Compounds and medical devices activated with solvophobic linkers

• US 10,632,207 B2
• Filed: 11/13/2015
• Issued: 04/28/2020
• Est. Priority Date: 02/21/2009
• Status: Active Grant

• Current Assignee: Sofradim Production
• Original Assignee: Sofradim Production
• Inventors: Ladet, Sebastien, Gravagna, Philippe
• Primary Examiner(s): Richter, Johann R
• Assistant Examiner(s): Alley, Genevieve S
• Application Number:
  US14/940,613
• Publication Number:
  US 20160067344A1
• Time in Patent Office: 1,628 Days
• CPC Class Codes: A61K 47/30 Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
• CPC Class Codes: A61K 47/542 Carboxylic acids, e.g. a fatty acid or an amino acid
• CPC Class Codes: A61K 47/549 Sugars, nucleosides, nucleotides or nucleic acids
• CPC Class Codes: A61K 47/61 the organic macromolecular compound being a polysaccharide or a derivative thereof
• CPC Class Codes: A61K 47/62 the modifying agent being a protein, peptide or polyamino acid
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/48 with macromolecular fillers
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 takes precedence
• CPC Class Codes: A61L 31/14 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: C08L 101/02 characterised by the presence of specified groups , e.g. terminal or pendant functional groups

Abstract

The present disclosure relates to compounds and medical devices activated with a solvophobic material functionalized with a first reactive member and methods of making such compounds and devices.

Claims

1. An activated compound consisting of:

a solvophilic material covalently bonded to a solvophobic material, wherein the solvophilic material is chitosan having a degree of acetylation from about 0 to about 30% and the solvophobic material is a fatty acid functionalized with a first click reactive member, the first click reactive member providing the activated compound with a site for future attachment of a bioactive agent via click chemistry.

2. The compound of claim 1, wherein the first click reactive member is an alkyne group.

3. The compound of claim 1, wherein the first click reactive member is an azide group.

4. The compound of claim 1, wherein the fatty acid is a saturated fatty acid selected from the group consisting of butanoic, pentanoic, hexanoic, octanoic, nonanoic, decanoic, dodecanoic, tetradecanoic, hexadecanoic, heptadecanoic, octadecanoic, eicosanoic, docosanoic, tetracosanoic, hexacosanoic, heptacosanoic, and octacosanoic acids.

5. A compound consisting of:

a solvophilic material covalently bonded to a solvophobic material, wherein the solvophilic material is chitosan having a degree of acetylation from about 0 to about 30% and the solvophobic material is a fatty acid, and

a bioactive agent covalently bonded to said solvophobic material via click chemistry.

6. The compound of claim 5, wherein the fatty acid is a saturated fatty acid selected from the group consisting of butanoic, pentanoic, hexanoic, octanoic, nonanoic, decanoic, dodecanoic, tetradecanoic, hexadecanoic, heptadecanoic, octadecanoic, eicosanoic, docosanoic, tetracosanoic, hexacosanoic, heptacosanoic, and octacosanoic acids.

7. The compound of claim 5, wherein the bioactive agent is a therapeutic agent.

8. The compound of claim 5, wherein the bioactive agent is a diagnostic agent.

9. A compound consisting of

a solvophilic material covalently bonded to a solvophobic material, wherein the solvophilic material is a hydrophilic peptide or drug containing a free amine and the solvophobic material is a fatty acid, and

a bioactive agent covalently bonded to said solvophobic material via click chemistry.

10. The compound of claim 9, wherein the fatty acid is a saturated fatty acid selected from the group consisting of butanoic, pentanoic, hexanoic, octanoic, nonanoic, decanoic, dodecanoic, tetradecanoic, hexadecanoic, heptadecanoic, octadecanoic, eicosanoic, docosanoic, tetracosanoic, hexacosanoic, heptacosanoic, and octacosanoic acids.

11. The compound of claim 9, wherein the hydrophilic peptide or drug is selected from the group consisting of oxytocin, vasopressin, adrenocorticotrophic hormone (ACTH), epidermal growth factor (EGF), transforming growth factor antagonists, prolactin, luliberin or luteinizing hormone releasing hormone (LH-RH), LH-RH agonists or antagonists, growth hormone, growth hormone releasing factor, insulin, somatostatin, bombesin antagonists, glucagon, interferon, gastrin, tetragastrin, pentagastrin, urogastrone, secretin, calcitonin, enkephalins, endorphins, angiotensins, renin, bradykinin, bacitracins, polymyzins, colistins, tyrocidin, gramicidines, and synthetic analogues and modifications and pharmaceutically-active fragments thereof.

12. The compound of claim 9, wherein the bioactive agent is a therapeutic agent.

13. The compound of claim 9, wherein the bioactive agent is a diagnostic agent.

14. A composition comprising:

a hydrophilic solvent matrix; and

a solvophilic material covalently bonded to a solvophobic material,

wherein the solvophilic material is chitosan having a degree of acetylation from about 0 to about 30% and the solvophobic material is a fatty acid functionalized with a first click reactive member, the first click reactive member providing the activated compound with a site for future attachment of a bioactive agent via click chemistry.