Vitamin D derivatives active on the vitamin D nuclear receptor, preparation and uses thereof

• US 8,198,263 B2
• Filed: 09/26/2006
• Issued: 06/12/2012
• Est. Priority Date: 09/28/2005
• Status: Expired due to Fees

• Current Assignee: Centre National De La Recherche Scientifique, Universite De Strasbourg (Financière Meeschaert SA), Inserm (institut national de la sant et de la recherche mdicale
• Original Assignee: Institut National De La Sante Et De La Recherche Medicale (Inserm) (Allianz Global Investors GmbH), Centre National De La Recherche Scientifique, Universite De Strasbourg (Financière Meeschaert SA), Universidad De Santiago De Compostela (Tecnocontrol Servicios SA)
• Inventors: Moras, Dino, Rodrigues, Luis Cezar, Rochel, Natacha, Wurtz, Jean-Marie, Mourino-Mosquera, Antonio
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US12/088,413
• Publication Number:
  US 20090131378A1
• Time in Patent Office: 2,086 Days
• Field of Search: 514/167, 549/502, 552/653
• US Class Current: 514/167
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/18 Antioxidants, e.g. antiradicals preparations for protection against sunlight A61Q17/00
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/08 for bone diseases, e.g. rachitism, Paget's disease
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• 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 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: C07D 307/12 Radicals substituted by oxygen atoms

Abstract

The invention relates to vitamin D derivatives and their uses, particularly in the pharmaceutical industry. The invention discloses compounds having different interesting biological properties, including vitamin D nuclear receptor (VDR) agonist activity, as well as therapeutics methods by administering said compounds, in particular for treating cancer, psoriasis, autoimmune diseases, osteodistrophy and osteoporosis. It further relates to pharmaceutical compositions comprising said compounds and methods for preparing the same.

Claims

1. A compound presenting the following formula (I):

2. The compound according to claim 1, wherein R₁ represents a group selected from H, halogen atom, CH₃, (CH₂)₃OH or O(CH₂)₃OH.

3. The compound according to claim 1, wherein R represents:

4. The compound according to claim 1, wherein m is 0 or 1.

5. The compound according to claims 1, wherein n is 0.

6. The compound according to claim 1, wherein R₂ and R₃, identical or different, represent a group selected from H, halogen atom and a C₁-C₄ branched or linear alkyl.

7. The compound according to claim 1, wherein R₄ and R₅, identical or different, represent a group selected from H, halogen atom and a C₁-C₄ linear or branched alkyl.

8. The compound according to claim 1, wherein said compound is the specific stereoisomer according to the following formula (IV):

9. The compound according to claim 8, wherein R represents

10. The compound according to claim 8, wherein R represents

11. A pharmaceutical composition comprising at least one compound according to claim 1 and a pharmaceutically acceptable support, optionally with another active agent.