CA1083577A - Substitutes n-methylene derivatives of thienamycin - Google Patents

Info

Publication number

CA1083577A

CA1083577A CA266,186A CA266186A CA1083577A CA 1083577 A CA1083577 A CA 1083577A CA 266186 A CA266186 A CA 266186A CA 1083577 A CA1083577 A CA 1083577A

Authority

CA

Canada

Prior art keywords

thienamycin

methyl

solution

carbon atoms

alkyl

Prior art date

1975-11-21

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.)

Expired

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 title claims abstract description 126
• 238000002360 preparation method Methods 0.000 claims abstract description 77
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
• 239000001257 hydrogen Substances 0.000 claims abstract description 42
• 238000000034 method Methods 0.000 claims abstract description 40
• 150000001875 compounds Chemical class 0.000 claims abstract description 37
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
• -1 aminoperfluoroalkyl Chemical group 0.000 claims description 410
• WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 claims description 108
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
• 125000004432 carbon atom Chemical group C* 0.000 claims description 77
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 150000002463 imidates Chemical class 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• FGQSMXLNUMMHOR-UHFFFAOYSA-N methyl methanimidate Chemical compound COC=N FGQSMXLNUMMHOR-UHFFFAOYSA-N 0.000 claims description 5
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 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 3
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
• JMIAPORGEDIDLT-UHFFFAOYSA-N ethyl ethanimidate Chemical compound CCOC(C)=N JMIAPORGEDIDLT-UHFFFAOYSA-N 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims 6
• 125000006021 1-methyl-2-propenyl group Chemical group 0.000 claims 2
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 2
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 94
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 78
• 230000003115 biocidal effect Effects 0.000 abstract description 31
• 125000003118 aryl group Chemical group 0.000 abstract description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 22
• 150000002148 esters Chemical class 0.000 abstract description 22
• 239000003242 anti bacterial agent Substances 0.000 abstract description 14
• 229940088710 antibiotic agent Drugs 0.000 abstract description 14
• 125000003710 aryl alkyl group Chemical group 0.000 abstract description 13
• 150000001408 amides Chemical class 0.000 abstract description 10
• 150000002431 hydrogen Chemical class 0.000 abstract description 10
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 8
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 7
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract description 6
• 125000004475 heteroaralkyl group Chemical group 0.000 abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
• 125000000304 alkynyl group Chemical group 0.000 abstract description 4
• 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract description 4
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 3
• 239000000243 solution Substances 0.000 description 133
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 96
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 93
• 229910001868 water Inorganic materials 0.000 description 66
• 238000006243 chemical reaction Methods 0.000 description 59
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
• 239000008363 phosphate buffer Substances 0.000 description 48
• 239000000047 product Substances 0.000 description 45
• 229940093499 ethyl acetate Drugs 0.000 description 39
• 235000019439 ethyl acetate Nutrition 0.000 description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
• 239000008367 deionised water Substances 0.000 description 31
• 229910021641 deionized water Inorganic materials 0.000 description 31
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 30
• 150000003254 radicals Chemical class 0.000 description 29
• 239000007787 solid Substances 0.000 description 29
• 229910052760 oxygen Inorganic materials 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
• 125000002252 acyl group Chemical group 0.000 description 26
• 229910052757 nitrogen Inorganic materials 0.000 description 25
• 230000002829 reductive effect Effects 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 239000003153 chemical reaction reagent Substances 0.000 description 24
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
• 239000011347 resin Substances 0.000 description 23
• 229920005989 resin Polymers 0.000 description 23
• 239000001301 oxygen Substances 0.000 description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 125000004429 atom Chemical group 0.000 description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 21
• 239000002609 medium Substances 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 20
• 239000007858 starting material Substances 0.000 description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
• 239000002253 acid Substances 0.000 description 19
• 239000011541 reaction mixture Substances 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 18
• 239000010410 layer Substances 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
• 239000011734 sodium Substances 0.000 description 16
• 125000001424 substituent group Chemical group 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 238000003756 stirring Methods 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
• 229910019142 PO4 Inorganic materials 0.000 description 13
• 239000000872 buffer Substances 0.000 description 13
• 235000019441 ethanol Nutrition 0.000 description 13
• 150000004820 halides Chemical class 0.000 description 13
• 239000011780 sodium chloride Substances 0.000 description 13
• 229910052717 sulfur Inorganic materials 0.000 description 13
• 239000005864 Sulphur Substances 0.000 description 12
• 125000003545 alkoxy group Chemical group 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 238000004587 chromatography analysis Methods 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 239000004480 active ingredient Substances 0.000 description 11
• 230000000903 blocking effect Effects 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• 125000005843 halogen group Chemical group 0.000 description 11
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 11
• 239000010452 phosphate Substances 0.000 description 11
• 239000000523 sample Substances 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 238000003556 assay Methods 0.000 description 10
• 125000001309 chloro group Chemical group Cl* 0.000 description 10
• 235000008504 concentrate Nutrition 0.000 description 10
• 239000012141 concentrate Substances 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 235000019198 oils Nutrition 0.000 description 10
• 101150041968 CDC13 gene Proteins 0.000 description 9
• 150000001409 amidines Chemical class 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 8
• 150000008064 anhydrides Chemical class 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 230000007062 hydrolysis Effects 0.000 description 8
• 238000006460 hydrolysis reaction Methods 0.000 description 8
• 150000002500 ions Chemical class 0.000 description 8
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 7
• 125000002619 bicyclic group Chemical group 0.000 description 7
• 230000000975 bioactive effect Effects 0.000 description 7
• 238000010586 diagram Methods 0.000 description 7
• 239000000499 gel Substances 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
• 239000005457 ice water Substances 0.000 description 7
• 230000014759 maintenance of location Effects 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 229940073584 methylene chloride Drugs 0.000 description 7
• 239000002808 molecular sieve Substances 0.000 description 7
• 238000002390 rotary evaporation Methods 0.000 description 7
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
• 241000894007 species Species 0.000 description 7
• 239000006228 supernatant Substances 0.000 description 7
• 229940086542 triethylamine Drugs 0.000 description 7
• 229920001817 Agar Polymers 0.000 description 6
• 241000894006 Bacteria Species 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 239000008272 agar Substances 0.000 description 6
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
• 125000001246 bromo group Chemical group Br* 0.000 description 6
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 6
• 238000000855 fermentation Methods 0.000 description 6
• 230000004151 fermentation Effects 0.000 description 6
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
• TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
• 229910000402 monopotassium phosphate Inorganic materials 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
• 229920002261 Corn starch Polymers 0.000 description 5
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
• 241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
• 239000008101 lactose Substances 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 125000005394 methallyl group Chemical group 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 230000007935 neutral effect Effects 0.000 description 5
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• WGMHMVLZFAJNOT-UHFFFAOYSA-N 1-ethoxyethylideneazanium;chloride Chemical compound [Cl-].CCOC(C)=[NH2+] WGMHMVLZFAJNOT-UHFFFAOYSA-N 0.000 description 4
• 241001453268 Comamonas terrigena Species 0.000 description 4
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
• 108010087702 Penicillinase Proteins 0.000 description 4
• 241000607142 Salmonella Species 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 230000001476 alcoholic effect Effects 0.000 description 4
• 239000002168 alkylating agent Substances 0.000 description 4
• 229940100198 alkylating agent Drugs 0.000 description 4
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• 239000008120 corn starch Substances 0.000 description 4
• 229940099112 cornstarch Drugs 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 125000004122 cyclic group Chemical group 0.000 description 4
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
• 238000001962 electrophoresis Methods 0.000 description 4
• 238000010828 elution Methods 0.000 description 4
• JPUTTYRVDANTBN-UHFFFAOYSA-N ethyl methanimidate;hydrochloride Chemical compound Cl.CCOC=N JPUTTYRVDANTBN-UHFFFAOYSA-N 0.000 description 4
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
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