ES2356925T3 - Moduladores de citocinas que usan glicéridos cíclicos de ácidos grasos poliinsaturados esenciales. - Google Patents
Moduladores de citocinas que usan glicéridos cíclicos de ácidos grasos poliinsaturados esenciales. Download PDFInfo
- Publication number
- ES2356925T3 ES2356925T3 ES06710000T ES06710000T ES2356925T3 ES 2356925 T3 ES2356925 T3 ES 2356925T3 ES 06710000 T ES06710000 T ES 06710000T ES 06710000 T ES06710000 T ES 06710000T ES 2356925 T3 ES2356925 T3 ES 2356925T3
- Authority
- ES
- Spain
- Prior art keywords
- compound according
- treatment
- compound
- multiple sclerosis
- tgf
- 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.)
- Active
Links
- 150000004665 fatty acids Chemical class 0.000 title description 6
- 235000014113 dietary fatty acids Nutrition 0.000 title description 5
- 239000000194 fatty acid Substances 0.000 title description 5
- 229930195729 fatty acid Natural products 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 102000004127 Cytokines Human genes 0.000 claims abstract description 28
- 108090000695 Cytokines Proteins 0.000 claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 claims abstract 2
- 238000011282 treatment Methods 0.000 claims description 34
- 229960004488 linolenic acid Drugs 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims description 16
- 201000006417 multiple sclerosis Diseases 0.000 claims description 14
- 230000004770 neurodegeneration Effects 0.000 claims description 14
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 208000016192 Demyelinating disease Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 7
- 230000005856 abnormality Effects 0.000 claims description 7
- 210000004369 blood Anatomy 0.000 claims description 7
- 239000008280 blood Substances 0.000 claims description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
- 230000001225 therapeutic effect Effects 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
- 206010012305 Demyelination Diseases 0.000 claims description 6
- 206010019196 Head injury Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 208000029078 coronary artery disease Diseases 0.000 claims description 6
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 210000000987 immune system Anatomy 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 230000001537 neural effect Effects 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 230000002335 preservative effect Effects 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 208000032843 Hemorrhage Diseases 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 102000003814 Interleukin-10 Human genes 0.000 claims description 3
- 108090000174 Interleukin-10 Proteins 0.000 claims description 3
- 102000003816 Interleukin-13 Human genes 0.000 claims description 3
- 108090000176 Interleukin-13 Proteins 0.000 claims description 3
- 102000004388 Interleukin-4 Human genes 0.000 claims description 3
- 108090000978 Interleukin-4 Proteins 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 229930003427 Vitamin E Natural products 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 230000002490 cerebral effect Effects 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 230000003831 deregulation Effects 0.000 claims description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 230000003955 neuronal function Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 208000013223 septicemia Diseases 0.000 claims description 3
- 235000019165 vitamin E Nutrition 0.000 claims description 3
- 229940046009 vitamin E Drugs 0.000 claims description 3
- 239000011709 vitamin E Substances 0.000 claims description 3
- 206010018985 Haemorrhage intracranial Diseases 0.000 claims description 2
- 208000008574 Intracranial Hemorrhages Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 230000006866 deterioration Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000002028 premature Effects 0.000 claims description 2
- 230000002269 spontaneous effect Effects 0.000 claims description 2
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims 2
- 206010063401 primary progressive multiple sclerosis Diseases 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 125000001924 fatty-acyl group Chemical group 0.000 abstract description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 abstract description 2
- 230000008482 dysregulation Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 14
- 235000021324 borage oil Nutrition 0.000 description 13
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 102000046299 Transforming Growth Factor beta1 Human genes 0.000 description 9
- 101800002279 Transforming growth factor beta-1 Proteins 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 201000002491 encephalomyelitis Diseases 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 210000000952 spleen Anatomy 0.000 description 6
- 238000002965 ELISA Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 210000001744 T-lymphocyte Anatomy 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 239000000902 placebo Substances 0.000 description 5
- 229940068196 placebo Drugs 0.000 description 5
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 235000004626 essential fatty acids Nutrition 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 230000002503 metabolic effect Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000000750 progressive effect Effects 0.000 description 4
- 230000000770 proinflammatory effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 108010062580 Concanavalin A Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 239000012980 RPMI-1640 medium Substances 0.000 description 3
- 102000009618 Transforming Growth Factors Human genes 0.000 description 3
- 108010009583 Transforming Growth Factors Proteins 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- -1 cyclic glycerols Chemical class 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 210000005087 mononuclear cell Anatomy 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- YEENEYXBHNNNGV-XEHWZWQGSA-M sodium;3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoate;(2r,3r,4s,5s,6r)-2-[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound [Na+].CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I.O[C@H]1[C@H](O)[C@@H](CO)O[C@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 YEENEYXBHNNNGV-XEHWZWQGSA-M 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- RCRCTBLIHCHWDZ-UHFFFAOYSA-N 2-Arachidonoyl Glycerol Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO RCRCTBLIHCHWDZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 108091058560 IL8 Proteins 0.000 description 2
- 206010062016 Immunosuppression Diseases 0.000 description 2
- 102000000743 Interleukin-5 Human genes 0.000 description 2
- 108010002616 Interleukin-5 Proteins 0.000 description 2
- 102000004889 Interleukin-6 Human genes 0.000 description 2
- 108090001005 Interleukin-6 Proteins 0.000 description 2
- 102000004890 Interleukin-8 Human genes 0.000 description 2
- 108090001007 Interleukin-8 Proteins 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000002591 computed tomography Methods 0.000 description 2
- 230000016396 cytokine production Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 2
- 235000008524 evening primrose extract Nutrition 0.000 description 2
- 239000010475 evening primrose oil Substances 0.000 description 2
- 229940089020 evening primrose oil Drugs 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 210000003918 fraction a Anatomy 0.000 description 2
- 229940074076 glycerol formal Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 229940040452 linolenate Drugs 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002595 magnetic resonance imaging Methods 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MRKXCQPDRPTZCG-IUQGRGSQSA-N (9e,12e,15e)-octadeca-9,12,15-trienoyl chloride Chemical compound CC\C=C\C\C=C\C\C=C\CCCCCCCC(Cl)=O MRKXCQPDRPTZCG-IUQGRGSQSA-N 0.000 description 1
- VCKSNYNNVSOWEE-UHFFFAOYSA-N 1,3-dioxan-5-ol Chemical compound OC1COCOC1 VCKSNYNNVSOWEE-UHFFFAOYSA-N 0.000 description 1
- MUJOYSWPCZMTCY-DOFZRALJSA-N 1,3-dioxan-5-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC1COCOC1 MUJOYSWPCZMTCY-DOFZRALJSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 description 1
- 210000003771 C cell Anatomy 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- 206010061819 Disease recurrence Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 102000008070 Interferon-gamma Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 238000000585 Mann–Whitney U test Methods 0.000 description 1
- 241001661345 Moesziomyces antarcticus Species 0.000 description 1
- 241000498617 Mucor javanicus Species 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- 102000002233 Myelin-Oligodendrocyte Glycoprotein Human genes 0.000 description 1
- 108010000123 Myelin-Oligodendrocyte Glycoprotein Proteins 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010067171 Regurgitation Diseases 0.000 description 1
- 241001486234 Sciota Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 102000019197 Superoxide Dismutase Human genes 0.000 description 1
- 108010012715 Superoxide dismutase Proteins 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 206010054094 Tumour necrosis Diseases 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000001197 anandamide transport Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000947 anti-immunosuppressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000002886 arachidonoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004097 arachidonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000002380 cytological effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002074 deregulated effect Effects 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000816 effect on animals Effects 0.000 description 1
- 230000002900 effect on cell Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 231100000502 fertility decrease Toxicity 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 229960003130 interferon gamma Drugs 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940040461 lipase Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010598 long-chain omega-6 fatty acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 231100000394 myelinotoxic Toxicity 0.000 description 1
- 230000000256 myelinotoxic effect Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000007991 neuronal integrity Effects 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000020192 tolerance induction in gut-associated lymphoid tissue Effects 0.000 description 1
- 229940099456 transforming growth factor beta 1 Drugs 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 238000011870 unpaired t-test Methods 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Psychology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0504362.5A GB0504362D0 (en) | 2005-03-02 | 2005-03-02 | Cytokine modulators |
| GB0504362 | 2005-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2356925T3 true ES2356925T3 (es) | 2011-04-14 |
Family
ID=34430537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06710000T Active ES2356925T3 (es) | 2005-03-02 | 2006-03-02 | Moduladores de citocinas que usan glicéridos cíclicos de ácidos grasos poliinsaturados esenciales. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US20090137660A1 (enExample) |
| EP (1) | EP1853254B1 (enExample) |
| JP (1) | JP2008531675A (enExample) |
| KR (1) | KR20070114307A (enExample) |
| CN (1) | CN101171003A (enExample) |
| AT (1) | ATE490768T1 (enExample) |
| AU (1) | AU2006219733A1 (enExample) |
| CA (1) | CA2598785A1 (enExample) |
| DE (1) | DE602006018710D1 (enExample) |
| DK (1) | DK1853254T3 (enExample) |
| ES (1) | ES2356925T3 (enExample) |
| GB (1) | GB0504362D0 (enExample) |
| PL (1) | PL1853254T3 (enExample) |
| PT (1) | PT1853254E (enExample) |
| WO (1) | WO2006092623A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2304094B2 (es) * | 2003-08-18 | 2010-10-14 | Btg International Limited | Tratamiento de dolencias neurodegenerativas. |
| GB0504362D0 (en) * | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
| TR201808471T4 (tr) | 2010-07-05 | 2018-07-23 | Beth Israel Deaconess Medical Ct Inc | Sn-2-monoaçilgliseroller ve lipid malabsorpsiyonu. |
Family Cites Families (130)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2077371A (en) | 1937-04-13 | Synthetic drx | ||
| US2617791A (en) | 1949-09-15 | 1952-11-11 | Trojan Powder Co | Recovery of valuable products from pentaerythritol mother liquor |
| US3082228A (en) | 1959-12-18 | 1963-03-19 | Escambia Chem Corp | Method for producing monoesters of polyunsaturated fatty acids |
| US3158541A (en) | 1959-12-18 | 1964-11-24 | Escambia Chem Corp | Product for reduction of blood cholesterol concentration |
| FR2003425A1 (fr) | 1968-03-07 | 1969-11-07 | Unilever Nv | Compositions grasses plastiques comestibles et procede pour les preparer |
| US3558656A (en) | 1968-04-19 | 1971-01-26 | Smith Kline French Lab | Glycerol trichloroethyl carbonate and derivatives |
| US3671563A (en) | 1968-04-19 | 1972-06-20 | Smith Kline French Lab | Glycerol 3-(2,2,2-trichloroethyl) carbonate |
| US3676472A (en) | 1969-07-28 | 1972-07-11 | American Home Prod | Certain linoleic and linolenic acid ester fractions of vegetable oils and derivatives thereof |
| US3748348A (en) | 1970-07-27 | 1973-07-24 | Lever Brothers Ltd | Directed-interesterified glyceridic oils having a high linoleic acid content and process for their production |
| US3671557A (en) | 1970-09-17 | 1972-06-20 | Smith Kline French Lab | 1,2-diacylglycerol 3-(2,2,2-trichloroethyl) carbonates |
| GB1370021A (en) | 1971-03-25 | 1974-10-09 | Unilever Ltd | Process for preparing usaturated carboxylic acids |
| US3855254A (en) | 1972-03-31 | 1974-12-17 | Lever Brothers Ltd | Interesterification process |
| GB1506563A (en) | 1974-04-25 | 1978-04-05 | Williams J | Immunosuppressive agents |
| US4058594A (en) | 1974-04-25 | 1977-11-15 | John Williams | Immuno-suppressive agents |
| US3988446A (en) | 1974-11-07 | 1976-10-26 | Abbott Laboratories | Glycerides with anti-inflammatory properties |
| US3972907A (en) | 1975-03-24 | 1976-08-03 | G. D. Searle & Co. | Anti-hyperlipidemic fatty acids and esters |
| US4048202A (en) | 1975-04-11 | 1977-09-13 | G. D. Searle & Co. | 3-O-Alkanoylglyceric acids |
| US4181670A (en) | 1978-12-11 | 1980-01-01 | G. D. Searle & Co. | Phenyl 5Z,8Z,11Z,14Z-eicosatetraenoate and congeners |
| DE3368377D1 (en) | 1982-04-16 | 1987-01-29 | Nestle Sa | Lipid composition for oral, enteral or parenteral feeding |
| US4701469A (en) | 1983-04-15 | 1987-10-20 | Roussel Uclaf | Triglycerides, process for therapeutical applications and compositions containing them |
| US4701468A (en) | 1983-04-15 | 1987-10-20 | Roussel-Uclaf | Oxidized triglycerides having therapeutic utility |
| US4607052A (en) | 1983-04-15 | 1986-08-19 | Roussel-Uclaf | Triglycerides, dietetic and therapeutical applications and compositions containing them |
| GB8404463D0 (en) | 1984-02-21 | 1984-03-28 | Efamol Ltd | Microbiological production of essential fatty acids |
| AT383130B (de) | 1984-05-15 | 1987-05-25 | Chemie Linz Ag | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
| US5077312A (en) | 1984-07-08 | 1991-12-31 | Oncogen | Biologically active lipids binding membrane receptors |
| GB2178752B (en) | 1985-07-12 | 1989-10-11 | Unilever Plc | Substitute milk fat |
| GB8524275D0 (en) | 1985-10-02 | 1985-11-06 | Efamol Ltd | Pharmaceutical & dietary compositions |
| US5151291A (en) | 1985-12-27 | 1992-09-29 | Nisshin Flour Milling Co., Ltd. | Glycerides of eicosapentaenoic acid, processes for preparing the same and oil and fat products containing the same |
| US5306730A (en) | 1986-02-03 | 1994-04-26 | Kabushiki Kaisha Yakult Honsha | Botulinum toxin neutralizer |
| US5227403A (en) | 1986-10-01 | 1993-07-13 | The Nisshin Oil Mills, Ltd. | Fats and oils having superior digestibility and absorptivity |
| US4867965A (en) | 1986-10-02 | 1989-09-19 | Revlon, Inc. | Fatty acid diesters |
| US4832975A (en) | 1987-09-29 | 1989-05-23 | The Procter & Gamble Company | Tailored triglycerides having improved autoignition characteristics |
| US5008126A (en) | 1989-06-27 | 1991-04-16 | Nabisco Brands, Inc. | Long chain diol diesters as low calorie fat mimetics |
| GB9026648D0 (en) | 1990-12-07 | 1991-01-23 | Efamol Holdings | Nutrition |
| US5922345A (en) | 1990-12-07 | 1999-07-13 | Scotia Holdings Plc | Nutrition |
| PH11992043811B1 (en) | 1991-01-24 | 2002-08-22 | Martek Corp | Arachidonic acid and methods for the production and use thereof |
| US5658767A (en) | 1991-01-24 | 1997-08-19 | Martek Corporation | Arachidonic acid and methods for the production and use thereof |
| US5674901A (en) | 1995-06-01 | 1997-10-07 | Wisconsin Alumni Research Foundation | Methods of treating animals to maintain or increase CD-4 and CD-8 cell populations |
| US5618955A (en) | 1992-11-30 | 1997-04-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Fatty acid derivatives and pharmaceutical compositions containing same |
| ES2136189T3 (es) | 1993-01-15 | 1999-11-16 | Abbott Lab | Lipidos estructurados. |
| GB9301446D0 (en) | 1993-01-26 | 1993-03-17 | Scotia Holdings Plc | Internal radiation damage |
| JPH06279311A (ja) | 1993-03-26 | 1994-10-04 | Sagami Chem Res Center | プロテインキナーゼcアイソザイムの活性化剤 |
| JPH0741421A (ja) | 1993-05-28 | 1995-02-10 | Suntory Ltd | ロイコトリエンb4 (ltb4 )による医学的症状の予防及び改善剤 |
| US20050027004A1 (en) | 1993-06-09 | 2005-02-03 | Martek Biosciences Corporation | Methods of treating senile dementia and Alzheimer's diseases using docosahexaenoic acid and arachidonic acid compositions |
| US5663450A (en) | 1993-08-17 | 1997-09-02 | Cv Therapeutics | Macrophage lipid chemoattractant |
| US5668174A (en) | 1993-12-29 | 1997-09-16 | Kowa Tekuno Sachi Co., Ltd. | Method of treating hyperparathyroidism |
| JPH07309773A (ja) | 1994-05-16 | 1995-11-28 | Sagami Chem Res Center | アセチルコリン放出促進剤 |
| FR2722410B1 (fr) | 1994-07-15 | 1996-10-04 | Grinda Jean Robert | Procede de stabilisation des acides gras poly-insatures et utilisation de ces produits stabilises entherapeutique |
| JP3770628B2 (ja) | 1994-08-09 | 2006-04-26 | サントリー株式会社 | 遅延型アレルギー反応を介する医学的症状の予防及び改善剤 |
| EP0707850A1 (en) | 1994-09-21 | 1996-04-24 | Scotia Holdings Plc | Use of polyunsaturated fatty acids for the manufacture of a medicament for the treatment of brest pain |
| EP0711503A3 (en) | 1994-11-14 | 1997-11-26 | Scotia Holdings Plc | Milk fortified with GLA and/or DGLA |
| US5990163A (en) | 1995-01-13 | 1999-11-23 | The Salk Institute For Biological Studies | Selective modulation of processes mediated by retinoid X receptors, and compounds useful therefor |
| DE19503993A1 (de) | 1995-02-08 | 1996-08-14 | Johann Friedrich Dr Med Desaga | Verwendung eines Produktes zur enteralen Versorgung mit Lebensmittelinhaltsstoffen oder Arzneimittelinhaltsstoffen |
| US6410078B1 (en) | 1995-04-28 | 2002-06-25 | Loders-Croklaan B.V. | Triglycerides, rich in polyunsaturated fatty acids |
| ES2232839T3 (es) | 1995-08-07 | 2005-06-01 | Suntory Limited | Uso de una composicion para prevenir o tratar enfermedades causadas por anormalidades en tejidos cartilaginosos. |
| GB9519661D0 (en) | 1995-09-27 | 1995-11-29 | Scotia Holdings Plc | Fatty acid treatment |
| US6015798A (en) | 1995-10-10 | 2000-01-18 | Colgate Palmolive Company | Method for reducing the damaging effects of radiation therapy on animal skin and mucosa |
| US5776913A (en) | 1995-10-10 | 1998-07-07 | Colgate Palmolive Company | Therapeutic diet for metabolic abnormalities found in animals with lymphoma |
| JP2000508645A (ja) | 1996-04-12 | 2000-07-11 | ペプテック リミテッド | ポリ不飽和脂肪酸を使用する免疫病の治療方法 |
| US5753702A (en) | 1996-05-22 | 1998-05-19 | University Of Vermont | Arachidonic acid metabolite, 16-hete |
| ES2203806T3 (es) | 1996-06-03 | 2004-04-16 | Croda International Plc | Compuestos y usos de los mismos. |
| US6340485B1 (en) | 1996-06-03 | 2002-01-22 | Croda International Plc | Compositions and uses thereof |
| WO1998000125A1 (en) | 1996-06-29 | 1998-01-08 | The Scottish Agricultural College | Improvement of male fertility with antioxidants and/or polyunsaturated fatty acids |
| GB9617847D0 (en) | 1996-08-27 | 1996-10-09 | Scotia Holdings Plc | Fatty acid treatment |
| PL190181B1 (pl) | 1996-10-11 | 2005-11-30 | Scarista Ltd | Zastosowanie oleju zawierającego kwas eikozapentaenowy (KEP) i/lub kwas stearydonowy (KS) oraz preparat farmaceutyczny zawierający olej |
| SK112399A3 (en) | 1997-02-21 | 2000-12-11 | Abbott Lab | Methods and compositions for reducing the incidence of necrotizing enterocolitis |
| US6080787A (en) | 1997-02-21 | 2000-06-27 | Abbott Laboratories | Methods for reducing the incidence of necrotizing enterocolitis |
| US6201022B1 (en) | 1997-03-27 | 2001-03-13 | Myorx, Inc. | Methods for treating neurotransmitter-mediated pain syndromes by topically administering an omega fatty acid |
| US6432684B1 (en) | 1997-04-11 | 2002-08-13 | Abbott Laboratories | Human desaturase gene and uses thereof |
| US6051754A (en) | 1997-04-11 | 2000-04-18 | Abbott Laboratories | Methods and compositions for synthesis of long chain poly-unsaturated fatty acids in plants |
| US5968809A (en) | 1997-04-11 | 1999-10-19 | Abbot Laboratories | Methods and compositions for synthesis of long chain poly-unsaturated fatty acids |
| US20020037876A1 (en) | 1998-06-25 | 2002-03-28 | Yissum Research Development Company Of Hebrew University Of Jerusalem | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
| FR2765482B1 (fr) | 1997-07-07 | 2000-12-08 | Oreal | Utilisation de l'acide y-linolenique pour prevenir le stress oxydatif |
| GB9715444D0 (en) | 1997-07-22 | 1997-09-24 | Scotia Holdings Plc | Therapeutic and dietary compositions |
| EP0919230A1 (en) | 1997-12-01 | 1999-06-02 | Societe Des Produits Nestle S.A. | NMIFA's as anti-inflammatory agents in superficial mammal tissues |
| US6369252B1 (en) | 1998-02-26 | 2002-04-09 | The University Of Georgia Research Foundation, Inc. | Structured lipids |
| IL138690A0 (en) | 1998-04-03 | 2001-10-31 | Yissum Res Dev Co | Synthetic endogenous cannabinoids, analogues and uses thereof |
| US6696584B2 (en) | 1998-05-04 | 2004-02-24 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| US6214372B1 (en) | 1998-05-04 | 2001-04-10 | Con Lin Co., Inc. | Method of using isomer enriched conjugated linoleic acid compositions |
| US7101914B2 (en) | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| WO1999064389A1 (en) | 1998-06-09 | 1999-12-16 | Alexandros Makriyannis | Inhibitors of the anandamide transporter as analgesic agents |
| ATE375712T1 (de) | 1998-08-04 | 2007-11-15 | Cargill Inc | Promotoren der fettsäure-desaturase aus pflanzen |
| KR100325581B1 (ko) | 1998-08-07 | 2002-08-24 | 오우택 | 아라키토닉산의리폭시게네이즈대사결과물질을함유하는진통제용조성물 |
| AU5561999A (en) | 1998-08-13 | 2000-03-06 | Wistar Institute, The | Methods for reducing atherosclerotic plaques |
| GB9901809D0 (en) | 1999-01-27 | 1999-03-17 | Scarista Limited | Highly purified ethgyl epa and other epa derivatives for psychiatric and neurological disorderes |
| DE10029562A1 (de) | 1999-06-24 | 2001-03-01 | Strathmann Ag & Co | Lipophile Brennesselextrakte, Verfahren zu deren Herstellung und ihre Verwendung |
| DE19930030B4 (de) | 1999-06-30 | 2004-02-19 | Meduna Arzneimittel Gmbh | CO-3-ungesättigte Fettsäuren enthaltende orale Darreichungsform |
| FR2797584B1 (fr) | 1999-08-16 | 2008-07-25 | Stephane Desjonqueres | Utilisation de lipides peroxydes dans le traitement ou la prevention des plaies et inflammations des muqueuses de la cavite buccale |
| JP3779505B2 (ja) | 1999-08-24 | 2006-05-31 | 花王株式会社 | 油脂組成物 |
| US6426367B1 (en) | 1999-09-09 | 2002-07-30 | Efa Sciences Llc | Methods for selectively occluding blood supplies to neoplasias |
| US6340705B1 (en) | 1999-09-10 | 2002-01-22 | Monsanto Technology, Llc | Use of α-linolenic acid metabolites for treatment or prevention of cancer |
| EP1088552B1 (en) | 1999-09-30 | 2006-04-19 | Loders Croklaan B.V. | Compositions containing pinolenic acid and its use a health component |
| GB9923738D0 (en) | 1999-10-07 | 1999-12-08 | Nestle Sa | Nutritional composition |
| US20010047036A1 (en) | 1999-12-17 | 2001-11-29 | Vanderhoof Jon A. | Composition for improving the proliferative response during adaptation of the gastrointestinal tract and use in short bowel syndrome |
| EG22407A (en) | 2000-02-17 | 2003-01-29 | Iams Company | Method for improving bone modeling and chondrocyte functioning in growing canines |
| US6361806B1 (en) | 2000-02-23 | 2002-03-26 | Michael P. Allen | Composition for and method of topical administration to effect changes in subcutaneous adipose tissue |
| EP1129711B1 (en) | 2000-02-24 | 2004-01-28 | Unilever N.V. | Pinolenic acid against diabetes |
| ATE277608T1 (de) * | 2000-06-23 | 2004-10-15 | Yissum Res Dev Co | 2-arachidonylglycerol, ein hemmer des tumor nekrose faktors -alfa und neuroprotektor des gehirns bei geschlossenen kopfverletzungen |
| GB0016045D0 (en) | 2000-06-29 | 2000-08-23 | Laxdale Limited | Therapeutic combinations of fatty acids |
| JP2002047176A (ja) | 2000-08-04 | 2002-02-12 | Idemitsu Technofine Co Ltd | IgE産生抑制剤 |
| US6664230B1 (en) | 2000-08-24 | 2003-12-16 | The Regents Of The University Of California | Orally administered peptides to ameliorate atherosclerosis |
| FR2815227B1 (fr) | 2000-10-17 | 2003-04-11 | Schwartz Laboratoires Robert | Composition anti-stress destinee a etre incorporee principalement a des vehicules nutritionnels |
| NO310176B1 (no) | 2000-11-13 | 2001-06-05 | Wadlund As | Sammensetning for hud som inneholder kitosan-konjugert CLA og kitosankonjugert vitamin A eller et <beta>-cyklodekstrin-konjugertvitamin A samt fremgangsmåte for fremstilling og anvendelse avdenne |
| US6528040B1 (en) | 2001-01-18 | 2003-03-04 | Maurine Pearson | EMU oil-based formulations for use as an analgesic, anesthetic and antipruritic |
| JP2004527501A (ja) | 2001-03-05 | 2004-09-09 | ピー. アーネスト,スティーヴン | 経腸処方 |
| ES2238568T3 (es) | 2001-05-30 | 2005-09-01 | Laxdale Limited | Uso del coenzima q (ubiquinona) y acido eicosapentaenoico (epa) para el tratamiento del linfoma no hodgkin y trastornos psiquiatricos o neurologicos. |
| JP2003048831A (ja) | 2001-08-02 | 2003-02-21 | Suntory Ltd | 脳機能の低下に起因する症状あるいは疾患の予防又は改善作用を有する組成物 |
| EP1285590A1 (en) | 2001-08-08 | 2003-02-26 | Société des Produits Nestlé S.A. | Lipid blends |
| AU784852B2 (en) | 2001-08-10 | 2006-07-06 | Mars, Incorporated | Canine support diet |
| US20030032674A1 (en) | 2001-08-13 | 2003-02-13 | Hwang Daniel H. | Use of unsaturated fatty acids to treat severe inflammatory diseases |
| NL1019368C2 (nl) | 2001-11-14 | 2003-05-20 | Nutricia Nv | Preparaat voor het verbeteren van receptorwerking. |
| US6677470B2 (en) | 2001-11-20 | 2004-01-13 | Natural Asa | Functional acylglycerides |
| ITMI20012732A1 (it) | 2001-12-20 | 2003-06-20 | Health Pharma S R L | Integratore alimentare per neuropatici |
| AUPS082102A0 (en) | 2002-03-01 | 2002-03-21 | Women's And Children's Hospital | Therapeutic properties of oils |
| BR0308290A (pt) | 2002-03-08 | 2005-01-11 | Monsanto Technology Llc | Tratamento e prevenção de distúrbios inflamatórios |
| US20040048926A1 (en) | 2002-03-15 | 2004-03-11 | Hoffman Dennis Robert | Use of docosahexaenoic acid and arachidonic acid to enhance the visual development of term infants breast-fed up to the age of six months |
| US20060094784A1 (en) | 2002-05-17 | 2006-05-04 | Masataka Kagawa | Tgf-alpha expression inhibitors |
| US7335481B2 (en) | 2002-07-24 | 2008-02-26 | Christer Owman | Methods of identifying compounds that affect a fatty acid cell-surface receptor |
| AU2003304108B2 (en) | 2002-10-30 | 2007-03-22 | Spherics, Inc. | Nanoparticulate bioactive agents |
| US7074418B2 (en) | 2002-11-18 | 2006-07-11 | Changaris David G | Conjugated fatty acid based emulsion and methods for preparing and using same |
| AU2003293020A1 (en) | 2002-11-26 | 2004-06-18 | George Washington University | Method and composition with conjugated linoleic acid esters |
| US6841573B2 (en) | 2002-11-27 | 2005-01-11 | Molecular Nutrition | Use of arachidonic acid as a method of increasing skeletal muscle mass |
| US20040209953A1 (en) | 2002-12-06 | 2004-10-21 | Wai Lee Theresa Siu-Ling | Glyceride compositions and methods of making and using same |
| US20040208939A1 (en) | 2003-04-18 | 2004-10-21 | Barry Sears | Novel dietary compositions to reduce inflammation |
| GB0311081D0 (en) * | 2003-05-14 | 2003-06-18 | Btg Internat Limted | Treatment of neurodegenerative conditions |
| CA2534711A1 (en) | 2003-08-01 | 2005-02-10 | Medarex, Inc. | Combination therapies for multiple sclerosis |
| ES2304094B2 (es) * | 2003-08-18 | 2010-10-14 | Btg International Limited | Tratamiento de dolencias neurodegenerativas. |
| GB2409644B (en) | 2003-12-31 | 2005-12-21 | Igennus Ltd | Formulation comprising eicosapentaenoic acid or an ester thereof and a triterpene or an ester thereof |
| GB0504362D0 (en) | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
-
2005
- 2005-03-02 GB GBGB0504362.5A patent/GB0504362D0/en not_active Ceased
-
2006
- 2006-03-02 PL PL06710000T patent/PL1853254T3/pl unknown
- 2006-03-02 JP JP2007557595A patent/JP2008531675A/ja active Pending
- 2006-03-02 WO PCT/GB2006/000779 patent/WO2006092623A1/en not_active Ceased
- 2006-03-02 AU AU2006219733A patent/AU2006219733A1/en not_active Abandoned
- 2006-03-02 KR KR1020077022547A patent/KR20070114307A/ko not_active Ceased
- 2006-03-02 AT AT06710000T patent/ATE490768T1/de active
- 2006-03-02 EP EP06710000A patent/EP1853254B1/en not_active Not-in-force
- 2006-03-02 PT PT06710000T patent/PT1853254E/pt unknown
- 2006-03-02 CA CA002598785A patent/CA2598785A1/en not_active Abandoned
- 2006-03-02 ES ES06710000T patent/ES2356925T3/es active Active
- 2006-03-02 CN CNA2006800149575A patent/CN101171003A/zh active Pending
- 2006-03-02 DK DK06710000.8T patent/DK1853254T3/da active
- 2006-03-02 US US11/885,254 patent/US20090137660A1/en not_active Abandoned
- 2006-03-02 DE DE602006018710T patent/DE602006018710D1/de active Active
-
2010
- 2010-07-02 US US12/801,937 patent/US8114903B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB0504362D0 (en) | 2005-04-06 |
| JP2008531675A (ja) | 2008-08-14 |
| PL1853254T3 (pl) | 2011-07-29 |
| HK1110227A1 (en) | 2008-07-11 |
| KR20070114307A (ko) | 2007-11-30 |
| EP1853254B1 (en) | 2010-12-08 |
| CA2598785A1 (en) | 2006-09-08 |
| PT1853254E (pt) | 2011-03-07 |
| AU2006219733A1 (en) | 2006-09-08 |
| ATE490768T1 (de) | 2010-12-15 |
| US20090137660A1 (en) | 2009-05-28 |
| US20100297196A1 (en) | 2010-11-25 |
| DK1853254T3 (da) | 2011-03-28 |
| WO2006092623A1 (en) | 2006-09-08 |
| EP1853254A1 (en) | 2007-11-14 |
| DE602006018710D1 (de) | 2011-01-20 |
| CN101171003A (zh) | 2008-04-30 |
| US8114903B2 (en) | 2012-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2304094B2 (es) | Tratamiento de dolencias neurodegenerativas. | |
| US8487001B2 (en) | Medium-chain length fatty acids, glycerides and analogues as neutrophil survival and activation factors | |
| AU2002308456A1 (en) | Medium-chain length fatty acids, glycerides and analogues as neutrophil survival and activation factors | |
| EP2459189A1 (en) | Fatty acids as anti-inflammatory agents | |
| ES2294914A1 (es) | Metodo de tratamiento para una enfermedad neurodegenerativa. | |
| ES2356925T3 (es) | Moduladores de citocinas que usan glicéridos cíclicos de ácidos grasos poliinsaturados esenciales. | |
| JP2007262050A (ja) | アディポネクチン産生増強剤 | |
| US20090023807A1 (en) | Treatment of Cytokine Dysregulation by Using Sn-2 Gamma-Linolenoyl, Gamma-Diho-Molinolenoyl or Arachidonoyl Patty Acid Glycerol Monoesters | |
| HK1110227B (en) | Cytokine modulators using cyclic glycerides of essential polyunsaturated fatty acids | |
| CN1867328B (zh) | 脂类甘油酯用于制备治疗神经变性状况的药物的应用 | |
| US20090036410A1 (en) | Structured Phospholipids | |
| AJSiASMASMAJSMMiAAAS et al. | Decanoyl chloride (Capric acid chloride) | |
| GB2442161A (en) | Treatment of neurodegenerative conditions | |
| GB2442164A (en) | Treatment of neurodegenerative conditions |