NO327418B1 - Nikotinamidderivater samt anvendelse og fremstilling derav og farmasoytisk preparat - Google Patents
Nikotinamidderivater samt anvendelse og fremstilling derav og farmasoytisk preparat Download PDFInfo
- Publication number
- NO327418B1 NO327418B1 NO20043176A NO20043176A NO327418B1 NO 327418 B1 NO327418 B1 NO 327418B1 NO 20043176 A NO20043176 A NO 20043176A NO 20043176 A NO20043176 A NO 20043176A NO 327418 B1 NO327418 B1 NO 327418B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- compound
- optionally substituted
- phenyl
- formula
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 16
- 150000005480 nicotinamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 30
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 30
- 230000000694 effects Effects 0.000 claims abstract description 12
- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 102000004127 Cytokines Human genes 0.000 claims abstract description 6
- 108090000695 Cytokines Proteins 0.000 claims abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 149
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- KKYABQBFGDZVNQ-UHFFFAOYSA-N 6-[5-[(cyclopropylamino)-oxomethyl]-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)-3-pyridinecarboxamide Chemical group CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1 KKYABQBFGDZVNQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 72
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 54
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 49
- 230000014759 maintenance of location Effects 0.000 description 46
- 239000002904 solvent Substances 0.000 description 46
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 42
- 238000007429 general method Methods 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 36
- 239000000377 silicon dioxide Substances 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000011570 nicotinamide Substances 0.000 description 28
- 229960003966 nicotinamide Drugs 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 229910000029 sodium carbonate Inorganic materials 0.000 description 27
- 235000017550 sodium carbonate Nutrition 0.000 description 27
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 25
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
- -1 3-methylbut-2-enyl Chemical group 0.000 description 22
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 235000002639 sodium chloride Nutrition 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- NMLPKVQVDDARTN-UHFFFAOYSA-N 6-chloro-n-(cyclopropylmethyl)pyridine-3-carboxamide Chemical compound C1=NC(Cl)=CC=C1C(=O)NCC1CC1 NMLPKVQVDDARTN-UHFFFAOYSA-N 0.000 description 11
- 239000007821 HATU Substances 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 235000011056 potassium acetate Nutrition 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000012267 brine Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
- LMUKBBLEUSPBDV-UHFFFAOYSA-N 6-chloro-n-(4-methoxyphenyl)pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(Cl)N=C1 LMUKBBLEUSPBDV-UHFFFAOYSA-N 0.000 description 7
- KLNMZIVXZVZTSK-UHFFFAOYSA-N 6-chloro-n-[(3-methoxyphenyl)methyl]pyridine-3-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C=NC(Cl)=CC=2)=C1 KLNMZIVXZVZTSK-UHFFFAOYSA-N 0.000 description 7
- MEIDHSQDDQTXGT-UHFFFAOYSA-N 6-chloro-n-[[3-(methanesulfonamido)phenyl]methyl]pyridine-3-carboxamide Chemical compound CS(=O)(=O)NC1=CC=CC(CNC(=O)C=2C=NC(Cl)=CC=2)=C1 MEIDHSQDDQTXGT-UHFFFAOYSA-N 0.000 description 7
- 101150003085 Pdcl gene Proteins 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- NNBJROGIRIFUSQ-UHFFFAOYSA-N 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-n-(1,3-thiazol-2-yl)benzamide Chemical compound CC1=CC=C(C(=O)NC=2SC=CN=2)C=C1B1OC(C)(C)C(C)(C)O1 NNBJROGIRIFUSQ-UHFFFAOYSA-N 0.000 description 6
- NLNRWBMSUOHHKO-UHFFFAOYSA-N 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-n-(3h-thiadiazol-2-yl)benzamide Chemical compound CC1=CC=C(C(=O)NN2SC=CN2)C=C1B1OC(C)(C)C(C)(C)O1 NLNRWBMSUOHHKO-UHFFFAOYSA-N 0.000 description 6
- JDJBRMNTXORYEN-UHFFFAOYSA-N 6-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)N=C1 JDJBRMNTXORYEN-UHFFFAOYSA-N 0.000 description 6
- HNPFSBAFFHLEOL-UHFFFAOYSA-N 6-chloro-n-[2-[(4-methylpiperazin-1-yl)methyl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC=C1NC(=O)C1=CC=C(Cl)N=C1 HNPFSBAFFHLEOL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 239000013543 active substance Substances 0.000 description 6
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- QMNHRHWOJSWJJV-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Chemical compound CC1=CC=C(C(=O)NCC2CC2)C=C1B1OC(C)(C)C(C)(C)O1 QMNHRHWOJSWJJV-UHFFFAOYSA-N 0.000 description 6
- GLSSVRGOTTUQNM-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1B1OC(C)(C)C(C)(C)O1 GLSSVRGOTTUQNM-UHFFFAOYSA-N 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
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- SUZCHODXFJYVKA-UHFFFAOYSA-N 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1B1OC(C)(C)C(C)(C)O1 SUZCHODXFJYVKA-UHFFFAOYSA-N 0.000 description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0203301.7A GB0203301D0 (en) | 2002-02-12 | 2002-02-12 | Novel compounds |
GB0225385A GB0225385D0 (en) | 2002-10-31 | 2002-10-31 | Novel compounds |
PCT/GB2003/000554 WO2003068747A1 (en) | 2002-02-12 | 2003-02-10 | Nicotinamide derivates useful as p38 inhibitors |
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NO20043176A NO327418B1 (no) | 2002-02-12 | 2004-07-26 | Nikotinamidderivater samt anvendelse og fremstilling derav og farmasoytisk preparat |
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Families Citing this family (69)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0124938D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124934D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124941D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124939D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124936D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124933D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
DK1474395T3 (da) | 2002-02-12 | 2008-02-11 | Smithkline Beecham Corp | Nicotinamidderivater, der er nyttige som p38-inhibitorer |
GB0209891D0 (en) | 2002-04-30 | 2002-06-05 | Glaxo Group Ltd | Novel compounds |
GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
GB0308201D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
GB0308186D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
GB0308185D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
ES2315703T3 (es) * | 2003-07-25 | 2009-04-01 | Novartis Ag | Inhibidores de la quinasa p-38. |
GB0318814D0 (en) * | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
WO2005033079A1 (ja) | 2003-09-30 | 2005-04-14 | Eisai Co., Ltd. | ヘテロ環化合物を含有する新規な抗真菌剤 |
GB0324790D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Amide derivatives |
GB0402143D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
GB0402137D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
GB0402138D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
GB0402140D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
WO2006016548A1 (ja) * | 2004-08-09 | 2006-02-16 | Eisai R & D Management Co., Ltd. | ヘテロ環化合物を含有する新規な抗マラリア剤 |
KR101366414B1 (ko) | 2004-09-02 | 2014-03-18 | 쿠리스 인코퍼레이션 | 헤지호그 신호전달에 대한 피리딜 억제제 |
US20080051416A1 (en) * | 2004-10-05 | 2008-02-28 | Smithkline Beecham Corporation | Novel Compounds |
GB0512429D0 (en) * | 2005-06-17 | 2005-07-27 | Smithkline Beecham Corp | Novel compound |
CA2621364A1 (en) | 2005-09-16 | 2007-03-22 | Arrow Therapeutics Limited | Biphenyl derivatives and their use in treating hepatitis c |
TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
EP1984338B8 (en) * | 2006-01-31 | 2013-05-22 | Synta Pharmaceuticals Corp. | Pyridylphenyl compounds for inflammation and immune-related uses |
WO2007100282A1 (en) * | 2006-02-28 | 2007-09-07 | Astrazeneca Ab | New salts of an indole derivative and their use in medicine |
GB0612026D0 (en) | 2006-06-16 | 2006-07-26 | Smithkline Beecham Corp | New use |
WO2008035726A1 (fr) | 2006-09-21 | 2008-03-27 | Eisai R & D Management Co., Ltd. | Dérivé de pyridine substitué par un cycle hétéroaryle, et agent antifongique le comprenant |
WO2008071665A1 (en) * | 2006-12-12 | 2008-06-19 | Smithkline Beecham Corporation | A nicotinamide derivative useful as p38 kinase inhibitor |
TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
KR20100015897A (ko) | 2007-04-27 | 2010-02-12 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 헤테로환 치환 피리딘 유도체의 염 또는 그의 결정 |
EP2183241B1 (en) | 2007-05-03 | 2012-12-19 | Pfizer Limited | 2-pyridine carboxamide derivatives as sodium channel modulators |
JP5645663B2 (ja) * | 2007-08-15 | 2014-12-24 | プレジデント アンド フェローズ オブ ハーバード カレッジ | ネクロトーシスのヘテロ環式抑制剤 |
TW200916458A (en) * | 2007-09-05 | 2009-04-16 | Astrazeneca Ab | Heterocyclic compounds and methods of use thereof |
WO2009034390A1 (en) * | 2007-09-14 | 2009-03-19 | Arrow Therapeutics Limited | Heterocyclic derivatives and their use in treating hepatitis c |
US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
US20090281089A1 (en) * | 2008-04-11 | 2009-11-12 | Genentech, Inc. | Pyridyl inhibitors of hedgehog signalling |
US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
US8713459B2 (en) | 2009-05-29 | 2014-04-29 | Jason Philip Yanchar | Graphical planner |
CN102633715B (zh) * | 2012-03-23 | 2014-03-26 | 无锡爱内特营养保健品科技有限公司 | 一种丝裂原蛋白激酶p38的抑制剂及其制备方法 |
RU2014152454A (ru) * | 2012-07-17 | 2016-09-10 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Производное никотинамида в лечении острого коронарного синдрома |
RS59458B1 (sr) | 2012-10-17 | 2019-11-29 | Macrophage Pharma Ltd | N-[2-{4-[6-amino-5-(2,4-difluorobenzoil)-2-oksopiridin-1(2h)-il]-3,5-difluorofenil}etil]-l-alanin i njegov tetrabutil ester |
US9725452B2 (en) | 2013-03-15 | 2017-08-08 | Presidents And Fellows Of Harvard College | Substituted indoles and pyrroles as RIP kinase inhibitors |
CA2917277A1 (en) * | 2013-07-10 | 2015-01-15 | Glaxosmithkline Intellectual Property (No.2) Limited | Losmapimod for use in treating glomerular disease |
AU2015220873A1 (en) | 2014-02-19 | 2016-08-11 | H. Lundbeck A/S | 2-amino-3, 5, 5-trifluoro-3, 4, 5, 6-tetrahydropyridines as BACE1 inhibitors for treatment of Alzheimer's disease |
WO2015170218A1 (en) | 2014-05-07 | 2015-11-12 | Pfizer Inc. | Tropomyosin-related kinase inhibitors |
CR20170187A (es) | 2014-11-10 | 2018-02-01 | H Lundbeck As | 2-Amino-3,5-difluoro-6-metil-6-fenil-3,4,5,6-tetrahidropiridinas en calidad de inhibidores de BACE1 para el tratamiento de la enfermedad de Alzheimer |
MA40941A (fr) | 2014-11-10 | 2017-09-19 | H Lundbeck As | 2-amino-5,5-difluoro-6-(fluorométhyl)-6-phényl-3,4,5,6-tétrahydropyridines comme inhibiteurs de bace1 |
JO3458B1 (ar) | 2014-11-10 | 2020-07-05 | H Lundbeck As | 2- أمينو-6- (دايفلوروميثيل) – 5، 5- ديفلورو-6-فينيل-3،4، 5، 6-تيتراهيدروبيريدين كمثبطات bace1 |
TW201717948A (zh) | 2015-08-10 | 2017-06-01 | H 朗德貝克公司 | 包括給予2-胺基-3,5,5-三氟-3,4,5,6-四氫吡啶的聯合治療 |
TW201718543A (zh) | 2015-08-12 | 2017-06-01 | H 朗德貝克公司 | 作爲bace1抑制劑之2-胺基-3-氟-3-(氟甲基)-6-甲基-6-苯基-3,4,5,6-四氫吡啶 |
JP7028780B2 (ja) * | 2015-09-30 | 2022-03-02 | シイエスピイシイ・チョンチ・ファーマシューティカル・テクノロジー・(シーチアチョワン)・カンパニー・リミテッド | ベンズアミド誘導体 |
DE102015120409A1 (de) | 2015-11-25 | 2017-01-12 | Miele & Cie. Kg | Kochfeld, insbesondere Induktionskochfeld |
DE102015120397A1 (de) | 2015-11-25 | 2017-01-05 | Miele & Cie. Kg | Kochfeld, insbesondere Induktionskochfeld |
US20190060286A1 (en) | 2016-02-29 | 2019-02-28 | University Of Florida Research Foundation, Incorpo | Chemotherapeutic Methods |
JP7204640B2 (ja) * | 2016-09-12 | 2023-01-16 | ニューラルステム・インコーポレーテッド | 糖尿病に関連する神経障害の改善 |
GB201713975D0 (en) | 2017-08-31 | 2017-10-18 | Macrophage Pharma Ltd | Medical use |
WO2019071147A1 (en) * | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | INHIBITORS OF KINASE P38 REDUCING EXPRESSION OF DUX4 GENE AND DOWNSTREAM GENES FOR THE TREATMENT OF FSHD |
US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
CN110678441B (zh) * | 2017-10-20 | 2023-03-31 | Sabic环球技术有限责任公司 | 用于制备二苯甲酸酯化合物如4-[苯甲酰(甲基)氨基]戊烷-2-基二苯甲酸酯的新合成方法 |
EP3727315B1 (en) | 2017-12-18 | 2021-10-13 | Unilever Global IP Limited | A topical composition comprising n-cyclopropyl nicotinamide |
CA3094324A1 (en) | 2018-03-26 | 2019-10-03 | Clear Creek Bio, Inc. | Compositions and methods for inhibiting dihydroorotate dehydrogenase |
TW202112368A (zh) | 2019-06-13 | 2021-04-01 | 荷蘭商法西歐知識產權股份有限公司 | 用於治療有關dux4表現之疾病的抑制劑組合 |
WO2021064186A1 (en) * | 2019-10-04 | 2021-04-08 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Novel pyridin-2(1h)one derivatives, their preparation and their use for the treatment of pain |
US12076315B2 (en) | 2020-03-20 | 2024-09-03 | Clear Creek Bio, Inc. | Stable polymorphic compositions of brequinar sodium and methods of use and manufacture thereof |
JP2024526998A (ja) | 2021-07-27 | 2024-07-19 | フルクラム セラピューティクス,インコーポレイテッド | ロスマピモドによる顔面肩甲上腕型筋ジストロフィーの治療 |
Family Cites Families (129)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3822277A (en) * | 1967-11-13 | 1974-07-02 | C Dufour | Certain pyridyl cyclopropylamides |
US4200750A (en) | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
JPS5651488A (en) | 1979-10-02 | 1981-05-09 | Meiji Seika Kaisha Ltd | Penicillin derivative and its preparation |
DE3332272A1 (de) * | 1983-09-07 | 1985-03-21 | Bayer Ag, 5090 Leverkusen | Herbizide mittel enthaltend metribuzin in kombination mit pyridincarbonsaeureamiden |
US4863940A (en) * | 1984-07-26 | 1989-09-05 | Rohm And Haas | N-acetonyl-substituted amides and phytopathogenic fungicidal use thereof |
EP0187284A3 (de) | 1984-12-20 | 1987-04-15 | Bayer Ag | Verfahren zur Herstellung von Pyridin-carbonsäure-N-tert.-alkylamiden |
DE3600288A1 (de) | 1986-01-08 | 1987-07-16 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonylharnstoff-derivaten |
DE3605423A1 (de) | 1986-02-20 | 1987-08-27 | Bayer Ag | Verfahren zur herstellung von pyridin-carbonsaeure-n-tert.-alkylamiden |
DE3618004A1 (de) | 1986-05-28 | 1987-12-03 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonyliso(thio)-harnstoff-derivaten |
JPH01102064A (ja) | 1987-10-16 | 1989-04-19 | Ishihara Sangyo Kaisha Ltd | ハロゲノピリジンカルボン酸アミド類の製造方法 |
DE3919348A1 (de) | 1988-06-16 | 1989-12-21 | Ciba Geigy Ag | Mikrobizide mittel |
MX16687A (es) | 1988-07-07 | 1994-01-31 | Ciba Geigy Ag | Compuestos de biarilo y procedimiento para su preparacion. |
JP2768721B2 (ja) * | 1989-03-01 | 1998-06-25 | 株式会社東芝 | 真空バルブ用接点材料 |
EP0430033A3 (en) | 1989-11-24 | 1991-09-11 | Ciba-Geigy Ag | Microbicidal agents |
US5166352A (en) * | 1991-09-12 | 1992-11-24 | Dowelanco | Pyridinecarboxylic acid chlorides from (trichloromethyl)pyridines |
DE69232003T2 (de) | 1991-09-18 | 2002-04-25 | Glaxo Group Ltd., Greenford | Benzanilidderivate als 5-HT1D-Antagonisten |
GB9119920D0 (en) | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
GB9816837D0 (en) | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
US5502194A (en) * | 1992-02-19 | 1996-03-26 | Bayer Aktiengesellschaft | Process for the preparation of 2-halogeno-pyridine derivatives |
US5246943A (en) | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
US5236934A (en) | 1992-08-26 | 1993-08-17 | E. I. Du Pont De Nemours And Company | 1,2,3,4-tetrahydroisoquinolines useful in the treatment of CNS disorders |
GB2273930A (en) | 1992-12-30 | 1994-07-06 | Glaxo Group Ltd | Benzanilide derivatives |
TW240217B (US07652168-20100126-C00055.png) | 1992-12-30 | 1995-02-11 | Glaxo Group Ltd | |
IL108630A0 (en) | 1993-02-18 | 1994-05-30 | Fmc Corp | Insecticidal substituted 2,4-diaminoquinazolines |
GB2276161A (en) | 1993-03-17 | 1994-09-21 | Glaxo Group Ltd | Aniline and benzanilide derivatives |
GB2276162A (en) | 1993-03-17 | 1994-09-21 | Glaxo Group Ltd | Aniline and benazilide derivatives |
AU686654B2 (en) | 1993-08-31 | 1998-02-12 | Pfizer Inc. | 5-arylindole derivatives |
WO1995006644A1 (en) | 1993-09-03 | 1995-03-09 | Smithkline Beecham Plc | Amide derivatives as 5ht1d receptor antagonists |
JPH09503773A (ja) | 1993-10-19 | 1997-04-15 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 5ht−1dレセプター拮抗剤用のベンズアニリド誘導体 |
AU1108395A (en) | 1993-12-07 | 1995-06-27 | Smithkline Beecham Plc | Heterocyclic biphenylylamides useful as 5ht1d antagonists |
GB9326008D0 (en) | 1993-12-21 | 1994-02-23 | Smithkline Beecham Plc | Novel compounds |
GB9408577D0 (en) | 1994-04-29 | 1994-06-22 | Fujisawa Pharmaceutical Co | New compound |
JPH09512804A (ja) | 1994-05-06 | 1997-12-22 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 5−ht1dアンタゴニストとして有用なビフェニルカルボキシアミド類 |
US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
GB2295387A (en) | 1994-11-23 | 1996-05-29 | Glaxo Inc | Quinazoline antagonists of alpha 1c adrenergic receptors |
WO1996031509A1 (en) | 1995-04-04 | 1996-10-10 | Glaxo Group Limited | IMIDAZO[1,2-a]PYRIDINE DERIVATIVES |
GB9507203D0 (en) | 1995-04-07 | 1995-05-31 | Smithkline Beecham Plc | Novel compounds |
IL118544A (en) | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
EP0842147A2 (en) | 1995-07-10 | 1998-05-20 | The Dow Chemical Company | Polynitrile oxides |
WO1997008133A1 (en) | 1995-08-22 | 1997-03-06 | Japan Tobacco Inc. | Amide compounds and use of the same |
US6080767A (en) | 1996-01-02 | 2000-06-27 | Aventis Pharmaceuticals Products Inc. | Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
US6323227B1 (en) | 1996-01-02 | 2001-11-27 | Aventis Pharmaceuticals Products Inc. | Substituted N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
KR19990077164A (ko) | 1996-01-11 | 1999-10-25 | 스티븐 베네티아너 | 신규 치환된 이미다졸 화합물 |
DE19608791A1 (de) | 1996-03-07 | 1997-09-11 | Hoechst Ag | Verfahren zur Herstellung von fluorierten Aromaten und fluorierten stickstoffhaltigen Heteroaromaten |
FR2754260B1 (fr) | 1996-10-04 | 1998-10-30 | Adir | Nouveaux derives substitues de biphenyle ou de phenylpyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
GB9614236D0 (en) * | 1996-07-06 | 1996-09-04 | Zeneca Ltd | Chemical compounds |
US5945418A (en) | 1996-12-18 | 1999-08-31 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
US6147080A (en) | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
US6087496A (en) | 1998-05-22 | 2000-07-11 | G. D. Searle & Co. | Substituted pyrazoles suitable as p38 kinase inhibitors |
EP0983260A2 (en) | 1997-05-22 | 2000-03-08 | G.D. Searle & Co. | 3(5)-HETEROARYL SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
CA2294057A1 (en) | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
US6060491A (en) | 1997-06-19 | 2000-05-09 | Dupont Pharmaceuticals | 6-membered aromatics as factor Xa inhibitors |
EP0993448A1 (en) | 1997-06-19 | 2000-04-19 | The Du Pont Merck Pharmaceutical Company | (AMIDINO)6-MEMBERED AROMATICS AS FACTOR Xa INHIBITORS |
WO1999001452A1 (en) | 1997-07-02 | 1999-01-14 | Smithkline Beecham Corporation | Novel cycloalkyl substituted imidazoles |
CN1155600C (zh) | 1997-09-05 | 2004-06-30 | 葛兰素集团有限公司 | 2,3-二芳基吡唑并[1,5-b]哒嗪衍生物,其制备方法和用作环氧酶2抑制剂 |
DK1042305T3 (da) | 1997-12-22 | 2005-09-19 | Bayer Pharmaceuticals Corp | Inhibering af p38-kinase ved anvendelse af symmetriske og asymmetriske diphenylurinstoffer |
JPH11218884A (ja) | 1998-02-03 | 1999-08-10 | Konica Corp | ハロゲン化銀写真感光材料 |
DE19817461A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Benzamide, deren Herstellung und Anwendung |
IL129596A (en) * | 1998-05-08 | 2003-10-31 | Dow Agrosciences Llc | Preparation of 2-substituted pyridines |
BR9910474A (pt) | 1998-05-15 | 2001-01-02 | Astrazeneca Ab | Composto derivado de amida, processo para preparação do mesmo, composição farmacêutica, e, uso de um composto derivado de amida |
US6448257B1 (en) | 1998-05-22 | 2002-09-10 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
US6130235A (en) | 1998-05-22 | 2000-10-10 | Scios Inc. | Compounds and methods to treat cardiac failure and other disorders |
US6867209B1 (en) | 1998-05-22 | 2005-03-15 | Scios, Inc. | Indole-type derivatives as inhibitors of p38 kinase |
EP1107758A2 (en) | 1998-08-28 | 2001-06-20 | Scios Inc. | Use of piperidines and/or piperazines as inhibitors of p38-alpha kinase |
US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
CA2337755C (en) | 1998-09-18 | 2008-07-29 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
WO2000026216A1 (en) | 1998-11-03 | 2000-05-11 | Glaxo Group Limited | Pyrazolopyridine derivatives as selective cox-2 inhibitors |
EP1140840B1 (en) | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
WO2000047553A2 (en) | 1999-02-11 | 2000-08-17 | Cor Therapeutics Inc. | ALKENYL AND ALKYNYL COMPOUNDS AS INHIBITORS OF FACTOR Xa |
JP2002538157A (ja) | 1999-02-27 | 2002-11-12 | グラクソ グループ リミテッド | ピラゾロピリジン |
GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
US6509361B1 (en) | 1999-05-12 | 2003-01-21 | Pharmacia Corporation | 1,5-Diaryl substituted pyrazoles as p38 kinase inhibitors |
AU5041300A (en) | 1999-05-24 | 2000-12-12 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
CA2374646A1 (en) | 1999-05-24 | 2000-11-30 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
JP2003500387A (ja) | 1999-05-24 | 2003-01-07 | シーオーアール セラピューティクス インコーポレイテッド | Xa因子の阻害剤 |
DE19932571A1 (de) | 1999-07-13 | 2001-01-18 | Clariant Gmbh | Verfahren zur Herstellung von Biarylen unter Palladophosphacyclobutan-Katalyse |
GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
US6576632B1 (en) | 1999-08-27 | 2003-06-10 | Pfizer Inc | Biaryl compounds useful as anticancer agents |
GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
SK9892001A3 (en) | 1999-11-10 | 2002-04-04 | Ortho Mcneil Pharm Inc | Substituted 2-aryl-3-(heteroaryl)-imidazo[1,2-a]pyrimidines, and related pharmaceutical compositions and methods |
US6303790B1 (en) * | 1999-11-29 | 2001-10-16 | Hoffman-La Roche Inc. | Process for the preparation of pyridine derivatives |
SE9904652D0 (sv) * | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
AR030053A1 (es) | 2000-03-02 | 2003-08-13 | Smithkline Beecham Corp | 1h-pirimido [4,5-d] pirimidin-2-onas y sales, composiciones farmaceuticas, uso para la fabricacion de un medicamento y procedimiento para producirlas |
US7235551B2 (en) * | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
WO2001070695A1 (en) | 2000-03-22 | 2001-09-27 | Vertex Pharmaceuticals Incorporated | Pyridine derivatives as inhibitors of p38 |
IL152893A0 (en) | 2000-05-18 | 2003-06-24 | Daiichi Seiyaku Co | Novel benzofuran derivatives |
PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
DK1333833T3 (da) | 2000-10-23 | 2011-12-12 | Glaxosmithkline Llc | Ny trisubstitueret 8H-pyridol[2,3-d]pyrimidin-7-on-forbindelse til behandling af CSBP/RK/p38-kinnasemedierede sygdomme |
NZ525334A (en) | 2000-11-17 | 2005-07-29 | Bristol Myers Squibb Co | Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors |
DE10059418A1 (de) | 2000-11-30 | 2002-06-20 | Aventis Pharma Gmbh | Ortho, meta-substituierte Bisarylverbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
DE10060807A1 (de) | 2000-12-07 | 2002-06-20 | Aventis Pharma Gmbh | Ortho, ortho-substituierte stickstoffhaltige Bisarylverbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
DE10063008A1 (de) | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
PL363959A1 (en) | 2001-03-09 | 2004-11-29 | Pfizer Products Inc. | Triazolopyridines as anti-inflammatory agents |
AUPR399301A0 (en) * | 2001-03-27 | 2001-04-26 | Silverbrook Research Pty. Ltd. | An apparatus and method(ART106) |
ATE438615T1 (de) | 2001-04-06 | 2009-08-15 | Biocryst Pharm Inc | Biarylverbindungen als serinproteaseinhibitoren |
US20020152397A1 (en) * | 2001-04-06 | 2002-10-17 | Mckay Drew | Virtual investigator |
FR2824827B1 (fr) | 2001-05-17 | 2004-02-13 | Fournier Lab Sa | Nouveaux derives de 5-phenyl-1h-indole antagoniste des recepteurs de l'interleukine-8 |
AR037233A1 (es) | 2001-09-07 | 2004-11-03 | Euro Celtique Sa | Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento |
GB0124848D0 (en) | 2001-10-16 | 2001-12-05 | Celltech R&D Ltd | Chemical compounds |
GB0124936D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124939D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124934D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124938D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124931D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124932D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124933D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
DK1474395T3 (da) | 2002-02-12 | 2008-02-11 | Smithkline Beecham Corp | Nicotinamidderivater, der er nyttige som p38-inhibitorer |
US20030225089A1 (en) | 2002-04-10 | 2003-12-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors |
GB0209891D0 (en) * | 2002-04-30 | 2002-06-05 | Glaxo Group Ltd | Novel compounds |
CA2489091A1 (en) | 2002-06-10 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Inhibitors against activation of nf-kappab |
GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
US20040038014A1 (en) * | 2002-08-20 | 2004-02-26 | Donaldson Company, Inc. | Fiber containing filter media |
US20040116479A1 (en) | 2002-10-04 | 2004-06-17 | Fortuna Haviv | Method of inhibiting angiogenesis |
DE10256052B4 (de) | 2002-11-30 | 2006-04-06 | A. Raymond & Cie | Abdeckvorrichtung für Montageaussparungen in den Abdeckleisten eines Fahrzeugdaches |
US7136850B2 (en) * | 2002-12-20 | 2006-11-14 | International Business Machines Corporation | Self tuning database retrieval optimization using regression functions |
GB0308185D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
GB0308186D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
GB0308201D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
ES2315703T3 (es) | 2003-07-25 | 2009-04-01 | Novartis Ag | Inhibidores de la quinasa p-38. |
GB0318814D0 (en) * | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
GB0402143D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
GB0402140D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
GB0402138D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
GB0402137D0 (en) | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
UA90864C2 (en) * | 2004-09-09 | 2010-06-10 | Ромарк Лебораториз, Л.К. | Halogenated benzamide derivatives |
AR053450A1 (es) | 2005-03-25 | 2007-05-09 | Glaxo Group Ltd | Derivados de 3,4-dihidro-pirimido(4,5-d)pirimidin-2-(1h)-ona 1,5,7 trisustituidos como inhibidores de la quinasa p38 |
GB0612026D0 (en) * | 2006-06-16 | 2006-07-26 | Smithkline Beecham Corp | New use |
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