TWI329645B - Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors - Google Patents

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Publication number

TWI329645B

TWI329645B TW092124336A TW92124336A TWI329645B TW I329645 B TWI329645 B TW I329645B TW 092124336 A TW092124336 A TW 092124336A TW 92124336 A TW92124336 A TW 92124336A TW I329645 B TWI329645 B TW I329645B

Authority

TW

Taiwan

Prior art keywords

group

aryl

compound

alkyl

doc

Prior art date

2002-09-04

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• 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 title description 7
• 239000002875 cyclin dependent 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 description 136
• 125000003118 aryl group Chemical group 0.000 claims description 84
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 150000003839 salts Chemical class 0.000 claims description 42
• 239000000460 chlorine Substances 0.000 claims description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• -1 4-(methylsulfonyl)phenyl Chemical group 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 206010028980 Neoplasm Diseases 0.000 claims description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 108091007914 CDKs Proteins 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 15
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 15
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
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• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
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• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 4
• PLHJCIYEEKOWNM-HHHXNRCGSA-N tipifarnib Chemical compound CN1C=NC=C1[C@](N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-HHHXNRCGSA-N 0.000 claims description 4
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• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
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• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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• DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 claims description 2
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• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 2
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