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WO1999042435A3 - Myxochelines - Google Patents

Myxochelines Download PDF

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Publication number
WO1999042435A3
WO1999042435A3 PCT/EP1999/001131 EP9901131W WO9942435A3 WO 1999042435 A3 WO1999042435 A3 WO 1999042435A3 EP 9901131 W EP9901131 W EP 9901131W WO 9942435 A3 WO9942435 A3 WO 9942435A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
cooh
coor1
substituent
compounds
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.)
Ceased
Application number
PCT/EP1999/001131
Other languages
German (de)
French (fr)
Other versions
WO1999042435A2 (en
Inventor
Horst-Dieter Ambrosi
Kai Uwe Bindseil
Gerhard Jas
Lutz Mueller-Kuhrt
Rolf Reissbrodt
Wolfram Trowitzsch-Kienast
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.)
Analyticon AG Biotechnologie Pharmazie
Original Assignee
Analyticon AG Biotechnologie Pharmazie
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
Priority claimed from DE19807475A external-priority patent/DE19807475A1/en
Application filed by Analyticon AG Biotechnologie Pharmazie filed Critical Analyticon AG Biotechnologie Pharmazie
Priority to AU32536/99A priority Critical patent/AU3253699A/en
Publication of WO1999042435A2 publication Critical patent/WO1999042435A2/en
Publication of WO1999042435A3 publication Critical patent/WO1999042435A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
    • A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/547—Chelates, e.g. Gd-DOTA or Zinc-amino acid chelates; Chelate-forming compounds, e.g. DOTA or ethylenediamine being covalently linked or complexed to the pharmacologically- or therapeutically-active agent
    • 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
    • C07C235/52—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 carboxyl groups
    • 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
    • C07C235/58—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 with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—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 with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
    • C12Q1/04—Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor
    • C12Q1/045—Culture media therefor

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Zoology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Toxicology (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Biophysics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Immunology (AREA)
  • Physics & Mathematics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to compounds of general formula (A), where R is COOH, COOR1, CH2-OH, C(=O)NR2R3, CN, CH¿2NR?2R3, C(=O)-Z, CH¿2?-Z, or a substituent in accordance with formula (C), R?4¿ is COOH, COOR1, CH2-OH, C(=O)NR2R3CN, CH¿2NR?2R3 or a substituent in accordance with formula (D), where R1 is CxH2x+1 with x = 1,2,3,4,5, -CH2-C6H5 or -C6H5, R2, R3 independently of each other are H, C¿x?H2x+1 with x = 1,2,3,4,5, -CH2-C6H5 or -C6H5, Y independently of each other are benzoyl, formyl, acetyl, trifluoroacetyl, glycosyl or silyl; Z is an organic group linked via an O, N or S, and n is 1,2,3,4 or 5, and the absolute configuration at C* can be both S and R, as well as the salts of the compounds, especially alkali, alkaline-earth or ammonium salts, where R is not CH2NH2 or CN if n = 3 or 4 and R?4¿ = formula (D) with Y = H, and R is not formula (C) with Y = H if n = 2,3,4,5 and R4 = formula (D) with Y = H, and R is not CH¿2?-OH or COOH if R?4¿ = formula (D) with Y = H and n = 4 and the absolute configuration at the level of C* is S.
PCT/EP1999/001131 1998-02-21 1999-02-22 Myxochelines Ceased WO1999042435A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU32536/99A AU3253699A (en) 1998-02-21 1999-02-22 Myxochelines

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19807360 1998-02-21
DE19807360.7 1998-02-21
DE19807475.0 1998-02-24
DE19807475A DE19807475A1 (en) 1998-02-24 1998-02-24 New myxocheline derivatives useful e.g. for treating disorders associated with deficient metal ion metabolism, especially iron or aluminium metabolism, e.g. hemosiderosis, thalassemia or Alzheimer's disease

Publications (2)

Publication Number Publication Date
WO1999042435A2 WO1999042435A2 (en) 1999-08-26
WO1999042435A3 true WO1999042435A3 (en) 1999-12-16

Family

ID=26044049

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/001131 Ceased WO1999042435A2 (en) 1998-02-21 1999-02-22 Myxochelines

Country Status (2)

Country Link
AU (1) AU3253699A (en)
WO (1) WO1999042435A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2402719C (en) * 2000-03-21 2012-03-20 Emisphere Technologies, Inc. Method of preparing alkylated salicylamides via a dicarboxylate intermediate
DE10111161A1 (en) * 2001-03-01 2002-09-05 Gruenenthal Gmbh New siderophore analogues as 4- or 6-toothed iron chelators based on amino acids or peptides, processes for their preparation and their use
DE102006033321A1 (en) * 2006-07-17 2008-01-24 Westfälische Wilhelms-Universität Münster Medical use of N-phenylpropenoyl amino acid derivatives and related compounds
CA2680366C (en) 2007-03-09 2016-06-21 University Health Network Inhibitors of carnitine palmitoyltransferase and treating cancer
US9120744B2 (en) * 2007-04-16 2015-09-01 The Regents Of The University Of Michigan Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism
CA2694724C (en) 2007-08-01 2017-09-12 University Health Network Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer
JP5374058B2 (en) * 2008-03-12 2013-12-25 株式会社 資生堂 Glutamic acid derivative, keratinization inhibitor, pore reducing agent, rough skin prevention / improving agent, and composition for external use on skin
US9718760B2 (en) 2012-10-31 2017-08-01 The Regents Of The University Of Michigan Plasminogen activator inhibitor-1 inhibitors and methods of use thereof
CN110869346B (en) 2017-07-27 2024-03-29 密歇根大学董事会 Inhibitors of plasminogen activator inhibitor-1 (PAI-1) and methods of use
US20250057802A1 (en) * 2021-07-08 2025-02-20 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Broad-spectrum antiviral drugs

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4447374A1 (en) * 1994-12-22 1996-06-27 Trowitzsch Kienast Wolfram Pro New siderophore cpds. esp. myxochelin C, used as chelating agents
WO1997049670A1 (en) * 1996-06-26 1997-12-31 Grünenthal GmbH New synthetic catechol derivatives, method for production and use thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4447374A1 (en) * 1994-12-22 1996-06-27 Trowitzsch Kienast Wolfram Pro New siderophore cpds. esp. myxochelin C, used as chelating agents
WO1997049669A1 (en) * 1994-12-22 1997-12-31 Analyticon Ag Biotechnologie Pharmazie Compounds which can form complexes with metals
DE19626020A1 (en) * 1994-12-22 1998-01-02 Trowitzsch Kienast Wolfram Pro Synthetic siderophore compounds
WO1997049670A1 (en) * 1996-06-26 1997-12-31 Grünenthal GmbH New synthetic catechol derivatives, method for production and use thereof

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
A-K. DUHME ET AL.: "Synthesis and Ironbinding properties of Protochelin, the tris(catecholamide) siderophore of Azotobacter vinelandii", CHEMISCHE BERICHTE, vol. 130, 1997, WEINHEIM DE, pages 969 - 973, XP002115171 *
AKIYAMA M ET AL: "DESIGN AND SYNTHESIS OF ARTIFICIAL SIDEROPHORES: LYSINE-BASED TRISCATECHOLATE LIGANDS AS A MODEL FOR ENTEROBACTIN", CHEMISTRY LETTERS, no. 9, 1 January 1995 (1995-01-01), pages 849/850, XP000617378, ISSN: 0366-7022 *
AMBROSI H D ET AL: "Myxochelins B, C, D, E, and F. A new structural principle for powerful siderophores imitating nature", EUR. J. ORG. CHEM. (EJOCFK,1434193X);1998; (3); PP.541-551, AnalytiCon A.-G.;Berlin; D-13355; Germany (DE), XP002115284 *
BARELMANN I ET AL: "CEPACIACHELIN, A NEW CATECHOLATE SIDEROPHORE FROM BURKHOLDERIA (PSEUDOMONAS) CEPACIA", ZEITSCHRIFT FUER NATURFORSCHUNG. SECTION C. BIOSCIENCES, vol. 51, no. 9/10, 1 September 1996 (1996-09-01), pages 627 - 630, XP000617477, ISSN: 0341-0382 *
K. HIGASHI ET AL.: "Cutinostatin B as a new cutinase inhibitor produced by Actinomycete", BIOSCIENCE BIOTECHNOLOGY BIOCHEMISTRY., vol. 60, no. 3, 1996, JAPAN SOC. FOR BIOSCIENCE, BIOTECHNOLOGY AND AGROCHEM. TOKYO, JP, pages 401 - 404, XP002115282, ISSN: 0916-8451 *
KUNZE B ET AL: "MYXOCHELIN A, A NEW IRON-CHELATING COMPOUNDS FROM ANGIOCOCCUS DISCIFORMIS (MYXOBACTERALES). PRODUCTION, ISOLATION, PHYSICO -CHEMICAL AND BIOLOGICAL PROPERTIES", JOURNAL OF ANTIBIOTICS, vol. 42, no. 1, 1 January 1989 (1989-01-01), pages 14 - 17, XP000616420, ISSN: 0021-8820 *
MCKEE J A ET AL: "Iron transport mediated drug delivery systems: synthesis and antibacterial activity of spermidine- and lysine-based siderophore -.beta.-lactam conjugates", BIOCONJUGATE CHEM. (BCCHES,10431802);1991; VOL.2 (4); PP.281-91, Univ. Notre Dame;Dep. Chem. Biochem.; Notre Dame; 46556; IN; USA (US), XP002115891 *
PERSMARK M ET AL: "Iron(III) complexes of chrysobactin, the siderophore of Erwinia chrysanthemi", BIOMETALS (BOMEEH,09660844);1992; VOL.5 (1); PP.29-36, Univ. California;Div. Biochem. Mol. Biol.; Berkeley; CA; USA (US), XP002115892 *
PERSMARK M ET AL: "Isolation, characterization, and synthesis of chrysobactin, a compound with siderophore activity from Erwinia chrysanthemi", J. BIOL. CHEM. (JBCHA3,00219258);1989; VOL.264 (6); PP.3187-93, Univ. California;Biochem. Dep.; Berkeley; 94720; CA; USA (US), XP002115283 *
TARAZ K ET AL: "Bacteria components. XL. Protochelin, a catecholate siderophore from a bacterium (DMS No. 5746)", Z. NATURFORSCH., B: CHEM. SCI. (ZNBSEN,09320776);1990; VOL.45 (9); PP.1327-32, Univ. Cologne;Inst. Org. Chem.; Cologne; D-5000/41; Fed. Rep. Ger. (DE), XP002115890 *

Also Published As

Publication number Publication date
AU3253699A (en) 1999-09-06
WO1999042435A2 (en) 1999-08-26

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