GB1396801A - Process for the manufacture of peptides - Google Patents

Process for the manufacture of peptides

Info

Publication number
GB1396801A
GB1396801A GB3098472A GB3098472A GB1396801A GB 1396801 A GB1396801 A GB 1396801A GB 3098472 A GB3098472 A GB 3098472A GB 3098472 A GB3098472 A GB 3098472A GB 1396801 A GB1396801 A GB 1396801A
Authority
GB
United Kingdom
Prior art keywords
peptides
protected
group
hydroxy
optionally substituted
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
GB3098472A
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
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 DE19712132767 external-priority patent/DE2132767A1/en
Priority claimed from DE2202613A external-priority patent/DE2202613C3/en
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of GB1396801A publication Critical patent/GB1396801A/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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
    • C07K1/124—Hydrazinolysis
    • 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
    • C07K14/62—Insulins
    • C07K14/625—Extraction from natural sources
    • 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
    • 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)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1396801 Peptides HOECHST AG 3 July 1972 [1 July 1971 20 Jan 1972] 30984/72 Heading C2C [Also in Division C3] Peptides are prepared by reacting protected amino acids or protected peptides of the formula in which Z is an amino protective group or pyroglutamyl, Y is C 1-6 alkyl optionally substituted by one or more substituents selected from OH, NH 2 , SH, esterified carboxy, carbamoyl guanidino, aryl, imidazolyl and indolyl, which may be suitably protected, where required, and the group -NH-CH-Y- may also be pyrrolidinyl, R is di-, tri-, tetra- or penta-chlorophenyl, nitrophenyl or chloronitrophenyl and m 1 is 0 to 10, with amino acids or peptides which may be protected and correspond to the formula in which Y and -NH-CHY are as defined above, m 2 is 0 to 500 and Q is OH, alkoxy or arylalkoxy, or an amino group optionally substituted by alkyl, aralkyl or aryl groups, or Q is a polymer support linked in ester or amide form, in the presence of compounds of the formula in which X is the group C=O, C=S or -N= and X and N are members of a 5- or 6-membered optionally substituted heterocyclic ring which may be fused to a benzene ring and/or which contains 1 or 2 further hetero atoms, and the pK-value of which when measured at 30‹ C. in a 0À5 molar solution in a mixture of 6 parts by volume of the dimethyl methyl ether of diethyleneglycol and 4 parts by volume of water is within the range 3À7 to 4À2, and, if necessary or desired, splitting off the protective groups. 1 - Hydroxy - 4,6 - dimethyl - 3,5 - dichloro - 2- pyridone is prepared by chlorinating 1-hydroxy- 4,6-dimethyl-2-pyridone. 3 - Hydroxy - 4 - methyl - 2,3 - dihydrothiazole- 2-thione is made by cyclizing 5-thioxo-6-oxa-4- thia-2-octanone oxime, obtained by reacting hydroxylamine hydrochloride with 5-thioxo-6- oxa-4-thia-2-octanone, which is prepared by reacting chloroacetone with C 2 H 5 OCSSK. Reference has been directed by the Comptroller to Specification 1,308,161.
GB3098472A 1971-07-01 1972-07-03 Process for the manufacture of peptides Expired GB1396801A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19712132767 DE2132767A1 (en) 1971-07-01 1971-07-01 Peptide prodn - in the presence of 1-hydroxybenzotriazole
DE2202613A DE2202613C3 (en) 1972-01-20 1972-01-20 Process for the production of peptides

Publications (1)

Publication Number Publication Date
GB1396801A true GB1396801A (en) 1975-06-04

Family

ID=25761356

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3098472A Expired GB1396801A (en) 1971-07-01 1972-07-03 Process for the manufacture of peptides

Country Status (12)

Country Link
JP (1) JPS5110201B1 (en)
AT (1) AT340067B (en)
BE (1) BE785790A (en)
CA (1) CA988079A (en)
DD (1) DD99570A5 (en)
DK (1) DK145715C (en)
FR (1) FR2144416A5 (en)
GB (1) GB1396801A (en)
HU (1) HU169326B (en)
IL (1) IL39788A (en)
NL (1) NL176255C (en)
SU (1) SU511852A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1688431A2 (en) * 1994-01-28 2006-08-09 SciClone Pharmaceuticals, Inc. Analogs of thymosin alpha 1

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102571783B1 (en) * 2022-12-16 2023-08-29 스트라토 주식회사 Search processing system performing high-volume search processing and control method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1688431A2 (en) * 1994-01-28 2006-08-09 SciClone Pharmaceuticals, Inc. Analogs of thymosin alpha 1
EP1688431A3 (en) * 1994-01-28 2006-11-29 SciClone Pharmaceuticals, Inc. Analogs of thymosin alpha 1

Also Published As

Publication number Publication date
BE785790A (en) 1973-01-03
ATA565672A (en) 1977-03-15
HU169326B (en) 1976-11-27
FR2144416A5 (en) 1973-02-09
NL176255B (en) 1984-10-16
DK145715C (en) 1983-08-08
DD99570A5 (en) 1973-08-12
IL39788A (en) 1976-07-30
SU511852A3 (en) 1976-04-25
IL39788A0 (en) 1972-08-30
CA988079A (en) 1976-04-27
JPS5110201B1 (en) 1976-04-02
NL176255C (en) 1985-03-18
NL7208757A (en) 1973-01-03
AT340067B (en) 1977-11-25
DK145715B (en) 1983-02-07

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Legal Events

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