WO2008110941A3 - New process of synthesis of a squalamine and/or trodusquemine precursor - Google Patents

New process of synthesis of a squalamine and/or trodusquemine precursor Download PDF

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Publication number
WO2008110941A3
WO2008110941A3 PCT/IB2008/001730 IB2008001730W WO2008110941A3 WO 2008110941 A3 WO2008110941 A3 WO 2008110941A3 IB 2008001730 W IB2008001730 W IB 2008001730W WO 2008110941 A3 WO2008110941 A3 WO 2008110941A3
Authority
WO
WIPO (PCT)
Prior art keywords
trodusquemine
squalamine
precursor
synthesis
new process
Prior art date
Application number
PCT/IB2008/001730
Other languages
French (fr)
Other versions
WO2008110941A2 (en
Inventor
Jean Michel Brunel
Nicolas Vidal
Jean-Marie Pages
Yves Letourneux
Original Assignee
Univ Aix Marseille Ii
Jean Michel Brunel
Nicolas Vidal
Jean-Marie Pages
Yves Letourneux
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 Univ Aix Marseille Ii, Jean Michel Brunel, Nicolas Vidal, Jean-Marie Pages, Yves Letourneux filed Critical Univ Aix Marseille Ii
Publication of WO2008110941A2 publication Critical patent/WO2008110941A2/en
Publication of WO2008110941A3 publication Critical patent/WO2008110941A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention relates to a new process of synthesis of a squalamine and/or trodusquemine precursor like 24-substituted oxy-7-substitutedoxycholestan-3- one, preferably of 24β-benzoyloxy-7α-hydroxycholestan-3-one.
PCT/IB2008/001730 2007-03-14 2008-03-14 New process of synthesis of a squalamine and/or trodusquemine precursor WO2008110941A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90685607P 2007-03-14 2007-03-14
US60/906,856 2007-03-14

Publications (2)

Publication Number Publication Date
WO2008110941A2 WO2008110941A2 (en) 2008-09-18
WO2008110941A3 true WO2008110941A3 (en) 2009-05-22

Family

ID=39760170

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2008/001730 WO2008110941A2 (en) 2007-03-14 2008-03-14 New process of synthesis of a squalamine and/or trodusquemine precursor

Country Status (1)

Country Link
WO (1) WO2008110941A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6434916B2 (en) 2012-12-20 2018-12-05 マウント デザート アイランド バイオロジカル ラボラトリー Stimulation and promotion of tissue regeneration
KR20160024930A (en) * 2013-06-28 2016-03-07 시노팜 타이완 리미티드 Process for the preparation of abiraterone and intermediates thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019366A1 (en) * 1993-02-26 1994-09-01 Magainin Pharmaceuticals Inc. Chemical synthesis of squalamine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019366A1 (en) * 1993-02-26 1994-09-01 Magainin Pharmaceuticals Inc. Chemical synthesis of squalamine

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
MORIARTY R M ET AL: "SYNTHESIS OF SQUALAMINE.A STEROIDAL ANTIBIOTIC FROM THE SHARK", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 35, no. 44, 31 October 1994 (1994-10-31), pages 8103 - 8106, XP000572370, ISSN: 0040-4039 *
OKUMURA, KAZUO ET AL: "Formal synthesis of squalamine from desmosterol", CHEMICAL & PHARMACEUTICAL BULLETIN , 51(10), 1177-1182 CODEN: CPBTAL; ISSN: 0009-2363, 2003, XP002516638 *
ORSINI F ET AL: "Pd(0)-MEDIATED CROSS-COUPLING OF REFORMATSKY REAGENTS WITH VINYL- AND ARYL TRIFLATES", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS, PHILADELPHIA, PA, vol. 17, no. 12, 1 January 1987 (1987-01-01), pages 1389 - 1402, XP003020475, ISSN: 0039-7911 *
TAKAGI, JUN; TAKAHASHI, KOU; ISHIYAMA, TATSUO; MIYAURA, NORIO: "Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides or Triflates: Convenient Synthesis of Unsymmetrical 1,3-Dienes via the Borylation-Coupling Sequence", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 27, 2002, pages 8001 - 8006, XP002516639 *

Also Published As

Publication number Publication date
WO2008110941A2 (en) 2008-09-18

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