WO1998052556A1 - Glucosamine fatty acid compositions and their use - Google Patents
Glucosamine fatty acid compositions and their use Download PDFInfo
- Publication number
- WO1998052556A1 WO1998052556A1 PCT/GB1998/001425 GB9801425W WO9852556A1 WO 1998052556 A1 WO1998052556 A1 WO 1998052556A1 GB 9801425 W GB9801425 W GB 9801425W WO 9852556 A1 WO9852556 A1 WO 9852556A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- glucosamine
- fatty acid
- acid
- essential fatty
- octadeca
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
Definitions
- the invention relates to the presentation and use of sugar amines.
- N-methyl glucamine as an example of compounds broadly presented as N-alkyl polyhydroxy amines, is disclosed in the form of salts with polyunsaturated fatty acids.
- the fatty acids are particularly the "6-desaturated" n-6 and n-3 essential fatty acids i.e. those beyond the 6-desaturation stage in bodily conversion of dietary linoleic and ⁇ -linolenic acids, and may be as such or in the form of their esters or amides with a bifunctional compound also having a salt-forming acidic function. Examples of such compounds are ascorbic acid, when the fatty acid is as a 6-ester, and salicylic acid.
- the N-methyl glucamine salts are:-
- the purpose is to present the fatty acids in water soluble form for their numerous therapeutic and other actions, allowing for example ready absorption from the gut into the hepatic portal system, or intravenous administration.
- meglumine moiety lacking a carbonyl function, is only formally related to sugars and has no function other than as a carrier of the fatty acid.
- EFAs essential fatty acids
- the acids which in nature are of the all - cis configuration, are systematically named as derivatives of the corresponding octadecanoic, eicosanoic or docosanoic acids, e.g. z,z-octadeca - 9,12 - dienoic acid for LA or z,z,z,z,z,z - docosa- 4,7,10,13,16,19 - hexaenoic acid for DHA, but numerical designations based on the number of carbon atoms, the number of centres of unsaturation and the number of carbon atoms from the end of the chain to where the unsaturation begins, such as, correspondingly, 18:2 n-6 or 22:6 n-3, are convenient.
- Drug treatments are many, but while analgesics (e.g paracetamol and codeine) and non-steroidal anti-inflammatory drugs (NSAIDs) are much used for relief of pain associated with osteoarthritis, rheumatoid arthritis and back problems, the NSAIDs are limited by their side effects and there is some evidence that they may actually impair cartilage metabolism.
- Other pharmacological approaches include intra-articular steroid therapy, mechanical lubrication and chondroprotective agents including D-glucosamine sulphate, glycosaminoglycan-peptide complex and glycosaminoglycan polysulphate .
- GLA fatty acids
- ingestion of for example GLA elevates DGLA levels which results in an increase in production of anti-inflammatory 1 -series prostaglandins such as PGE1.
- Ingested EPA e.g. from fish oil
- the anti- inflammatory activity of both GLA and EPA in animal and human studies is well documented in prior patents of the applicants and in the general literature.
- the amino-monosaccharide glucosamine is found in the matrix of articular cartilage where it is a component of various glycosaminoglycans. Synthesis of glycosaminoglycans requires sulphate ions as well as glucosamine. In vitro studies have long demonstrated that glucosamine stimulates the uptake of radioactively labelled sulphate ions by chondrocytes as a result of glycosaminoglycan synthesis. More recent in vitro studies have supported the conclusion that glucosamine stimulates synthesis of glycosaminoglycan and proteoglycans in general in chondrocytes.
- glucosamine Additional properties include protection of articular cartilage from damage caused by some non-steroidal anti-inflammatory drugs as well as anti-inflammatory activity in models of acute and sub-acute inflammation not caused by inhibition of prostaglandin synthesis. Also, several clinical trials have demonstrated the efficacy of glucosamine in the control of symptoms of osteoarthritis. It has been concluded that oral glucosamine is as effective as a standard NSAID such as ibuprofen, in controlling symptoms with clinically evident signs of inflammation, while it is significantly better tolerated.
- NSAID such as ibuprofen
- the invention concentrates on glucosamine as a natural cartilage constituent and in chemical terms provides:
- novel compositions of glucosamine and essential fatty acids especially the delta-6-desaturated n-6 and n-3 essential fatty acids such as GLA and EPA.
- the fatty acids may be used in natural form e.g. as evening primrose oil, fish oil, fungal oil, algal oil or other assimilable forms, or alternatively they may for example be present as salts of the glucosamine itself.
- the invention provides amide, ester or amide/ester derivatives of glucosamine wherein one or more of the amino and hydroxy functions carries a fatty acyl group derived from an n-6 or n-3 essential fatty acid, the fatty acid being linked to the amine or hydroxy function either directly or through a linking compound itself having a carboxylic acid function and in the latter case being replaceable by a corresponding fatty alcohol group esterified to a second carboxylic acid function of the linking compound.
- Such a structure may be as set out below: -
- R 1 to R 5 are independently H or a UFA-C • or UFA'-C/ group the same or different (but not all H) with the further possibility (when at least one of R 1 , R 3 , R 4 and R is such a group) that R is a to C 4 acyl group or other biocompatible derivatising function;
- UFA is the carbon chain of an n-6 or n-3 preferably 6-desaturated essential fatty acid, and very preferably a fatty acid with anti-inflammatory activity such as GLA,
- UFA 1 is the carbon chain of such a fatty acid, or of a corresponding fatty alcohol, covalently linked to a biocompatible bifunctional compound also having a free acidic group;
- the compound may be in the form of the free base or as a salt with a pharmaceutically acceptable acid
- the invention lies in application of compounds or compositions as above in the therapeutic or prophylactic treatment of disease or deterioration in bodily cartilaginous tissue.
- the cartilaginous tissue may in particular be that of the joints including those of the vertebral column and the invention is particularly applicable in inflammatory joint conditions including osteoarthritis, other forms of arthritis and conditions leading to back pain.
- the amounts of the fatty acids for daily administration are 10 mg to 10 g preferably 100 mg to 5 g and very preferably 300 mg to 3g and of the sugar amines 10 mg to 20 g, preferably 100 mg to 5 g and very preferably 300 mg to 3 g, preferably in corresponding molar amounts to the fatty acid where the two are not chemically combined.
- the compounds may be applied by oral, enteral, parenteral or topical routes.
- the compounds may be used directly in liquid form, or be formulated as emulsions, powders, tablets, or hard or soft gelatin capsules or in any other appropriate form known to those skilled in the art.
- Example 2 In a similar manner to Example 1 but replacing z,z,z-octadeca-6,9,12-trienoyl chloride with z,z,z,z,z-eicosa-5,8,l l,14,17-pentaenoic acid was prepared N-(z,z,z,z,z-eicosa-5, 8, 11,14,17- pentaenoyl)-D-glucosamide as an off-white amorphous solid.
- Examples 1 and 2 may be used without further purification in preparations for the purposes referred to herein, for example the treatment of osteoarthritis:-
- Oral pharmaceutical preparations containing 100 mg to 1 g, in 5 ml, of the product.
- Soft gelatin capsules conventional in themselves contain:- 295 mg evening primrose oil (8% GLA)
- Part 1 preparation of l-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
- Part 2 preparation of butanedioic acid, monoester with l-(z,z,z-octadeca-6,9,12- trienoyloxy)-3 -hydroxypropane
- Oxalyl chloride (3.9ml) was added to a solution of butanedioic acid, monoester with l-(z,z,z- octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (13g) in methylene chloride (75ml). The mixture was stirred at room temperature under nitrogen for 2h and concentrated to dryness. Hexane (75ml) was added and the mixture concentrated to dryness. This process was repeated with two further portions of hexane to yield l-(3-(z,z,z-octadeca-6,9,12-trienoyloxy) propyl)oxycarbonyl-4-butanoyl chloride as a pale yellow oil.
- Part 4 preparation of l-(3-(z,z,z-octadeca-6,9,12-trienoyloxy)propyl)oxycarbonyl-4-butanoic acid, N-hydroxysuccinimide ester
- Example 5 In a similar manner to Example 5 but replacing l-(z,z,z-octadeca-6,9,12-trienoyloxy)-3- hydroxypropane in Part 2 with z,z,z-octadeca-6,9,12-trienol (prepared by reduction of z,z,z- octadeca-6,9,12-trienoic acid) was prepared l-(z,z,z-octadeca-6,9,12- trienyloxycarbonyl)-4- butanoyl-D-glucosamide as an off-white amorphous solid.
- z,z,z-Octadeca-6,9,12-trienoic acid (2.78g) is added dropwise with stirring under nitrogen to a solution of D-glucosamine (1.79g) in water (50 ml). Stirring is continued at room temperature until a clear solution results. Lyophilisation yields glucosammonium z,z,z- octadeca-6,9, 12-trienoate.
- Examples 5 to 7 may be used in the manner of Examples 3 and 4.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98921639A EP0977561A1 (en) | 1997-05-20 | 1998-05-18 | Glucosamine fatty acid compositions and their use |
CA002290488A CA2290488A1 (en) | 1997-05-20 | 1998-05-18 | Glucosamine fatty acid compositions and their use |
AU74423/98A AU7442398A (en) | 1997-05-20 | 1998-05-18 | Glucosamine fatty acid compositions and their use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9710351.9 | 1997-05-20 | ||
GBGB9710351.9A GB9710351D0 (en) | 1997-05-20 | 1997-05-20 | Glucosamine fatty acids |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998052556A1 true WO1998052556A1 (en) | 1998-11-26 |
Family
ID=10812725
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1998/001425 WO1998052556A1 (en) | 1997-05-20 | 1998-05-18 | Glucosamine fatty acid compositions and their use |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0977561A1 (en) |
AU (1) | AU7442398A (en) |
CA (1) | CA2290488A1 (en) |
GB (1) | GB9710351D0 (en) |
WO (1) | WO1998052556A1 (en) |
ZA (1) | ZA984211B (en) |
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EP0977561A1 (en) | 2000-02-09 |
CA2290488A1 (en) | 1998-11-26 |
ZA984211B (en) | 1998-11-20 |
AU7442398A (en) | 1998-12-11 |
GB9710351D0 (en) | 1997-07-16 |
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