GB1486580A - Heptapeptides - Google Patents
HeptapeptidesInfo
- Publication number
- GB1486580A GB1486580A GB50494/76A GB5049476A GB1486580A GB 1486580 A GB1486580 A GB 1486580A GB 50494/76 A GB50494/76 A GB 50494/76A GB 5049476 A GB5049476 A GB 5049476A GB 1486580 A GB1486580 A GB 1486580A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phe
- boc
- lys
- asn
- trt
- 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
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
- C07K14/575—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
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
-
- 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
- C07K5/1019—Tetrapeptides with the first amino acid being basic
-
- 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)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1486580 Hexa and heptapeptides AYERST MCKENNA & HARRISON Ltd 6 Dec 1974 [10 Dec 1973 1 Aug 1974] 50494/76 Divided out of 1486578 Heading C3H Peptides of formula wherein X is OH or O(lower(C 1 -C 4 )alkyl) α is Acm or Trt R 3 is hydrogen or Boc-NH- or an acylating derivative (defined) thereof, provided that, if R 3 is Boc-NH-, Lys may be replaced by D-Lys. The peptides may be prepared by a process which comprises: the reaction of the dipeptide with an activated ester of to yield the tripeptide which is treated under moderately acidic conditions (defined) to yield which is reacted with an activated ester of to yield the tetrapeptide which, on hydrogenation in the presence of a noble metal hydrogenation catalyst, yields which is reacted with an activated ester of wherein either 8 is hydrogen and 81 is Trt, or 8 and #<SP>1</SP> together represent Chb, to yield which is reacted with an activated ester of (which is obtained by the reaction of H-Gly- O(lower alkyl) with an activated ester of CH 3 CH(R<SP>3</SP>)COOH, and hydrolysis of the resultant compound) to yield which, on reaction with hydrazine hydrate, yields which is reacted with an organic nitrite (preferably t-butyl nitrite or isoamyl nitrite) yields Peptides of the invention prepared are: Boc - Ala - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-N 3 Boc - Ala - Gly - Cys(Trt) - D - Lys(Boc) - Asn- Phe-Phe-OCH3 Boc - Ala - Gly - Cys(Trt) - D - Lys(Boc) - Asn- Phe-Phe-NHNH 2 CH 3 CH 2 CO - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-OCH 3 CH 3 CH 2 CO - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-NHNH 2 CH 3 CH 2 CO - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-N 3 . Peptides intermediates isolated are: PENTAPEPTIDES: Chb - Cys(Acm) - Lys- (Boc) - Asn - Phe - Phe - OCH 3 ; Trt and H - Cys- (Trt)-Lys(Boc)-Asn-Phe-Phe-OCH 3 ; H and Trt- Cys-D-Lys(Boc)-Asn-Phe-Phe-OCH 3 . TETRAPEPTIDES: Z and H-Lys(Boc)-Asn- Phe-Phe-OCH 3 ; Z and H-D-Lys(Boc)-Asn-Phe- Phe-OCH 3 . TRIPEPTIDES: Boc and H-Asn-Phe-Phe- OCH 3 . Dipeptide intermediates isolated are: Boc-Ala-Gly-OCH 3 , OH and OTcp; Boc and N-Phe-Phe-OCH 3 .
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US423352A US3917578A (en) | 1973-12-10 | 1973-12-10 | Process for producing somatostatin and intermediates |
US493595A US3917581A (en) | 1974-08-01 | 1974-08-01 | Derivatives of somatostatin and process therefor |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1486580A true GB1486580A (en) | 1977-09-21 |
Family
ID=27025966
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB50494/76A Expired GB1486580A (en) | 1973-12-10 | 1974-12-06 | Heptapeptides |
GB50493/76A Expired GB1486579A (en) | 1973-12-10 | 1974-12-06 | Heptapeptides |
GB52779/74A Expired GB1486578A (en) | 1973-12-10 | 1974-12-06 | Process for preparing somatostatin and derivatives thereo |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB50493/76A Expired GB1486579A (en) | 1973-12-10 | 1974-12-06 | Heptapeptides |
GB52779/74A Expired GB1486578A (en) | 1973-12-10 | 1974-12-06 | Process for preparing somatostatin and derivatives thereo |
Country Status (10)
Country | Link |
---|---|
JP (1) | JPS5088064A (en) |
CA (1) | CA1034116A (en) |
CH (1) | CH605680A5 (en) |
CS (1) | CS191922B2 (en) |
DE (1) | DE2458135A1 (en) |
FR (1) | FR2253532A1 (en) |
GB (3) | GB1486580A (en) |
IL (1) | IL46065A (en) |
NL (1) | NL7415916A (en) |
SE (1) | SE7415414L (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5712417A (en) * | 1989-09-28 | 1998-01-27 | Abbott Laboratories | Inhibitors of retroviral proteases |
-
1974
- 1974-11-15 IL IL46065A patent/IL46065A/en unknown
- 1974-12-06 GB GB50494/76A patent/GB1486580A/en not_active Expired
- 1974-12-06 CH CH1627774A patent/CH605680A5/xx not_active IP Right Cessation
- 1974-12-06 NL NL7415916A patent/NL7415916A/en not_active Application Discontinuation
- 1974-12-06 GB GB50493/76A patent/GB1486579A/en not_active Expired
- 1974-12-06 GB GB52779/74A patent/GB1486578A/en not_active Expired
- 1974-12-07 JP JP49142431A patent/JPS5088064A/ja active Pending
- 1974-12-09 DE DE19742458135 patent/DE2458135A1/en not_active Withdrawn
- 1974-12-09 CA CA215,666A patent/CA1034116A/en not_active Expired
- 1974-12-09 CS CS748387A patent/CS191922B2/en unknown
- 1974-12-09 SE SE7415414A patent/SE7415414L/xx unknown
- 1974-12-10 FR FR7440486A patent/FR2253532A1/fr not_active Withdrawn
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5712417A (en) * | 1989-09-28 | 1998-01-27 | Abbott Laboratories | Inhibitors of retroviral proteases |
Also Published As
Publication number | Publication date |
---|---|
SE7415414L (en) | 1975-06-11 |
IL46065A0 (en) | 1975-02-10 |
CH605680A5 (en) | 1978-10-13 |
FR2253532A1 (en) | 1975-07-04 |
IL46065A (en) | 1978-07-31 |
GB1486579A (en) | 1977-09-21 |
DE2458135A1 (en) | 1975-06-12 |
NL7415916A (en) | 1975-06-12 |
GB1486578A (en) | 1977-09-21 |
CA1034116A (en) | 1978-07-04 |
JPS5088064A (en) | 1975-07-15 |
CS191922B2 (en) | 1979-07-31 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |