PT1515983E - Macrociclos de amida antibacterianos - Google Patents

Info

Publication number

PT1515983E

PT1515983E PT03738012T PT03738012T PT1515983E PT 1515983 E PT1515983 E PT 1515983E PT 03738012 T PT03738012 T PT 03738012T PT 03738012 T PT03738012 T PT 03738012T PT 1515983 E PT1515983 E PT 1515983E

Authority

PT

Portugal

Prior art keywords

hydrogen

alkyl

substituents

amino

equal

Prior art date

2002-06-17

Links

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• -1 amide macrocycles Chemical class 0.000 title claims abstract description 247
• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 10
• 238000000034 method Methods 0.000 claims abstract description 158
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 11
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 239000003814 drug Substances 0.000 claims abstract description 9
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 7
• 238000011321 prophylaxis Methods 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 160
• 229910052739 hydrogen Inorganic materials 0.000 claims description 132
• 239000001257 hydrogen Substances 0.000 claims description 131
• 125000001424 substituent group Chemical group 0.000 claims description 94
• 150000002431 hydrogen Chemical group 0.000 claims description 83
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 48
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 44
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 40
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 31
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 29
• 238000002360 preparation method Methods 0.000 claims description 27
• 125000003282 alkyl amino group Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
• 235000001014 amino acid Nutrition 0.000 claims description 18
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
• 150000001413 amino acids Chemical class 0.000 claims description 17
• 125000003277 amino group Chemical group 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 230000008569 process Effects 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 14
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 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 12
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 9
• 235000008206 alpha-amino acids Nutrition 0.000 claims description 8
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
• 150000001371 alpha-amino acids Chemical class 0.000 claims description 7
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
• 125000003275 alpha amino acid group Chemical group 0.000 claims description 5
• 150000001409 amidines Chemical class 0.000 claims description 5
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 5
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 11
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 153
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 126
• 239000000243 solution Substances 0.000 description 116
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 84
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 75
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 72
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 63
• 239000003480 eluent Substances 0.000 description 63
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 54
• 239000000203 mixture Substances 0.000 description 52
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 48
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
• 238000006243 chemical reaction Methods 0.000 description 48
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 42
• 235000019253 formic acid Nutrition 0.000 description 42
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 38
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 239000002904 solvent Substances 0.000 description 36
• 238000004128 high performance liquid chromatography Methods 0.000 description 35
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 31
• 238000003756 stirring Methods 0.000 description 31
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 30
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 27
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 27
• 239000012074 organic phase Substances 0.000 description 26
• 239000000047 product Substances 0.000 description 26
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 25
• 238000005481 NMR spectroscopy Methods 0.000 description 24
• 229910052786 argon Inorganic materials 0.000 description 24
• 239000012043 crude product Substances 0.000 description 23
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 22
• 229960001701 chloroform Drugs 0.000 description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
• 125000004432 carbon atom Chemical group C* 0.000 description 20
• 239000002585 base Substances 0.000 description 19
• 238000012360 testing method Methods 0.000 description 19
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 239000007821 HATU Substances 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 229910052938 sodium sulfate Inorganic materials 0.000 description 17
• 235000011152 sodium sulphate Nutrition 0.000 description 17
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 238000003786 synthesis reaction Methods 0.000 description 16
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• 230000015572 biosynthetic process Effects 0.000 description 15
• 238000000825 ultraviolet detection Methods 0.000 description 15
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 14
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• 208000015181 infectious disease Diseases 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 229940024606 amino acid Drugs 0.000 description 13
• 125000000539 amino acid group Chemical group 0.000 description 13
• 238000013519 translation Methods 0.000 description 13
• XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
• 239000003960 organic solvent Substances 0.000 description 12
• IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 12
• 238000005160 1H NMR spectroscopy Methods 0.000 description 11
• 230000008859 change Effects 0.000 description 11
• 229930195733 hydrocarbon Natural products 0.000 description 11
• 150000002430 hydrocarbons Chemical class 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 11
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 10
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• 230000014616 translation Effects 0.000 description 10
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 9
• 125000006242 amine protecting group Chemical group 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 9
• 150000008282 halocarbons Chemical class 0.000 description 9
• 125000005842 heteroatom Chemical group 0.000 description 9
• 238000000338 in vitro Methods 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 239000011780 sodium chloride Substances 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 239000003643 water by type Substances 0.000 description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
• 239000004480 active ingredient Substances 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 239000013612 plasmid Substances 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 235000011181 potassium carbonates Nutrition 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• XOSVVZQCJBMLPH-KRWDZBQOSA-N (2s)-3-(5-iodo-2-phenylmethoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC(I)=CC=C1OCC1=CC=CC=C1 XOSVVZQCJBMLPH-KRWDZBQOSA-N 0.000 description 7
• 235000011054 acetic acid Nutrition 0.000 description 7
• 230000004913 activation Effects 0.000 description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
• 239000008346 aqueous phase Substances 0.000 description 7
• 239000000872 buffer Substances 0.000 description 7
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
• 229910000024 caesium carbonate Inorganic materials 0.000 description 7
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 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 7
• 238000001035 drying Methods 0.000 description 7
• 238000002199 high-resolution Fourier transform ion cyclotron resonance mass spectrometry Methods 0.000 description 7
• 238000004007 reversed phase HPLC Methods 0.000 description 7
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
• LHFTUYBCCNRGQH-NRFANRHFSA-N (2s)-3-(5-iodo-2-phenylmethoxyphenyl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC(I)=CC=C1OCC1=CC=CC=C1 LHFTUYBCCNRGQH-NRFANRHFSA-N 0.000 description 6
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• 241000588724 Escherichia coli Species 0.000 description 6
• 239000003513 alkali Substances 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 125000005129 aryl carbonyl group Chemical group 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 238000010790 dilution Methods 0.000 description 6
• 239000012895 dilution Substances 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 229910000029 sodium carbonate Inorganic materials 0.000 description 6
• 235000011121 sodium hydroxide Nutrition 0.000 description 6
• 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 6
• 238000013518 transcription Methods 0.000 description 6
• 230000035897 transcription Effects 0.000 description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
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