JP2005539054A5 - - Google Patents
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- Publication number
- JP2005539054A5 JP2005539054A5 JP2004533319A JP2004533319A JP2005539054A5 JP 2005539054 A5 JP2005539054 A5 JP 2005539054A5 JP 2004533319 A JP2004533319 A JP 2004533319A JP 2004533319 A JP2004533319 A JP 2004533319A JP 2005539054 A5 JP2005539054 A5 JP 2005539054A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- hydrogen atom
- disease
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- -1 nitro, amino Chemical group 0.000 claims description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical compound OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical compound O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 238000000034 method Methods 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 3
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- IGAVZWMNOPFOCW-UHFFFAOYSA-N 2h-1,2,4-thiadiazol-5-one Chemical compound O=C1NC=NS1 IGAVZWMNOPFOCW-UHFFFAOYSA-N 0.000 claims 2
- WTSXVIMLKCKWIW-UHFFFAOYSA-N 3h-1,3,4-oxadiazol-2-one Chemical compound O=C1NN=CO1 WTSXVIMLKCKWIW-UHFFFAOYSA-N 0.000 claims 2
- YSVFAMDLJASIGW-UHFFFAOYSA-N 5h-1,2,3,5-oxathiadiazole 2-oxide Chemical compound O=S1NC=NO1 YSVFAMDLJASIGW-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- QTMQRWPEJWOKKV-QFIPXVFZSA-N (2s)-2-[[2-[2-(methylamino)pyrimidin-4-yl]-1h-indole-5-carbonyl]amino]-3-(n-[4-(trifluoromethyl)pyrimidin-2-yl]anilino)propanoic acid Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)N[C@@H](CN(C=2C=CC=CC=2)C=2N=C(C=CN=2)C(F)(F)F)C(O)=O)=N1 QTMQRWPEJWOKKV-QFIPXVFZSA-N 0.000 claims 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- RKPNOOCIENNLRT-SANMLTNESA-N 2-[2-(methylamino)pyrimidin-4-yl]-n-[(1s)-1-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-2-(n-phenylanilino)ethyl]-1h-indole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)N[C@@H](CN(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2OC(=O)NN=2)=N1 RKPNOOCIENNLRT-SANMLTNESA-N 0.000 claims 1
- GUKQDNOHRYSDSQ-DEOSSOPVSA-N 2-[2-(methylamino)pyrimidin-4-yl]-n-[(1s)-1-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-2-(n-pyridin-2-ylanilino)ethyl]-1h-indole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)N[C@@H](CN(C=2C=CC=CC=2)C=2N=CC=CC=2)C=2OC(=O)NN=2)=N1 GUKQDNOHRYSDSQ-DEOSSOPVSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000036487 Arthropathies Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000017667 Chronic Disease Diseases 0.000 claims 1
- 102000008186 Collagen Human genes 0.000 claims 1
- 108010035532 Collagen Proteins 0.000 claims 1
- 208000027932 Collagen disease Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 206010014824 Endotoxic shock Diseases 0.000 claims 1
- 230000005526 G1 to G0 transition Effects 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 102000001284 I-kappa-B kinase Human genes 0.000 claims 1
- 108060006678 I-kappa-B kinase Proteins 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010022714 Intestinal ulcer Diseases 0.000 claims 1
- 208000012659 Joint disease Diseases 0.000 claims 1
- 206010024229 Leprosy Diseases 0.000 claims 1
- 206010065433 Ligament rupture Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 208000029578 Muscle disease Diseases 0.000 claims 1
- 208000021642 Muscular disease Diseases 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000031481 Pathologic Constriction Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000026816 acute arthritis Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- 208000037873 arthrodesis Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000004097 bone metabolism Effects 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 210000000845 cartilage Anatomy 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000017760 chronic graft versus host disease Diseases 0.000 claims 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
- 229920001436 collagen Polymers 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 210000002808 connective tissue Anatomy 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 238000001212 derivatisation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000003137 locomotive effect Effects 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000005499 meniscus Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000013465 muscle pain Diseases 0.000 claims 1
- 230000003387 muscular Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- ZFJWJZBTDLNTKE-DEOSSOPVSA-N n-[(2s)-1-amino-1-oxo-3-(n-phenylanilino)propan-2-yl]-2-[2-(methylamino)pyrimidin-4-yl]-3h-benzimidazole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3N=2)C(=O)N[C@@H](CN(C=2C=CC=CC=2)C=2C=CC=CC=2)C(N)=O)=N1 ZFJWJZBTDLNTKE-DEOSSOPVSA-N 0.000 claims 1
- OTDFHGPXTVLARR-UHFFFAOYSA-N n-[1-(2-hydroxyethylamino)-1-oxo-3-(n-pyrimidin-2-ylanilino)propan-2-yl]-2-[2-(methylamino)pyrimidin-4-yl]-1h-indole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)NC(CN(C=2C=CC=CC=2)C=2N=CC=CN=2)C(=O)NCCO)=N1 OTDFHGPXTVLARR-UHFFFAOYSA-N 0.000 claims 1
- HKIZECAQMBNNHW-UHFFFAOYSA-N n-[1-amino-1-oxo-3-(n-pyridin-2-ylanilino)propan-2-yl]-2-(2-aminopyrimidin-4-yl)-1h-indole-5-carboxamide Chemical compound C=1C=C2NC(C=3N=C(N)N=CC=3)=CC2=CC=1C(=O)NC(C(=O)N)CN(C=1N=CC=CC=1)C1=CC=CC=C1 HKIZECAQMBNNHW-UHFFFAOYSA-N 0.000 claims 1
- ZYRRVNPCRCRJFC-UHFFFAOYSA-N n-[1-amino-3-(4-fluoro-n-(5-methylpyrimidin-2-yl)anilino)-1-oxopropan-2-yl]-2-[2-(methylamino)pyrimidin-4-yl]-1h-indole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)NC(CN(C=2C=CC(F)=CC=2)C=2N=CC(C)=CN=2)C(N)=O)=N1 ZYRRVNPCRCRJFC-UHFFFAOYSA-N 0.000 claims 1
- WTWJEDVYBZQJOR-UHFFFAOYSA-N n-[1-amino-3-(4-fluoro-n-pyridin-2-ylanilino)-1-oxopropan-2-yl]-2-(2-aminopyrimidin-4-yl)-1h-indole-5-carboxamide Chemical compound C=1C=C2NC(C=3N=C(N)N=CC=3)=CC2=CC=1C(=O)NC(C(=O)N)CN(C=1N=CC=CC=1)C1=CC=C(F)C=C1 WTWJEDVYBZQJOR-UHFFFAOYSA-N 0.000 claims 1
- VQMWAZJBSLIMHQ-UHFFFAOYSA-N n-[1-amino-3-(4-fluoro-n-pyridin-2-ylanilino)-1-oxopropan-2-yl]-2-[2-(methylamino)pyrimidin-4-yl]-1h-indole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)NC(CN(C=2C=CC(F)=CC=2)C=2N=CC=CC=2)C(N)=O)=N1 VQMWAZJBSLIMHQ-UHFFFAOYSA-N 0.000 claims 1
- GQDXCMPDYMUTQU-UHFFFAOYSA-N n-[2-(4-fluoro-n-pyridin-2-ylanilino)-1-(1h-1,2,4-triazol-5-yl)ethyl]-2-[2-(methylamino)pyrimidin-4-yl]-1h-indole-5-carboxamide Chemical compound CNC1=NC=CC(C=2NC3=CC=C(C=C3C=2)C(=O)NC(CN(C=2C=CC(F)=CC=2)C=2N=CC=CC=2)C=2NC=NN=2)=N1 GQDXCMPDYMUTQU-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
- 210000004417 patella Anatomy 0.000 claims 1
- 208000028169 periodontal disease Diseases 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000036262 stenosis Effects 0.000 claims 1
- 208000037804 stenosis Diseases 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 241000701161 unidentified adenovirus Species 0.000 claims 1
- 241001529453 unidentified herpesvirus Species 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10237722A DE10237722A1 (de) | 2002-08-17 | 2002-08-17 | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
| PCT/EP2003/008629 WO2004022553A1 (de) | 2002-08-17 | 2003-08-05 | INDOL-ODER BENZIMIDAZOLDERIVATE ZUR MODULATION DER IλB-KINASE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005539054A JP2005539054A (ja) | 2005-12-22 |
| JP2005539054A5 true JP2005539054A5 (enExample) | 2010-04-22 |
| JP4504812B2 JP4504812B2 (ja) | 2010-07-14 |
Family
ID=31968974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004533319A Expired - Fee Related JP4504812B2 (ja) | 2002-08-17 | 2003-08-05 | ＩκＢキナーゼをモジュレートするためのインドール誘導体またはベンズイミダゾール誘導体 |
Country Status (42)
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19951360A1 (de) * | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
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| US7462638B2 (en) * | 2002-08-17 | 2008-12-09 | Sanofi-Aventis Deutschland Gmbh | Use of IκB-kinase inhibitors in pain therapy |
| DE10237722A1 (de) * | 2002-08-17 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
| US7046741B2 (en) * | 2004-04-16 | 2006-05-16 | Data Flow Technologies, Inc. | Single and multiple sinewave modulation and demodulation techniques, apparatus, and communications systems |
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