CA2473988A1 - Drechsleranol derivatives, method for the production and use thereof - Google Patents

Drechsleranol derivatives, method for the production and use thereof Download PDF

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Publication number
CA2473988A1
CA2473988A1 CA002473988A CA2473988A CA2473988A1 CA 2473988 A1 CA2473988 A1 CA 2473988A1 CA 002473988 A CA002473988 A CA 002473988A CA 2473988 A CA2473988 A CA 2473988A CA 2473988 A1 CA2473988 A1 CA 2473988A1
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compound
formula
dsm
iii
tolerable salt
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CA002473988A
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CA2473988C (en
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Claudia Eder
Michael Kurz
Luigi Toti
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Sanofi Aventis Deutschland GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/04—Chelating agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/145—Fungal isolates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Toxicology (AREA)
  • Psychiatry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Anesthesiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention relates to novel, Drechslera anoles of known compounds of formula (I), which are formed during fermentation of the microorganisms Drechslera australiensis, ST 003360, DSM 14093, or ST 004112, DSM 14524. The invention also relates to a method for the production thereof, the use of said Drechslera anoles as medicaments, especially in the treatment and/or prophylaxis of degenerative neuropathies, for example, Alzheimer's disease or mental illnesses, such as depression, sleep disorders or seasonally related disorders, and the use of Drechslera anoles as chelating agents or antioxidants.

Claims (21)

1. A compound of the formula (I) where R is H, or a group of the formula -(CH(OR2))5-CH2-OR2, and R1 and R2 independently of one another are 1.0 H or
2.0 a C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C5-C10-aryl group, in which alkyl, alkenyl and alkynyl are straight-chain or branched, and in which the groups are optionally mono- or disubstituted by:
2.1 -OH, 2.2 =O, 2.3 -O-C1-C6-alkyl, in which alkyl is straight-chain or branched, 2.4 -O-C2-C6-alkenyl, in which alkenyl is straight-chain or branched, 2.5 -aryl, 2.6 -NH-C1-C6-alkyl, in which alkyl is straight-chain or branched, 2.7 -NH-C2-C6-alkenyl, in which alkenyl is straight-chain or branched, 2.8-NH2 or 2.9 halogen, in which the substituents 2.3 to 2.7 can further be substituted by -CN, -amide or -oxime functions, or a stereoisomeric form of the compound of the formula (I) or a physiologically tolerable salt of the compound of the formula (I) or a physiologically tolerable salt of a stereoisomeric form of a compound of the formula (I).

2. A compound of the formula (I) as claimed in claim 1, where R is H or a group of the formula -(CH(OR2))5-CH2-OR2, R1 and R2 independently of one another are H or C1-C6-alkyl, in which C1-C6-alkyl is straight-chain or branched and optionally mono- or disubstituted by the radicals 2.1 to 2.9.
3. A compound of the formula (I) as claimed in claim 1, characterized in that it has the formula (II) or a stereoisomeric form of the compound of the formula (II) or a physiologically tolerable salt of the compound of the formula (II) or or a physiologically tolerable salt of a stereoisomeric form of a compound of the formula (II).
4. A compound of the formula (I) as claimed in claim 1, characterized in that it has the formula (III) or a stereoisomeric form of the compound of the formula (III) or a physiologically tolerable salt of the compound of the formula (III) or or a physiologically tolerable salt of a stereoisomeric form of a compound of the formula (III).
5. A compound of the empirical formula C26H24O9, further characterized by the NMR data .delta. = 3.25, 3.34, 3.39, 3.45, 3.62, 3.69, 4.62, 6.75, 6.75, 7.25, 7.26, 7.28, 7.30, 7.38, 7.45, 7.62 and the 13C-NMR data .delta. = 61.37, 70.47, 73.43, 78.4 (broad), 78.91, 81.29, 107.91, 108.19, 115.15, 115.27, 115.83, 117.58, 118.06, 118.72, 119.16, 124.95, 125.99, 126.37, 129.9 (broad), 130.13, 134.57, 135 66, 152.27, 152.57, 154.50, 154.76.
6. A compound of the empirical formula C20H12O3, further characterized by the NMR data .delta. = 6.69, 7.22, 7.24, 7.31, 7.46 and the 13C-NMR data .delta. =
109.20, 117.5, 119.55, 119.55; 121.3, 127.52, 130.63, 137.60, 154.3, 157Ø
7. A compound of the formula (II) as claimed in claim 3 or a pharmacologically tolerable salt of a compound of the formula (II), obtainable by fermentation of ST
003360 (DSM 14093) or of a variant and/or mutants of ST 003360 (DSM 14093) in a culture medium until the compound of the formula (II) accumulates in the culture broth, subsequent isolation of the compound of the formula (II), and, if appropriate, conversion into a pharmacologically tolerable salt of the compound of the formula (II).
8. A compound of the formula (III) as claimed in claim 4 or a pharmacologically tolerable salt of a compound of the formula (III), obtainable by fermentation of ST
004112 (DSM 14524) or of a variant and/or mutants of ST 004112 (DSM 14524) in a culture medium until the compound of the formula (III) accumulates in the culture medium, subsequent isolation of the compound of the formula (III), and, if appropriate, conversion into a pharmacologically tolerable salt of the compound of the formula (III).
9. A compound of the formula (I) as claimed in claim 1 or a pharmacologically tolerable salt of a compound of the formula (I), obtainable by fermentation of ST
003360 (DSM 14093) or of a variant and/or mutants of ST 003360 (DSM 14093) in a culture medium until the compound of the formula (II) accumulates in the culture broth, subsequent isolation of the compound of the formula (II), or fermentation of ST
004112 (DSM 14524) or of a variant and/or mutants of ST 004112 (DSM 14524) in a culture medium until the compound of the formula (III) accumulates in the culture medium, subsequent isolation of the compound of the formula (III), and subsequent conversion into a compound of the formula (I), and, if appropriate, conversion into a pharmacologically tolerable salt of the compound of the formula (I).
10. A process for the preparation of the compound of the formula (II) as claimed in claim 3 or pharmacologically tolerable salt of a compound of the formula (II), characterized in that it comprises a) culturing the microorganism ST 003360 (DSM 14093) or a variant and/or mutant of ST 003360 (DSM 14093), b) isolating and purifying a compound of the formula (II), and c) converting the compound of the formula (II), if appropriate, into an obvious chemical equivalent and/or a pharmacologically tolerable salt.
11. A process for the preparation of the compound of the formula (III) as claimed in claim 4 or of a pharmacologically tolerable salt of a compound of the formula (III), characterized in that it comprises a) culturing the microorganism ST 004112 (DSM 14524) or a variant and/or mutant of ST 004112 (DSM 14524), b) isolating and purifying a compound of the formula (III), and c) converting the compound of the formula (III), if appropriate, into an obvious chemical equivalent and/or a pharmacologically tolerable salt.
12. A process for the preparation of a compound of the formula (I) as claimed in claim 1 or of a pharmacologically tolerable salt of a compound of the formula (I), characterized in that it comprises a) culturing the microorganism ST 003360 (DSM 14093) or a variant and/or mutants of ST 003360 (DSM 14093) in a culture medium, and isolating and purifying the compound of the formula (II), or culturing the microorganism ST 004112 (DSM 14524) or a variant and/or mutants of ST 004112 (DSM 14524) in a culture medium, and isolating and purifying the compound of the formula (III), and b) converting a compound of the formula (II) or a compound of the formula (III) into a compound of the formula (I), and c) converting the compound of the formula (I), if appropriate, into a pharmacologically tolerable salt.
13. The use of a compound as claimed in one of claims 1 to 9 for the production of a pharmaceutical.
14. The use of a compound as claimed in one of claims 1 to 9 for the production of a pharmaceutical for the therapy and/or prophylaxis of degenerative neuropathies.
15. The use of a compound as claimed in one of claims 1 to 9 for the production of a pharmaceutical for the therapy and/or prophylaxis of Alzheimer's disease.
16. The use of a compound as claimed in one of claims 1 to 9 for the production of a pharmaceutical for the therapy and/or prophylaxis of psychological disorders.
17. The use of a compound as claimed in one of claims 1 to 9 for the production of a pharmaceutical for the therapy and/or prophylaxis of depressions, sleep disturbances or seasonally related affective disorders.
18. The use of a compound as claimed in one of claims 1 to 9 as a chelating agent or antioxidant.
19. A pharmaceutical containing at least one compound as claimed in one or more of claims 1 to 9 and one or more physiologically suitable excipients.
20. The strain Drechslera australiensis, ST 003360, DSM 14093.
21. The strain ST 004112, DSM 14524.
CA2473988A 2002-01-29 2003-01-20 Drechsleranol derivatives, method for the production and use thereof Expired - Fee Related CA2473988C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10203557.1 2002-01-29
DE10203557A DE10203557A1 (en) 2002-01-29 2002-01-29 Drechsleranol derivatives, process for their preparation and their use
PCT/EP2003/000487 WO2003064405A1 (en) 2002-01-29 2003-01-20 Drechslera anole derivatives, method for the production and use thereof

Publications (2)

Publication Number Publication Date
CA2473988A1 true CA2473988A1 (en) 2003-08-07
CA2473988C CA2473988C (en) 2011-05-03

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CA2473988A Expired - Fee Related CA2473988C (en) 2002-01-29 2003-01-20 Drechsleranol derivatives, method for the production and use thereof

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EP (1) EP1472240B1 (en)
JP (1) JP4436134B2 (en)
AR (1) AR038233A1 (en)
AT (1) ATE466848T1 (en)
AU (1) AU2003201963B2 (en)
BR (1) BR0307199A (en)
CA (1) CA2473988C (en)
DE (2) DE10203557A1 (en)
IL (1) IL163166A (en)
MX (1) MXPA04006358A (en)
PE (1) PE20030815A1 (en)
WO (1) WO2003064405A1 (en)

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* Cited by examiner, † Cited by third party
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CN105339362B (en) * 2013-06-26 2017-09-01 Dic株式会社 Compound containing phenolic hydroxyl group, phenolic resin, solidification compound, its solidfied material, semiconductor-encapsulating material and tellite

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JP3068706B2 (en) * 1992-02-26 2000-07-24 塩野義製薬株式会社 Aldose reductase inhibitor

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EP1472240B1 (en) 2010-05-05
EP1472240A1 (en) 2004-11-03
AR038233A1 (en) 2005-01-05
DE50312692D1 (en) 2010-06-17
BR0307199A (en) 2004-11-03
JP4436134B2 (en) 2010-03-24
AU2003201963B2 (en) 2008-06-05
MXPA04006358A (en) 2004-10-04
WO2003064405A1 (en) 2003-08-07
ATE466848T1 (en) 2010-05-15
PE20030815A1 (en) 2003-10-10
CA2473988C (en) 2011-05-03
DE10203557A1 (en) 2003-08-07
IL163166A (en) 2008-08-07
JP2006503797A (en) 2006-02-02

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