JP2005529842A5 - - Google Patents
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- Publication number
- JP2005529842A5 JP2005529842A5 JP2003541836A JP2003541836A JP2005529842A5 JP 2005529842 A5 JP2005529842 A5 JP 2005529842A5 JP 2003541836 A JP2003541836 A JP 2003541836A JP 2003541836 A JP2003541836 A JP 2003541836A JP 2005529842 A5 JP2005529842 A5 JP 2005529842A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- substituted
- unsubstituted
- group
- 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
- 125000001424 substituent group Chemical group 0.000 claims 237
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 125
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 116
- 125000000217 alkyl group Chemical group 0.000 claims 104
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 60
- 150000003254 radicals Chemical class 0.000 claims 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 46
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 40
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 40
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 40
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 40
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 40
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 40
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 40
- 239000008194 pharmaceutical composition Substances 0.000 claims 35
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 21
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 20
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 20
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 20
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 20
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 20
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 20
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 20
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 20
- 229930192474 thiophene Natural products 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 17
- 125000006413 ring segment Chemical group 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- -1 —CF 3 Chemical group 0.000 claims 12
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 10
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 102000001284 I-kappa-B kinase Human genes 0.000 claims 5
- 108060006678 I-kappa-B kinase Proteins 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 208000034578 Multiple myelomas Diseases 0.000 claims 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 230000010261 cell growth Effects 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- JZRMBDHPALEPDM-UHFFFAOYSA-N N-(6-Chloro-9H-pyrido[3,4-b]indol-8-yl)-3-pyridinecarboxamide Chemical compound C=12NC3=CN=CC=C3C2=CC(Cl)=CC=1NC(=O)C1=CC=CN=C1 JZRMBDHPALEPDM-UHFFFAOYSA-N 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34491101P | 2001-11-07 | 2001-11-07 | |
| PCT/US2002/035645 WO2003039545A2 (en) | 2001-11-07 | 2002-11-06 | Carboline derivatives as inhibitors of ikb in the treatment of multiple myeloma and others cancers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009262389A Division JP2010031061A (ja) | 2001-11-07 | 2009-11-17 | 多発性骨髄腫および他の癌の処置におけるＩκＢのインヒビターとしてのカルボリン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005529842A JP2005529842A (ja) | 2005-10-06 |
| JP2005529842A5 true JP2005529842A5 (https=) | 2006-01-05 |
| JP4599501B2 JP4599501B2 (ja) | 2010-12-15 |
Family
ID=23352621
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003541836A Expired - Fee Related JP4599501B2 (ja) | 2001-11-07 | 2002-11-06 | 多発性骨髄腫および他の癌の処置におけるＩκＢのインヒビターとしてのカルボリン誘導体 |
| JP2009262389A Withdrawn JP2010031061A (ja) | 2001-11-07 | 2009-11-17 | 多発性骨髄腫および他の癌の処置におけるＩκＢのインヒビターとしてのカルボリン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009262389A Withdrawn JP2010031061A (ja) | 2001-11-07 | 2009-11-17 | 多発性骨髄腫および他の癌の処置におけるＩκＢのインヒビターとしてのカルボリン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9248124B2 (https=) |
| EP (1) | EP1443927B1 (https=) |
| JP (2) | JP4599501B2 (https=) |
| AU (1) | AU2002352498A1 (https=) |
| DE (1) | DE60217532T8 (https=) |
| WO (1) | WO2003039545A2 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9248124B2 (en) * | 2001-11-07 | 2016-02-02 | Millennium Pharmaceuticals, Inc. | Use of inhibitors of IκB kinase for the treatment of cancer |
| USRE48890E1 (en) | 2002-05-17 | 2022-01-11 | Celgene Corporation | Methods for treating multiple myeloma with 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione after stem cell transplantation |
| US7968569B2 (en) * | 2002-05-17 | 2011-06-28 | Celgene Corporation | Methods for treatment of multiple myeloma using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| US7393862B2 (en) | 2002-05-17 | 2008-07-01 | Celgene Corporation | Method using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for treatment of certain leukemias |
| WO2004041285A1 (en) | 2002-10-31 | 2004-05-21 | Amgen Inc. | Antiinflammation agents |
| BRPI0409263A (pt) * | 2003-04-09 | 2006-03-28 | Millennium Pharm Inc | composto; composição farmacêutica; método para tratar uma doença mediada por ikk e método para inibir ikk em um paciente que dele necessita |
| DE10326821A1 (de) * | 2003-06-11 | 2005-01-05 | Medical Enzymes Ag | Pharmazeutische Kombinationspräparate zur Krebstherapie |
| BRPI0509660A (pt) | 2004-04-09 | 2007-10-09 | Millennium Pharm Inc | compostos de beta-carbolina de utilidade no tratamento de doenças inflamatórias |
| CN100443178C (zh) | 2006-03-10 | 2008-12-17 | 中国石油天然气股份有限公司 | 一种乙烯低聚的催化剂组合物及其应用 |
| EP2001455A2 (en) | 2006-03-15 | 2008-12-17 | Theralogics, Inc. | Methods of treating muscular wasting diseases using nf-kb activation inhibitors |
| US8546322B2 (en) | 2007-08-03 | 2013-10-01 | The Regents Of The University Of California | Inhibitors of intracellular urokinase plasminogen activator and methods of use thereof |
| US20090137579A1 (en) * | 2007-10-23 | 2009-05-28 | 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 |
| TWI466886B (zh) * | 2008-06-11 | 2015-01-01 | Genentech Inc | 二氮雜咔唑及使用方法 |
| EP2161271A1 (en) * | 2008-09-08 | 2010-03-10 | Università Degli Studi Di Milano - Bicocca | Alpha-carboline inhibitors of NMP-ALK, RET, and Bcr-Abl |
| WO2010099445A2 (en) * | 2009-02-26 | 2010-09-02 | Board Of Trustees Of Michigan State University | Non-covalent inhibition of the 26s proteasome and uses thereof |
| FR2953837B1 (fr) * | 2009-12-10 | 2012-03-09 | Sanofi Aventis | Derives 9h-pyridino[3,4-b]indole disubstitues, leur preparation et leur utilisation therapeutique |
| FR2953838B1 (fr) * | 2009-12-10 | 2012-02-24 | Sanofi Aventis | Derives de 9h-beta-carboline (ou 9h-pyridino[3,4-b]indole) trisubstitues, leur preparation et leur utilisation therapeutique |
| US20110183938A1 (en) | 2009-12-16 | 2011-07-28 | Genentech, Inc. | 1,7-diazacarbazoles and methods of use |
| EP3318563A1 (en) | 2016-11-07 | 2018-05-09 | Sanofi | Substituted pyrido[3,4-b]indoles for the treatment of cartilage disorders |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2303627B (en) | 1995-07-26 | 1997-07-09 | Arab Pharmaceutical Mfg Co Ltd | Anti-tumour platinum-harmine complex |
| AU741271B2 (en) * | 1997-09-10 | 2001-11-29 | Uab Research Foundation | Regulation of osteoclast formation by inhibition of osteoblastic stem cell factor |
| JPH11180873A (ja) * | 1997-12-22 | 1999-07-06 | Kaken Shoyaku Kk | ＮＦ−κＢ活性阻害剤 |
| DE19807993A1 (de) * | 1998-02-26 | 1999-09-02 | Bayer Ag | Verwendung von ß-Carbolinderivaten zur Bekämpfung von TNF-alpha-abhängigen Krankheiten |
| HUP0102782A3 (en) | 1998-06-19 | 2002-12-28 | Smithkline Beecham Corp | Salycilanilide as inhibitors of transcription factor nf-kb |
| DE19951360A1 (de) | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| HK1054039B (zh) * | 2000-03-15 | 2010-04-16 | 萨诺费－阿文蒂斯德国有限公司 | 取代的β-咔啉 |
| EP1268477B1 (en) | 2000-03-15 | 2010-04-21 | Sanofi-Aventis Deutschland GmbH | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| US9248124B2 (en) * | 2001-11-07 | 2016-02-02 | Millennium Pharmaceuticals, Inc. | Use of inhibitors of IκB kinase for the treatment of cancer |
-
2002
- 2002-11-06 US US10/495,041 patent/US9248124B2/en not_active Expired - Fee Related
- 2002-11-06 JP JP2003541836A patent/JP4599501B2/ja not_active Expired - Fee Related
- 2002-11-06 AU AU2002352498A patent/AU2002352498A1/en not_active Abandoned
- 2002-11-06 WO PCT/US2002/035645 patent/WO2003039545A2/en not_active Ceased
- 2002-11-06 EP EP02789471A patent/EP1443927B1/en not_active Expired - Lifetime
- 2002-11-06 DE DE60217532T patent/DE60217532T8/de active Active
-
2009
- 2009-11-17 JP JP2009262389A patent/JP2010031061A/ja not_active Withdrawn
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