CR20180201A - Modularores del receptor x farnesoide - Google Patents

Modularores del receptor x farnesoide

Info

Publication number
CR20180201A
CR20180201A CR20180201A CR20180201A CR20180201A CR 20180201 A CR20180201 A CR 20180201A CR 20180201 A CR20180201 A CR 20180201A CR 20180201 A CR20180201 A CR 20180201A CR 20180201 A CR20180201 A CR 20180201A
Authority
CR
Costa Rica
Prior art keywords
modulars
farnesoid
receiver
present
solvate
Prior art date
Application number
CR20180201A
Other languages
English (en)
Inventor
Roberto; Pellicciari
Antimo; Gioiello
Original Assignee
Intercept Pharmaceuticals Inc
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 Intercept Pharmaceuticals Inc filed Critical Intercept Pharmaceuticals Inc
Publication of CR20180201A publication Critical patent/CR20180201A/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • 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
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
    • C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Toxicology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Oncology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Transplantation (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Communicable Diseases (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Liquid Crystal Substances (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La presente solicitud proporciona un compuesto de fórmula I: o una sal, solvato o conjugado con aminoácidos farmacéuticamente aceptable del mismo en donde R1-R10, m, n, p, 5 y son como se describen en el presente documento. La presente invención se refiere, en general, a moduladores de FXR y a métodos para producir y usar dichos compuestos
CR20180201A 2015-10-07 2016-10-07 Modularores del receptor x farnesoide CR20180201A (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562238246P 2015-10-07 2015-10-07
PCT/US2016/055980 WO2017062763A1 (en) 2015-10-07 2016-10-07 Farnesoid x receptor modulators

Publications (1)

Publication Number Publication Date
CR20180201A true CR20180201A (es) 2018-08-24

Family

ID=58488545

Family Applications (1)

Application Number Title Priority Date Filing Date
CR20180201A CR20180201A (es) 2015-10-07 2016-10-07 Modularores del receptor x farnesoide

Country Status (27)

Country Link
US (2) US11034717B2 (es)
EP (2) EP3359160B1 (es)
JP (2) JP7021080B2 (es)
KR (1) KR20180061351A (es)
CN (1) CN108348530B (es)
AR (1) AR106293A1 (es)
AU (1) AU2016335765B2 (es)
BR (1) BR112018006892B1 (es)
CA (1) CA3000881C (es)
CL (1) CL2018000883A1 (es)
CO (1) CO2018003728A2 (es)
CR (1) CR20180201A (es)
DK (1) DK3359160T3 (es)
EA (1) EA038665B1 (es)
EC (1) ECSP18030284A (es)
ES (1) ES2898705T3 (es)
HK (1) HK1253558A1 (es)
IL (1) IL258359B2 (es)
MA (2) MA45761A (es)
MX (1) MX2018004186A (es)
PH (1) PH12018500777A1 (es)
SV (1) SV2018005662A (es)
TN (1) TN2018000106A1 (es)
TW (1) TW201718621A (es)
UA (1) UA123948C2 (es)
WO (1) WO2017062763A1 (es)
ZA (1) ZA201802901B (es)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG11201703717SA (en) 2014-11-06 2017-06-29 Enanta Pharm Inc Bile acid analogs an fxr/tgr5 agonists and methods of use thereof
US11578097B2 (en) 2014-11-26 2023-02-14 Enanta Pharmaceuticals, Inc. Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof
US10208081B2 (en) 2014-11-26 2019-02-19 Enanta Pharmaceuticals, Inc. Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof
CN107231795A (zh) 2014-11-26 2017-10-03 英安塔制药有限公司 作为fxr/tgr5激动剂的胆汁酸类似物及其使用方法
JP2018505190A (ja) 2015-02-11 2018-02-22 エナンタ ファーマシューティカルズ インコーポレイテッド Ｆｘｒ／ｔｇｒ５アゴニストとしての胆汁酸類似体およびその使用方法
SG10201910670RA (en) 2015-03-31 2020-01-30 Enanta Pharm Inc Bile acid derivatives as fxr/tgr5 agonists and methods of use thereof
US11034717B2 (en) 2015-10-07 2021-06-15 Intercept Pharmaceuticals, Inc. Farnesoid X receptor modulators
WO2017147159A1 (en) 2016-02-23 2017-08-31 Enanta Pharmaceuticals, Inc. Deuterated bile acid derivatives as fxr/tgr5 agonists and methods of use thereof
US10323060B2 (en) 2016-02-23 2019-06-18 Enanta Pharmaceuticals, Inc. Benzoic acid derivatives of bile acid as FXR/TGR5 agonists and methods of use thereof
US10323061B2 (en) 2016-02-23 2019-06-18 Enanta Pharmaceuticals, Inc. Heteroaryl containing bile acid analogs as FXR/TGR5 agonists and methods of use thereof
JP7057783B2 (ja) 2016-11-29 2022-04-20 エナンタ ファーマシューティカルズ インコーポレイテッド スルホニル尿素胆汁酸誘導体の調製方法
US10472386B2 (en) 2017-02-14 2019-11-12 Enanta Pharmaceuticals, Inc. Bile acid derivatives as FXR agonists and methods of use thereof
US10676500B2 (en) 2017-04-07 2020-06-09 Enanta Pharmaceuticals, Inc. Process for preparation of sulfonyl carbamate bile acid derivatives
EP3642217A4 (en) * 2017-06-23 2021-06-16 Intercept Pharmaceuticals, Inc. PROCESS AND INTERMEDIATE PRODUCTS FOR THE MANUFACTURING OF BALIC ACID DERIVATIVES
BR112020001362A2 (pt) 2017-07-24 2020-08-11 Intercept Pharmaceuticals, Inc. derivados de ácido biliar isotopicamente marcados
CN109929005B (zh) * 2017-12-19 2020-10-30 西安奥立泰医药科技有限公司 用于代谢性疾病治疗的化合物及其制备方法和应用
GB201812382D0 (en) 2018-07-30 2018-09-12 Nzp Uk Ltd Compounds
BR112021024109A2 (pt) 2019-05-30 2022-03-22 Intercept Pharmaceuticals Inc Composições farmacêuticas compreendendo um agonista fxr e um fibrato para uso no tratamento de doença hepática colestática
WO2023288123A1 (en) 2021-07-16 2023-01-19 Interecept Pharmaceuticals, Inc. Methods and intermediates for the preparation of 3.alpha.,7.alpha.,11.beta.-trihydroxy-6.alpha.-ethyl-5.beta.-cholan-24-oic acid

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US2599481A (en) 1948-09-28 1952-06-03 Ciba Pharm Prod Inc Reduction of steroid epoxides
DE3366932D1 (en) * 1982-07-29 1986-11-20 Lehner Ag New derivatives of biliary acids, process for the production thereof and pharmaceutical compositions containing the same
IT1223313B (it) 1987-10-20 1990-09-19 Gipharmex Spa Derivati di acidi biliari loro preparazione e composizioni farmaceutiche che li contengono
DE10113257C1 (de) 2001-03-19 2002-11-14 Inst Mikrotechnik Mainz Gmbh Elektrophoresevorrichtung und ihre Verwendung
US20070197484A1 (en) 2001-05-03 2007-08-23 Ching Song Method of treating disorder related to high cholesterol concentration
EP2040713B1 (en) 2006-06-27 2014-06-18 Intercept Pharmaceuticals Inc. Bile acid derivatives as fxr ligands for the prevention or treatment of fxr-mediated deseases or conditions
EA030681B1 (ru) * 2008-11-19 2018-09-28 Интерсепт Фармасьютикалз, Инк. Модуляторы tgr5 и способы их применения
BR122016011808B1 (pt) 2012-06-19 2021-09-21 Intercept Pharmaceuticals, Inc Processos para preparar a forma 1 de ácido obeticólico e o ácido obeticólico cristalino
KR102106186B1 (ko) * 2012-11-28 2020-05-04 인터셉트 파마슈티컬즈, 인크. 폐 질환의 치료
DK3360881T3 (da) * 2013-05-14 2021-03-15 Intercept Pharmaceuticals Inc 11-hydroxy-6-substituerede derivater af galdesyrer og aminosyrekonjagater deraf som farnesoid X receptormodulatorer
US9351083B2 (en) 2013-10-17 2016-05-24 Turtle Beach Corporation Transparent parametric emitter
CN107231795A (zh) * 2014-11-26 2017-10-03 英安塔制药有限公司 作为fxr/tgr5激动剂的胆汁酸类似物及其使用方法
US11578097B2 (en) * 2014-11-26 2023-02-14 Enanta Pharmaceuticals, Inc. Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof
TR201804712T1 (tr) 2015-10-07 2018-04-24 Stoller Ets Diasil veya diaril üre ve en az bir metal kompleksi içeren bir sinerjistik tarımsal formül kullanılarak bitkilerdeki etilenin yönetimi.
US11034717B2 (en) * 2015-10-07 2021-06-15 Intercept Pharmaceuticals, Inc. Farnesoid X receptor modulators
MX2018010983A (es) 2016-03-11 2019-01-21 Intercept Pharmaceuticals Inc Derivado de 3-desoxi y composiciones farmaceuticas del mismo.
EP3642217A4 (en) * 2017-06-23 2021-06-16 Intercept Pharmaceuticals, Inc. PROCESS AND INTERMEDIATE PRODUCTS FOR THE MANUFACTURING OF BALIC ACID DERIVATIVES

Also Published As

Publication number Publication date
EP3359160A1 (en) 2018-08-15
CA3000881C (en) 2024-03-19
JP7021080B2 (ja) 2022-02-16
ECSP18030284A (es) 2018-05-31
EP3359160B1 (en) 2021-08-25
US11034717B2 (en) 2021-06-15
WO2017062763A1 (en) 2017-04-13
CN108348530B (zh) 2023-09-29
CN108348530A (zh) 2018-07-31
IL258359B2 (en) 2023-11-01
IL258359B1 (en) 2023-07-01
EP3981779A1 (en) 2022-04-13
US20210269475A1 (en) 2021-09-02
US20170101434A1 (en) 2017-04-13
MA42339A1 (fr) 2019-01-31
PH12018500777A1 (en) 2018-10-29
ZA201802901B (en) 2019-07-31
KR20180061351A (ko) 2018-06-07
EA038665B1 (ru) 2021-09-30
SV2018005662A (es) 2018-12-14
HK1253558A1 (zh) 2019-06-21
JP2019210297A (ja) 2019-12-12
CO2018003728A2 (es) 2018-07-31
UA123948C2 (uk) 2021-06-30
EP3359160A4 (en) 2019-06-05
BR112018006892B1 (pt) 2023-04-11
AR106293A1 (es) 2018-01-03
DK3359160T3 (da) 2021-11-22
TW201718621A (zh) 2017-06-01
ES2898705T3 (es) 2022-03-08
CA3000881A1 (en) 2017-04-13
EA201890899A1 (ru) 2018-09-28
TN2018000106A1 (en) 2019-10-04
AU2016335765A1 (en) 2018-04-19
BR112018006892A2 (pt) 2018-10-16
AU2016335765B2 (en) 2022-01-06
MX2018004186A (es) 2018-05-17
CL2018000883A1 (es) 2018-06-29
IL258359A (en) 2018-06-28
JP2018530559A (ja) 2018-10-18
MA45761A (fr) 2021-04-21

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