GB1153734A - Improvements in or relating to the Preparation of Octadecapeptide - Google Patents

Improvements in or relating to the Preparation of Octadecapeptide

Info

Publication number
GB1153734A
GB1153734A GB45938/66A GB4593866A GB1153734A GB 1153734 A GB1153734 A GB 1153734A GB 45938/66 A GB45938/66 A GB 45938/66A GB 4593866 A GB4593866 A GB 4593866A GB 1153734 A GB1153734 A GB 1153734A
Authority
GB
United Kingdom
Prior art keywords
boc
arg
lys
gly
cbo
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
GB45938/66A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co Ltd
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
Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1153734A publication Critical patent/GB1153734A/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]
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Zoology (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Toxicology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

1,153,734. Octadecapeptides. SHIONOGI & CO. Ltd. 14 Oct., 1966 [16 Oct., 1965 (2)], No. 45938/66. Heading C2C. H - Ser - Tyr - Met - Glu(OH) - His - Phe - Arg- Try - Gly - Lys - Pro - Val - Gly - Lys - Lys- Arg - ArgOH. (α<SP>1-18</SP>-ACTH) is prepared by condensing BOC - Ser - Tyr - Ser - Met - Glu - (OtBu) - His - Phe - Arg - Try - Gly(OH) with H - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys- (BOC) - Arg - ArgOH and removing all the protecting groups in an acid medium in one or more stages. α<SP>1-18</SP>-ACTH-amide is prepared by condensing BOC - Ser - Tyr - Ser - MetN3 with H-Glu(OtBu) - His - Phe - Arg - Try - GlyOH and the resultant decapeptide with the octapeptide-amide, in turn prepared from CBOArg(NO 2 ).Arg(NO 2 )-NH 2 - The following starting materials and intermediates are prepared: BOC-Ser OH, and the dicyclohexylamine salt; BOC Ser-Met-OMe and the N-free dipeptide ester; BOC-Ser-NHNH 2 ; BOC - Ser - Tyr - OMe and -NHNH 2 ; BOC Ser - Tyr - Ser - Met OMe and - NHNH 2 . BOC-Arg(NO 2 ) OH; CBO - Try - Gly OMe- H Try - Gly OMe; BOC - Arg(NO 2 ) - Try - Gly OMe and the N-free tripeptide ester, CF 3 COOH salt; BOC-Phe-Arg(NO 2 )-Try-Gly OMe and the N - free tetrapeptide ester CF 3 COOH salt; N<SP>im</SP> - CBO - HisOMe, HBr; CBO - Glu (OtBu) - His(CBO) - OMe and - NHNH 2 ; CBO - Glu (OtBu) - His - Phe - Arg(NO 2 ) - Try- Gly OMe and the free acid and the N - free peptide monoacetate salt; N<SP>α</SP>CBO - N<SP>#</SP> BOCLysOH - dicyclohexylamine salt; N<SP>α</SP>CBON<SP>#</SP>BOC - Lys OMe; H - Lys(BOC)OMe, CH 3 COOH salt, CBO - Gly - Lys (BOC) OMe; CBO - Val - Gly - Lys(BOC)OMe; CBO - Pro- Val - Gly - Lys(BOC)OMe and H - Pro - Val- Gly - Lys(BOC) OMe; CBO - Lys(BOC) Pro- Val - Gly Lys(BOC) - OMe and - NHNH 2 ; H - Arg(NO 2 )OB 2 , p - tosylate salt; BOCArg(NO 2 ) - Arg(NO 2 )OB 3 ; HArg(NO 2 ) - Arg- (NO 2 )OB 3 , CF 3 COOH salt; CBO - Lys- (BOC)O(N - succinimide); CBO - Lys(BOG)- Arg(NO 2 ) Arg(NO 2 ) - OB 3 ; H Lys(BOC)- Arg - Arg OH, di - CH 3 - COOH salt; CBOLys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys (BOC) - Arg - Arg OH. CH 3 COOH salt and the N<SP>α</SP>-free octapeptide thereof; BOC-Ser-Tyr- Ser - Met - Glu(OtBu) - His - Phe - Arg - Try- GlyOH, 2H 2 O; CBO - Arg(NO 2 ) - NH 2 ; H - Arg(NO 2 )NH 2 HBr; CBO - Arg(NO 2 )- Arg(NO 2 )NH 2 and the N - free dipeptide, HBr salt; CBO-Lys(BOC)-Arg(NO 2 )-Arg(NO 2 )- NH 2 ; H-Lys(BOC)Arg-Arg-NH 2 , 3CH 3 COOH; CBO - Lys(BOC) - Pro - Val - Gly - Lys(BOC)- Lys(BOC) - Arg - ArgNH 2 3,CH 3 COOH and H Lys(BOC)-Pro-Val-Gly-Lys(BOC)-Lys(BOC)- Arg - Arg - NH 2 , 3CH 3 COOH.
GB45938/66A 1965-10-16 1966-10-14 Improvements in or relating to the Preparation of Octadecapeptide Expired GB1153734A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6367565 1965-10-16
JP6367465 1965-10-16

Publications (1)

Publication Number Publication Date
GB1153734A true GB1153734A (en) 1969-05-29

Family

ID=26404812

Family Applications (1)

Application Number Title Priority Date Filing Date
GB45938/66A Expired GB1153734A (en) 1965-10-16 1966-10-14 Improvements in or relating to the Preparation of Octadecapeptide

Country Status (3)

Country Link
CH (2) CH506486A (en)
DE (1) DE1543882A1 (en)
GB (1) GB1153734A (en)

Also Published As

Publication number Publication date
DE1543882A1 (en) 1970-02-05
CH506486A (en) 1971-04-30
CH505791A (en) 1971-04-15

Similar Documents

Publication Publication Date Title
GB1524747A (en) Polypeptide
GB1516947A (en) Hentricontapeptides
KR850003417A (en) Method of producing polypeptide
GB1527252A (en) Cyclization of peptides via cystine linkages
GB2091740A (en) C-terminal fragment of human chroionic gonadotropin
KR840007569A (en) Preparation of GRF Analog Peptides
GB1528336A (en) Compounds compositions and methods of their use
KR870007203A (en) Methods for making peptides
GB1570210A (en) Peptides
GB1464774A (en) 13-l-norleucine-14-desamido-motilin a method for preparing it and a therapeutic containing it
GB1526367A (en) Polypeptide
GB1153734A (en) Improvements in or relating to the Preparation of Octadecapeptide
GB1536677A (en) Peptide derivatives having a antihypertensive effect and process for their manufacture
GB1294771A (en) Thyrocalcitonin derivative
GB1316545A (en) 1-alpha-aminoisobutyric acid-corticotropin peptides
EP0123951A3 (en) Intermediates for thymosin alpha 1
GB1309150A (en) Acthactive peptides and process for their manufacture
GB1536878A (en) Octapeptide
GB1532181A (en) Pentapetides and a method of preparing them
GB1532169A (en) Fragments of secretin
GB1465235A (en) Process for preparing peptides
GB1298318A (en) Corticotropin peptides
GB1155925A (en) Synthesis Of Octapeptides
Liébecq Abbreviated designation of amino acid derivatives and peptides
WEITZEL et al. Structure and Activity of Insulin, XV. Further Evidence for the Importance of Arginine Residue B 22 in the Activity of Insulin. Semisyntheses of Despentapeptide-(B 26-30)-Insulins Varied in B 22 Using Desnonapeptide-(B 22-30)-Insulin and Tetrapeptides