CA2464924A1 - Derives de carboxamide heteroaromatique destines au traitement des inflammations - Google Patents
Derives de carboxamide heteroaromatique destines au traitement des inflammations Download PDFInfo
- Publication number
- CA2464924A1 CA2464924A1 CA002464924A CA2464924A CA2464924A1 CA 2464924 A1 CA2464924 A1 CA 2464924A1 CA 002464924 A CA002464924 A CA 002464924A CA 2464924 A CA2464924 A CA 2464924A CA 2464924 A1 CA2464924 A1 CA 2464924A1
- Authority
- CA
- Canada
- Prior art keywords
- carboxamide
- amino
- group
- substituted
- thiophene
- 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.)
- Abandoned
Links
- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 29
- 206010061218 Inflammation Diseases 0.000 title claims abstract description 24
- 230000004054 inflammatory process Effects 0.000 title claims abstract description 24
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 208000035475 disorder Diseases 0.000 claims abstract description 16
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 206010003246 arthritis Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 100
- -1 PLK Proteins 0.000 claims description 68
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 125000001589 carboacyl group Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 101710205525 Inhibitor of nuclear factor kappa-B kinase subunit beta Proteins 0.000 claims description 24
- 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 229910052717 sulfur Chemical group 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 239000011593 sulfur Chemical group 0.000 claims description 23
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000000833 heterodimer Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 102000001253 Protein Kinase Human genes 0.000 claims description 9
- 108060006633 protein kinase Proteins 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- RUTDXYSTVWGVHB-UHFFFAOYSA-N 3-amino-5-(3-cyanophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C(C=CC=2)C#N)=C1 RUTDXYSTVWGVHB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- CQEZDVFMPVPYJQ-UHFFFAOYSA-N 3-amino-5-(3-aminophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C(N)C=CC=2)=C1 CQEZDVFMPVPYJQ-UHFFFAOYSA-N 0.000 claims description 4
- IVOJVTMDPKUPTH-UHFFFAOYSA-N 3-amino-5-(3-methoxyphenyl)thiophene-2-carboxamide Chemical compound COC1=CC=CC(C=2SC(=C(N)C=2)C(N)=O)=C1 IVOJVTMDPKUPTH-UHFFFAOYSA-N 0.000 claims description 4
- ZDOILDSDMJKJFZ-UHFFFAOYSA-N 3-amino-5-(4-cyanophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=CC(=CC=2)C#N)=C1 ZDOILDSDMJKJFZ-UHFFFAOYSA-N 0.000 claims description 4
- DYRYDYQWWQHRQE-UHFFFAOYSA-N 3-amino-5-phenylthiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=CC=CC=2)=C1 DYRYDYQWWQHRQE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- HXTWUSZCASUQIG-UHFFFAOYSA-N 3-amino-5-(3-carbamoylphenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C(C=CC=2)C(N)=O)=C1 HXTWUSZCASUQIG-UHFFFAOYSA-N 0.000 claims description 3
- HGINPGRITAMSJL-UHFFFAOYSA-N 3-amino-5-(3-nitrophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 HGINPGRITAMSJL-UHFFFAOYSA-N 0.000 claims description 3
- 101100452374 Mus musculus Ikbke gene Proteins 0.000 claims description 3
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- 108010029485 Protein Isoforms Proteins 0.000 claims description 3
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 3
- LTNWICBPQWPXDK-UHFFFAOYSA-N 3-amino-1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2C(N)=C(C(=O)N)SC2=C1 LTNWICBPQWPXDK-UHFFFAOYSA-N 0.000 claims description 2
- PCDMFUUYCAJDEP-UHFFFAOYSA-N 3-amino-4,5-diphenylthiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PCDMFUUYCAJDEP-UHFFFAOYSA-N 0.000 claims description 2
- XNCUFMKRKYGRGV-UHFFFAOYSA-N 3-amino-5-(2,5-dichlorothiophen-3-yl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C2=C(SC(Cl)=C2)Cl)=C1 XNCUFMKRKYGRGV-UHFFFAOYSA-N 0.000 claims description 2
- ZJODILPYNTYQDB-UHFFFAOYSA-N 3-amino-5-(2-aminophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C(=CC=CC=2)N)=C1 ZJODILPYNTYQDB-UHFFFAOYSA-N 0.000 claims description 2
- ISQCRQWKOUIVGG-UHFFFAOYSA-N 3-amino-5-(2-chlorophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C(=CC=CC=2)Cl)=C1 ISQCRQWKOUIVGG-UHFFFAOYSA-N 0.000 claims description 2
- JCCDXXOUFXIPGF-UHFFFAOYSA-N 3-amino-5-(2-nitrophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C(=CC=CC=2)[N+]([O-])=O)=C1 JCCDXXOUFXIPGF-UHFFFAOYSA-N 0.000 claims description 2
- WBNGLSWGNPTFCO-UHFFFAOYSA-N 3-amino-5-(3,4-dichlorophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C(Cl)C(Cl)=CC=2)=C1 WBNGLSWGNPTFCO-UHFFFAOYSA-N 0.000 claims description 2
- SMBURSXEZHQTIW-UHFFFAOYSA-N 3-amino-5-(3-methylphenyl)thiophene-2-carboxamide Chemical compound CC1=CC=CC(C=2SC(=C(N)C=2)C(N)=O)=C1 SMBURSXEZHQTIW-UHFFFAOYSA-N 0.000 claims description 2
- UDXIAXNCTMVCLS-UHFFFAOYSA-N 3-amino-5-(3-methylthiophen-2-yl)thiophene-2-carboxamide Chemical compound C1=CSC(C=2SC(=C(N)C=2)C(N)=O)=C1C UDXIAXNCTMVCLS-UHFFFAOYSA-N 0.000 claims description 2
- OIZDSSPXGPFWET-UHFFFAOYSA-N 3-amino-5-(4-aminophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=CC(N)=CC=2)=C1 OIZDSSPXGPFWET-UHFFFAOYSA-N 0.000 claims description 2
- QTYIQJPVOSRICH-UHFFFAOYSA-N 3-amino-5-(4-methylphenyl)thiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC(N)=C(C(N)=O)S1 QTYIQJPVOSRICH-UHFFFAOYSA-N 0.000 claims description 2
- UQXYJCHQINKMJB-UHFFFAOYSA-N 3-amino-5-(4-nitrophenyl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1 UQXYJCHQINKMJB-UHFFFAOYSA-N 0.000 claims description 2
- DLEYAZXTIKDOAA-UHFFFAOYSA-N 3-amino-5-(5-chlorothiophen-2-yl)thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2SC(Cl)=CC=2)=C1 DLEYAZXTIKDOAA-UHFFFAOYSA-N 0.000 claims description 2
- CZYMQLUMUPPLLB-UHFFFAOYSA-N 3-amino-5-(5-methylthiophen-2-yl)thiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C1=CC(N)=C(C(N)=O)S1 CZYMQLUMUPPLLB-UHFFFAOYSA-N 0.000 claims description 2
- DLHZOUDQWIWITC-UHFFFAOYSA-N 3-amino-5-[3-(aminomethyl)phenyl]thiophene-2-carboxamide Chemical compound NCC1=CC=CC(C=2SC(=C(N)C=2)C(N)=O)=C1 DLHZOUDQWIWITC-UHFFFAOYSA-N 0.000 claims description 2
- DCSFPZXAYKOLEI-UHFFFAOYSA-N 3-amino-5-[3-(ethylsulfonylamino)phenyl]thiophene-2-carboxamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2SC(=C(N)C=2)C(N)=O)=C1 DCSFPZXAYKOLEI-UHFFFAOYSA-N 0.000 claims description 2
- FADSTDBQMZWCSE-UHFFFAOYSA-N 3-amino-5-[3-(trifluoromethyl)phenyl]thiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C(C=CC=2)C(F)(F)F)=C1 FADSTDBQMZWCSE-UHFFFAOYSA-N 0.000 claims description 2
- LDONBNWKSIVCOI-UHFFFAOYSA-N 3-amino-5-phenanthren-2-ylthiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=C3C(C4=CC=CC=C4C=C3)=CC=2)=C1 LDONBNWKSIVCOI-UHFFFAOYSA-N 0.000 claims description 2
- UKVJQPBPRGHXRD-UHFFFAOYSA-N 3-amino-5-pyridin-3-ylthiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=NC=CC=2)=C1 UKVJQPBPRGHXRD-UHFFFAOYSA-N 0.000 claims description 2
- ZVSCZFDPBANIAB-UHFFFAOYSA-N 3-amino-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound NC1=C(C(=O)N)SC(C=2C=CN=CC=2)=C1 ZVSCZFDPBANIAB-UHFFFAOYSA-N 0.000 claims description 2
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- 101100220616 Caenorhabditis elegans chk-2 gene Proteins 0.000 claims description 2
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- 108091054455 MAP kinase family Proteins 0.000 claims description 2
- 102000043136 MAP kinase family Human genes 0.000 claims description 2
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- 150000002431 hydrogen Chemical class 0.000 claims 4
- ILDLKMTVSGBVAR-UHFFFAOYSA-N 3-amino-5-(2,5-dimethylthiophen-3-yl)thiophene-2-carboxamide Chemical compound S1C(C)=CC(C=2SC(=C(N)C=2)C(N)=O)=C1C ILDLKMTVSGBVAR-UHFFFAOYSA-N 0.000 claims 1
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- BMUACLADCKCNKZ-UHFFFAOYSA-N 3-amino-5-(3-thiophenyl)-2-thiophenecarboxamide Chemical compound NC1=C(C(=O)N)SC(C2=CSC=C2)=C1 BMUACLADCKCNKZ-UHFFFAOYSA-N 0.000 claims 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 125000005864 sulfonamidyl group Chemical group 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
La présente invention concerne des dérivés de carboxamide héréroaromatique, des compositions comprenant ces dérivés, des intermédiaires, des techniques de fabrication de ces dérivés de carboxamide héréroaromatique et des techniques de traitement du cancer, des inflammations et des pathologies associées aux inflammations, telles que l'arthrite.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34081601P | 2001-10-30 | 2001-10-30 | |
| US60/340,816 | 2001-10-30 | ||
| PCT/US2002/034801 WO2003037886A2 (fr) | 2001-10-30 | 2002-10-30 | Derives de carboxamide heteroaromatique destines au traitement des inflammations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2464924A1 true CA2464924A1 (fr) | 2003-05-08 |
Family
ID=23335051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002464924A Abandoned CA2464924A1 (fr) | 2001-10-30 | 2002-10-30 | Derives de carboxamide heteroaromatique destines au traitement des inflammations |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1444010A2 (fr) |
| JP (1) | JP2005509645A (fr) |
| AU (1) | AU2002356871A1 (fr) |
| BR (1) | BR0213734A (fr) |
| CA (1) | CA2464924A1 (fr) |
| MX (1) | MXPA04004064A (fr) |
| WO (1) | WO2003037886A2 (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6974870B2 (en) | 2002-06-06 | 2005-12-13 | Boehringer Ingelheim Phamaceuticals, Inc. | Substituted 3-amino-thieno [2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses |
| DK1513516T3 (da) | 2002-06-06 | 2009-10-19 | Boehringer Ingelheim Pharma | Substitueret 3-amino-thieno(2,3-b)-pyridin-2-carboxylsyreamid-forbindelser og fremgangsmåder til fremstilling og deres anvendelser |
| JP2006512313A (ja) | 2002-10-31 | 2006-04-13 | アムジェン インコーポレイテッド | 抗炎症剤 |
| WO2005012283A1 (fr) * | 2003-07-31 | 2005-02-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Composes de benzothiophene substitues et utilisations |
| FR2860792B1 (fr) * | 2003-10-10 | 2006-02-24 | Sanofi Synthelabo | Derives de thiophene-2-carboxamide, leur preparation et leur application en therapeutique |
| US7119102B2 (en) * | 2003-12-05 | 2006-10-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses |
| GB0400895D0 (en) * | 2004-01-15 | 2004-02-18 | Smithkline Beecham Corp | Chemical compounds |
| MXPA06010520A (es) | 2004-03-30 | 2007-03-26 | Chiron Corp | Derivados de tiofeno sustituidos como agentes anticancerosos. |
| 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 |
| HRP20100678T1 (hr) | 2005-03-29 | 2011-02-28 | Icos Corporation | Derivati heteroariluree korisni kao inhibitori chk1 |
| GB0507200D0 (en) * | 2005-04-08 | 2005-05-18 | Smithkline Beecham Corp | Chemical compounds |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| 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) |
| AU2007208358A1 (en) | 2006-01-23 | 2007-08-02 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| EP2418210A1 (fr) * | 2006-04-13 | 2012-02-15 | Vertex Pharmceuticals Incorporated | Thiophène-carboxamides servant d´inhibiteurs de protéines kinases |
| TWI498332B (zh) | 2006-04-26 | 2015-09-01 | Hoffmann La Roche | 作為pi3k抑制劑之嘧啶衍生物及相關製備方法、醫藥組合物、用途、套組及產物 |
| JP2009538309A (ja) * | 2006-05-23 | 2009-11-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチオフェンカルボキサミド |
| AU2007268056A1 (en) | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
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| GB1360982A (en) * | 1970-08-27 | 1974-07-24 | Beecham Group Ltd | Derivatives of 1-phenyl-5-aminoimidazole and compositions thereof |
| US3864359A (en) * | 1972-05-01 | 1975-02-04 | American Cyanamid Co | 5-amino-3-ethyl-1-phenyl-4-pyrazolecarboxamides and method of preparation thereof |
| US4264495A (en) * | 1972-05-15 | 1981-04-28 | Eastman Kodak Company | 2-Thienyl azo dyestuff compounds |
| GB1468012A (en) * | 1973-08-09 | 1977-03-23 | Beecham Group Ltd | 2-amino-3-carboxy-thiophene derivatives |
| DD236530A1 (de) * | 1985-04-26 | 1986-06-11 | Univ Halle Wittenberg | Verfahren zur herstellung von 2-cyano-2-(4h-4-oxo-1,2,dihydro-thieno 2,3-d 1,3 thiazin-2-yliden)-essigsaeureestern |
| DD263055A1 (de) * | 1987-07-28 | 1988-12-21 | Univ Dresden Tech | Verfahren zur herstellung substituierter 3-amino-5-phenyl-thiophene |
| DE3914430A1 (de) * | 1988-05-05 | 1989-11-16 | Ciba Geigy Ag | Azofarbstoffe, verfahren zu deren herstellung und deren verwendung |
| DE4019168A1 (de) * | 1989-06-19 | 1990-12-20 | Ciba Geigy Ag | Azofarbstoffe, deren herstellung und verwendung |
| GB0003154D0 (en) * | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| JP2002105081A (ja) * | 2000-07-28 | 2002-04-10 | Nikken Chem Co Ltd | 新規チオフェンニ環化合物 |
| EP1324759A4 (fr) * | 2000-10-12 | 2004-05-12 | Smithkline Beecham Corp | Inhibiteurs du nf-g(k)b |
| SE0102616D0 (sv) * | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| WO2003028731A1 (fr) * | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Inhibiteurs de kinase chk1 |
-
2002
- 2002-10-30 AU AU2002356871A patent/AU2002356871A1/en not_active Abandoned
- 2002-10-30 BR BR0213734-8A patent/BR0213734A/pt not_active IP Right Cessation
- 2002-10-30 WO PCT/US2002/034801 patent/WO2003037886A2/fr not_active Ceased
- 2002-10-30 MX MXPA04004064A patent/MXPA04004064A/es unknown
- 2002-10-30 JP JP2003540167A patent/JP2005509645A/ja not_active Withdrawn
- 2002-10-30 EP EP02802495A patent/EP1444010A2/fr not_active Withdrawn
- 2002-10-30 CA CA002464924A patent/CA2464924A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003037886A2 (fr) | 2003-05-08 |
| EP1444010A2 (fr) | 2004-08-11 |
| JP2005509645A (ja) | 2005-04-14 |
| MXPA04004064A (es) | 2004-09-06 |
| WO2003037886A3 (fr) | 2003-12-24 |
| BR0213734A (pt) | 2004-10-19 |
| AU2002356871A1 (en) | 2003-05-12 |
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