CA2424555A1 - Triptolide analogs for the treatment of autoimmune and inflammatory disorders - Google Patents
Triptolide analogs for the treatment of autoimmune and inflammatory disorders Download PDFInfo
- Publication number
- CA2424555A1 CA2424555A1 CA002424555A CA2424555A CA2424555A1 CA 2424555 A1 CA2424555 A1 CA 2424555A1 CA 002424555 A CA002424555 A CA 002424555A CA 2424555 A CA2424555 A CA 2424555A CA 2424555 A1 CA2424555 A1 CA 2424555A1
- Authority
- CA
- Canada
- Prior art keywords
- residue
- natural
- heterocyclic
- aryl
- cycloalkyl
- 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
- 238000011282 treatment Methods 0.000 title claims abstract description 39
- 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 25
- 208000023275 Autoimmune disease Diseases 0.000 title claims description 25
- 230000001363 autoimmune Effects 0.000 title abstract description 17
- DFBIRQPKNDILPW-CIVMWXNOSA-N Triptolide Chemical class O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 DFBIRQPKNDILPW-CIVMWXNOSA-N 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 220
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims description 339
- 125000000623 heterocyclic group Chemical group 0.000 claims description 339
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 333
- 229910052739 hydrogen Inorganic materials 0.000 claims description 300
- 150000001413 amino acids Chemical class 0.000 claims description 299
- 150000001720 carbohydrates Chemical class 0.000 claims description 299
- 239000001257 hydrogen Substances 0.000 claims description 299
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 296
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 293
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 290
- 125000000217 alkyl group Chemical group 0.000 claims description 280
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 257
- 150000002148 esters Chemical class 0.000 claims description 257
- 125000001072 heteroaryl group Chemical group 0.000 claims description 244
- -1 alkcarbonyl Chemical group 0.000 claims description 237
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 224
- 125000003342 alkenyl group Chemical group 0.000 claims description 179
- 125000000304 alkynyl group Chemical group 0.000 claims description 174
- 150000003839 salts Chemical class 0.000 claims description 150
- 150000001408 amides Chemical class 0.000 claims description 149
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 149
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 149
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 149
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 149
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 149
- 150000001735 carboxylic acids Chemical class 0.000 claims description 148
- 125000005499 phosphonyl group Chemical group 0.000 claims description 148
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 148
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 147
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 120
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 114
- 229910052760 oxygen Inorganic materials 0.000 claims description 112
- 229910052717 sulfur Inorganic materials 0.000 claims description 85
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- 150000001412 amines Chemical class 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 150000004703 alkoxides Chemical class 0.000 claims description 37
- 239000003937 drug carrier Substances 0.000 claims description 27
- 238000011321 prophylaxis Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000003018 immunosuppressive agent Substances 0.000 claims description 17
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 14
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 5
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 20
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 238000010189 synthetic method Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 description 260
- 150000004820 halides Chemical class 0.000 description 217
- 229940002612 prodrug Drugs 0.000 description 130
- 239000000651 prodrug Substances 0.000 description 130
- 101100113998 Mus musculus Cnbd2 gene Proteins 0.000 description 95
- 101000869592 Daucus carota Major allergen Dau c 1 Proteins 0.000 description 81
- 101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Proteins 0.000 description 81
- 102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 description 81
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 210000001519 tissue Anatomy 0.000 description 13
- 230000004913 activation Effects 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 230000006378 damage Effects 0.000 description 12
- 210000003622 mature neutrocyte Anatomy 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 description 11
- 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 11
- 229960003444 immunosuppressant agent Drugs 0.000 description 11
- 230000001861 immunosuppressant effect Effects 0.000 description 11
- 210000002540 macrophage Anatomy 0.000 description 11
- 239000000427 antigen Substances 0.000 description 10
- 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 10
- 208000027418 Wounds and injury Diseases 0.000 description 9
- 102000036639 antigens Human genes 0.000 description 9
- 108091007433 antigens Proteins 0.000 description 9
- 210000000987 immune system Anatomy 0.000 description 9
- 208000014674 injury Diseases 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 206010018364 Glomerulonephritis Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- 210000000265 leukocyte Anatomy 0.000 description 8
- 102000004127 Cytokines Human genes 0.000 description 7
- 108090000695 Cytokines Proteins 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000002054 transplantation Methods 0.000 description 7
- 206010061218 Inflammation Diseases 0.000 description 6
- 101100545004 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YSP2 gene Proteins 0.000 description 6
- 210000001744 T-lymphocyte Anatomy 0.000 description 6
- 241000830536 Tripterygium wilfordii Species 0.000 description 6
- 230000028993 immune response Effects 0.000 description 6
- 230000001506 immunosuppresive effect Effects 0.000 description 6
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 description 6
- 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 5
- 229930105110 Cyclosporin A Natural products 0.000 description 5
- 108010036949 Cyclosporine Proteins 0.000 description 5
- 108010002352 Interleukin-1 Proteins 0.000 description 5
- 102000000589 Interleukin-1 Human genes 0.000 description 5
- 229960001265 ciclosporin Drugs 0.000 description 5
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 5
- 150000002617 leukotrienes Chemical class 0.000 description 5
- IXAQOQZEOGMIQS-SSQFXEBMSA-N lipoxin A4 Chemical compound CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O IXAQOQZEOGMIQS-SSQFXEBMSA-N 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 108010002350 Interleukin-2 Proteins 0.000 description 4
- 102000000588 Interleukin-2 Human genes 0.000 description 4
- 102000003820 Lipoxygenases Human genes 0.000 description 4
- 108090000128 Lipoxygenases Proteins 0.000 description 4
- 102100022364 Polyunsaturated fatty acid 5-lipoxygenase Human genes 0.000 description 4
- 101710156627 Polyunsaturated fatty acid 5-lipoxygenase Proteins 0.000 description 4
- 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 description 4
- 210000003719 b-lymphocyte Anatomy 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 210000000885 nephron Anatomy 0.000 description 4
- 230000035755 proliferation Effects 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 101100264222 Arabidopsis thaliana XRI1 gene Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 description 3
- 229930184725 Lipoxin Natural products 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
- 101000927076 Xenopus laevis Apoptosis regulator R11 Proteins 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 230000001434 glomerular Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000008595 infiltration Effects 0.000 description 3
- 238000001764 infiltration Methods 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 150000002639 lipoxins Chemical class 0.000 description 3
- 210000003584 mesangial cell Anatomy 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 239000008177 pharmaceutical agent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 229930004725 sesquiterpene Natural products 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000015398 thunder god vine Nutrition 0.000 description 3
- YKUJZZHGTWVWHA-UHFFFAOYSA-N triptolide Natural products COC12CC3OC3(C(C)C)C(O)C14OC4CC5C6=C(CCC25C)C(=O)OC6 YKUJZZHGTWVWHA-UHFFFAOYSA-N 0.000 description 3
- 102000003390 tumor necrosis factor Human genes 0.000 description 3
- GWXSHQWMMUKHDX-UHFFFAOYSA-N 10-hydroxy-2,4a,6a,8a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,6a,6b,7,8,13,14,14b-dodecahydropicene-2-carboxylic acid Chemical compound C12CC(C)(C(O)=O)CCC2(C)CCC2(C)C1(C)CCC1C3=CC(=O)C(O)=C(C)C3(C)CCC12 GWXSHQWMMUKHDX-UHFFFAOYSA-N 0.000 description 2
- KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 2
- KGIJOOYOSFUGPC-XRXZHELTSA-N 5-hydroxyeicosatetraenoic acid Natural products CCCCCC=CCC=CCC=C\C=C\C(O)CCCC(O)=O KGIJOOYOSFUGPC-XRXZHELTSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101100455054 Homo sapiens LTA4H gene Proteins 0.000 description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 101100075025 Scheffersomyces stipitis (strain ATCC 58785 / CBS 6054 / NBRC 10063 / NRRL Y-11545) LTA4 gene Proteins 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 206010046851 Uveitis Diseases 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229960002170 azathioprine Drugs 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
- KQJSQWZMSAGSHN-JJWQIEBTSA-N celastrol Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)[C@](C)(C(O)=O)CC[C@]1(C)CC[C@]2(C)C4=CC=C1C3=CC(=O)C(O)=C1C KQJSQWZMSAGSHN-JJWQIEBTSA-N 0.000 description 2
- 230000003399 chemotactic effect Effects 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- 229930182912 cyclosporin Natural products 0.000 description 2
- 229930004069 diterpene Natural products 0.000 description 2
- 210000003038 endothelium Anatomy 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 210000005086 glomerual capillary Anatomy 0.000 description 2
- 210000003904 glomerular cell Anatomy 0.000 description 2
- 210000000224 granular leucocyte Anatomy 0.000 description 2
- 210000002443 helper t lymphocyte Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- UFPQIRYSPUYQHK-WAQVJNLQSA-N leukotriene A4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O UFPQIRYSPUYQHK-WAQVJNLQSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 2
- 229960000485 methotrexate Drugs 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 210000001616 monocyte Anatomy 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 231100000004 severe toxicity Toxicity 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FKVGKCKPWUXRCC-NYRONZRESA-N (1R,2S,5R,6R,8S,11S,12R)-2,6-dihydroxy-6,12-dimethyl-14-oxapentacyclo[10.3.3.15,8.01,11.02,8]nonadecan-13-one Chemical compound C[C@@]1(O)C[C@]23C[C@H]1CC[C@@]2(O)[C@]12CCC[C@](C)([C@H]1CC3)C(=O)OC2 FKVGKCKPWUXRCC-NYRONZRESA-N 0.000 description 1
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
- KPXIBWGPZSPABK-FXAWDEMLSA-N (3bR,9bS)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e]isobenzofuran-1-one Chemical compound C1C[C@]2(C)C3=CC=C(C(C)C)C(O)=C3CC[C@H]2C2=C1C(=O)OC2 KPXIBWGPZSPABK-FXAWDEMLSA-N 0.000 description 1
- KQJSQWZMSAGSHN-UHFFFAOYSA-N (9beta,13alpha,14beta,20alpha)-3-hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid Natural products CC12CCC3(C)C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C2=CC=C2C1=CC(=O)C(O)=C2C KQJSQWZMSAGSHN-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- HPTCYMNPHWXVLA-UBBHAYRHSA-N 16-hydroxytriptolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1([C@H](CO)C)[C@@H](O)[C@]21[C@H]3O1 HPTCYMNPHWXVLA-UBBHAYRHSA-N 0.000 description 1
- 208000032467 Aplastic anaemia Diseases 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241001367053 Autographa gamma Species 0.000 description 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
- 206010004659 Biliary cirrhosis Diseases 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- AQKDBFWJOPNOKZ-UHFFFAOYSA-N Celastrol Natural products CC12CCC3(C)C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C2=CC=C2C1=CC(=O)C(=O)C2C AQKDBFWJOPNOKZ-UHFFFAOYSA-N 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 102000010918 Cysteinyl leukotriene receptors Human genes 0.000 description 1
- 108050001116 Cysteinyl leukotriene receptors Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 102000005720 Glutathione transferase Human genes 0.000 description 1
- 108010070675 Glutathione transferase Proteins 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 101000958041 Homo sapiens Musculin Proteins 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 102100037850 Interferon gamma Human genes 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 102000004388 Interleukin-4 Human genes 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 108010002616 Interleukin-5 Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- 108010074338 Lymphokines Proteins 0.000 description 1
- 102000008072 Lymphokines Human genes 0.000 description 1
- 206010064912 Malignant transformation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- 208000013901 Nephropathies and tubular disease Diseases 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 102000003923 Protein Kinase C Human genes 0.000 description 1
- 108090000315 Protein Kinase C Proteins 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 230000006044 T cell activation Effects 0.000 description 1
- 108091008874 T cell receptors Proteins 0.000 description 1
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- VIYFRTDWJXBEDM-UHFFFAOYSA-N Triptophenolide Natural products CC(C)c1ccc2c(CCC3C4=COC(=O)C4=CCC23C)c1O VIYFRTDWJXBEDM-UHFFFAOYSA-N 0.000 description 1
- 206010048302 Tubulointerstitial nephritis Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000009692 acute damage Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 210000001552 airway epithelial cell Anatomy 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000665 anti-chemotactic effect Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 230000005875 antibody response Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 229940033495 antimalarials Drugs 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 229940114078 arachidonate Drugs 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000006470 autoimmune attack Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 239000003710 calcium ionophore Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- UFWLHIVKHDCSHZ-UHFFFAOYSA-N chembl1595789 Chemical compound NC1=NC(N)=NC(C=2C(=CC=CC=2)O)=N1 UFWLHIVKHDCSHZ-UHFFFAOYSA-N 0.000 description 1
- 230000035605 chemotaxis Effects 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 231100000850 chronic interstitial nephritis Toxicity 0.000 description 1
- 229940047120 colony stimulating factors Drugs 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 208000018631 connective tissue disease Diseases 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012926 crystallographic analysis Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 239000002988 disease modifying antirheumatic drug Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 150000004141 diterpene derivatives Chemical group 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 210000002919 epithelial cell Anatomy 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
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 230000009795 fibrotic process Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000024924 glomerular filtration Effects 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 102000046949 human MSC Human genes 0.000 description 1
- 230000005934 immune activation Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 229940124589 immunosuppressive drug Drugs 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- YIBQGGFZCZIJOB-UHFFFAOYSA-N isowilfordine Natural products CC(=O)OC1C2(COC(=O)C)C(OC(C)=O)C(OC(C)=O)C3C(OC(C)=O)C2(C2(C)O)OC3(C)COC(=O)C3=CN=CC=C3CCC(C)(O)C(=O)OC2C1OC(=O)C1=CC=CC=C1 YIBQGGFZCZIJOB-UHFFFAOYSA-N 0.000 description 1
- 238000011862 kidney biopsy Methods 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 108010072713 leukotriene A4 hydrolase Proteins 0.000 description 1
- OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 description 1
- UXVRTOKOJOMENI-WLPVFMORSA-N lipoxin B4 Chemical compound CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O UXVRTOKOJOMENI-WLPVFMORSA-N 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000036212 malign transformation Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- 229960004961 mechlorethamine Drugs 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000004783 oxidative metabolism Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000003617 peroxidasic effect Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000003906 phosphoinositides Chemical class 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 230000004983 pleiotropic effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000001995 reticulocyte Anatomy 0.000 description 1
- 102220112179 rs3743602 Human genes 0.000 description 1
- ZXENWDWQTWYUGY-UUZWCOCASA-N salaspermic acid Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)[C@](C)(C(O)=O)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(CO2)[C@H]3CC[C@@]2(O)[C@@H]1C ZXENWDWQTWYUGY-UUZWCOCASA-N 0.000 description 1
- QEIFWJNSWAONFY-UHFFFAOYSA-N salaspermic acid Natural products CC1CC2C(C)(CCC3(C)C4CCC56C(C)C(O)(CCC5C4(C)CCC23C)OC6=O)C(O)C1=O QEIFWJNSWAONFY-UHFFFAOYSA-N 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 230000003033 spasmogenic effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000000638 stimulation Effects 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
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- OIMACDABKWJVSQ-LZVGCMTRSA-N tripchlorolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H](Cl)[C@](C(C)C)(O)[C@@H](O)[C@]21[C@H]3O1 OIMACDABKWJVSQ-LZVGCMTRSA-N 0.000 description 1
- FKVGKCKPWUXRCC-UHFFFAOYSA-N tripterinin Natural products C1CCC(C)(C2CC3)C(=O)OCC21C1(O)CCC2CC13CC2(O)C FKVGKCKPWUXRCC-UHFFFAOYSA-N 0.000 description 1
- IWVWTVWLRSUYNC-UHFFFAOYSA-N triptocallic acid A Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)C(O)CC(C(O)=O)C(C)C5C4=CCC3C21C IWVWTVWLRSUYNC-UHFFFAOYSA-N 0.000 description 1
- SWOVVKGLGOOUKI-ZHGGVEMFSA-N triptonide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)C(=O)[C@]21[C@H]3O1 SWOVVKGLGOOUKI-ZHGGVEMFSA-N 0.000 description 1
- DYVDZVMUDBCZSA-LZVGCMTRSA-N triptriolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H](O)[C@](C(C)C)(O)[C@@H](O)[C@]21[C@H]3O1 DYVDZVMUDBCZSA-LZVGCMTRSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23755700P | 2000-10-02 | 2000-10-02 | |
| US60/237,557 | 2000-10-02 | ||
| PCT/US2001/030951 WO2002028862A2 (en) | 2000-10-02 | 2001-10-02 | Triptolide analogs for the treatment of autoimmune and inflammatory disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2424555A1 true CA2424555A1 (en) | 2002-04-11 |
Family
ID=22894243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002424555A Abandoned CA2424555A1 (en) | 2000-10-02 | 2001-10-02 | Triptolide analogs for the treatment of autoimmune and inflammatory disorders |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6777441B2 (https=) |
| EP (2) | EP1330459B1 (https=) |
| JP (2) | JP4269144B2 (https=) |
| AT (2) | ATE469907T1 (https=) |
| AU (2) | AU9654201A (https=) |
| CA (1) | CA2424555A1 (https=) |
| DE (2) | DE60121986T2 (https=) |
| WO (1) | WO2002028862A2 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002028862A2 (en) | 2000-10-02 | 2002-04-11 | Emory University | Triptolide analogs for the treatment of autoimmune and inflammatory disorders |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| EP2468277A1 (en) * | 2002-05-31 | 2012-06-27 | Pharmagenesis, Inc. | Triptolide derivatives for modulation of apoptosis and immunosuppression |
| WO2004023984A2 (en) * | 2002-09-13 | 2004-03-25 | Smith C Steven | Novel composition and method for treatment of upper respiratory conditions |
| TW200509958A (en) * | 2003-02-14 | 2005-03-16 | Combinatorx Inc | Methods and reagents for the treatment of diseases and disorders associated with increased levels of proinflammatory cytokines |
| WO2005012294A1 (en) * | 2003-07-30 | 2005-02-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| US20050192261A1 (en) * | 2003-09-15 | 2005-09-01 | Jost-Price Edward R. | Methods and reagents for the treatment of immunoinflammatory disorders |
| WO2005062913A2 (en) * | 2003-12-24 | 2005-07-14 | Pharmagenesis, Inc. | Triplide 5,6-derivatives as immunomodulators and anticancer agents |
| EP1722806A4 (en) * | 2004-02-09 | 2009-09-16 | Pharmagenesis Inc | METHOD OF ISOLATING TRIPTOLIDE COMPOUNDS FROM TRIPTERYGIUM WILFORDII |
| WO2005084365A2 (en) * | 2004-03-02 | 2005-09-15 | Pharmagenesis, Inc. | Triptolide lactone ring derivatives as immunomodulators and anticancer agents |
| WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
| WO2006012204A2 (en) * | 2004-06-25 | 2006-02-02 | Pharmagenesis, Inc. | Method for treatment of inflammatory disorders using triptolide compounds |
| WO2006044496A2 (en) * | 2004-10-13 | 2006-04-27 | Pharmagenesis, Inc. | Identification and screening of triptolide target molecules |
| WO2007053844A2 (en) * | 2005-10-31 | 2007-05-10 | Rigel Pharmaceuticals, Inc. | Compositions and methods for treating inflammatory disorders |
| EP2240460A4 (en) * | 2008-01-07 | 2012-02-22 | Univ Emory | BRANCHED DIEPXYDE COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS |
| US8147882B2 (en) | 2009-09-30 | 2012-04-03 | Leonard Lomax | Herbal pain killer compositions |
| CN104478832B (zh) * | 2015-01-05 | 2016-04-20 | 项敬来 | 二萜化合物，含其的药物组合物及其制备方法和应用 |
| JP6743135B2 (ja) * | 2015-09-02 | 2020-08-19 | アッヴィ・インコーポレイテッド | 抗ウィルス性テトラヒドロフラン誘導体 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1179866A (en) * | 1967-09-08 | 1970-02-04 | Agfa Gevaert Nv | Photopolymerisation of Ethylenically Unsaturated Organic Compounds |
| US3917652A (en) * | 1968-04-29 | 1975-11-04 | Hoffmann La Roche | Juvabione and derivatives thereof |
| BE789948A (fr) * | 1971-10-13 | 1973-04-11 | Sandoz Sa | Nouveaux derives du pyrazole, leur preparation et leur application comme medicaments |
| US3816437A (en) * | 1972-12-22 | 1974-06-11 | Sandoz Ag | Thieno(2,3-g)indazoles |
| US3957816A (en) * | 1973-01-31 | 1976-05-18 | Sandoz, Inc. | Substituted naphtho pyrazoles |
| JPS5473766A (en) | 1977-11-21 | 1979-06-13 | Nippon Terpen Kagaku Kk | Manufacture of menthofuran |
| GB2104516B (en) | 1981-07-13 | 1985-12-04 | Univ Brunel | M-alkylphenol derivatives and their use in copper extraction |
| DE3219048A1 (de) | 1982-05-21 | 1983-11-24 | Basf Ag, 6700 Ludwigshafen | Thermoplastische formmassen |
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| DE3440826A1 (de) | 1983-11-10 | 1985-05-23 | Basf Ag, 6700 Ludwigshafen | 1,1-ethanoretinsaeuren und ihre c(pfeil abwaerts)1(pfeil abwaerts)-c(pfeil abwaerts)4(pfeil abwaerts)-alkylester |
| JPS61197573A (ja) | 1985-02-26 | 1986-09-01 | Chugai Pharmaceut Co Ltd | ５，６−エポキシ化トランスビタミンｄ３ |
| JP2865211B2 (ja) | 1988-09-15 | 1999-03-08 | ファルマシア・アンド・アップジョン・カンパニー | ５’―インドリニル―５β―アミドメチルオキサゾリジン―２―オン類、３―（縮合環置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類および３―（窒素原子置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類 |
| DE3913310A1 (de) | 1989-04-20 | 1990-10-25 | Schering Ag | Spirocyclopropane in der vitamin d-reihe |
| JPH03197464A (ja) | 1989-12-16 | 1991-08-28 | Basf Ag | 置換アゾリルメチルシクロアルカノール及びこれを含有する殺菌剤 |
| US5430054A (en) * | 1989-12-22 | 1995-07-04 | Jiangsu Family Planning Institute | Preparation methods of diterpene lactone compounds and application of the same to antifertility |
| AU7570191A (en) * | 1990-03-14 | 1991-10-10 | Board Of Regents, The University Of Texas System | Tripterygium wilfordii hook f extracts and components thereof for immunosuppression |
| US5216175A (en) * | 1990-03-23 | 1993-06-01 | Sri International | Antimalarial analogs of artemisinin |
| US5581004A (en) * | 1991-09-23 | 1996-12-03 | Board Of Regents Of The University Of Nebraska | Preparation and use of (2-butene-1,4-diyl) magnesium complexes in organic synthesis |
| AU2466092A (en) | 1992-07-22 | 1994-02-14 | Michael F. Lucey | Highly filled polymeric compositions |
| WO1994026265A1 (en) * | 1993-05-06 | 1994-11-24 | Pharmagenesis, Inc. | 16-hydroxytriptolide composition and method for immunotherapy |
| FR2707992B1 (fr) | 1993-07-21 | 1995-10-13 | Flamel Tech Sa | Nouveaux produits organiques contenant des fonctions thiols réactives, l'un de leurs procédés de préparation et les biomatériaux les contenant. |
| GB9325415D0 (en) | 1993-12-13 | 1994-02-16 | Res Inst Medicine Chem | Chemical compounds |
| GB9405715D0 (en) | 1994-03-23 | 1994-05-11 | Res Inst Medicine Chem | Chemical compounds |
| FR2733498B1 (fr) * | 1995-04-27 | 1997-05-30 | Adir | Nouveaux composes cyclohexaniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5723632A (en) * | 1996-08-08 | 1998-03-03 | Mgi Pharma, Inc. | Total synthesis of antitumor acylfulvenes |
| IT1287174B1 (it) | 1996-11-15 | 1998-08-04 | Angelini Ricerche Spa | Diaril-ciclometilenpirazoli farmacologicamente attivi,procedimento per prepararli e composizioni farmaceutiche che li contengono |
| US5972998A (en) * | 1997-05-23 | 1999-10-26 | Hoechst Marion Roussel, Inc. | Triptolide derivatives useful in the treatment of autoimmune diseases |
| WO1999019298A1 (en) | 1997-10-14 | 1999-04-22 | The Scripps Research Institute | iso-CBI AND iso-CI ANALOGS OF CC-1065 AND THE DUOCARMYCINS |
| NZ504884A (en) | 1997-12-08 | 2002-10-25 | Scripps Research Inst | Synthesis of the dihydroindole C-ring of CC-1065/duocarmycin analogs and certain intermediates |
| DE19855859A1 (de) * | 1998-12-03 | 2000-06-08 | Degussa | Katalysatoren für die enantioselektive Epoxidierung von C=C-Doppelbindungen |
| FR2787451B1 (fr) * | 1998-12-18 | 2001-01-26 | Adir | Nouveaux composes imidazoliniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AR023071A1 (es) | 1998-12-23 | 2002-09-04 | Syngenta Participations Ag | Compuestos de piridincetona, compuestos intermediarios, composicion herbicida e inhibidora del crecimiento de plantas, metodo para controlar la vegetacion indeseada, metodo para inhibir el crecimiento de las plantas, y uso de la composicion para controlar el crecimiento indeseado de plantas. |
| US6331642B1 (en) | 1999-07-12 | 2001-12-18 | Hoffmann-La Roche Inc. | Vitamin D3 analogs |
| WO2002028862A2 (en) * | 2000-10-02 | 2002-04-11 | Emory University | Triptolide analogs for the treatment of autoimmune and inflammatory disorders |
| US20040204394A1 (en) * | 2003-04-11 | 2004-10-14 | Aderis Pharmaceuticals, Inc. | Triptolide analogues |
-
2001
- 2001-10-02 WO PCT/US2001/030951 patent/WO2002028862A2/en not_active Ceased
- 2001-10-02 AU AU9654201A patent/AU9654201A/xx active Pending
- 2001-10-02 US US09/970,089 patent/US6777441B2/en not_active Expired - Lifetime
- 2001-10-02 AT AT05077239T patent/ATE469907T1/de not_active IP Right Cessation
- 2001-10-02 DE DE60121986T patent/DE60121986T2/de not_active Expired - Lifetime
- 2001-10-02 AU AU2001296542A patent/AU2001296542B2/en not_active Ceased
- 2001-10-02 DE DE60142313T patent/DE60142313D1/de not_active Expired - Lifetime
- 2001-10-02 JP JP2002532445A patent/JP4269144B2/ja not_active Expired - Fee Related
- 2001-10-02 EP EP01977423A patent/EP1330459B1/en not_active Expired - Lifetime
- 2001-10-02 EP EP05077239A patent/EP1659125B1/en not_active Expired - Lifetime
- 2001-10-02 AT AT01977423T patent/ATE334986T1/de not_active IP Right Cessation
- 2001-10-02 CA CA002424555A patent/CA2424555A1/en not_active Abandoned
-
2004
- 2004-08-17 US US10/919,824 patent/US7557139B2/en not_active Expired - Fee Related
-
2008
- 2008-12-25 JP JP2008331610A patent/JP2009102371A/ja active Pending
-
2009
- 2009-05-29 US US12/474,305 patent/US8193249B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU9654201A (en) | 2002-04-15 |
| WO2002028862A2 (en) | 2002-04-11 |
| US8193249B2 (en) | 2012-06-05 |
| WO2002028862A3 (en) | 2002-09-12 |
| ATE334986T1 (de) | 2006-08-15 |
| DE60121986D1 (de) | 2006-09-14 |
| JP2004525082A (ja) | 2004-08-19 |
| DE60142313D1 (de) | 2010-07-15 |
| US20060040907A1 (en) | 2006-02-23 |
| EP1659125A1 (en) | 2006-05-24 |
| DE60121986T2 (de) | 2007-07-26 |
| AU2001296542B9 (en) | 2002-04-15 |
| US7557139B2 (en) | 2009-07-07 |
| JP4269144B2 (ja) | 2009-05-27 |
| AU2001296542B2 (en) | 2007-10-25 |
| JP2009102371A (ja) | 2009-05-14 |
| US20030027806A1 (en) | 2003-02-06 |
| US20090234000A1 (en) | 2009-09-17 |
| EP1659125B1 (en) | 2010-06-02 |
| US6777441B2 (en) | 2004-08-17 |
| EP1330459B1 (en) | 2006-08-02 |
| ATE469907T1 (de) | 2010-06-15 |
| EP1330459A2 (en) | 2003-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2424555A1 (en) | Triptolide analogs for the treatment of autoimmune and inflammatory disorders | |
| US5843452A (en) | Immunotherapy composition and method | |
| JPH0154339B2 (https=) | ||
| EP1412317A1 (en) | Retinoid derivatives with antiangiogenic, antitumor and proapoptotic activities | |
| AU2002326144A1 (en) | Retinoid derivatives with antiangiogenic, antitumoral and proapoptotic activities | |
| JP2004525082A5 (https=) | ||
| EP0810861A1 (en) | Suksdorfin analogs, compositions thereof, and methods for making and using thereof | |
| Zhang et al. | Synthesis, and anti-inflammatory activities of gentiopicroside derivatives | |
| JP2011525486A (ja) | 活動亢進性免疫系を治療するためのシクロリグナンの使用 | |
| US7196115B2 (en) | Pharmaceutical composition containing brevifoliol for use in chemotherapeutic treatment of human beings, method therefor | |
| AU2001296542A1 (en) | Triptolide analogs for the treatment of autoimmune and inflammatory disorders | |
| US8119686B2 (en) | Spiroquinone compound and pharmaceutical composition | |
| WO2003077832A2 (en) | Dexanabinol and dexanabinol analogs regulate inflammation related genes | |
| JPH0798746B2 (ja) | リソゾ−ム放出抑制剤 | |
| EP1284263B1 (en) | Derivatives of p- hydroxy phenyl propionic acid as antiproliferative agents | |
| JP2754644B2 (ja) | 新規リグナン類およびリグナン類を有効成分とする５―リポキシゲナーゼ阻害剤およびアルドースリダクターゼ阻害剤 | |
| CN1261272A (zh) | 抗癌剂 | |
| US4883813A (en) | Method of treating inflammation in mammals utilizing ketobutyrolactones and furylbutyrolactones | |
| JP4781624B2 (ja) | Ｒａｎｔｅｓ誘導剤 | |
| CA2467926A1 (en) | Biologically active complex | |
| WO2025104281A1 (en) | Hop derived compounds for use in the treatment of diseases caused by coronaviruses | |
| EP0289203A1 (en) | Antitumor and antiviral compounds of marine origin | |
| JPH0259525A (ja) | アセトゲニンより成る治療用駆虫薬 | |
| JPH072886A (ja) | 血小板増多剤ロイストロダクシンｈ | |
| JPH0413676A (ja) | 腫瘍壊死因子遊離抑制剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |