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WO2003097668A3 - Nouveau procede de production de l'octreotide, analogue de la somatostatine - Google Patents

Nouveau procede de production de l'octreotide, analogue de la somatostatine Download PDF

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Publication number
WO2003097668A3
WO2003097668A3 PCT/IN2003/000160 IN0300160W WO03097668A3 WO 2003097668 A3 WO2003097668 A3 WO 2003097668A3 IN 0300160 W IN0300160 W IN 0300160W WO 03097668 A3 WO03097668 A3 WO 03097668A3
Authority
WO
WIPO (PCT)
Prior art keywords
octreotide
acm
thr
alcohol
cys
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
PCT/IN2003/000160
Other languages
English (en)
Other versions
WO2003097668A2 (fr
Inventor
Nishith C Chaturvedi
Suresh Beri
Ravindra D Yeole
Souza Noel J De
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.)
Individual
Original Assignee
Individual
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 US10/153,555 external-priority patent/US6987167B2/en
Application filed by Individual filed Critical Individual
Priority to AU2003245030A priority Critical patent/AU2003245030A1/en
Priority to EP03738490A priority patent/EP1506219A2/fr
Publication of WO2003097668A2 publication Critical patent/WO2003097668A2/fr
Publication of WO2003097668A3 publication Critical patent/WO2003097668A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/655—Somatostatins
    • C07K14/6555—Somatostatins at least 1 amino acid in D-form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Endocrinology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La présente invention se rapporte à un procédé de production commerciale d'octréotide par recours à la chimie des peptides en solution et au moyen de dérivés d'acides aminés peu coûteux. Ainsi, l'hexapeptide (Boc) D-Phe-Cys(Acm)-Phe-D-Trp-Lys(Boc)-Thr-OMe est synthétisé par condensation de deux fragments tripeptidiques, saponifié et condensé avec Cys(Acm)-Thr-OL aux fins de la production de l'alcool octapeptidique linéaire. Cet alcool peptidique linéaire est traité avec de l'iode, après retrait des groupes Boc, aux fins de la production de l'octréotide peptidique cyclique. L'alcool octapeptidique linéaire peut également être fabriqué par condensation de l'acide hexapeptidique protégé avec le dipeptide Cys(Acm)-Thr-OMe, puis par réduction avec du borohydrure de sodium.
PCT/IN2003/000160 2002-05-22 2003-04-16 Nouveau procede de production de l'octreotide, analogue de la somatostatine Ceased WO2003097668A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003245030A AU2003245030A1 (en) 2002-05-22 2003-04-16 Novel process for production of the somatostatin analog, octreotide
EP03738490A EP1506219A2 (fr) 2002-05-22 2003-04-16 Nouveau procede de production de l'octreotide, analogue de la somatostatine

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US10/153,555 2002-05-22
US10/153,555 US6987167B2 (en) 2002-05-22 2002-05-22 Process for production of the somatostatin analog, octreotide
IN460MU2002 2002-05-24
IN460/MUM/2002 2002-05-24

Publications (2)

Publication Number Publication Date
WO2003097668A2 WO2003097668A2 (fr) 2003-11-27
WO2003097668A3 true WO2003097668A3 (fr) 2004-03-25

Family

ID=29551480

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000160 Ceased WO2003097668A2 (fr) 2002-05-22 2003-04-16 Nouveau procede de production de l'octreotide, analogue de la somatostatine

Country Status (3)

Country Link
EP (1) EP1506219A2 (fr)
AU (1) AU2003245030A1 (fr)
WO (1) WO2003097668A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2458084A1 (fr) * 2004-03-12 2005-09-12 Dalton Chemical Laboratories Inc. Nouvelle methode de synthese de l'octreotide
US8377891B2 (en) 2008-11-07 2013-02-19 Usv, Ltd. Process for synthesis of cyclic octapeptide
RU2435780C1 (ru) * 2010-07-08 2011-12-10 Закрытое Акционерное Общество "Фарм-Синтез" Способ получения циклического пептида - октреотида
WO2013132505A1 (fr) 2012-03-09 2013-09-12 Natco Pharma Limited Procédé amélioré pour la préparation d'octréotide par une synthèse peptidique en phase solution

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ARANO Y ET AL: "Conventional and high yield synthesis of DTPA-conjugated peptides: Application of a monoreactive DTPA to DTPA-D-Phe-octreotide synthesis", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 8, 1997, pages 442 - 446, XP002149489, ISSN: 1043-1802 *
KROIS DANIEL ET AL: "Synthesis of N-alpha-(6-hydrazinonicotinoyl)-octreotide: A precursor of a (99mTc) complex.", LIEBIGS ANNALEN, no. 9, 1996, pages 1463 - 1469, XP001154582, ISSN: 0947-3440 *

Also Published As

Publication number Publication date
AU2003245030A1 (en) 2003-12-02
WO2003097668A2 (fr) 2003-11-27
EP1506219A2 (fr) 2005-02-16

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