KR102271179B1 - 신규의 glp-1 수용체 조절제 - Google Patents

신규의 glp-1 수용체 조절제 Download PDF

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KR102271179B1
KR102271179B1 KR1020167000708A KR20167000708A KR102271179B1 KR 102271179 B1 KR102271179 B1 KR 102271179B1 KR 1020167000708 A KR1020167000708 A KR 1020167000708A KR 20167000708 A KR20167000708 A KR 20167000708A KR 102271179 B1 KR102271179 B1 KR 102271179B1
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formula
delete delete
tert
chr
butyl
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KR20160042868A (ko
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마커스 에프. 보엠
에스더 마틴보로
마니샤 무르자니
준코 타미야
리밍 황
아담 알. 예거
에누구르티 브라흐마차리
토마스 파울러
앤드류 노박
프렘지 메가니
마이클 낙스
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셀진 인터내셔널 Ii 에스에이알엘
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
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    • A61K31/4245—Oxadiazoles
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
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    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170102487A (ko) * 2014-12-10 2017-09-11 셀진 인터내셔널 Ii 에스에이알엘 Glp-1 수용체 조절제

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9278910B2 (en) 2011-05-31 2016-03-08 Receptos, Inc. GLP-1 receptor stabilizers and modulators
EP2791112B1 (en) 2011-12-12 2020-09-23 Celgene International II Sàrl Carboxylic acid derivatives comprising four cycles acting as glp-1 receptor modulators for therapy of diseases such as diabetes
CN105593225B (zh) 2013-06-11 2019-04-16 赛尔基因第二国际有限公司 新型glp-1受体调节剂
CN112457301A (zh) * 2014-07-25 2021-03-09 赛尔基因第二国际有限公司 新的glp-1受体调节剂
ES2908801T3 (es) 2016-06-07 2022-05-04 Jacobio Pharmaceuticals Co Ltd Nuevos derivados heterocíclicos útiles como inhibidores de SHP2
DK3601239T3 (da) 2017-03-23 2024-09-30 Jacobio Pharmaceuticals Co Ltd Novel heterocyclic derivatives useful as shp2 inhibitors
CA3060424A1 (en) * 2017-04-28 2018-11-01 Celgene International Ii Sarl Novel glp-1 receptor modulators
CN112839935A (zh) 2018-09-26 2021-05-25 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
CN109608524B (zh) * 2018-11-09 2022-06-03 北京志道生物科技有限公司 兼具dpp-4抑制及glp1r激活活性的多肽衍生物、制备和应用
CN119874775A (zh) 2020-02-07 2025-04-25 加舒布鲁姆生物公司 杂环glp-1激动剂
CN111548311B (zh) * 2020-06-04 2021-04-23 山西医科大学 一种小分子glp-1r激动剂及其应用
WO2022028572A1 (en) 2020-08-06 2022-02-10 Gasherbrum Bio, Inc. Heterocyclic glp-1 agonists
CN119137124A (zh) 2022-03-09 2024-12-13 加舒布鲁姆生物公司 杂环glp-1激动剂
WO2023179542A1 (en) 2022-03-21 2023-09-28 Gasherbrum Bio , Inc. 5,8-dihydro-1,7-naphthyridine derivatives as glp-1 agonists for the treatment of diabetes
US20250250269A1 (en) 2022-04-14 2025-08-07 Gasherbrum Bio, Inc. Heterocyclic glp-1 agonists
CN114989204A (zh) * 2022-06-16 2022-09-02 西北工业大学 一种葡萄糖响应自修复凝胶用的二苯乙炔类液晶态交联剂的制备方法
CN120981457A (zh) 2023-09-14 2025-11-18 歌礼制药(中国)有限公司 Glp-1r激动剂及其治疗方法
US12291530B1 (en) 2023-11-24 2025-05-06 Ascletis Pharma (China) Co., Limited GLP-1R agonist and therapeutic method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005077915A1 (en) 2004-02-10 2005-08-25 Janssen Pharmaceutica, N.V. Pyridazinones as antagonists of a4 integrins
WO2011094890A1 (en) 2010-02-02 2011-08-11 Argusina Inc. Phenylalanine derivatives and their use as non-peptide glp-1 receptor modulators

Family Cites Families (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1062206B (it) 1974-02-01 1983-09-20 Rotta Research Lab S P A A S Derivati della tirosina attivi sulla muscolatura liscia
DE2423536A1 (de) 1974-05-15 1975-11-27 Bayer Ag 3-amino-phenylessigsaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
SK94393A3 (en) * 1992-09-11 1994-08-10 Thomae Gmbh Dr K Cyclic derivatives of urea, process for their production and their pharmaceutical agents with the content of those
US5424286A (en) 1993-05-24 1995-06-13 Eng; John Exendin-3 and exendin-4 polypeptides, and pharmaceutical compositions comprising same
US5780498A (en) * 1993-11-01 1998-07-14 Ciba-Geigy Japan Limited Endothelin receptor antagonists
US6174905B1 (en) 1996-09-30 2001-01-16 Mitsui Chemicals, Inc. Cell differentiation inducer
WO1998030231A1 (en) 1997-01-07 1998-07-16 Amylin Pharmaceuticals, Inc. Use of exendins and agonists thereof for the reduction of food intake
AU8823498A (en) 1997-07-31 1999-02-22 American Home Products Corporation Sulfonylated dipeptide compounds which inhibit leukocyte adhesion mediated by vla-4
AR016133A1 (es) * 1997-07-31 2001-06-20 Wyeth Corp Compuesto de carbamiloxi que inhiben la adhesion de leucocitos mediada por vla-4, compuestos que son prodrogas de dichos compuestos, composicionfarmaceutica, metodo para fijar vla-4 a una muestra biologica, metodo para el tratamiento de una condicion inflamatoria
US6583139B1 (en) * 1997-07-31 2003-06-24 Eugene D. Thorsett Compounds which inhibit leukocyte adhesion mediated by VLA-4
BR9811988A (pt) * 1997-08-22 2000-09-05 Hoffmann La Roche Derivados de n-alcanoilfenilalanina
CN100369888C (zh) * 1997-08-22 2008-02-20 霍夫曼-拉罗奇有限公司 芳酰基苯丙氨酸衍生物
US6191171B1 (en) 1997-11-20 2001-02-20 Merck & Co., Inc. Para-aminomethylaryl carboxamide derivatives
JP4245682B2 (ja) * 1997-12-25 2009-03-25 協和発酵キリン株式会社 キノリン誘導体、イソキノリン誘導体、およびシンノリン誘導体、並びに抗炎症剤および抗アレルギー剤
US6197794B1 (en) * 1998-01-08 2001-03-06 Celltech Therapeutics Limited Phenylalanine derivatives
MY153569A (en) * 1998-01-20 2015-02-27 Mitsubishi Tanabe Pharma Corp Inhibitors of ?4 mediated cell adhesion
KR100458748B1 (ko) 1998-12-07 2004-12-03 더 어드미니스트레이터즈 오브 더 튜래인 어듀케이셔널 훤드 Ｇｌｐ-1 유사체
DK1140145T4 (da) 1999-01-14 2019-07-22 Amylin Pharmaceuticals Llc Hidtil ukendte exendinagonistformuleringer og fremgangsmåder til indgivelse deraf
EP1150565A1 (en) * 1999-02-08 2001-11-07 LION bioscience AG Thiazole derivatives and combinatorial libraries thereof
JP3795305B2 (ja) * 1999-07-19 2006-07-12 田辺製薬株式会社 医薬組成物
TW200514783A (en) 1999-09-22 2005-05-01 Bristol Myers Squibb Co Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method
ATE355269T1 (de) * 1999-11-18 2006-03-15 Ajinomoto Kk Phenylalaninderivate
DK1244625T3 (da) * 1999-12-06 2005-10-10 Hoffmann La Roche 4-pyridinyl-n-acyl-l-phenylalaniner
SK12752002A3 (sk) 2000-03-07 2003-04-01 Aventis Pharma Deutschland Gmbh Substituované 3-fenyl-5-alkoxy-1,3,4-oxdiazol-2-óny, spôsob ich prípravy a ich použitie ako liečivo na inhibovanie hormónsenzitívnej lipázy
US6960597B2 (en) * 2000-06-30 2005-11-01 Orth-Mcneil Pharmaceutical, Inc. Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists
NZ524122A (en) * 2000-08-18 2005-02-25 Ajinomoto Kk Phenylalanine derivatives useful as pharmaceutical agents
EP1323711B1 (en) * 2000-09-29 2006-11-15 Ajinomoto Co., Inc. Novel phenylalanine derivatives
AU2002350217A1 (en) 2001-12-04 2003-06-17 Bristol-Myers Squibb Company Glycinamides as factor xa inhibitors
EP1454898A4 (en) * 2001-12-13 2006-12-13 Ajinomoto Kk NEW PHENYL ALANIDE DERIVATIVES
JP4470219B2 (ja) 2002-02-20 2010-06-02 味の素株式会社 新規フェニルアラニン誘導体
AU2003235256A1 (en) * 2002-04-19 2003-11-03 Kyowa Hakko Kogyo Co., Ltd. Phenylalanine derivative
US20070276034A1 (en) 2002-05-31 2007-11-29 Luke Esposito Compounds, compositions and methods for the treatment of synucleinopathies
AU2003263071B2 (en) 2002-09-04 2007-03-15 Merck Sharp & Dohme Llc Pyrazolopyrimidines as cyclin-dependent kinase inhibitors
PL224879B1 (pl) 2002-09-04 2017-02-28 Pharmacopeia Drug Discovery Inc Pirazolo [1,5-a] pirymidynowy związek, jego zastosowanie do wytwarzania leku oraz zawierająca go farmaceutyczna kompozycja
US20040152750A1 (en) 2002-12-20 2004-08-05 Kodra Janos Tibor Novel glucagon antagonists
CN101386600B (zh) * 2003-02-20 2011-07-06 味之素株式会社 具有喹唑二酮骨架的苯丙氨酸衍生物的制造方法及制造中间体
BRPI0411412A (pt) 2003-06-13 2006-07-25 S A L V A T Lab Sa novas benzamidas como moduladores ppary
BRPI0418026A (pt) * 2003-12-22 2007-04-17 Ajinomoto Kk derivados de fenilalanina ou sais farmaceuticamente aceitáveis destes, composição farmacêutica, antagonista de alfa4 integrina, e, agente terapêutico ou agente preventivo para doenças
JP4829506B2 (ja) * 2004-02-17 2011-12-07 石原産業株式会社 チオアミド系化合物又はその塩、並びにそれらを含有するサイトカイン産生抑制剤
US7618981B2 (en) * 2004-05-06 2009-11-17 Cytokinetics, Inc. Imidazopyridinyl-benzamide anti-cancer agents
WO2006117743A1 (en) 2005-05-03 2006-11-09 Ranbaxy Laboratories Limited Substituted aromatic compounds as antidiabetic agents
WO2006127595A1 (en) 2005-05-23 2006-11-30 Arena Pharmaceuticals, Inc. 5-aminopyrazole carboxylic acid derivatives and methods of treatment of metabolic-related disorders thereof
US7825139B2 (en) 2005-05-25 2010-11-02 Forest Laboratories Holdings Limited (BM) Compounds and methods for selective inhibition of dipeptidyl peptidase-IV
EP2402326A1 (en) * 2005-06-21 2012-01-04 Ajinomoto Co., Inc. Crystals of hydrochloride salts of a Phenylalanine Derivative, Production Method Thereof and Use Thereof as alpha4 integrin Inhibitors
EP2091916A2 (en) * 2005-11-23 2009-08-26 AstraZeneca AB L-phenylalanine derivatives and their use as integrin antagonists
US20080045521A1 (en) * 2006-06-09 2008-02-21 Astrazeneca Ab Phenylalanine derivatives
EP1878730A1 (en) 2006-07-12 2008-01-16 Bayer Schering Pharma Aktiengesellschaft Substituted isoxazolines, pharmaceutical compositions containing the same, methods of preparing the same, and uses of the same
CN101589028B (zh) * 2006-11-22 2014-02-19 味之素株式会社 具有喹唑啉二酮骨架的苯丙氨酸衍生物的制备方法及制备中间体
WO2008064823A1 (en) * 2006-11-27 2008-06-05 Ucb Pharma, S.A. Bicyclic and heterobicyclic derivatives, processes for preparing them and their uses
WO2008112941A1 (en) 2007-03-13 2008-09-18 Board Of Regents The University Of Texas System Composition and method for the treatment of diseases affected by a peptide receptor
US8299115B2 (en) 2007-06-08 2012-10-30 Debnath Bhuniya Pyrrole-2-carboxamide derivatives as glucokinase activators, their process and pharmaceutical application
WO2009042092A1 (en) * 2007-09-25 2009-04-02 Merck & Co., Inc. 2-aryl or heteroaryl indole derivatives
EP2853529A1 (en) * 2010-03-29 2015-04-01 Ajinomoto Co., Inc. Crystals of salts of phenylalanine derivatives
WO2011156655A2 (en) 2010-06-09 2011-12-15 Receptos, Inc. Novel glp-1 receptor stabilizers and modulators
US9278910B2 (en) 2011-05-31 2016-03-08 Receptos, Inc. GLP-1 receptor stabilizers and modulators
US8999975B2 (en) * 2011-09-19 2015-04-07 Boehringer Ingelheim International Gmbh Substituted N- [1-cyano-2- (phenyl) ethyl] -2-azabicyclo [2.2.1] heptane-3-carboxamide inhibitors of cathepsin C
EP2791112B1 (en) * 2011-12-12 2020-09-23 Celgene International II Sàrl Carboxylic acid derivatives comprising four cycles acting as glp-1 receptor modulators for therapy of diseases such as diabetes
CN105593225B (zh) 2013-06-11 2019-04-16 赛尔基因第二国际有限公司 新型glp-1受体调节剂
CN112457301A (zh) 2014-07-25 2021-03-09 赛尔基因第二国际有限公司 新的glp-1受体调节剂

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005077915A1 (en) 2004-02-10 2005-08-25 Janssen Pharmaceutica, N.V. Pyridazinones as antagonists of a4 integrins
WO2011094890A1 (en) 2010-02-02 2011-08-11 Argusina Inc. Phenylalanine derivatives and their use as non-peptide glp-1 receptor modulators

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170102487A (ko) * 2014-12-10 2017-09-11 셀진 인터내셔널 Ii 에스에이알엘 Glp-1 수용체 조절제
KR102497644B1 (ko) * 2014-12-10 2023-02-08 리셉토스 엘엘씨 Glp-1 수용체 조절제

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