AU2013224848B2 - Pyrazolo - triazine derivatives as selective cyclin- dependent kinase inhibitors - Google Patents

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Publication number

AU2013224848B2

AU2013224848B2 AU2013224848A AU2013224848A AU2013224848B2 AU 2013224848 B2 AU2013224848 B2 AU 2013224848B2 AU 2013224848 A AU2013224848 A AU 2013224848A AU 2013224848 A AU2013224848 A AU 2013224848A AU 2013224848 B2 AU2013224848 B2 AU 2013224848B2

Authority

AU

Australia

Prior art keywords

triazin

pyrazolo

amine

isopropyl

benzyl

Prior art date

2012-03-01

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.)

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• PEYVWBGHBCDXRT-UHFFFAOYSA-N N1=NNC2=CN=NC2=C1 Chemical class N1=NNC2=CN=NC2=C1 PEYVWBGHBCDXRT-UHFFFAOYSA-N 0.000 title description 3
• 239000002875 cyclin dependent kinase inhibitor Substances 0.000 title 1
• 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 title 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
• 201000010099 disease Diseases 0.000 claims abstract description 51
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 238000011321 prophylaxis Methods 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 230000002062 proliferating effect Effects 0.000 claims abstract description 15
• JUXWUYWPUDKPSD-UHFFFAOYSA-N pyrazolo[1,5-a][1,3,5]triazine Chemical class N1=CN=CN2N=CC=C21 JUXWUYWPUDKPSD-UHFFFAOYSA-N 0.000 claims abstract description 10
• 239000013543 active substance Substances 0.000 claims abstract description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 618
• 125000001424 substituent group Chemical group 0.000 claims description 311
• -1 tetrahydrothienyi Chemical group 0.000 claims description 262
• 229910052757 nitrogen Inorganic materials 0.000 claims description 177
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 166
• 150000001875 compounds Chemical class 0.000 claims description 154
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 154
• 125000000623 heterocyclic group Chemical group 0.000 claims description 109
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 102
• 125000003003 spiro group Chemical group 0.000 claims description 88
• 229910052799 carbon Inorganic materials 0.000 claims description 80
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 59
• QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 58
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 56
• 125000004432 carbon atom Chemical group C* 0.000 claims description 55
• 239000000203 mixture Substances 0.000 claims description 49
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 44
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 44
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 42
• 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 40
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 38
• 206010028980 Neoplasm Diseases 0.000 claims description 36
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
• 102100026810 Cyclin-dependent kinase 7 Human genes 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 27
• 101000911952 Homo sapiens Cyclin-dependent kinase 7 Proteins 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
• 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims description 22
• 125000002837 carbocyclic group Chemical group 0.000 claims description 21
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 20
• 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
• 210000004027 cell Anatomy 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 239000004480 active ingredient Substances 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
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• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 13
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 12
• 229920006395 saturated elastomer Polymers 0.000 claims description 12
• 201000009030 Carcinoma Diseases 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 201000001441 melanoma Diseases 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
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• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 7
• 125000005605 benzo group Chemical group 0.000 claims description 7
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• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 125000006519 CCH3 Chemical group 0.000 claims description 6
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 6
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
• 206010017758 gastric cancer Diseases 0.000 claims description 6
• 201000005962 mycosis fungoides Diseases 0.000 claims description 6
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 201000011549 stomach cancer Diseases 0.000 claims description 6
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
• 208000017604 Hodgkin disease Diseases 0.000 claims description 5
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 5
• 206010025323 Lymphomas Diseases 0.000 claims description 5
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 5
• 201000000849 skin cancer Diseases 0.000 claims description 5
• MGFLRUYNACZFMH-UHFFFAOYSA-N 2-(4-aminopiperidin-1-yl)-8-propan-2-yl-n-[(2-pyrazol-1-ylphenyl)methyl]pyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound N=1C(N2CCC(N)CC2)=NC2=C(C(C)C)C=NN2C=1NCC1=CC=CC=C1N1C=CC=N1 MGFLRUYNACZFMH-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 4
• 206010003571 Astrocytoma Diseases 0.000 claims description 4
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• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
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• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
• 230000009826 neoplastic cell growth Effects 0.000 claims description 4
• 125000000466 oxiranyl group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 206010038038 rectal cancer Diseases 0.000 claims description 4
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 3
• 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
• VFQLJKJTLNSFCU-UHFFFAOYSA-N 2,6-diazaspiro[3.3]heptan-2-yl-[8-propan-2-yl-4-[(2-pyrazol-1-ylphenyl)methylamino]pyrazolo[1,5-a][1,3,5]triazin-2-yl]methanone Chemical compound N=1C(C(=O)N2CC3(CNC3)C2)=NC2=C(C(C)C)C=NN2C=1NCC1=CC=CC=C1N1C=CC=N1 VFQLJKJTLNSFCU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 3
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• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
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• 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 3
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• OWGCQVDTQVLGAG-GZMMZOGISA-N n-[(2-methylsulfinylphenyl)methyl]-2-[(3r)-piperidin-3-yl]oxy-8-propan-2-ylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound N=1C(O[C@H]2CNCCC2)=NC2=C(C(C)C)C=NN2C=1NCC1=CC=CC=C1S(C)=O OWGCQVDTQVLGAG-GZMMZOGISA-N 0.000 claims description 3
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• YPRXIOHDHGASQP-JOCHJYFZSA-N 1-benzyl-3-[2-[[[2-[(3r)-piperidin-3-yl]oxy-8-propan-2-ylpyrazolo[1,5-a][1,3,5]triazin-4-yl]amino]methyl]phenyl]urea Chemical compound N=1C(O[C@H]2CNCCC2)=NC2=C(C(C)C)C=NN2C=1NCC1=CC=CC=C1NC(=O)NCC1=CC=CC=C1 YPRXIOHDHGASQP-JOCHJYFZSA-N 0.000 claims description 2
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