WO2003002125B1 - Combination of aminosugars and cysteine or cysteine derivatives - Google Patents
Combination of aminosugars and cysteine or cysteine derivativesInfo
- Publication number
- WO2003002125B1 WO2003002125B1 PCT/DK2002/000446 DK0200446W WO03002125B1 WO 2003002125 B1 WO2003002125 B1 WO 2003002125B1 DK 0200446 W DK0200446 W DK 0200446W WO 03002125 B1 WO03002125 B1 WO 03002125B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- aminosugar
- cysteine
- optionally substituted
- salt
- derivative
- 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.)
- Ceased
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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to chemical complexes consisting of cysteine or derivatives of cysteine and an aminosugar as well as pharmaceutical compositions and dietary supplements comprising such complexes. The invention further relates to the use of such compositions or complexes for the preparation of a medicament or a dietary supplement in the suppresion of hypersensitivity and inflammatory reactions such as rheumatic or dermatological disorders or to a method of treating such diseases by administering such compositions and complexes.
Claims
1. A chemical complex consisting of: i) one or more cysteine derivative(s) of Formula I or salt(s) thereof; and ii) one or more optionally substituted aminosugar(s) or salt(s) thereof.
SRS
RN( RN) w γRl o
I
wherein RN is independently selected from the group consisting of hydrogen, optionally substituted C--C8-alkyl, optionally substituted C2-Cι0-all<enyl, optionally substituted C2-Cι0- alkynyl, optionally substituted C3-C7-cycloalkyl, and optionally substituted Q-Cβ-acyl; R1 is selected from the group consisting of OR3, SR3, halogen and N(RN)RN; and Rs is selected from the group consisting of hydrogen, sulphate, optionally substituted C-.- C6-alkyl, optionally substituted C--C6-al enyl, optionally substituted C2-C6-alkynyl, optionally substituted C-.-C8-acyl, optionally substituted C3-C7-cycloalkyl, a cysteine derivative according to Formula I, and two or more cysteine derivative(s) of Formula I linked by S-S linkages.
2. The chemical complex according to claim 1, wherein said aminosugar is an aminosugar derivative of a monosaccharide.
3. The chemical complex according to claim 2, wherein said aminosugar derivative of a monosaccharide is selected from the group consisting of glucosamine, galactosamine, mannosamine, derivatives and salts thereof.
4. The chemical complex according to claim 1, wherein said aminosugar is an aminosugar derivative of an oligosaccharide.
5. The chemical complex according to claim 1, wherein said aminosugar is an aminosugar derivative of a polysaccharide.
6. The chemical complex according to claim 5, wherein said aminosugar derivative of a polysaccharide is selected from the group consisting of chitin, chitosan, carboxymethyl- chitosan, chondroitin sulfate, heparin, heparan sulfate, keratan sulfate and hyaluronic acid.
7. The chemical complex according to claim 3, wherein said aminosugar derivative is selected from the group consisting of glucosamine sulfate, glucosamine hydrochloride, N- acetylglucosamine, galactosamine sulfate, galactosamine hydrochloride, N- acetylgalactosamine, mannosamine sulfate, mannosamine hydrochloride or N- acetylmannosamine and salts thereof.
5 8. The chemical complex according to claim 3, wherein the aminosugar is glucosamine sulfate or a salt thereof.
9. The chemical complex according to any one of the preceding claims, wherein the cysteine derivative(s) of Formula I or salt(s) thereof is selected from the group consisting 10 of cysteine, Na-acetylcysteine, cystine, homocysteine, cysteine methylester, S-ethyl- cysteine, N,S-isobuturyl-cysteine, S-carboxymethyl-cysteine, S-ethyl-homocysteine, S- methyl-cysteine, Cysteine S-sulfate, N,S-diacetyl-cysteine methylester, N-acetyl-S- methylcysteine and salts thereof.
15 10. The chemical complex according to any one of the preceding claims, wherein the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof are present in a molar ratio of between about 1: 10000 to 10000: 1, preferably of about 1 : 1000 to 1000: 1, more preferably of about 1: 100 to 100: 1, even more preferably of about 1: 10 to 10: 1 or of about 1:5 to 5: 1, most
20 preferably of about 1:2 to 2: 1 or 1: 1.
11. The chemical complex according to any one of the preceding claims, wherein the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof are present in a mass ratio of between about
25 1: 10000 to 10000: 1 preferably of about 1: 1000 to 1000: 1, more preferably of about
1: 100 to 100: 1, even more preferably of about 1 : 10 to 10: 1 or of about 1:5 to 5: 1, most preferably of about 1:2 to 2: 1 or 1: 1.
12. A composition comprising
30 i) a chemical complex consisting/comprising of one or more cysteine derivative(s) of Formula I or salts thereof and one or more optionally substituted aminosugar or salts thereof,
I
wherein RN is independently selected from the group consisting of hydrogen, optionally 35 substituted Ci-Cs-alkyl, optionally substituted C2-C10-alkenyl, optionally substituted C2-Cι0- alkynyl, optionally substituted C3-C7-cycloal yl, and optionally substituted C!-C8-acyl; R1 is selected from the group consisting of OR3, SR3, halogen and N(RN)RN; and Rs is selected from the group consisting of hydrogen, sulphate, optionally substituted C-- C6-alkyl, optionally substituted C!-C6-aIkenyl, optionally substituted C2-C6-alkynyl, optionally substituted C--C8-acyl, optionally substituted C3-C7-cycloalkyl, a cysteine 5 derivative according to Formula I, and two or more cysteine derivative(s) of Formula I linked by S-S linkages; and
ii) one or more acceptable excipient(s) or carrier(s),
10 13. The composition according to claim 12, wherein said aminosugar is an aminosugar derivative of a monosaccharide.
14. The composition according to claim 13, wherein said aminosugar derivative of a monosaccharide is selected from the group consisting of glucosamine, galactosamine,
15 mannosamine, derivatives and salts thereof.
15. The composition according to claim 12, wherein said aminosugar is an aminosugar derivative of an oligosaccharide.
20 16. The composition according to claim 12, wherein said aminosugar is an aminosugar derivative of a polysaccharide.
17. The composition according to claim 16, wherein said aminosugar derivative of a polysaccharide is selected from the group consisting of chitin, chitosan, carboxymethyl-
25 chitosan, chondroitin sulfate, heparin, heparan sulfate, keratan sulfate and hyaluronic acid.
18. The composition according to claim 14, wherein said aminosugar derivative is selected from the group consisting glucosamine sulfate, glucosamine hydrochloride, N- acetylglucosamine, galactosamine sulfate, galactosamine hydrochloride, N-
30 acetylgalactosamine, mannosamine sulfate, mannosamine hydrochloride or N- acetyimannosamine and salts thereof.
19. The composition according to claim 14, wherein the aminosugar is a glucosamine sulfate or a salt thereof.
35
20. The composition according to any one of claims 12 to 19, wherein the cysteine derivative(s) of Formula I or salt(s) thereof is selected from the group consisting of cysteine, Na-acetylcysteine, cystine, homocysteine, cysteine methylester, S-ethyl-cysteine, N,S-isobuturyl-cysteine, S-carboxymethyl-cysteine, S-ethyl-homocysteine, S-methyl-
40 cysteine, Cysteine S-sulfate, N,S-diacetyl-cysteine methylester, N-acetyl-S- methylcysteine, glutathione and salts thereof.
21. The composition according to any one of claims 12 to 20, wherein the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof are present in a molar ratio of between about 1 : 10000 to 10000: 1, preferably of about 1: 1000 to 1000: 1, more preferably of about 1: 100 to 100: 1, even more preferably of about 1: 10 to 10: 1 or of about 1 : 5 to 5: 1, most preferably of about 1 :2 to 2: 1 or 1: 1. 5
22. The composition according to any one of claims 12 to 20, wherein the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof are present in a mass ratio of between about 1: 10000 to 10000: 1, preferably of about 1 : 1000 to 1000: 1, more preferably of about 1: 100 to 100: 1,
10 even more preferably of about 1: 10 to 10: 1 or of about 1:5 to 5: 1, most preferably of about 1:2 to 2: 1 or 1: 1.
23. The composition according to any one of claims 12 to 22, formulated as a pharmaceutical composition for oral, topical, transdermal, or parenteral administration.
15
24. The composition according to claim 23, formulated for oral or topical administration.
25. The composition according to claim 23, formulated for topical administration.
20 26. A composition comprising: i) as active therapeutic agent a combination of one or more cysteine derivative(s) of Formula I or salts thereof and one or more optionally substituted aminosugar or salts thereof,
I
25 wherein RN is independently selected from the group consisting of hydrogen, optionally substituted Cι-C8-alkyl, optionally substituted C2-Cι0-alkenyl, optionally substituted C2-C10- alkynyl, optionally substituted C3-C7-cycloalkyl, and optionally substituted CrC8-acyl; R1 is selected from the group consisting of OR3, SR3, halogen and N(RN)RN; and Rs is selected from the group consisting of hydrogen, sulphate, optionally substituted C--
30 C6-alkyl, optionally substituted Cr -alkenyl, optionally substituted C2-C6-alkynyl, optionally substituted Cι-C8-acyl, optionally substituted C3-C7-cycloalkyl, a cysteine derivative according to Formula I, and two or more cysteine derivative(s) of Formula I linked by S-S linkages; and
35 ii) one or more acceptable excipient(s) or carrier(s),
27. The composition according to claim 26, wherein said aminosugar is an aminosugar derivative of a monosaccharide.
5 28. The composition according to claim 27, wherein said aminosugar derivative of a monosaccharide is selected from the group consisting of glucosamine, galactosamine, mannosamine, derivatives and salts thereof.
29. The composition according to claim 26, wherein said aminosugar is an aminosugar 10 derivative of an oligosaccharide.
30. The composition according to claim 26, wherein said aminosugar is an aminosugar derivative of a polysaccharide.
15 31. The composition according to claim 30, wherein said aminosugar derivative of a polysaccharide is selected from the group consisting of chitin, chitosan, carboxymethyl- chitosan, chondroitin sulfate, heparin, heparan sulfate, keratan sulfate and hyaluronic acid.
32. The composition according to claim 28, wherein said aminosugar derivative is selected 20 from the group consisting glucosamine sulfate, glucosamine hydrochloride, N- acetylglucosamine, galactosamine sulfate, galactosamine hydrochloride, N- acetylgalactosamine, mannosamine sulfate, mannosamine hydrochloride or N- acetylmannosamine and salts thereof.
25 33. The composition according to claim 28, wherein the aminosugar is a glucosamine sulfate or a salt thereof.
34. The composition according to any one of claims 26 to 33, wherein the cysteine derivative(s) of Formula I or salt(s) thereof is selected from the group consisting of 30 cysteine, Na-acetylcysteine, cystine, homocysteine, cysteine methylester, S-ethyl-cysteine, N,S-isobuturyl-cysteine, S-carboxymethyl-cysteine, S-ethyl-homocysteine, S-methyl- cysteine, Cysteine S-sulfate, N,S-diacetyl-cysteine methylester, N-acetyl-S- methylcysteine, glutathione and salts thereof.
35 35. The composition according to any one of claims 26 to 34, wherein the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof are present in a molar ratio of between about 1: 10000 to 10000: 1, preferably of about 1: 1000 to 1000: 1, more preferably of about 1: 100 to 100: 1, even more preferably of about 1: 10 to 10: 1 or of about 1 :5 to 5: 1, most preferably of
40 about 1:2 to 2: 1 or 1: 1.
36. The composition according to to any one of claims 26 to 34, wherein the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof are present in a mass ratio of between about 1: 10000 to 10000: 1, preferably of about 1: 1000 to 1000: 1, more preferably of about 1: 100 to 100: 1, even more preferably of about 1: 10 to 10: 1 or of about 1: 5 to 5: 1, most preferably of about 1:2 to 2: 1 or 1: 1
5 37. The composition according to any one of claims 26 to 36, formulated as a pharmaceutical composition for oral, topical, transdermal, or parenteral administration.
38. The composition according to claim 37, formulated for oral or topical administration.
10 39. The composition according to claim 37, formulated for topical administration.
40. Use of a combination of a cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof for the preparation of a product for the suppression of hypersensitivity and/or suppression of inflammatory
15 reactions in a mammal.
41. The use according to claim 40, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of rheumatic disease.
20 42. The use according to claim 41, wherein the rheumatic disease is selected from the group consisting of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, Reiter's syndrome, psoriastic arthritis, gout, juvenile chronic arthritis, enteropathic synovitis, infective arthritis, soft tissue rheumatism and fibromyalgia.
25 43. The use according to claim 40, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for chondroprotection or repair of articular cartilage.
44. The use according to claim 40, wherein the suppression of hypersensitivity and/or 30 suppression of inflammatory reactions is/are for the treatment of a skin disease.
45. The use according to claim 44, wherein the skin disease is selected from the group consisting of atopic dermatitis, contact dermatitis, seborrhoeic dermatitis, pruritus, nodular prurigo (prurigo nodularis hyde), urticaria, acne, rosacea, alopecia, vitiligo and psoriasis.
35
46. The use according to claim 40, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of IgE mediated allergic reactions.
40 47. The use according to claim 46, wherein the suppression of hypersensitivity and/or inflammatory reactions is/are for the treatment of diseases and disorders selected from the group consisting of asthma, allergic rhinitis, allergic conjunctivitis and anaphylaxis.
48. The use according to claim 40, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of an autoimmune disease and/or a chronic inflammatory disease.
5 49. The use according to claim 48, the treatment of an autoimmune disease and/or a chronic inflammatory disease is for the treatment of diseases and disorders selected from the group consisting of diabetes, Crohn's disease, lupus erythematosus, Scleroderma, Sjόgren's syndrome, Graves' disease, Pernicious anemia, autoimmune hepatitis, pemphigus vulgaris, pemphigus foliaceus, bullous pemphigoid, yasthenia gravis and 10 rheumatoid arthritis.
50. The use according to any one of claims 40 to 49, wherein the product comprises a composition as defined in any one of claims 12 to 39 or a complex as defined in any one of claims 1 to 11.
15
51. The use according to any one of claims 40 to 49, wherein the combination of the cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof is a chemical complex as defined in any one of claims 1 to 11.
20
52. The use according to any one of claims 40 to 51, wherein the cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof are together comprised in a single formulation or are each individually comprised in separate formulations.
25
53. The use according to any one of claims 40 to 51, wherein the cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof are together comprised in a single formulation.
30 54. The use according to any one of claims 40 to 53, wherein the combination of the cysteine derivative of Formula I or salt(s) thereof and the one or more optionally substituted aminosugar(s) or salt(s) thereof is formulated for oral, topical, transdermal, or parenteral administration, or combinations thereof.
35 55. The use according to claim 54, wherein said combination is formulated for oral administration.
56. The use according to claim 54, wherein said combination is formulated for topical administration.
40
57. A method for suppression of hypersensitivity and suppression of inflammatory reactions in a mammal, comprising the administration to said mammal of an effective amount of a combination of a cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof, or a chemical complex comprising said combination.
58. The method according to claim 57, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of a rheumatic disease.
59. The method according to claim 58, wherein the rheumatic disease is selected from the group consisting of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, Reiter's syndrome, psoriastic arthritis, juvenile chronic arthritis, enteropathic synovitis, infective arthritis, soft tissue rheumatism and fibromyalgia.
60. The method according to claim 57, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for chondroprotection or repair of articular cartilage.
61. The method according to claim 57, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of a skin disease.
62. The method according to claim 62, wherein the skin disease is selected from the group consisting of atopic dermatitis, contact dermatitis, seborrhoeic dermatitis, pruritus, nodular prurigo (prurigo nodularis hyde), urticaria, acne, rosacea, alopecia, vitiligo and psoriasis.
63. The method according to claim 57, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of IgE mediated allergic reactions
64. The method according to claim 57, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of diseases and disorders selected from the group consisting of asthma, allergic rhinitis, allergic conjunctivitis and anaphylaxis.
65. The method according to claim 57, wherein the suppression of hypersensitivity and/or suppression of inflammatory reactions is/are for the treatment of an autoimmune disease and/or a chronic inflammatory disease.
66. The method according to claim 65, wherein the treatment of an autoimmune disease and/or a chronic inflammatory disease relates to diseases selected from the group consisting of diabetes, Crohn's disease, lupus erythematosus, Scleroderma, Sjδgren's syndrome, Graves' disease, Pernicious anemia, autoimmune hepatitis, pemphigus vulgaris, pemphigus foliaceus, bullous pemphigoid, Myasthenia gravis and rheumatoid arthritis.
67. The method according to claim 57, wherein said combination of a cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof is a composition as defined in any one of claims 12 to 39 or a chemical complex as defined in any one of claims 1 to 11.
68. The method according to claim 57, wherein the cysteine derivative of Formula I or
5 salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof are together comprised in a single formulation or are each individually comprised in separate formulations.
69. The method according to claim 68, wherein the separate formulations are administered 10 in a simultaneous or non-simultaneous manner.
70. The method according to claim 57, wherein the cysteine derivative of Formula I or salt(s) thereof and one or more optionally substituted aminosugar(s) or salt(s) thereof are together comprised in a single formulation.
15
71. The method according to claim 70, wherein the single formulation or separate formulations are administered by means of oral, topical, transdermal, or parenteral administration, or combinations thereof
20 72. The method according to claim 70, wherein the single formulation or separate formulations are administered by means of oral administration.
73. The method according to claim 70, wherein the single formulation or separate formulations are administered by means of topical administration. 25
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200101038 | 2001-06-29 | ||
| DKPA200101038 | 2001-06-29 | ||
| DKPA200101056 | 2001-07-04 | ||
| DKPA200101056 | 2001-07-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO2003002125A2 WO2003002125A2 (en) | 2003-01-09 |
| WO2003002125A3 WO2003002125A3 (en) | 2003-11-06 |
| WO2003002125B1 true WO2003002125B1 (en) | 2004-05-21 |
Family
ID=26069044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DK2002/000446 Ceased WO2003002125A2 (en) | 2001-06-29 | 2002-06-28 | Combination of aminosugars and cysteine or cysteine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2003002125A2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1232256C (en) * | 2003-03-27 | 2005-12-21 | 中国人民解放军第三军医大学 | Application of N-acetylglucosamine in The preparation of medicine for treating local injure or whole body syndrome due to self immune reaction |
| US20040247686A1 (en) * | 2003-04-04 | 2004-12-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions comprising epinastine for the treatment of skin diseases |
| DE10337638A1 (en) * | 2003-08-16 | 2005-03-24 | Kirschfeld, Kuno, Prof. Dr. | Method of treating prostatitis |
| US7638503B2 (en) * | 2004-05-26 | 2009-12-29 | California Institute Of Technology | Small molecule stimulators of neuronal growth |
| AU2007325972A1 (en) * | 2006-10-03 | 2008-06-05 | Galleon Pharmaceuticals, Inc. | S-nitrosothiol compounds and related derivatives |
| US8912149B1 (en) | 2007-11-28 | 2014-12-16 | California Institute Of Technology | Glycosaminoglycan mimetics |
| ES2325392B1 (en) * | 2007-12-28 | 2010-06-24 | Bioiberica, S.A. | COMPOSITION FOR THE TREATMENT OF ARTROSIS. |
| ITRM20080636A1 (en) | 2008-11-28 | 2010-05-29 | Univ Palermo | PROCEDURE FOR THE PRODUCTION OF FUNCTIONAL DERIVATIVES OF HYALURONIC ACID AND RELATIVE HYDROGELS. |
| CN102850412B (en) * | 2012-10-12 | 2015-07-22 | 江苏澳新生物工程有限公司 | Preparation method of D-glucosamine sulfate sodium chloride salt |
| US9770461B2 (en) | 2013-08-02 | 2017-09-26 | California Institute Of Technology | Tailored glycopolymers as anticoagulant heparin mimetics |
| US10227370B2 (en) | 2013-08-02 | 2019-03-12 | California Institute Of Technology | Heparan sulfate/heparin mimetics with anti-chemokine and anti-inflammatory activity |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1283892A (en) * | 1970-06-08 | 1972-08-02 | Irwin Irville Lubowe | Improvements in and relating to medicinal compositions for application to the skin and/or hair |
| US6294520B1 (en) * | 1989-03-27 | 2001-09-25 | Albert T. Naito | Material for passage through the blood-brain barrier |
| US5895652A (en) * | 1996-07-29 | 1999-04-20 | Longevity Institute International | Method of metabolic adjuvanation and cellular repair |
| EP1021177A4 (en) * | 1997-02-04 | 2002-05-15 | John V Kosbab | Compositions and methods for prevention and treatment of vascular degenerative diseases |
| WO1999055326A1 (en) * | 1998-04-30 | 1999-11-04 | Vit-Immune, L.C. | Method of treatment of glutathione deficient mammals |
| AU5334899A (en) * | 1998-08-04 | 2000-02-28 | Kosbab, John V. | Nutrient and therapeutic compositions for the treatment of cancer |
| US6231889B1 (en) * | 1998-09-21 | 2001-05-15 | Chronorx, Llc | Unit dosage forms for the treatment of herpes simplex |
| US6358539B1 (en) * | 1999-08-20 | 2002-03-19 | Howard Murad | Pharmaceutical compositions for reducing the appearance of cellulite |
| US6492429B1 (en) * | 2000-07-10 | 2002-12-10 | N.V. Nutricia | Composition for the treatment of osteoarthritis |
-
2002
- 2002-06-28 WO PCT/DK2002/000446 patent/WO2003002125A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003002125A3 (en) | 2003-11-06 |
| WO2003002125A2 (en) | 2003-01-09 |
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