NO841268L - 7-beta-acylamido-3-cefem-4-karboksylsyreforbindelser, fremgangsmaate til deres fremstilling, farmasoeytiske preparater som inneholder disse forbindelser samt deres anvendelse - Google Patents

Info

Publication number

NO841268L

NO841268L NO841268A NO841268A NO841268L NO 841268 L NO841268 L NO 841268L NO 841268 A NO841268 A NO 841268A NO 841268 A NO841268 A NO 841268A NO 841268 L NO841268 L NO 841268L

Authority

NO

Norway

Prior art keywords

formula

group

compound

lower alkyl

acid

Prior art date

1983-03-31

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• 150000001875 compounds Chemical class 0.000 title claims description 220
• 238000000034 method Methods 0.000 title claims description 66
• 238000002360 preparation method Methods 0.000 title claims description 25
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 13
• -1 2-cephem compound Chemical class 0.000 claims description 521
• 125000000217 alkyl group Chemical group 0.000 claims description 146
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 85
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 72
• 239000000203 mixture Substances 0.000 claims description 69
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical class 0.000 claims description 47
• 238000006243 chemical reaction Methods 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
• 125000000524 functional group Chemical group 0.000 claims description 37
• 159000000000 sodium salts Chemical class 0.000 claims description 34
• 239000000460 chlorine Substances 0.000 claims description 33
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
• 229910052801 chlorine Inorganic materials 0.000 claims description 32
• 238000005917 acylation reaction Methods 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000002252 acyl group Chemical group 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 238000006170 formylation reaction Methods 0.000 claims description 17
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 15
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
• 150000002431 hydrogen Chemical group 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 13
• 238000012546 transfer Methods 0.000 claims description 13
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 125000001931 aliphatic group Chemical group 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 230000000269 nucleophilic effect Effects 0.000 claims description 11
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000006413 ring segment Chemical group 0.000 claims description 10
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 150000004677 hydrates Chemical class 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 230000004962 physiological condition Effects 0.000 claims description 6
• 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims 1
• OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 claims 1
• 239000000463 material Substances 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
• 229910001868 water Inorganic materials 0.000 description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• 239000000243 solution Substances 0.000 description 75
• 239000002253 acid Substances 0.000 description 60
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 43
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• 125000006239 protecting group Chemical group 0.000 description 29
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 125000003277 amino group Chemical group 0.000 description 24
• 238000011282 treatment Methods 0.000 description 24
• 239000002585 base Substances 0.000 description 23
• 239000007858 starting material Substances 0.000 description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 21
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
• 230000010933 acylation Effects 0.000 description 20
• UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 229960000583 acetic acid Drugs 0.000 description 17
• 239000000047 product Substances 0.000 description 16
• 125000001424 substituent group Chemical group 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• 150000007513 acids Chemical class 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
• 150000008064 anhydrides Chemical class 0.000 description 13
• 230000022244 formylation Effects 0.000 description 13
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 13
• 239000002245 particle Substances 0.000 description 13
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
• 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 12
• 229920001429 chelating resin Polymers 0.000 description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 description 12
• 235000011152 sodium sulphate Nutrition 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
• 150000001735 carboxylic acids Chemical class 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 238000002844 melting Methods 0.000 description 11
• 230000008018 melting Effects 0.000 description 11
• 229910052751 metal Inorganic materials 0.000 description 11
• 239000002184 metal Substances 0.000 description 11
• 235000011121 sodium hydroxide Nutrition 0.000 description 11
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 11
• 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 10
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
• 230000002378 acidificating effect Effects 0.000 description 10
• 239000003638 chemical reducing agent Substances 0.000 description 10
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
• 235000019253 formic acid Nutrition 0.000 description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
• 229920005989 resin Polymers 0.000 description 10
• 239000011347 resin Substances 0.000 description 10
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• 238000003776 cleavage reaction Methods 0.000 description 9
• 238000009833 condensation Methods 0.000 description 9
• 230000005494 condensation Effects 0.000 description 9
• 230000032050 esterification Effects 0.000 description 9
• 238000005886 esterification reaction Methods 0.000 description 9
• 238000011065 in-situ storage Methods 0.000 description 9
• 150000007522 mineralic acids Chemical class 0.000 description 9
• 239000007800 oxidant agent Substances 0.000 description 9
• 230000003647 oxidation Effects 0.000 description 9
• 238000007254 oxidation reaction Methods 0.000 description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 9
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 239000012141 concentrate Substances 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000000499 gel Substances 0.000 description 8
• 239000000155 melt Substances 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 239000000377 silicon dioxide Substances 0.000 description 8
• 235000012239 silicon dioxide Nutrition 0.000 description 8
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 7
• 150000001340 alkali metals Chemical class 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 238000010828 elution Methods 0.000 description 7
• 238000010438 heat treatment Methods 0.000 description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• 230000007017 scission Effects 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 125000003282 alkyl amino group Chemical group 0.000 description 6
• 239000011737 fluorine Substances 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• 239000011261 inert gas Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 238000002955 isolation Methods 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 235000011007 phosphoric acid Nutrition 0.000 description 6
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
• 230000001603 reducing effect Effects 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 125000005103 alkyl silyl group Chemical group 0.000 description 5
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
• 239000004305 biphenyl Substances 0.000 description 5
• 235000010290 biphenyl Nutrition 0.000 description 5
• 125000001589 carboacyl group Chemical group 0.000 description 5
• 238000000354 decomposition reaction Methods 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 150000004820 halides Chemical class 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 239000011630 iodine Chemical group 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
• 230000007935 neutral effect Effects 0.000 description 5
• 150000002825 nitriles Chemical class 0.000 description 5
• 239000012299 nitrogen atmosphere Substances 0.000 description 5
• 150000007524 organic acids Chemical class 0.000 description 5
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 239000011780 sodium chloride Substances 0.000 description 5
• 238000001179 sorption measurement Methods 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• FUKBBSIRGOFGAQ-LURJTMIESA-N (2s)-2-[5-amino-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-thiazol-4-yl]-2-formamidoacetic acid Chemical compound CC(C)(C)OC(=O)C1=NC([C@H](NC=O)C(O)=O)=C(N)S1 FUKBBSIRGOFGAQ-LURJTMIESA-N 0.000 description 4
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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