DE353565T1 - Immunostimulierende peptide, deren verfahren zur herstellung und sie enthaltende pharmazeutische zusammensetzungen. - Google Patents
Immunostimulierende peptide, deren verfahren zur herstellung und sie enthaltende pharmazeutische zusammensetzungen.Info
- Publication number
- DE353565T1 DE353565T1 DE198989113447T DE89113447T DE353565T1 DE 353565 T1 DE353565 T1 DE 353565T1 DE 198989113447 T DE198989113447 T DE 198989113447T DE 89113447 T DE89113447 T DE 89113447T DE 353565 T1 DE353565 T1 DE 353565T1
- Authority
- DE
- Germany
- Prior art keywords
- arg
- ala
- lys
- glu
- formula
- 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.)
- Pending
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract 11
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract 9
- 230000003308 immunostimulating effect Effects 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 235000001014 amino acid Nutrition 0.000 claims abstract 7
- SGYSTDWPNPKJPP-GUBZILKMSA-N Arg-Ala-Arg Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O SGYSTDWPNPKJPP-GUBZILKMSA-N 0.000 claims abstract 6
- 239000011347 resin Substances 0.000 claims abstract 6
- 229920005989 resin Polymers 0.000 claims abstract 6
- 150000001413 amino acids Chemical class 0.000 claims abstract 4
- 239000004475 Arginine Substances 0.000 claims abstract 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract 3
- 235000013922 glutamic acid Nutrition 0.000 claims abstract 3
- 239000004220 glutamic acid Substances 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000006239 protecting group Chemical group 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- -1 Boc-protected amino Chemical class 0.000 claims 1
- SJJHXJDSNQJMMW-SRVKXCTJSA-N Glu-Lys-Arg Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O SJJHXJDSNQJMMW-SRVKXCTJSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 244000309464 bull Species 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 2
- 239000003022 immunostimulating agent Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
- C07K14/66—Thymopoietins
- C07K14/662—Thymopoietins 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
- C07K5/08—Tripeptides
- C07K5/0819—Tripeptides with the first amino acid being acidic
-
- 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Immunology (AREA)
- Toxicology (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Endocrinology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Claims (7)
1. Peptide der Formel I
A - &khgr; - Lys - y - B
worin
A die Bedeutung hat von H, einem Tripeptid der Formel Arg-Ala-Arg oder
einem Hexapeptid der Formel Glu-Lys-Arg-Arg-Ala-Arg,
&khgr; und y, die voneinander verschieden sind, ein Arginin(Arg)- oder ein
Glutaminsäure-(GIu)-Rest sind; B die Bedeutung hat von OH oder einem Tripeptid Arg-Ala-Arg, mit der
Maßgabe, daß, wenn A Wasserstoff ist und &khgr; Arg ist, B unterschiedlich von OH ist, und die pharmazeutisch brauchbaren Salze davon.
2. Peptide der Formel I, worin die Aminosäuren aus der D-, L- oder DL-Reihe
sind.
3. Acetat-, Trifluoracetat-, Sulfat-, Hydrochlorid-Salze von Peptiden der
Formel
4. Peptid nach Anspruch 1 oder 2, ausgewählt aus der Gruppe von Arg-Lys-Glu-Arg-Ala-Arg,
Arg-Lys-Glu-Arg-D-Ala-Arg, Arg-Ala-Arg-Arg-Lys-Glu,
Arg-D-Ala-Arg-Arg-Lys-Glu, Arg-Ala-Arg-Arg-Lys-Glu-Arg-Ala-Arg, GIu-Lys-Arg,
Arg-Ala-Arg-Glu-Lys-Arg, Glu-Lys-Arg-Arg-Ala-Arg, Glu-Lys-Arg-Arg-Ala-Arg-Glu-Lys-Arg.
5. Pharmazeutische Zusammensetzung mit immunstimulierender Aktivität,
umfassend als aktives Prinzip ein Peptid nach den Ansprüchen 1 - 4 im Gemisch mit einem brauchbaren Träger.
6. Verwendung der Peptide nach den Ansprüchen 1-4 zur Herstellung von
Medikamenten mit immunstimulierender Aktivität zur Behandlung von primären und sekundären Immunerkrankungen.
• · t t 3 * «&phgr;
_2- 0363565
7. Verfahren zur Herstellung von Peptiden der Formel I
A-x- Lys - y - B I
worin 5 A die Bedeutung hat von H, einem Tripeptid der Formel Arg-Ala-Arg oder
einem Hexapeptid der Formel Glu-Lys-Arg-Arg-Ala-Arg,
&khgr; und y, die voneinander verschieden sind, ein Arginin(Arg)- oder ein
Glutaminsäure(GIu)-Rest sind; B die Bedeutung hat von OH oder einem Tripeptid Arg-Ala-Arg, mit der
Maßgabe, daß, wenn A Wasserstoff ist und &khgr; Arg ist, B unterschiedlich
von OH ist, umfassend folgende Stufen:
a) Binden der Boc-geschützten Carboxy-endständigen Aminosäure an ein
geeignetes Harz;
b) Reaktion der anderen Boc-geschützten Aminosäuren mit der an das
Harz gebundenen Carboxy-endständigen Aminosäure in der gewünschten
Sequenz;
c) Entfernen der Schutzgruppen und Freisetzen der so erhaltenen
Peptide von dem Harz.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8821556A IT1226552B (it) | 1988-07-29 | 1988-07-29 | Peptidi immunostimolanti. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE353565T1 true DE353565T1 (de) | 1990-06-13 |
Family
ID=11183555
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE198989113447T Pending DE353565T1 (de) | 1988-07-29 | 1989-07-21 | Immunostimulierende peptide, deren verfahren zur herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
| DE8989113447T Expired - Fee Related DE68905552T2 (de) | 1988-07-29 | 1989-07-21 | Immunostimulierende peptide, deren verfahren zur herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8989113447T Expired - Fee Related DE68905552T2 (de) | 1988-07-29 | 1989-07-21 | Immunostimulierende peptide, deren verfahren zur herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5079231A (de) |
| EP (1) | EP0353565B1 (de) |
| JP (1) | JPH0288595A (de) |
| AT (1) | ATE87315T1 (de) |
| DE (2) | DE353565T1 (de) |
| ES (1) | ES2013584A4 (de) |
| GR (1) | GR900300062T1 (de) |
| HU (1) | HU204071B (de) |
| IT (1) | IT1226552B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU9140891A (en) * | 1990-11-23 | 1992-06-25 | Immunodynamics, Inc. | Synthetic immunoactive peptides having immunomodulating and therapeutic activities |
| US5492894A (en) * | 1991-03-21 | 1996-02-20 | The Procter & Gamble Company | Compositions for treating wrinkles comprising a peptide |
| AU667578B2 (en) | 1992-08-27 | 1996-03-28 | Deakin Research Limited | Retro-, inverso-, and retro-inverso synthetic peptide analogues |
| US6080719A (en) * | 1996-02-23 | 2000-06-27 | Hoechst Aktiengesellschaft | Cyclohexapeptides and their mixtures, a process for preparing them, and their use |
| AU8912698A (en) | 1997-08-19 | 1999-03-08 | University Of Medicine And Dentistry Of New Jersey | Inhibition of hiv-1 replication using d-amino acid peptides |
| FR2806727A1 (fr) * | 2000-03-23 | 2001-09-28 | Pf Medicament | Molecule d'interet pharmaceutique comprotant en son extremite n-terminale un acide glutamique ou une glutamine sous forme de sel d'addition d'acide fort physiologiquement acceptable |
| CA2495222A1 (en) * | 2002-08-13 | 2004-02-19 | Wyeth | Peptides as solubilizing excipients for transforming growth factor ss proteins |
| US20100260680A1 (en) * | 2007-06-05 | 2010-10-14 | Oriental Yeast Co., Ltd. | Novel bone mass increasing agent |
| CN102234314B (zh) * | 2010-04-29 | 2014-07-09 | 上海医药工业研究院 | 一组蛇毒来源的活性肽的制备方法及其在抗肿瘤方面的应用 |
| KR101791526B1 (ko) * | 2016-02-18 | 2017-11-01 | (주)케어젠 | 발모 촉진 활성을 나타내는 펩타이드 및 이의 용도 |
| AU2019268411B2 (en) * | 2018-05-15 | 2024-03-14 | Interk Peptide Therapeutics Limited | Activating agents |
| AU2019268412A1 (en) | 2018-05-15 | 2020-12-03 | Interk Peptide Therapeutics Limited | Peptide activating agent |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU164903B (de) * | 1969-04-05 | 1974-05-28 | ||
| CH665645A5 (fr) * | 1981-07-09 | 1988-05-31 | Michel Flork | Derives de dipeptides et leur procede de preparation. |
| US4581168A (en) * | 1983-02-21 | 1986-04-08 | Sanofi | Synthesis of hpGRF (Somatocrinin) in liquid phase and intermediate peptides |
| DE3401545A1 (de) * | 1983-08-03 | 1985-02-14 | Hoechst Ag, 6230 Frankfurt | Neue peptide mit immunstimulierender wirkung, verfahren zu deren herstellung und deren verwendung |
| US4505853A (en) * | 1983-11-18 | 1985-03-19 | Ortho Pharmaceutical Corporation | Enzyme-resistant immunomodulatory peptides |
| FR2567524B1 (fr) * | 1984-07-10 | 1987-11-27 | Sanofi Sa | Procede de synthese de la somatocrinine en phase liquide et peptides intermediaires |
| US4654419A (en) * | 1984-08-08 | 1987-03-31 | Scripps Clinic And Research Foundation | Synthetic polypeptides and antibodies related to epstein-barr virus nuclear antigen |
| ATE108022T1 (de) * | 1985-10-24 | 1994-07-15 | Southwest Found Biomed Res | Synthetische peptide und deren verwendung zur diagnose und impfung für aids und arc. |
| IT1188645B (it) * | 1986-04-09 | 1988-01-20 | Ellem Ind Farmaceutica | Tripeptide ad attivita' immunostimolante |
| IT1222437B (it) * | 1987-08-04 | 1990-09-05 | Ellem Ind Farmaceutica | Tripeptidi utili come immunostimolanti e nella prevenzione delle metastasi e relativo procedimento di preparazione |
-
1988
- 1988-07-29 IT IT8821556A patent/IT1226552B/it active
-
1989
- 1989-07-21 EP EP89113447A patent/EP0353565B1/de not_active Expired - Lifetime
- 1989-07-21 DE DE198989113447T patent/DE353565T1/de active Pending
- 1989-07-21 ES ES89113447T patent/ES2013584A4/es active Pending
- 1989-07-21 AT AT89113447T patent/ATE87315T1/de not_active IP Right Cessation
- 1989-07-21 DE DE8989113447T patent/DE68905552T2/de not_active Expired - Fee Related
- 1989-07-24 US US07/384,327 patent/US5079231A/en not_active Expired - Fee Related
- 1989-07-28 JP JP1196470A patent/JPH0288595A/ja active Pending
- 1989-07-28 HU HU893902A patent/HU204071B/hu not_active IP Right Cessation
-
1991
- 1991-07-31 GR GR90300062T patent/GR900300062T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE68905552T2 (de) | 1993-07-15 |
| HU204071B (en) | 1991-11-28 |
| EP0353565A1 (de) | 1990-02-07 |
| EP0353565B1 (de) | 1993-03-24 |
| DE68905552D1 (de) | 1993-04-29 |
| US5079231A (en) | 1992-01-07 |
| IT8821556A0 (it) | 1988-07-29 |
| IT1226552B (it) | 1991-01-24 |
| HUT53914A (en) | 1990-12-28 |
| ATE87315T1 (de) | 1993-04-15 |
| JPH0288595A (ja) | 1990-03-28 |
| GR900300062T1 (en) | 1991-07-31 |
| ES2013584A4 (es) | 1990-05-16 |
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