FR2401134A1 - PROCESS FOR THE PREPARATION OF THYMOSIN A1 AND AN ANALOGUE - Google Patents

PROCESS FOR THE PREPARATION OF THYMOSIN A1 AND AN ANALOGUE

Info

Publication number
FR2401134A1
FR2401134A1 FR7811686A FR7811686A FR2401134A1 FR 2401134 A1 FR2401134 A1 FR 2401134A1 FR 7811686 A FR7811686 A FR 7811686A FR 7811686 A FR7811686 A FR 7811686A FR 2401134 A1 FR2401134 A1 FR 2401134A1
Authority
FR
France
Prior art keywords
glu
asn
thr
lys
val
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.)
Granted
Application number
FR7811686A
Other languages
French (fr)
Other versions
FR2401134B1 (en
Inventor
Su-Sun Wang
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 US05/871,563 external-priority patent/US4116951A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of FR2401134A1 publication Critical patent/FR2401134A1/en
Application granted granted Critical
Publication of FR2401134B1 publication Critical patent/FR2401134B1/fr
Granted 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
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • C07K14/57581—Thymosin; Related peptides
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

L'invention concerne la synthèse de la thymosine alpha 1 . Il s'agit d'un procédé pour la préparation de thymosine alpha 1 ou de son analogue (Asn**2) et de leurs sels pharmaceutiquement acceptables, selon lequel on élimine les groupes protecteurs d'un octacosapeptide protégé de la séquence : H3 C - CO - Ser(R**1) - X - Ala - Ala- Val - Asp(OR**2) -Thr(R**3) - Ser(R**1) - Ser(R**1) - Glu(OR**4) - Ile - Thr(R** 3) - Thr(R**3) - Lys(R**5) - As- p(OR**2) - Leu - Lys(R** 5) - Glu(OR**4) - Lys(R**5) - Glu(OR**4)- Val - Val - Glu(OR** 4) - Glu(OR**4) - Ala - Glu(OR**4) - Asn - OR**6 où X est Asn ou Asp(OR**2); et R1 , R2 , R3 , R 4 , R5 et R6 sont des groupes protecteurs. Le peptide obtenu est un immuno-stimulateur.The invention relates to the synthesis of thymosin alpha 1. This is a process for the preparation of thymosin alpha 1 or its analogue (Asn ** 2) and their pharmaceutically acceptable salts, according to which the protective groups of a protected octacosapeptide of the sequence: H3 C are removed - CO - Ser (R ** 1) - X - Ala - Ala- Val - Asp (OR ** 2) -Thr (R ** 3) - Ser (R ** 1) - Ser (R ** 1) - Glu (OR ** 4) - Ile - Thr (R ** 3) - Thr (R ** 3) - Lys (R ** 5) - As- p (OR ** 2) - Leu - Lys (R ** 5) - Glu (OR ** 4) - Lys (R ** 5) - Glu (OR ** 4) - Val - Val - Glu (OR ** 4) - Glu (OR ** 4) - Ala - Glu (OR ** 4) - Asn - OR ** 6 where X is Asn or Asp (OR ** 2); and R1, R2, R3, R 4, R5 and R6 are protecting groups. The peptide obtained is an immunostimulator.

FR7811686A 1977-04-22 1978-04-20 PROCESS FOR THE PREPARATION OF THYMOSIN A1 AND AN ANALOGUE Granted FR2401134A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US78989877A 1977-04-22 1977-04-22
US05/871,563 US4116951A (en) 1977-04-22 1978-01-23 [Asn2 ]-thymosin α1 and analogs thereof

Publications (2)

Publication Number Publication Date
FR2401134A1 true FR2401134A1 (en) 1979-03-23
FR2401134B1 FR2401134B1 (en) 1983-09-30

Family

ID=27120967

Family Applications (2)

Application Number Title Priority Date Filing Date
FR7811686A Granted FR2401134A1 (en) 1977-04-22 1978-04-20 PROCESS FOR THE PREPARATION OF THYMOSIN A1 AND AN ANALOGUE
FR7835404A Granted FR2405926A1 (en) 1977-04-22 1978-12-15 (ASN2) -THYMOSIN A1 AND METHOD OF PREPARATION

Family Applications After (1)

Application Number Title Priority Date Filing Date
FR7835404A Granted FR2405926A1 (en) 1977-04-22 1978-12-15 (ASN2) -THYMOSIN A1 AND METHOD OF PREPARATION

Country Status (18)

Country Link
JP (1) JPS53137914A (en)
AT (1) AT364470B (en)
CA (1) CA1113088A (en)
CH (3) CH641152A5 (en)
DE (1) DE2817082A1 (en)
DK (1) DK147918C (en)
ES (1) ES469016A1 (en)
FI (1) FI781241A (en)
FR (2) FR2401134A1 (en)
GB (1) GB1590668A (en)
GR (1) GR71886B (en)
HU (1) HU180783B (en)
IT (1) IT1113134B (en)
LU (1) LU79488A1 (en)
NL (1) NL7804364A (en)
NO (2) NO781404L (en)
PT (1) PT67937B (en)
SE (1) SE447262B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4116951A (en) * 1977-04-22 1978-09-26 Hoffmann-La Roche Inc. [Asn2 ]-thymosin α1 and analogs thereof
DE2919592A1 (en) * 1979-05-15 1981-01-15 Max Planck Gesellschaft METHOD FOR PRODUCING THYMOSINE ALPHA 1 AND DERIVATIVES THEREOF
EP0033384B1 (en) * 1980-01-18 1984-02-15 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Medicaments containing fragments of thymosin-alpha-1 with immunostimulating activity, and thymosin-alpha-1 fragments
US4339427A (en) * 1980-04-14 1982-07-13 Hoffmann-La Roche Inc. Radioimmunoassay of thymosinα
EP0056594B1 (en) * 1981-01-14 1984-09-12 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Thymosin-alpha-1 fragments and pharmaceutical compositions with immunoregulating action containing them
CN1058500C (en) * 1993-02-03 2000-11-15 施塞克龙药品公司 Thymosin alpha-1 derivatives
US6262230B1 (en) * 1994-01-28 2001-07-17 Sciclone Pharmaceuticals Inc. Analogs of thymosin α1

Also Published As

Publication number Publication date
ATA286178A (en) 1981-03-15
IT7822629A0 (en) 1978-04-21
PT67937B (en) 1980-04-07
JPS53137914A (en) 1978-12-01
CA1113088A (en) 1981-11-24
CH641153A5 (en) 1984-02-15
SE447262B (en) 1986-11-03
DK147918B (en) 1985-01-07
FR2401134B1 (en) 1983-09-30
NO821608L (en) 1978-10-24
GR71886B (en) 1983-08-04
NO148924B (en) 1983-10-03
GB1590668A (en) 1981-06-03
DE2817082A1 (en) 1978-11-02
NO148924C (en) 1984-01-11
SE7804612L (en) 1978-12-20
DK147918C (en) 1985-08-19
LU79488A1 (en) 1979-05-25
NL7804364A (en) 1978-10-24
FI781241A (en) 1978-10-23
FR2405926A1 (en) 1979-05-11
NO781404L (en) 1978-10-24
IT1113134B (en) 1986-01-20
PT67937A (en) 1978-05-01
AT364470B (en) 1981-10-27
HU180783B (en) 1983-04-29
ES469016A1 (en) 1980-01-01
DK169478A (en) 1978-10-23
FR2405926B1 (en) 1983-09-09
CH640218A5 (en) 1983-12-30
CH641152A5 (en) 1984-02-15

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