CA2698511C - Substituted pyrimidinyl-amines as protein kinase inhibitors - Google Patents
Substituted pyrimidinyl-amines as protein kinase inhibitors Download PDFInfo
- Publication number
- CA2698511C CA2698511C CA2698511A CA2698511A CA2698511C CA 2698511 C CA2698511 C CA 2698511C CA 2698511 A CA2698511 A CA 2698511A CA 2698511 A CA2698511 A CA 2698511A CA 2698511 C CA2698511 C CA 2698511C
- Authority
- CA
- Canada
- Prior art keywords
- triazol
- pyrimidin
- phenyl
- substituted
- amine
- 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.)
- Expired - Fee Related
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- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 158
- 150000003839 salts Chemical class 0.000 claims abstract description 84
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 53
- 230000005764 inhibitory process Effects 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 230000037361 pathway Effects 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 215
- 125000000623 heterocyclic group Chemical group 0.000 claims description 129
- 125000005842 heteroatom Chemical group 0.000 claims description 84
- 229910052731 fluorine Inorganic materials 0.000 claims description 75
- 229910052794 bromium Inorganic materials 0.000 claims description 72
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 65
- -1 CH2-C3-6 cycloalkyl Chemical group 0.000 claims description 56
- 229910052740 iodine Inorganic materials 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 54
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
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- IZXPPXICNCVEFE-UHFFFAOYSA-N trimethyl(2-morpholin-4-ylethynyl)silane Chemical compound C[Si](C)(C)C#CN1CCOCC1 IZXPPXICNCVEFE-UHFFFAOYSA-N 0.000 description 1
- HDWHGDDNMJOCCU-UHFFFAOYSA-N trimethyl(pyridin-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=N1 HDWHGDDNMJOCCU-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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| US96984907P | 2007-09-04 | 2007-09-04 | |
| US60/969,849 | 2007-09-04 | ||
| PCT/US2008/075151 WO2009032861A1 (en) | 2007-09-04 | 2008-09-03 | Substituted pyrimidinyl-amines as protein kinase inhibitors |
Publications (2)
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| CA2698511A1 CA2698511A1 (en) | 2009-03-12 |
| CA2698511C true CA2698511C (en) | 2016-10-11 |
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| CA2698511A Expired - Fee Related CA2698511C (en) | 2007-09-04 | 2008-09-03 | Substituted pyrimidinyl-amines as protein kinase inhibitors |
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| PT (1) | PT2200436E (enExample) |
| WO (1) | WO2009032861A1 (enExample) |
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| JP2010513384A (ja) | 2006-12-22 | 2010-04-30 | エフ.ホフマン−ラ ロシュ アーゲー | スピロ−ピペリジン誘導体 |
| HUE029188T2 (en) * | 2007-03-12 | 2017-03-28 | Ym Biosciences Australia Pty | Phenylamino-pyrimidine compounds and their use |
| AU2016200866B2 (en) * | 2007-03-12 | 2017-06-22 | Glaxosmithkline Llc | Phenyl amino pyrimidine compounds and uses thereof |
| AU2013201306B2 (en) * | 2007-03-12 | 2015-11-12 | Glaxosmithkline Llc | Phenyl Amino Pyrimidine Compounds and Uses Thereof |
| US8507511B2 (en) * | 2007-04-24 | 2013-08-13 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| WO2009032861A1 (en) | 2007-09-04 | 2009-03-12 | The Scripps Research Institute | Substituted pyrimidinyl-amines as protein kinase inhibitors |
| WO2009087127A1 (en) | 2008-01-11 | 2009-07-16 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| ES2428716T3 (es) * | 2008-02-22 | 2013-11-11 | F. Hoffmann-La Roche Ag | Moduladores de beta-amiloide |
| JP5502089B2 (ja) | 2008-10-09 | 2014-05-28 | エフ.ホフマン−ラ ロシュ アーゲー | アミロイドβのモジュレーター |
| WO2010052199A1 (en) | 2008-11-10 | 2010-05-14 | F. Hoffmann-La Roche Ag | Heterocyclic gamma secretase modulators |
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| EP2598660B1 (en) | 2010-07-26 | 2017-03-15 | Biomatrica, INC. | Compositions for stabilizing dna, rna and proteins in blood and other biological samples during shipping and storage at ambient temperatures |
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- 2008-09-03 US US12/676,411 patent/US8530480B2/en not_active Expired - Fee Related
- 2008-09-03 CA CA2698511A patent/CA2698511C/en not_active Expired - Fee Related
- 2008-09-03 ES ES08829943.3T patent/ES2535166T3/es active Active
- 2008-09-03 PT PT88299433T patent/PT2200436E/pt unknown
- 2008-09-03 JP JP2010524122A patent/JP5611826B2/ja not_active Expired - Fee Related
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2014
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| US9018205B2 (en) | 2015-04-28 |
| JP5611826B2 (ja) | 2014-10-22 |
| EP2200436A4 (en) | 2011-12-28 |
| WO2009032861A1 (en) | 2009-03-12 |
| US20150232429A1 (en) | 2015-08-20 |
| EP2200436A1 (en) | 2010-06-30 |
| US8530480B2 (en) | 2013-09-10 |
| PT2200436E (pt) | 2015-04-29 |
| CA2698511A1 (en) | 2009-03-12 |
| JP2010538076A (ja) | 2010-12-09 |
| JP2015007102A (ja) | 2015-01-15 |
| US20130231336A1 (en) | 2013-09-05 |
| ES2535166T3 (es) | 2015-05-06 |
| EP2200436B1 (en) | 2015-01-21 |
| JP5937648B2 (ja) | 2016-06-22 |
| US20100298312A1 (en) | 2010-11-25 |
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