AU2003295219B2 - Synthesis of (R) and (S)-aminocarnitine and derivatives thereof from D-and L-aspartic acid - Google Patents

Synthesis of (R) and (S)-aminocarnitine and derivatives thereof from D-and L-aspartic acid Download PDF

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Publication number
AU2003295219B2
AU2003295219B2 AU2003295219A AU2003295219A AU2003295219B2 AU 2003295219 B2 AU2003295219 B2 AU 2003295219B2 AU 2003295219 A AU2003295219 A AU 2003295219A AU 2003295219 A AU2003295219 A AU 2003295219A AU 2003295219 B2 AU2003295219 B2 AU 2003295219B2
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AU
Australia
Prior art keywords
group
aminocarnitine
process according
yield
acid
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.)
Ceased
Application number
AU2003295219A
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English (en)
Other versions
AU2003295219A1 (en
Inventor
Francesco De Angelis
Natalina Dell'uomo
Fabio Giannessi
Maria Ornella Tinti
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.)
Sigma Tau Industrie Farmaceutiche Riunite SpA
Original Assignee
Sigma Tau Industrie Farmaceutiche Riunite SpA
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
Priority claimed from US10/338,045 external-priority patent/US20030153783A1/en
Application filed by Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA
Publication of AU2003295219A1 publication Critical patent/AU2003295219A1/en
Application granted granted Critical
Publication of AU2003295219B2 publication Critical patent/AU2003295219B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • 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
    • A61P3/08—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Obesity (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
AU2003295219A 2003-01-08 2003-12-19 Synthesis of (R) and (S)-aminocarnitine and derivatives thereof from D-and L-aspartic acid Ceased AU2003295219B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10/338,045 US20030153783A1 (en) 1999-06-30 2003-01-08 Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid
US10/338,045 2003-01-08
US10/372,627 2003-02-25
US10/372,627 US6822115B2 (en) 1999-06-30 2003-02-25 Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid
PCT/IT2003/000846 WO2004063143A1 (en) 2003-01-08 2003-12-19 Synthesis fo (r) and (s)-aminocarnitine and derivatives thereof from d-and l-aspartic acid

Publications (2)

Publication Number Publication Date
AU2003295219A1 AU2003295219A1 (en) 2004-08-10
AU2003295219B2 true AU2003295219B2 (en) 2010-08-12

Family

ID=32716886

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2003295219A Ceased AU2003295219B2 (en) 2003-01-08 2003-12-19 Synthesis of (R) and (S)-aminocarnitine and derivatives thereof from D-and L-aspartic acid

Country Status (18)

Country Link
US (1) US6822115B2 (enExample)
EP (1) EP1581475B1 (enExample)
JP (1) JP4642476B2 (enExample)
KR (1) KR20050092398A (enExample)
CN (1) CN1735588B (enExample)
AT (1) ATE443039T1 (enExample)
AU (1) AU2003295219B2 (enExample)
BR (1) BR0317956A (enExample)
CA (1) CA2512679A1 (enExample)
CY (1) CY1109545T1 (enExample)
DE (1) DE60329325D1 (enExample)
DK (1) DK1581475T3 (enExample)
ES (1) ES2333523T3 (enExample)
MX (1) MXPA05007315A (enExample)
PL (1) PL378538A1 (enExample)
PT (1) PT1581475E (enExample)
SI (1) SI1581475T1 (enExample)
WO (1) WO2004063143A1 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1299266B1 (it) * 1998-05-15 2000-02-29 Sigma Tau Ind Farmaceuti Inibitori reversibili della carnitina palmitoil trasferasi
ITRM20050090A1 (it) * 2005-03-02 2006-09-03 Sigma Tau Ind Farmaceutiche Riunite Spa Derivati dell'acido ammino-butanoico inibitore della cpt.
US7776915B2 (en) * 2005-03-24 2010-08-17 Tracie Martyn International, Llc Topical formulations and methods of use
CA2680366C (en) * 2007-03-09 2016-06-21 University Health Network Inhibitors of carnitine palmitoyltransferase and treating cancer
WO2009015485A1 (en) * 2007-08-01 2009-02-05 University Health Network Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer
CN115974742A (zh) * 2023-02-16 2023-04-18 中国水产科学研究院黄海水产研究所 温和条件下dmshb的制备与结构表征方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002341A1 (en) * 1999-06-30 2001-01-11 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Synthesis of (r) and (s)-aminocarnitine and their derivatives starting from d- and l-aspartic acid

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1136945B (it) * 1981-03-18 1986-09-03 Anic Spa Processo per la preparazione di l-carnitina
IT1261489B (it) 1993-07-29 1996-05-23 Sigma Tau Ind Farmaceuti Procedimento per la produzione di r amminocarnitina e s amminocarnitina.
IT1299266B1 (it) * 1998-05-15 2000-02-29 Sigma Tau Ind Farmaceuti Inibitori reversibili della carnitina palmitoil trasferasi
US20030153783A1 (en) * 1999-06-30 2003-08-14 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002341A1 (en) * 1999-06-30 2001-01-11 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Synthesis of (r) and (s)-aminocarnitine and their derivatives starting from d- and l-aspartic acid

Also Published As

Publication number Publication date
ES2333523T3 (es) 2010-02-23
KR20050092398A (ko) 2005-09-21
PL378538A1 (pl) 2006-05-02
CY1109545T1 (el) 2014-08-13
EP1581475B1 (en) 2009-09-16
HK1086254A1 (en) 2006-09-15
SI1581475T1 (sl) 2009-12-31
DK1581475T3 (da) 2010-01-25
PT1581475E (pt) 2009-11-09
CN1735588A (zh) 2006-02-15
MXPA05007315A (es) 2005-09-30
BR0317956A (pt) 2006-06-13
CN1735588B (zh) 2010-05-26
US20030153784A1 (en) 2003-08-14
JP4642476B2 (ja) 2011-03-02
AU2003295219A1 (en) 2004-08-10
WO2004063143A1 (en) 2004-07-29
CA2512679A1 (en) 2004-07-29
US6822115B2 (en) 2004-11-23
DE60329325D1 (de) 2009-10-29
EP1581475A1 (en) 2005-10-05
ATE443039T1 (de) 2009-10-15
JP2006513243A (ja) 2006-04-20

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Legal Events

Date Code Title Description
DA2 Applications for amendment section 104

Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE INVENTION TITLE TO READ SYNTHESIS OF (R) AND (S)-AMINOCARNITINE AND DERIVATIVES THEREOF FROM D-AND L-ASPARTIC ACID.

DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE INVENTION TITLE TO READ SYNTHESIS OF (R) AND (S)-AMINOCARNITINE AND DERIVATIVES THEREOF FROM D-AND L-ASPARTIC ACID

FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired