Chemical compounds

• US 4,470,981 A
• Filed: 12/20/1982
• Issued: 09/11/1984
• Est. Priority Date: 12/20/1982
• Status: Expired due to Term

• Current Assignee: Robert H. Hesse
• Original Assignee: Robert H. Hesse
• Inventors: Hesse, Robert H.
• Primary Examiner(s): Roberts, Elbert L.
• Application Number:
  US06/451,252
• Time in Patent Office: 631 Days
• Field of Search: 260/397.5, 260/397.2, 424/238
• US Class Current: 514/182
• CPC Class Codes: C07C 323/00 Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
• CPC Class Codes: C07J 31/006 not covered by C07J31/003
• CPC Class Codes: C07J 53/00 Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
• CPC Class Codes: C07J 9/00 Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Abstract

The invention provides a compound of formula I ##STR1## where R¹ represents hydrogen, lower alkanoyl or aryol, or tri-lower alkyl silyl, or a group R³ --O--CO-- (where R³ represents lower alkyl); R² represents hydrogen, hydroxyl or fluorine and X represents --S--, --SO--, --SO₂ --, --O--or --NR⁴ -- (where R⁴ represents hydrogen, lower alkyl or lower alkanoyl); the compounds are useful in the prophylaxis or management of cardiovascular disease through the regulation of serum cholesterol and a particularly useful compound is 23-thia-25-hydroxy-cholesterol.

Claims

1. A compound of formula I ##STR6## where R¹ represents hydrogen, lower alkanoyl or aryol, or tri-lower alkyl silyl, or a group R³ --O--CO-- (where R³ represents lower alkyl);

R² represents hydrogen, hydroxyl or fluorine and X repreesents --S--;

--SO--, --SO₂ --, --O-- or --NR⁴ -- (where R⁴ represents hydrogen, lower alkyl or lower alkanoyl).

2. A compound as claimed in claim 1 wherein X is either --S--, or --SO-- or --SO₂ --.

3. A compound as claimed in claim 1 wherein X is either --S--, or --SO--, or --SO₂ -- and R₂ is either hydrogen or hydroxyl.

4. A compound as claimed in claim 1 wherein X is --S--.

5. A compound as claimed in claim 1 wherein X is --S-- and R² is hydroxyl.

6. A composition comprising a compound of claim 1 in sufficient amount to lower serum cholesterol together with one or more inert and acceptable pharmaceutical excipients.

7. A method of lowering serum cholesterol comprising administration of a compound of claim 1 in an amount sufficient to accomplish said reduction together with any pharmaceutically acceptable vehicle or excipient.

8. A method for lowering serum cholesterol comprising administration of a compound of claim 1 at a dose of 0.02 to 20 mg/kg. together with a pharmaceutically acceptable vehicle or excipient.