JP2003512467A5 - - Google Patents
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- JP2003512467A5 JP2003512467A5 JP2001533132A JP2001533132A JP2003512467A5 JP 2003512467 A5 JP2003512467 A5 JP 2003512467A5 JP 2001533132 A JP2001533132 A JP 2001533132A JP 2001533132 A JP2001533132 A JP 2001533132A JP 2003512467 A5 JP2003512467 A5 JP 2003512467A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally
- substituted
- optionally substituted
- fluorophenyl
- 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.)
- Pending
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- -1 CF 3 Chemical group 0.000 description 27
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 125000005842 heteroatom Chemical group 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000006413 ring segment Chemical group 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 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 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 4
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000001363 autoimmune Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 description 3
- 239000003018 immunosuppressive agent Substances 0.000 description 3
- 208000027866 inflammatory disease Diseases 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical class 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 229960003444 immunosuppressant agent Drugs 0.000 description 2
- 230000001861 immunosuppressant effect Effects 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QWLKXLNJJRBNII-UHFFFAOYSA-N 1-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[4,5-b]pyridin-5-amine Chemical compound N=1C2=NC(N)=CC=C2N(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 QWLKXLNJJRBNII-UHFFFAOYSA-N 0.000 description 1
- HQYTZGXGJITFDL-UHFFFAOYSA-N 1-[2-(cyclopentylamino)pyrimidin-4-yl]-n-(3-fluorophenyl)-2-(4-fluorophenyl)imidazo[4,5-b]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(NC=3C=C(F)C=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 HQYTZGXGJITFDL-UHFFFAOYSA-N 0.000 description 1
- ICHINRNOSJBRCE-HNNXBMFYSA-N 2-(4-fluorophenyl)-1-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]imidazo[4,5-b]pyridin-5-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N(C1=CC=C(N)N=C1N=1)C=1C1=CC=C(F)C=C1 ICHINRNOSJBRCE-HNNXBMFYSA-N 0.000 description 1
- XUQRICHQPSQKSS-FQEVSTJZSA-N 4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N(C1=CC=2)C(C=3C=CC(F)=CC=3)=NC1=NC=2N1CCN(C)CC1 XUQRICHQPSQKSS-FQEVSTJZSA-N 0.000 description 1
- MJMDLUIORMBKHA-IBGZPJMESA-N 4-[4-(4-fluorophenyl)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1SC(N2CCC(C)CC2)=NC=1C1=CC=C(F)C=C1 MJMDLUIORMBKHA-IBGZPJMESA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- SQEPRLVLDFJTMM-UHFFFAOYSA-N Cc1nc(nc(C=C)cc2)c2[nH]1 Chemical compound Cc1nc(nc(C=C)cc2)c2[nH]1 SQEPRLVLDFJTMM-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- OONDROKXCHJESN-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-[4-(4-fluorophenyl)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound C1CC(C)CCN1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=C(NCC3CC3)N=CC=2)S1 OONDROKXCHJESN-UHFFFAOYSA-N 0.000 description 1
- MGIUUUFXHGZVRO-UHFFFAOYSA-N n-benzyl-1-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[4,5-b]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(NCC=3C=CC=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 MGIUUUFXHGZVRO-UHFFFAOYSA-N 0.000 description 1
- UBTOWEAWXVZTQD-UHFFFAOYSA-N n-cyclobutyl-4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CCC4)N=CC=3)C2=N1 UBTOWEAWXVZTQD-UHFFFAOYSA-N 0.000 description 1
- DESTZNVBBLDULL-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-(1-methylpiperidin-4-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CCCC4)N=CC=3)C2=N1 DESTZNVBBLDULL-UHFFFAOYSA-N 0.000 description 1
- BARFMAOTOPEJFY-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CCCC4)N=CC=3)C2=N1 BARFMAOTOPEJFY-UHFFFAOYSA-N 0.000 description 1
- YGDCPBYTBSIICB-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-morpholin-4-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(N3CCOCC3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 YGDCPBYTBSIICB-UHFFFAOYSA-N 0.000 description 1
- TYHALPCMJPGQFF-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-piperidin-4-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(C3CCNCC3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 TYHALPCMJPGQFF-UHFFFAOYSA-N 0.000 description 1
- CMDWMHFRSWQQAO-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-pyridin-3-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(C=3C=NC=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 CMDWMHFRSWQQAO-UHFFFAOYSA-N 0.000 description 1
- GFJQCVZKRHKDIX-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-pyridin-4-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(C=3C=CN=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 GFJQCVZKRHKDIX-UHFFFAOYSA-N 0.000 description 1
- WRFUMBPRGLYOAV-UHFFFAOYSA-N n-cyclopropyl-4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CC4)N=CC=3)C2=N1 WRFUMBPRGLYOAV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9925441.9A GB9925441D0 (en) | 1999-10-27 | 1999-10-27 | Organic compounds |
| GB9925441.9 | 1999-10-27 | ||
| GB9926173.7 | 1999-11-04 | ||
| GBGB9926173.7A GB9926173D0 (en) | 1999-11-04 | 1999-11-04 | Organic compounds |
| PCT/EP2000/010528 WO2001030778A1 (en) | 1999-10-27 | 2000-10-25 | Thiazole and imidazo [4,5-b] pyridine compounds and their pharmaceutical use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003512467A JP2003512467A (ja) | 2003-04-02 |
| JP2003512467A5 true JP2003512467A5 (enExample) | 2007-12-06 |
Family
ID=26316029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001533132A Pending JP2003512467A (ja) | 1999-10-27 | 2000-10-25 | チアゾールおよびイミダゾ（４，５−ｂ）ピリジン化合物ならびにそれらの医薬用途 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6608072B1 (enExample) |
| EP (1) | EP1224185B1 (enExample) |
| JP (1) | JP2003512467A (enExample) |
| AR (1) | AR029011A1 (enExample) |
| AT (1) | ATE311385T1 (enExample) |
| AU (1) | AU7922900A (enExample) |
| CO (1) | CO5251463A1 (enExample) |
| DE (1) | DE60024480T2 (enExample) |
| ES (1) | ES2254238T3 (enExample) |
| PE (1) | PE20011039A1 (enExample) |
| WO (1) | WO2001030778A1 (enExample) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6632820B1 (en) | 1998-08-29 | 2003-10-14 | Astrazeneca Ab | Pyrimidine compounds |
| ES2274634T3 (es) | 1998-08-29 | 2007-05-16 | Astrazeneca Ab | Compuestos de pirimidina. |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| GB0004886D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
| US6943174B2 (en) | 2000-06-14 | 2005-09-13 | Warner-Lambert Company | 6,5-Fused bicyclic heterocycles |
| GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| GB0021726D0 (en) | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| US7199124B2 (en) | 2001-02-02 | 2007-04-03 | Takeda Pharmaceutical Company Limited | JNK inhibitor |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
| HRP20040098B1 (en) | 2001-08-13 | 2012-08-31 | Janssen Pharmaceutica N.V. | 2,4,5-TRlSUBSTITUTED THIAZOLYL DERIVATIVES AND THEIR ANTIINFLAMMATORY ACTIVITY |
| BR0306785A (pt) | 2002-01-07 | 2004-11-09 | Eisai Co Ltd | Deazapurinas e seus usos |
| TWI322807B (en) * | 2002-01-07 | 2010-04-01 | Eisai R&D Man Co Ltd | Novel deazapurines and uses thereof |
| GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| AU2003208479A1 (en) | 2002-03-09 | 2003-09-22 | Astrazeneca Ab | 4- imidazolyl substuited pyrimidine derivatives with cdk inhibitiory activity |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| JP4570955B2 (ja) * | 2002-07-09 | 2010-10-27 | バーテクス ファーマスーティカルズ インコーポレイテッド | プロテインキナーゼ阻害活性を持つイミダゾール類 |
| CA2496445A1 (en) * | 2002-08-14 | 2004-02-26 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anticoagulant and fibrinolytic therapy using p38 map kinase inhibitors |
| GB0226583D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| DE602004029145D1 (de) | 2003-02-27 | 2010-10-28 | Palau Pharma Sa | Pyrazolopyridin-derivate |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| TWI334868B (en) * | 2003-06-03 | 2010-12-21 | Nippon Kayaku Kk | [1,2,4] triazoro [1,5-a] pyrimidine-2-ylurea derivative and use thereof |
| AU2004261482A1 (en) * | 2003-07-30 | 2005-02-10 | Cyclacel Limited | Pyridinylamino-pyrimidine derivatives as protein kinase inhibitors |
| US7632950B2 (en) * | 2003-08-18 | 2009-12-15 | Fujifilm Finechemicals Co., Ltd | Pyridyltetrahydropyridines and pyridylpiperidines and method of manufacturing them |
| GB0401336D0 (en) * | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| US7504403B2 (en) * | 2004-01-22 | 2009-03-17 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| TWI332003B (en) * | 2004-01-30 | 2010-10-21 | Lilly Co Eli | Kinase inhibitors |
| TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
| WO2006051826A1 (ja) | 2004-11-10 | 2006-05-18 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびその医薬用途 |
| KR100848205B1 (ko) * | 2005-06-20 | 2008-07-24 | 주식회사 동부하이텍 | 면역 억제 및 염증 억제 활성을 갖는 신규한 치환된1,3-티아졸 유도체 또는 이의 약학적으로 허용가능한 염,중간체 화합물 또는 이의 약학적으로 허용가능한 염, 이의제조방법, 및 이를 포함하는 약학적 조성물 |
| WO2007034278A2 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Fused imidazole derivatives as c3a receptor antagonists |
| CA2623374A1 (en) | 2005-09-30 | 2007-04-05 | Astrazeneca Ab | Imidazo [1,2-a] pyridine having anti-cell-proliferation activity |
| RU2008112691A (ru) | 2005-10-03 | 2009-10-10 | Оно Фармасьютикал Ко., Лтд. (Jp) | Азотсодержащее гетероциклическое соединение и его фармацевтическое применение |
| AP2707A (en) * | 2007-08-27 | 2013-07-29 | Siga Technologies Inc | Antiviral drugs for treatment of arenavirus infection |
| WO2009076140A1 (en) * | 2007-12-13 | 2009-06-18 | Smithkline Beecham Corporation | Thiazole and oxazole kinase inhibitors |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| WO2009140128A2 (en) * | 2008-05-13 | 2009-11-19 | Irm Llc | Compounds and compositions as kinase inhibitors |
| AU2009322346B2 (en) | 2008-12-03 | 2015-07-02 | The Scripps Research Institute | Stem cell cultures |
| EP2198710A1 (de) | 2008-12-19 | 2010-06-23 | Bayer CropScience AG | Verwendung von 5-Pyridin-4yl-(1,3)Thiazole zur Bekämpfung phytopathogener Pilze |
| EP2432767B1 (en) * | 2009-05-19 | 2013-06-26 | Dow AgroSciences LLC | Compounds and methods for controlling fungi |
| SG192941A1 (en) * | 2011-02-25 | 2013-09-30 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| CN103145706B (zh) * | 2012-11-16 | 2015-11-25 | 温州医学院 | 一类具有抗炎作用的咪唑并吡啶类化合物及其在制备抗炎药物中的应用 |
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-
2000
- 2000-10-25 WO PCT/EP2000/010528 patent/WO2001030778A1/en not_active Ceased
- 2000-10-25 EP EP00969551A patent/EP1224185B1/en not_active Expired - Lifetime
- 2000-10-25 JP JP2001533132A patent/JP2003512467A/ja active Pending
- 2000-10-25 ES ES00969551T patent/ES2254238T3/es not_active Expired - Lifetime
- 2000-10-25 AU AU79229/00A patent/AU7922900A/en not_active Abandoned
- 2000-10-25 DE DE60024480T patent/DE60024480T2/de not_active Expired - Lifetime
- 2000-10-25 US US10/111,233 patent/US6608072B1/en not_active Expired - Fee Related
- 2000-10-25 AT AT00969551T patent/ATE311385T1/de not_active IP Right Cessation
- 2000-10-26 AR ARP000105643A patent/AR029011A1/es unknown
- 2000-10-26 PE PE2000001147A patent/PE20011039A1/es not_active Application Discontinuation
- 2000-10-27 CO CO00082019A patent/CO5251463A1/es not_active Application Discontinuation
-
2003
- 2003-06-23 US US10/601,690 patent/US6891039B2/en not_active Expired - Fee Related
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