[go: up one dir, main page]

ES2655091T3 - Derivados del ácido pirrolidíncarboxílico como agonistas del receptor 43 acoplado a proteína G (GPR43), composición farmacéutica y métodos para su uso en el tratamiento de trastornos metabólicos - Google Patents

Derivados del ácido pirrolidíncarboxílico como agonistas del receptor 43 acoplado a proteína G (GPR43), composición farmacéutica y métodos para su uso en el tratamiento de trastornos metabólicos Download PDF

Info

Publication number
ES2655091T3
ES2655091T3 ES10792934T ES10792934T ES2655091T3 ES 2655091 T3 ES2655091 T3 ES 2655091T3 ES 10792934 T ES10792934 T ES 10792934T ES 10792934 T ES10792934 T ES 10792934T ES 2655091 T3 ES2655091 T3 ES 2655091T3
Authority
ES
Spain
Prior art keywords
alkyl
aryl
heteroaryl
group
cycloalkyl
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.)
Active
Application number
ES10792934T
Other languages
English (en)
Inventor
Hamid Hoveyda
Didier Schils
Ludivine Zoute
Julien Parcq
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ogeda SA
Original Assignee
Ogeda SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ogeda SA filed Critical Ogeda SA
Application granted granted Critical
Publication of ES2655091T3 publication Critical patent/ES2655091T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • 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
    • 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/14—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 three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Un compuesto de fórmula I:**Fórmula** y sales y solvatos farmacéuticamente aceptables del mismo, en donde R1 y R2 son H, D es C>=O; L2 es enlace sencillo; R es H o alquilo lineal o ramificado, arilo, dioxoleno; Ar1 es un grupo arilo o heteroarilo de 5 a 6 miembros, grupo cicloalquilo de 3 a 6 miembros, o un grupo alquilo C3-C6 lineal o ramificado, cada uno de los cuales está opcionalmente sustituido con uno o más grupos seleccionados de halo, ciano, alquilo, haloalquilo, cicloalquilo, arilo, heteroarilo, hidroxilo, alcoxi, haloalcoxilo, amino, alquilamino, carboxilo, alcoxicarbonilo, alquilcarboniloxilo, alquilcarbonilamino, haloalquilcarbonilamino, carbamoilo, hidroxicarbamoilo, alquilcarbamoilo, carbamoilamino, alquilcarbamoilamino, alquilsulfonilo, haloalquilsulfonilo, sulfamoilo, alquilsulfamoilo, alquilsulfonilamino, haloalquilsulfonilamino o dos sustituyentes forman un grupo alquilendioxi o un grupo haloalquilendioxi, cada uno de dichos sustituyentes arilo o heteroarilo está opcionalmente sustituido con uno o más sustituyentes adicionales seleccionados entre halo, ciano, alquilo, haloalquilo, hidroxilo, alcoxi, haloalcoxi; Ar2 es un grupo arilo o heteroarilo, cicloalquilo o heterociclilo monocíclico, cada uno de los cuales está opcionalmente sustituido con uno o más grupos seleccionados de halo, ciano, nitro, alquilo, haloalquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo, heterociclilo, heterociclilalquilo, arilo, aralquilo, heteroarilo, benzoxazol-2-ilo, heteroarilalquilo, hidroxilo, hidroxialquilo, alcoxi, haloalcoxi, alcoxialcoxi, cicloalquiloxi, cicloalquilalquiloxi, heterocicliloxi, ariloxi, heteroariloxi, alcoxialquilo, haloalcoxialquilo, arilalquiloxi, heteroarilalquiloxi, ariloxialquilo, heteroariloxialquilo, amino, alquilamino, arilcarbonilo, carboxi, alcoxicarbonilo, ariloxicarbonilo, heteroariloxicarbonilo, alquilcarboniloxi, arilcarboniloxi, heteroarilcarboniloxi, alquilcarbonilamino, carbamoílo, hidroxicarbamoílo, alquilcarbamoílo, arilcarbamoílo, heteroarilcarbamoilo, carbamoilamino, alquilcarbamoilamino, alquilsulfonilo, arilsulfonilo, heteroarilsulfonilo, sulfamoílo, alquilsulfamoílo, arilsulfamoilo, heteroarilsulfamoiIo, alquilsulfonilamino, arilsulfonilamino, heteroarilsulfonilamino, oxo, o dos sustituyentes forman un grupo alquilendioxi o un grupo haloalquilendioxi, o condensados con el grupo arilo, heteroarilo o cicloalquilo pueden ser una o más unidades estructurales arilo o heteroarilo, cada uno de dichos sustituyentes está opcionalmente sustituido con uno o más sustituyentes seleccionados entre halo, ciano, nitro, alquilo, hidroxialquilo, haloalquilo, cianometilo, cicloalquilo, heterociclilo, arilo opcionalmente sustituido con un grupo cloro o metilo, heteroarilo, heteroalquilo, hidroxilo, alcoxilo, alcoxialquilo, alcoxialcoxilo, haloalcoxilo, cicloalquiloxilo, cicloalquilalquiloxilo, ariloxilo, aralquiloxi opcionalmente sustituido por un grupo fluoro, carboxi, alcoxicarbonilo, alquilcarboniloxi, amino, alquilamino, alquilcarbonilamino, haloalquilcarbonilamino, carbamoílo, hidroxicarbamoílo, alquilcarbamoilo, carbamoilalquiloxi, carbamoilamino, alquilcarbamoilamino, carbamimidoilo, hidroxicarbamimidoilo, alquilsulfonilo, haloalquilsulfonilo, cicloalquilsulfonilo, heterociclilsulfonilo, arilsulfonilo, sulfamoílo , alquilsulamoilo, alquilsulfonilamino, haloalquilsulfonilamino, oxo y haloalcoxialquilo; R3 es H, ciano, alquilo, hidroxialquilo, aralquilo, alcoxialquilo, acetilo, arilsulfonilo; R3' es H o alquilo C1-C4; R4 es H, ciano, alquilo C1-C4; en donde, a menos que se indique lo contrario: alquilo comprende de 1 a 6 átomos de carbono; cicloalquilo comprende de 3 a 10 átomos de carbono; heterociclilo contiene de 3 a 10 átomos en el anillo y conteniendo cada anillo un heteroátomo puede tener 1, 2, 3 o 4 heteroátomos seleccionados de átomos de N, O y/o S;
ES10792934T 2009-12-18 2010-12-17 Derivados del ácido pirrolidíncarboxílico como agonistas del receptor 43 acoplado a proteína G (GPR43), composición farmacéutica y métodos para su uso en el tratamiento de trastornos metabólicos Active ES2655091T3 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP09306270 2009-12-18
US37337010P 2010-08-13 2010-08-13
US37601310P 2010-08-23 2010-08-23
PCT/EP2010/070040 WO2011073376A1 (en) 2009-12-18 2010-12-17 Pyrrolidine or thiazolidine carboxylic acid derivatives, pharmaceutical composition and methods for use in treating metabolic disordersas as agonists of g- protein coupled receptor 43 (gpr43)

Publications (1)

Publication Number Publication Date
ES2655091T3 true ES2655091T3 (es) 2018-02-16

Family

ID=42236460

Family Applications (1)

Application Number Title Priority Date Filing Date
ES10792934T Active ES2655091T3 (es) 2009-12-18 2010-12-17 Derivados del ácido pirrolidíncarboxílico como agonistas del receptor 43 acoplado a proteína G (GPR43), composición farmacéutica y métodos para su uso en el tratamiento de trastornos metabólicos

Country Status (23)

Country Link
US (6) US9695120B2 (es)
EP (2) EP3255038A1 (es)
JP (1) JP6144913B2 (es)
KR (1) KR101827529B1 (es)
CN (1) CN102812003B (es)
AU (1) AU2010332765C1 (es)
BR (1) BR112012018374B1 (es)
CA (1) CA2784528C (es)
CY (1) CY1119730T1 (es)
DK (1) DK2513053T3 (es)
EA (1) EA023861B3 (es)
ES (1) ES2655091T3 (es)
HR (1) HRP20171991T1 (es)
HU (1) HUE038064T2 (es)
LT (1) LT2513053T (es)
MX (1) MX339252B (es)
NO (1) NO2513053T3 (es)
PL (1) PL2513053T3 (es)
PT (1) PT2513053T (es)
RS (1) RS56751B1 (es)
SI (1) SI2513053T1 (es)
SM (1) SMT201800004T1 (es)
WO (1) WO2011073376A1 (es)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102812003B (zh) * 2009-12-18 2015-01-21 欧洲筛选有限公司 吡咯烷羧酸衍生物、药物组合物以及在代谢紊乱中作为g-蛋白偶联受体43(gpr43)激动剂使用的方法
PT2800738T (pt) * 2012-01-06 2020-06-23 Novartis Ag Compostos heterocíclicos e métodos para a utilização dos mesmos
AR091739A1 (es) 2012-07-11 2015-02-25 Elcelyx Therapeutics Inc Composiciones y metodos para reducir el riesgo cardiometabolico
AR094929A1 (es) 2013-02-28 2015-09-09 Bristol Myers Squibb Co Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2
CN105102448B (zh) 2013-02-28 2018-03-06 百时美施贵宝公司 作为rock1和rock2抑制剂的苯基吡唑衍生物
CN105916500A (zh) * 2013-11-27 2016-08-31 欧洲筛选有限公司 用于治疗炎性疾病的化合物、药物组合物和方法
WO2016028971A1 (en) * 2014-08-21 2016-02-25 Bristol-Myers Squibb Company Tied-back benzamide derivatives as potent rock inhibitors
KR101656662B1 (ko) 2014-11-18 2016-09-12 한국생명공학연구원 2-옥소-1,2,3,4-테트라하이드로피리미딘-5-카르복사미드 유도체를 유효성분으로 함유하는 대사성 질환 예방 또는 치료용 약학적 조성물
CN107033015B (zh) * 2017-06-02 2019-04-30 南京欧信医药技术有限公司 一种药物中间体的合成方法
JP7062792B2 (ja) 2018-02-13 2022-05-06 ギリアード サイエンシーズ， インコーポレイテッド Ｐｄ－１／ｐｄ－ｌ１阻害剤
EP3781556B1 (en) 2018-04-19 2025-06-18 Gilead Sciences, Inc. Pd-1/pd-l1 inhibitors
CN118221646A (zh) 2018-07-13 2024-06-21 吉利德科学公司 Pd-1/pd-l1抑制剂
KR102635333B1 (ko) 2018-10-24 2024-02-15 길리애드 사이언시즈, 인코포레이티드 Pd-1/pd-l1 억제제
SG11202110742TA (en) 2019-04-02 2021-10-28 Aligos Therapeutics Inc Compounds targeting prmt5
WO2021018786A1 (en) 2019-07-26 2021-02-04 INSERM (Institut National de la Santé et de la Recherche Médicale) Use of ffar2 agonists for the treatment of bacterial superinfections post-viral infection
CN110981779B (zh) * 2019-11-23 2021-02-26 武汉理工大学 R-2-(2,5-二氟苯基)吡咯烷的合成方法
CA3180417A1 (en) 2020-06-10 2021-12-16 Guillaume Dutheuil Synthesis of (2s,5r)-5-(2-chlorophenyl)-1-(2'-methoxy-[1,1'-biphenyl]-4-carbonyl)pyrrolidine-2-carboxylic acid
CN120077024A (zh) 2022-10-11 2025-05-30 艾匹克治疗公司 (2s,5r)-5-(2-氯苯基)-1-(2'-甲氧基-[1,1'-联苯]-4-羰基)吡咯烷-2-羧酸的多晶型物及其制备方法

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542788A (en) 1968-06-12 1970-11-24 Searle & Co 1-amino-5-phenyl-2-pyrrolepropionic acid and congeners
US4006075A (en) 1975-01-06 1977-02-01 Exxon Research And Engineering Company Method of regenerating a cracking catalyst with substantially complete combustion of carbon monoxide
DE3421295A1 (de) 1984-06-08 1985-12-12 Basf Ag, 6700 Ludwigshafen Neue pyrrolidincarbonsaeurederivative, verfahren zu ihrer herstellung
JPH06104658B2 (ja) * 1988-06-23 1994-12-21 三菱化成株式会社 ピロールカルボン酸誘導体
FR2678938B1 (fr) * 1991-07-10 1993-10-08 Rhone Poulenc Rorer Sa Derives de pyrrolidine, leur preparation et les medicaments les contenant.
GB9206757D0 (en) * 1992-03-27 1992-05-13 Ferring Bv Novel peptide receptor ligands
AU1856997A (en) 1996-02-02 1997-08-22 Merck & Co., Inc. Method for raising hdl cholesterol levels
JP3005469B2 (ja) 1996-06-05 2000-01-31 住友軽金属工業株式会社 内面スズめっき長尺銅管の製造方法
US6177464B1 (en) 1997-03-14 2001-01-23 Sepracor, Inc. Ring opening metathesis of alkenes
WO2001085720A1 (en) 2000-05-05 2001-11-15 Smithkline Beecham Corporation Novel anti-infectives
US7105556B2 (en) * 2001-05-30 2006-09-12 Bristol-Myers Squibb Company Conformationally constrained analogs useful as antidiabetic and antiobesity agents and method
ATE370137T1 (de) 2001-11-02 2007-09-15 Glaxo Group Ltd 4-(6-gliedriger)-heteroaryl-acyl-pyrrolidin derivate als hcv-inhibitoren
FI20030014A0 (fi) * 2003-01-03 2003-01-03 Orion Corp Prolyylioligopeptidaasia inhiboivaa aktiivisuutta omaavia yhdisteitä
US20040142379A1 (en) * 2003-01-16 2004-07-22 Carlsberg Research Laboratory Affinity fishing for ligands and proteins receptors
WO2005014532A1 (en) * 2003-08-08 2005-02-17 Transtech Pharma, Inc. Aryl and heteroaryl compounds, compositions and methods of use
CN1832920A (zh) * 2003-08-08 2006-09-13 特兰斯泰克制药公司 芳基和杂芳基化合物,组合物及其使用方法
TW200528107A (en) * 2003-11-25 2005-09-01 Nissan Chemical Ind Ltd T-type calcium channel inhibitor
WO2005122379A2 (en) * 2004-05-27 2005-12-22 The Regents Of The University Of California Alpha-4 beta-1 integrin ligands for imaging and therapy
AU2005289810A1 (en) 2004-09-22 2006-04-06 Arena Pharmaceuticals, Inc. GPR43 and modulators thereof for the treatment of metabolic-related disorders
US7759337B2 (en) 2005-03-03 2010-07-20 Amgen Inc. Phthalazine compounds and methods of use
US7425633B2 (en) * 2005-08-26 2008-09-16 National Health Research Institutes Pyrrolidine compounds
US8202902B2 (en) * 2006-05-05 2012-06-19 The Regents Of The University Of Michigan Bivalent SMAC mimetics and the uses thereof
US20090004140A1 (en) * 2007-06-26 2009-01-01 Yao-Ling Qiu 4-substituted pyrrolidine as anti-infectives
US20090233972A1 (en) 2008-03-12 2009-09-17 Yat Sun Or Substituted heterocycles as anti-infectives
US20100074863A1 (en) 2008-09-17 2010-03-25 Yat Sun Or Anti-infective pyrrolidine derivatives and analogs
CN102812003B (zh) * 2009-12-18 2015-01-21 欧洲筛选有限公司 吡咯烷羧酸衍生物、药物组合物以及在代谢紊乱中作为g-蛋白偶联受体43(gpr43)激动剂使用的方法

Also Published As

Publication number Publication date
EA023861B1 (ru) 2016-07-29
AU2010332765A2 (en) 2012-08-09
US20200347016A1 (en) 2020-11-05
CY1119730T1 (el) 2018-06-27
CN102812003B (zh) 2015-01-21
AU2010332765B9 (en) 2015-11-05
DK2513053T3 (en) 2018-01-08
MX2012007030A (es) 2013-02-21
CN102812003A (zh) 2012-12-05
AU2010332765A1 (en) 2012-08-09
PL2513053T3 (pl) 2018-03-30
US10577318B2 (en) 2020-03-03
US10358416B2 (en) 2019-07-23
LT2513053T (lt) 2018-01-25
JP2013514330A (ja) 2013-04-25
US9695120B2 (en) 2017-07-04
US10017468B2 (en) 2018-07-10
JP6144913B2 (ja) 2017-06-07
EP2513053B1 (en) 2017-10-04
KR20140057690A (ko) 2014-05-13
RS56751B1 (sr) 2018-04-30
SMT201800004T1 (it) 2018-03-08
CA2784528A1 (en) 2011-06-23
CA2784528C (en) 2018-05-01
AU2010332765B2 (en) 2015-06-18
US20190300478A1 (en) 2019-10-03
KR101827529B1 (ko) 2018-02-09
EA201200918A1 (ru) 2012-12-28
WO2011073376A1 (en) 2011-06-23
US20200148636A1 (en) 2020-05-14
EA023861B3 (ru) 2016-09-30
HUE038064T2 (hu) 2018-10-29
NO2513053T3 (es) 2018-03-03
PT2513053T (pt) 2018-01-09
EP3255038A1 (en) 2017-12-13
BR112012018374A2 (pt) 2017-03-28
HRP20171991T1 (hr) 2018-02-23
US10781171B2 (en) 2020-09-22
US11072582B2 (en) 2021-07-27
US20170283376A1 (en) 2017-10-05
SI2513053T1 (en) 2018-02-28
BR112012018374B1 (pt) 2021-09-21
US20180297944A1 (en) 2018-10-18
US20130023539A1 (en) 2013-01-24
AU2010332765C1 (en) 2016-09-29
EP2513053A1 (en) 2012-10-24
MX339252B (es) 2016-05-18

Similar Documents

Publication Publication Date Title
ES2655091T3 (es) Derivados del ácido pirrolidíncarboxílico como agonistas del receptor 43 acoplado a proteína G (GPR43), composición farmacéutica y métodos para su uso en el tratamiento de trastornos metabólicos
CR20220371A (es) Agonistas heterocíclicos de glp-1
AR060545A1 (es) Compuestos de benzoaxol y benzotiazol 6-0- sustituidos y metodos de inhibicion de la senalizacion de csf-1r. composiciones farmaceuticas
AR055076A1 (es) Derivados de1,1-dioxido de 1,4-benzotiazepina,procedimiento para prepararlos,composiciones farmaceuticas que los contienen y usos en terapeutica.
AR072085A1 (es) Compuestos triciclicos, metodos para su preparacion, composicion farma-ceutica que los comprende y su uso en el tratamiento de enfermedades me-diadas por la actividad de las proteinas quinasas
CO2019002556A2 (es) Composición farmacéutica
PE20180227A1 (es) Benzamidas sustituidas con 1,3-tiazol-2-ilo
AR061980A1 (es) Acilanilidas sustituidas y metodos para su utilizacion
AR063022A1 (es) Derivados de indol antagonistas del receptor de glucagon, composiciones farmaceuticas que los contienen y usos para tratar diabetes mellitus tipo 2 y estados patologicos relacionados.
CO6170361A2 (es) Composiciones y metodos para modular receptores de c-kit y pdgfr
AR065806A1 (es) Derivados de quinolina, procesos para su preparacion, composiciones farmaceuticas que los contienen y usos para el tratamiento de la artritis reumatoidea.
UY33501A (es) Derivados de acil sulfonamida y sus sales farmacéuticamente aceptables para uso en medicina
CL2012000999A1 (es) Compuestos derivados de pirazoloespirocetona sustituida, inhibidores de acetil-coa carboxilasa; composicion farmaceutica que los comprende; uso para tratar o retrasar la progresion o el inicio de diabetes tipo 2, higado graso no alcoholico (hgna) o la resistencia hepatica a la insulina.
NO20081970L (no) Sulfonamidderivat med PGD2-reseptorantagonistaktivitet
AR049398A1 (es) Derivados de sulfamato y sulfamida; una composicion farmaceutica que los contiene y su uso en la preparacion de un medicamento util para el tratamiento de la epilepsia y trastornos relacionados.
PE20091425A1 (es) Derivados de aminotiazol
MX2021013135A (es) Derivados de 1,1-dioxido de 3-amino-4h-benzo[e][1,2,4] tiadiazina como inhibidores de mrgx2.
HRP20210847T1 (hr) Supstituirani derivati indola kao inhibitori replikacije denga virusa
EA201891780A1 (ru) Производные сульфонамида и содержащие их фармацевтические композиции
AR072803A1 (es) Tetrahidrocinolinas como inhibidores de la 11- beta -hsd1 para la diabetes
AR068115A1 (es) Derivado del acido pirazolcarboxilico metodo de produccion del mismo y fungicida
HRP20080052T3 (hr) Derivati tropana supstituirani imidazopiridinom santagonističkim djelovanjem na ccr5 receptor za liječenje hiv-a i upala
UY29393A1 (es) Nuevos derivados de amidas, sales farmacéuticas aceptables, composiciones que los contienen, procedimientos de preparación y aplicaciones.
AR109224A2 (es) Formas de sales cristalinas de un compuesto 8-azabiciclo[3,2,1]octano, composición farmacéutica que las comprende, procesos para prepararlas, compuesto intermediario de síntesis relacionado y su uso para la fabricación de un medicamento
RU2017117559A (ru) Бензопроизводные с шестичленным кольцом в качестве ингибитора dpp-4 и их применение