Nova Patents
EP0356399A2

Substituted 4-azatricyclo (22.3.1.04.9) octacos-18-ene derivatives, their preparation and pharmaceutical compositions containing them.

Abstract

The compounds of formula I wherein either R₁ is hydroxy, R₂ is allyl or n-propyl and there is a single bond between the carbon atoms numbered 14 and 15 or R₁ is missing, R₂ is allyl and there is a double bond between the carbon atoms numbered 14 and 15, have interesting immunosuppressant and anti-inflammatory properties. They are obtained by fermentation or synthesis, e.g. by hydrogenation or dehydration.

EP0356399A2, drawing sheet 1
Sheet 1 of 9

Term

Term ended

Projected expiry passed 22 August 2009, 17.1 years ago.

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10 claims: 3 independent, 7 dependent

  1. 1
    A compound of formula I wherein either R₁ is hydroxy, R₂ is allyl or n-propyl and there is a single bond between the carbon atoms numbered 14 and 15 or R₁ is missing, R₂ is allyl and there is a double bond between the carbon atoms numbered 14 and 15. 1. A process for the preparation of a compound of formula I wherein either R₁ is hydroxy, R₂ is allyl or n-propyl and there is a single bond between the carbon atoms numbered 14 and 15 or R₁ is missing, R₂ is allyl and there is a double bond between the carbon atoms numbered 14 and 15 which comprises a) for the preparation of the compounds of formula I wherein R₁ is hydroxy or missing and R₂ is allyl, cultivating an appropriate Streptomyces strain such as Streptomyces tsukubaensis No. 9993 and isolating the compounds from the resultant culture orb) for the preparation of the compound of formula I wherein R₁ is missing and R₂ is allyl, dehydrating the corresponding compound of formula I wherein R₁ is hydroxy.
  2. 4
    A process according to claim 1 or 2 for the preparation of the compounds according to claim 1 wherein either R₁ is hydroxy, R₂ is n-propyl and there is a single bond between the carbon atoms numbered 14 and 15 or R₁ is missing, R₂ is allyl and there is a double bond between the carbon atoms numbered 14 and 15. 4. A process for the preparation of a compound of formula I as defined in claim 1 which comprises a) for the preparation of the compounds of formula I wherein R₁ is hydroxy or missing and R₂ is allyl, cultivating an appropriate Streptomyces strain such as Streptomyces tsukubaensis No. 9993 and isolating the compounds from the resultant culture orb) for the preparation of the compound of formula I wherein R₁ is missing and R₂ is allyl, dehydrating the corresponding compound of formula I wherein R₁ is hydroxy.
  3. 5
    A process for the preparation of a pharmaceutical composition comprising mixing a compound of formula I as defined in claim 1 with a pharmaceutically acceptable carrier or diluent. 5. A process for the preparation of the compound of formula I wherein R₁ is hydroxy, R₂ is n-propyl and there is a single bond between the carbon atoms numbered 14 and 15 which comprises hydrogenating the corresponding compound of formula I wherein R₂ is allyl.
Independent claims3