CA2857197C - Novel glp-1 receptor modulators - Google Patents

Novel glp-1 receptor modulators Download PDF

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Publication number
CA2857197C
CA2857197C CA2857197A CA2857197A CA2857197C CA 2857197 C CA2857197 C CA 2857197C CA 2857197 A CA2857197 A CA 2857197A CA 2857197 A CA2857197 A CA 2857197A CA 2857197 C CA2857197 C CA 2857197C
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compound
tert
mmol
butyl
phenyl
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CA2857197A
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French (fr)
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CA2857197A1 (en
Inventor
Marcus F. Boehm
Esther Martinborough
Manisha Moorjani
Junko Tamiya
Liming Huang
Adam R. Yeager
Enugurthi Brahmachary
Thomas Fowler
Andrew Novak
Premji Meghani
Michael Knaggs
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Receptos LLC
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Celgene International II SARL
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    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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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    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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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Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013530963A (ja) 2010-06-09 2013-08-01 レセプトス インコーポレイテッド 新規のｇｌｐ−１受容体安定化薬および調節薬
JP6007417B2 (ja) 2011-05-31 2016-10-12 レセプトス エルエルシー 新規ｇｌｐ−１受容体安定剤および調節剤
BR112014013925B1 (pt) 2011-12-12 2022-02-22 Receptos Llc Compostos moduladores do receptor de glp-1 e composição e combinação farmacêutica compreendendo os ditos compostos
CN109867630A (zh) * 2013-06-11 2019-06-11 赛尔基因第二国际有限公司 新型glp-1受体调节剂
CA2955836C (en) * 2014-07-25 2023-02-14 Celgene International Ii Sarl Glp-1 receptor modulators
ES2844573T3 (es) 2014-12-10 2021-07-22 Receptos Llc Moduladores del receptor de GLP-1
CA3017797A1 (en) 2016-03-17 2017-09-21 Thiogenesis Therapeutics, Inc. Compositions for controlled release of cysteamine and systemic treatment of cysteamine sensitive disorders
WO2017192820A1 (en) 2016-05-06 2017-11-09 Ionis Pharmaceuticals, Inc. Glp-1 receptor ligand moiety conjugated oligonucleotides and uses thereof
MX388576B (es) 2016-06-07 2025-03-20 Jacobio Pharmaceuticals Co Ltd Derivados heterociclicos novedosos utiles como inhibidores de shp2.
EA202190196A1 (ru) 2017-03-23 2021-08-31 Джакобио Фармасьютикалс Ко., Лтд. Новые гетероциклические производные, применимые в качестве ингибиторов shp2
WO2018200833A1 (en) * 2017-04-28 2018-11-01 Celgene International Ii Sarl Novel glp-1 receptor modulators
CA3076392A1 (en) 2017-09-20 2019-03-28 Thiogenesis Therapeutics, Inc. Methods for the treatment of cysteamine sensitive disorders
US20210393623A1 (en) 2018-09-26 2021-12-23 Jacobio Pharmaceuticals Co., Ltd. Novel Heterocyclic Derivatives Useful as SHP2 Inhibitors
MA54555A (fr) * 2018-11-22 2021-09-29 Qilu Regor Therapeutics Inc Agonistes de glp-1r et leurs utilisations
CA3121202A1 (en) 2018-11-30 2020-06-04 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
WO2020210582A1 (en) * 2019-04-11 2020-10-15 University Of The Sciences Allosteric agonists and positive allosteric modulators of glucagon-like peptide 1 receptor
EP3953344A4 (en) * 2019-04-12 2023-08-09 Qilu Regor Therapeutics Inc. GLP-IR AGONISTS AND THEIR USES
CN112521501A (zh) * 2019-09-18 2021-03-19 鸿运华宁（杭州）生物医药有限公司 Gipr抗体及其与glp-1的融合蛋白质，以及其药物组合物和应用
EP4048664A1 (en) 2019-10-25 2022-08-31 Gilead Sciences, Inc. Glp-1r modulating compounds
WO2021096284A1 (ko) * 2019-11-15 2021-05-20 일동제약(주) Glp-1 수용체 작용제 및 이의 용도
IL296336A (en) * 2020-03-18 2022-11-01 Lg Chemical Ltd Glp-1 receptor agonist, pharmaceutical composition comprising same, and method for preparing same
CN117645601A (zh) * 2020-06-10 2024-03-05 重庆康丁医药技术有限公司 一种具有心血管益处的glp-1小分子
EP4247804A1 (en) 2020-11-20 2023-09-27 Gilead Sciences, Inc. Polyheterocyclic glp-1 r modulating compounds
MX2023006186A (es) 2020-11-27 2023-08-07 Shenzhen Salubris Pharm Co Ltd Derivado de benzimidazol y método de preparación del mismo y uso médico del mismo.
CN117222644A (zh) * 2021-04-12 2023-12-12 诺华股份有限公司 2-((4-((S)-2-(4-氯-2-氟苯基)-2-甲基苯并[d][1,3]二氧戊环-4-基)哌啶-1-基)甲基)-1-(((S)-氧杂环丁烷-2-基)甲基)-1H-咪唑衍生物作为GLP1受体激活剂治疗肥胖症
IL306110A (en) 2021-04-21 2023-11-01 Gilead Sciences Inc Carboxy-benzimidazole glp-1r modulating compounds
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
TW202521534A (zh) 2023-11-24 2025-06-01 香港商歌禮製藥(中國)有限公司 Glp-1r 激動劑及其治療方法

Family Cites Families (28)

* 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
US5424286A (en) 1993-05-24 1995-06-13 Eng; John Exendin-3 and exendin-4 polypeptides, and pharmaceutical compositions comprising same
US6174905B1 (en) 1996-09-30 2001-01-16 Mitsui Chemicals, Inc. Cell differentiation inducer
DE122007000044I2 (de) 1997-01-07 2011-05-05 Amylin Pharmaceuticals Inc Verwendung von exedinen und deren antagonisten zur verminderung der lebensmittelaufnahme
US6583139B1 (en) * 1997-07-31 2003-06-24 Eugene D. Thorsett Compounds which inhibit leukocyte adhesion mediated by VLA-4
PL338457A1 (en) * 1997-07-31 2000-11-06 Elan Pharm Inc Sulphonylated dipeptidic compounds capable to inhibit adhesion of leucocytes through the mediation of vla-4
EP1005445B1 (en) * 1997-08-22 2004-05-26 F. Hoffmann-La Roche Ag N-alkanoylphenylalanine derivatives
US6191171B1 (en) 1997-11-20 2001-02-20 Merck & Co., Inc. Para-aminomethylaryl carboxamide derivatives
EP1992641A3 (en) 1998-12-07 2009-07-29 Ipsen Pharma GLP-1 analogues
US6902744B1 (en) 1999-01-14 2005-06-07 Amylin Pharmaceuticals, Inc. Exendin agonist formulations and methods of administration thereof
EP1150565A1 (en) * 1999-02-08 2001-11-07 LION bioscience AG Thiazole derivatives and combinatorial libraries thereof
TR200401217T4 (tr) 2000-03-07 2004-06-21 Aventis Pharma Deutschland Gmbh İkameli 3-Fenil-5-Alkoksi-1,3,4-Oksdiazol-2-one (ve) hormona duyarlı lipazın önlenmesinde kullanılması
WO2002028830A1 (en) * 2000-09-29 2002-04-11 Ajinomoto Co.,Inc. Novel phenylalanine derivatives
WO2003048081A2 (en) 2001-12-04 2003-06-12 Bristol-Myers Squibb Company Glycinamides as factor xa inhibitors
EP1477482B1 (en) 2002-02-20 2010-04-14 Ajinomoto Co., Inc. Novel phenylalanine derivative
JPWO2003089410A1 (ja) * 2002-04-19 2005-08-25 協和醗酵工業株式会社 フェニルアラニン誘導体
US7345049B2 (en) * 2003-12-22 2008-03-18 Ajinomoto Co., Inc. Phenylalanine derivatives
CA2555594A1 (en) * 2004-02-10 2005-08-25 Janssen Pharmaceutica N.V. Pyridazinones as antagonists of a4 integrins
US7825139B2 (en) 2005-05-25 2010-11-02 Forest Laboratories Holdings Limited (BM) Compounds and methods for selective inhibition of dipeptidyl peptidase-IV
US7816324B2 (en) 2007-03-13 2010-10-19 Board Of Regents, The University Of Texas System Composition and method for the treatment of diseases affected by a peptide receptor
CA2688136A1 (en) 2007-06-08 2008-12-11 Advinus Therapeutics Private Limited Pyrrole-2-carboxamide derivatives as glucokinase activators, their process and pharmaceutical application
WO2011094890A1 (en) * 2010-02-02 2011-08-11 Argusina Inc. Phenylalanine derivatives and their use as non-peptide glp-1 receptor modulators
JP2013530963A (ja) 2010-06-09 2013-08-01 レセプトス インコーポレイテッド 新規のｇｌｐ−１受容体安定化薬および調節薬
JP6007417B2 (ja) 2011-05-31 2016-10-12 レセプトス エルエルシー 新規ｇｌｐ−１受容体安定剤および調節剤
CN105763220B (zh) 2011-06-01 2021-03-05 康普技术有限责任公司 具有非双工器隔离子系统的宽带分布式天线系统
BR112014013925B1 (pt) 2011-12-12 2022-02-22 Receptos Llc Compostos moduladores do receptor de glp-1 e composição e combinação farmacêutica compreendendo os ditos compostos
CN109867630A (zh) 2013-06-11 2019-06-11 赛尔基因第二国际有限公司 新型glp-1受体调节剂

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