Preparation process of biologically active silicon compounds in a concentrated form

• US 6,172,250 B1
• Filed: 07/16/1996
• Issued: 01/09/2001
• Est. Priority Date: 09/30/1994
• Status: Expired due to Term

• Current Assignee: Exsymol SAM
• Original Assignee: Exsymol SAM
• Inventors: Nicolay, Jean-Francois, Franco, Andre, Seguin, Marie-Christine, Gueyne, Jean
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/647,907
• Time in Patent Office: 1,638 Days
• Field of Search: 556/466, 556/408, 556/410, 556/407, 556/411, 556/409, 556/413, 556/460, 556/418, 556/461, 556/419, 556/426, 514/64, 514/844, 514/944, 424/401, 424/457, 424/78.03
• US Class Current: 556/407
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/14 for baldness or alopecia
• CPC Class Codes: A61P 25/04 Centrally acting analgesics, e.g. opioids
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 27/12 for cataracts
• 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 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/14 Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
• CPC Class Codes: C07F 7/0836 Compounds with one or more Si-OH or Si-O-metal linkage
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C07F 7/0874 Reactions involving a bond of the Si-O-Si linkage
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 7/1896 Compounds having one or more Si-O-acyl linkages

Abstract

A process for the preparation of biologically active silicon compounds by hydrolysis of a precursor which produces a compound which prevents the formation of polymers from the silicon hydrolyzed bonds.

Claims

1. A process for the preparation of a silyl biologically active compound, comprising hydrolyzing a precursor having the formula:

in which A, B, C, D and X indicate radicals different from OH, and the linkages of A, B, C, D with the Si atom are covalent bonds and 2 or 3 of these bonds are hydrolysable,

wherein the hydrolysis is carried out in an aqueous solvent and at least one compound obtained is a stabilizing compound which prevents the formation of polymers from the silicon hydrolyzed bonds.

2. Process according to claim 1 performed at neutral pH and in the absence of any chemical or enzymatic catalyst and in which the said precursor is added drop by drop into the aqueous solvent under stirring.

3. Process according to claim 1 in which the said solvent is selected from the group consisting of alcohols and water miscible organic solvents.

4. Process according to claim 1 comprising first solubilizing the precursor in an oily compound containing water, and then adding an alcohol or a glycol miscible with the said oily compound thereto.

5. Process according to claim 1 in which at least one of the said radicals A, B, C, D of said precursor is bound to the silicon atom by an oxygen atom.

6. Process according to claim 5, in which at least one the said radicals A, B, C, D bound to the silicon atom is an ester moiety.

7. Process according to claim 1 in which at least one of the said radicals A, B, C, D is a phenoxy group.

8. Process according to claim 1 in which a stabilizing compound obtained is selected from the group consisting of hydroxy carboxylic acids, hydroxylated or phenolic aminoacids, glycols, catechol, catecholamine, polyols, monosaccharides, phenolic acids and esterified derivatives thereof.

9. A composition comprising a silyl obtained by the process according to claim 1 in combination with a carrier therefor.

10. A composition according to claim 9 in which the said precursor is caproyldiethoxymethylsilane, and the said composition contains the silyl in an amount sufficient to provide a regenerating activity for the re-structuration of capillaries.

11. A composition according to claim 10 in which the carrier comprises an aqueous gel.

12. A composition according to claim 9 in which the said precursor is dimethyl-silyl-N-acetyl-cysteine, and the composition contains an anti-glycation amount of the silyl for the treatment of cataracts.

13. A composition according to claim 12 in which the carrier is an eye-drop.

14. A composition according to claim 9 in which the precursor is 2,2-ethoxy-n-octyl-oxobenzo-1,3-dioxa-2-silane, and the composition contains an anti-inflammatory, hydrating, regenerating activity for the cutaneous pathologies treatment effective amount of the silyl.

15. A composition according to claim 9 in which the said precursor is 2,2-dimethyl-4-oxobenzo-1,3-dioxa-2-silane or 2,2-ethoxymethyl-4-oxobenzo-1,3-dioxa-2-silane, and the composition contains an anti-inflammatory effective amount of the silyl.

16. A composition according to claim 15, in which the carrier is a gingival solution, gingival gel, toothpaste or chewing gum.

17. A composition according to claim 9 in which the said precursor is 2,3-dimethysilyloxy-N-(3-hydroxypropyl)-3,3-butanamide, and the composition contains a metabolic stimulating activity for the hair loss treatment effective amount of the silyl.

18. A composition according to claim 17 in which the carrier is a hair lotion.

19. A composition according to claim 9 in which the said precursor is a derivative of a silyl alpha-hydroxy-acid selected from the group consisting of dimethysilyl-2-oxo-octanoate, ethoxymethylsilyl-2-oxo-octanoate, and 2,2-ethoxymethyl-4-oxo-5-methyl-1,3-dioxa-2-cyclosilane, the carrier is a cosmetic carrier and the composition contains a regenerating activity effective amount of the silyl for anti-wrinkles treatment.

20. A composition according to claim 9 in which the said precursor is tri-ethoxy-methylsilyl-sorbitol, and the composition contains a normalizing activity effective amount of the silyl for dry skin treatment.

21. A composition according to claim 9 in which the said precursor is dimethyl-silyl-2,3,5,6-ascorbate, the carrier is a cosmetic carrier and the composition contains an anti-free radical activity for the skin protection effective amount of the silyl.