JP2003527394A5 - - Google Patents
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- JP2003527394A5 JP2003527394A5 JP2001567739A JP2001567739A JP2003527394A5 JP 2003527394 A5 JP2003527394 A5 JP 2003527394A5 JP 2001567739 A JP2001567739 A JP 2001567739A JP 2001567739 A JP2001567739 A JP 2001567739A JP 2003527394 A5 JP2003527394 A5 JP 2003527394A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- mono
- unsubstituted
- independently
- 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
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 103
- 125000000217 alkyl group Chemical group 0.000 description 86
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 65
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 60
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 40
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 40
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 40
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 40
- 125000001424 substituent group Chemical group 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 26
- 125000000623 heterocyclic group Chemical group 0.000 description 24
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 22
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 description 22
- 229910052736 halogen Inorganic materials 0.000 description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 20
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 20
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 20
- 150000002367 halogens Chemical class 0.000 description 20
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 20
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 20
- 125000006413 ring segment Chemical group 0.000 description 20
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 20
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 125000004076 pyridyl group Chemical group 0.000 description 14
- 229930192474 thiophene Natural products 0.000 description 14
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- -1 cyano, nitro, amino Chemical group 0.000 description 11
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- 239000007995 HEPES buffer Substances 0.000 description 5
- 208000030507 AIDS Diseases 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 108091000080 Phosphotransferase Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 102000020233 phosphotransferase Human genes 0.000 description 4
- 206010006895 Cachexia Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 3
- 206010040070 Septic Shock Diseases 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 208000014644 Brain disease Diseases 0.000 description 2
- KJYPVSFWDLYFIA-UHFFFAOYSA-N COC1=C(C=CC2=C1N(C3=C2C=CN=C3)N)Cl Chemical compound COC1=C(C=CC2=C1N(C3=C2C=CN=C3)N)Cl KJYPVSFWDLYFIA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 208000000059 Dyspnea Diseases 0.000 description 2
- 206010013975 Dyspnoeas Diseases 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 206010061289 metastatic neoplasm Diseases 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- UAIUNKRWKOVEES-UHFFFAOYSA-N 3,3',5,5'-tetramethylbenzidine Chemical compound CC1=C(N)C(C)=CC(C=2C=C(C)C(N)=C(C)C=2)=C1 UAIUNKRWKOVEES-UHFFFAOYSA-N 0.000 description 1
- UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 1
- CZIASKQYBGOYRW-UHFFFAOYSA-N 7-chloro-8-methoxy-9-nitropyrido[3,4-b]indole Chemical compound C12=CC=NC=C2N([N+]([O-])=O)C2=C1C=CC(Cl)=C2OC CZIASKQYBGOYRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 0 CC(*(*)C1=C2C(*)C(*=C)*=C1*)=C2[Cn] Chemical compound CC(*(*)C1=C2C(*)C(*=C)*=C1*)=C2[Cn] 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 1
- 208000037487 Endotoxemia Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 206010018634 Gouty Arthritis Diseases 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 206010023330 Keloid scar Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010027236 Meningitis fungal Diseases 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 101150091206 Nfkbia gene Proteins 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 206010048873 Traumatic arthritis Diseases 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 208000019664 bone resorption disease Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 201000010056 fungal meningitis Diseases 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009772 tissue formation Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00105514.4 | 2000-03-15 | ||
| EP00105514A EP1134221A1 (en) | 2000-03-15 | 2000-03-15 | Substituted beta-carbolines as lkB kinase inhibitors |
| EP00125169.3 | 2000-11-18 | ||
| EP00125169A EP1209158A1 (en) | 2000-11-18 | 2000-11-18 | Substituted beta-carbolines |
| PCT/EP2001/002237 WO2001068648A1 (en) | 2000-03-15 | 2001-02-28 | Substituted beta-carbolines with ikb-kinase inhibiting activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003527394A JP2003527394A (ja) | 2003-09-16 |
| JP2003527394A5 true JP2003527394A5 (https=) | 2008-04-10 |
| JP5000828B2 JP5000828B2 (ja) | 2012-08-15 |
Family
ID=26070675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001567739A Expired - Fee Related JP5000828B2 (ja) | 2000-03-15 | 2001-02-28 | ＩｋＢキナーゼ阻害活性を有する置換ベーターカルボリン |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US6627637B2 (https=) |
| JP (1) | JP5000828B2 (https=) |
| KR (1) | KR100826817B1 (https=) |
| CN (1) | CN100509810C (https=) |
| AT (1) | ATE465161T1 (https=) |
| AU (2) | AU3741801A (https=) |
| BR (1) | BR0109161A (https=) |
| CA (1) | CA2402549A1 (https=) |
| CZ (1) | CZ301077B6 (https=) |
| DE (1) | DE60141895D1 (https=) |
| EE (1) | EE200200523A (https=) |
| HK (1) | HK1054039B (https=) |
| HR (1) | HRP20020748A2 (https=) |
| HU (1) | HUP0300894A3 (https=) |
| IL (2) | IL151695A0 (https=) |
| ME (1) | MEP28108A (https=) |
| MX (1) | MXPA02007981A (https=) |
| NO (1) | NO324248B1 (https=) |
| NZ (1) | NZ521386A (https=) |
| PL (1) | PL357284A1 (https=) |
| RU (1) | RU2277095C2 (https=) |
| SK (1) | SK13082002A3 (https=) |
| YU (1) | YU65502A (https=) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0300894A3 (en) * | 2000-03-15 | 2008-05-28 | Sanofi Aventis Deutschland | Substituted beta-carbolines, process for their preparation, pharmaceutical compositions containing them and their use |
| MXPA03006817A (es) * | 2001-02-01 | 2003-11-13 | Bristol Myers Squibb Co | Metodo de tratamiento de enfermedades inflamatorias e inmunes usando inhibidores de la ikb cinasa (ikk). |
| DE60217532T8 (de) * | 2001-11-07 | 2008-02-07 | Millennium Pharmaceuticals, Inc., Cambridge | Carboline derivate als ikb-inhibitoren zur behandlung des m ultiplen myelomas |
| US7462638B2 (en) * | 2002-08-17 | 2008-12-09 | Sanofi-Aventis Deutschland Gmbh | Use of IκB-kinase inhibitors in pain therapy |
| US20040166095A1 (en) * | 2003-02-25 | 2004-08-26 | Blazar Bruce R. | Methods for preventing GVHD |
| AU2004230952A1 (en) * | 2003-04-09 | 2004-10-28 | Millenium Pharmaceuticals, Inc. | Beta-carbolines useful for treating inflammatory disease |
| MXPA06011545A (es) * | 2004-04-09 | 2007-03-26 | Millennium Pharm Inc | Beta-carbolinas utiles para el tratamiento de enfermedades inflamatorias. |
| EP2308839B1 (en) * | 2005-04-20 | 2017-03-01 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US8518964B2 (en) | 2005-11-22 | 2013-08-27 | Merck Sharp & Dohme Corp. | Tricyclic compounds useful as inhibitors of kinases |
| WO2009054970A1 (en) * | 2007-10-23 | 2009-04-30 | Millennium Pharmaceuticals, Inc. | Mesylate salt of an ikk inhibitor |
| US20090131422A1 (en) * | 2007-10-23 | 2009-05-21 | Millennium Pharmaceuticals, Inc. | Salts of an IKK inhibitor |
| BRPI0821209A2 (pt) * | 2007-12-19 | 2019-09-24 | Amgen Inc | composto, composição farmacêutica, métodos de tratar câncer, para reduzir o tamanho de tumor, para tratar distúrbios, e para reduzir metástase em um tumor. |
| US8716308B2 (en) | 2008-01-11 | 2014-05-06 | Albany Molecular Research, Inc. | (1-azinone)-substituted pyridoindoles |
| CN101245066B (zh) * | 2008-01-23 | 2010-11-10 | 复旦大学 | 一种制备7-烷氧基-2,9-二氮芴衍生物的方法 |
| US8389533B2 (en) * | 2008-04-07 | 2013-03-05 | Amgen Inc. | Gem-disubstituted and spirocyclic amino pyridines/pyrimidines as cell cycle inhibitors |
| US20110111417A1 (en) | 2008-05-14 | 2011-05-12 | Millennium Pharmaceuticals, Inc. | Methods and kits for monitoring the effects of immunomodulators on adaptive immunity |
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- 2001-02-28 AU AU2001237418A patent/AU2001237418B2/en not_active Ceased
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