CA2554551A1

CA2554551A1 - Compositions useful as inhibitors of protein kinases

Compositions useful as inhibitors of protein kinases Download PDF

Info

Publication number: CA2554551A1
Authority: CA; Canada
Prior art keywords: c6alkyl; compound; optionally substituted; independently; ring
Prior art date: 2004-01-26
Legal status : Abandoned

Application number

CA002554551A

Other languages

English (en)

French (fr)

Inventor

Juan-Miguel Jimenez

Sanjay Patel

David Kay

Ronald Knegtel

Oliver Philps

Current Assignee

Vertex Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2004-01-26

Filing date

2005-01-26

Publication date

2005-10-13

2005-01-26 Application filed by Individual filed Critical Individual

2005-10-13 Publication of CA2554551A1 publication Critical patent/CA2554551A1/en

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 77
239000003112 inhibitor Substances 0.000 title abstract description 19
102000001253 Protein Kinase Human genes 0.000 title abstract description 16
108060006633 protein kinase Proteins 0.000 title abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 187
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
201000010099 disease Diseases 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 33
238000011282 treatment Methods 0.000 claims abstract description 12
-1 phenyloxy, benzyl Chemical group 0.000 claims description 109
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 94
101100180319 Mus musculus Itk gene Proteins 0.000 claims description 77
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
229910052757 nitrogen Inorganic materials 0.000 claims description 45
125000001931 aliphatic group Chemical group 0.000 claims description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 40
229910052717 sulfur Chemical group 0.000 claims description 38
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical class 0.000 claims description 36
229910052760 oxygen Inorganic materials 0.000 claims description 36
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
239000001301 oxygen Chemical group 0.000 claims description 33
239000011593 sulfur Chemical group 0.000 claims description 33
125000005842 heteroatom Chemical group 0.000 claims description 32
125000003118 aryl group Chemical group 0.000 claims description 30
125000002950 monocyclic group Chemical group 0.000 claims description 28
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
125000004429 atom Chemical group 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 24
229920006395 saturated elastomer Polymers 0.000 claims description 22
108091000080 Phosphotransferase Proteins 0.000 claims description 21
102000020233 phosphotransferase Human genes 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 19
125000000623 heterocyclic group Chemical group 0.000 claims description 19
230000001404 mediated effect Effects 0.000 claims description 19
125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
229910052794 bromium Chemical group 0.000 claims description 15
230000000694 effects Effects 0.000 claims description 15
208000035475 disorder Diseases 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
206010039083 rhinitis Diseases 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000002541 furyl group Chemical group 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000003226 pyrazolyl group Chemical group 0.000 claims description 12
229930192474 thiophene Natural products 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
229940124597 therapeutic agent Drugs 0.000 claims description 11
208000030507 AIDS Diseases 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
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 9
125000001118 alkylidene group Chemical group 0.000 claims description 8
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239000002552 dosage form Substances 0.000 claims description 8
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125000002619 bicyclic group Chemical group 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
230000002062 proliferating effect Effects 0.000 claims description 7
125000006413 ring segment Chemical group 0.000 claims description 7
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BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 4
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NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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125000000335 thiazolyl group Chemical group 0.000 claims description 4
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
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238000002399 angioplasty Methods 0.000 claims description 2
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210000001185 bone marrow Anatomy 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
206010039088 Rhinitis atrophic Diseases 0.000 claims 1
239000011440 grout Substances 0.000 claims 1
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238000003556 assay Methods 0.000 description 41
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238000005160 1H NMR spectroscopy Methods 0.000 description 16
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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