Water soluble compositions for bioactive lipophilic compounds

A technology of biological activity and composition, which is applied in the directions of drug combination, active ingredients of hydrocarbon compounds, active ingredients of hydroxyl compounds, etc., can solve the problems of simplicity and unbalanced stability of preparations in the scope of application

Inactive Publication Date: 2002-06-05
NAT RES COUNCIL OF CANADA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although prior art known various lipophilic compounds (such as coenzyme Q 10 ) solubility in aqueous media, but they are unbalanced in terms of convenience, scope of application, stability of formulations, etc.

Method used

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  • Water soluble compositions for bioactive lipophilic compounds
  • Water soluble compositions for bioactive lipophilic compounds
  • Water soluble compositions for bioactive lipophilic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] The numbers following the above abbreviations (eg PCS-600) indicate the average molecular weight of the polyoxyethylene portion of the compound. A number followed by a Me abbreviation (eg, PTS-750Me) indicates a methyl terminated polyoxyethylene moiety (methoxypolyoxyethylene). Examples 1 and 2 illustrate the method of the present invention for preparing solubilizers. Embodiment 1. Preparation of polyoxyethylene-sitosterol sebacate (PSS-600)

[0084] 0.83 g of b-sitosterol (Sigma Chem. Co., #S-5753 product, approximately 60%) was dissolved in 3 ml of anhydrous toluene at 40°C, followed by the addition of 1.33 mM triethylamine (TEA). To the b-sitosterol-TEA solution was then added (dropwise, with stirring, and under anhydrous conditions) 1.33 mM sebacoyl chloride dissolved in 2 ml of anhydrous toluene. When the reaction was carried out at room temperature for 10 min, 2 mMPEG-600 (polyethylene glycol, Sigma Chem. . Stirring of the reaction was continued at room temper...

Embodiment 2

[0085] To 1.33 mM sebacoyl chloride dissolved in 2 ml of anhydrous toluene was added (dropwise under anhydrous conditions while stirring) 1 mM a-tocopherol (Sigma Chem. Co., #P-3251 product) and 1.33 mM TEA 3ml of anhydrous toluene solution. The reaction was carried out at room temperature for 10 minutes, followed by the dropwise addition of 2 mM PEG-600 (polyethylene glycol, Sigma, P-3390) and 2.66 mM TEA dissolved in 3 ml of toluene. The reaction was continued to stir at a constant rate for 20 minutes at room temperature. The reaction mixture was extracted four times with 3 ml of a saturated solution of sodium chloride each time, and the toluene was evaporated under reduced pressure. The product was dissolved in 5 ml of water and co-evaporated with water under reduced pressure to further remove residual toluene. Lyophilization afforded the final waxy product (1.15 g).

Embodiment 3

[0086] Polyethylene glycol (average molecular weight 1000, Sigma Chem. Co., #P-3515 product) or Polyethylene glycol methyl ether (average molecular weight 750, Sigma Chem. Co., product #P-7018) was linked to a-tocopherol to obtain other solubilizers (Table 1). They were synthesized according to the method of Example 2, and their properties were confirmed by mass spectrometry using MALDI-TOF technology. Example 3 provides the molecular characterization of the synthetic solubilizer. Example 3. Molecular characteristics of the solubilizer obtained by MALDI-TOF mass spectrometry analysis

[0087] Solubilizer

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Abstract

A solubilizing agent of the formula €ƒ€ƒ€ƒ€ƒ€ƒ€ƒ€ƒ€ƒ X-OOC-(CH 2 ) n -COO-Y wherein X is a member selected from campesterol, sitosterol, ergosterol and stigmasterol; Y is a member selected from polyalcohol, polyether, polyanion, polycation, polyphosphoric acid, polyamine, polysaccharide, polyhydroxy compound and polylysine, and derivatives thereof; and n is an integer selected from 0 to 18. The solubilizing agent may be included in a water-soluble composition comprising a bioactive lipophilic compound and the solubilizing agent.

Description

field of invention [0001] The present invention relates to water-soluble compositions of biologically active lipophilic compounds, compounds useful in the preparation of the compositions, processes for the preparation of the compounds and compositions and the use of the compositions as therapeutic drugs and cosmetics. Background of the invention [0002] Many biologically active compounds are highly lipophilic (hydrophobic), that is to say they are soluble in lipids (oils) and some organic solvents, while being essentially insoluble or only slightly soluble in water. The lack of solubility of bioactive compounds in aqueous media is an important limiting factor for their therapeutic applications, making it difficult to effectively administer said compounds to patients. Lipophilic compounds have very low bioavailability, that is, low concentrations of said compounds in the systemic circulation, when administered in the form of oil solutions or certain types of aqueous and / or o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K8/00A61K8/06A61K8/11A61K8/30A61K8/33A61K8/35A61K8/55A61K47/22A61K8/58A61K8/63A61K8/64A61K8/67A61K8/72A61K8/86A61K8/99A61K9/00A61K9/02A61K9/06A61K9/08A61K9/10A61K9/14A61K9/16A61K9/20A61K9/48A61K31/01A61K31/015A61K31/045A61K31/047A61K31/05A61K31/07A61K31/085A61K31/122A61K31/355A61K31/357A61K31/56A61K31/575A61K31/7048A61K38/43A61K47/14A61K47/28A61K47/32A61K47/34A61K47/36A61K47/42A61K47/48A61P3/06A61P9/10A61P21/02A61P25/16A61P25/28A61P29/00A61P31/10A61P35/00A61P43/00A61Q17/00A61Q19/00A61Q19/08
CPCA61K8/678A61K8/63A61K31/015A61K9/0014Y10S514/96A61K47/32A61K2800/70A61K9/0019A61K31/355A61K8/355A61K31/045A61K31/7048A61Q19/007A61Q19/08A61K47/28A61K31/047A61K8/671A61K9/146A61K8/67A61K31/122A61K2800/57A61Q19/00A61K31/01A61K8/676A61Q17/00A61K8/86A61P21/02A61P25/00A61P25/16A61P25/28A61P29/00A61P31/10A61P35/00A61P3/06A61P39/00A61P43/00A61P9/00A61P9/10A61K47/14
Inventor H·波罗维-波罗斯基M·斯科尔斯卡-瓦尔克P·R·瓦尔克
Owner NAT RES COUNCIL OF CANADA
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