AU2014229638B2 - Methods for the synthesis of sphingomyelins and dihydrosphingomyelins - Google Patents

Methods for the synthesis of sphingomyelins and dihydrosphingomyelins Download PDF

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Publication number
AU2014229638B2
AU2014229638B2 AU2014229638A AU2014229638A AU2014229638B2 AU 2014229638 B2 AU2014229638 B2 AU 2014229638B2 AU 2014229638 A AU2014229638 A AU 2014229638A AU 2014229638 A AU2014229638 A AU 2014229638A AU 2014229638 B2 AU2014229638 B2 AU 2014229638B2
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zro
compound
palmitoyl
benzoyl
eryi
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AU2014229638A1 (en
Inventor
Miguel Gonzalez
Stefan HECKHOFF
Daniela Carmen Oniciu
Benoit OSWALD
Andreas PEER
Peter Rebmann
Patrik SAUTER
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Abionyx Pharma SA
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Cerenis Therapeutics Holding SA
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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
    • 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
    • C07F9/10—Phosphatides, e.g. lecithin
    • 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)
AU2014229638A 2013-03-15 2014-03-14 Methods for the synthesis of sphingomyelins and dihydrosphingomyelins Active AU2014229638B2 (en)

Priority Applications (1)

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AU2018267598A AU2018267598A1 (en) 2013-03-15 2018-11-21 Methods for the synthesis of sphingomyelins and dihydrosphingomyelins

Applications Claiming Priority (5)

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US201361801641P 2013-03-15 2013-03-15
US61/801,641 2013-03-15
EP13306056.6 2013-07-23
EP13306056 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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AU2014229638B2 true AU2014229638B2 (en) 2018-09-06

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US (3) US20140316154A1 (cg-RX-API-DMAC10.html)
EP (3) EP3363805B1 (cg-RX-API-DMAC10.html)
JP (2) JP6438417B2 (cg-RX-API-DMAC10.html)
KR (1) KR20150132188A (cg-RX-API-DMAC10.html)
CN (1) CN105051051B (cg-RX-API-DMAC10.html)
AU (2) AU2014229638B2 (cg-RX-API-DMAC10.html)
BR (1) BR112015023558A2 (cg-RX-API-DMAC10.html)
CA (1) CA2900902C (cg-RX-API-DMAC10.html)
DK (1) DK3363805T3 (cg-RX-API-DMAC10.html)
ES (1) ES3017659T3 (cg-RX-API-DMAC10.html)
HK (1) HK1214266A1 (cg-RX-API-DMAC10.html)
MX (1) MX387128B (cg-RX-API-DMAC10.html)
PH (1) PH12015501835A1 (cg-RX-API-DMAC10.html)
SG (2) SG11201506456VA (cg-RX-API-DMAC10.html)
WO (1) WO2014140787A2 (cg-RX-API-DMAC10.html)
ZA (1) ZA201505860B (cg-RX-API-DMAC10.html)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2011008599A (es) 2009-02-16 2011-11-18 Cerenis Therapeutics Sa Peptidos mimeticos de la apolipoproteina a-i.
HRP20171587T1 (hr) 2010-10-18 2017-12-01 Cerenis Therapeutics Holding Sa Spojevi, pripravci i postupci pogodni za mobilizaciju kolesterola
US9708354B2 (en) 2013-03-15 2017-07-18 Cerenis Therapeutics Holding Sa Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
SG11201506456VA (en) * 2013-03-15 2015-09-29 Cerenis Therapeutics Holding Sa Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
US20190046608A1 (en) 2017-08-10 2019-02-14 Cerenis Therapeutics Holding Sa Apomers
TW201919712A (zh) 2017-08-10 2019-06-01 法商塞勒尼斯醫療控股公司 運送子(cargomers)
CN111757886A (zh) * 2018-03-27 2020-10-09 日油株式会社 鞘磷脂衍生的脂质及其生产方法
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
KR20230004605A (ko) 2020-04-16 2023-01-06 아비오닉스 파마 에스에이 지질 결합 단백질-기반 복합체를 사용하여 급성 상태를 치료하는 방법
AU2021254856A1 (en) 2020-04-16 2022-11-10 Abionyx Pharma Sa CER-001 therapy for treating kidney disease
CA3197168A1 (en) 2020-10-01 2022-04-07 Abionyx Pharma Sa Methods for treating eye diseases using lipid binding protein-based complexes
CA3216226A1 (en) 2021-04-15 2022-10-20 Abionyx Pharma Sa Use of lipid binding protein-based complexes in organ preservation solutions
US20250230208A1 (en) 2022-04-06 2025-07-17 Abionyx Pharma Sa Methods for treating eye diseases using lipid binding protein-based complexes
CN119317440A (zh) 2022-04-06 2025-01-14 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白细胞增多、内皮功能障碍和心脏炎的方法
WO2023237935A2 (en) 2022-06-10 2023-12-14 Abionyx Pharma Sa Methods for treating acute conditions using lipid binding protein-based complexes
CA3258787A1 (en) 2022-06-10 2023-12-14 Abionyx Pharma Sa METHODS OF TREATMENT OF HYPERINFLAMMATORY DISEASES USING LIPID-BINDING PROTEIN COMPLEXES
IL317896A (en) 2022-06-28 2025-02-01 Abionyx Pharma Sa Compounds and processes for the synthesis of sphingomyelins
KR20260010675A (ko) 2023-01-13 2026-01-21 아비오닉스 파마 에스에이 지질 결합 단백질 분자 치료
IL327995A (en) 2023-10-31 2026-06-01 Abionyx Pharma Sa Lipid binding protein molecule therapy

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5220043A (en) * 1991-03-21 1993-06-15 Ohio University Synthesis of D-erythro-sphingomyelins
WO2014108564A1 (fr) * 2013-01-14 2014-07-17 M2I Development Nouveaux intermédiaires de synthèse permettant d'accéder avec de bons rendements à des dérivés de sphingosines, céramides et sphingomyelines

Family Cites Families (19)

* 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
US5766627A (en) 1993-11-16 1998-06-16 Depotech Multivescular liposomes with controlled release of encapsulated biologically active substances
HUT75162A (en) 1993-11-16 1997-04-28 Depotech Corp Vesicles with controlled release of actives
EP1053243B1 (en) 1998-02-12 2011-03-30 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
WO2005068480A1 (en) 2004-01-15 2005-07-28 Biolab Ltd. Sphingomyelin, intermediates thereof and methods for preparation of same
AU2005251691A1 (en) 2004-05-17 2005-12-22 Tekmira Pharmaceuticals Corporation Liposomal formulations comprising dihydrosphingomyelin and methods of use thereof
ES2317259T3 (es) * 2004-06-29 2009-04-16 Jado Technologies Gmbh Esfingolipidos contra procesos patologicos en baldas lipidicas.
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
WO2008096880A1 (ja) * 2007-02-09 2008-08-14 Gifu University スフィンゴ糖脂質の合成法
WO2008111450A1 (ja) 2007-03-09 2008-09-18 Otsuka Chemical Co., Ltd. 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
WO2010041255A2 (en) 2008-10-07 2010-04-15 Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. Liposomal systems comprising sphingomyelin
LT2673296T (lt) 2011-02-07 2019-02-25 Cerenis Therapeutics Holding Sa Lipoproteino kompleksai ir jų gamyba ir jų panaudojimai
US9708354B2 (en) 2013-03-15 2017-07-18 Cerenis Therapeutics Holding Sa Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
SG11201506456VA (en) 2013-03-15 2015-09-29 Cerenis Therapeutics Holding Sa Methods for the synthesis of sphingomyelins and dihydrosphingomyelins

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5220043A (en) * 1991-03-21 1993-06-15 Ohio University Synthesis of D-erythro-sphingomyelins
WO2014108564A1 (fr) * 2013-01-14 2014-07-17 M2I Development Nouveaux intermédiaires de synthèse permettant d'accéder avec de bons rendements à des dérivés de sphingosines, céramides et sphingomyelines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Murakami, M. et al ., "An Efficient Synthesis of Short-chain Sphingomyelin Analogs and Their Susceptibility to Hydrolysis Catalyzed by Sphingomyelinase", Bioorganic & Medicinal Chemistry Letters, 1997, Vol. 7, No. 13, pages 1725-1728. *
Weiss A., "New approaches to synthesis of stereospeci¿c sphingomyelin", Chemistry and Physics of Lipids, 1999, Vol. 102 pages 3-12. *

Also Published As

Publication number Publication date
KR20150132188A (ko) 2015-11-25
EP3363805B1 (en) 2020-12-16
MX387128B (es) 2025-03-19
CA2900902A1 (en) 2014-09-18
EP3363805A1 (en) 2018-08-22
EP3842443A1 (en) 2021-06-30
PH12015501835B1 (en) 2015-11-09
HK1214266A1 (zh) 2016-07-22
SG10201804887YA (en) 2018-07-30
CA2900902C (en) 2022-08-02
EP2970344A2 (en) 2016-01-20
US20170204122A1 (en) 2017-07-20
CN105051051A (zh) 2015-11-11
MX2015012877A (es) 2016-02-03
JP6438417B2 (ja) 2018-12-12
US20140316154A1 (en) 2014-10-23
ES3017659T3 (en) 2025-05-13
WO2014140787A3 (en) 2015-03-26
EP3842443C0 (en) 2025-02-19
DK3363805T3 (da) 2021-03-08
CN105051051B (zh) 2021-07-16
JP2016511281A (ja) 2016-04-14
EP3842443B1 (en) 2025-02-19
HK1212705A1 (zh) 2016-06-17
AU2014229638A1 (en) 2015-08-20
BR112015023558A2 (pt) 2017-07-18
AU2018267598A1 (en) 2018-12-06
ZA201505860B (en) 2017-11-29
JP2018168171A (ja) 2018-11-01
SG11201506456VA (en) 2015-09-29
US20160075634A1 (en) 2016-03-17
US9643915B2 (en) 2017-05-09
PH12015501835A1 (en) 2015-11-09
WO2014140787A2 (en) 2014-09-18

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