WO2008050161A3 - Peptides for activation of angiogenesis, pharmaceutical compounds containing same and use of these compounds - Google Patents
Peptides for activation of angiogenesis, pharmaceutical compounds containing same and use of these compounds Download PDFInfo
- Publication number
- WO2008050161A3 WO2008050161A3 PCT/HU2007/000095 HU2007000095W WO2008050161A3 WO 2008050161 A3 WO2008050161 A3 WO 2008050161A3 HU 2007000095 W HU2007000095 W HU 2007000095W WO 2008050161 A3 WO2008050161 A3 WO 2008050161A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ser
- gly
- ile
- glu
- asp
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract 3
- 230000026341 positive regulation of angiogenesis Effects 0.000 title 1
- 210000001519 tissue Anatomy 0.000 abstract 3
- 230000033115 angiogenesis Effects 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- -1 2-aminophenyl- Chemical group 0.000 abstract 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 abstract 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical group C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 abstract 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 abstract 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 abstract 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 abstract 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 abstract 1
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 abstract 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 1
- ROHDXJUFQVRDAV-UWVGGRQHSA-N Phe-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 ROHDXJUFQVRDAV-UWVGGRQHSA-N 0.000 abstract 1
- MYVYPSWUSKCCHG-JQWIXIFHSA-N Trp-Ser Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CO)C(O)=O)=CNC2=C1 MYVYPSWUSKCCHG-JQWIXIFHSA-N 0.000 abstract 1
- 206010052428 Wound Diseases 0.000 abstract 1
- 208000027418 Wounds and injury Diseases 0.000 abstract 1
- 150000001408 amides Chemical group 0.000 abstract 1
- 230000001684 chronic effect Effects 0.000 abstract 1
- 210000005003 heart tissue Anatomy 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 208000028867 ischemia Diseases 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 abstract 1
- 208000010125 myocardial infarction Diseases 0.000 abstract 1
- 230000001537 neural effect Effects 0.000 abstract 1
- 108010051242 phenylalanylserine Proteins 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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
- C07K14/52—Cytokines; Lymphokines; Interferons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- 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
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- 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
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- 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
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- 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
-
- 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
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- 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
-
- 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
- C07K5/1027—Tetrapeptides containing heteroatoms different from O, S, or N
-
- 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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
The invention provides novel peptides of formula (I) and their salts or metal complexes R0- R1- Q(X) - R2- R3 (I) - wherein the main substituent meanings are as follows: Q represents Lys, Cys or Ser; X is H, Bzl, R0, R0-Tyr-Pro-Asp-Glu-Ile-Glu-Tyr-Ile-Phe, R0- Ile-Lys-Pro-His- Gln-Gly-Gln, or R0- Gly-Val-Ser-Ser-Ser-Ser, R0 stands for H or NH2-protecting groups commonly used in peptide chemistry, R1 is Trp, D-Trp, Phe, D-Phe, ß-Asp(a-Dopa), ß-Asp(a-Ind), Tyr-Pro-Asp- Glu-Ile-Glu-Tyr-Ile-Phe, Ile-Lys-Pro-His-Gln-Gly-Gln, Pro-Glu-Ser-Thr- Asn-Leu, Gly-Val-Ser-Ser-Ser-Ser, or a valency bond, R2 represents Gly, Asn-Asp-Glu-Gly-Leu-Glu-(Gly) n, Asp-Asp-Gly-Gln-Ile-(Gly) n, His, Ser, Cpa, Dopa, Tyr, Thr, Pro, Trp-Ser, Phe-Ser, 2-aminophenyl-, or Cys(X2), wherein X2 is Acm, Bzl or an SH-protecting group commonly used in peptide chemistry, and R3 is OH, OMe, NH2, or amide substituted by one or two identical or different C1-C6 alkyl group(s), Thr-NH2, or Tyr-OMe. The invention further provides pharmaceutical compositions containing these peptides with the ability of stimulating angiogenesis and vascularization. The invention further relates to the use of these compounds for preparing pharmaceutical compositions for treatment of injured tissues such as chronic wounds, heart tissues injured by ischemia or heart attack, and neural tissues injured by stroke. The invention also relates to a method for preparing tissue samples for testing angiogenesis-inhibiting agents.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0600814A HUP0600814A3 (en) | 2006-10-27 | 2006-10-27 | Peptides for activation of angiogenesis, pharmaceutical compounds containing same and use of these compounds |
| HUP0600814 | 2006-10-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2008050161A2 WO2008050161A2 (en) | 2008-05-02 |
| WO2008050161A3 true WO2008050161A3 (en) | 2008-10-02 |
Family
ID=89987111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/HU2007/000095 WO2008050161A2 (en) | 2006-10-27 | 2007-10-19 | Peptides for activation of angiogenesis, pharmaceutical compounds containing same and use of these compounds |
Country Status (2)
| Country | Link |
|---|---|
| HU (1) | HUP0600814A3 (en) |
| WO (1) | WO2008050161A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201018125D0 (en) * | 2010-10-26 | 2010-12-08 | Marealis As | Peptide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06172383A (en) * | 1992-04-07 | 1994-06-21 | Ichikawa Gosei Kagaku Kk | Production of peptide-substituted porphyrin |
| WO2003020215A2 (en) * | 2001-08-29 | 2003-03-13 | Regenerx Biopharmaceuticals, Inc. | Methods of treating mycocardial event related coditions with thymosin beta 4 |
| US20040225108A1 (en) * | 2002-05-22 | 2004-11-11 | Wockhardt Limited | Novel process for production of the somatostatin analog, octreotide |
-
2006
- 2006-10-27 HU HU0600814A patent/HUP0600814A3/en unknown
-
2007
- 2007-10-19 WO PCT/HU2007/000095 patent/WO2008050161A2/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06172383A (en) * | 1992-04-07 | 1994-06-21 | Ichikawa Gosei Kagaku Kk | Production of peptide-substituted porphyrin |
| WO2003020215A2 (en) * | 2001-08-29 | 2003-03-13 | Regenerx Biopharmaceuticals, Inc. | Methods of treating mycocardial event related coditions with thymosin beta 4 |
| US20040225108A1 (en) * | 2002-05-22 | 2004-11-11 | Wockhardt Limited | Novel process for production of the somatostatin analog, octreotide |
Non-Patent Citations (4)
| Title |
|---|
| GUGGI A ET AL: "Studies on trypsin inhibitors. Part IV, Synthesis of the protected undecapeptide (sequence 25-35) of porcine pancreatic secretory trypsin inhibitor II (Kazal).", INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH 1976, vol. 8, no. 2, 1976, pages 97 - 105, XP008094326, ISSN: 0367-8377 * |
| HORVATH ET AL: "Effect of new synthetic peptides and peptidomimetics on angiogenesis", PEPTIDE SCIENCE, 5 November 2006 (2006-11-05), pages 249 - 250, XP008092022 * |
| ROMOVACEK H ET AL: "Studies on polypeptides. LIII. Synthesis of a cysteine protected nonatricontapeptide corresponding to positions 66-104 of the peptide chain of ribonuclease T1.", INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH 1974, vol. 6, no. 6, 1974, pages 435 - 445, XP008094325, ISSN: 0367-8377 * |
| WILLIAMS, B. J.; YOUNG, G. T.: "Some observations concerning S-acetamidomethylcysteine and related compounds", PEPT., STRUCT. BIOL. FUNCT., PROC. AM. PEPT. SYMP., 6TH, 1979, pages 321 - 324, XP008094329 * |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0600814A3 (en) | 2009-08-28 |
| HU0600814D0 (en) | 2006-12-28 |
| WO2008050161A2 (en) | 2008-05-02 |
| HUP0600814A2 (en) | 2008-07-28 |
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