[go: up one dir, main page]

WO2003097668A3 - Novel process for production of the somatostatin analog, octreotide - Google Patents

Novel process for production of the somatostatin analog, octreotide Download PDF

Info

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
French (fr)
Other versions
WO2003097668A2 (en
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/en
Publication of WO2003097668A2 publication Critical patent/WO2003097668A2/en
Publication of WO2003097668A3 publication Critical patent/WO2003097668A3/en
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

The present invention relates to a process for commercial production of octreotide using solution peptide chemistry and inexpensive amino acid derivatives. Thus the hexapeptide (Boc) D-Phe-Cys(Acm)-Phe-D-Trp-Lys(Boc)-Thr-OMe is synthesised by condensation of two tripeptide fragments, saponified and condensed with Cys(Acm)-Thr-OL to give the linear octapeptide alcohol. The linear peptide alcohol is treated with iodine, after removal of Boc groups, to give the cyclic peptide octreotide. The linear octapeptide alcohol can alternately be made by condensation of the protected hexapeptide acid with the dipeptide Cys(Acm)-Thr-OMe, followed by reduction with sodium borohydride.
PCT/IN2003/000160 2002-05-22 2003-04-16 Novel process for production of the somatostatin analog, octreotide Ceased WO2003097668A2 (en)

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 (en) 2002-05-22 2003-04-16 Novel process for production of the somatostatin analog, octreotide

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 (en) 2003-11-27
WO2003097668A3 true WO2003097668A3 (en) 2004-03-25

Family

ID=29551480

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000160 Ceased WO2003097668A2 (en) 2002-05-22 2003-04-16 Novel process for production of the somatostatin analog, octreotide

Country Status (3)

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

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2458084A1 (en) * 2004-03-12 2005-09-12 Dalton Chemical Laboratories Inc. Novel process for octreotide synthesis
WO2010089757A2 (en) 2008-11-07 2010-08-12 Usv Limited An improved process for synthesis of cyclic octapeptide
RU2435780C1 (en) * 2010-07-08 2011-12-10 Закрытое Акционерное Общество "Фарм-Синтез" Method for producing cyclic peptide-octreotide
WO2013132505A1 (en) 2012-03-09 2013-09-12 Natco Pharma Limited Improved process for preparation of octreotide by solution phase peptide synthesis

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
EP1506219A2 (en) 2005-02-16
WO2003097668A2 (en) 2003-11-27
AU2003245030A1 (en) 2003-12-02

Similar Documents

Publication Publication Date Title
Kato et al. Successive cleavage of N-terminal Arg1-Pro2 and Lys3-Pro4 from substance P but no release of Arg1-Pro2 from bradykinin, by X-Pro dipeptidyl-aminopeptidase
CA2052375C (en) Parathyroid hormone derivatives
WO2007146269A3 (en) Peptide fragments for inducing synthesis of extracellular matrix proteins
CN107960079A (en) A kind of synthetic method of low racemization impurity Liraglutide
Bodanszky et al. Synthesis of the vasoactive intestinal peptide (VIP)
JPH11130798A5 (en)
CN1363559A (en) Insulinotropic hormone secretion peptide derivative
JP3318622B2 (en) Prolyl endopeptidase inhibitor
WO2001078503A3 (en) Synthetic genes for plant gums and other hydroxyproline-rich glycoproteins
US8377891B2 (en) Process for synthesis of cyclic octapeptide
CN104788546A (en) Preparation method of linear peptides containing 24 amino acid residues
CN109096388A (en) A kind of preparation method of Teriparatide
WO1999005270A3 (en) Crustacean antimicrobial peptides, called penaiedines
WO2003097668A3 (en) Novel process for production of the somatostatin analog, octreotide
CN102816213A (en) Method for preparing pramlintide by using solid-phase and liquid-phase combined technology
CN1623600A (en) A kind of angiotensin I converting enzyme activity inhibitor and application thereof
CN1202131C (en) Technology of one kettle method for liquid phase synthesizing thymopentapeptide
Jorgensen et al. Angiotensin II analogs. 6. Stereochemical factors in the 5 position influencing pressor activity. 1
Birr et al. Synthesis of a new neuropeptide, the head activator from hydra
ES2340885T3 (en) SELECTIVE ENZYMATIC HYDROLYSIS OF TERC-BUTILIC ESTERS C PEPTIDES TERMINAL.
JPH0952900A (en) Novel peptide derivative usable as zinc endopeptidase 24-15 inhibitor
Ooi et al. Structural studies of ribonuclease. XII. Enzymic hydrolysis of active tryptic modifications of ribonuclease
JP4490547B2 (en) Novel peptide, its production method and use
CA2282734A1 (en) Aminopeptidase derived from bacillus licheniformis and process for preparation of natural type proteins
Rapaka et al. Racemization in the synthesis of polytripeptide models of collagen

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2003738490

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2003738490

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP

WWW Wipo information: withdrawn in national office

Ref document number: 2003738490

Country of ref document: EP