Prednisolone derivatives

• US 5,733,901 A
• Filed: 09/29/1995
• Issued: 03/31/1998
• Est. Priority Date: 04/02/1993
• Status: Expired due to Term

• Current Assignee: Takeda GmbH (Takeda Pharmaceutical Company Limited)
• Original Assignee: BYK Gulden Lomberg Chemische Fabrik GMBH (Takeda Pharmaceutical Company Limited)
• Inventors: Gutterer, Beate
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): Sripada, Pavanaram K.
• Application Number:
  US08/530,173
• Time in Patent Office: 914 Days
• Field of Search: 540/63, 514/174
• US Class Current: 514/174
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/04 Antipruritics
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• 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: C07J 71/0005 Oxygen-containing hetero ring
• CPC Class Codes: C07J 71/0031 at positions 16, 17

Abstract

Epimers of the compound having the formula (I) are disclosed, both in their pure form and mixed in any desire mix ratio. ##STR1##

Claims

1. The compound of the formula I ##STR2## having the chemical name 16α

, 17-(22R, S)-cyclohexylmethyl-enedioxy-11β

, 21-dihydroxypregna-1,4-diene -3,20-dione.

4. A compound of formula I as claimed in claim 1, wherein the compound I is an epimer mixture of compounds Ia ##STR5## and Ib ##STR6## in any desired mixture ratio.

5. A process for the preparation of compound of formula I as claimed in claim 1, which comprises reacting 16-hydroxyprednisolone with cyclohexanecarboxaldehyde.

6. A pharmaceutical composition containing a suitable pharmaceutical auxiliary and a compound of formula I as claimed in claim 4 as an epimer mixture of the compounds Ia and Ib in any desired mixture ratio.

9. A method for treating of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, which comprises administering an effective amount of the compound of claim 1 to a subject so affiliated.

12. A method for treating of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, which comprises administering an effective amount of a compound of claim 4 to a subject so afflicted.

13. A method for producing a pharmaceutical composition with an effective amount of an active ingredient for the treatment of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, the improvement wherein the active ingredient is the compound of claim 1.

16. A method for producing a pharmaceutical composition with an active ingredient for the treatment of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, the improvement wherein the active ingredient is a compound of claim 4.

2. The compound of the formula Ia. ##STR3## having the chemical name 16β

,17-(22R)-cyclohexyl-methylenedioxy-11β

,21-dihydroxypregna-1,4-diene -3,20-dione.

7. A pharmaceutical composition containing an inert carrier and the compound of formula Ia as claimed in claim 2.

10. A method for treating of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, which comprises administering an effective amount of the compound of claim 2 to a subject so afflicted.

14. A method for producing a pharmaceutical composition with an active ingredient for the treatment and/or prophylaxis of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, the improvement wherein the active ingredient is the compound of claim 2.

3. The compound of the formula Ib ##STR4## having the chemical name 16β

,17-(22S)-cyclohexyl-methylenedioxy-11β

,21-dihydroxypregna-1,4-diene -3,20-dione.

8. A pharmaceutical composition containing an inert carrier and the compound of formula Ib as claimed in claim 3.

11. A method for treating of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, which comprises administering an effective amount of the compound of claim 3 to a subject so afflicted.

15. A method for producing a pharmaceutical composition with an active ingredient for the treatment and/or prophylaxis of a disorder of the skin, a disorder of the respiratory tract, an inflammatory disorder of the bowel, or allergic rhinitis/conjunctivitis, the improvement wherein the active ingredient is the compound of claim 3.

17. In a method for treating a disease condition which is amenable to treatment by a steroidal antiinflammatory and which comprises administering an effective amount of active ingredient to a mammal so afflicted, the improvement wherein the active ingredient comprises a member selected from the group consisting of 16β

,17-(22R, S)-cyclohexylmethylenedioxy-11β

,21-dihydroxypregna-1,4-diene-3,20-dione, 16β

,17-(22R)-cyclohexylmethylenedioxy-11β

,21-dihydroxpregna-1,4-diene-3,20-dione, and 16,α

,17-(22S)-cyclohexyl-methylenedioxy-11β

,21-dihydroxypregna-1,4-diene-3,20-dione.