CA2251780A1 - Methods of treating immunopathologies using polyunsaturated fatty acids - Google Patents
Methods of treating immunopathologies using polyunsaturated fatty acids Download PDFInfo
- Publication number
- CA2251780A1 CA2251780A1 CA002251780A CA2251780A CA2251780A1 CA 2251780 A1 CA2251780 A1 CA 2251780A1 CA 002251780 A CA002251780 A CA 002251780A CA 2251780 A CA2251780 A CA 2251780A CA 2251780 A1 CA2251780 A1 CA 2251780A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- polyunsaturated fatty
- oxa
- thia
- fatty acid
- 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.)
- Abandoned
Links
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 241000534944 Thia Species 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 34
- 238000006467 substitution reaction Methods 0.000 claims abstract description 28
- 150000001413 amino acids Chemical class 0.000 claims abstract description 19
- 210000001744 T-lymphocyte Anatomy 0.000 claims abstract description 16
- 230000001404 mediated effect Effects 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003937 drug carrier Substances 0.000 claims abstract description 7
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 22
- 235000021342 arachidonic acid Nutrition 0.000 claims description 19
- 229940114079 arachidonic acid Drugs 0.000 claims description 19
- 239000004471 Glycine Substances 0.000 claims description 18
- 235000001014 amino acid Nutrition 0.000 claims description 18
- -1 hydroxy, hydroperoxy, peroxy Chemical group 0.000 claims description 18
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 208000024891 symptom Diseases 0.000 claims description 11
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 235000003704 aspartic acid Nutrition 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 7
- 230000004060 metabolic process Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- WIOJZOOPDOZCLL-TZGPHXOASA-N (2S)-2-aminobutanedioic acid (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O WIOJZOOPDOZCLL-TZGPHXOASA-N 0.000 claims description 3
- SUHOKBYLJMPHSL-LXPGDDCISA-N CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.OC(=O)[C@@H](N)CC(O)=O Chemical compound CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.OC(=O)[C@@H](N)CC(O)=O SUHOKBYLJMPHSL-LXPGDDCISA-N 0.000 claims description 2
- XQQNVFLZTNKRHJ-UHFFFAOYSA-N NCC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O Chemical compound NCC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O.CCCC=CC(O)=O XQQNVFLZTNKRHJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 235000020665 omega-6 fatty acid Nutrition 0.000 claims description 2
- 241001367053 Autographa gamma Species 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 37
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 22
- 229930195729 fatty acid Natural products 0.000 abstract description 22
- 239000000194 fatty acid Substances 0.000 abstract description 22
- 150000004665 fatty acids Chemical class 0.000 abstract description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 58
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
- 229910052796 boron Inorganic materials 0.000 description 41
- 239000003921 oil Substances 0.000 description 37
- 235000019198 oils Nutrition 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000004128 high performance liquid chromatography Methods 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 239000000872 buffer Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Substances [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 14
- 229960004488 linolenic acid Drugs 0.000 description 14
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- 230000001684 chronic effect Effects 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 210000000440 neutrophil Anatomy 0.000 description 13
- 102000004127 Cytokines Human genes 0.000 description 12
- 108090000695 Cytokines Proteins 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- 102100040247 Tumor necrosis factor Human genes 0.000 description 12
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 12
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 102000009270 Tumour necrosis factor alpha Human genes 0.000 description 10
- 108050000101 Tumour necrosis factor alpha Proteins 0.000 description 10
- 239000012630 HPLC buffer Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- 206010061218 Inflammation Diseases 0.000 description 8
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- 230000004044 response Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 208000024908 graft versus host disease Diseases 0.000 description 7
- 210000004698 lymphocyte Anatomy 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical class OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 6
- 206010039085 Rhinitis allergic Diseases 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 201000010105 allergic rhinitis Diseases 0.000 description 6
- 239000000427 antigen Substances 0.000 description 6
- 102000036639 antigens Human genes 0.000 description 6
- 108091007433 antigens Proteins 0.000 description 6
- GVLZIMQSYQDAHB-QRPNPIFTSA-N ditert-butyl (2s)-2-aminobutanedioate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)C[C@H](N)C(=O)OC(C)(C)C GVLZIMQSYQDAHB-QRPNPIFTSA-N 0.000 description 6
- 229940079322 interferon Drugs 0.000 description 6
- 210000002540 macrophage Anatomy 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 208000011231 Crohn disease Diseases 0.000 description 5
- 208000009329 Graft vs Host Disease Diseases 0.000 description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 5
- 102000014150 Interferons Human genes 0.000 description 5
- 108010050904 Interferons Proteins 0.000 description 5
- 102000000589 Interleukin-1 Human genes 0.000 description 5
- 108010002352 Interleukin-1 Proteins 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 5
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 5
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 5
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 description 5
- 210000003743 erythrocyte Anatomy 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 5
- 230000035755 proliferation Effects 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OSWULUXZFOQIRU-UHFFFAOYSA-N tert-butyl 2-aminoacetate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CN OSWULUXZFOQIRU-UHFFFAOYSA-N 0.000 description 5
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 5
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 5
- 229930105110 Cyclosporin A Natural products 0.000 description 4
- 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 4
- 108010036949 Cyclosporine Proteins 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 102000000588 Interleukin-2 Human genes 0.000 description 4
- 108010002350 Interleukin-2 Proteins 0.000 description 4
- 102000008072 Lymphokines Human genes 0.000 description 4
- 108010074338 Lymphokines Proteins 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- 206010040070 Septic Shock Diseases 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 208000037976 chronic inflammation Diseases 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 4
- 229940090949 docosahexaenoic acid Drugs 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 210000003630 histaminocyte Anatomy 0.000 description 4
- 230000005934 immune activation Effects 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 150000002617 leukotrienes Chemical class 0.000 description 4
- 210000005087 mononuclear cell Anatomy 0.000 description 4
- HCZKYJDFEPMADG-UHFFFAOYSA-N nordihydroguaiaretic acid Chemical compound C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 3
- NYBCZSBDKXGAGM-DOFZRALJSA-N (5Z,8Z,11Z,14Z)-icosatetraen-1-ol Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCO NYBCZSBDKXGAGM-DOFZRALJSA-N 0.000 description 3
- QTOSTWOHKGGRSN-XVSDJDOKSA-N 2-aminoacetic acid (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid Chemical compound NCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O QTOSTWOHKGGRSN-XVSDJDOKSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- 206010006895 Cachexia Diseases 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 206010012442 Dermatitis contact Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000004889 Interleukin-6 Human genes 0.000 description 3
- 108090001005 Interleukin-6 Proteins 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 241000219061 Rheum Species 0.000 description 3
- 206010039710 Scleroderma Diseases 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 206010052779 Transplant rejections Diseases 0.000 description 3
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 description 3
- 206010047115 Vasculitis Diseases 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 201000009961 allergic asthma Diseases 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 230000001363 autoimmune Effects 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000006020 chronic inflammation Effects 0.000 description 3
- 229960001265 ciclosporin Drugs 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 239000003246 corticosteroid Substances 0.000 description 3
- 229960001334 corticosteroids Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 230000005713 exacerbation Effects 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 208000002551 irritable bowel syndrome Diseases 0.000 description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 206010033675 panniculitis Diseases 0.000 description 3
- 230000008506 pathogenesis Effects 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 208000005987 polymyositis Diseases 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- 230000005951 type IV hypersensitivity Effects 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- WFYSUQMCIPGKKK-YHTMAJSVSA-N (6e,9e,12e)-octadeca-6,9,12-trien-1-ol Chemical compound CCCCC\C=C\C\C=C\C\C=C\CCCCCO WFYSUQMCIPGKKK-YHTMAJSVSA-N 0.000 description 2
- IKYKEVDKGZYRMQ-PDBXOOCHSA-N (9Z,12Z,15Z)-octadecatrien-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCO IKYKEVDKGZYRMQ-PDBXOOCHSA-N 0.000 description 2
- VXGCKRNAUZOFHA-UHFFFAOYSA-N 2-octadeca-6,9,12-trienoxyacetic acid Chemical compound CCCCCC=CCC=CCC=CCCCCCOCC(O)=O VXGCKRNAUZOFHA-UHFFFAOYSA-N 0.000 description 2
- LIYCOTUUWOESJK-OIZRIKEUSA-N 9-HPETE Chemical compound CCCCC\C=C/C\C=C/CC(OO)\C=C\C=C/CCCC(O)=O LIYCOTUUWOESJK-OIZRIKEUSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WZSFTPRZLZBEJZ-UHFFFAOYSA-N C(C)(=O)OOCCCCCC=C/CC=CCC=CCCCCC Chemical compound C(C)(=O)OOCCCCCC=C/CC=CCC=CCCCCC WZSFTPRZLZBEJZ-UHFFFAOYSA-N 0.000 description 2
- 208000016192 Demyelinating disease Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 206010056872 Palpable purpura Diseases 0.000 description 2
- 201000009594 Systemic Scleroderma Diseases 0.000 description 2
- 206010042953 Systemic sclerosis Diseases 0.000 description 2
- 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 2
- 206010044248 Toxic shock syndrome Diseases 0.000 description 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 2
- 206010045240 Type I hypersensitivity Diseases 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 208000002029 allergic contact dermatitis Diseases 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 208000010216 atopic IgE responsiveness Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 230000005784 autoimmunity Effects 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 2
- 229960002170 azathioprine Drugs 0.000 description 2
- 210000003651 basophil Anatomy 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000016396 cytokine production Effects 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 239000002254 cytotoxic agent Substances 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- KKQBNQXZNTVMBZ-UHFFFAOYSA-N docosa-1,3,5,7,9,11-hexaen-1-ol Chemical compound CCCCCCCCCCC=CC=CC=CC=CC=CC=CO KKQBNQXZNTVMBZ-UHFFFAOYSA-N 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 210000003979 eosinophil Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 2
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 2
- 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 2
- 229960002733 gamolenic acid Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000005534 hematocrit Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 239000012678 infectious agent Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229940100601 interleukin-6 Drugs 0.000 description 2
- 201000004792 malaria Diseases 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 238000007799 mixed lymphocyte reaction assay Methods 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- GSGNIYIJMYYXBX-UHFFFAOYSA-N octadeca-11,13,15,17-tetraen-4-yl ethaneperoxoate Chemical compound CC(=O)OOC(CCC)CCCCCCC=CC=CC=CC=C GSGNIYIJMYYXBX-UHFFFAOYSA-N 0.000 description 2
- 210000004248 oligodendroglia Anatomy 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 210000005259 peripheral blood Anatomy 0.000 description 2
- 239000011886 peripheral blood Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical class [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000036303 septic shock Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 210000004885 white matter Anatomy 0.000 description 2
- ACVAGHZIHDDOIV-LXPGDDCISA-N (2S)-2-aminobutanedioic acid hexanoic acid Chemical compound CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.OC(=O)[C@@H](N)CC(O)=O ACVAGHZIHDDOIV-LXPGDDCISA-N 0.000 description 1
- ZIOZYRSDNLNNNJ-VXBMJZGYSA-N (5z,8z,10e,14z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid Chemical compound CCCCC\C=C/CC(OO)\C=C\C=C/C\C=C/CCCC(O)=O ZIOZYRSDNLNNNJ-VXBMJZGYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- AKDLBAKGQJFYNB-UHFFFAOYSA-N 2-aminoacetic acid hexanoic acid Chemical compound NCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O AKDLBAKGQJFYNB-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 206010003267 Arthritis reactive Diseases 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 238000011725 BALB/c mouse Methods 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 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 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- YEBDWAHEIMUJQT-XVSDJDOKSA-N CCCCCC=CCC=CCC=CCC=CCCCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YEBDWAHEIMUJQT-XVSDJDOKSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 241001137901 Centropomus undecimalis Species 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- 206010012305 Demyelination Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 201000008370 Discitis Diseases 0.000 description 1
- 206010013710 Drug interaction Diseases 0.000 description 1
- 206010015226 Erythema nodosum Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010015866 Extravasation Diseases 0.000 description 1
- 102000009109 Fc receptors Human genes 0.000 description 1
- 108010087819 Fc receptors Proteins 0.000 description 1
- 102000016359 Fibronectins Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
- 229920001917 Ficoll Polymers 0.000 description 1
- 206010016880 Folate deficiency Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000034826 Genetic Predisposition to Disease Diseases 0.000 description 1
- 206010018341 Gliosis Diseases 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 206010064675 Graft versus host disease in skin Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101150025117 IL3 gene Proteins 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- 102000010789 Interleukin-2 Receptors Human genes 0.000 description 1
- 108010038453 Interleukin-2 Receptors Proteins 0.000 description 1
- 102000004388 Interleukin-4 Human genes 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 102000000743 Interleukin-5 Human genes 0.000 description 1
- 108010002616 Interleukin-5 Proteins 0.000 description 1
- 206010023232 Joint swelling Diseases 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- 208000008771 Lymphadenopathy Diseases 0.000 description 1
- 102000004083 Lymphotoxin-alpha Human genes 0.000 description 1
- 108090000542 Lymphotoxin-alpha Proteins 0.000 description 1
- 241001430197 Mollicutes Species 0.000 description 1
- 208000026072 Motor neurone disease Diseases 0.000 description 1
- 102000047918 Myelin Basic Human genes 0.000 description 1
- 108700028031 Myelin Basic Proteins 0.000 description 1
- 206010028570 Myelopathy Diseases 0.000 description 1
- 208000009525 Myocarditis Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 229930193140 Neomycin Natural products 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000009905 Neurofibromatoses Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- HVAUUPRFYPCOCA-AREMUKBSSA-O PAF Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP(O)(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-O 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033733 Papule Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102000016202 Proteolipids Human genes 0.000 description 1
- 108010010974 Proteolipids Proteins 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 206010040867 Skin hypertrophy Diseases 0.000 description 1
- 206010041549 Spinal cord compression Diseases 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 206010061372 Streptococcal infection Diseases 0.000 description 1
- 230000006052 T cell proliferation Effects 0.000 description 1
- 241000159243 Toxicodendron radicans Species 0.000 description 1
- 241000223997 Toxoplasma gondii Species 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000003092 anti-cytokine Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000011861 anti-inflammatory therapy Methods 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 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
- 238000003556 assay Methods 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000006472 autoimmune response Effects 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003710 calcium ionophore Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 230000010267 cellular communication Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002975 chemoattractant Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 230000036570 collagen biosynthesis Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 229920001971 elastomer Chemical class 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- CJAONIOAQZUHPN-KKLWWLSJSA-N ethyl 12-[[2-[(2r,3r)-3-[2-[(12-ethoxy-12-oxododecyl)-methylamino]-2-oxoethoxy]butan-2-yl]oxyacetyl]-methylamino]dodecanoate Chemical compound CCOC(=O)CCCCCCCCCCCN(C)C(=O)CO[C@H](C)[C@@H](C)OCC(=O)N(C)CCCCCCCCCCCC(=O)OCC CJAONIOAQZUHPN-KKLWWLSJSA-N 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 230000036251 extravasation Effects 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000007387 gliosis Effects 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 210000002443 helper t lymphocyte Anatomy 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000036732 histological change Effects 0.000 description 1
- 230000035874 hyperreactivity Effects 0.000 description 1
- 230000008938 immune dysregulation Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 229940072221 immunoglobulins Drugs 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 229940124589 immunosuppressive drug Drugs 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000006713 insertion reaction Methods 0.000 description 1
- 229940028885 interleukin-4 Drugs 0.000 description 1
- 229940100602 interleukin-5 Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 125000005644 linolenyl group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- KNJDBYZZKAZQNG-UHFFFAOYSA-N lucigenin Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C12=CC=CC=C2[N+](C)=C(C=CC=C2)C2=C1C1=C(C=CC=C2)C2=[N+](C)C2=CC=CC=C12 KNJDBYZZKAZQNG-UHFFFAOYSA-N 0.000 description 1
- 208000018555 lymphatic system disease Diseases 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 description 1
- 229960001810 meprednisone Drugs 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- 210000003007 myelin sheath Anatomy 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000007302 negative regulation of cytokine production Effects 0.000 description 1
- 230000031990 negative regulation of inflammatory response Effects 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 201000004931 neurofibromatosis Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 210000001328 optic nerve Anatomy 0.000 description 1
- 230000004768 organ dysfunction Effects 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000008807 pathological lesion Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 208000008494 pericarditis Diseases 0.000 description 1
- 210000005105 peripheral blood lymphocyte Anatomy 0.000 description 1
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000006461 physiological response Effects 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 208000025889 stromal keratitis Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 229940125379 topical corticosteroid Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 208000009174 transverse myelitis Diseases 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000000264 venule Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
-
- 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
- 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
- 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
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPN9250 | 1996-04-12 | ||
| AUPN9250A AUPN925096A0 (en) | 1996-04-12 | 1996-04-12 | Methods of treatment |
| AUPN9538A AUPN953896A0 (en) | 1996-04-26 | 1996-04-26 | Treatment of t-cell mediated diseases |
| AUPN9538 | 1996-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2251780A1 true CA2251780A1 (en) | 1997-10-23 |
Family
ID=25645159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002251780A Abandoned CA2251780A1 (en) | 1996-04-12 | 1997-04-14 | Methods of treating immunopathologies using polyunsaturated fatty acids |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6262119B1 (https=) |
| EP (1) | EP0904072A4 (https=) |
| JP (1) | JP2000508645A (https=) |
| CA (1) | CA2251780A1 (https=) |
| GB (1) | GB2328155B (https=) |
| WO (1) | WO1997038688A1 (https=) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69914932T2 (de) * | 1998-10-20 | 2004-12-09 | Vlaams Interuniversitair Instituut Voor Biotechnologie Vzw. | Verwendung eines zytokine-produzierenden lactococcus stammes zur behandlung von kolitis |
| AUPQ291499A0 (en) * | 1999-09-17 | 1999-10-07 | Women's And Children's Hospital Adelaide | Novel nitro and sulphur containing compounds |
| NO328803B1 (no) * | 2000-03-03 | 2010-05-18 | Thia Medica | Nye fettsyreanaloger |
| CN100553636C (zh) | 2000-08-04 | 2009-10-28 | Dmi生物科学公司 | 二酮基哌嗪和包含它们的组合物的使用方法 |
| NO20006008L (no) * | 2000-11-28 | 2002-05-29 | Thia Medica As | Fettsyreanaloger for behandling av inflammatoriske og autoimmune sykdommer |
| US7780961B2 (en) * | 2001-05-03 | 2010-08-24 | Actogenix N.V. | Self-containing Lactococcus strain |
| WO2004030522A2 (en) * | 2002-10-02 | 2004-04-15 | Dmi Biosciences, Inc. | Diagnosis and monitoring of diseases |
| AU2003298291A1 (en) * | 2002-11-15 | 2004-06-15 | Universiteit Gent | Self-containing lactobacillus strain |
| GB0311081D0 (en) * | 2003-05-14 | 2003-06-18 | Btg Internat Limted | Treatment of neurodegenerative conditions |
| EP2517718B1 (en) | 2003-05-15 | 2016-03-02 | Ampio Pharmaceuticals, Inc. | Treatment of T-cell mediated diseases |
| FI20060154A7 (fi) | 2003-08-18 | 2006-05-11 | Btg Int Ltd | Neurogeneratiivisten tilojen hoito |
| DE10351111A1 (de) * | 2003-11-03 | 2005-06-16 | Langlotz, Rainer | Arzneimittel und Verfahren zu ihrer Herstellung |
| US20090215895A1 (en) * | 2004-01-30 | 2009-08-27 | Peplin Biolipids Pty Ltd | Therapeutic and carrier molecules |
| US7544714B2 (en) * | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
| GB0425932D0 (en) * | 2004-11-25 | 2004-12-29 | Btg Int Ltd | Structured phospholipids |
| GB0504333D0 (en) * | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Treatment of cytokine dysregulation |
| GB0504362D0 (en) * | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
| US20060246115A1 (en) * | 2005-03-04 | 2006-11-02 | Ricardo Rueda | Nutritional products for ameliorating symptoms of rheumatoid arthritis |
| ES2405552T3 (es) | 2005-11-29 | 2013-05-31 | Actogenix N.V. | Inducción de tolerancia mucosa a antiantígenos de células beta de islotes pancreáticos |
| WO2008090223A2 (en) | 2007-01-25 | 2008-07-31 | Actogenix N.V. | Treatment of immune disease by mucosal delivery of antigens using genetically modified lactobacillus |
| WO2009006668A1 (en) * | 2007-02-05 | 2009-01-15 | Children, Youth And Women's Health Service | Modulators of antigen-dependent t cell proliferation |
| WO2009061208A1 (en) | 2007-11-09 | 2009-05-14 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| JP5856843B2 (ja) | 2008-05-27 | 2016-02-10 | アンピオ ファーマシューティカルズ，インコーポレイテッド | ジケトピペラジンを用いた医薬組成物 |
| EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| BRPI1015120B8 (pt) | 2009-05-08 | 2022-02-15 | Basf As | Composto lipídico alfa-substituídos, derivados de ácidos graxos beta-oxo poli-insaturados, composição farmacêutica e lipídica e métodos para produzir composto lipídico e ácido 2-((5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaeniloxi)butanóico |
| GB0909643D0 (en) * | 2009-06-04 | 2009-07-22 | Avexxin As | Glomerulonephritis treatment |
| GB201014633D0 (en) | 2010-09-02 | 2010-10-13 | Avexxin As | Rheumatoid arthritis treatment |
| EP2613786A4 (en) | 2010-09-07 | 2013-10-23 | Dmi Acquisition Corp | TREATMENT OF DISEASES |
| ES2618604T3 (es) | 2010-11-05 | 2017-06-21 | Pronova Biopharma Norge As | Métodos de tratamiento usando compuestos lipídicos |
| MY172699A (en) | 2011-10-10 | 2019-12-10 | Ampio Pharmaceuticals Inc | Implantable medical devices with increased immune tolerance, and methods for making and implanting |
| EA028343B1 (ru) | 2011-10-10 | 2017-11-30 | Ампио Фармасьютикалз, Инк. | Лечение дегенеративного заболевания сустава |
| EP2771007B1 (en) | 2011-10-28 | 2018-04-04 | Ampio Pharmaceuticals, Inc. | Treatment of rhinitis |
| GB201205394D0 (en) | 2012-03-27 | 2012-05-09 | Adlens Ltd | Improvements in or relating to deformable non-round membrane assemblies |
| CN104219964B (zh) | 2012-03-30 | 2016-09-21 | 奇华顿股份有限公司 | 作为食品加香化合物的n-酰基脯氨酸衍生物 |
| JP6452201B2 (ja) | 2012-03-30 | 2019-01-16 | ジボダン エス エー | 食品フレーバー付与化合物としてのｎ−アシル−アミノ酸誘導体、それらを含有する粉末組成物 |
| CN104254253B (zh) | 2012-03-30 | 2017-12-29 | 奇华顿股份有限公司 | 作为食品加香化合物的n‑酰化甲硫氨酸衍生物 |
| CN104219966B (zh) | 2012-03-30 | 2019-05-28 | 奇华顿股份有限公司 | 作为食品加香化合物的n-酰基-氨基酸衍生物 |
| EP2830437B1 (en) | 2012-03-30 | 2018-12-26 | Givaudan SA | N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds |
| WO2013149008A2 (en) * | 2012-03-30 | 2013-10-03 | Givaudan, S.A. | Improvements in or relating to organic compounds |
| CA2867316C (en) | 2012-03-30 | 2019-10-29 | Givaudan S.A. | N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds |
| EP2830439B1 (en) | 2012-03-30 | 2020-11-04 | Givaudan SA | N-acyl-gaba derivatives for the improvement of the flavour profile of edible compositions |
| GB201221329D0 (en) * | 2012-11-27 | 2013-01-09 | Avexxin As | Dermatitis treatment |
| MX377728B (es) | 2013-02-28 | 2025-03-11 | Pronova Biopharma Norge As | Composición que comprende un compuesto lípido, un triglicerido y un tensioactivo, y métodos de uso de la misma. |
| BR112015020469A2 (pt) | 2013-03-15 | 2020-01-28 | Ampio Pharmaceuticals Inc | Usos de da-dkp, composição e método para fornecimento de células-tronco a umindivíduo |
| WO2015048991A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| WO2015050537A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| US10834950B2 (en) | 2013-10-02 | 2020-11-17 | Givaudan S.A. | Organic compounds |
| WO2015050535A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| US10674755B2 (en) | 2013-10-02 | 2020-06-09 | Givaudan S.A. | Organic Compounds |
| GB201317424D0 (en) | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
| EP3052472B1 (en) | 2013-10-02 | 2019-02-27 | Givaudan S.A. | N-acylated 2-aminoisobutyric acid compounds and flavour compositions containing them |
| GB201409363D0 (en) | 2014-05-27 | 2014-07-09 | Avexxin As | Skin cancer treatment |
| RU2736513C2 (ru) | 2014-08-18 | 2020-11-17 | Ампио Фармасьютикалз, Инк. | Лечение патологических состояний суставов |
| ES2980790T3 (es) | 2015-04-28 | 2024-10-03 | Basf As | Acidos grasos estructuralmente mejorados que contienen azufre para su uso en el tratamiento de la esteatohepatitis no alcohólica |
| EP3310375A4 (en) | 2015-06-22 | 2019-02-20 | Ampio Pharmaceuticals, Inc. | USE OF LOW-MOLECULAR FRACTIONS OF HUMAN SERUMALBUMINE IN THE TREATMENT OF ILLNESSES |
| US11690825B2 (en) | 2016-03-09 | 2023-07-04 | Board Of Regents, The University Of Texas System | 20-HETE receptor (GPR75) antagonists and methods of use |
| GB201604316D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
| CN109789111B (zh) | 2016-09-21 | 2021-11-16 | 埃维克辛公司 | 药物组合物 |
| IL308604B2 (en) | 2017-12-06 | 2025-08-01 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK435087A (da) * | 1986-09-10 | 1988-03-11 | Hoffmann La Roche | Isoprenderivater |
| JPS6372648A (ja) * | 1986-09-16 | 1988-04-02 | Sumitomo Pharmaceut Co Ltd | 新規不飽和脂肪酸誘導体 |
| JPH02225411A (ja) * | 1989-02-28 | 1990-09-07 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸の溶血性低下方法 |
| US5202456A (en) * | 1991-04-15 | 1993-04-13 | The President And Fellows Of Harvard College | Compounds for inhibition of protein methylation |
| DE4120916A1 (de) * | 1991-06-25 | 1993-01-07 | Basf Ag | Omega-3 mehrfach ungesaettigte fettsaeurederivate, ihre herstellung und verwendung |
| NL9201438A (nl) * | 1992-08-11 | 1994-03-01 | Prospa Bv | Nieuwe farmaceutische samenstellingen die esters van omega-3 polyonverzadigde zuren omvatten en de toepassing ervan bij de plaatselijke behandeling van ziekelijke aandoeningen. |
| 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 |
| AU6511794A (en) * | 1993-03-29 | 1994-10-24 | Cecil R. Pace-Asciak | Hepoxilin analogs useful as anti-inflammatory agents |
| AU3156595A (en) * | 1994-08-11 | 1996-03-07 | J.W. Broadbent Nominees Pty. Ltd. | Anti-inflammatory preparation |
| AUPM740594A0 (en) | 1994-08-11 | 1994-09-01 | J.W. Broadbent Nominees Pty. Ltd. | Anti-inflammatory preparation |
| JPH10507179A (ja) | 1994-10-13 | 1998-07-14 | ペプチド テクノロジー リミテッド | 修飾ポリ不飽和脂肪酸 |
| AU698476B2 (en) * | 1994-10-13 | 1998-10-29 | Children, Youth And Women's Health Service Incorporated | Modified polyunsaturated fatty acids |
| AUPM906594A0 (en) | 1994-10-26 | 1994-11-17 | Peptide Technology Limited | Synthetic polyunsaturated fatty acid analogues |
| AU686898B2 (en) * | 1994-10-26 | 1998-02-12 | Children, Youth And Women's Health Service Incorporated | Synthetic polyunsaturated fatty acid analogues |
| MY118354A (en) * | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
| US5585400A (en) * | 1996-02-27 | 1996-12-17 | Wisconsin Alumni Research Foundation | Methods of attenuating the allergic response in animals |
-
1997
- 1997-04-14 WO PCT/AU1997/000231 patent/WO1997038688A1/en not_active Ceased
- 1997-04-14 EP EP97916266A patent/EP0904072A4/en not_active Ceased
- 1997-04-14 GB GB9822203A patent/GB2328155B/en not_active Expired - Fee Related
- 1997-04-14 CA CA002251780A patent/CA2251780A1/en not_active Abandoned
- 1997-04-14 JP JP9536587A patent/JP2000508645A/ja active Pending
- 1997-04-14 US US09/171,095 patent/US6262119B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0904072A4 (en) | 2003-07-30 |
| WO1997038688A1 (en) | 1997-10-23 |
| US6262119B1 (en) | 2001-07-17 |
| GB2328155A (en) | 1999-02-17 |
| JP2000508645A (ja) | 2000-07-11 |
| GB2328155B (en) | 2000-08-02 |
| GB9822203D0 (en) | 1998-12-02 |
| EP0904072A1 (en) | 1999-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2251780A1 (en) | Methods of treating immunopathologies using polyunsaturated fatty acids | |
| US6376688B1 (en) | Modified polyunsaturated fatty acids | |
| US8071613B2 (en) | Anti-constipation composition | |
| JP5059996B2 (ja) | 新規インターロイキン−１および腫瘍壊死因子−αモジュレーター、前記モジュレーターの合成、ならびに前記モジュレーターの使用方法 | |
| SK280450B6 (sk) | 20-metylsubstituované deriváty vitamínu d, spôsob | |
| US5998476A (en) | Synthetic polyunsaturated fatty acid analogues | |
| IL82459A (en) | Stabilized pharmaceutical preparations containing polyunsaturated fatty acids and stimulating the synthesis of prostaglandins and hydroxy- and fatty acids in B systems | |
| CA2366186C (en) | Retinoid antagonists and use thereof | |
| NZ226362A (en) | A cathartic (laxative) composition comprising a 15-keto-16-halogen-prostaglandin | |
| Ylitalo et al. | Effect of exercise on the serum level and urinary excretion of tetracycline, doxycycline and sulphamethizole | |
| AU609428B2 (en) | Use of carboxylic acid amides | |
| GB2038818A (en) | ???,???-Dihydropolyprenyl Alcohols and Pharmaceutical Compositions thereof | |
| AU726798B2 (en) | Methods of treating immunopathologies using polyunsaturated fatty acids | |
| AU698476B2 (en) | Modified polyunsaturated fatty acids | |
| EP0574185B1 (en) | PGE1 analogs | |
| AU686898B2 (en) | Synthetic polyunsaturated fatty acid analogues | |
| US4405810A (en) | 7-Aryl-hept-5-ynoic acids and derivatives thereof | |
| JPH06199779A (ja) | トランス−▲δ２▼−１５−デオキシ−１６−ヒドロキシ−１６−メチル−ｐｇ▲ｅ１▼のメチルエステル（ｂ−４０７） | |
| US4814490A (en) | Organopalladium approaches to prostaglandins | |
| Demers | Prostaglandins in human disease | |
| CA1198372A (en) | Treatment of diseases of the liver, kidney, colon and rectum | |
| US4424374A (en) | Bicycloheptane derivatives | |
| WO2006019353A9 (en) | Composition and method for the treatement of psoriasis | |
| JPH089540B2 (ja) | 腫瘍壊死因子遊離抑制剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |