CA2604463C - 3-amino-pyrazolo[3,4b]pyridines as inhibitors of protein tyrosine kinases, their production and use as pharmaceutical agents - Google Patents
3-amino-pyrazolo[3,4b]pyridines as inhibitors of protein tyrosine kinases, their production and use as pharmaceutical agents Download PDFInfo
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- CA2604463C CA2604463C CA2604463A CA2604463A CA2604463C CA 2604463 C CA2604463 C CA 2604463C CA 2604463 A CA2604463 A CA 2604463A CA 2604463 A CA2604463 A CA 2604463A CA 2604463 C CA2604463 C CA 2604463C
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- stands
- alkyl
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- substituted
- ring
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 221
- 239000008177 pharmaceutical agent Substances 0.000 title claims description 19
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 title abstract description 12
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 title abstract description 12
- 239000003112 inhibitor Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 222
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 201000010099 disease Diseases 0.000 claims abstract description 25
- -1 C3-C10-cycloalkyl Chemical group 0.000 claims description 148
- 125000001072 heteroaryl group Chemical group 0.000 claims description 127
- 125000003118 aryl group Chemical group 0.000 claims description 117
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
- 229910052736 halogen Inorganic materials 0.000 claims description 99
- 150000002367 halogens Chemical class 0.000 claims description 99
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 91
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 84
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 84
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- 239000012453 solvate Substances 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
- 239000011593 sulfur Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001041 indolyl group Chemical group 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000003944 tolyl group Chemical group 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 230000001154 acute effect Effects 0.000 claims description 9
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- 230000004770 neurodegeneration Effects 0.000 claims description 9
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 230000035168 lymphangiogenesis Effects 0.000 claims description 8
- 230000004862 vasculogenesis Effects 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 208000019553 vascular disease Diseases 0.000 claims description 7
- 125000004799 bromophenyl group Chemical group 0.000 claims description 6
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000000376 autoradiography Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 238000001727 in vivo Methods 0.000 claims description 3
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 108
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- 101150041968 CDC13 gene Proteins 0.000 description 83
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 83
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 80
- 239000000126 substance Substances 0.000 description 71
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 45
- 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 38
- 238000005481 NMR spectroscopy Methods 0.000 description 38
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 38
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
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- 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 24
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004061288A DE102004061288A1 (de) | 2004-12-14 | 2004-12-14 | 3-Amino-Pyrazolo[3,4b]pyridine als Inhibitoren von Proteintyrosinkinasen, deren Herstellung und Verwendung als Arzneimittel |
| DE102004061288.9 | 2004-12-14 | ||
| US63669004P | 2004-12-17 | 2004-12-17 | |
| US60/636,690 | 2004-12-17 | ||
| PCT/EP2005/013417 WO2006063805A1 (de) | 2004-12-14 | 2005-12-12 | 3-amino-pyrazolo[3,4b]pyridine als inhibitoren von proteintyrosinkinasen zur behandlung von angiogen, hyperproliferativen oder neurodegenerativen erkrankungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2604463A1 CA2604463A1 (en) | 2006-06-22 |
| CA2604463C true CA2604463C (en) | 2014-03-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2604463A Expired - Fee Related CA2604463C (en) | 2004-12-14 | 2005-12-12 | 3-amino-pyrazolo[3,4b]pyridines as inhibitors of protein tyrosine kinases, their production and use as pharmaceutical agents |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7977325B2 (https=) |
| EP (1) | EP1846402B1 (https=) |
| JP (1) | JP2008523018A (https=) |
| AR (1) | AR051794A1 (https=) |
| CA (1) | CA2604463C (https=) |
| DE (1) | DE102004061288A1 (https=) |
| DO (1) | DOP2005000251A (https=) |
| GT (1) | GT200500363A (https=) |
| PA (1) | PA8656401A1 (https=) |
| PE (1) | PE20060737A1 (https=) |
| TW (1) | TW200634012A (https=) |
| UY (1) | UY29253A1 (https=) |
| WO (1) | WO2006063805A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| EP1980561B1 (en) * | 2007-03-30 | 2013-10-09 | Nerviano Medical Sciences S.R.L. | Substituted 1h-pyrazolo[3,4-b] pyridine derivatives active as kinase inhibitors |
| US8252937B2 (en) | 2007-09-14 | 2012-08-28 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones |
| PL2203439T3 (pl) | 2007-09-14 | 2011-06-30 | Addex Pharmaceuticals Sa | 1',3'-dipodstawione-4-fenylo-3,4,5,6-tetrahydro-2H, 1'H-[1, 4']bipirydynylo-2'-ketony |
| US8722894B2 (en) | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| CA2704266A1 (en) * | 2007-11-02 | 2009-06-11 | Vertex Pharmaceuticals Incorporated | [1h- pyrazolo [3, 4-b] pyridine-4-yl] -phenyle or -pyridin-2-yle derivatives as protein kinase c-theta |
| RU2492170C9 (ru) | 2007-11-14 | 2013-12-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2 |
| JP5547194B2 (ja) | 2008-09-02 | 2014-07-09 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体の調節因子としての３−アザビシクロ［３．１．０］ヘキシル誘導体 |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
| WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MY153912A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 1, 2, 4,-triazolo[4,3-a[pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| CN102439008B (zh) | 2009-05-12 | 2015-04-29 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| EP2464647B1 (en) | 2009-08-11 | 2016-09-21 | Bristol-Myers Squibb Company | Azaindazoles as btk kinase modulators and use thereof |
| EP2516437B1 (en) | 2009-12-21 | 2014-01-29 | Novartis AG | Disubstituted heteroaryl-fused pyridines |
| CN103140490A (zh) | 2010-07-15 | 2013-06-05 | 百时美施贵宝公司 | 氮杂吲唑化合物 |
| CN103261195B (zh) | 2010-11-08 | 2015-09-02 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| EP2661435B1 (en) | 2010-11-08 | 2015-08-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| PL2649069T3 (pl) | 2010-11-08 | 2016-01-29 | Janssen Pharmaceuticals Inc | Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2 |
| FR2970967B1 (fr) | 2011-01-27 | 2013-02-15 | Pf Medicament | Derives de type azaindazole ou diazaindazole comme medicament |
| US10138235B2 (en) | 2011-12-14 | 2018-11-27 | Sanofi | Pyrazolopyridine derivatives, preparation process therefor and therapeutic use thereof |
| FR2984325A1 (fr) * | 2011-12-14 | 2013-06-21 | Sanofi Sa | Derives de pyrazolopyridine, leur procede de preparation et leur application en therapeutique |
| EP2689778A1 (en) * | 2012-07-27 | 2014-01-29 | Pierre Fabre Medicament | Derivatives of azaindoles or diazaindoles for treating pain |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| KR20220049612A (ko) | 2014-01-21 | 2022-04-21 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| HUE053734T2 (hu) | 2014-01-21 | 2021-07-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait tartalmazó kombinációk és alkalmazásuk |
| WO2024211708A1 (en) * | 2023-04-06 | 2024-10-10 | Myrobalan Therapeutics, Inc. | Tyk2 inhibitors for treatment of glaucoma |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2160780A1 (de) | 1971-12-08 | 1973-06-14 | Basf Ag | Pyridino-pyrazole |
| DE2238400A1 (de) * | 1972-08-04 | 1974-02-14 | Hoechst Ag | Basische azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| DE2355967A1 (de) | 1973-11-09 | 1975-07-24 | Hoechst Ag | Polycyclische farbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| DE2643753A1 (de) * | 1976-09-29 | 1978-04-06 | Thomae Gmbh Dr K | Neue 1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine |
| DE3001498A1 (de) * | 1980-01-17 | 1981-07-23 | Agfa-Gevaert Ag, 5090 Leverkusen | Fotografisches material mit einem stabilisierungsmittel, verfahren zu dessen herstellung, ein entwicklungsverfahren, neue pyrazole, ein verfahren zu deren herstellung sowie zwischenprodukte |
| US5478830A (en) * | 1992-05-29 | 1995-12-26 | The Du Pont Merck Pharmaceutical Company | Fused-ring heterocycles for the treatment of atherosclerosis |
| US6046216A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyridinone derivatives |
| PL354241A1 (en) * | 1999-09-17 | 2003-12-29 | Abbott Gmbh & Co.Kgabbott Gmbh & Co.Kg | Kinase inhibitors as therapeutic agents |
| JP4251868B2 (ja) * | 2000-08-11 | 2009-04-08 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ２−アミノピリジン化合物および医薬用途 |
| JP4272338B2 (ja) * | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
| FR2827603B1 (fr) | 2001-07-18 | 2003-10-17 | Oreal | Composes derives de diaminopyrazole substitues par un radical heteroaromatique et leur utilisation en teinture d'oxydation des fibres keratiniques |
| DE50207026D1 (de) * | 2001-08-23 | 2006-07-06 | Bayer Cropscience Sa | Substituierte propargylamine |
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2004
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2005
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- 2005-12-12 GT GT200500363A patent/GT200500363A/es unknown
- 2005-12-12 JP JP2007544844A patent/JP2008523018A/ja active Pending
- 2005-12-12 CA CA2604463A patent/CA2604463C/en not_active Expired - Fee Related
- 2005-12-12 WO PCT/EP2005/013417 patent/WO2006063805A1/de not_active Ceased
- 2005-12-12 EP EP05821901.5A patent/EP1846402B1/de not_active Expired - Lifetime
- 2005-12-13 PE PE2005001439A patent/PE20060737A1/es not_active Application Discontinuation
- 2005-12-14 TW TW094144374A patent/TW200634012A/zh unknown
- 2005-12-14 US US11/302,307 patent/US7977325B2/en not_active Expired - Fee Related
- 2005-12-14 PA PA20058656401A patent/PA8656401A1/es unknown
- 2005-12-14 AR ARP050105227A patent/AR051794A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2604463A1 (en) | 2006-06-22 |
| JP2008523018A (ja) | 2008-07-03 |
| DOP2005000251A (es) | 2006-06-30 |
| EP1846402B1 (de) | 2014-02-26 |
| GT200500363A (es) | 2006-11-27 |
| PE20060737A1 (es) | 2006-08-17 |
| US20090030010A1 (en) | 2009-01-29 |
| PA8656401A1 (es) | 2006-07-03 |
| EP1846402A1 (de) | 2007-10-24 |
| DE102004061288A1 (de) | 2006-06-29 |
| AR051794A1 (es) | 2007-02-07 |
| UY29253A1 (es) | 2006-06-30 |
| WO2006063805A1 (de) | 2006-06-22 |
| TW200634012A (en) | 2006-10-01 |
| US7977325B2 (en) | 2011-07-12 |
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