AR081072A1 - Derivados de 3,3-dimetil-tetrahidroquinolina, composiciones farmaceuticas que los contienen, metodo para prepararlos y uso de los mismos para el tratamiento de la diabetes, obesidad y dislipemia - Google Patents

Derivados de 3,3-dimetil-tetrahidroquinolina, composiciones farmaceuticas que los contienen, metodo para prepararlos y uso de los mismos para el tratamiento de la diabetes, obesidad y dislipemia

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Publication number
AR081072A1
AR081072A1 ARP110101228A ARP110101228A AR081072A1 AR 081072 A1 AR081072 A1 AR 081072A1 AR P110101228 A ARP110101228 A AR P110101228A AR P110101228 A ARP110101228 A AR P110101228A AR 081072 A1 AR081072 A1 AR 081072A1
Authority
AR
Argentina
Prior art keywords
alkyl
phenyl
alkylsulfonylaminocarbonyl
oxo
carboxyl
Prior art date
Application number
ARP110101228A
Other languages
English (en)
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR081072A1 publication Critical patent/AR081072A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/36—Sulfur 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
    • C07D401/10—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 aromatic rings
    • 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
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Así como las sales farmacéuticamente aceptables del mismo, en el que R1 a R5 presentan los significados proporcionados en la reivindicacion 1, puede utilizarse como medicamento. Reivindicacion 1: Compuesto de formula (1): en la que: R1 es hidrogeno, halogeno, carboxilo, alcoxicarbonilo, alquilsulfonilaminocarbonilo o cicloalquilsulfonilaminocarbonilo, R2 es hidrogeno, halogeno o carboxilo, R3 es hidrogeno, halogeno, carboxilo, haloalquilo, ciano, alcoxicarbonilo, alquilsulfonilo, alquilsulfonilaminocarbonilo, cicloalquilsulfonilaminocarbonilo, carboxialquilamino(alquil)carbonilo, alquil(hidroxi)pirrolidinilcarbonilo o carboxilpirrolidinilcarbonilo, R4 es hidrogeno, carboxilo, alquilsulfonilaminocarbonilo o cicloalquilsulfonilaminocarbonilo, R5 es piridinilo, piridinilo sustituido, morfolinilpiridinilo, fenilo o fenilo sustituido, en el que piridinilo sustituido y fenilo sustituido son piridinilo y fenilo sustituidos con uno o dos sustituyentes seleccionados independientemente de entre halogeno, halofenilo, alquilo, cicloalquilo, alcoxi, ciano, carboxilo, cicloalquilcarbonilamino, alquilsulfonilamino, fenilsulfonilamino, fenilaminosulfonilo, halofenilsulfonilamino, fenilo, alquilfenilo, alcoxifenilo, cianofenilo, alquilaminocarbonilfenilo, alquilsulfonilfenilo, pirrolidinilo, piridinilcarbonilamino, morfolinilo, alquilmorfolinilo, piperazinilo, alquilpiperazinilo, alquilcarbonilpiperazinilo, alquilfenilpiperazinilo, halofenilpiperazinilo, oxopirrolidinilo, dioxoimidazolidinilo, oxoimidazolidinilo, alquiloxoimidazolidinilo, feniloxoimidazolidinilo, 2-oxo- oxazolidín-3-ilo, alquil-2-oxo-oxazolidín-3-ilo, fenilalquil-2-oxo-oxazolidín-3-ilo, dioxopiperazinilo, alquildioxopiperazinilo, aminocarbonilo, alquilaminocarbonilo, alcoxialquilaminocarbonilo, alquilaminoalquilaminocarbonilo, cicloalquilaminocarbonilo, alquilpirrolidinilaminocarbonilo, tetrahidrofuranilaminocarbonilo, alquilpirrolidinilalquilaminocarbonilo, alcoxicarbonilazetidinilaminocarbonilo, pirrolidinilcarbonilo, piperidinilcarbonilo, alquilsulfonilaminocarbonilo, cicloalquilsuIfonilaminocarbonilo, fenilsulfonilaminocarbonilo, alquilazetidinilaminocarbonilo, haloazetidinilo, alquilpirrolidinilaminocarbonilo, fenilaminocarbonilo, pirazinilaminocarbonilo, aminoalcoxialquilo, aminoalcoxi, carboxilalcoxi, carboxilalcoxialquilo, alquiltetrazolilo, fenilalquiltetrazolilo, alquilaminosulfonilo, alquilfenilsulfonilamino, alquilcarbonilamino, cicloalquenilcarbonilamino, fenilcarbonilamino, fenilalquilcarbonilamino, alquilaminoalquilamino, 7-bencil-4-oxo-5,6,7,8-tetrahidro-4H-pirido[3,4-d]pirimidín-3-ilo, alquilaminofenilo, alquilamino, hidroxialquilamino, carboxialquilamino, carboxilcicloalquilamino, alquilaminocarbonilalquilamino, aminocarbonil(alquil)amino, morfolinilcarbonilalquilamino, alquilpiperazinilcarbonilalquilamino, alquilaminosulfonilamino, alquilcarbonilaminofenilsulfonilamino, alquilaminocarbonilamino, aminocarbonilamino, morfolinilcarbonilamino, pirrolidinilcarbonilamino, piperdinilcarbonilamino, alquilpiperazinilcarbonilamino, fenilalquilaminocarbonilamino, halofenilcarbonilamino, halofenilaminocarbonilamino, pirazinilcarbonilamino, alquilpiperazinilo, pirrolidinilsulfonilo y alquilpirrolidinilaminosulfonilo, o una sal o éster farmacéuticamente aceptable de los mismos.
ARP110101228A 2010-04-14 2011-04-12 Derivados de 3,3-dimetil-tetrahidroquinolina, composiciones farmaceuticas que los contienen, metodo para prepararlos y uso de los mismos para el tratamiento de la diabetes, obesidad y dislipemia AR081072A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2010071760 2010-04-14

Publications (1)

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AR081072A1 true AR081072A1 (es) 2012-06-06

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Country Status (13)

Country Link
US (2) US8344137B2 (es)
EP (1) EP2558449B1 (es)
JP (1) JP2013523850A (es)
KR (1) KR101726469B1 (es)
AR (1) AR081072A1 (es)
BR (1) BR112012026338A2 (es)
CA (1) CA2795387C (es)
ES (1) ES2454866T3 (es)
HK (1) HK1176608A1 (es)
MX (1) MX2012011780A (es)
RU (1) RU2603276C2 (es)
TW (1) TW201139379A (es)
WO (1) WO2011128251A1 (es)

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EP2970177A1 (en) 2013-03-15 2016-01-20 Pfizer Inc. Indole compounds that activate ampk
CN103539381B (zh) * 2013-09-29 2015-04-08 北方工业大学 一种豆石混凝土用外加剂
WO2015103480A1 (en) 2014-01-02 2015-07-09 Massachusetts Eye & Ear Infirmary Treating ocular neovascularization
UA125245C2 (uk) 2014-10-06 2022-02-09 Вертекс Фармасьютикалз Інкорпорейтед Модулятори регулятора трансмембранної провідності при муковісцидозі
ITUB20151256A1 (it) 2015-05-28 2016-11-28 Olon Spa Processo industriale per la preparazione di enzalutamide
AU2017240685B2 (en) 2016-03-31 2021-08-12 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
PT3519401T (pt) 2016-09-30 2021-12-27 Vertex Pharma Modulador de regulador de condutância transmembranar de fibrose quística, composições farmacêuticas, métodos de tratamento e processo para fazer o modulador
PT3551622T (pt) 2016-12-09 2020-11-12 Vertex Pharma Modulador do regulador da condutância transmembrana da fibrose quística, composições farmacêuticas, métodos de tratamento e processo de fabrico do modulador
GB201622345D0 (en) * 2016-12-29 2017-02-15 Redag Crop Prot Ltd Agricultural chemicals
US11253509B2 (en) 2017-06-08 2022-02-22 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
WO2019018395A1 (en) 2017-07-17 2019-01-24 Vertex Pharmaceuticals Incorporated METHODS OF TREATING CYSTIC FIBROSIS
CN111051280B (zh) 2017-08-02 2023-12-22 弗特克斯药品有限公司 制备吡咯烷化合物的方法
EP3697774A1 (en) 2017-10-19 2020-08-26 Vertex Pharmaceuticals Incorporated Crystalline forms and compositions of cftr modulators
JP7245834B2 (ja) 2017-12-08 2023-03-24 バーテックス ファーマシューティカルズ インコーポレイテッド 嚢胞性線維症膜コンダクタンス制御因子のモジュレーターを作成するためのプロセス
TWI810243B (zh) 2018-02-05 2023-08-01 美商維泰克斯製藥公司 用於治療囊腫纖化症之醫藥組合物
US11414439B2 (en) 2018-04-13 2022-08-16 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
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CN116390925A (zh) 2020-06-26 2023-07-04 卡尔优普公司 Ampk活化剂

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CA2795387A1 (en) 2011-10-20
US20130023518A1 (en) 2013-01-24
TW201139379A (en) 2011-11-16
US20110257151A1 (en) 2011-10-20
JP2013523850A (ja) 2013-06-17
US8586747B2 (en) 2013-11-19
BR112012026338A2 (pt) 2016-07-19
MX2012011780A (es) 2012-11-16
RU2603276C2 (ru) 2016-11-27
EP2558449B1 (en) 2014-03-05
ES2454866T3 (es) 2014-04-11
EP2558449A1 (en) 2013-02-20
HK1176608A1 (en) 2013-08-02
KR20130066607A (ko) 2013-06-20
WO2011128251A1 (en) 2011-10-20
CA2795387C (en) 2018-01-02
KR101726469B1 (ko) 2017-04-12
US8344137B2 (en) 2013-01-01
RU2012146444A (ru) 2014-05-20

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