CA2615946A1 - Pyrazolo pyrimidines useful as aurora kinase inhibitors - Google Patents

Info

Publication number

CA2615946A1

CA2615946A1 CA002615946A CA2615946A CA2615946A1 CA 2615946 A1 CA2615946 A1 CA 2615946A1 CA 002615946 A CA002615946 A CA 002615946A CA 2615946 A CA2615946 A CA 2615946A CA 2615946 A1 CA2615946 A1 CA 2615946A1

Authority

CA

Canada

Prior art keywords

alkyl

aryl

heteroaryl

hydrogen

heteroalkyl

Prior art date

2005-07-22

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000003719 aurora kinase inhibitor Substances 0.000 title description 4
• APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 365
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
• 201000010099 disease Diseases 0.000 claims abstract description 56
• 239000005441 aurora Substances 0.000 claims abstract description 37
• 230000001404 mediated effect Effects 0.000 claims abstract description 22
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 15
• 108060006633 protein kinase Proteins 0.000 claims abstract description 15
• 125000003118 aryl group Chemical group 0.000 claims description 530
• 125000001072 heteroaryl group Chemical group 0.000 claims description 520
• 125000000217 alkyl group Chemical group 0.000 claims description 465
• 229910052739 hydrogen Inorganic materials 0.000 claims description 463
• 239000001257 hydrogen Substances 0.000 claims description 457
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 236
• 229910052757 nitrogen Inorganic materials 0.000 claims description 165
• 125000002252 acyl group Chemical group 0.000 claims description 158
• 125000000623 heterocyclic group Chemical group 0.000 claims description 157
• 229910052736 halogen Inorganic materials 0.000 claims description 145
• 150000002367 halogens Chemical group 0.000 claims description 145
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
• -1 heteroaliphatic Chemical group 0.000 claims description 83
• 239000000203 mixture Substances 0.000 claims description 76
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 72
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 70
• 125000004432 carbon atom Chemical group C* 0.000 claims description 68
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 64
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 63
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
• 229910052801 chlorine Inorganic materials 0.000 claims description 52
• 229910052731 fluorine Inorganic materials 0.000 claims description 52
• 125000003342 alkenyl group Chemical group 0.000 claims description 50
• 125000001188 haloalkyl group Chemical group 0.000 claims description 50
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
• 125000000304 alkynyl group Chemical group 0.000 claims description 45
• 125000001931 aliphatic group Chemical group 0.000 claims description 42
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 41
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
• 238000000034 method Methods 0.000 claims description 38
• 229910052799 carbon Inorganic materials 0.000 claims description 37
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 35
• 125000002723 alicyclic group Chemical group 0.000 claims description 35
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
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• 229940124597 therapeutic agent Drugs 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 102000003989 Aurora kinases Human genes 0.000 claims description 8
• 108090000433 Aurora kinases Proteins 0.000 claims description 8
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 8
• 239000002552 dosage form Substances 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 125000005647 linker group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 239000003981 vehicle Substances 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
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• 125000004001 thioalkyl group Chemical group 0.000 claims description 5
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• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
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• 125000004423 acyloxy group Chemical group 0.000 claims description 3
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• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 208000023275 Autoimmune disease Diseases 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000005518 carboxamido group Chemical group 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
• 230000002062 proliferating effect Effects 0.000 claims description 2
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
• 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 98
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 16
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• 230000003612 virological effect Effects 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 21
• 238000011282 treatment Methods 0.000 abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 297
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 64
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