PT1888584E - Compostos tricíclicos à base de 1,6-di-hidro-1,3,5,6- tetraaza-as-indaceno e composições farmacêuticas que os compreendem, enquanto inibidores da actividade da enzima ikk - Google Patents

Info

Publication number

PT1888584E

PT1888584E PT06759417T PT06759417T PT1888584E PT 1888584 E PT1888584 E PT 1888584E PT 06759417 T PT06759417 T PT 06759417T PT 06759417 T PT06759417 T PT 06759417T PT 1888584 E PT1888584 E PT 1888584E

Authority

PT

Portugal

Prior art keywords

alkyl

heteroaryl

aryl

cycloalkyl

independently

Prior art date

2005-05-10

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 266
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
• 230000000694 effects Effects 0.000 title description 9
• 239000003112 inhibitor Substances 0.000 title description 7
• 102000004190 Enzymes Human genes 0.000 title description 4
• 108090000790 Enzymes Proteins 0.000 title description 4
• PATOMBNPWNCUCQ-UHFFFAOYSA-N N1C=CC2=C1N=CC1=C2NC=N1 Chemical compound N1C=CC2=C1N=CC1=C2NC=N1 PATOMBNPWNCUCQ-UHFFFAOYSA-N 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 398
• 125000003118 aryl group Chemical group 0.000 claims description 270
• 125000001072 heteroaryl group Chemical group 0.000 claims description 262
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 247
• 125000000623 heterocyclic group Chemical group 0.000 claims description 149
• -1 (heterocyclo) -alkyl Chemical group 0.000 claims description 147
• 125000000304 alkynyl group Chemical group 0.000 claims description 118
• 229910052739 hydrogen Inorganic materials 0.000 claims description 118
• 239000001257 hydrogen Substances 0.000 claims description 113
• 125000003342 alkenyl group Chemical group 0.000 claims description 109
• 125000001188 haloalkyl group Chemical group 0.000 claims description 72
• 229910052757 nitrogen Inorganic materials 0.000 claims description 72
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
• 150000002431 hydrogen Chemical class 0.000 claims description 49
• 125000003545 alkoxy group Chemical group 0.000 claims description 42
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
• 125000005843 halogen group Chemical group 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 229920006395 saturated elastomer Polymers 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000002947 alkylene group Chemical group 0.000 claims description 26
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 18
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000001475 halogen functional group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
• 125000004419 alkynylene group Chemical group 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 125000006413 ring segment Chemical group 0.000 claims description 8
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 6
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Chemical group 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 229910052717 sulfur Chemical group 0.000 claims description 3
• 239000011593 sulfur Chemical group 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
• 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 497
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 270
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 219
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 216
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 199
• 239000011541 reaction mixture Substances 0.000 description 184
• 150000003254 radicals Chemical class 0.000 description 168
• 239000000243 solution Substances 0.000 description 128
• 238000004128 high performance liquid chromatography Methods 0.000 description 121
• 239000002904 solvent Substances 0.000 description 118
• 230000002829 reductive effect Effects 0.000 description 108
• 239000000203 mixture Substances 0.000 description 107
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 105
• 230000014759 maintenance of location Effects 0.000 description 101
• 239000007787 solid Substances 0.000 description 97
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 77
• 235000019439 ethyl acetate Nutrition 0.000 description 75
• 229910001868 water Inorganic materials 0.000 description 65
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• 239000000047 product Substances 0.000 description 55
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• 239000012044 organic layer Substances 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 33
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
• 238000000034 method Methods 0.000 description 26
• YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 26
• 238000005160 1H NMR spectroscopy Methods 0.000 description 25
• 238000001023 centrifugal evaporation Methods 0.000 description 24
• 238000001914 filtration Methods 0.000 description 23
• 239000000543 intermediate Substances 0.000 description 23
• 239000010410 layer Substances 0.000 description 23
• 238000010898 silica gel chromatography Methods 0.000 description 23
• 238000005481 NMR spectroscopy Methods 0.000 description 21
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
• 238000003818 flash chromatography Methods 0.000 description 20
• 239000012299 nitrogen atmosphere Substances 0.000 description 20
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
• 239000012267 brine Substances 0.000 description 17
• 239000000706 filtrate Substances 0.000 description 17
• 208000027866 inflammatory disease Diseases 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
• 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 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 14
• 239000007864 aqueous solution Substances 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 235000019341 magnesium sulphate Nutrition 0.000 description 14
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 238000004458 analytical method Methods 0.000 description 10
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• 102100040247 Tumor necrosis factor Human genes 0.000 description 9
• 239000012141 concentrate Substances 0.000 description 9
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• 108090000623 proteins and genes Proteins 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 9
• 238000004809 thin layer chromatography Methods 0.000 description 9
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 9
• 239000003039 volatile agent Substances 0.000 description 9
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
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• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
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• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 238000004440 column chromatography Methods 0.000 description 7
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 7
• 238000002953 preparative HPLC Methods 0.000 description 7
• 238000006467 substitution reaction Methods 0.000 description 7
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 7
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 6
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• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
• 238000006722 reduction reaction Methods 0.000 description 6
• 125000000547 substituted alkyl group Chemical group 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
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• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
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