Pregna-1,4-diene3,20-dione-16-17-acetal-21 esters, process for their preparation, composition, and methods for the treatment of inflammatory conditions

• US 5,482,934 A
• Filed: 07/20/1994
• Issued: 01/09/1996
• Est. Priority Date: 09/07/1990
• Status: Expired due to Term

• Current Assignee: Astrazeneca AB (Astrazeneca PLC)
• Original Assignee: Especialidades Latinas Medicamentos Universales SA
• Inventors: Conde, Jose R., Calatayud, Jose, Luna, Manuel
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): Grumbling, Matthew V.
• Application Number:
  US08/278,112
• Time in Patent Office: 538 Days
• Field of Search: 540/63, 540/70, 514/174, 552/565, 552/566
• US Class Current: 514/174
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 5/44 Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
• CPC Class Codes: C07J 5/0092 by an OH group free esterified or etherified
• CPC Class Codes: C07J 71/0031 at positions 16, 17

Abstract

The present invention relates to compounds of the formula: ##STR1## in which X₁ and X₂ correspond to H or F without distinction; R₁ represents the following radicals: ##STR2## and R₂ represents the radicals ##STR3## in the form of an R epimer, an S epimer, or a stereoisomeric mixture of the R and S epimers in terms of the orientation of the substituents on the carbon atom at position 22, novel intermediates and a method of their preparation by hydrolysis-ketalization, and use of such compounds as drugs and/or therapeutic agents.

Claims

1. A compound of the formula ##STR20## in the form of an R epimer, an S epimer, or a stereoisomeric mixture of the R and S epimers in terms of the orientation of the substituents on the carbon atom at position 22, wherein:

R₁ is cyclohexyl,

R₂ is a member selected from the group consisting of ##STR21## and wherein X₁ and X₂ may be the same or different and each is a member selected from the group consisting of hydrogen and fluorine.

2. A compound according to claim 1 in the form of the (22S)- epimer.

3. A compound according to claim 1 in the form of the (22R)- epimer.

4. An anti-inflammatory drug containing a compound according to claim 1.

5. A method of treating inflammatory conditions which comprises administering to a patient an anti-inflammatory effective amount of a compound according to claim 1.

6. A pharmaceutical composition having anti-inflammatory properties comprising as the active ingredient an effective amount of a compound according to claim 1 together with a pharmaceutically acceptable carrier.

7. A method for the treatment and control of inflammatory conditions characterized by the topical administration to a patient of an effective dose of a compound according to claim 1.

8. The compound of claim 1 which is [11β

,16α

(R,S)]-16,17-[cyclohexylmethylene)bis (oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione.

9. The R-epimer of the compound of claim 8.

10. The S-epimer of the compound of claim 8.

11. A compound of claim 1 wherein each of is X₁ and X₂ is hydrogen.

12. A compound of claim 1 wherein each of X₁ and X₂ is fluorine.