DK3180339T3 - 6-alkynylpyridine derivatives as SMAC mimetics - Google Patents

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Publication number

DK3180339T3

DK3180339T3 DK15747820.7T DK15747820T DK3180339T3 DK 3180339 T3 DK3180339 T3 DK 3180339T3 DK 15747820 T DK15747820 T DK 15747820T DK 3180339 T3 DK3180339 T3 DK 3180339T3

Authority

DK

Denmark

Prior art keywords

salts

compound

formula

alkyl

compounds

Prior art date

2014-08-11

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• 229940075439 smac mimetic Drugs 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 116
• 150000003839 salts Chemical class 0.000 claims description 47
• 206010028980 Neoplasm Diseases 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 10
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims description 8
• 208000022679 triple-negative breast carcinoma Diseases 0.000 claims description 8
• 239000000969 carrier Substances 0.000 claims description 7
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 210000004556 brain Anatomy 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 210000002307 prostate Anatomy 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 230000002611 ovarian Effects 0.000 claims 1
• 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
• -1 2-pentyl Chemical group 0.000 description 188
• 239000000203 mixture Substances 0.000 description 52
• 125000004432 carbon atom Chemical group C* 0.000 description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• 229920006395 saturated elastomer Polymers 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 125000003118 aryl group Chemical group 0.000 description 18
• 238000000034 method Methods 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
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• 239000013543 active substance Substances 0.000 description 16
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 16
• 125000000623 heterocyclic group Chemical group 0.000 description 14
• 230000005764 inhibitory process Effects 0.000 description 14
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• 125000000392 cycloalkenyl group Chemical group 0.000 description 13
• 125000000753 cycloalkyl group Chemical group 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 239000000047 product Substances 0.000 description 12
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• 125000002947 alkylene group Chemical group 0.000 description 10
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• 125000001183 hydrocarbyl group Chemical group 0.000 description 10
• 230000002401 inhibitory effect Effects 0.000 description 10
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 125000004450 alkenylene group Chemical group 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• 239000012300 argon atmosphere Substances 0.000 description 6
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
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• 229920002261 Corn starch Polymers 0.000 description 5
• 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 5
• 125000004419 alkynylene group Chemical group 0.000 description 5
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• 125000000262 haloalkenyl group Chemical group 0.000 description 5
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• 235000019359 magnesium stearate Nutrition 0.000 description 5
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• 229910052623 talc Inorganic materials 0.000 description 5
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• 208000023275 Autoimmune disease Diseases 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 4
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• 229920002472 Starch Polymers 0.000 description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
• CZCNJQZKZPFVAQ-UHFFFAOYSA-N [6-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-[2-tri(propan-2-yl)silylethynyl]pyridin-3-yl]boronic acid Chemical compound CC(C)[Si](C(C)C)(C(C)C)C#CC1=NC(NC(=O)C(C)N(C)C(=O)OC(C)(C)C)=CC=C1B(O)O CZCNJQZKZPFVAQ-UHFFFAOYSA-N 0.000 description 4
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