GB1308161A - Process for the manufacture of peptides - Google Patents

Process for the manufacture of peptides

Info

Publication number
GB1308161A
GB1308161A GB1627470A GB1627470A GB1308161A GB 1308161 A GB1308161 A GB 1308161A GB 1627470 A GB1627470 A GB 1627470A GB 1627470 A GB1627470 A GB 1627470A GB 1308161 A GB1308161 A GB 1308161A
Authority
GB
United Kingdom
Prior art keywords
pro
phe
peptide
amino acid
protected amino
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.)
Expired
Application number
GB1627470A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 DE19691917690 external-priority patent/DE1917690C3/en
Priority claimed from DE19691937656 external-priority patent/DE1937656C3/en
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1308161A publication Critical patent/GB1308161A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/695—Corticotropin [ACTH]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)

Abstract

1308161 Peptide process; benzotriazoles FARBWERKE HOECHST AG 6 April 1970 [5 April 1969 24 July 1969] 16274/70 Heading C2C In a process for preparing a peptide a protected amino acid or peptide containing a free carboxylic group is reacted with a protected amino acid or peptide containing a free amino group in a conventional solvent and in the presence of a carbodiimide and 1-2 equivalents of a benzotriazole (I) where R is H, halogen, CF 3 , alkyl, nitro, carboxamide sulphonic acid amide, cyano, methoxy or ethoxy and n is 1-4 and optionally the protecting groups are removed. The invention also comprises compounds (I) where R is as defined but not H. In the process (I) is preferably reacted with a protected amino acid or peptide to form an activated ester before condensation with the free amine. Compounds (I) are prepared by condensing an o-chloronitro-benzene with hydrazine. Examples include the preparation of 1-23 ACTH, the protected decapeptide having the sequence of antamanide (Z - Phe - Phe - Pro - Pro - Phe - Phe - Val - Pro- Pro-Ala-OtBu), sequence 54-63 of pigs proinsulin (Z-Leu-Ala-Leu-Glu(OtBu)-Gly-Pro-Pro- GlN-Lys(BOC)-ArgOH) together with other smaller peptides and their intermediates and starting products.
GB1627470A 1969-04-05 1970-04-06 Process for the manufacture of peptides Expired GB1308161A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19691917690 DE1917690C3 (en) 1969-04-05 1969-04-05 Process for the production of peptides
DE19691937656 DE1937656C3 (en) 1969-07-24 1969-07-24 Process for the production of peptides

Publications (1)

Publication Number Publication Date
GB1308161A true GB1308161A (en) 1973-02-21

Family

ID=25757250

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1627470A Expired GB1308161A (en) 1969-04-05 1970-04-06 Process for the manufacture of peptides

Country Status (11)

Country Link
BE (1) BE748545A (en)
CH (1) CH551948A (en)
DK (1) DK126184B (en)
FI (1) FI53122C (en)
FR (1) FR2042968A5 (en)
GB (1) GB1308161A (en)
HU (1) HU164903B (en)
IL (1) IL34230A (en)
NL (1) NL166924C (en)
NO (1) NO129567B (en)
SE (1) SE352341B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986003494A1 (en) * 1984-12-11 1986-06-19 Lkb Biochrom Limited Method for a solid phase synthesis of a linear combination of amino acid residues
AU597031B2 (en) * 1986-02-03 1990-05-24 Novabiochem Ag Monitoring method for the synthesis of a linear combination of amino acid residues

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1226552B (en) * 1988-07-29 1991-01-24 Ellem Ind Farmaceutica IMMUNOSTIMULANT PEPTIDES.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986003494A1 (en) * 1984-12-11 1986-06-19 Lkb Biochrom Limited Method for a solid phase synthesis of a linear combination of amino acid residues
AU597031B2 (en) * 1986-02-03 1990-05-24 Novabiochem Ag Monitoring method for the synthesis of a linear combination of amino acid residues

Also Published As

Publication number Publication date
BE748545A (en) 1970-10-06
FI53122B (en) 1977-10-31
DK126184B (en) 1973-06-18
IL34230A0 (en) 1970-06-17
FI53122C (en) 1978-02-10
NL7004811A (en) 1970-10-07
FR2042968A5 (en) 1971-02-12
NL166924C (en) 1981-10-15
SU439967A3 (en) 1974-08-15
SE352341B (en) 1972-12-27
NL166924B (en) 1981-05-15
NO129567B (en) 1974-04-29
CH551948A (en) 1974-07-31
HU164903B (en) 1974-05-28
IL34230A (en) 1973-10-25

Similar Documents

Publication Publication Date Title
US3906031A (en) Novel 9-fluorenylmethoxycarbonyl compounds
Akabori et al. A new method for the protection of the sulfhydryl group during peptide synthesis
Sakakibara et al. The trifluoroacetate method of peptide synthesis. I. The synthesis and use of trifluoroacetate reagents
Patel et al. Synthesis of benzyl esters of α-amino acids
US3875207A (en) Process for the temporary protection of amino groups in peptide syntheses
GB1003683A (en) New polypeptides and process for their manufacture
GB1329860A (en) Process for the manufacture of peptides containing cystine
US3131174A (en) Ng tosyl arginine and peptide synthesis therewith
GB1308161A (en) Process for the manufacture of peptides
Wilchek et al. The synthesis of tryptophan peptides
Katchalski [81] Procedures for preparation of peptide polymers: I. Preparation of poly-l-lysine
US3711458A (en) Substituted and unsubstituted vinyloxycarbonyl groups as amino protecting groups in the syntheses of peptides
US3592836A (en) Aryloxycarbonyl fluorides and amino acids and their production
Sakakibara et al. A proposal for using mild bases in the preparation of optically pure peptides
GB1003176A (en) Butyl ethers of hydroxy amino acids and peptides and derivatives thereof
US3035041A (en) Method of preparing amides
US3872074A (en) Method for the aminolysis of activated esters in the presence of N-hydroxy compounds as catalysts
US3856848A (en) Process for preparing a protected arginine
US3839315A (en) Novel peptides having cholecystokinin activity and intermediates therefor
EP0004394B1 (en) Psychopharmacological peptides, process for their preparation and their pharmaceutical formulations
GB1002041A (en) New polypeptides and process for their manufacture
GB1329618A (en) Peptides having adrenocorticotropic activity and process for their preparation
US3433779A (en) Long-chain aliphatic esters of lysine and other basic amino acids and peptides thereof
Goodman et al. Conformational aspects of polypeptide structure XIV. Synthesis of l‐glutamate oligomers via active ester and azide coupling reactions
GB1323362A (en) Cyclopeptides derived from polymyxins and their preparation

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years