UA82827C2 - Inhibitors against the production and release of inflammatory cytokines - Google Patents
Inhibitors against the production and release of inflammatory cytokines Download PDFInfo
- Publication number
- UA82827C2 UA82827C2 UA2003076746A UA2003076746A UA82827C2 UA 82827 C2 UA82827 C2 UA 82827C2 UA 2003076746 A UA2003076746 A UA 2003076746A UA 2003076746 A UA2003076746 A UA 2003076746A UA 82827 C2 UA82827 C2 UA 82827C2
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- UA
- Ukraine
- Prior art keywords
- group
- trifluoromethyl
- substituted
- groups
- phenyl
- Prior art date
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- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 125000000369 oxido group Chemical group [*]=O 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000001814 pectin Substances 0.000 description 1
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- 235000019477 peppermint oil Nutrition 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical group C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
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- 230000003334 potential effect Effects 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001308 pyruvoyl group Chemical group O=C([*])C(=O)C([H])([H])[H] 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 150000007659 semicarbazones Chemical group 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
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- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
- A61K31/055—Phenols the aromatic ring being substituted by halogen
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- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
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- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/42—Oxazoles
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Families Citing this family (82)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4224566B2 (ja) * | 2000-12-18 | 2009-02-18 | 株式会社医薬分子設計研究所 | 炎症性サイトカイン産生遊離抑制剤 |
EP1466912B1 (en) | 2002-01-18 | 2013-04-24 | Astellas Pharma Inc. | 2-acylaminothiazole derivative or salt thereof |
MY156407A (en) | 2002-02-28 | 2016-02-26 | Novartis Ag | 5-phenylthiazole derivatives and use as p13 kinase inhibitors |
EP2311818B1 (en) * | 2002-02-28 | 2013-01-16 | Novartis AG | Combination of a 5-phenylthiazole compound as PI3 kinase inhibitor with an antiinflammatory, bronchodilatory or antihistamine drug |
WO2003103658A1 (ja) * | 2002-06-05 | 2003-12-18 | 株式会社医薬分子設計研究所 | 免疫関連プロテインキナーゼ阻害剤 |
JPWO2003103647A1 (ja) * | 2002-06-05 | 2005-10-06 | 株式会社医薬分子設計研究所 | Ap−1及びnfat活性化阻害剤 |
EP1510207A4 (en) * | 2002-06-05 | 2008-12-31 | Inst Med Molecular Design Inc | THERAPEUTIC MEDICAMENT AGAINST DIABETES |
EP1514544A4 (en) * | 2002-06-06 | 2009-01-07 | Inst Med Molecular Design Inc | HYPO-ALLERGENIC |
EA009051B1 (ru) * | 2002-06-06 | 2007-10-26 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | О-замещенные гидроксиарильные производные |
TW200307535A (en) * | 2002-06-10 | 2003-12-16 | Inst Med Molecular Design Inc | Therapeutic agent for cancer |
AU2003242098B2 (en) * | 2002-06-10 | 2008-11-20 | Institute Of Medicinal Molecular Design, Inc | Inhibitors against activation of NFkappaB |
CA2488979A1 (en) * | 2002-06-11 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Medicament for treatment of neurodegenerative diseases |
EP1541139A4 (en) * | 2002-06-26 | 2008-06-11 | Signal Creation Inc | DRUG COMPOSITION WITH NF-KAPPA B HEMMER |
NZ537858A (en) * | 2002-07-15 | 2008-04-30 | Myriad Genetics Inc | Compounds, compositions, and methods employing same |
AU2003272901A1 (en) * | 2002-10-01 | 2004-04-23 | Takara Bio Inc. | Remedies |
US7959161B2 (en) * | 2002-11-12 | 2011-06-14 | Nok Corporation | Rubber-like elastic part |
WO2004072056A1 (ja) * | 2003-02-14 | 2004-08-26 | Keio University | 医薬組成物 |
AU2004228453B2 (en) * | 2003-04-11 | 2010-08-19 | Glenmark Pharmaceuticals S.A. | Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them |
CN100406006C (zh) * | 2003-07-16 | 2008-07-30 | 株式会社医药分子设计研究所 | 皮肤色素沉着的治疗剂 |
KR20060056363A (ko) * | 2003-08-06 | 2006-05-24 | 각고호우징 게이오기주크 | 매크로파지 활성화 저해제 |
CA2539162A1 (en) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | Cinnamoyl derivatives and use thereof |
EP1671948A4 (en) | 2003-09-17 | 2007-03-14 | Sumitomo Chemical Co | CINNAMOYL COMPOUND AND USE THEREOF |
JPWO2005039556A1 (ja) * | 2003-10-29 | 2007-02-15 | 紘一 首藤 | 血行再建術後の再狭窄又は再閉塞の治療及び/又は予防のための医薬 |
AU2004287573A1 (en) * | 2003-11-07 | 2005-05-19 | F. Hoffmann-La Roche Ag | Benzo [b][1,4] dioxepine derivatives |
TW200529812A (en) | 2003-12-26 | 2005-09-16 | Chugai Pharmaceutical Co Ltd | Benzamide derivatives |
WO2005094805A1 (ja) * | 2004-04-01 | 2005-10-13 | Institute Of Medicinal Molecular Design. Inc. | イミン誘導体及びアミド誘導体 |
JP5140231B2 (ja) * | 2004-04-08 | 2013-02-06 | 株式会社ロッテ | IκBキナーゼ阻害剤 |
WO2006013873A1 (ja) * | 2004-08-05 | 2006-02-09 | Institute Of Medicinal Molecular Design. Inc. | シクロオキシゲナーゼ阻害作用を有する医薬 |
AU2005279845A1 (en) * | 2004-08-30 | 2006-03-09 | Government Of The United States Of America, As Represented By The Secretary Department Of Health And Human Services | Inhibition of viruses using RNase H inhibitors |
UA90864C2 (en) * | 2004-09-09 | 2010-06-10 | Ромарк Лебораториз, Л.К. | Halogenated benzamide derivatives |
WO2006032322A1 (en) * | 2004-09-20 | 2006-03-30 | 4Sc Ag | NOVEL HETEROCYCLIC NF-κB INHIBITORS |
EP1637529A1 (en) * | 2004-09-20 | 2006-03-22 | 4Sc Ag | Novel piperidin-4-yl-thiazole-carboxamide analogues as inhibitors of T-cell proliferation and uses thereof |
US7601745B2 (en) * | 2004-09-27 | 2009-10-13 | 4Sc Ag | Heterocyclic NF-kB inhibitors |
EP1886681A3 (en) * | 2004-10-07 | 2008-11-19 | Sulfidris S.r.l. | 5-(p-hydroxyphenyl)-3H-1,2-dithiol-3-thione valproate ester |
RU2458919C2 (ru) | 2005-04-13 | 2012-08-20 | Астекс Терапьютикс Лимитед | ПРОИЗВОДНЫЕ ГИДРОКСИБЕНЗАМИДА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ Hsp90 |
CA2639910A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
EP1834954A1 (en) * | 2006-03-15 | 2007-09-19 | 4Sc Ag | Thiazoles as NF-kB Inhibitors (proteasome inhibitors) |
US7671058B2 (en) | 2006-06-21 | 2010-03-02 | Institute Of Medicinal Molecular Design, Inc. | N-(3,4-disubstituted phenyl) salicylamide derivatives |
CN101096363B (zh) * | 2006-06-27 | 2011-05-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 2,4,5-三取代噻唑类化合物、其制备方法、药物组合物及其制药用途 |
WO2008044029A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
WO2008044027A2 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical compounds having hsp90 inhibitory or modulating activity |
JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
EP2073804B1 (en) | 2006-10-12 | 2017-09-13 | Astex Therapeutics Limited | Hydroxy-substituted benzoic acid amide compounds for use in the treatment of pain |
GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
US7737149B2 (en) | 2006-12-21 | 2010-06-15 | Astrazeneca Ab | N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide and salts thereof |
SI2178870T1 (sl) * | 2007-08-17 | 2018-11-30 | Lg Chem, Ltd. | Indolne in indazolne spojine kot inhibitor celične nekroze |
RU2010120675A (ru) | 2007-10-23 | 2011-11-27 | Инститьют Оф Медисинал Молекьюлар Дизайн, Инк. (Jp) | Ингибитор продуцирования pai-1 |
US7868001B2 (en) * | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
EP2328872A1 (en) * | 2008-06-19 | 2011-06-08 | AstraZeneca AB | Pyrazole compounds 436 |
EP2484666A1 (en) * | 2008-08-15 | 2012-08-08 | Georgetown University | Fluorescent regulators of RASSF1A expression and human cancer cell proliferation |
AR075401A1 (es) * | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Indanos sustituidos, procesos para su preparacion y uso de los mismos como un medicamento |
CN101928227A (zh) * | 2009-12-16 | 2010-12-29 | 天津工业大学 | 6-甲氧基-2-萘乙酸与水杨酰苯胺类化合物的互联体前药制备方法及应用 |
FR2954315B1 (fr) * | 2009-12-23 | 2012-02-24 | Galderma Res & Dev | Nouveaux derives phenoliques, et leur utilisation pharmaceutique ou cosmetique |
TWI455711B (zh) * | 2011-03-11 | 2014-10-11 | Nat Defense Medical Ct | 用以抑制前驅蝕骨細胞生長之醫藥組合物 |
CN102920688A (zh) * | 2011-11-16 | 2013-02-13 | 浙江大学 | 4-羟基水杨酰苯胺在制备防治乙型肝炎的药物中的应用 |
US9994514B2 (en) | 2012-05-08 | 2018-06-12 | Aeromics, Inc. | Methods of treating cerebral edema and spinal cord edema |
US20140179712A1 (en) | 2012-12-21 | 2014-06-26 | Astrazeneca Ab | Pharmaceutical formulation of n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2h-pyrazol-3-yl]-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]benzamide |
CN105636583B (zh) | 2013-09-13 | 2019-08-20 | 板井昭子 | 水溶液制剂及其制造方法 |
CN106163506A (zh) | 2013-11-06 | 2016-11-23 | 埃罗米克斯公司 | 新配方 |
WO2015109318A2 (en) | 2014-01-17 | 2015-07-23 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona, Acting For And On Behalf Of Arizona State University | Therapeutic methods |
AU2015314287B2 (en) | 2014-09-12 | 2019-04-18 | UNION therapeutics A/S | Antibacterial use of halogenated salicylanilides |
JP2017535546A (ja) * | 2014-11-13 | 2017-11-30 | エアロミクス・インコーポレイテッドAeromics,Inc. | 新規な方法 |
WO2016094688A1 (en) * | 2014-12-10 | 2016-06-16 | Massachusetts Institute Of Technology | Fused 1,3-azole derivatives useful for the treatment of proliferative diseases |
CN105797154B (zh) * | 2014-12-31 | 2020-03-10 | 中国科学院上海生命科学研究院 | 软骨干细胞的分离及其应用 |
GB201509326D0 (en) | 2015-05-29 | 2015-07-15 | Antibio Tx Aps | Novel use |
US11053255B2 (en) | 2015-06-22 | 2021-07-06 | Georgetown University | Synthesis of mahanine and related compounds |
SG10201914118SA (en) | 2015-09-01 | 2020-02-27 | First Wave Bio Inc | Methods and compositions for treating conditions associated with an abnormal inflammatory responses |
CA3012846A1 (en) | 2016-02-16 | 2017-08-24 | Massachusetts Institute Of Technology | Max binders as myc modulators and uses thereof |
US10238626B2 (en) | 2017-01-23 | 2019-03-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Therapeutic compounds |
US10238655B2 (en) | 2017-01-23 | 2019-03-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Dihydroindene and tetrahydronaphthalene compounds |
US10231947B2 (en) | 2017-01-23 | 2019-03-19 | Arizona Board Of Regents On Behalf Of Arizona State University | Isochroman compounds and methods of use thereof |
MX2020000576A (es) | 2017-07-21 | 2020-09-10 | Antabio Sas | Compuestos quimicos. |
RU2679892C1 (ru) * | 2017-11-01 | 2019-02-14 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермская государственная фармацевтическая академия" Министерства здравоохранения Российской Федерации (ФГБОУ ВО ПГФА Минздрава России) | 4-метилфениламид n-бензоил-5-бром антраниловой кислоты, проявляющий противовоспалительную активность |
US11419834B2 (en) | 2019-02-25 | 2022-08-23 | Rhode Island Hospital | Methods for treating diseases or infections caused by or associated with H. pylori using a halogenated salicylanilide |
US11957687B2 (en) | 2019-07-02 | 2024-04-16 | Regeneron Pharmaceuticals, Inc. | Modulators of HSD17B13 and methods of use thereof |
BR112022009457A2 (pt) * | 2019-11-18 | 2022-08-16 | Univ California | Inibidores duplos de receptor androgênico/akr1c3 |
US10980756B1 (en) | 2020-03-16 | 2021-04-20 | First Wave Bio, Inc. | Methods of treatment |
CN115504940A (zh) * | 2021-06-23 | 2022-12-23 | 中国科学院上海药物研究所 | 一种酰胺类化合物、其制备方法和制药用途 |
CN117105810B (zh) * | 2023-10-23 | 2024-02-09 | 中国农业大学 | 一种具有广谱抗菌活性的化合物及其抗菌组合物 |
Family Cites Families (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1017606B (de) * | 1951-12-29 | 1957-10-17 | Geigy Ag J R | Verfahren zur Herstellung von baktericiden Salicylaniliden |
JPS37225B1 (ja) * | 1958-07-23 | 1962-01-23 | ||
US3041236A (en) * | 1959-09-18 | 1962-06-26 | Herbert C Stecker | Germicides containing trifluoromethyl halogenated salicylanilides |
BE615511A (ja) * | 1961-03-25 | |||
NL292958A (ja) * | 1962-05-29 | 1900-01-01 | ||
GB1079177A (en) * | 1963-06-11 | 1967-08-16 | Stecker Internat S P A | Improvements in pesticide composition for destroying internal worm parasites in animals |
FR1481713A (fr) | 1965-10-11 | 1967-05-19 | Stecker Internat S P A | Benzoazinediones et compositions germicides qui les contiennent |
GB1099865A (en) | 1965-10-11 | 1968-01-17 | Stecker Internat S P A | Benzoazinediones and germicidal compositions made therewith |
US3305440A (en) * | 1965-10-13 | 1967-02-21 | Monsanto Co | Method of destroying gastropods |
BE756232A (fr) * | 1969-09-16 | 1971-03-16 | Hoechst Ag | Anilides de l'acide 3-acyl-alpha-resorcylique et leur preparation |
FR2088225A1 (en) | 1970-05-29 | 1972-01-07 | Ugine Kuhlmann | Substd salicylanilides - having antiuric props |
DE2120861A1 (de) * | 1971-04-28 | 1972-11-09 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Fungizide Mittel |
DE2120862A1 (de) * | 1971-04-28 | 1972-11-09 | Farbenfabriken Bayer Ag, 5090 Leverkusen | 3,5-Disubstituierte 2-Acyloxybenzoesäureanilide, Verfahren zu ihrer Herstellung und ihre insektizide und akarizide Verwendung |
US3906034A (en) * | 1972-03-21 | 1975-09-16 | Hoechst Ag | Trifluoromethyl-salicylanilides |
JPS52110835A (en) | 1976-03-11 | 1977-09-17 | Microbial Chem Res Found | Remedy for immunological diseases containing benzanilide derivative as active ingredient |
FR2434158A1 (fr) | 1978-08-25 | 1980-03-21 | Esteve Int Prod | Nouveaux derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments |
US4358443A (en) * | 1980-04-14 | 1982-11-09 | The Research Foundation Of State University Of New York | Method and composition for controlling the growth of microorganisms |
US4287191A (en) * | 1980-04-14 | 1981-09-01 | The Research Foundation Of State University Of New York | Novel salicylanilides and microbiocidal compositions and uses thereof |
JPS57112360A (en) | 1980-08-08 | 1982-07-13 | Risaachi Fuandeeshiyon Obu Sut | Microbe growth controlling compound and method |
CA1219587A (en) * | 1981-12-14 | 1987-03-24 | Norman P. Jensen | Hydroxybenzylaminobenzenes as anti-inflammatory agents |
JPS59118750A (ja) * | 1982-12-27 | 1984-07-09 | Eisai Co Ltd | カルボン酸アミド化合物およびその誘導体 |
US4560549A (en) * | 1983-08-24 | 1985-12-24 | Lever Brothers Company | Method of relieving pain and inflammatory conditions employing substituted salicylamides |
US4742083A (en) * | 1983-08-24 | 1988-05-03 | Lever Brothers Company | Method of relieving pain and inflammatory conditions employing substituted salicylamides |
US4725590A (en) * | 1983-08-24 | 1988-02-16 | Lever Brothers Company | Method of relieving pain and inflammatory conditions employing substituted salicylamides |
JPS6299329A (ja) * | 1983-08-24 | 1987-05-08 | ユニリ−バ−・ナ−ムロ−ゼ・ベンノ−トシヤ−プ | 皮膚用抗炎症組成物 |
US4659738A (en) * | 1985-02-15 | 1987-04-21 | The United States Of America As Represented By The Secretary Of The Army | Topical prophylaxis against schistosomal infections |
JPS6230780A (ja) * | 1985-04-17 | 1987-02-09 | Ss Pharmaceut Co Ltd | 1,7−ナフチリジン誘導体及びこれを含有する薬剤 |
US4939133A (en) * | 1985-10-01 | 1990-07-03 | Warner-Lambert Company | N-substituted-2-hydroxy-α-oxo-benzeneacetamides and pharmaceutical compositions having activity as modulators of the arachidonic acid cascade |
JPH0755902B2 (ja) | 1986-10-21 | 1995-06-14 | 株式会社ツムラ | アルド−スリダクタ−ゼ阻害剤 |
US4966906A (en) * | 1987-11-27 | 1990-10-30 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-isoquinolinecarboxamides |
US4952588A (en) * | 1987-11-27 | 1990-08-28 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinoline-and 1-aryl-3-isoquinoline-carboxamides |
US4786644A (en) * | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
JP2988739B2 (ja) | 1990-04-16 | 1999-12-13 | 協和醗酵工業株式会社 | 1,8−ナフチリジン−2−オン誘導体 |
JPH04217916A (ja) | 1990-06-21 | 1992-08-07 | Japan Tobacco Inc | 抗炎症剤 |
CA2054339C (en) | 1990-11-02 | 2002-12-24 | Francesco G. Salituro | 3-amidoindolyl derivatives |
SK280617B6 (sk) | 1992-01-16 | 2000-05-16 | Hoechst Aktiengesellschaft | Arylcykloalkylové deriváty, spôsob ich prípravy, f |
US6159988A (en) * | 1992-01-16 | 2000-12-12 | Hoeschst Aktiengesellschaft | Arylcycloalkyl derivatives, their production and their use |
JP2546622B2 (ja) * | 1994-02-14 | 1996-10-23 | オリエント時計株式会社 | 複合混合多層膜 |
JPH08175990A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | Pi3キナーゼ阻害剤とその製造法 |
DE69634822T2 (de) * | 1995-08-22 | 2006-04-27 | Japan Tobacco Inc. | Amid-verbindungen und ihre anwendung |
JPH09169747A (ja) | 1995-12-18 | 1997-06-30 | Kyorin Pharmaceut Co Ltd | 新規置換フェニルチアゾリジン−2,4−ジオン誘導体及びその製造法 |
JPH09227561A (ja) | 1996-02-21 | 1997-09-02 | Tanabe Seiyaku Co Ltd | キサンチン誘導体 |
PL182022B1 (pl) | 1996-04-18 | 2001-10-31 | Inst Przemyslu Organiczego | β-aminoestry anilidów kwasu salicylowego |
JPH1087491A (ja) | 1996-07-26 | 1998-04-07 | Asahi Chem Ind Co Ltd | 転写調節因子阻害剤 |
JPH1045738A (ja) | 1996-07-29 | 1998-02-17 | Microbial Chem Res Found | 抗生物質エポキシキノマイシンcおよびdとその製造法ならびに抗リウマチ剤 |
US5958911A (en) * | 1996-11-05 | 1999-09-28 | The Research Foundation Of State University Of New York | Method of relieving inflammation by using 5-alkylsulfonylsalicylanilides |
JPH1121243A (ja) | 1997-05-06 | 1999-01-26 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
JPH1121225A (ja) | 1997-06-27 | 1999-01-26 | Tanabe Seiyaku Co Ltd | 美白用成分およびこれを含有する美白用皮膚外用剤 |
US6117859A (en) * | 1997-11-04 | 2000-09-12 | The Research Foundation Of State University Of New York | Method of relieving chronic inflammation by using 5-alkylsulfonylsalicylanilides |
US6022884A (en) * | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
JPH11180873A (ja) | 1997-12-22 | 1999-07-06 | Kaken Shoyaku Kk | NF−κB活性阻害剤 |
JPH11217361A (ja) | 1998-01-29 | 1999-08-10 | Fuji Photo Film Co Ltd | ナフトキノン化合物及び該化合物からなる医薬 |
JP2000080041A (ja) | 1998-03-09 | 2000-03-21 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
US6225329B1 (en) * | 1998-03-12 | 2001-05-01 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPases) |
US20020019412A1 (en) * | 1998-03-12 | 2002-02-14 | Henrik Sune Andersen | Modulators of protein tyrosine phosphatases (ptpases) |
BR9908726A (pt) | 1998-03-12 | 2000-11-21 | Novo Nordisk As | Composto, composiçãp farmacêutica, uso de um composto, e, processos para tratamento do diabete do tipo i e de disfunções imunes, para fabricação de um medicamento, e, para preparação de um composto |
US20020002199A1 (en) * | 1998-03-12 | 2002-01-03 | Lone Jeppesen | Modulators of protein tyrosine phosphatases (ptpases) |
US6262044B1 (en) * | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
KR20010012773A (ko) | 1998-03-20 | 2001-02-26 | 도리이 신이치로 | 페닐메틸 벤조퀴논을 유효성분으로 함유하는 NF-κB억제제 |
JP2002510679A (ja) * | 1998-04-08 | 2002-04-09 | アボット・ラボラトリーズ | ピラゾールサイトカイン産生阻害剤 |
JP2002512997A (ja) * | 1998-04-29 | 2002-05-08 | バーテックス ファーマシューティカルズ インコーポレイテッド | Impdh酵素のインヒビター |
US5905090A (en) * | 1998-04-29 | 1999-05-18 | Italfarmaco S.P.A. | Analogues of the active metabolite of leflunomide |
SK286247B6 (sk) * | 1998-05-15 | 2008-06-06 | Astrazeneca Ab | Benzamidové deriváty, spôsob ich prípravy, farmaceutické prostriedky, ktoré ich obsahujú a ich použitie pri príprave liečiva na liečbu chorobných stavov sprostredkovaných cytokínmi |
HUP0102782A3 (en) * | 1998-06-19 | 2002-12-28 | Smithkline Beecham Corp | Salycilanilide as inhibitors of transcription factor nf-kb |
DE69942454D1 (de) * | 1998-07-01 | 2010-07-15 | Univ Pennsylvania | Hohlraum-induzierte allosterische modifikation von intermolekularen interaktionen und verfahren zur identifikation von verbindungen, die diese bewirken. |
ATE266662T1 (de) | 1998-07-22 | 2004-05-15 | Daiichi Suntory Pharma Co Ltd | Nf-kappa b inhibitoren, die indanderivate als aktiven bestandteil enthalten |
EP1113000A4 (en) | 1998-09-11 | 2004-12-15 | Ajinomoto Kk | BENZENE DERIVATIVES AND THEIR MEDICAL APPLICATION |
JP2000169479A (ja) | 1998-12-09 | 2000-06-20 | Kyowa Hakko Kogyo Co Ltd | NF−κB活性化阻害剤 |
UY25842A1 (es) * | 1998-12-16 | 2001-04-30 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
US6653309B1 (en) * | 1999-04-26 | 2003-11-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme technical field of the invention |
EP1205478A4 (en) | 1999-08-06 | 2004-06-30 | Takeda Chemical Industries Ltd | P38MAP KINASE INHIBITORS |
CN1185212C (zh) | 1999-08-11 | 2005-01-19 | 庆应大学 | 水杨酸酰胺衍生物 |
ES2240017T3 (es) | 1999-09-30 | 2005-10-16 | Pfizer Products Inc. | Derivados de 6-azauracilo como ligandos de receptores tiroideos. |
US6787652B1 (en) * | 1999-09-30 | 2004-09-07 | Pfizer, Inc. | 6-Azauracil derivatives as thyroid receptor ligands |
US6706766B2 (en) * | 1999-12-13 | 2004-03-16 | President And Fellows Of Harvard College | Small molecules used to increase cell death |
US6414013B1 (en) | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
JP4224566B2 (ja) * | 2000-12-18 | 2009-02-18 | 株式会社医薬分子設計研究所 | 炎症性サイトカイン産生遊離抑制剤 |
EP1344525A4 (en) | 2000-12-22 | 2005-05-25 | Ishihara Sangyo Kaisha | ANILINE DERIVATIVES OR ITS SALTS AND CYTOKINE PRODUCTION INHIBITORS CONTAINING THEM |
CA2410816A1 (en) | 2001-03-27 | 2002-10-03 | Suntory Limited | Nf-.kappa.b inhibitor containing substituted benzoic acid derivative as active ingredient |
JP4540905B2 (ja) * | 2001-11-13 | 2010-09-08 | Hoya株式会社 | 焼結体の製造方法 |
JPWO2003103647A1 (ja) * | 2002-06-05 | 2005-10-06 | 株式会社医薬分子設計研究所 | Ap−1及びnfat活性化阻害剤 |
WO2003103658A1 (ja) * | 2002-06-05 | 2003-12-18 | 株式会社医薬分子設計研究所 | 免疫関連プロテインキナーゼ阻害剤 |
EP1510207A4 (en) * | 2002-06-05 | 2008-12-31 | Inst Med Molecular Design Inc | THERAPEUTIC MEDICAMENT AGAINST DIABETES |
EP1514544A4 (en) * | 2002-06-06 | 2009-01-07 | Inst Med Molecular Design Inc | HYPO-ALLERGENIC |
EA009051B1 (ru) * | 2002-06-06 | 2007-10-26 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | О-замещенные гидроксиарильные производные |
TW200307535A (en) * | 2002-06-10 | 2003-12-16 | Inst Med Molecular Design Inc | Therapeutic agent for cancer |
AU2003242098B2 (en) * | 2002-06-10 | 2008-11-20 | Institute Of Medicinal Molecular Design, Inc | Inhibitors against activation of NFkappaB |
CA2488979A1 (en) * | 2002-06-11 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Medicament for treatment of neurodegenerative diseases |
WO2004006906A2 (en) | 2002-07-15 | 2004-01-22 | Combinatorx, Incorporated | Methods for the treatment of neoplasms |
CN100406006C (zh) | 2003-07-16 | 2008-07-30 | 株式会社医药分子设计研究所 | 皮肤色素沉着的治疗剂 |
JP4217981B2 (ja) | 2005-02-08 | 2009-02-04 | Smc株式会社 | 直動・回転複合アクチュエータ |
JP4217916B2 (ja) | 2006-02-15 | 2009-02-04 | 三菱ふそうトラック・バス株式会社 | ハイブリッド電気自動車の制御装置 |
-
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- 2001-12-18 KR KR1020037008036A patent/KR101088557B1/ko not_active IP Right Cessation
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- 2001-12-18 CN CNA2007101400603A patent/CN101125138A/zh active Pending
- 2001-12-18 EP EP07015427A patent/EP1847263A3/en not_active Withdrawn
- 2001-12-18 KR KR1020097016971A patent/KR20090090406A/ko not_active Application Discontinuation
- 2001-12-18 UA UA2003076746A patent/UA82827C2/uk unknown
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