HK18596A - Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same - Google Patents

Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same Download PDF

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Publication number
HK18596A
HK18596A HK18596A HK18596A HK18596A HK 18596 A HK18596 A HK 18596A HK 18596 A HK18596 A HK 18596A HK 18596 A HK18596 A HK 18596A HK 18596 A HK18596 A HK 18596A
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Hong Kong
Prior art keywords
compound
hydroxy
substance
formula
allyl
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HK18596A
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English (en)
French (fr)
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Okuhara Masakuni
Tanaka Hirokazu
Goto Toshio
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Fujisawa Pharmaceutical Co., Ltd.
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Priority claimed from GB848430455A external-priority patent/GB8430455D0/en
Priority claimed from GB858502869A external-priority patent/GB8502869D0/en
Priority claimed from GB858508420A external-priority patent/GB8508420D0/en
Application filed by Fujisawa Pharmaceutical Co., Ltd. filed Critical Fujisawa Pharmaceutical Co., Ltd.
Publication of HK18596A publication Critical patent/HK18596A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
    • 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; 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
    • C12N1/20—Bacteria; Culture media therefor
    • C12N1/205—Bacterial 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
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • 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
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/465—Streptomyces
    • 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
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/465—Streptomyces
    • C12R2001/55—Streptomyces hygroscopicus
    • 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
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/886—Streptomyces
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/886—Streptomyces
    • Y10S435/898—Streptomyces hygroscopicus

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (26)

  1. Verbindung der Formel worin bedeuten:
    R¹   Hydroxy oder in konventioneller Weise geschütztes Hydroxy,
    R²   Wasserstoff, Hydroxy oder in konventioneller Weise geschütztes Hydroxy,
    R³   Methyl, Ethyl, Propyl oder Allyl,
    n   die ganze Zahl 1 oder 2 und das Symbol aus einer Linie und einer gestrichelten Linie eine Einfachbindung oder eine Doppelbindung, mit der Maßgabe, daß dann, wenn R¹ und R² jeweils für Hydroxy stehen, n für die ganze Zahl 2 steht und das Symbol aus einer Linie und einer gestrichelten Linie für eine Einfachbindung steht, R³ Methyl, Propyl oder Allyl darstellt, und ein Salz derselben.
  2. Verbindung nach Anspruch 1, die durch die folgende Formel dargestellt werden kann worin bedeuten:
    R¹   Hydroxy oder in konventioneller Weise geschütztes Hydroxy,
    R²   Hydroxy oder in konventioneller Weise geschütztes Hydroxy und
    R³   Methyl, Propyl oder Allyl.
  3. Verbindung nach Anspruch 2, worin R³ für Allyl steht.
  4. Verbindung nach Anspruch 3, worin R¹ für Hydroxy, 1-(C₁-C₆-Alkylthio)(C₁-C₆)alkoxy, Tri(C₁-C₆)alkylsilyloxy, C₁-C₆-Alkyl-diphenylsilyloxy oder Acyloxy steht.
  5. Verbindung nach Anspruch 4, worin stehen:
    R¹   für Hydroxy; C₁-C₆-Alkylthiomethoxy; Tri(C₁-C₆)alkylsilyloxy; C₁-C₆-Alkyl-diphenylsilyloxy; C₁-C₆-Alkanoyloxy, das Carboxy aufweisen kann; Cyclo(C₃-C₆)alkoxy(C₁-C₆)alkanoyloxy, das zwei C₁-C₆-Alkylgruppen an dem Cycloalkylrest aufweisen kann; Campfersulfonyloxy; Aroyloxy, das ein oder zwei Nitro aufweisen kann, wobei der Aroylrest ausgewählt wird aus der Gruppe, die besteht aus Benzoyl, Toluoyl, Xyloyl und Naphthoyl; Arensulfonyloxy, das Halogen aufweisen kann, wobei der Arenrest ausgewählt wird aus der Gruppe, die besteht aus Benzol, Toluol, Xylol und Naphthalin; oder Phenyl(C₁-C₄)alkanoyloxy, das C₁-C₆Alkoxy und Trihalogen(C₁-C₆)alkyl aufweisen kann, und
    R²   für Hydroxy oder C₁-C₆-Alkanoyloxy.
  6. Verbindung nach Anspruch 5, bei der es sich handelt um    17-Allyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en -2,3,10,16-tetraon.
  7. Verbindung nach Anspruch 5, worin stehen:
    R¹   für C₁-C₆-Alkanoyloxy und
    R²   für Hydroxy oder C₁-C₆-Alkanoyloxy.
  8. Verbindung nach Anspruch 7, bei der es sich handelt um    12-[2-(4-Acetoxy-3-methoxycyclohexyl)-1-methylvinyl]-17-allyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en -2,3,10,16-tetraon .
  9. Verbindung nach Anspruch 7, bei der es sich handelt um    14-Acetoxy-12-[2-(4-acetoxy-3-methoxycyclohexyl)-1-methylvinyl]-17-allyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en -2,3,10,16-tetraon .
  10. Verbindung nach Anspruch 2, bei der es sich handelt um    1,14-Dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,17,21,27-pentamethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en -2,3,10,16-tetraon .
  11. Verbindung nach Anspruch 1, worin stehen:
    R¹   für Hydroxy, C₁-C₆-Alkylthiomethoxy, C₁-C₆-Alkanoyloxy oder Arensulfonyloxy, das Halogen aufweisen kann, wobei der Arenrest ausgewählt wird aus der Gruppe, die besteht aus Benzol, Toluol, Xylol und Naphthalin,
    R²   für Wasserstoff oder Hydroxy,
    n   für die ganze Zahl 2 und
    das Symbol aus einer Linie und einer gestrichelten Linie für eine Doppelbindung.
  12. Verbindung nach Anspruch 1, bei der es sich handelt um    16-Allyl-1,13-dihydroxy-11-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-22,24-dimethoxy-12,18,20,26-tetramethyl-10,27-dioxa-4-azatricyclo[21.3.1.04,8]heptacos-17-en -2,3,9,15-tetraon .
  13. Verfahren zur Herstellung der Verbindung der Formel worin bedeuten:
    R¹   Hydroxy oder in konventioneller Weise geschütztes Hydroxy,
    R²   Wasserstoff, Hydroxy oder in konventioneller Weise geschütztes Hydroxy,
    R³   Methyl, Ethyl, Propyl oder Allyl,
    n   die ganze Zahl 1 oder 2 und das Symbol aus einer Linie und einer gestrichelten Linie eine Einfachbindung oder eine Doppelbindung, mit der Maßgabe, daß dann, wenn R¹ und R² jeweils für Hydroxy stehen, n für die ganze Zahl 2 steht und das Symbol aus einer Linie und einer gestrichelten Linie für eine Einfachbindung steht, R³ Methyl, Propyl oder Allyl darstellt,
    und eines Salzes derselben, das umfaßt
    a) das Kultivieren von Streptomyces tsukubaensis in einem wäßrigen Nährmedium, das Quellen für assimilierbaren Kohlenstoff und Stickstoff enthält, und das Gewinnen (Abtrennen) der FR-900506- und/oder FR-900525-Substanz(en) auf konventionelle Weise unter Bildung der FR-900506-Substanz der Formel und/oder der FR-900525-Substanz der Formel
    b) das Kultivieren von Streptomyces hygroscopicus in einem wäßrigen Nährmedium, das Quellen für assimilierbaren Kohlenstoff und Stickstoff enthält, und das Gewinnen (Abtrennen) der FR-900523-Substanz der nachstehend angegebenen Formel auf konventionelle Weise
    c) das Einführen einer konventionellen Hydroxyschutzgruppe in eine Verbindung der Formel worin R², R³, n und das Symbol aus einer Linie und einer gestrichelten Linie jeweils wie oben definiert sind, unter Bildung einer Verbindung der Formel worin R², R³, n und das Symbol aus einer Linie und einer gestrichelten Linie jeweils wie oben definiert sind, und worin R¹a für in konventioneller Weise geschütztes Hydroxy steht, oder eines Salzes derselben auf an sich bekannte Weise;
    d) die Einführung einer konventionellen Hydroxyschutzgruppe in eine Verbindung der Formel worin R¹, R³, n und das Symbol aus einer Linie und einer gestrichelten Linie jeweils wie oben definiert sind, oder eines Salzes derselben unter Bildung einer Verbindung der Formel worin R¹, R³, n und das Symbol aus einer Linie und einer gestrichelten Linie jeweils wie oben definiert sind, und worin R²a für in konventioneller Weise geschütztes Hydroxy steht, oder eines Salzes derselben auf an sich bekannte Weise;
    e) die Umsetzung einer Verbindung der Formel worin R¹, R³ und n jeweils wie oben definiert sind, und worin R²b für eine austretende Gruppe steht, oder eines Salzes derselben mit einer Base unter Bildung einer Verbindung der Formel worin R¹, R³ und n jeweils wie oben definiert sind, oder eines Salzes derselben auf an sich bekannte Weise;
    f) das Oxidieren einer Verbindung der Formel worin R¹, R³ und n jeweils wie oben definiert sind, oder eines Salzes derselben unter Bildung einer Verbindung der Formel worin R¹, R³ und n jeweils wie oben definiert sind, oder eines Salzes derselben auf an sich bekannte Weise; und
    g) das Reduzieren einer Verbindung der Formel worin R¹, R², n und das Symbol aus einer Linie und einer gestrichelten Linie jeweils wie oben definiert sind, oder eines Salzes derselben unter Bildung einer Verbindung der Formel worin R¹, R², n und das Symbol aus einer Linie und einer gestrichelten Linie jeweils wie oben definiert sind, oder eines Salzes derselben auf an sich bekannte Weise.
  14. Pharmazeutische Zusammensetzung, die als aktive Bestandteile (Wirkstoffe) Tricyclo-Verbindungen nach Anspruch 1 in Assoziation mit einem pharmazeutisch akzeptablen, im wesentlichen nicht-toxischen Träger oder Exzipienten enthält.
  15. Verwendung der Tricyclo-Verbindungen nach Anspruch 1 und nach Anspruch 20 zur Herstellung eines Arzneimittels für die Behandlung oder Verhinderung der Resistenz durch Transplantation, der Transplantat-gegen-WirtErkrankungen durch Knochenmarks-Transplantation und von Autoimmunerkrankungen.
  16. Verwendung der Tricyclo-Verbindungen nach Anspruch 1 zur Herstellung eines Arzneimittels.
  17. Verwendung der Tricycloverbindungen nach Anspruch 1 zur Herstellung eines Immununterdrückungsmittels oder eines antimikrobiellen Agens.
  18. Biologisch reine Kultur des Mikroorganismus Streptomyces tsukubaensis Nr. 9993.
  19. Biologisch reine Kultur des Mikroorganismus Streptomyces hygroscopicus subsp. yakushimaensis Nr. 7238.
  20. Verfahren zur Herstellung der FR-900520-Substanz der Formel das umfaßt das Kultivieren von Streptomyces tsukubaensis oder Streptomyces hygroscopicus subsp. yakushimaensis Nr. 7238 in einem wäßrigen Nährmedium, das Quellen für assimilierbaren Kohlenstoff und Stickstoff enthält, zur Bildung der FR-900520-Substanz.
  21. Tricyclo-Verbindung nach Anspruch 1 für die Verwendung als Arzneimittel.
  22. Tricyclo-Verbindung nach Anspruch 1 für die Verwendung als Immununterdrückungsmittel.
  23. Tricyclo-Verbindung nach Anspruch 1 für die Verwendung als Immununterdrückungsmittel nach Anspruch 22, wobei es sich bei der Tricyclo-Verbindung um die FR-900506-Substanz der folgenden Formel handelt
  24. Verfahren nach Anspruch 13 und nach Anspruch 20, wobei das Kultivieren unter aeroben Bedingungen durchgeführt wird.
  25. Verwendung des Mikroorganismus Streptomyces tsukubaensis Nr. 9993 zur Herstellung der FR-900506-Substanz der Formel der FR-900525-Substanz der Formel und/oder der FR-900520-Substanz der Formel
  26. Verwendung des Mikroorganismus Streptomyces hygroscopicus subsp. yakushimaensis Nr. 7238 zur Herstellung der FR-900523-Substanz der folgenden Formel und/oder der FR-900520-Substanz der Formel
HK18596A 1984-12-03 1996-02-01 Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same HK18596A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB848430455A GB8430455D0 (en) 1984-12-03 1984-12-03 Fr-900506 substance
GB858502869A GB8502869D0 (en) 1985-02-05 1985-02-05 Ws 7238 substances
GB858508420A GB8508420D0 (en) 1985-04-01 1985-04-01 Fr-900506 & fr-900525 substances

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HK18596A true HK18596A (en) 1996-02-09

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US (15) US4894366A (de)
EP (1) EP0184162B1 (de)
JP (6) JPH0372483A (de)
KR (5) KR930010704B1 (de)
CN (1) CN1013687B (de)
AT (1) ATE104984T1 (de)
AU (1) AU592067B2 (de)
CA (1) CA1338491C (de)
CY (1) CY1912A (de)
DE (2) DE3587806T2 (de)
DK (1) DK169550B1 (de)
ES (1) ES8705038A1 (de)
FI (2) FI87803C (de)
GR (1) GR852904B (de)
HK (1) HK18596A (de)
HU (1) HU195250B (de)
IE (1) IE62865B1 (de)
IL (2) IL92345A (de)
LU (1) LU90317I2 (de)
MX (1) MX9202943A (de)
NL (1) NL960023I2 (de)
NO (1) NO168372C (de)
NZ (1) NZ214407A (de)
PT (1) PT81589B (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4894366A (en) * 1984-12-03 1990-01-16 Fujisawa Pharmaceutical Company, Ltd. Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same
US5266692A (en) * 1984-12-03 1993-11-30 Fujisawa Pharmaceutical Co., Ltd. Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same
US5254562A (en) * 1984-12-03 1993-10-19 Fujisawa Pharmaceutical Company, Ltd. Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same
GB8608080D0 (en) * 1986-04-02 1986-05-08 Fujisawa Pharmaceutical Co Solid dispersion composition
EP0293892B1 (de) * 1987-06-05 1993-12-15 Fujisawa Pharmaceutical Co., Ltd. Anti-FR-900506-Stoffe-Antikörper und höchstempfindliches Enzym-Immunoassay-Verfahren
DE3737523A1 (de) * 1987-11-05 1989-05-18 Bayer Ag Verwendung von substituierten hydroxypiperidinen als antivirale mittel
AT400808B (de) * 1987-11-09 1996-03-25 Sandoz Ag Verwendung von tricyclischen verbindungen zur herstellung von topischen arzneimitteln
DE3844904C2 (de) * 1987-11-09 1997-01-30 Sandoz Ag Neue Verwendung von 11,28-Dioxa-4-azatricyclo-[22.3.1.0·4·,·9·]octacos-18-en-Derivaten
CH677448A5 (de) * 1987-11-09 1991-05-31 Sandoz Ag
DE3838035C2 (de) * 1987-11-09 1994-03-24 Sandoz Ag Neue Verwendung von 11,28-dioxa-4-azatricyclo[22.3.1.O·4··,··9·]octacos-18-en-Derivaten
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