WO2009071957A3 - Novel peptides and amino acid derivatives, pharmaceutical compositions containing same and the use of these compounds - Google Patents

Novel peptides and amino acid derivatives, pharmaceutical compositions containing same and the use of these compounds Download PDF

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Publication number
WO2009071957A3
WO2009071957A3 PCT/HU2008/000133 HU2008000133W WO2009071957A3 WO 2009071957 A3 WO2009071957 A3 WO 2009071957A3 HU 2008000133 W HU2008000133 W HU 2008000133W WO 2009071957 A3 WO2009071957 A3 WO 2009071957A3
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WO
WIPO (PCT)
Prior art keywords
stands
amino acid
neurogenic
compounds
stand
Prior art date
Application number
PCT/HU2008/000133
Other languages
French (fr)
Other versions
WO2009071957A2 (en
Inventor
Anikó HORVÁTH
György Kéri
János SEPRÖDI
Tibor VÁNTUS
Gyuláné TANAI
János SZOLCSÁNYI
Erika Pintér
Zsuzsanna Helyes
Yoshio Okada
Yuko Tsuda
Anna Miyazaki
Tamás Szüts
Original Assignee
Biostatin Gyógyszerkutató-Fejlesztö Kft.
Magyar Tudományos Akadémiai Támogatott Kutatóhelyek Irodája
Pécsi Tudományegyetem Általános Orvostudományi Kar, Farmakológiai És Fafmakoterápiai Intézet
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
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Application filed by Biostatin Gyógyszerkutató-Fejlesztö Kft., Magyar Tudományos Akadémiai Támogatott Kutatóhelyek Irodája, Pécsi Tudományegyetem Általános Orvostudományi Kar, Farmakológiai És Fafmakoterápiai Intézet filed Critical Biostatin Gyógyszerkutató-Fejlesztö Kft.
Publication of WO2009071957A2 publication Critical patent/WO2009071957A2/en
Publication of WO2009071957A3 publication Critical patent/WO2009071957A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/50—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
    • 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
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biochemistry (AREA)
  • Pain & Pain Management (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The invention relates to novel compounds of general formula (I) with neurogenic or non-neurogenic anti-inflammatory, analgetic as well as tumour inhibiting effects as well as the salts and metal complexes of these compounds. In the above formula the most important meanings of the substituents are as follows: n stands for 0 or 1, and if n is 1, then Q1, Q2 and Q3 each stand for 0; R1 and R2 stand, independently from each other, for an amino acid; if n is 0, then Q1 and Q2 stand for an amino acid residue; Q3 stands for a valency bond or an amino acid residue; R1 stands for H or C1-3 acyl, benzyloxycarbonyl, tert-butyloxycarbonyl or 9-fluorenyl-methyloxycarbonyl; R2 stands for OH, -NH-R3 or -O-R4, wherein R3 stands for H, C1-6 alkyl, C6-10 cycloalkyl or C6-10 aryl; and R4 stands for C1-6 alkyl, benzyl or 9-fluorenylmethyl. Furthermore, the invention relates to a pharmaceutical composition for treating neurogenic or non-neurogenic inflammations, pains and tumour growth and to the use of the compounds of formula (I) and the salts and metal complexes thereof for preparing pharmaceuticals compositions and to a method for treating neurogenic and non-neurogenic inflammations, pains and tumour growth.
PCT/HU2008/000133 2007-12-05 2008-11-18 Novel peptides and amino acid derivatives, pharmaceutical compositions containing same and the use of these compounds WO2009071957A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HUP0700782 2007-12-05
HU0700782A HUP0700782A3 (en) 2007-12-05 2007-12-05 Novel peptides and amino acid derivatives, pharmaceutical compositions containing the same and use of the compounds

Publications (2)

Publication Number Publication Date
WO2009071957A2 WO2009071957A2 (en) 2009-06-11
WO2009071957A3 true WO2009071957A3 (en) 2009-08-27

Family

ID=89987915

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2008/000133 WO2009071957A2 (en) 2007-12-05 2008-11-18 Novel peptides and amino acid derivatives, pharmaceutical compositions containing same and the use of these compounds

Country Status (2)

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HU (1) HUP0700782A3 (en)
WO (1) WO2009071957A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102241678B (en) * 2011-04-26 2014-10-29 辽宁利锋科技开发有限公司 Antitumor effect and application of alicyclic structure-containing compound
CN104230935A (en) * 2011-04-26 2014-12-24 辽宁利锋科技开发有限公司 Anti-tumor effect and application of compound containing alicyclic structure
WO2017212390A1 (en) * 2016-06-06 2017-12-14 Emcure Pharmaceuticals Ltd, Process for lanreotide acetate preparation

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992019254A1 (en) * 1991-04-24 1992-11-12 Warner-Lambert Company α-SUBSTITUTED POLYPEPTIDES HAVING THERAPEUTIC ACTIVITY
GB2282807A (en) * 1993-10-15 1995-04-19 Merck & Co Inc Tryptophan esters and amides as tachykinin receptor antagonists
DE4425857A1 (en) * 1994-07-07 1996-01-11 Schering Ag Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them
WO1998036743A1 (en) * 1997-02-21 1998-08-27 Cypros Pharmaceutical Corporation Neuroprotective poly-guanidino compounds which block presynaptic n and p/q calcium channels
WO2001007469A2 (en) * 1999-07-23 2001-02-01 Les Laboratoires Servier Polypeptide dendrimers as unimolecular carriers of diagnostic imaging contrast agents, bioactive substances and drugs
US6310078B1 (en) * 1998-04-20 2001-10-30 Ortho-Mcneil Pharmaceutical, Inc. Substituted amino acids as erythropoietin mimetics
WO2007045010A1 (en) * 2005-10-21 2007-04-26 Starpharma Pty Limited Inhibitory compounds

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992019254A1 (en) * 1991-04-24 1992-11-12 Warner-Lambert Company α-SUBSTITUTED POLYPEPTIDES HAVING THERAPEUTIC ACTIVITY
GB2282807A (en) * 1993-10-15 1995-04-19 Merck & Co Inc Tryptophan esters and amides as tachykinin receptor antagonists
DE4425857A1 (en) * 1994-07-07 1996-01-11 Schering Ag Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them
WO1998036743A1 (en) * 1997-02-21 1998-08-27 Cypros Pharmaceutical Corporation Neuroprotective poly-guanidino compounds which block presynaptic n and p/q calcium channels
US6310078B1 (en) * 1998-04-20 2001-10-30 Ortho-Mcneil Pharmaceutical, Inc. Substituted amino acids as erythropoietin mimetics
WO2001007469A2 (en) * 1999-07-23 2001-02-01 Les Laboratoires Servier Polypeptide dendrimers as unimolecular carriers of diagnostic imaging contrast agents, bioactive substances and drugs
WO2007045010A1 (en) * 2005-10-21 2007-04-26 Starpharma Pty Limited Inhibitory compounds

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
A.SHANZER ET AL: "Study of Cu(II) Binding to Chiral Tripodal Ligands by Electron Spin Echo Spectroscopy", JACS, no. 113, 1991, pages 1941 - 1948, XP002526914 *
B. PRADINES: "In Vitro Activities of Novel Catecholate Siderophores against Plasmodium Falciparum", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 40, no. 9, 1996, pages 2094 - 2098, XP002526975 *
F. WERNER: "complexation of Anions Including Nucleotide Anions by Ope-Chain Host Compounds with Amide, Urea and Aryl Functions", HELVETICA CHIMICA ACTA, vol. 83, 2000, pages 465 - 478, XP002526916 *
K. ICHIKAWA ET AL: "Phosphoesterhydrolysis using structural phosphatase models of tren based zinc(II) complexes and X-ray crystal structures", INORGANICA CHIMICA ACTA, no. 313, 2001, pages 125 - 136, XP002526915 *
MENZ TERRI L ET AL: "SYNTHESIS AND CHARACTERIZATION OF HYPERBRANCHED POLYLYSINE", POLYMER PREPRINTS, AMERICAN CHEMICAL SOCIETY, US, vol. 44, no. 2, 1 January 2003 (2003-01-01), pages 842 - 843, XP008074519, ISSN: 0032-3934 *

Also Published As

Publication number Publication date
HUP0700782A2 (en) 2009-07-28
HUP0700782A3 (en) 2009-11-30
HU0700782D0 (en) 2008-02-28
WO2009071957A2 (en) 2009-06-11

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