JP2014503570A - 新規な５−アルキニル−ピリジン - Google Patents

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Publication number

JP2014503570A

JP2014503570A JP2013550871A JP2013550871A JP2014503570A JP 2014503570 A JP2014503570 A JP 2014503570A JP 2013550871 A JP2013550871 A JP 2013550871A JP 2013550871 A JP2013550871 A JP 2013550871A JP 2014503570 A JP2014503570 A JP 2014503570A

Authority

JP

Japan

Prior art keywords

alkyl

halogen

independently

groups

butyl

Prior art date

2011-01-26

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.)

Pending

Links

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• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 27
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 48
• 201000011510 cancer Diseases 0.000 claims abstract description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 290
• -1 iso- butyl - Chemical class 0.000 claims description 233
• 150000001875 compounds Chemical class 0.000 claims description 154
• 229910052736 halogen Inorganic materials 0.000 claims description 101
• 150000002367 halogens Chemical class 0.000 claims description 101
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 98
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 95
• 125000000623 heterocyclic group Chemical group 0.000 claims description 88
• 125000003118 aryl group Chemical group 0.000 claims description 71
• 125000001072 heteroaryl group Chemical group 0.000 claims description 69
• 239000000203 mixture Substances 0.000 claims description 67
• 125000003342 alkenyl group Chemical group 0.000 claims description 49
• 125000000304 alkynyl group Chemical group 0.000 claims description 48
• 229920006395 saturated elastomer Polymers 0.000 claims description 34
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 19
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 238000011282 treatment Methods 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 7
• 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 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical group OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 10
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• 239000003112 inhibitor Substances 0.000 abstract description 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 239000011541 reaction mixture Substances 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
• 239000000543 intermediate Substances 0.000 description 53
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
• 210000004027 cell Anatomy 0.000 description 42
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• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 35
• 239000000047 product Substances 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 125000004432 carbon atom Chemical group C* 0.000 description 33
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
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• 238000006243 chemical reaction Methods 0.000 description 26
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• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 20
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 20
• 239000012043 crude product Substances 0.000 description 19
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• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
• 108091007960 PI3Ks Proteins 0.000 description 16
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• 229910000027 potassium carbonate Inorganic materials 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 15
• 125000000753 cycloalkyl group Chemical group 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 125000000392 cycloalkenyl group Chemical group 0.000 description 14
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 14
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 14
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 13
• 239000012071 phase Substances 0.000 description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
• 238000005516 engineering process Methods 0.000 description 12
• 238000006467 substitution reaction Methods 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 125000002947 alkylene group Chemical group 0.000 description 11
• 239000012300 argon atmosphere Substances 0.000 description 11
• 230000037361 pathway Effects 0.000 description 11
• 238000004007 reversed phase HPLC Methods 0.000 description 11
• 206010006187 Breast cancer Diseases 0.000 description 10
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• 235000019439 ethyl acetate Nutrition 0.000 description 10
• 125000001183 hydrocarbyl group Chemical group 0.000 description 10
• 239000002609 medium Substances 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
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• 125000004122 cyclic group Chemical group 0.000 description 9
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• 238000000746 purification Methods 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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• 238000003556 assay Methods 0.000 description 8
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• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 8
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• 229920002261 Corn starch Polymers 0.000 description 7
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• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
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