IE64039B1 - Derivatives of lysolecithin for the treatment of autoimmune diseases - Google Patents
Derivatives of lysolecithin for the treatment of autoimmune diseasesInfo
- Publication number
- IE64039B1 IE64039B1 IE198790A IE198790A IE64039B1 IE 64039 B1 IE64039 B1 IE 64039B1 IE 198790 A IE198790 A IE 198790A IE 198790 A IE198790 A IE 198790A IE 64039 B1 IE64039 B1 IE 64039B1
- Authority
- IE
- Ireland
- Prior art keywords
- och3
- hyac
- planck
- max
- treated
- Prior art date
Links
- 208000023275 Autoimmune disease Diseases 0.000 title abstract description 6
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical class CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 241001465754 Metazoa Species 0.000 claims description 48
- 102000016611 Proteoglycans Human genes 0.000 claims description 43
- 108010067787 Proteoglycans Proteins 0.000 claims description 43
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 36
- 239000000427 antigen Substances 0.000 claims description 23
- 102000036639 antigens Human genes 0.000 claims description 23
- 108091007433 antigens Proteins 0.000 claims description 23
- 241000699670 Mus sp. Species 0.000 claims description 21
- 210000002966 serum Anatomy 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 210000000845 cartilage Anatomy 0.000 claims description 17
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 12
- MHFRGQHAERHWKZ-HHHXNRCGSA-N (R)-edelfosine Chemical compound CCCCCCCCCCCCCCCCCCOC[C@@H](OC)COP([O-])(=O)OCC[N+](C)(C)C MHFRGQHAERHWKZ-HHHXNRCGSA-N 0.000 claims description 11
- 108010062580 Concanavalin A Proteins 0.000 claims description 11
- 210000004698 lymphocyte Anatomy 0.000 claims description 11
- 230000000638 stimulation Effects 0.000 claims description 11
- 241000283690 Bos taurus Species 0.000 claims description 10
- 238000002649 immunization Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 9
- 230000002917 arthritic effect Effects 0.000 claims description 7
- 210000001188 articular cartilage Anatomy 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 229940104230 thymidine Drugs 0.000 claims description 7
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 6
- 208000008558 Osteophyte Diseases 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 201000010934 exostosis Diseases 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000011725 BALB/c mouse Methods 0.000 claims 8
- 230000003053 immunization Effects 0.000 claims 4
- 238000003556 assay Methods 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000011149 active material Substances 0.000 abstract description 2
- 201000006417 multiple sclerosis Diseases 0.000 abstract description 2
- ZGYRTJADPPDDMY-UHFFFAOYSA-N titanium;tetrahydrate Chemical compound O.O.O.O.[Ti] ZGYRTJADPPDDMY-UHFFFAOYSA-N 0.000 abstract 1
- 206010003246 arthritis Diseases 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 26
- 230000035755 proliferation Effects 0.000 description 16
- 241000219061 Rheum Species 0.000 description 9
- 230000009471 action Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000010348 incorporation Methods 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 208000024891 symptom Diseases 0.000 description 7
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 6
- 244000309466 calf Species 0.000 description 6
- 229960005536 Alkyl-lysophospholipid Drugs 0.000 description 5
- 230000003286 arthritogenic effect Effects 0.000 description 5
- 229960001231 choline Drugs 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
- 239000008267 milk Substances 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 4
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 210000001503 joint Anatomy 0.000 description 4
- 230000000750 progressive effect Effects 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 210000004989 spleen cell Anatomy 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 3
- 102000011413 Chondroitinases and Chondroitin Lyases Human genes 0.000 description 3
- 108010023736 Chondroitinases and Chondroitin Lyases Proteins 0.000 description 3
- 239000012980 RPMI-1640 medium Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 208000007502 anemia Diseases 0.000 description 3
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012228 culture supernatant Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 3
- 230000016784 immunoglobulin production Effects 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 102000037716 Chondroitin-sulfate-ABC endolyases Human genes 0.000 description 2
- 108090000819 Chondroitin-sulfate-ABC endolyases Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 206010036030 Polyarthritis Diseases 0.000 description 2
- 230000001363 autoimmune Effects 0.000 description 2
- 238000010241 blood sampling Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 210000003414 extremity Anatomy 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003226 mitogen Substances 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 210000004988 splenocyte Anatomy 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- MHFRGQHAERHWKZ-UHFFFAOYSA-N 1-octadecyl-2-methylglycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCCOCC(OC)COP([O-])(=O)OCC[N+](C)(C)C MHFRGQHAERHWKZ-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
- 102000057234 Acyl transferases Human genes 0.000 description 1
- 108700016155 Acyl transferases Proteins 0.000 description 1
- 208000008822 Ankylosis Diseases 0.000 description 1
- 206010071155 Autoimmune arthritis Diseases 0.000 description 1
- 210000004366 CD4-positive T-lymphocyte Anatomy 0.000 description 1
- 210000001266 CD8-positive T-lymphocyte Anatomy 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010023198 Joint ankylosis Diseases 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 210000002798 bone marrow cell Anatomy 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 230000008355 cartilage degradation Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 230000002089 crippling effect Effects 0.000 description 1
- 230000037029 cross reaction Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000008348 humoral response Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006028 immune-suppresssive effect Effects 0.000 description 1
- 239000000568 immunological adjuvant Substances 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000018937 joint inflammation Diseases 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 235000020121 low-fat milk Nutrition 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- -1 n-octadecyl Chemical group 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 201000001474 proteinuria Diseases 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 210000000538 tail Anatomy 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
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
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- 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
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3918082A DE3918082A1 (de) | 1989-06-02 | 1989-06-02 | Mittel gegen autoimmunerkrankungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE901987L IE901987L (en) | 1990-12-02 |
| IE64039B1 true IE64039B1 (en) | 1995-06-28 |
Family
ID=6381972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE198790A IE64039B1 (en) | 1989-06-02 | 1990-06-01 | Derivatives of lysolecithin for the treatment of autoimmune diseases |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5266564A (enExample) |
| EP (1) | EP0474712B1 (enExample) |
| JP (1) | JP2977894B2 (enExample) |
| AT (1) | ATE94757T1 (enExample) |
| AU (1) | AU5670690A (enExample) |
| CA (1) | CA2056421C (enExample) |
| CS (1) | CS276439B6 (enExample) |
| DE (2) | DE3918082A1 (enExample) |
| DK (1) | DK0474712T3 (enExample) |
| ES (1) | ES2060173T3 (enExample) |
| GR (1) | GR1001195B (enExample) |
| IE (1) | IE64039B1 (enExample) |
| WO (1) | WO1990014829A1 (enExample) |
| ZA (1) | ZA904196B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3941009A1 (de) * | 1989-12-12 | 1991-06-13 | Medmark Pharma Gmbh | Eliminierung von aktivierten lymphozyten |
| HU230048B1 (hu) * | 1996-02-09 | 2015-06-29 | Abbvie Biotechnology Ltd | Humán TNFalfa-kötő antitestek alkalmazása |
| US6583127B1 (en) | 1998-12-21 | 2003-06-24 | Inkeysa. Sa | Use of etherlysophospholipids as antiinflammatory agents |
| SE9902155L (sv) * | 1999-06-09 | 2000-12-10 | Bjoern Rydevik | Serum antibodies |
| JP2002228764A (ja) * | 2001-02-02 | 2002-08-14 | Fuji Photo Film Co Ltd | 透光性シート体検出装置 |
| CA2668923C (en) * | 2006-11-10 | 2015-01-13 | Alphaptose Gmbh | Use of tri-substituted glycerol compounds for the treatment of radiation injuries |
| ES2382756T3 (es) | 2006-11-10 | 2012-06-13 | Alphaptose Gmbh | Forma de dosificación oral que comprende compuestos de glicerol trisustituido |
| US8324188B2 (en) | 2006-11-10 | 2012-12-04 | Vladimir Khazak | Combinations of ET-18-O-CH3and anti-cancer agents for the treatment of cancer |
| EP2120873B1 (en) * | 2006-12-20 | 2012-06-27 | Alphaptose Gmbh | Topical dosage form comprising tri-substituted glycerol compounds |
| US8697138B2 (en) | 2007-03-28 | 2014-04-15 | Aker Biomarine As | Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders |
| EP2144618B2 (en) * | 2007-03-28 | 2024-11-20 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
| WO2009027692A2 (en) * | 2007-08-29 | 2009-03-05 | Aker Biomarine Asa | A new method for making krill meal |
| US20100226977A1 (en) * | 2007-08-29 | 2010-09-09 | Aker Biomarine Asa | Low viscosity phospholipid compositions |
| US8372812B2 (en) * | 2009-02-26 | 2013-02-12 | Aker Biomarine Asa | Phospholipid and protein tablets |
| WO2013156630A1 (en) | 2012-04-20 | 2013-10-24 | Alphaptose Gmbh | S-enantiomer of a tri-substituted glycerol compound |
| AU2014203179C1 (en) | 2013-06-14 | 2017-05-04 | Aker Biomarine Antarctic As | Lipid extraction processes |
| GB201400431D0 (en) | 2014-01-10 | 2014-02-26 | Aker Biomarine As | Phospholipid compositions and their preparation |
| CN114304375A (zh) | 2015-02-11 | 2022-04-12 | 阿克海洋生物南极股份公司 | 脂质组合物 |
| PT3256003T (pt) | 2015-02-11 | 2023-02-15 | Aker Biomarine Antarctic As | Processo de extração de lipídios |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2009343C3 (de) * | 1970-02-27 | 1980-10-23 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | Verwendung von Lysolecithinen als immunologische Adjuvantien |
| DE2009342C3 (de) * | 1970-02-27 | 1980-12-18 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | Verwendung von Glycerin-alkyläther-(l)-phosphorsäure-(3)-monocholinestern |
| DE2619686C2 (de) * | 1976-05-04 | 1986-08-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Verwendung eines Lysolecithins zur Tumorbehandlung |
| CH670763A5 (enExample) * | 1985-08-02 | 1989-07-14 | Seuref Ag | |
| DE3530767A1 (de) * | 1985-08-28 | 1987-03-12 | Max Planck Gesellschaft | Mittel gegen multiple sklerose |
-
1989
- 1989-06-02 DE DE3918082A patent/DE3918082A1/de active Granted
-
1990
- 1990-05-29 GR GR900100406A patent/GR1001195B/el not_active IP Right Cessation
- 1990-05-31 JP JP2507957A patent/JP2977894B2/ja not_active Expired - Fee Related
- 1990-05-31 DE DE90908504T patent/DE59002863D1/de not_active Expired - Fee Related
- 1990-05-31 CA CA002056421A patent/CA2056421C/en not_active Expired - Fee Related
- 1990-05-31 AU AU56706/90A patent/AU5670690A/en not_active Abandoned
- 1990-05-31 AT AT90908504T patent/ATE94757T1/de not_active IP Right Cessation
- 1990-05-31 US US07/777,248 patent/US5266564A/en not_active Expired - Lifetime
- 1990-05-31 EP EP90908504A patent/EP0474712B1/de not_active Expired - Lifetime
- 1990-05-31 WO PCT/EP1990/000870 patent/WO1990014829A1/de not_active Ceased
- 1990-05-31 CS CS902689A patent/CS276439B6/cs not_active IP Right Cessation
- 1990-05-31 ES ES90908504T patent/ES2060173T3/es not_active Expired - Lifetime
- 1990-05-31 DK DK90908504.5T patent/DK0474712T3/da active
- 1990-06-01 ZA ZA904196A patent/ZA904196B/xx unknown
- 1990-06-01 IE IE198790A patent/IE64039B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE901987L (en) | 1990-12-02 |
| AU5670690A (en) | 1991-01-07 |
| ES2060173T3 (es) | 1994-11-16 |
| GR900100406A (en) | 1991-11-15 |
| US5266564A (en) | 1993-11-30 |
| CS276439B6 (en) | 1992-05-13 |
| ZA904196B (en) | 1991-03-27 |
| GR1001195B (el) | 1993-06-07 |
| CA2056421A1 (en) | 1990-12-03 |
| ATE94757T1 (de) | 1993-10-15 |
| CA2056421C (en) | 2000-10-10 |
| EP0474712A1 (de) | 1992-03-18 |
| DE3918082A1 (de) | 1991-01-24 |
| EP0474712B1 (de) | 1993-09-22 |
| DK0474712T3 (da) | 1993-11-29 |
| JP2977894B2 (ja) | 1999-11-15 |
| CS268990A3 (en) | 1992-01-15 |
| DE59002863D1 (de) | 1993-10-28 |
| JPH04507096A (ja) | 1992-12-10 |
| DE3918082C2 (enExample) | 1992-02-06 |
| WO1990014829A1 (de) | 1990-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |