AR035240A1 - DECALACTONES OF FUNGES ASSOCIATED WITH MARINE SPONGE AND ITS SYNTHETIC DERIVATIVES AS MEDICINES - Google Patents

DECALACTONES OF FUNGES ASSOCIATED WITH MARINE SPONGE AND ITS SYNTHETIC DERIVATIVES AS MEDICINES

Info

Publication number
AR035240A1
AR035240A1 ARP020101674A ARP020101674A AR035240A1 AR 035240 A1 AR035240 A1 AR 035240A1 AR P020101674 A ARP020101674 A AR P020101674A AR P020101674 A ARP020101674 A AR P020101674A AR 035240 A1 AR035240 A1 AR 035240A1
Authority
AR
Argentina
Prior art keywords
straight
branched chain
chain alkyl
alkyl
branched
Prior art date
Application number
ARP020101674A
Other languages
Spanish (es)
Original Assignee
Zentaris Ag
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
Application filed by Zentaris Ag filed Critical Zentaris Ag
Publication of AR035240A1 publication Critical patent/AR035240A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • 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
    • 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
    • C12P17/08—Oxygen as only ring hetero atoms containing a hetero ring of at least seven ring members, e.g. zearalenone, macrolide aglycons

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Wood Science & Technology (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pyrane Compounds (AREA)

Abstract

Se describe un aislamiento, el esclarecimiento de la estructura, la síntesis y el uso de decalactonas y sus derivados como medicamentos. Las nuevas sustancias naturales fueron aisladas del caldo del cultivo de un hongo que existe asociado con una esponja marina. Además se describe la síntesis de estas sustancias naturales y de sus derivados. Las sustancias naturales descritas y los derivados sintéticos de estas sustancias naturales pueden ser utilizados como sustancias activas en medicamentos, especialmente contra enfermedades de cáncer y como agentes anti-infecciosos. Reivindicación 1: Compuestos de fórmula general (1) donde: el resto R1 puede ser H, (C1-6)alquilo de cadena recta o ramificada, (C1-6)alquilo sustituido una o varias veces por (C6-14)arilo, carboxi-(C1-18)alquilo de cadena recta o ramificada, (C1-6)alcoxicarbonilo de cadena recta o ramificada, (C1-12)alquilcarbonilo de cadena recta o ramificada, (C2-6)alquenilo, (C2-6)alquinilo, ciano(C1-6)alquilo de cadena recta o ramificada, o benciloxi, 9-fluorenilmetoxi-carbonilo (Fmoc-), trifenilmetilo (Tr-), 2-(4'-piridil)etoxicarbonilo (Pyoc-) o difenilmetilsililo (DPMS-); el resto R2 puede ser H, (C1-6)alquilo de cadena recta o ramificada, (C1-6)alquilo sustituido una o varias veces por (C6-14)arilo, carboxi-(C1-18)alquilo de cadena recta o ramificada, (C1-6)alcoxicarbonilo de cadena recta o ramificada, (C1-12)alquilcarbonilo de cadena recta o ramificada, (C2-6)alquenilo, (C2-6)alquinilo, ciano-(C1-6)alquilo de cadena recta o ramificada, o benciloxi, 9-fluorenilmetoxi-carbonilo (Fmoc-), trifenilmetilo (Tr-), 2-(4'-piridil)etoxicarbonilo (Pyoc-) o difenilmetilsililo (DPMS-); X puede ser O ó S, NOH, NOR4 donde R4 puede ser (C1-6)alquilo de cadena recta o ramificada, (C1-6)alquilo sustituido una o varias veces por (C6-14)arilo, carboxi-(C1-18)alquilo de cadena recta o ramificada; (C1-6)alcoxicarbonilo de cadena recta o ramificada, (C1-12)alquilcarbonilo de cadena recta o ramificada; Y puede ser O ó S; y Z puede ser H u OR3, donde R3 puede ser H, (C1-6)alquilo de cadena recta o ramificada, (C1-6)alquilo sustituido una o varias veces por (C6-14)arilo, carboxi-(C1-18)alquilo de cadena recta o ramificada; (C1-6)alcoxicarbonilo de cadena recta o ramificada, (C1-12)alquilcarbonilo de cadena recta o ramificada, (C2-6)alquenilo, (C1-6)alquinilo, ciano-(C1-6)alquilo de cadena recta o ramificada, o benciloxi, 9-fluorenilmetoxi-carbonilo (Fmoc-), trifenilmetilo (Tr-), 2-(4'-piridil)etoxicarbonilo (Pyoc-) o difenilmetilsililo (DPMS-). Reivindicación 5: Un procedimiento para elaborar o aislar un compuesto según la fórmula (1), conforme a las reivindicaciones de 1 a 4. Reivindicación 6: Un procedimiento para aislar los compuestos según la fórmula (1) conforme a la reivindicación 5, comprendiendo los pasos: cultivo del hongo Penicillium sp., extracción de un caldo del cultivo del hongo Penicillium sp. con un solvente orgánico, purificación del extracto, separación y purificación de los compuestos conformes a la fórmula general (1). Reivindicación 7: Procedimiento para elaborar los compuestos según la fórmula (1), conforme a la reivindicación 5, mediante síntesis química conforme al esquema A.An isolation, elucidation of the structure, synthesis and use of decalactones and their derivatives as medicaments is described. The new natural substances were isolated from the broth of the cultivation of a fungus that exists associated with a sea sponge. In addition, the synthesis of these natural substances and their derivatives is described. The described natural substances and synthetic derivatives of these natural substances can be used as active substances in medicines, especially against cancer diseases and as anti-infectious agents. Claim 1: Compounds of general formula (1) wherein: the moiety R1 can be H, (C1-6) straight or branched chain alkyl, (C1-6) alkyl substituted once or several times by (C6-14) aryl, carboxy- (C1-18) straight or branched chain alkyl, (C1-6) straight or branched chain alkoxycarbonyl, (C1-12) straight or branched chain alkylcarbonyl, (C2-6) alkenyl, (C2-6) alkynyl, cyano (C1-6) straight or branched chain alkyl, or benzyloxy, 9-fluorenylmethoxycarbonyl (Fmoc-), triphenylmethyl (Tr-), 2- (4'-pyridyl) ethoxycarbonyl (Pyoc-) or diphenylmethylsilyl ( DPMS-); the radical R2 may be H, (C1-6) straight or branched chain alkyl, (C1-6) alkyl substituted once or several times by (C6-14) aryl, carboxy- (C1-18) straight chain alkyl or branched, (C1-6) straight or branched chain alkoxycarbonyl, (C1-12) straight or branched chain alkylcarbonyl, (C2-6) alkenyl, (C2-6) alkynyl, cyano- (C1-6) chain alkyl straight or branched, or benzyloxy, 9-fluorenylmethoxycarbonyl (Fmoc-), triphenylmethyl (Tr-), 2- (4'-pyridyl) ethoxycarbonyl (Pyoc-) or diphenylmethylsilyl (DPMS-); X can be O or S, NOH, NOR4 where R4 can be (C1-6) straight or branched chain alkyl, (C1-6) alkyl substituted once or several times by (C6-14) aryl, carboxy- (C1- 18) straight or branched chain alkyl; (C1-6) straight or branched chain alkoxycarbonyl, (C1-12) straight or branched chain alkylcarbonyl; And it can be O or S; and Z can be H or OR3, where R3 can be H, (C1-6) straight or branched chain alkyl, (C1-6) alkyl substituted once or several times by (C6-14) aryl, carboxy- (C1- 18) straight or branched chain alkyl; (C1-6) straight or branched chain alkoxycarbonyl, (C1-12) straight or branched chain alkylcarbonyl, (C2-6) alkenyl, (C1-6) alkynyl, cyano- (C1-6) straight chain alkyl or branched, or benzyloxy, 9-fluorenylmethoxycarbonyl (Fmoc-), triphenylmethyl (Tr-), 2- (4'-pyridyl) ethoxycarbonyl (Pyoc-) or diphenylmethylsilyl (DPMS-). Claim 5: A process for preparing or isolating a compound according to formula (1), according to claims 1 to 4. Claim 6: A process for isolating compounds according to formula (1) according to claim 5, comprising steps: cultivation of the fungus Penicillium sp., extraction of a broth from the cultivation of the fungus Penicillium sp. with an organic solvent, extract purification, separation and purification of the compounds according to the general formula (1). Claim 7: Process for preparing the compounds according to formula (1), according to claim 5, by chemical synthesis according to scheme A.

ARP020101674A 2001-05-09 2002-05-08 DECALACTONES OF FUNGES ASSOCIATED WITH MARINE SPONGE AND ITS SYNTHETIC DERIVATIVES AS MEDICINES AR035240A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10122523A DE10122523A1 (en) 2001-05-09 2001-05-09 New 1,3-dihydroxybenzo-fused decalactone compounds, are cellular kinase inhibitors and hormone receptor inhibitors, useful as e.g. antitumor, anti-infective, antifungal and antiprotozoal drugs

Publications (1)

Publication Number Publication Date
AR035240A1 true AR035240A1 (en) 2004-05-05

Family

ID=7684155

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP020101674A AR035240A1 (en) 2001-05-09 2002-05-08 DECALACTONES OF FUNGES ASSOCIATED WITH MARINE SPONGE AND ITS SYNTHETIC DERIVATIVES AS MEDICINES

Country Status (5)

Country Link
EP (1) EP1474413A2 (en)
JP (1) JP2004534756A (en)
AR (1) AR035240A1 (en)
DE (1) DE10122523A1 (en)
WO (1) WO2002092589A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101620815B1 (en) 2014-05-21 2016-05-13 한국생명공학연구원 Composition for the prevention and treatment of inflammatory diseases comprising the penicillinolide A isolated from marine fungi

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0497300A1 (en) * 1991-01-30 1992-08-05 Hoechst Aktiengesellschaft Natural products with ten-ring lactone structure, method for their preparation and their use

Also Published As

Publication number Publication date
DE10122523A1 (en) 2002-11-14
WO2002092589A2 (en) 2002-11-21
WO2002092589A3 (en) 2004-09-02
JP2004534756A (en) 2004-11-18
EP1474413A2 (en) 2004-11-10

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