UA60308C2 - ЗАМІЩЕНІ 2-(2,6-ДІОКСОПІПЕРИДИН-3-ІЛ)ФТАЛІМІДИ ТА 1-ОКСОІЗОІНДОЛІНИ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЗНИЖЕННЯ РІВНЯ ФПН-α - Google Patents
ЗАМІЩЕНІ 2-(2,6-ДІОКСОПІПЕРИДИН-3-ІЛ)ФТАЛІМІДИ ТА 1-ОКСОІЗОІНДОЛІНИ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЗНИЖЕННЯ РІВНЯ ФПН-α Download PDFInfo
- Publication number
- UA60308C2 UA60308C2 UA99010371A UA99010371A UA60308C2 UA 60308 C2 UA60308 C2 UA 60308C2 UA 99010371 A UA99010371 A UA 99010371A UA 99010371 A UA99010371 A UA 99010371A UA 60308 C2 UA60308 C2 UA 60308C2
- Authority
- UA
- Ukraine
- Prior art keywords
- oxo
- dioxopiperidin
- aminoisoindoline
- dione
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- FPNJYPLJTAYAMP-UHFFFAOYSA-N 7a-(2,6-dioxopiperidin-3-yl)-3ah-isoindole-1,3-dione Chemical class C1=CC=CC2C(=O)NC(=O)C21C1CCC(=O)NC1=O FPNJYPLJTAYAMP-UHFFFAOYSA-N 0.000 title abstract description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 title 1
- 241000124008 Mammalia Species 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- -1 and 29 - methyl Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- WLUIQUZGNPAKRL-UHFFFAOYSA-N 3-(6-amino-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C2=CC(N)=CC=C2C(=O)N1C1CCC(=O)NC1=O WLUIQUZGNPAKRL-UHFFFAOYSA-N 0.000 claims description 15
- ACMVMVHUTTZSBR-UHFFFAOYSA-N 3-(4,5,6,7-tetrafluoro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(F)C(F)=C(F)C(F)=C2CN1C1CCC(=O)NC1=O ACMVMVHUTTZSBR-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- IICWMVJMJVXCLY-UHFFFAOYSA-N 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC(N)=CC=C2C(=O)N1C1CCC(=O)NC1=O IICWMVJMJVXCLY-UHFFFAOYSA-N 0.000 claims description 4
- LAGNQECGHYBSCQ-UHFFFAOYSA-N 3-(5-amino-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=CC(N)=CC=C2CN1C1CCC(=O)NC1=O LAGNQECGHYBSCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims description 3
- HKEZQPMXDKBNJN-UHFFFAOYSA-N 3-(4,5,6,7-tetrachloro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2CN1C1CCC(=O)NC1=O HKEZQPMXDKBNJN-UHFFFAOYSA-N 0.000 claims description 2
- VEEGBANOMRHUOB-UHFFFAOYSA-N 3-(4,5,6,7-tetramethoxy-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(OC)C(OC)=C(OC)C(OC)=C2CN1C1CCC(=O)NC1=O VEEGBANOMRHUOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000005588 protonation Effects 0.000 claims description 2
- XKAYAFBLGLCWSY-UHFFFAOYSA-N 3-(4-amino-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C=2C(N)=CC=CC=2CN1C1CCC(=O)NC1=O XKAYAFBLGLCWSY-UHFFFAOYSA-N 0.000 claims 2
- RFEZFLDQHUMVOF-UHFFFAOYSA-N 3-(4,5,6,7-tetramethyl-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(C)C(C)=C(C)C(C)=C2CN1C1CCC(=O)NC1=O RFEZFLDQHUMVOF-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- WENKGSGGXGQHSH-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical class C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O WENKGSGGXGQHSH-UHFFFAOYSA-N 0.000 abstract description 3
- VZTDWPXKIYLLAT-UHFFFAOYSA-N 4-amino-2-(3-methyl-2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC(N)=C2C(=O)N1C1(C)CCC(=O)NC1=O VZTDWPXKIYLLAT-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- 239000000203 mixture Substances 0.000 description 64
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 50
- 239000007787 solid Substances 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000003826 tablet Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 28
- 239000008101 lactose Substances 0.000 description 28
- 229920002472 Starch Polymers 0.000 description 25
- 235000019359 magnesium stearate Nutrition 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 239000008107 starch Substances 0.000 description 19
- 235000019698 starch Nutrition 0.000 description 19
- 239000000454 talc Substances 0.000 description 19
- 229910052623 talc Inorganic materials 0.000 description 19
- 235000012222 talc Nutrition 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 241000725303 Human immunodeficiency virus Species 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 239000008187 granular material Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 108010010803 Gelatin Proteins 0.000 description 11
- 229920000159 gelatin Polymers 0.000 description 11
- 239000008273 gelatin Substances 0.000 description 11
- 235000019322 gelatine Nutrition 0.000 description 11
- 235000011852 gelatine desserts Nutrition 0.000 description 11
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 229930195725 Mannitol Natural products 0.000 description 10
- 210000001744 T-lymphocyte Anatomy 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 239000000594 mannitol Substances 0.000 description 10
- 235000010355 mannitol Nutrition 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 230000004913 activation Effects 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000002828 nitro derivatives Chemical class 0.000 description 9
- 241000700605 Viruses Species 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 7
- 239000008108 microcrystalline cellulose Substances 0.000 description 7
- 229940016286 microcrystalline cellulose Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 208000030507 AIDS Diseases 0.000 description 6
- 108090000695 Cytokines Proteins 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 6
- 208000031886 HIV Infections Diseases 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 210000002540 macrophage Anatomy 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 6
- 230000010076 replication Effects 0.000 description 6
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 6
- 229940081974 saccharin Drugs 0.000 description 6
- 235000019204 saccharin Nutrition 0.000 description 6
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 6
- 239000008117 stearic acid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 229940100445 wheat starch Drugs 0.000 description 6
- YCPULGHBTPQLRH-UHFFFAOYSA-N 3-aminopiperidine-2,6-dione;hydron;chloride Chemical compound Cl.NC1CCC(=O)NC1=O YCPULGHBTPQLRH-UHFFFAOYSA-N 0.000 description 5
- 102000004127 Cytokines Human genes 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- FCGIVHSBEKGQMZ-UHFFFAOYSA-N methyl 2-(bromomethyl)-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1CBr FCGIVHSBEKGQMZ-UHFFFAOYSA-N 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- 238000013518 transcription Methods 0.000 description 5
- 230000035897 transcription Effects 0.000 description 5
- KDHAQQFLGBZQCF-UHFFFAOYSA-N 3-methyl-3-(4,5,6,7-tetrafluoro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C(C(=C(F)C(F)=C2F)F)=C2C(=O)N1C1(C)CCC(=O)NC1=O KDHAQQFLGBZQCF-UHFFFAOYSA-N 0.000 description 4
- 208000037357 HIV infectious disease Diseases 0.000 description 4
- 206010040070 Septic Shock Diseases 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 208000006386 Bone Resorption Diseases 0.000 description 3
- 206010006895 Cachexia Diseases 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 208000011231 Crohn disease Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 208000036142 Viral infection Diseases 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 230000024279 bone resorption Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 239000007910 chewable tablet Substances 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 102000034356 gene-regulatory proteins Human genes 0.000 description 3
- 108091006104 gene-regulatory proteins Proteins 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 201000004792 malaria Diseases 0.000 description 3
- 210000001616 monocyte Anatomy 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 230000029812 viral genome replication Effects 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KVRCAGKHAZRSQX-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)N1C1CCC(=O)NC1=O KVRCAGKHAZRSQX-UHFFFAOYSA-N 0.000 description 2
- ZTCQBIQDDCLBGN-UHFFFAOYSA-N 2-[5-(5-amino-1,3-dioxo-7ah-isoindol-3a-yl)-2-oxopiperidin-1-yl]acetaldehyde Chemical compound O=C1NC(=O)C2C=CC(N)=CC12C1CCC(=O)N(CC=O)C1 ZTCQBIQDDCLBGN-UHFFFAOYSA-N 0.000 description 2
- CSPWBOBHCQNLLW-UHFFFAOYSA-N 3-(6-nitro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C2=CC([N+](=O)[O-])=CC=C2C(=O)N1C1CCC(=O)NC1=O CSPWBOBHCQNLLW-UHFFFAOYSA-N 0.000 description 2
- JKPJLYIGKKDZDT-UHFFFAOYSA-N 3-(7-nitro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)N1C1CCC(=O)NC1=O JKPJLYIGKKDZDT-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 2
- QQIAZNQWBNCCLS-UHFFFAOYSA-N 6-amino-7a-(3-methyl-2,6-dioxopiperidin-3-yl)-3ah-isoindole-1,3-dione Chemical compound C1=C(N)C=CC(C(=O)NC2=O)C12C1(C)CCC(=O)NC1=O QQIAZNQWBNCCLS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 241000701022 Cytomegalovirus Species 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- 206010014824 Endotoxic shock Diseases 0.000 description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 206010024229 Leprosy Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- 201000010001 Silicosis Diseases 0.000 description 2
- 230000006044 T cell activation Effects 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000033115 angiogenesis Effects 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003915 cell function Effects 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 2
- 210000000805 cytoplasm Anatomy 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 230000007302 negative regulation of cytokine production Effects 0.000 description 2
- 231100000590 oncogenic Toxicity 0.000 description 2
- 230000002246 oncogenic effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002947 procoagulating effect Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 102000003390 tumor necrosis factor Human genes 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- WJXSIJUIBOTFHQ-LSCFUAHRSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(4-fluorophenyl)ethoxy]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1OCCC1=CC=C(F)C=C1 WJXSIJUIBOTFHQ-LSCFUAHRSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- CCXSGQZMYLXTOI-UHFFFAOYSA-N 13506-76-8 Chemical class CC1=CC=CC([N+]([O-])=O)=C1C(O)=O CCXSGQZMYLXTOI-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- MYPNWKPZEHVONN-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-5-nitroisoindole-1,3-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)N1C1CCC(=O)NC1=O MYPNWKPZEHVONN-UHFFFAOYSA-N 0.000 description 1
- SSFKURSGJRBEPO-UHFFFAOYSA-N 2-(3-methyl-2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)N1C1(C)CCC(=O)NC1=O SSFKURSGJRBEPO-UHFFFAOYSA-N 0.000 description 1
- QSLMPDKYTNEMFQ-UHFFFAOYSA-N 2-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CBr QSLMPDKYTNEMFQ-UHFFFAOYSA-N 0.000 description 1
- XXIALTSAXCJAST-UHFFFAOYSA-N 2-aminopentanediamide;hydron;chloride Chemical compound Cl.NC(=O)C(N)CCC(N)=O XXIALTSAXCJAST-UHFFFAOYSA-N 0.000 description 1
- MFXUHBWEUJSJAU-UHFFFAOYSA-N 2-methylpentanediamide Chemical compound NC(=O)C(C)CCC(N)=O MFXUHBWEUJSJAU-UHFFFAOYSA-N 0.000 description 1
- QXMIBFXPGQHNCP-UHFFFAOYSA-N 3-(4-nitro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2CN1C1CCC(=O)NC1=O QXMIBFXPGQHNCP-UHFFFAOYSA-N 0.000 description 1
- XUHHLYHISZFASD-UHFFFAOYSA-N 3-(5-nitro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2CN1C1CCC(=O)NC1=O XUHHLYHISZFASD-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- BONIIQYTWOPUQI-UHFFFAOYSA-N 4-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)NC2=O BONIIQYTWOPUQI-UHFFFAOYSA-N 0.000 description 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000173529 Aconitum napellus Species 0.000 description 1
- 206010048998 Acute phase reaction Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000033116 Asbestos intoxication Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 241001211977 Bida Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 108010067225 Cell Adhesion Molecules Proteins 0.000 description 1
- 102000016289 Cell Adhesion Molecules Human genes 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010010755 Conjunctivitis viral Diseases 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102100038591 Endothelial cell-selective adhesion molecule Human genes 0.000 description 1
- 208000037487 Endotoxemia Diseases 0.000 description 1
- 241000713730 Equine infectious anemia virus Species 0.000 description 1
- 241000713800 Feline immunodeficiency virus Species 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VVOPSEUXHSUTJS-LURJTMIESA-N Glutamine t-butyl ester Chemical compound CC(C)(C)OC(=O)[C@@H](N)CCC(N)=O VVOPSEUXHSUTJS-LURJTMIESA-N 0.000 description 1
- 206010018498 Goitre Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020164 HIV infection CDC Group III Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 101000882622 Homo sapiens Endothelial cell-selective adhesion molecule Proteins 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- 241000713666 Lentivirus Species 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010062207 Mycobacterial infection Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108700005075 Regulator Genes Proteins 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102100026966 Thrombomodulin Human genes 0.000 description 1
- 108010079274 Thrombomodulin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 208000005914 Viral Conjunctivitis Diseases 0.000 description 1
- 102100029477 Vitamin K-dependent protein C Human genes 0.000 description 1
- 101710193900 Vitamin K-dependent protein C Proteins 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229940023019 aconite Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 210000001132 alveolar macrophage Anatomy 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SCJNCDSAIRBRIA-DOFZRALJSA-N arachidonyl-2'-chloroethylamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCCl SCJNCDSAIRBRIA-DOFZRALJSA-N 0.000 description 1
- 206010003441 asbestosis Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 208000019664 bone resorption disease Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000003711 chorioallantoic membrane Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000005796 circulatory shock Effects 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 230000009791 fibrotic reaction Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000002518 glial effect Effects 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 208000030915 hypercalcemia disease Diseases 0.000 description 1
- 230000000222 hyperoxic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- PGNKFDOPHHNVNF-UHFFFAOYSA-N methyl 2-(bromomethyl)-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1CBr PGNKFDOPHHNVNF-UHFFFAOYSA-N 0.000 description 1
- OAEABYNRBPCSQB-UHFFFAOYSA-N methyl 2-(bromomethyl)-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1CBr OAEABYNRBPCSQB-UHFFFAOYSA-N 0.000 description 1
- CRZGFIMLHZTLGT-UHFFFAOYSA-N methyl 2-methyl-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1C CRZGFIMLHZTLGT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 210000002864 mononuclear phagocyte Anatomy 0.000 description 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 210000002997 osteoclast Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000009518 penetrating injury Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-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
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000004983 pleiotropic effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 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
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical class CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ZEPNUNKDKQACNC-RGMNGODLSA-N tert-butyl (2s)-2,5-diamino-5-oxopentanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)[C@@H](N)CCC(N)=O ZEPNUNKDKQACNC-RGMNGODLSA-N 0.000 description 1
- 229940124597 therapeutic agent 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
- 238000002054 transplantation Methods 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Hospice & Palliative Care (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08690258 US5635517B1 (en) | 1996-07-24 | 1996-07-24 | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
| US08/701,494 US5798368A (en) | 1996-08-22 | 1996-08-22 | Tetrasubstituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines and method of reducing TNFα levels |
| US4827897P | 1997-05-30 | 1997-05-30 | |
| PCT/US1997/013375 WO1998003502A1 (en) | 1996-07-24 | 1997-07-24 | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and method of reducing tnf-alpha levels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA60308C2 true UA60308C2 (uk) | 2003-10-15 |
Family
ID=27367302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA99010371A UA60308C2 (uk) | 1996-07-24 | 1997-07-24 | ЗАМІЩЕНІ 2-(2,6-ДІОКСОПІПЕРИДИН-3-ІЛ)ФТАЛІМІДИ ТА 1-ОКСОІЗОІНДОЛІНИ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЗНИЖЕННЯ РІВНЯ ФПН-α |
Country Status (21)
| Country | Link |
|---|---|
| EP (4) | EP0925294B3 (enExample) |
| JP (1) | JP4065567B2 (enExample) |
| KR (2) | KR20050032629A (enExample) |
| CN (1) | CN1117089C (enExample) |
| AT (4) | ATE530542T1 (enExample) |
| CA (3) | CA2624949C (enExample) |
| CZ (3) | CZ304569B6 (enExample) |
| DE (4) | DE69717831T3 (enExample) |
| DK (2) | DK0925294T6 (enExample) |
| ES (4) | ES2187805T7 (enExample) |
| FI (1) | FI120687B (enExample) |
| FR (1) | FR07C0056I2 (enExample) |
| HU (1) | HUS1300056I1 (enExample) |
| LU (1) | LU91359I2 (enExample) |
| NL (1) | NL300291I2 (enExample) |
| NZ (1) | NZ333903A (enExample) |
| PL (2) | PL195916B1 (enExample) |
| PT (4) | PT2177517E (enExample) |
| SK (1) | SK9199A3 (enExample) |
| UA (1) | UA60308C2 (enExample) |
| WO (1) | WO1998003502A1 (enExample) |
Families Citing this family (206)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228879B1 (en) | 1997-10-16 | 2001-05-08 | The Children's Medical Center | Methods and compositions for inhibition of angiogenesis |
| US6429221B1 (en) | 1994-12-30 | 2002-08-06 | Celgene Corporation | Substituted imides |
| HU228769B1 (en) * | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
| PL195916B1 (pl) * | 1996-07-24 | 2007-11-30 | Celgene Corp | Izomery optyczne podstawionej 1-okso-izoindoliny i 1,3-diokso-izoindoliny, kompozycje farmaceutyczne je zawierające oraz ich zastosowanie |
| US5635517B1 (en) | 1996-07-24 | 1999-06-29 | Celgene Corp | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
| DE19703763C1 (de) * | 1997-02-01 | 1998-10-01 | Gruenenthal Gmbh | Thalidomidanaloge Verbindungen aus der Klasse der Piperidin-2,6-Dione |
| CZ299808B6 (cs) * | 1997-11-18 | 2008-12-03 | Celgene Corporation | Substituované 2-(2,6-dioxo-3-fluoropiperidin-3-yl)izoindoliny a jejich použití za úcelem snížení hladin TNFalfa |
| US5955476A (en) * | 1997-11-18 | 1999-09-21 | Celgene Corporation | Substituted 2-(2,6-dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing inflammatory cytokine levels |
| JP4695259B2 (ja) * | 1998-03-16 | 2011-06-08 | セルジーン コーポレイション | ２−（２，６−ジオキソピペリジン−３−イル）イソインドリン誘導体、その製剤および炎症性サイトカイン阻害剤としてのその使用 |
| AU771015B2 (en) | 1999-03-18 | 2004-03-11 | Celgene Corporation | Substituted 1-oxo- and 1,3-dioxoisoindolines and their use in pharmaceutical compositions for reducing inflammatory cytokine levels |
| DE19917195B4 (de) * | 1999-04-16 | 2006-09-28 | Immatics Biotechnologies Gmbh | Peptid zur Auslösung einer Immunreaktion gegen Tumorzellen, diese enthaltende pharmzeutische Zusammensetzungen, dessen Verwendungen, dafür codierende Nukleinsäure und diese Nukleinsäure enthaltender Expressionsvektor |
| US7629360B2 (en) | 1999-05-07 | 2009-12-08 | Celgene Corporation | Methods for the treatment of cachexia and graft v. host disease |
| US7182953B2 (en) * | 1999-12-15 | 2007-02-27 | Celgene Corporation | Methods and compositions for the prevention and treatment of atherosclerosis restenosis and related disorders |
| US6458810B1 (en) | 2000-11-14 | 2002-10-01 | George Muller | Pharmaceutically active isoindoline derivatives |
| JP4242651B2 (ja) * | 2000-11-30 | 2009-03-25 | ザ チルドレンズ メディカル センター コーポレイション | ４−アミノ−サリドマイドエナンチオマーの合成法 |
| CN1487935A (zh) * | 2000-12-11 | 2004-04-07 | ����ҩƷ��ҵ��ʽ���� | 改良型水溶性药物组合物 |
| US7091353B2 (en) | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| ES2338534T3 (es) * | 2001-02-27 | 2010-05-10 | The Governement Of The Usa, Represented By The Secretary Department Of Health And Human Services | Analogos de talidomina como inhibidores de la angiogenesis. |
| ES2325916T3 (es) * | 2001-08-06 | 2009-09-24 | The Children's Medical Center Corporation | Actividad antiangiogenica de analogos de talidomida sustituidos con nitrogeno. |
| US7498171B2 (en) | 2002-04-12 | 2009-03-03 | Anthrogenesis Corporation | Modulation of stem and progenitor cell differentiation, assays, and uses thereof |
| US7323479B2 (en) | 2002-05-17 | 2008-01-29 | Celgene Corporation | Methods for treatment and management of brain cancer using 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-methylisoindoline |
| USRE48890E1 (en) | 2002-05-17 | 2022-01-11 | Celgene Corporation | Methods for treating multiple myeloma with 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione after stem cell transplantation |
| US7968569B2 (en) | 2002-05-17 | 2011-06-28 | Celgene Corporation | Methods for treatment of multiple myeloma using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| US7393862B2 (en) | 2002-05-17 | 2008-07-01 | Celgene Corporation | Method using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for treatment of certain leukemias |
| CA2752140A1 (en) | 2002-05-17 | 2003-11-27 | Celgene Corporation | Methods and compositions using 3-(4-amino-1-oxo-1,3-dihydroisoindol-1-yl)-piperidine-2,6-dione for treatment and management of renal cancer |
| US8404717B2 (en) | 2002-10-15 | 2013-03-26 | Celgene Corporation | Methods of treating myelodysplastic syndromes using lenalidomide |
| EP1900369A1 (en) | 2002-10-15 | 2008-03-19 | Celgene Corporation | Methods of using and compositions comprising immunomodulatory compounds for the treatment and management of myelodysplastic syndromes |
| US11116782B2 (en) | 2002-10-15 | 2021-09-14 | Celgene Corporation | Methods of treating myelodysplastic syndromes with a combination therapy using lenalidomide and azacitidine |
| US7189740B2 (en) | 2002-10-15 | 2007-03-13 | Celgene Corporation | Methods of using 3-(4-amino-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myelodysplastic syndromes |
| US8404716B2 (en) | 2002-10-15 | 2013-03-26 | Celgene Corporation | Methods of treating myelodysplastic syndromes with a combination therapy using lenalidomide and azacitidine |
| FR2845994B1 (fr) * | 2002-10-18 | 2006-05-19 | Servier Lab | Nouveaux derives de benzo[e][1,4]oxazino[3,2-g]isoindole substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN1326522C (zh) * | 2002-10-24 | 2007-07-18 | 细胞基因公司 | 用于治疗、改变和控制疼痛的包含免疫调节化合物的组合物 |
| NZ540186A (en) * | 2002-10-31 | 2008-03-28 | Celgene Corp | Composition for the treatment of macular degeneration |
| US7563810B2 (en) | 2002-11-06 | 2009-07-21 | Celgene Corporation | Methods of using 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myeloproliferative diseases |
| CH696542A5 (de) * | 2003-07-09 | 2007-07-31 | Siegfried Ltd | Verfahren zur Herstellung von substituierten 2,6-Dioxopiperidin-3-yl-Verbindungen. |
| UA83504C2 (en) | 2003-09-04 | 2008-07-25 | Селджин Корпорейшн | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| US7973057B2 (en) | 2003-09-17 | 2011-07-05 | The United States Of America As Represented By The Department Of Health And Human Services | Thalidomide analogs |
| US8952895B2 (en) | 2011-06-03 | 2015-02-10 | Apple Inc. | Motion-based device operations |
| US7612096B2 (en) | 2003-10-23 | 2009-11-03 | Celgene Corporation | Methods for treatment, modification and management of radiculopathy using 1-oxo-2-(2,6-dioxopiperidin-3yl)-4-aminoisoindoline |
| US20050100529A1 (en) * | 2003-11-06 | 2005-05-12 | Zeldis Jerome B. | Methods of using and compositions comprising immunomodulatory compounds for the treatment and management of asbestos-related diseases and disorders |
| KR101224262B1 (ko) | 2004-03-22 | 2013-01-21 | 셀진 코포레이션 | 면역조절 화합물을 포함하는 피부 질환 또는 장애의 치료및 관리용 조성물 및 이의 사용 방법 |
| CN1984657B (zh) * | 2004-05-05 | 2010-12-15 | 细胞基因公司 | 用于治疗和控制骨髓增生性疾病的包含免疫调节化合物的组合物和使用方法 |
| EP2479172B1 (en) | 2004-09-03 | 2013-10-09 | Celgene Corporation | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines |
| CA2612612C (en) | 2005-06-30 | 2014-03-11 | Celgene Corporation | Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds |
| US7928280B2 (en) | 2005-07-13 | 2011-04-19 | Anthrogenesis Corporation | Treatment of leg ulcers using placenta derived collagen biofabric |
| BRPI0614995A2 (pt) | 2005-08-31 | 2010-01-12 | Celgene Corp | composto ou um sal, solvato ou estereoisemero farmaceuticamente aceitável do mesmo, composição farmacêutica, uso de uma quantidade terapêutica ou profilaticamente eficaz de um composto ou um sal, solvato ou estereoisemero farmaceuticamente aceitável do mesmo, e, forma de dosagem unitária única |
| EP1928492B1 (en) | 2005-09-01 | 2011-02-23 | Celgene Corporation | Immunological uses of immunodulatory compounds for vaccine and anti-infections disease therapy |
| US20070066512A1 (en) | 2005-09-12 | 2007-03-22 | Dominique Verhelle | Methods and compositions using immunomodulatory compounds for the treatment of disorders associated with low plasma leptin levels |
| CN1939922B (zh) * | 2005-09-27 | 2010-10-13 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的5H-噻吩[3，4-c]吡咯-4，6-二酮衍生物 |
| CA2633980A1 (en) | 2005-12-29 | 2007-07-12 | Anthrogenesis Corporation | Improved composition for collecting and preserving placental stem cells and methods of using the composition |
| WO2007106884A2 (en) | 2006-03-15 | 2007-09-20 | Theralogics, Inc. | Methods of treating muscular wasting diseases using nf-kb activation inhibitors |
| WO2007136640A2 (en) * | 2006-05-16 | 2007-11-29 | Celgene Corporation | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione |
| CL2007002218A1 (es) | 2006-08-03 | 2008-03-14 | Celgene Corp Soc Organizada Ba | Uso de 3-(4-amino-1-oxo-1,3-dihidro-isoindol-2-il)-piperidina 2,6-diona para la preparacion de un medicamento util para el tratamiento de linfoma de celula de capa. |
| US8105634B2 (en) | 2006-08-15 | 2012-01-31 | Anthrogenesis Corporation | Umbilical cord biomaterial for medical use |
| CL2007002513A1 (es) * | 2006-08-30 | 2008-04-04 | Celgene Corp Soc Organizada Ba | Compuestos derivados de isoindolina sustituidos, compuestos intermediarios; composicion farmaceutica; y uso en el tratamiento y prevencion de enfermedades tales como cancer, dolor, degeneracion macular, entre otras. |
| US8877780B2 (en) | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| CN102898416A (zh) | 2006-09-26 | 2013-01-30 | 细胞基因公司 | 作为抗肿瘤剂的5-取代的喹唑酮衍生物 |
| EP1923053A1 (en) | 2006-09-27 | 2008-05-21 | Novartis AG | Pharmaceutical compositions comprising nilotinib or its salt |
| WO2008060377A2 (en) | 2006-10-04 | 2008-05-22 | Anthrogenesis Corporation | Placental or umbilical cord tissue compositions |
| EP2076279B1 (en) | 2006-10-06 | 2014-08-27 | Anthrogenesis Corporation | Native (telopeptide) placental collagen compositions |
| KR101593242B1 (ko) | 2007-09-26 | 2016-02-11 | 셀진 코포레이션 | ６-, ７- 또는 ８-치환된 퀴나졸리논 유도체, 및 그를 포함하는 조성물 및 그의 사용 방법 |
| AU2008307633C1 (en) | 2007-09-28 | 2015-04-30 | Celularity Inc. | Tumor suppression using human placental perfusate and human placenta-derived intermediate natural killer cells |
| US20090088393A1 (en) * | 2007-09-28 | 2009-04-02 | Zomanex, Llc | Methods and formulations for converting intravenous and injectable drugs into oral dosage forms |
| CN101909609A (zh) * | 2007-11-08 | 2010-12-08 | 细胞基因公司 | 免疫调节化合物在治疗与内皮功能障碍有关的紊乱中的用途 |
| WO2009085234A2 (en) | 2007-12-20 | 2009-07-09 | Signal Pharmaceuticals, Inc. | Use of micro-rna as a biomarker of immunomodulatory drug activity |
| AU2009223014A1 (en) * | 2008-03-11 | 2009-09-17 | Dr. Reddy's Laboratories Ltd. | Preparation of lenalidomide |
| WO2009111948A1 (zh) * | 2008-03-13 | 2009-09-17 | 天津和美生物技术有限公司 | 3-(4-氨基-1-氧代-1,3-二氢异吲哚-2-基)哌啶-2,6-二酮及其衍生物的盐或盐的多晶型物及其制备和应用 |
| US20110060010A1 (en) * | 2008-03-13 | 2011-03-10 | Tianjin Hemay Bio-Tech Co., Ltd | Salts of 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione and derivatives thereof, or polymorphs of salts, process for preparing same and use thereof |
| US20090298882A1 (en) * | 2008-05-13 | 2009-12-03 | Muller George W | Thioxoisoindoline compounds and compositions comprising and methods of using the same |
| PE20140963A1 (es) | 2008-10-29 | 2014-08-06 | Celgene Corp | Compuestos de isoindolina para el tratamiento de cancer |
| US9045453B2 (en) | 2008-11-14 | 2015-06-02 | Concert Pharmaceuticals, Inc. | Substituted dioxopiperidinyl phthalimide derivatives |
| MX2011005112A (es) * | 2008-11-14 | 2011-06-16 | Concert Pharmaceuticals Inc | Derivados de dioxopiperidinil-ftalimida sustituida. |
| DE102008057335A1 (de) | 2008-11-14 | 2010-05-20 | Ratiopharm Gmbh | Amorphes Lenalidomid |
| DE102008057284A1 (de) | 2008-11-14 | 2010-05-20 | Ratiopharm Gmbh | Tabletten enthaltend Lenalidomid und Adhäsionsverstärker |
| DE102008057285A1 (de) | 2008-11-14 | 2010-05-20 | Ratiopharm Gmbh | 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidindion in Form einer festen Lösung |
| EP2396312A1 (en) | 2009-02-11 | 2011-12-21 | Celgene Corporation | Isotopologues of lenalidomide |
| ES2713524T3 (es) | 2009-03-25 | 2019-05-22 | Celularity Inc | Supresión tumoral usando linfocitos citolíticos naturales intermedios obtenidos a partir de placenta humana y compuestos inmunomoduladores |
| DK2391355T3 (en) | 2009-05-19 | 2017-02-27 | Celgene Corp | FORMULATIONS OF 4-AMINO-2- (2,6-DIOXOPIPERIDIN-3-YL) ISOINDOLIN-1,3-DION |
| US20120134969A1 (en) | 2009-05-25 | 2012-05-31 | Hiroshi Handa | Pharmaceutical composition containing nuclear factor involved in proliferation and differentiation of central neuronal cells |
| CN101580501B (zh) | 2009-06-01 | 2011-03-09 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮的合成方法及其中间体 |
| US20120184746A1 (en) | 2009-09-03 | 2012-07-19 | Ranbaxy Laboratories Limited | Process for the preparation of lenalidomide |
| WO2011050962A1 (en) | 2009-10-29 | 2011-05-05 | Ratiopharm Gmbh | Acid addition salts of lenalidomide |
| CN101696205B (zh) | 2009-11-02 | 2011-10-19 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物 |
| CN102127054B (zh) * | 2009-11-02 | 2013-04-03 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物 |
| WO2011069608A1 (en) | 2009-12-09 | 2011-06-16 | Ratiopharm Gmbh | S-lenalidomide, polymorphic forms thereof and blend comprising s- und r-lenalidomide |
| BR112012015129A2 (pt) | 2009-12-22 | 2019-09-24 | Celgene Corp | "composto, composição farmacêutica e método para tratar, controlar ou prevenir uma doença ou distúrbio" |
| EP2521543B1 (en) | 2010-01-05 | 2016-04-13 | Celgene Corporation | A combination of an immunomodulatory compound and an artemisinin derivative for treating cancer |
| SG10201501062SA (en) | 2010-02-11 | 2015-04-29 | Celgene Corp | Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the same |
| US9408831B2 (en) | 2010-04-07 | 2016-08-09 | Celgene Corporation | Methods for treating respiratory viral infection |
| WO2012078492A1 (en) | 2010-12-06 | 2012-06-14 | Celgene Corporation | A combination therapy with lenalidomide and a cdk inhibitor for treating multiple myeloma |
| CN103402980B (zh) | 2011-01-10 | 2016-06-29 | 细胞基因公司 | 作为pde4和/或细胞因子抑制剂的苯乙基砜异吲哚啉衍生物 |
| EA026100B1 (ru) | 2011-03-11 | 2017-03-31 | Селджин Корпорейшн | Твердые формы 3-(5-амино-2-метил-4-оксо-4н-хиназолин-3-ил)пиперидин-2,6-диона и их фармацевтические композиции и применение |
| AU2012236655B2 (en) | 2011-03-28 | 2016-09-22 | Deuterx, Llc, | 2',6'-dioxo-3'-deutero-piperdin-3-yl-isoindoline compounds |
| MX2013012083A (es) | 2011-04-18 | 2014-04-16 | Celgene Corp | Biomarcadores para el tratamiento de mieloma multiple. |
| CN103688176A (zh) | 2011-04-29 | 2014-03-26 | 细胞基因公司 | 利用cereblon作为预报因子治疗癌和炎性疾病的方法 |
| US20140221427A1 (en) | 2011-06-22 | 2014-08-07 | Celgene Corporation | Isotopologues of pomalidomide |
| PH12014500593A1 (en) | 2011-09-14 | 2019-09-02 | Celgene Corp | Formulations of cyclopropanecarboxylic acid {2-(1s)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1h-isoindol-4-yl}-amidecelgene corporation state of incorporation:delaware |
| US8927725B2 (en) | 2011-12-02 | 2015-01-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thio compounds |
| SG10201605251VA (en) | 2011-12-27 | 2016-08-30 | Celgene Corp | Formulations of (+)-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-4-acetylaminoisoindoline-1,3-dione |
| ES2671608T3 (es) * | 2012-02-21 | 2018-06-07 | Celgene Corporation | Formas sólidas de 3-(4-nitro-1-oxoisoindolin-2-il)piperidina-2,6-diona |
| WO2013182662A1 (en) | 2012-06-06 | 2013-12-12 | Bionor Immuno As | Vaccine |
| ES2872967T3 (es) | 2012-06-29 | 2021-11-03 | Celgene Corp | Métodos para determinar la eficacia de fármacos usando IKZF3 (AIOLOS) |
| PE20150617A1 (es) | 2012-08-09 | 2015-05-21 | Celgene Corp | Formas solidas de 3-(4-((4-(morfolinometil)bencil)oxi)-1-oxoisoindolin-2-il)piperidin-2,6-diona o un estereoisomero del mismo, de sus sales, y composiciones que comprenden las mismas |
| US9587281B2 (en) | 2012-08-14 | 2017-03-07 | Celgene Corporation | Cereblon isoforms and their use as biomarkers for therapeutic treatment |
| WO2014066243A1 (en) | 2012-10-22 | 2014-05-01 | Concert Pharmaceuticals, Inc. | Solid forms of {s-3-(4-amino-1-oxo-isoindolin-2yl)(piperidine-3,4,4,5,5-d5)-2,6-dione} |
| AU2013204922B2 (en) | 2012-12-20 | 2015-05-14 | Celgene Corporation | Chimeric antigen receptors |
| FR2999914B1 (fr) * | 2012-12-21 | 2015-08-07 | Oreal | Utilisation de derives de l'acide imidocarboxylique pour traiter les alterations de la peau liees a l'age ou au photovieillissement |
| FR2999915B1 (fr) * | 2012-12-21 | 2017-08-11 | Oreal | Utilisation de derives de l'acide imidocarboxylique en tant qu'agent apaisant |
| WO2014110322A2 (en) | 2013-01-11 | 2014-07-17 | Concert Pharmaceuticals, Inc. | Substituted dioxopiperidinyl phthalimide derivatives |
| CA2935495C (en) | 2013-01-14 | 2021-04-20 | Deuterx, Llc | 3-(5-substituted-4-oxoquinazolin-3(4h)-yl)-3-deutero-piperidine-2,6-dione derivatives |
| WO2014123879A1 (en) | 2013-02-05 | 2014-08-14 | Anthrogenesis Corporation | Natural killer cells from placenta |
| EP2764866A1 (en) | 2013-02-07 | 2014-08-13 | IP Gesellschaft für Management mbH | Inhibitors of nedd8-activating enzyme |
| CN105518018B (zh) | 2013-03-15 | 2020-04-03 | 细胞基因公司 | 修饰的t淋巴细胞 |
| CN104072476B (zh) * | 2013-03-27 | 2018-08-21 | 江苏豪森药业集团有限公司 | 泊马度胺晶型及其制备方法和用途 |
| TW201526897A (zh) | 2013-04-17 | 2015-07-16 | Signal Pharm Llc | 使用ｔｏｒ激酶抑制劑組合療法以治療癌症之方法 |
| EP2815749A1 (en) * | 2013-06-20 | 2014-12-24 | IP Gesellschaft für Management mbH | Solid form of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione having specified X-ray diffraction pattern |
| WO2015007337A1 (en) | 2013-07-19 | 2015-01-22 | Bionor Immuno As | Method for the vaccination against hiv |
| CN103497174B (zh) * | 2013-07-29 | 2015-10-28 | 杭州派臣医药科技有限公司 | 泊利度胺的制备和精制方法 |
| CN107188884A (zh) * | 2013-10-29 | 2017-09-22 | 上海医药工业研究院 | 一种泊利度胺的纯化方法 |
| CN104557858B (zh) * | 2013-10-29 | 2018-06-01 | 上海医药工业研究院 | 一种泊利度胺的制备方法 |
| CN105939716A (zh) | 2013-12-03 | 2016-09-14 | 埃斯泰隆制药公司 | 组蛋白脱乙酰基酶抑制剂和免疫调节药物的组合 |
| CN104016967A (zh) * | 2014-04-04 | 2014-09-03 | 南京工业大学 | 一种泊利度胺的合成方法 |
| KR20250127179A (ko) * | 2014-04-14 | 2025-08-26 | 아비나스 오퍼레이션스, 인코포레이티드 | 단백질분해의 이미드-기초된 조절인자 및 연관된 이용 방법 |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| JP6640126B2 (ja) | 2014-06-27 | 2020-02-05 | セルジーン コーポレイション | セレブロン及び他のｅ３ユビキチンリガーゼの立体構造の変化を誘導するための組成物及び方法 |
| CN105348257A (zh) * | 2014-08-20 | 2016-02-24 | 河北菲尼斯生物技术有限公司 | 泊马度胺的制备方法 |
| LT3182996T (lt) | 2014-08-22 | 2023-03-10 | Celgene Corporation | Daugybinės mielomos gydymo būdai imunomoduliuojančiais junginiais derinyje su antikūnais |
| CN105440013B (zh) * | 2014-08-29 | 2018-10-09 | 杭州和泽医药科技有限公司 | 一种泊马度胺的制备方法 |
| ES2812877T3 (es) * | 2014-10-30 | 2021-03-18 | Kangpu Biopharmaceuticals Ltd | Derivado de isoindolina, producto intermedio, método de preparación, composición farmacéutica y uso del mismo |
| WO2016097030A1 (en) | 2014-12-19 | 2016-06-23 | Synthon B.V. | Pharmaceutical composition comprising amorphous lenalidomide |
| US10471156B2 (en) | 2014-12-19 | 2019-11-12 | Synthon B.V. | Pharmaceutical composition comprising amorphous lenalidomide |
| CN104447689B (zh) * | 2014-12-22 | 2016-07-20 | 上海迈柏医药科技有限公司 | 来那度胺的晶型及其制备方法 |
| US12312316B2 (en) | 2015-01-20 | 2025-05-27 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| US11352351B2 (en) | 2015-01-20 | 2022-06-07 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| RU2694895C2 (ru) * | 2015-05-22 | 2019-07-18 | Биотерикс, Инк. | Нацеленные на белки соединения, их композиции, способы и применения |
| WO2016197114A1 (en) | 2015-06-05 | 2016-12-08 | Arvinas, Inc. | Tank-binding kinase-1 protacs and associated methods of use |
| EP3313818B1 (en) | 2015-06-26 | 2023-11-08 | Celgene Corporation | Methods for the treatment of kaposi's sarcoma or kshv-induced lymphoma using immunomodulatory compounds, and uses of biomarkers |
| US10772962B2 (en) | 2015-08-19 | 2020-09-15 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of bromodomain-containing proteins |
| AU2016378482A1 (en) | 2015-12-22 | 2018-07-12 | Synthon B.V. | Pharmaceutical composition comprising amorphous lenalidomide and an antioxidant |
| US10830762B2 (en) | 2015-12-28 | 2020-11-10 | Celgene Corporation | Compositions and methods for inducing conformational changes in cereblon and other E3 ubiquitin ligases |
| WO2017201069A1 (en) | 2016-05-18 | 2017-11-23 | Biotheryx, Inc. | Oxoindoline derivatives as protein function modulators |
| HUE070289T2 (hu) | 2016-10-11 | 2025-05-28 | Arvinas Operations Inc | Vegyületek és módszerek az androgénreceptor célzott lebontására |
| KR20230127371A (ko) | 2016-11-01 | 2023-08-31 | 아비나스 오퍼레이션스, 인코포레이티드 | 타우(Tau)-단백질 표적화 프로탁(PROTAC) 및 관련 사용 방법 |
| IL297717A (en) | 2016-12-01 | 2022-12-01 | Arvinas Operations Inc | History of tetrahydronaphthalene and tetrahydroisoquinoline as estrogen receptor antagonists |
| MA46961A (fr) | 2016-12-03 | 2019-10-09 | Juno Therapeutics Inc | Procédés de modulation de lymphocytes t modifiés par car |
| KR102368555B1 (ko) | 2016-12-16 | 2022-02-28 | 강푸 바이오파마슈티칼즈 리미티드 | 조성물, 이의 적용 및 치료 방법 |
| US11173211B2 (en) | 2016-12-23 | 2021-11-16 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of rapidly accelerated Fibrosarcoma polypeptides |
| WO2018118598A1 (en) | 2016-12-23 | 2018-06-28 | Arvinas, Inc. | Compounds and methods for the targeted degradation of fetal liver kinase polypeptides |
| MX2019007649A (es) | 2016-12-23 | 2019-09-10 | Arvinas Operations Inc | Compuestos y metodos para la degradacion dirigida de polipeptidos de fibrosarcoma acelerado rapidamente. |
| WO2018119441A1 (en) | 2016-12-23 | 2018-06-28 | Arvinas, Inc. | Egfr proteolysis targeting chimeric molecules and associated methods of use |
| US11191741B2 (en) | 2016-12-24 | 2021-12-07 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of enhancer of zeste homolog 2 polypeptide |
| IL300417A (en) | 2017-01-26 | 2023-04-01 | Arvinas Operations Inc | Bifunctional benzothiophene compounds, preparations containing them and their use in therapy |
| EP3577109A4 (en) | 2017-01-31 | 2020-11-18 | Arvinas Operations, Inc. | CEREMONY LIGANDS AND BIFUNCTIONAL COMPOUNDS CONTAINING THEM |
| US20200000776A1 (en) | 2017-02-13 | 2020-01-02 | Kangpu Biopharmaceuticals, Ltd. | Combination treating prostate cancer, pharmaceutical composition and treatment method |
| CA3061945A1 (en) | 2017-05-01 | 2018-11-08 | Juno Therapeutics, Inc. | Combination of a cell therapy and an immunomodulatory compound |
| US10093647B1 (en) | 2017-05-26 | 2018-10-09 | Celgene Corporation | Crystalline 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione dihydrate, compositions and methods of use thereof |
| KR20200054160A (ko) | 2017-06-02 | 2020-05-19 | 주노 쎄러퓨티크스 인코퍼레이티드 | 입양 세포 요법을 사용한 치료를 위한 물품 제조 및 방법 |
| AU2018291032A1 (en) | 2017-06-29 | 2020-01-16 | Juno Therapeutics, Inc. | Mouse model for assessing toxicities associated with immunotherapies |
| TWI793151B (zh) * | 2017-08-23 | 2023-02-21 | 瑞士商諾華公司 | 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途 |
| US10093648B1 (en) | 2017-09-22 | 2018-10-09 | Celgene Corporation | Crystalline 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione hemihydrate, compositions and methods of use thereof |
| US10093649B1 (en) | 2017-09-22 | 2018-10-09 | Celgene Corporation | Crystalline 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione monohydrate, compositions and methods of use thereof |
| CA3077325A1 (en) | 2017-09-28 | 2019-04-04 | Celularity Inc. | Tumor suppression using human placenta-derived intermediate natural killer (pink) cells in combination with an antibody |
| CA3080904A1 (en) | 2017-11-01 | 2019-05-09 | Juno Therapeutics, Inc. | Antibodies and chimeric antigen receptors specific for b-cell maturation antigen |
| WO2019089858A2 (en) | 2017-11-01 | 2019-05-09 | Juno Therapeutics, Inc. | Methods of assessing or monitoring a response to a cell therapy |
| US11065231B2 (en) | 2017-11-17 | 2021-07-20 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of interleukin-1 receptor- associated kinase 4 polypeptides |
| WO2019118937A1 (en) | 2017-12-15 | 2019-06-20 | Juno Therapeutics, Inc. | Anti-cct5 binding molecules and methods of use thereof |
| EP3505158A1 (en) | 2017-12-27 | 2019-07-03 | KRKA, d.d., Novo mesto | Pharmaceutical composition of lenalidomide pharmaceutically acceptable acid addition salt |
| US11452722B2 (en) | 2018-01-11 | 2022-09-27 | Natco Pharma Limited | Stable pharmaceutical compositions comprising lenalidomide |
| EP3743066A4 (en) | 2018-01-26 | 2021-09-08 | Yale University | IMIDE-BASED PROTEOLYSIS MODULATORS AND RELATED METHODS OF USE |
| MX2020008718A (es) | 2018-02-21 | 2020-12-07 | Celgene Corp | Anticuerpos de union a bcma y usos de los mismos. |
| EP3545949A1 (en) | 2018-03-29 | 2019-10-02 | Midas Pharma GmbH | Oral dosage forms comprising pomalidomide crystalline form a |
| JP7720698B2 (ja) | 2018-04-04 | 2025-08-08 | アルビナス・オペレーションズ・インコーポレイテッド | タンパク質分解の調節因子および関連する使用方法 |
| KR102286499B1 (ko) | 2018-04-13 | 2021-08-05 | 주식회사 삼양홀딩스 | 레날리도마이드를 포함하는 약제학적 조성물 |
| KR102259798B1 (ko) | 2018-04-13 | 2021-06-02 | 주식회사 삼양홀딩스 | 붕해가 개선된 레날리도마이드의 경구용 정제 조성물 |
| KR102286500B1 (ko) | 2018-04-13 | 2021-08-05 | 주식회사 삼양홀딩스 | 레날리도마이드를 포함하는 경구용 고형제제의 제조방법 |
| KR102286498B1 (ko) | 2018-04-13 | 2021-08-05 | 주식회사 삼양홀딩스 | 레날리도마이드의 경구용 코팅 정제 조성물 |
| JP2021518424A (ja) | 2018-04-13 | 2021-08-02 | サムヤン バイオファーマシューティカルズ コーポレイションＳａｍｙａｎｇ Ｂｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｃｏｒｐｏｒａｔｉｏｎ | 様々な用量のレナリドミドの経口用錠剤組成物 |
| CN112912376A (zh) | 2018-08-20 | 2021-06-04 | 阿尔维纳斯运营股份有限公司 | 用于治疗神经变性疾病的具有E3泛素连接酶结合活性并靶向α-突触核蛋白的蛋白水解靶向嵌合(PROTAC)化合物 |
| MX2021005366A (es) | 2018-11-08 | 2021-09-10 | Juno Therapeutics Inc | Metodos y combinaciones para el tratamiento y modulacion de celulas t. |
| CA3120118A1 (en) | 2018-11-16 | 2020-05-22 | Juno Therapeutics, Inc. | Methods of dosing engineered t cells for the treatment of b cell malignancies |
| WO2020113194A2 (en) | 2018-11-30 | 2020-06-04 | Juno Therapeutics, Inc. | Methods for treatment using adoptive cell therapy |
| EP3891128A4 (en) * | 2018-12-05 | 2022-08-17 | Vividion Therapeutics, Inc. | SUBSTITUTED ISOINDOLINONES AS MODULATORS OF CEREBLON-MEDIATED NEOSUBSTRATE RECRUITMENT |
| MX2021009087A (es) | 2019-01-29 | 2021-09-08 | Juno Therapeutics Inc | Anticuerpos y receptores quimericos de antigenos especificos para receptor 1 huerfano tipo receptor tirosina-cinasa (ror1). |
| US20230248696A1 (en) * | 2019-05-03 | 2023-08-10 | Dynamic Biologics Inc. | Lenalidomide prodrugs, polymeric conjugates, and formulations thereof, and their uses for the treatment of multiple myeloma |
| CN110343063A (zh) * | 2019-08-09 | 2019-10-18 | 新乡双鹭药业有限公司 | 一种泊马度胺合成中杂质的制备方法 |
| EP4021450B1 (en) | 2019-08-26 | 2025-11-05 | Arvinas Operations, Inc. | Methods of treating breast cancer with tetrahydronaphthalene derivatives as estrogen receptor degraders |
| US11535606B2 (en) | 2019-09-23 | 2022-12-27 | Accutar Biotechnology Inc. | Substituted quinoline-8-carbonitrile derivatives with androgen receptor degradation activity and uses thereof |
| CN114761003B (zh) * | 2019-09-23 | 2023-12-29 | 冰洲石生物科技公司 | 具有雄激素受体降解活性的新型脲类及其用途 |
| AU2020368542B2 (en) | 2019-10-17 | 2024-02-29 | Arvinas Operations, Inc. | Bifunctional molecules containing an E3 ubiquitine ligase binding moiety linked to a BCL6 targeting moiety |
| IL293027A (en) | 2019-11-19 | 2022-07-01 | Bristol Myers Squibb Co | Compounds useful as inhibitors of Helios protein |
| EP4076464A4 (en) * | 2019-12-17 | 2024-06-12 | Orionis Biosciences, Inc. | COMPOUNDS FOR MODULATION OF PROTEIN RECRUITMENT AND/OR DEGRADATION |
| AU2020405129A1 (en) | 2019-12-19 | 2022-06-23 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| BR112022020897A2 (pt) | 2020-04-15 | 2022-11-29 | Tecnimede Sociedade Tecnico Medicinal Sa | Forma de dosagem oral sólida compreendendo pomalidomida. |
| MX2022014071A (es) | 2020-05-09 | 2023-01-30 | Arvinas Operations Inc | Metodos para fabricar un compuesto bifuncional, formas ultrapuras del compuesto bifuncional y formas de dosificacion que comprenden el mismo. |
| EP4204418A1 (en) | 2020-08-28 | 2023-07-05 | Arvinas Operations, Inc. | Rapidly accelerating fibrosarcoma protein degrading compounds and associated methods of use |
| EP4211128A1 (en) | 2020-09-14 | 2023-07-19 | Arvinas Operations, Inc. | Crystalline forms of a compound for the targeted degradation of estrogen receptor |
| WO2022152821A1 (en) | 2021-01-13 | 2022-07-21 | Monte Rosa Therapeutics Ag | Isoindolinone compounds |
| RS66982B1 (sr) | 2021-04-06 | 2025-07-31 | Bristol Myers Squibb Co | Piridinil supstituisana oksoizoindolinska jedinjenja |
| EP4323352A1 (en) | 2021-04-16 | 2024-02-21 | Arvinas Operations, Inc. | Modulators of bcl6 proteolysis and associated methods of use |
| WO2023126530A1 (en) | 2021-12-31 | 2023-07-06 | A Fine House S.A. | Oral solution comprising lenalidomide |
| EP4456876A1 (en) | 2021-12-31 | 2024-11-06 | a Fine House S.A. | Lenalidomide oral solution |
| JP2025521543A (ja) | 2022-06-22 | 2025-07-10 | ジュノー セラピューティクス インコーポレイテッド | Ｃｄ１９標的ｃａｒ ｔ細胞のセカンドライン治療のための処置方法 |
| TW202432544A (zh) | 2022-09-07 | 2024-08-16 | 美商亞文納營運公司 | 快速加速纖維肉瘤降解化合物及相關使用方法 |
| WO2024097905A1 (en) | 2022-11-02 | 2024-05-10 | Celgene Corporation | Methods of treatment with t cell therapy and immunomodulatory agent maintenance therapy |
| TW202444727A (zh) | 2023-01-26 | 2024-11-16 | 美商艾維納斯手術有限公司 | 基於cereblon之kras降解protac及其相關用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9109645D0 (en) | 1991-05-03 | 1991-06-26 | Celltech Ltd | Recombinant antibodies |
| WO1992014455A1 (en) * | 1991-02-14 | 1992-09-03 | The Rockefeller University | METHOD FOR CONTROLLING ABNORMAL CONCENTRATION TNF α IN HUMAN TISSUES |
| US5629327A (en) * | 1993-03-01 | 1997-05-13 | Childrens Hospital Medical Center Corp. | Methods and compositions for inhibition of angiogenesis |
| US5463063A (en) * | 1993-07-02 | 1995-10-31 | Celgene Corporation | Ring closure of N-phthaloylglutamines |
| DE4422237A1 (de) * | 1994-06-24 | 1996-01-04 | Gruenenthal Gmbh | Verwendung von Lactamverbindungen als pharmazeutische Wirkstoffe |
| PL195916B1 (pl) * | 1996-07-24 | 2007-11-30 | Celgene Corp | Izomery optyczne podstawionej 1-okso-izoindoliny i 1,3-diokso-izoindoliny, kompozycje farmaceutyczne je zawierające oraz ich zastosowanie |
| US5635517B1 (en) * | 1996-07-24 | 1999-06-29 | Celgene Corp | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
-
1997
- 1997-07-24 PL PL97373743A patent/PL195916B1/pl unknown
- 1997-07-24 CZ CZ2011-89A patent/CZ304569B6/cs not_active IP Right Cessation
- 1997-07-24 EP EP97936295.1A patent/EP0925294B3/en not_active Expired - Lifetime
- 1997-07-24 CZ CZ1999202A patent/CZ295762B6/cs not_active IP Right Cessation
- 1997-07-24 PT PT10152833T patent/PT2177517E/pt unknown
- 1997-07-24 DK DK97936295.1T patent/DK0925294T6/da active
- 1997-07-24 WO PCT/US1997/013375 patent/WO1998003502A1/en not_active Ceased
- 1997-07-24 AT AT10152833T patent/ATE530542T1/de active
- 1997-07-24 AT AT09151443T patent/ATE500240T1/de active
- 1997-07-24 PT PT09151443T patent/PT2070920E/pt unknown
- 1997-07-24 PT PT97936295T patent/PT925294E/pt unknown
- 1997-07-24 AT AT97936295T patent/ATE229521T3/de unknown
- 1997-07-24 ES ES97936295.1T patent/ES2187805T7/es active Active
- 1997-07-24 PT PT02012942T patent/PT1285916E/pt unknown
- 1997-07-24 CA CA 2624949 patent/CA2624949C/en not_active Expired - Lifetime
- 1997-07-24 KR KR1020057004561A patent/KR20050032629A/ko not_active Ceased
- 1997-07-24 JP JP50725998A patent/JP4065567B2/ja not_active Expired - Lifetime
- 1997-07-24 AT AT02012942T patent/ATE460409T1/de active
- 1997-07-24 DE DE69717831.5T patent/DE69717831T3/de not_active Expired - Lifetime
- 1997-07-24 UA UA99010371A patent/UA60308C2/uk unknown
- 1997-07-24 DE DE69740140T patent/DE69740140D1/de not_active Expired - Lifetime
- 1997-07-24 EP EP20100183268 patent/EP2305663B1/en not_active Expired - Lifetime
- 1997-07-24 KR KR10-1999-7000565A patent/KR100534498B1/ko not_active Expired - Lifetime
- 1997-07-24 CA CA 2560523 patent/CA2560523C/en not_active Expired - Lifetime
- 1997-07-24 CN CN97180299A patent/CN1117089C/zh not_active Ceased
- 1997-07-24 DK DK02012942T patent/DK1285916T3/da active
- 1997-07-24 ES ES10183268.1T patent/ES2529190T3/es not_active Expired - Lifetime
- 1997-07-24 EP EP20020012942 patent/EP1285916B1/en not_active Expired - Lifetime
- 1997-07-24 ES ES02012942T patent/ES2339425T3/es not_active Expired - Lifetime
- 1997-07-24 SK SK91-99A patent/SK9199A3/sk unknown
- 1997-07-24 ES ES10152833T patent/ES2372577T3/es not_active Expired - Lifetime
- 1997-07-24 PL PL332867A patent/PL191566B1/pl unknown
- 1997-07-24 DE DE69739802T patent/DE69739802D1/de not_active Expired - Lifetime
- 1997-07-24 CZ CZ20050108A patent/CZ302378B6/cs not_active IP Right Cessation
- 1997-07-24 EP EP20090151443 patent/EP2070920B8/en not_active Expired - Lifetime
- 1997-07-24 NZ NZ333903A patent/NZ333903A/en not_active IP Right Cessation
- 1997-07-24 DE DE200712000079 patent/DE122007000079I2/de active Active
- 1997-07-24 CA CA 2261762 patent/CA2261762C/en not_active Expired - Lifetime
-
1999
- 1999-01-19 FI FI990101A patent/FI120687B/fi not_active IP Right Cessation
-
2007
- 2007-09-06 LU LU91359C patent/LU91359I2/fr unknown
- 2007-09-10 NL NL300291C patent/NL300291I2/nl unknown
- 2007-11-05 FR FR07C0056C patent/FR07C0056I2/fr active Active
-
2013
- 2013-10-15 HU HUS1300056C patent/HUS1300056I1/hu unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA60308C2 (uk) | ЗАМІЩЕНІ 2-(2,6-ДІОКСОПІПЕРИДИН-3-ІЛ)ФТАЛІМІДИ ТА 1-ОКСОІЗОІНДОЛІНИ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЗНИЖЕННЯ РІВНЯ ФПН-α | |
| RU2595250C1 (ru) | Замещенные 2,6-диоксопиперидины, фармацевтическая композиция на их основе и способы снижения уровней tnf-альфа | |
| US6335349B1 (en) | Substituted 2(2,6-dioxopiperidin-3-yl)isoindolines | |
| US8288415B2 (en) | Pharmaceutical compositions of 3-(4-amino-1-oxoisoindolin-2yl)-piperidine-2,6-dione | |
| EP2177517B1 (en) | Amino substituted 2-(2,6-dioxopiperidin-3-yl)-phthalimide for reducing TNF alpha levels | |
| HK1021819B (en) | Substituted 2(2,6-dioxopiperidin-3-yl) phthalimides and -1-oxoisoindolines and method of reducing tnf-alpha levels | |
| HK1021819C (en) | Substituted 2(2,6-dioxopiperidin-3-yl) phthalimides and -1-oxoisoindolines and method of reducing tnf-alpha levels | |
| HK1143360B (en) | Amino substituted 2-(2,6-dioxopiperidin-3-yl)-phthalimide for reducing tnf alpha levels | |
| HK1153736B (en) | Substituted 2-(2,6-dioxopiperidin-3-yl)-phthalimides and 1-oxoisoindolines and method of reducing tnf alpha levels |