CS199273B2

CS199273B2 - Způsob přípravy 7-(a,a-disubstituovaných-acetamido)-3- -substituovaných-3-cefem-4-karboxylových kyselin

Způsob přípravy 7-(a,a-disubstituovaných-acetamido)-3- -substituovaných-3-cefem-4-karboxylových kyselin Download PDF

Info

Publication number: CS199273B2
Authority: CS; Czechoslovakia
Prior art keywords: group; carbon atoms; compound; alkanoyloxy; isomer
Prior art date: 1975-02-04

Application number

CS71276A

Other languages

Czech (cs)

English (en)

Inventor

Takao Takaya

Takashi Masugi

Hisashi Takasugi

Hiromu Kochi

Original Assignee

Fujisawa Pharmaceutical Co

Priority date

1975-02-04

Filing date

1976-02-04

Publication date

1980-07-31

1975-02-04 Priority claimed from JP50015191A external-priority patent/JPS5191284A/ja

1975-04-21 Priority claimed from JP50048833A external-priority patent/JPS51125398A/ja

1975-07-07 Priority claimed from JP50083867A external-priority patent/JPS527988A/ja

1976-02-04 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1980-07-31 Publication of CS199273B2 publication Critical patent/CS199273B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 165
229910052739 hydrogen Inorganic materials 0.000 claims description 163
-1 carbamoyloxy Chemical group 0.000 claims description 147
150000003839 salts Chemical class 0.000 claims description 73
125000004432 carbon atom Chemical group C* 0.000 claims description 71
238000006243 chemical reaction Methods 0.000 claims description 58
125000002252 acyl group Chemical group 0.000 claims description 40
125000004423 acyloxy group Chemical group 0.000 claims description 36
238000000034 method Methods 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 26
238000002360 preparation method Methods 0.000 claims description 19
238000003379 elimination reaction Methods 0.000 claims description 18
125000003435 aroyl group Chemical group 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
150000008065 acid anhydrides Chemical class 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
230000008030 elimination Effects 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 2
101100289061 Drosophila melanogaster lili gene Proteins 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
238000002329 infrared spectrum Methods 0.000 description 72
239000000203 mixture Substances 0.000 description 72
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 64
239000000243 solution Substances 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
229960001760 dimethyl sulfoxide Drugs 0.000 description 44
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
238000001816 cooling Methods 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 18
239000011734 sodium Substances 0.000 description 18
229910052708 sodium Inorganic materials 0.000 description 18
238000003756 stirring Methods 0.000 description 18
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 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
150000007514 bases Chemical class 0.000 description 15
238000001914 filtration Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 14
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 13
239000007858 starting material Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
150000001242 acetic acid derivatives Chemical class 0.000 description 7
239000012467 final product Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
OPQVNXDBBSJNBJ-PVQCJRHBSA-N (6R)-7-[[2-hydroxyimino-2-(3-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound ON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)C1=CC(=CC=C1)O OPQVNXDBBSJNBJ-PVQCJRHBSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
239000008272 agar Substances 0.000 description 5
229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
150000008041 alkali metal carbonates Chemical class 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
NIGSPCOEBMYIBR-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(3-hydroxyphenyl)acetic acid Chemical compound ClC(Cl)C(=O)ON=C(C(=O)O)C1=CC=CC(O)=C1 NIGSPCOEBMYIBR-UHFFFAOYSA-N 0.000 description 4
YNTPIKSPJIQDTM-UHFFFAOYSA-N 2-hydroxyimino-2-(3-hydroxyphenyl)acetic acid Chemical compound ON=C(C(O)=O)C1=CC=CC(O)=C1 YNTPIKSPJIQDTM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
125000005270 trialkylamine group Chemical group 0.000 description 4
239000011701 zinc Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
NIVQTMCOFWYSQN-UHFFFAOYSA-N 2-(2,2-dimethylpropanoyloxyimino)-2-(3-hydroxyphenyl)acetic acid Chemical compound CC(C)(C)C(=O)ON=C(C(O)=O)C1=CC=CC(O)=C1 NIVQTMCOFWYSQN-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ULGNNGRBOQYCDH-UHFFFAOYSA-N 2-hydroxyimino-2-[4-hydroxy-3-(methanesulfonamido)phenyl]acetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=NO)C(O)=O)=CC=C1O ULGNNGRBOQYCDH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
230000002411 adverse Effects 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000013078 crystal Substances 0.000 description 3
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DXSJUYSAIGOMOB-XPKAQORNSA-N (6R)-7-[[2-acetyloxyimino-2-(3-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C)(=O)ON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)C1=CC(=CC=C1)O DXSJUYSAIGOMOB-XPKAQORNSA-N 0.000 description 2
UTJBVDHFYIVQOQ-XPKAQORNSA-N (6R)-7-[[2-ethoxycarbonyloxyimino-2-(3-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C)OC(=O)ON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)C1=CC(=CC=C1)O UTJBVDHFYIVQOQ-XPKAQORNSA-N 0.000 description 2
XUTQHTOXGKVJPN-XCGJVMPOSA-N (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 XUTQHTOXGKVJPN-XCGJVMPOSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 2
REIGARMSUIDPOX-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-hydroxyphenyl)acetic acid Chemical compound ClC(Cl)C(=O)ON=C(C(=O)O)C1=CC=C(O)C=C1 REIGARMSUIDPOX-UHFFFAOYSA-N 0.000 description 2
NBDYDHVCTKPDRI-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=CC(O)=C1 NBDYDHVCTKPDRI-UHFFFAOYSA-N 0.000 description 2
JOZCNWTTZMKMKP-UHFFFAOYSA-N 2-(3-nitro-4-phenylmethoxyphenyl)-2-oxoacetic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)C(=O)O)=CC=C1OCC1=CC=CC=C1 JOZCNWTTZMKMKP-UHFFFAOYSA-N 0.000 description 2
PWURXZPHZHSYPJ-UHFFFAOYSA-N 2-[3-(methanesulfonamido)-4-phenylmethoxyphenyl]-2-oxoacetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=O)C(O)=O)=CC=C1OCC1=CC=CC=C1 PWURXZPHZHSYPJ-UHFFFAOYSA-N 0.000 description 2
VVNFXLVZTCJWKX-UHFFFAOYSA-N 2-[4-hydroxy-3-(methanesulfonamido)phenyl]-2-oxoacetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=O)C(O)=O)=CC=C1O VVNFXLVZTCJWKX-UHFFFAOYSA-N 0.000 description 2
CQXXFDXFOYSHGN-UHFFFAOYSA-N 2-hydroxyimino-2-(4-hydroxy-3-nitrophenyl)acetic acid Chemical compound ON=C(C(O)=O)C1=CC=C(O)C([N+]([O-])=O)=C1 CQXXFDXFOYSHGN-UHFFFAOYSA-N 0.000 description 2
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
125000005116 aryl carbamoyl group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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