UA82876C2 - Hydroxamates, pharmaceutical composition and method for cancer treatment - Google Patents

Info

Publication number

UA82876C2

UA82876C2 UAA200510426A UAA200510426A UA82876C2 UA 82876 C2 UA82876 C2 UA 82876C2 UA A200510426 A UAA200510426 A UA A200510426A UA A200510426 A UAA200510426 A UA A200510426A UA 82876 C2 UA82876 C2 UA 82876C2

Authority

UA

Ukraine

Prior art keywords

hydroxy

benzamide

ethoxy

ylcarbonylamino

benzofuran

Prior art date

2003-04-07

Links

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• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 40
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
• 206010028980 Neoplasm Diseases 0.000 title claims description 27
• 201000011510 cancer Diseases 0.000 title claims description 24
• 150000001875 compounds Chemical class 0.000 claims abstract description 246
• 239000003112 inhibitor Substances 0.000 claims abstract description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
• 201000010099 disease Diseases 0.000 claims abstract description 26
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 835
• -1 o hydroxyalkoxyalkyl Chemical group 0.000 claims description 538
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 193
• 125000000217 alkyl group Chemical group 0.000 claims description 100
• 125000001072 heteroaryl group Chemical group 0.000 claims description 76
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 61
• 125000001188 haloalkyl group Chemical group 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 53
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 47
• 239000001257 hydrogen Substances 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 38
• 125000005843 halogen group Chemical group 0.000 claims description 38
• 125000004432 carbon atom Chemical group C* 0.000 claims description 36
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 32
• 239000000203 mixture Substances 0.000 claims description 31
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 30
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 27
• 125000006413 ring segment Chemical group 0.000 claims description 27
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 20
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 19
• 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 241001465754 Metazoa Species 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 229940123934 Reductase inhibitor Drugs 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 10
• 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 10
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
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• 231100000599 cytotoxic agent Toxicity 0.000 claims description 9
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• 229940123468 Transferase inhibitor Drugs 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 239000003968 dna methyltransferase inhibitor Substances 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 238000001959 radiotherapy Methods 0.000 claims description 6
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 6
• VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims description 5
• 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims description 5
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
• 229940126190 DNA methyltransferase inhibitor Drugs 0.000 claims description 5
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 5
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• 125000004450 alkenylene group Chemical group 0.000 claims description 2
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 2
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
• 208000031295 Animal disease Diseases 0.000 claims 1
• 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 1
• 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 1
• 235000011449 Rosa Nutrition 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 125000003107 substituted aryl group Chemical group 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
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• 239000000243 solution Substances 0.000 description 64
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 150000003254 radicals Chemical class 0.000 description 41
• 239000011541 reaction mixture Substances 0.000 description 41
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 38
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 230000015572 biosynthetic process Effects 0.000 description 27
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 125000003282 alkyl amino group Chemical group 0.000 description 24
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 24
• 239000007787 solid Substances 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 125000004663 dialkyl amino group Chemical group 0.000 description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
• 239000002253 acid Substances 0.000 description 21
• 210000004027 cell Anatomy 0.000 description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
• 235000019439 ethyl acetate Nutrition 0.000 description 19
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 239000004215 Carbon black (E152) Substances 0.000 description 17
• 229930195733 hydrocarbon Natural products 0.000 description 17
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 17
• 125000001153 fluoro group Chemical group F* 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 125000005549 heteroarylene group Chemical group 0.000 description 14
• 125000000842 isoxazolyl group Chemical group 0.000 description 14
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• 239000003814 drug Substances 0.000 description 13
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
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• 125000001309 chloro group Chemical group Cl* 0.000 description 12
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 12
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• 102000004316 Oxidoreductases Human genes 0.000 description 11
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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• 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
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
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