JP6438417B2 - スフィンゴミエリンおよびジヒドロスフィンゴミエリンの合成のための方法 - Google Patents

スフィンゴミエリンおよびジヒドロスフィンゴミエリンの合成のための方法 Download PDF

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JP6438417B2
JP6438417B2 JP2015562366A JP2015562366A JP6438417B2 JP 6438417 B2 JP6438417 B2 JP 6438417B2 JP 2015562366 A JP2015562366 A JP 2015562366A JP 2015562366 A JP2015562366 A JP 2015562366A JP 6438417 B2 JP6438417 B2 JP 6438417B2
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erythro
palmitoyl
benzoyl
acid
compound
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JP2016511281A (ja
JP2016511281A5 (OSRAM
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カルメン オニチュ，ダニエラ
カルメン オニチュ，ダニエラ
ヘッコフ，ステファン
オズワルト，ブノワ
レブマン，ピーター
ペール，アンドレアス
ゴンザレス，ミゲル
ザウター，パトリック
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セレニス セラピューティクス ホールディング エスアー
セレニス セラピューティクス ホールディング エスアー
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/24—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2015562366A 2013-03-15 2014-03-14 スフィンゴミエリンおよびジヒドロスフィンゴミエリンの合成のための方法 Active JP6438417B2 (ja)

Applications Claiming Priority (5)

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US201361801641P 2013-03-15 2013-03-15
US61/801,641 2013-03-15
EP13306056 2013-07-23
EP13306056.6 2013-07-23
PCT/IB2014/000494 WO2014140787A2 (en) 2013-03-15 2014-03-14 Methods for the synthesis of sphingomyelins and dihydrosphingomyelins

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JP2016511281A5 JP2016511281A5 (OSRAM) 2017-02-02
JP6438417B2 true JP6438417B2 (ja) 2018-12-12

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JP2018117808A Pending JP2018168171A (ja) 2013-03-15 2018-06-21 スフィンゴミエリンおよびジヒドロスフィンゴミエリンの合成のための方法

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US (3) US20140316154A1 (OSRAM)
EP (3) EP3363805B1 (OSRAM)
JP (2) JP6438417B2 (OSRAM)
KR (1) KR20150132188A (OSRAM)
CN (1) CN105051051B (OSRAM)
AU (2) AU2014229638B2 (OSRAM)
BR (1) BR112015023558A2 (OSRAM)
CA (1) CA2900902C (OSRAM)
DK (1) DK3363805T3 (OSRAM)
ES (1) ES3017659T3 (OSRAM)
HK (1) HK1214266A1 (OSRAM)
MX (1) MX387128B (OSRAM)
PH (1) PH12015501835B1 (OSRAM)
SG (2) SG10201804887YA (OSRAM)
WO (1) WO2014140787A2 (OSRAM)
ZA (1) ZA201505860B (OSRAM)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SMT201700203T1 (it) 2009-02-16 2017-05-08 Cerenis Therapeutics Holding Sa Mimetici di apolipoproteina a-i
SG2014012850A (en) 2010-10-18 2014-05-29 Cerenis Therapeutics Holding Sa Compounds, compositions and methods useful for cholesterol mobilisation
JP6438417B2 (ja) * 2013-03-15 2018-12-12 セレニス セラピューティクス ホールディング エスアー スフィンゴミエリンおよびジヒドロスフィンゴミエリンの合成のための方法
US9708354B2 (en) 2013-03-15 2017-07-18 Cerenis Therapeutics Holding Sa Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
WO2019030574A1 (en) 2017-08-10 2019-02-14 Cerenis Therapeutics Holding Cargomers
WO2019030575A1 (en) 2017-08-10 2019-02-14 Cerenis Therapeutics Holding APOMÈRES
EP3778611B1 (en) * 2018-03-27 2022-10-12 NOF Corporation Sphingomyelin-derived lipid and method for producing same
JP7303618B2 (ja) * 2018-10-05 2023-07-05 日本精化株式会社 スフィンゴリン脂質前駆体及びその製造方法、並びに、スフィンゴリン脂質の製造方法
WO2021209808A1 (en) 2020-04-16 2021-10-21 Abionyx Pharma Sa Cer-001 therapy for treating kidney disease
IL297046A (en) 2020-04-16 2022-12-01 Abionyx Pharma Sa Treatment of kidney disease using cer-001
CN115427064A (zh) 2020-04-16 2022-12-02 阿比奥尼克斯制药公司 使用基于脂质结合蛋白的复合物治疗急性病况的方法
EP4221686A2 (en) 2020-10-01 2023-08-09 Abionyx Pharma SA Compositions comprising lipid binding protein-based complexes for use for treating eye diseases
JP2024514154A (ja) 2021-04-15 2024-03-28 アビオニクス ファーマ エスエー 臓器保存溶液における脂質結合タンパク質ベースの複合体の使用
CA3247588A1 (en) 2022-04-06 2023-10-12 Abionyx Pharma Sa METHODS FOR TREATING LEUKOCYTOSIS, ENDOTHELIAL DYSFUNCTION AND CARDITIS USING LIPID-BINDING PROTEIN COMPLEXES
AU2023250345A1 (en) 2022-04-06 2024-11-14 Abionyx Pharma Sa Methods for treating eye diseases using lipid binding protein-based complexes
WO2023237927A2 (en) 2022-06-10 2023-12-14 Abionyx Pharma Sa Methods for treating hyperinflammatory conditions using lipid binding protein -based complexes
AU2023284357A1 (en) 2022-06-10 2025-01-23 Abionyx Pharma Sa Methods for treating acute conditions using lipid binding protein-based complexes
KR20250035547A (ko) 2022-06-28 2025-03-12 아비오닉스 파마 에스에이 스핑고미엘린의 합성을 위한 화합물 및 공정
IL322074A (en) 2023-01-13 2025-09-01 Abionyx Pharma Sa Treatment using a lipid-binding protein molecule
WO2025093929A1 (en) 2023-10-31 2025-05-08 Abionyx Pharma Sa Lipid binding protein molecule therapy

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0146810A3 (de) 1983-12-05 1987-05-13 Solco Basel AG Verfahren zur Herstellung von Sphingosinderivaten
US5220043A (en) * 1991-03-21 1993-06-15 Ohio University Synthesis of D-erythro-sphingomyelins
CN1099868C (zh) 1993-11-16 2003-01-29 斯卡法玛公司 具有控制释放活性成分作用的囊
US5766627A (en) 1993-11-16 1998-06-16 Depotech Multivescular liposomes with controlled release of encapsulated biologically active substances
CA2320117A1 (en) * 1998-02-12 1999-08-19 Emory University Sphingolipid derivatives and their methods of use
JP2004002215A (ja) * 2002-05-23 2004-01-08 National Institute Of Advanced Industrial & Technology スフィンゴ脂質誘導体の製造方法
EP1704155A1 (en) 2004-01-15 2006-09-27 Biolab Ltd. Sphingomyelin, intermediates thereof and methods for preparation of same
CA2566559C (en) 2004-05-17 2014-05-06 Inex Pharmaceuticals Corporation Liposomal formulations comprising dihydrosphingomyelin and methods of use thereof
CA2572310A1 (en) * 2004-06-29 2006-01-12 Jadolabs Gmbh Sphingolipid-derived pharmaceutical compositions
JP2006045113A (ja) 2004-08-04 2006-02-16 Kemikurea:Kk リン酸エステル類
JP4825947B2 (ja) 2004-08-04 2011-11-30 学校法人関西学院 不飽和アミノジオール類の製造方法
US8206750B2 (en) 2005-03-24 2012-06-26 Cerenis Therapeutics Holding S.A. Charged lipoprotein complexes and their uses
AR057456A1 (es) 2005-07-20 2007-12-05 Merck & Co Inc Inhibidores de la proteasa ns3 del vhc
JP2007204384A (ja) 2006-01-31 2007-08-16 Kemikurea:Kk 光学活性リン酸誘導体およびこれを用いた光学活性スフィンゴシン１−リン酸誘導体の製造方法
JP5429734B2 (ja) * 2007-02-09 2014-02-26 国立大学法人岐阜大学 スフィンゴ糖脂質の合成法
JP5178707B2 (ja) 2007-03-09 2013-04-10 株式会社糖鎖工学研究所 スフィンゴシン化合物、その製造方法及びスフィンゴミエリナーゼ阻害剤
CN102223878A (zh) 2008-10-07 2011-10-19 耶路撒冷希伯来大学伊森姆研究发展公司 包含鞘磷脂的脂质体系统
HUE042314T2 (hu) 2011-02-07 2019-06-28 Cerenis Therapeutics Holding Sa Lipoprotein komplexek és azok gyártása és alkalmazásai
FR3000959B1 (fr) * 2013-01-14 2015-08-21 Holis Technologies Nouveaux intermediaires de synthese permettant d'acceder avec de bons rendements a des derives de sphingosines, ceramides et sphingomyelines
US9708354B2 (en) 2013-03-15 2017-07-18 Cerenis Therapeutics Holding Sa Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
JP6438417B2 (ja) 2013-03-15 2018-12-12 セレニス セラピューティクス ホールディング エスアー スフィンゴミエリンおよびジヒドロスフィンゴミエリンの合成のための方法

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HK1214266A1 (zh) 2016-07-22
PH12015501835A1 (en) 2015-11-09
CA2900902A1 (en) 2014-09-18
MX2015012877A (es) 2016-02-03
EP3842443C0 (en) 2025-02-19
WO2014140787A2 (en) 2014-09-18
JP2016511281A (ja) 2016-04-14
US20140316154A1 (en) 2014-10-23
WO2014140787A3 (en) 2015-03-26
AU2014229638A1 (en) 2015-08-20
BR112015023558A2 (pt) 2017-07-18
EP3842443B1 (en) 2025-02-19
US20170204122A1 (en) 2017-07-20
HK1212705A1 (zh) 2016-06-17
CN105051051B (zh) 2021-07-16
SG10201804887YA (en) 2018-07-30
CA2900902C (en) 2022-08-02
EP3363805A1 (en) 2018-08-22
EP3842443A1 (en) 2021-06-30
SG11201506456VA (en) 2015-09-29
AU2018267598A1 (en) 2018-12-06
CN105051051A (zh) 2015-11-11
MX387128B (es) 2025-03-19
KR20150132188A (ko) 2015-11-25
ES3017659T3 (en) 2025-05-13
PH12015501835B1 (en) 2015-11-09
US20160075634A1 (en) 2016-03-17
DK3363805T3 (da) 2021-03-08
JP2018168171A (ja) 2018-11-01
EP3363805B1 (en) 2020-12-16
EP2970344A2 (en) 2016-01-20
AU2014229638B2 (en) 2018-09-06
US9643915B2 (en) 2017-05-09
ZA201505860B (en) 2017-11-29

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