JP2004536869A - 新規化合物 - Google Patents
新規化合物 Download PDFInfo
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- JP2004536869A JP2004536869A JP2003515522A JP2003515522A JP2004536869A JP 2004536869 A JP2004536869 A JP 2004536869A JP 2003515522 A JP2003515522 A JP 2003515522A JP 2003515522 A JP2003515522 A JP 2003515522A JP 2004536869 A JP2004536869 A JP 2004536869A
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- Prior art keywords
- formula
- compound
- amino
- aminocarbonyl
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 93
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 23
- -1 cyano, hydroxyl Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 18
- 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 claims description 17
- 101710205525 Inhibitor of nuclear factor kappa-B kinase subunit beta Proteins 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 15
- 230000005764 inhibitory process Effects 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 239000011593 sulfur Substances 0.000 claims description 4
- QRWXQTUTFBGJHU-UHFFFAOYSA-N 2-(carbamoylamino)-5-(1h-indol-3-yl)-4-methylthiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C1=CNC2=CC=CC=C12 QRWXQTUTFBGJHU-UHFFFAOYSA-N 0.000 claims description 3
- DTGUWAQNQUYFQF-UHFFFAOYSA-N 2-(carbamoylamino)-5-(1h-indol-5-yl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=C3C=CNC3=CC=2)=C1 DTGUWAQNQUYFQF-UHFFFAOYSA-N 0.000 claims description 3
- SWVARBRJKGYPIV-UHFFFAOYSA-N 2-(carbamoylamino)-5-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methylthiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C1=CC=C(OCCO2)C2=C1 SWVARBRJKGYPIV-UHFFFAOYSA-N 0.000 claims description 3
- HYLSCTUBXRDDOD-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(2-morpholin-4-ylethoxy)-1-benzothiophen-2-yl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2SC3=CC=CC(OCCN4CCOCC4)=C3C=2)=C1 HYLSCTUBXRDDOD-UHFFFAOYSA-N 0.000 claims description 3
- ACPLTAYZHQVNHA-UHFFFAOYSA-N 2-(carbamoylamino)-5-quinolin-3-ylthiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=C3C=CC=CC3=NC=2)=C1 ACPLTAYZHQVNHA-UHFFFAOYSA-N 0.000 claims description 3
- JTXJRZUQPFHBOL-UHFFFAOYSA-N 2-(carbamoylamino)-5-quinolin-8-ylthiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C3=NC=CC=C3C=CC=2)=C1 JTXJRZUQPFHBOL-UHFFFAOYSA-N 0.000 claims description 3
- LQMABRNIZVPJKS-UHFFFAOYSA-N 5-(1-benzofuran-2-yl)-2-(carbamoylamino)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2OC3=CC=CC=C3C=2)=C1 LQMABRNIZVPJKS-UHFFFAOYSA-N 0.000 claims description 3
- IEMLTPOVTUCHJA-UHFFFAOYSA-N 5-(1-benzothiophen-2-yl)-2-(carbamoylamino)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2SC3=CC=CC=C3C=2)=C1 IEMLTPOVTUCHJA-UHFFFAOYSA-N 0.000 claims description 3
- LWXZDSSKXHVDRF-UHFFFAOYSA-N 5-(1-benzothiophen-3-yl)-2-(carbamoylamino)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C3=CC=CC=C3SC=2)=C1 LWXZDSSKXHVDRF-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 108010057466 NF-kappa B Proteins 0.000 description 19
- 102000003945 NF-kappa B Human genes 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 13
- 239000002953 phosphate buffered saline Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 9
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 9
- 229940098773 bovine serum albumin Drugs 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229920000136 polysorbate Polymers 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 108091000080 Phosphotransferase Proteins 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- YEENEYXBHNNNGV-XEHWZWQGSA-M sodium;3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoate;(2r,3r,4s,5s,6r)-2-[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound [Na+].CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I.O[C@H]1[C@H](O)[C@@H](CO)O[C@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 YEENEYXBHNNNGV-XEHWZWQGSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102617A SE0102617D0 (sv) | 2001-07-25 | 2001-07-25 | Novel compounds |
| PCT/SE2002/001402 WO2003010163A1 (en) | 2001-07-25 | 2002-07-19 | Novel compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009291103A Division JP2010111683A (ja) | 2001-07-25 | 2009-12-22 | 新規化合物 |
Publications (2)
| Publication Number | Publication Date |
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| JP2004536869A true JP2004536869A (ja) | 2004-12-09 |
| JP2004536869A5 JP2004536869A5 (https=) | 2009-09-03 |
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| JP2003515522A Withdrawn JP2004536869A (ja) | 2001-07-25 | 2002-07-19 | 新規化合物 |
| JP2009291103A Pending JP2010111683A (ja) | 2001-07-25 | 2009-12-22 | 新規化合物 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009291103A Pending JP2010111683A (ja) | 2001-07-25 | 2009-12-22 | 新規化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7098240B2 (https=) |
| EP (1) | EP1421079B1 (https=) |
| JP (2) | JP2004536869A (https=) |
| KR (1) | KR20040018521A (https=) |
| CN (1) | CN1538968A (https=) |
| AT (1) | ATE353327T1 (https=) |
| BR (1) | BR0211472A (https=) |
| CA (1) | CA2454702A1 (https=) |
| DE (1) | DE60218048T2 (https=) |
| ES (1) | ES2280559T3 (https=) |
| IL (1) | IL160023A0 (https=) |
| MX (1) | MXPA04000755A (https=) |
| NO (1) | NO20040314L (https=) |
| NZ (1) | NZ530751A (https=) |
| SE (1) | SE0102617D0 (https=) |
| WO (1) | WO2003010163A1 (https=) |
| ZA (1) | ZA200400494B (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008087933A1 (ja) * | 2007-01-15 | 2008-07-24 | Santen Pharmaceutical Co., Ltd. | ＩκＢキナーゼβ阻害活性を有する新規インドール誘導体 |
| WO2010024227A1 (ja) * | 2008-08-25 | 2010-03-04 | 参天製薬株式会社 | ウレイド基、アミノカルボニル基及び置換基を有してもよい二環式基を置換基として有する新規ピロール誘導体 |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0003154D0 (en) * | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| CN101624391A (zh) * | 2001-06-11 | 2010-01-13 | 病毒化学医药公司 | 用作黄病毒感染抗病毒剂的噻吩衍生物 |
| SE0102616D0 (sv) * | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| DE60229975D1 (de) * | 2001-10-04 | 2009-01-02 | Smithkline Beecham Corp | Nf-kb-inhibitoren |
| AU2003249683A1 (en) * | 2002-06-06 | 2003-12-22 | Smithkline Beecham Corporation | Nf-:b inhibitors |
| US7402608B2 (en) * | 2002-12-10 | 2008-07-22 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| SE0300092D0 (sv) | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| SE0300091D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| US7429603B2 (en) * | 2003-04-25 | 2008-09-30 | 3-Dimensional Pharmaceuticals, Inc. | C-fms kinase inhibitors |
| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| US7427683B2 (en) * | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
| US7790724B2 (en) | 2003-04-25 | 2010-09-07 | Janssen Pharmaceutica N.V. | c-fms kinase inhibitors |
| EP1493739A1 (fr) * | 2003-07-03 | 2005-01-05 | Warner-Lambert Company LLC | Dérivés thiophényliques d'aminoacides, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| US20050085531A1 (en) * | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| BRPI0418351A (pt) * | 2004-01-05 | 2007-05-08 | Astrazeneca Ab | composto ou um sal farmaceuticamente aceitável do mesmo, métodos de limitar a proliferação celular em um humano ou animal, de tratamento de um humano ou animal sofrendo de cáncer, de tratamento de profilaxia de cáncer, de tratamento de um humano ou animal sofrendo de uma doença neoplásica, de tratamento de um humano ou animal sofrendo de uma doença prolifetativa de tratamento de cáncer, para o tratamento de infecções associadas com cáncer, para o tratamento profilático de infecções associadas com cáncer, composição farmacêutica, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, método de inibir a chk1 quinase, e, processo para a preparação de um composto ou um sal farmaceuticamente aceitável do mesmo |
| AR050253A1 (es) | 2004-06-24 | 2006-10-11 | Smithkline Beecham Corp | Compuesto derivado de indazol carboxamida, composicion que lo comprende y su uso para la preparacion de un medicamento |
| TW200626142A (en) | 2004-09-21 | 2006-08-01 | Glaxo Group Ltd | Chemical compounds |
| BRPI0610283A2 (pt) * | 2005-05-13 | 2010-10-19 | Virochem Pharma Inc | composto, uso do mesmo na preparação de um medicamento para o tratamento ou prevenção de uma infecção por vìrus de hepatite c, composição farmacêutica e combinação farmacêutica |
| NZ563687A (en) | 2005-06-30 | 2011-07-29 | Smithkline Beecham Corp | 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[2-(1-methylethyl)-2,3-dihydro-1H-isoindol-5-yl]-1H-indole-7-carboxamide for inhibiting IKK2 (aka IKKbeta) |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
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-
2001
- 2001-07-25 SE SE0102617A patent/SE0102617D0/xx unknown
-
2002
- 2002-07-19 EP EP02756047A patent/EP1421079B1/en not_active Expired - Lifetime
- 2002-07-19 ES ES02756047T patent/ES2280559T3/es not_active Expired - Lifetime
- 2002-07-19 CN CNA028152514A patent/CN1538968A/zh active Pending
- 2002-07-19 MX MXPA04000755A patent/MXPA04000755A/es unknown
- 2002-07-19 IL IL16002302A patent/IL160023A0/xx unknown
- 2002-07-19 WO PCT/SE2002/001402 patent/WO2003010163A1/en not_active Ceased
- 2002-07-19 CA CA002454702A patent/CA2454702A1/en not_active Abandoned
- 2002-07-19 US US10/484,645 patent/US7098240B2/en not_active Expired - Fee Related
- 2002-07-19 KR KR10-2004-7001155A patent/KR20040018521A/ko not_active Withdrawn
- 2002-07-19 AT AT02756047T patent/ATE353327T1/de not_active IP Right Cessation
- 2002-07-19 JP JP2003515522A patent/JP2004536869A/ja not_active Withdrawn
- 2002-07-19 BR BR0211472-0A patent/BR0211472A/pt not_active IP Right Cessation
- 2002-07-19 DE DE60218048T patent/DE60218048T2/de not_active Expired - Lifetime
- 2002-07-19 NZ NZ530751A patent/NZ530751A/en unknown
-
2004
- 2004-01-22 ZA ZA200400494A patent/ZA200400494B/en unknown
- 2004-01-23 NO NO20040314A patent/NO20040314L/no unknown
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2009
- 2009-12-22 JP JP2009291103A patent/JP2010111683A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008087933A1 (ja) * | 2007-01-15 | 2008-07-24 | Santen Pharmaceutical Co., Ltd. | ＩκＢキナーゼβ阻害活性を有する新規インドール誘導体 |
| RU2470918C2 (ru) * | 2007-01-15 | 2012-12-27 | Сантен Фармасьютикал Ко., Лтд. | НОВЫЕ ПРОИЗВОДНЫЕ ИНДОЛА, ОБЛАДАЮЩИЕ ИНГИБИРУЮЩЕЙ АКТИВНОСТЬЮ В ОТНОШЕНИИ IκB КИНАЗЫ β |
| WO2010024227A1 (ja) * | 2008-08-25 | 2010-03-04 | 参天製薬株式会社 | ウレイド基、アミノカルボニル基及び置換基を有してもよい二環式基を置換基として有する新規ピロール誘導体 |
| JP2010077120A (ja) * | 2008-08-25 | 2010-04-08 | Santen Pharmaceut Co Ltd | ウレイド基、アミノカルボニル基及び置換基を有してもよい二環式基を置換基として有する新規ピロール誘導体 |
| US8088817B2 (en) | 2008-08-25 | 2012-01-03 | Santen Pharmaceutical Co., Ltd. | Pyrrole derivative having, as substituents, ureido group, aminocarbonly group and bicyclic group which may have substituent |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1538968A (zh) | 2004-10-20 |
| BR0211472A (pt) | 2004-11-09 |
| MXPA04000755A (es) | 2004-04-20 |
| US20040235821A1 (en) | 2004-11-25 |
| EP1421079A1 (en) | 2004-05-26 |
| DE60218048D1 (de) | 2007-03-22 |
| WO2003010163A1 (en) | 2003-02-06 |
| NO20040314L (no) | 2004-03-25 |
| NZ530751A (en) | 2005-09-30 |
| ATE353327T1 (de) | 2007-02-15 |
| CA2454702A1 (en) | 2003-02-06 |
| SE0102617D0 (sv) | 2001-07-25 |
| US7098240B2 (en) | 2006-08-29 |
| DE60218048T2 (de) | 2007-08-09 |
| KR20040018521A (ko) | 2004-03-03 |
| EP1421079B1 (en) | 2007-02-07 |
| ZA200400494B (en) | 2005-04-22 |
| JP2010111683A (ja) | 2010-05-20 |
| ES2280559T3 (es) | 2007-09-16 |
| IL160023A0 (en) | 2004-06-20 |
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