CA2402421A1 - Clathrate complexes formed by hyaluronic acid derivatives and use thereof as pharmaceuticals - Google Patents

Clathrate complexes formed by hyaluronic acid derivatives and use thereof as pharmaceuticals Download PDF

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Publication number
CA2402421A1
CA2402421A1 CA002402421A CA2402421A CA2402421A1 CA 2402421 A1 CA2402421 A1 CA 2402421A1 CA 002402421 A CA002402421 A CA 002402421A CA 2402421 A CA2402421 A CA 2402421A CA 2402421 A1 CA2402421 A1 CA 2402421A1
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CA
Canada
Prior art keywords
hyaluronic acid
clathrate
cyclodextrin
acid derivative
active ingredient
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002402421A
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French (fr)
Other versions
CA2402421C (en
Inventor
Ladislav Soltes
Bohumil Steiner
Eva Machova
Grigorij Kogan
Slavomir Bystricky
Raniero Mendichi
Viktor Bauer
Mojmir Mach
Juraj Alfoeldi
Eva Stratilova
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fidia Farmaceutici SpA
SLOVAK ACADEMY OF SCIENCES INSTITUTE OF EXPERIMENTAL PHARMACOLOGY
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Individual
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Publication of CA2402421A1 publication Critical patent/CA2402421A1/en
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Publication of CA2402421C publication Critical patent/CA2402421C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates

Abstract

A clathrate formed by: a hyaluronic acid derivative (a), a hyaluronic acid derivative (b1) different from (a), and being able to form a clathrate with (a) and/or a component (b2) not containing a hyaluronic acid moiety but being able to form with (a) a clathrate and its use in the pharmaceutical field.

Claims (43)

1. A clathrate formed by the association of ~ a hyaluronic acid derivative (a) ~ a hyaluronic acid derivative different from (a) and able with (a) to form a clathrate, and/ or ~ a compound not having a hyaluronic acid moiety, but being able to form a clathrate with (a).
2. The clathrate according to claim 1 selected from the group consisting of:
~ clathrate (A), wherein component (a) is a hyaluronic acid derivative with a cyclodextrin, compound (b1 ) is a hyaluronic acid with amantadine, ~ clathrate (B), wherein component (a) is a hyaluronic acid with cyclodextrin and (b2) is a water-soluble natural, semisynthetic or synthetic polimer.
~ clathrate (C), wherein component (a) is hyaluronic acid with amantadine and component (b2) is a polymerised cyclodextrin
3. The clathrate according to claim 2 wherein said hyaluronic acid derivative with cyclodextrin is selected from the group consisting of that obtained by the direct esterification of the carboxylic groups of hyaluronic acid with a cyclodextrin, and that obtained by means of a spacer.
4. The clathrate according to claim 3, wherein said spacer is adipic acid dihydrazide.
5. The clathrate according to any one of claims 2-4, wherein the cyclodextrin is selected from the group consisting of: a-cyclodextrin, b-cyclodextrin, y-cyclodextrin, propyl-~3-cyclodextrin, sulfobutyl-b-cyclodextrin, amino or hydrazino-b-cyclodextrin.
6. The clathrate according to anyone of claims 1-5, wherein said hyaluronic acid derivatives have a degree of substitution of the carboxylic function comprised between 0.5 and 50%.
7. The clathrate according to claim 6 wherein said degree of substitution is comprised between 2 and 50%.
8. The clathrate according to claim 2 wherein the hyaluronic acid derivative with amantadine has a substitution degree comprised between 0.5 and 25%.
9. The clathrate according to claim 8 wherein said hyaluronic acid derivative has substitution degree comprised between 2 and 10%.
10.The clathrate according to anyone of claims 1-9, wherein the starting reactant hyaluronic acid is used having a molecular weight contained between 100 and 2000 kDa.
11.The clathrate according to claim 2, characterised in that it is the clathrate (A).
12. The clathrate according to claim 11, having a molecular weight comprised between 500 and 25000 kDa and the molar ratio of hyaluronic acid derivative with cyclodextrin to hyaluronic acid derivative with amantadine is comprised between 10:90 and 90:10.
13. The clathrate complex according to claim 12, having a molecular weight comprised between 2000 and 20000 kDa and a molar ratio comprised between 80:20 and 50:50.
14. The clathrate according to claim 2 selected from the clathrate (B) and wherein said natural polymers to be used as component (b2) are selected from the group consisting of collagen, coprecipitates of collagen and glycosaminoglycans, cellulose, polysaccharides, agarose, xanthane, gellan, alginic acid salts or esters thereof, polymannan, polyglycans, starch, natural gums.
15. The clathrate according to claim 14, wherein the semisynthetic polymers to be used as component (b2) in clathrate (B) are selected from the group consisting of collagen cross-linked with crosslinking agents, derivatives of cellulose, hyaluronic acid, chitin, chitosan, gellan, xanthane, pectin or pectic acid, polyglycans, polymannan, agar, agarose, natural gum, glycosaminoglycans.
16. The clathrate according to claim 14 wherein the synthetic polymers are selected from the group consisting of poloxamers.
17. The clathrate according to claim 17, wherein the poloxamer is a polyethyleglycol having a molecular weight of 2000 DA.
18. The clathrate according to claim 2, selected from clathrate (C) and the polymerised cyclodextrin is polymerised (3-cylodextrin having a molecular weight of 91200 Da.
19. A medicament comprising as the active ingredient the clathrate complex according to anyone of claims 1-18.
20. The medicament according to claim 19 further comprising a low-molecular-weight active ingredient.
21. The medicament according to claim 20 wherein said active ingredient is selected from the group consisting of nonsteroidal or steroidal anti-inflammatory drugs, antibiotics, antitumorals.
22. The medicament according to anyone of claims 20 and 21, wherein said active ingredient is piroxicam.
23. The medicament according to anyone of claims 20-22, containing in alternative or in addition to said active ingredient a biologically active substance and/or a cellular material.
24. The medicament according to claim 23, wherein said biologically active substance is selected from the group consisting of growth factors, cytokines.
25. The medicament according to claim 24, wherein said cellular material is selected from the group consisting of: osteocytes, chondrocytes, stem cells, and mesenchymal cells.
26. A hyaluronic acid derivative with cyclodextrin obtained by means of a spacer.
27. The hyaluronic acid derivative according to claim 26, wherein said spacer is adipic acid hydrazide.
28. A process for preparing the hyaluronic acid derivative according to claim comprising the following steps:
a) an initial hydrazide group (-CO-NH-NH-CO-) formation between adipic acid dihydrazide (NH2-NHCO(CH2)4CONH-NH2) and the carboxylic groups of pre-activated hyaluronic acid, and b) a reaction between the second hydrazide function (NH2-NHCO-) of the adipic acid dihydrazide derivative of hyaluronic acid coming from the step (a) with a pre-activated cyclodextrin.
29. The process according to claim 28, wherein step (a) is carried out in the presence of an aqueous buffer solution at pH 5.5 consisting of sodium 2(N-morpholino)-ethanesulfonate, and adipic acid dihydrazide is added to hyaluronic acid activated with 1-ethyl-3(3-dimethyl-aminopropyl)-carbodiimide.
30. The process according to anyone of claims 28 or 29, wherein step (b) is carried out by adding hyaluronic acid derivative with adipic acid di-hydrazide coming from step (a) to a water solution of cyclodextrin previously activated with 1-cyano-4-dimethyl-aminopyridinium tetrafluoborate in acetonitrile in the presence of triethylamine and the reaction is stopped by adding ethanolamine.
31. A hyaluronic acid derivative with amantadine.
32. A process for preparing the hyaluronic derivative according to claim 31 comprising formation of the amidic bond between pre-activated hyaluronic acid and amantadine in an aqueous solution in the presence of a buffer.
33. The process according to claim 32, wherein the amantadine activator is 1-ethyl-3(3-dimethyl-aminopropyl)-carbodiimide and the buffer is sodium 2(N-morpholino)-ethanesulfonate.
34. A pharmaceutical composition containing as the active ingredient a hyaluronic acid derivative according to anyone of claims 26 and 27 in combination with suitable excipients and/or diluents.
35. A pharmaceutical composition containing as the active ingredient a hyaluronic acid derivative according to claim 31 in combination with suitable excipients and/or diluents.
36. The pharmaceutical composition according to claim 34 or claim 35 suitable for the oral, parenteral and topical administration.
37. A topical or parenteral pharmaceutical composition containing as the active ingredient a hyaluronic acid derivative with cyclodextrin obtained by the direct esterification of hyaluronic acid with cyclodextrin, in combination with suitable excipients and/ or diluents.
38. The pharmaceutical composition according to claim 36 and 37, in the form of an injectable or intrarticular solution.
39. The medicament according to anyone of claims 19-25, characterised in that it is obtained by the association of two pharmaceutical compositions in the form of injectable solutions containing as the active ingredient respectively a hyaluronic acid derivative with a cyclodextrin and a hyaluronic acid derivative with amantadine thereby obtaining in situ the clathrate (B) according to claim 2.
40. The medicament according to.claim 39 further containing the active ingredient, the biologically active substance and/or the cellular material coupled to cyclodextrin.
41. A controlled release pharmaceutical composition containing as the vehicling agent a hyaluronic acid derivative with a cyclodextrin.
42. The controlled release pharmaceutical composition according to claim 41, containing an active ingredient or a biologically active substance in the treatment of disorders in the field of dermatology, ophthalmology, gynaecology, oncology, angiology, neurology, orthopaedics and rheumatology.
43. Contrast media containing radioactive substance in association with a hyaluronic acid derivative with a cyclodextrin.
CA002402421A 2000-03-10 2001-03-12 Clathrate complexes formed by hyaluronic acid derivatives and use thereof as pharmaceuticals Expired - Lifetime CA2402421C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SKPV358-2000 2000-03-10
SK358-2000A SK282717B6 (en) 2000-03-10 2000-03-10 Preparation method of ultrahigh molecular hyaluronans
PCT/EP2001/002722 WO2001066601A1 (en) 2000-03-10 2001-03-12 Clathrate complexes formed by hyaluronic acid derivatives and use thereof as pharmaceuticals

Publications (2)

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CA2402421A1 true CA2402421A1 (en) 2001-09-13
CA2402421C CA2402421C (en) 2009-12-22

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Country Status (13)

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US (1) US7563824B2 (en)
EP (1) EP1272530B1 (en)
JP (1) JP2003525980A (en)
AU (2) AU5218001A (en)
CA (1) CA2402421C (en)
CZ (1) CZ20023029A3 (en)
DE (1) DE60123225T2 (en)
ES (1) ES2272465T3 (en)
HU (1) HUP0300163A3 (en)
NO (1) NO330340B1 (en)
PL (1) PL204330B1 (en)
SK (1) SK282717B6 (en)
WO (1) WO2001066601A1 (en)

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Also Published As

Publication number Publication date
CA2402421C (en) 2009-12-22
AU2001252180B2 (en) 2005-06-30
PL204330B1 (en) 2010-01-29
EP1272530A1 (en) 2003-01-08
HUP0300163A2 (en) 2003-06-28
PL357557A1 (en) 2004-07-26
HUP0300163A3 (en) 2003-09-29
DE60123225D1 (en) 2006-11-02
SK282717B6 (en) 2002-11-06
SK3582000A3 (en) 2002-09-10
NO20024192L (en) 2002-09-03
CZ20023029A3 (en) 2003-04-16
AU5218001A (en) 2001-09-17
NO20024192D0 (en) 2002-09-03
JP2003525980A (en) 2003-09-02
US20040076680A1 (en) 2004-04-22
DE60123225T2 (en) 2007-09-20
US7563824B2 (en) 2009-07-21
NO330340B1 (en) 2011-03-28
WO2001066601A1 (en) 2001-09-13
EP1272530B1 (en) 2006-09-20
ES2272465T3 (en) 2007-05-01
WO2001066601A8 (en) 2002-01-03

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