc1 Chemical compound Cc1c(C)nccc1Oc1ccc(C[C@@H](C(OC)=O)N)cc1 CBZDDKMGJLYWRG-HNNXBMFYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- A61P9/10—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
-
- 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
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Secondary Cells (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16452309P | 2009-03-30 | 2009-03-30 | |
| US61/164,523 | 2009-03-30 | ||
| US30934810P | 2010-03-01 | 2010-03-01 | |
| US61/309,348 | 2010-03-01 | ||
| PCT/US2010/029172 WO2010114824A1 (en) | 2009-03-30 | 2010-03-30 | Substituted azoanthracene derivatives, pharmaceutical compositions, and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102378574A CN102378574A (zh) | 2012-03-14 |
| CN102378574B true CN102378574B (zh) | 2013-11-20 |
Family
ID=42828657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010800152644A Active CN102378574B (zh) | 2009-03-30 | 2010-03-30 | 取代的偶氮蒽衍生物、药物组合物及其使用方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US8383644B2 (https=) |
| EP (1) | EP2413693B1 (https=) |
| JP (1) | JP5755217B2 (https=) |
| KR (1) | KR101732978B1 (https=) |
| CN (1) | CN102378574B (https=) |
| AU (1) | AU2010232750B2 (https=) |
| BR (1) | BRPI1013579A2 (https=) |
| CA (1) | CA2757084C (https=) |
| DK (1) | DK2413693T3 (https=) |
| EA (1) | EA023430B1 (https=) |
| ES (1) | ES2553645T3 (https=) |
| IL (1) | IL214822A (https=) |
| MA (1) | MA33219B1 (https=) |
| MX (1) | MX2011010347A (https=) |
| SG (1) | SG174205A1 (https=) |
| TN (1) | TN2011000437A1 (https=) |
| WO (1) | WO2010114824A1 (https=) |
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| US12234236B1 (en) | 2023-09-14 | 2025-02-25 | Ascletis Pharma (China) Co., Limited | GLP-1R agonist and therapeutic method thereof |
| US12291530B1 (en) | 2023-11-24 | 2025-05-06 | Ascletis Pharma (China) Co., Limited | GLP-1R agonist and therapeutic method thereof |
| US12421245B2 (en) | 2020-04-01 | 2025-09-23 | Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd. | Pharmaceutically acceptable acid salt of free base of GLP1 receptor agonist, and preparation method therefor |
| US12459954B2 (en) | 2020-04-01 | 2025-11-04 | Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd. | Crystalline form a of GLP-1 receptor agonist and preparation method therefor |
| TWI918593B (zh) | 2018-05-08 | 2026-03-21 | 美商Vtv治療有限責任公司 | Glp1r激動劑的治療用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5755217B2 (ja) | 2009-03-30 | 2015-07-29 | トランステック・ファーマ,エルエルシー | 置換アゾアントラセン誘導体、その医薬組成物とその使用の方法 |
| CN103030646B (zh) * | 2011-09-29 | 2016-08-24 | 上海恒瑞医药有限公司 | 苯并二氧六环类衍生物、其制备方法及其在医药上的应用 |
| CA2850987C (en) | 2011-10-17 | 2019-10-15 | Biotheryx, Inc. | Substituted biaryl alkyl amides |
| SG10201704716XA (en) | 2013-01-17 | 2017-07-28 | Vtv Therapeutics Llc | Combinations Of A GLP1R Agonist And Metformin And Use Thereof For The Treatment Of Type 2 Diabetes And Other Disorders |
| WO2016033105A1 (en) | 2014-08-29 | 2016-03-03 | The Board Of Regents Of The University Of Texas System | Novel capsazepine analogs for the treatment of cancer and other proliferative diseases |
| JOP20190060A1 (ar) * | 2016-09-26 | 2019-03-26 | Chugai Pharmaceutical Co Ltd | مشتق بيرازولو بيريدين له تأثير مساعد لمستقبل glp-1 |
| WO2019103060A1 (ja) * | 2017-11-22 | 2019-05-31 | 第一三共株式会社 | 縮合三環化合物 |
| JP7461104B2 (ja) * | 2017-11-29 | 2024-04-03 | 中外製薬株式会社 | Glp-1受容体アゴニスト作用を持つピラゾロピリジン誘導体を含有する医薬組成物 |
| EP3790549A1 (en) | 2018-05-08 | 2021-03-17 | vTv Therapeutics LLC | Therapeutic uses of glp1r agonists |
| CA3045644C (en) * | 2018-06-13 | 2024-01-16 | Pfizer Inc. | Glp-1 receptor agonists and uses thereof |
| WO2020234726A1 (en) | 2019-05-20 | 2020-11-26 | Pfizer Inc. | Combinations comprising benzodioxol as glp-1r agonists for use in the treatment of nash/nafld and related diseases |
| CN115209883B (zh) * | 2020-01-20 | 2025-05-20 | 新月生物科学 | 新型细胞代谢调节化合物及其用途 |
| TW202144340A (zh) | 2020-04-03 | 2021-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 稠合咪唑類衍生物、其製備方法及其在醫藥上的應用 |
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| US20230348484A1 (en) * | 2020-05-28 | 2023-11-02 | Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd. | Method for preparing glp-1 receptor agonist free base |
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| WO2022268152A1 (zh) | 2021-06-24 | 2022-12-29 | 杭州中美华东制药有限公司 | Glp-1受体激动剂及其组合物和用途 |
| WO2023029979A1 (zh) * | 2021-09-03 | 2023-03-09 | 杭州中美华东制药有限公司 | Glp-1受体激动剂中间体的制备方法 |
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| WO2005014532A1 (en) * | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| CN1658871A (zh) * | 2001-12-21 | 2005-08-24 | 诺沃挪第克公司 | 作为gk活化剂的酰胺衍生物 |
| US20060178515A1 (en) * | 2003-03-26 | 2006-08-10 | Hamed Aissaoui | Tetrahydroisoquinolyl acetamide derivatives for use as orexin receptor antagonists |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795265A (fr) * | 1972-02-09 | 1973-08-09 | Philips Nv | Nouveaux derives de quinoleine a activite pharmacologique |
| US5756532A (en) * | 1995-11-06 | 1998-05-26 | American Home Products Corporation | Aminomethyl-2 3 8 9-tetrahydro-7H-1 4-dioxino 2 3-E!-indol-8-ones and derivatives |
| JP2002534512A (ja) * | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドglp−1アゴニスト |
| NZ527276A (en) * | 2001-03-27 | 2004-11-26 | Actelion Pharmaceuticals Ltd | 1,2,3,4-tetrahydroisoquinoline derivatives as urotensin II receptor antagonists |
| ATE348828T1 (de) | 2001-10-19 | 2007-01-15 | Transtech Pharma Inc | Beta-carbolin-derivate als ptp-inhibitoren |
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| WO2009126709A1 (en) | 2008-04-09 | 2009-10-15 | Transtech Pharma, Inc. | Ligands for the glp-1 receptor and methods for discovery thereof |
| JP5755217B2 (ja) | 2009-03-30 | 2015-07-29 | トランステック・ファーマ,エルエルシー | 置換アゾアントラセン誘導体、その医薬組成物とその使用の方法 |
| US8501982B2 (en) | 2010-06-09 | 2013-08-06 | Receptos, Inc. | GLP-1 receptor stabilizers and modulators |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI918593B (zh) | 2018-05-08 | 2026-03-21 | 美商Vtv治療有限責任公司 | Glp1r激動劑的治療用途 |
| US12421245B2 (en) | 2020-04-01 | 2025-09-23 | Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd. | Pharmaceutically acceptable acid salt of free base of GLP1 receptor agonist, and preparation method therefor |
| US12459954B2 (en) | 2020-04-01 | 2025-11-04 | Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd. | Crystalline form a of GLP-1 receptor agonist and preparation method therefor |
| US12234236B1 (en) | 2023-09-14 | 2025-02-25 | Ascletis Pharma (China) Co., Limited | GLP-1R agonist and therapeutic method thereof |
| US12291530B1 (en) | 2023-11-24 | 2025-05-06 | Ascletis Pharma (China) Co., Limited | GLP-1R agonist and therapeutic method thereof |
Also Published As
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| DK2413693T3 (en) | 2015-11-16 |
| ES2553645T3 (es) | 2015-12-10 |
| CN102378574A (zh) | 2012-03-14 |
| US9175003B2 (en) | 2015-11-03 |
| EA201171197A1 (ru) | 2012-04-30 |
| TN2011000437A1 (en) | 2013-03-27 |
| MA33219B1 (fr) | 2012-04-02 |
| US20130096150A1 (en) | 2013-04-18 |
| CA2757084A1 (en) | 2010-10-07 |
| EA201171197A8 (ru) | 2014-10-30 |
| IL214822A0 (en) | 2011-11-30 |
| BRPI1013579A2 (pt) | 2020-11-03 |
| KR101732978B1 (ko) | 2017-05-08 |
| US20110160198A1 (en) | 2011-06-30 |
| HK1164050A1 (en) | 2012-09-21 |
| JP5755217B2 (ja) | 2015-07-29 |
| EP2413693A4 (en) | 2012-08-22 |
| JP2012522060A (ja) | 2012-09-20 |
| AU2010232750A1 (en) | 2011-09-08 |
| CA2757084C (en) | 2017-08-29 |
| US20150148539A1 (en) | 2015-05-28 |
| WO2010114824A8 (en) | 2011-10-06 |
| WO2010114824A1 (en) | 2010-10-07 |
| SG174205A1 (en) | 2011-10-28 |
| IL214822A (en) | 2016-08-31 |
| EP2413693B1 (en) | 2015-09-09 |
| EP2413693A1 (en) | 2012-02-08 |
| MX2011010347A (es) | 2011-11-29 |
| EA023430B1 (ru) | 2016-06-30 |
| AU2010232750B2 (en) | 2015-10-29 |
| US8987295B2 (en) | 2015-03-24 |
| KR20120006506A (ko) | 2012-01-18 |
| US8383644B2 (en) | 2013-02-26 |
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