JP2007502304A5 - - Google Patents
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- JP2007502304A5 JP2007502304A5 JP2006523419A JP2006523419A JP2007502304A5 JP 2007502304 A5 JP2007502304 A5 JP 2007502304A5 JP 2006523419 A JP2006523419 A JP 2006523419A JP 2006523419 A JP2006523419 A JP 2006523419A JP 2007502304 A5 JP2007502304 A5 JP 2007502304A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- nhc
- heterocarbocyclyl
- aryl
- Prior art date
- 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.)
- Granted
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- -1 heterocarbocyclyl Chemical group 0.000 claims description 111
- 102000004245 Proteasome Endopeptidase Complex Human genes 0.000 claims description 14
- 108090000708 Proteasome Endopeptidase Complex Proteins 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 102000004169 proteins and genes Human genes 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000017854 proteolysis Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 230000002797 proteolythic effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 200
- 150000001875 compounds Chemical class 0.000 claims 98
- 125000004452 carbocyclyl group Chemical group 0.000 claims 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 37
- 125000000304 alkynyl group Chemical group 0.000 claims 35
- 125000003118 aryl group Chemical group 0.000 claims 35
- 229910052799 carbon Inorganic materials 0.000 claims 35
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims 33
- 125000005843 halogen group Chemical group 0.000 claims 33
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 27
- 125000001188 haloalkyl group Chemical group 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims 24
- 238000000034 method Methods 0.000 claims 19
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 18
- 125000006239 protecting group Chemical group 0.000 claims 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 14
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- MOILFCKRQFQVFS-BDNRQGISSA-N (1r,3s,4r,5r)-4,6,6-trimethylbicyclo[3.1.1]heptane-3,4-diol Chemical group C1[C@@H]2C(C)(C)[C@H]1C[C@H](O)[C@@]2(O)C MOILFCKRQFQVFS-BDNRQGISSA-N 0.000 claims 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 7
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 7
- 241000239366 Euphausiacea Species 0.000 claims 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 7
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000005544 phthalimido group Chemical group 0.000 claims 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 239000000543 intermediate Substances 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 102000040945 Transcription factor Human genes 0.000 claims 2
- 108091023040 Transcription factor Proteins 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 229910052711 selenium Inorganic materials 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- MOILFCKRQFQVFS-OORONAJNSA-N (1s,3r,4s,5s)-4,6,6-trimethylbicyclo[3.1.1]heptane-3,4-diol Chemical compound C1[C@H]2C(C)(C)[C@@H]1C[C@@H](O)[C@]2(O)C MOILFCKRQFQVFS-OORONAJNSA-N 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- JHDMMNYIVVWNOF-UHFFFAOYSA-N 1,2-dicyclohexylethane-1,1-diol Chemical compound C1CCCCC1C(O)(O)CC1CCCCC1 JHDMMNYIVVWNOF-UHFFFAOYSA-N 0.000 claims 1
- CKHLARJSOMXDKL-UHFFFAOYSA-N 1,2-dicyclohexylethane-1,2-diol Chemical group C1CCCCC1C(O)C(O)C1CCCCC1 CKHLARJSOMXDKL-UHFFFAOYSA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- OBGFNGZXMSFPAR-UHFFFAOYSA-N 2,5-dimethylhexane-3,3-diol Chemical compound CC(C)CC(O)(O)C(C)C OBGFNGZXMSFPAR-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 102000044159 Ubiquitin Human genes 0.000 claims 1
- 108090000848 Ubiquitin Proteins 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- FUGIIBWTNARRSF-UHFFFAOYSA-N decane-5,6-diol Chemical compound CCCCC(O)C(O)CCCC FUGIIBWTNARRSF-UHFFFAOYSA-N 0.000 claims 1
- 230000000593 degrading effect Effects 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- IHPDTPWNFBQHEB-UHFFFAOYSA-N hydrobenzoin Chemical compound C=1C=CC=CC=1C(O)C(O)C1=CC=CC=C1 IHPDTPWNFBQHEB-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- DQDWATOXYCARFV-UHFFFAOYSA-M magnesium;2-methanidylpropane;bromide Chemical compound [Mg+2].[Br-].CC(C)[CH2-] DQDWATOXYCARFV-UHFFFAOYSA-M 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- 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 1
- 125000005447 octyloxy 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])O* 0.000 claims 1
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- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
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- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 claims 1
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
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- 238000001042 affinity chromatography Methods 0.000 description 1
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- 2004-08-13 KR KR1020067003068A patent/KR101093880B1/ko not_active Expired - Lifetime
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