CA1340499C - Derives thiazolylique, utiles come intermediaires pour la preparation decepheme et de cephemes - Google Patents

Derives thiazolylique, utiles come intermediaires pour la preparation decepheme et de cephemes

Info

Publication number: CA1340499C
Authority: CA; Canada
Prior art keywords: compound; solution; cephem; acid; syn isomer
Prior art date: 1977-03-14
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 - Lifetime

Application number

CA000616635A

Other languages

English (en)

Inventor

Takao Takaya

Hisashi Takasugi

Kiyoshi Tsuji

Toshiyuki Chiba

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Astellas Pharma Inc

Original Assignee

Fujisawa Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1977-03-14

Filing date

1993-03-31

Publication date

1999-04-13

1978-03-14 Priority claimed from CA000298883A external-priority patent/CA1321580C/fr

1993-03-31 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1998-03-14 Anticipated expiration legal-status Critical

1999-04-13 Application granted granted Critical

1999-04-13 Publication of CA1340499C publication Critical patent/CA1340499C/fr

Status Expired - Lifetime legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title abstract description 16
150000001782 cephems Chemical class 0.000 title abstract description 5
150000001781 cephams Chemical class 0.000 title abstract description 4
125000000335 thiazolyl group Chemical group 0.000 title description 14
150000001875 compounds Chemical class 0.000 claims abstract description 196
150000003839 salts Chemical class 0.000 claims abstract description 65
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 64
125000000217 alkyl group Chemical group 0.000 claims abstract description 49
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 26
125000000304 alkynyl group Chemical group 0.000 claims abstract description 17
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
125000001475 halogen functional group Chemical group 0.000 claims abstract 5
239000002253 acid Substances 0.000 claims description 69
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
GBLKPIKZMXOJAP-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid Chemical compound NC1=NC(C(=NOCCCl)C(O)=O)=CS1 GBLKPIKZMXOJAP-UHFFFAOYSA-N 0.000 claims description 3
JPTAGANPEAENGI-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetic acid Chemical compound CC(C)CON=C(C(O)=O)C1=CSC(N)=N1 JPTAGANPEAENGI-UHFFFAOYSA-N 0.000 claims description 3
ZCPKIBFOMTXZPP-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-pentoxyiminoacetic acid Chemical compound CCCCCON=C(C(O)=O)C1=CSC(N)=N1 ZCPKIBFOMTXZPP-UHFFFAOYSA-N 0.000 claims description 3
VZRKYOWOWILIHD-UHFFFAOYSA-N 2-(2-ethoxy-2-oxoethoxy)imino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid Chemical compound CCOC(=O)CON=C(C(O)=O)C1=CSC(NC=O)=N1 VZRKYOWOWILIHD-UHFFFAOYSA-N 0.000 claims description 3
JLXNDAIQKDEBFW-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetic acid Chemical compound CC(C)CON=C(C(O)=O)C1=CSC(NC=O)=N1 JLXNDAIQKDEBFW-UHFFFAOYSA-N 0.000 claims description 3
LBCGGKOBNAQPRD-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-butoxyiminoacetic acid Chemical compound CCCCON=C(C(O)=O)C1=CSC(N)=N1 LBCGGKOBNAQPRD-UHFFFAOYSA-N 0.000 claims description 2
YGVBWDRXZDWWRT-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-cyclohexyloxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC2CCCCC2)C(O)=O)=C1 YGVBWDRXZDWWRT-UHFFFAOYSA-N 0.000 claims description 2
MGDTVMNKZDJLIS-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-hexoxyiminoacetic acid Chemical compound CCCCCCON=C(C(O)=O)C1=CSC(N)=N1 MGDTVMNKZDJLIS-UHFFFAOYSA-N 0.000 claims description 2
UUHYXGRSWMTMPP-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetic acid Chemical compound NC1=NC(C(=NOCC#C)C(O)=O)=CS1 UUHYXGRSWMTMPP-UHFFFAOYSA-N 0.000 claims description 2
JSKBVWPVMUEVNM-UHFFFAOYSA-N 2-(2-chloroethoxyimino)-2-(2-formamido-1,3-thiazol-4-yl)acetic acid Chemical compound ClCCON=C(C(=O)O)C1=CSC(NC=O)=N1 JSKBVWPVMUEVNM-UHFFFAOYSA-N 0.000 claims description 2
KXGLGLHHMWGCBQ-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid Chemical compound FC(F)(F)CON=C(C(=O)O)C1=CSC(NC=O)=N1 KXGLGLHHMWGCBQ-UHFFFAOYSA-N 0.000 claims description 2
JQRBSMVKVLPDIC-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-octoxyiminoacetic acid Chemical compound CCCCCCCCON=C(C(O)=O)C1=CSC(NC=O)=N1 JQRBSMVKVLPDIC-UHFFFAOYSA-N 0.000 claims description 2
FMTFFWAQTXIWNN-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-pentoxyiminoacetic acid Chemical compound CCCCCON=C(C(O)=O)C1=CSC(NC=O)=N1 FMTFFWAQTXIWNN-UHFFFAOYSA-N 0.000 claims description 2
GLHXPMXKDHFXIZ-UHFFFAOYSA-N 2-cyclohexyloxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid Chemical compound C=1SC(NC=O)=NC=1C(C(=O)O)=NOC1CCCCC1 GLHXPMXKDHFXIZ-UHFFFAOYSA-N 0.000 claims description 2
SBFHSELVKUCJBB-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid Chemical compound NC1=NC(C(=NOCC(F)(F)F)C(O)=O)=CS1 SBFHSELVKUCJBB-UHFFFAOYSA-N 0.000 claims 1
MPZBNNJEDQAKTF-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-(2-ethoxy-2-oxoethoxy)iminoacetic acid Chemical compound CCOC(=O)CON=C(C(O)=O)C1=CSC(N)=N1 MPZBNNJEDQAKTF-UHFFFAOYSA-N 0.000 claims 1
BTBQXVJMMALOJT-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetic acid Chemical compound NC1=NC(C(=NOCC(O)=O)C(O)=O)=CS1 BTBQXVJMMALOJT-UHFFFAOYSA-N 0.000 claims 1
XSQPXYAKVKORFJ-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetic acid Chemical compound CC(C)(C)OC(=O)CON=C(C(O)=O)C1=CSC(N)=N1 XSQPXYAKVKORFJ-UHFFFAOYSA-N 0.000 claims 1
YPRCHXOLEWTKCX-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-hexoxyiminoacetic acid Chemical compound CCCCCCON=C(C(O)=O)C1=CSC(NC=O)=N1 YPRCHXOLEWTKCX-UHFFFAOYSA-N 0.000 claims 1
SLHKAKUSYQYNCP-UHFFFAOYSA-N 2-(carboxymethoxyimino)-2-(2-formamido-1,3-thiazol-4-yl)acetic acid Chemical compound OC(=O)CON=C(C(O)=O)C1=CSC(NC=O)=N1 SLHKAKUSYQYNCP-UHFFFAOYSA-N 0.000 claims 1
AFQFGMQFLQIBNK-UHFFFAOYSA-N 2-prop-2-ynoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound C#CCON=C(C(=O)O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 AFQFGMQFLQIBNK-UHFFFAOYSA-N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 22
239000001257 hydrogen Substances 0.000 abstract description 19
239000000543 intermediate Substances 0.000 abstract description 8
208000035473 Communicable disease Diseases 0.000 abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
244000000010 microbial pathogen Species 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 540
239000000243 solution Substances 0.000 description 366
-1 3-hydroxy-3-cephem compound Chemical class 0.000 description 260
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 221
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 201
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 200
229940093499 ethyl acetate Drugs 0.000 description 180
235000019439 ethyl acetate Nutrition 0.000 description 180
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 170
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 168
239000007864 aqueous solution Substances 0.000 description 148
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 133
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 123
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 111
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 109
238000000034 method Methods 0.000 description 102
239000000203 mixture Substances 0.000 description 101
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 96
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 94
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 91
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
238000001914 filtration Methods 0.000 description 87
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 84
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 81
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 81
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
239000010410 layer Substances 0.000 description 69
230000002829 reductive effect Effects 0.000 description 69
238000006243 chemical reaction Methods 0.000 description 66
239000000725 suspension Substances 0.000 description 65
229920006395 saturated elastomer Polymers 0.000 description 62
239000002244 precipitate Substances 0.000 description 55
229910000030 sodium bicarbonate Inorganic materials 0.000 description 55
235000017557 sodium bicarbonate Nutrition 0.000 description 55
238000001816 cooling Methods 0.000 description 47
229960003390 magnesium sulfate Drugs 0.000 description 47
229910052943 magnesium sulfate Inorganic materials 0.000 description 47
235000019341 magnesium sulphate Nutrition 0.000 description 47
239000011780 sodium chloride Substances 0.000 description 45
239000000706 filtrate Substances 0.000 description 42
239000000284 extract Substances 0.000 description 40
229960004132 diethyl ether Drugs 0.000 description 38
LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 38
UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 36
239000000126 substance Substances 0.000 description 35
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 33
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 31
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 30
239000003795 chemical substances by application Substances 0.000 description 27
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 26
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000003921 oil Substances 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
238000003756 stirring Methods 0.000 description 23
239000000047 product Substances 0.000 description 21
238000012360 testing method Methods 0.000 description 21
150000002148 esters Chemical class 0.000 description 20
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
239000007858 starting material Substances 0.000 description 18
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
229910052736 halogen Inorganic materials 0.000 description 16
150000002367 halogens Chemical group 0.000 description 16
229910000027 potassium carbonate Inorganic materials 0.000 description 16
235000011181 potassium carbonates Nutrition 0.000 description 16
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 15
239000002585 base Substances 0.000 description 15
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 15
235000019253 formic acid Nutrition 0.000 description 15
MZTBTXMUURGGNR-GLGOKHISSA-N (4-nitrophenyl)methyl (6r)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1C(C(N11)=O)N)CC=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 MZTBTXMUURGGNR-GLGOKHISSA-N 0.000 description 14
229940023032 activated charcoal Drugs 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
239000000843 powder Substances 0.000 description 14
125000006239 protecting group Chemical group 0.000 description 14
NNULBSISHYWZJU-QHDYGNBISA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOC NNULBSISHYWZJU-QHDYGNBISA-N 0.000 description 13
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 13
230000007062 hydrolysis Effects 0.000 description 13
238000006460 hydrolysis reaction Methods 0.000 description 13
244000005700 microbiome Species 0.000 description 13
239000012044 organic layer Substances 0.000 description 13
235000017281 sodium acetate Nutrition 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 12
125000002252 acyl group Chemical group 0.000 description 12
230000002411 adverse Effects 0.000 description 12
239000013078 crystal Substances 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
RJFPBECTFIUTHB-INEUFUBQSA-N (6r,7r)-7-azaniumyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 RJFPBECTFIUTHB-INEUFUBQSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
229910052783 alkali metal Inorganic materials 0.000 description 11
125000003342 alkenyl group Chemical group 0.000 description 11
238000010531 catalytic reduction reaction Methods 0.000 description 11
150000002431 hydrogen Chemical group 0.000 description 11
239000000463 material Substances 0.000 description 11
238000005406 washing Methods 0.000 description 11
108090000371 Esterases Proteins 0.000 description 10
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 10
229910052799 carbon Inorganic materials 0.000 description 10
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 10
150000002443 hydroxylamines Chemical class 0.000 description 10
239000011734 sodium Substances 0.000 description 10
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000011369 resultant mixture Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
230000000845 anti-microbial effect Effects 0.000 description 8
229910001873 dinitrogen Inorganic materials 0.000 description 8
IACSYDRIOYGJNH-UHFFFAOYSA-N ethyl 2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NO)C(C)=O IACSYDRIOYGJNH-UHFFFAOYSA-N 0.000 description 8
125000005179 haloacetyl group Chemical group 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
229920005989 resin Polymers 0.000 description 8
239000011347 resin Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000001632 sodium acetate Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
125000001113 thiadiazolyl group Chemical group 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
239000004599 antimicrobial Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000001179 sorption measurement Methods 0.000 description 7
239000000758 substrate Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000003379 elimination reaction Methods 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
150000002440 hydroxy compounds Chemical class 0.000 description 6
150000007529 inorganic bases Chemical class 0.000 description 6
229960004592 isopropanol Drugs 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
229910052698 phosphorus Inorganic materials 0.000 description 6
230000001376 precipitating effect Effects 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
BKUNRIQUAJBEBD-LRTDYKAYSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC BKUNRIQUAJBEBD-LRTDYKAYSA-N 0.000 description 5
QUSLYJRJAKKYQP-XTBNCEIVSA-N (4-nitrophenyl)methyl (6r)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.S([C@@H]1C(C(N11)=O)N)CC(Cl)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QUSLYJRJAKKYQP-XTBNCEIVSA-N 0.000 description 5
ZMBSJDXRIAOGBK-JLOHTSLTSA-N (4-nitrophenyl)methyl (6r)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1C(C(N11)=O)N)CC(O)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 ZMBSJDXRIAOGBK-JLOHTSLTSA-N 0.000 description 5
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 5
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
125000005646 oximino group Chemical group 0.000 description 5
230000036961 partial effect Effects 0.000 description 5
238000000746 purification Methods 0.000 description 5
ADLFUPFRVXCDMO-GILAUPEISA-M sodium (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)[O-])C1=O)=NOC.[Na+] ADLFUPFRVXCDMO-GILAUPEISA-M 0.000 description 5
229940087562 sodium acetate trihydrate Drugs 0.000 description 5
KMAZBVUCSPNWGZ-UUSAFJCLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCC KMAZBVUCSPNWGZ-UUSAFJCLSA-N 0.000 description 4
NRRJNSWNWIDHOX-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC=O)=N1 NRRJNSWNWIDHOX-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical class CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
241000588769 Proteus <enterobacteria> Species 0.000 description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
239000006286 aqueous extract Substances 0.000 description 4
125000004181 carboxyalkyl group Chemical group 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
230000007071 enzymatic hydrolysis Effects 0.000 description 4
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
239000011259 mixed solution Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
YVJLOVBOSMIXIV-LRTDYKAYSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCC YVJLOVBOSMIXIV-LRTDYKAYSA-N 0.000 description 3
GKLDFHWFQIULNO-UUSAFJCLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-propan-2-yloxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC(C)C GKLDFHWFQIULNO-UUSAFJCLSA-N 0.000 description 3
IXPSCFXNKWWDAK-FFFFSGIJSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOC IXPSCFXNKWWDAK-FFFFSGIJSA-N 0.000 description 3
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 3
RQMBWYIXVXJFNY-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetic acid Chemical compound CCON=C(C(O)=O)C1=CSC(N)=N1 RQMBWYIXVXJFNY-UHFFFAOYSA-N 0.000 description 3
NLARCUDOUOQRPB-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CON=C(C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-UHFFFAOYSA-N 0.000 description 3
BKZUFHOOLCRIDP-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-propoxyiminoacetic acid Chemical compound CCCON=C(C(O)=O)C1=CSC(NC=O)=N1 BKZUFHOOLCRIDP-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NVIASKNPYJLAOX-UHFFFAOYSA-N 2-butoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid Chemical compound CCCCON=C(C(O)=O)C1=CSC(NC=O)=N1 NVIASKNPYJLAOX-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
241000588722 Escherichia Species 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
210000000941 bile Anatomy 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
230000008030 elimination Effects 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
235000012054 meals Nutrition 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000010998 test method Methods 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
NLARCUDOUOQRPB-WTKPLQERSA-N (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(/C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-WTKPLQERSA-N 0.000 description 2
NRRJNSWNWIDHOX-YHYXMXQVSA-N (2z)-2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(/C(O)=O)C1=CSC(NC=O)=N1 NRRJNSWNWIDHOX-YHYXMXQVSA-N 0.000 description 2
JTAINDUMZOYKLK-XCWJXAQQSA-N (4-nitrophenyl)methyl (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCC(F)(F)F JTAINDUMZOYKLK-XCWJXAQQSA-N 0.000 description 2
SNLBPEDWPGTTFV-XCWJXAQQSA-N (4-nitrophenyl)methyl (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC SNLBPEDWPGTTFV-XCWJXAQQSA-N 0.000 description 2
UXBNXBNCTUVPBH-FBLFFUNLSA-N (4-nitrophenyl)methyl (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-propoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCC UXBNXBNCTUVPBH-FBLFFUNLSA-N 0.000 description 2
FTIDUDFDYBIQGN-XCWJXAQQSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCC FTIDUDFDYBIQGN-XCWJXAQQSA-N 0.000 description 2
INLDUXWQMBSUKM-LRHAYUFXSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NO INLDUXWQMBSUKM-LRHAYUFXSA-N 0.000 description 2
SEIPWSCOQXTIGI-FBMWCMRBSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NO SEIPWSCOQXTIGI-FBMWCMRBSA-N 0.000 description 2
VLIWZMLYZSNTJX-KPMSDPLLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC VLIWZMLYZSNTJX-KPMSDPLLSA-N 0.000 description 2
UWKKCFFECKNVTD-AVKWCDSFSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCC(C)C UWKKCFFECKNVTD-AVKWCDSFSA-N 0.000 description 2
SNWXBCZBRYZWIU-LMNIDFBRSA-N (4-nitrophenyl)methyl (6R)-7-[[2-butoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCCC SNWXBCZBRYZWIU-LMNIDFBRSA-N 0.000 description 2
MTKUQZKFPBXOGL-MQNHUJCZSA-N (4-nitrophenyl)methyl (6R)-7-[[2-cyclohexyloxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC1CCCCC1 MTKUQZKFPBXOGL-MQNHUJCZSA-N 0.000 description 2
NNUHKPCYTQNEPP-KPMSDPLLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-methoxyimino-2-(thiadiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1N=NC(=C1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC NNUHKPCYTQNEPP-KPMSDPLLSA-N 0.000 description 2
QCUWDJVZLFMUIZ-ASSPZCQQSA-N (4-nitrophenyl)methyl (6r)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.S([C@@H]1C(C(N11)=O)N)CC=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QCUWDJVZLFMUIZ-ASSPZCQQSA-N 0.000 description 2
WYGLNZLCCSYHSG-LESKNEHBSA-N (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOCC(F)(F)F WYGLNZLCCSYHSG-LESKNEHBSA-N 0.000 description 2
WXLQJBRZLLFXRM-LESKNEHBSA-N (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOC WXLQJBRZLLFXRM-LESKNEHBSA-N 0.000 description 2
NPZVGBXLUQCVOS-LNUXAPHWSA-N (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-propoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOCCC NPZVGBXLUQCVOS-LNUXAPHWSA-N 0.000 description 2
MMYBPHNLUZIBCE-LESKNEHBSA-N (6R)-3-methoxy-7-[[2-methoxyimino-2-[2-[(2,2,2-trifluoroacetyl)amino]-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound FC(C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)OC)C(=O)O)C1=O)=NOC)(F)F MMYBPHNLUZIBCE-LESKNEHBSA-N 0.000 description 2
PFQZVHMDOYXFCA-GILAUPEISA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride Chemical compound Cl.CON=C(C(=O)NC1[C@H]2SCC=C(N2C1=O)C(O)=O)c1csc(N)n1 PFQZVHMDOYXFCA-GILAUPEISA-N 0.000 description 2
JDNFICRTIJHEOM-KPMSDPLLSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-octoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCCCCCCCC JDNFICRTIJHEOM-KPMSDPLLSA-N 0.000 description 2
XATQPFJEZUEIRI-WPZCJLIBSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-pentoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCCCCC XATQPFJEZUEIRI-WPZCJLIBSA-N 0.000 description 2
VIPDIJBYRQZXIE-WPZCJLIBSA-N (6R)-7-[[2-(2-ethoxy-2-oxoethoxy)imino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(=O)OCC VIPDIJBYRQZXIE-WPZCJLIBSA-N 0.000 description 2
SKWPZKHCDIORLU-FQNRMIAFSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-pentoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCCCCC SKWPZKHCDIORLU-FQNRMIAFSA-N 0.000 description 2
ZMEZBWBWNZVEOP-JLOHTSLTSA-N (6R)-7-[[2-(carboxymethoxyimino)-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(=O)O ZMEZBWBWNZVEOP-JLOHTSLTSA-N 0.000 description 2
XNQZTBXJQSGRRD-PVQCJRHBSA-N (6R)-7-[[2-butoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)OC)C(=O)O)C1=O)=NOCCCC XNQZTBXJQSGRRD-PVQCJRHBSA-N 0.000 description 2
NOBVVIHMEGNGSC-FBMWCMRBSA-N (6R)-7-[[2-cyclohexyloxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOC1CCCCC1 NOBVVIHMEGNGSC-FBMWCMRBSA-N 0.000 description 2
UVJAWYKDJJXIMZ-BAFYGKSASA-N (6r)-3-hydroxy-5-thia-1-azabicyclo[4.2.0]octan-8-one Chemical compound C1C(O)CS[C@@H]2CC(=O)N21 UVJAWYKDJJXIMZ-BAFYGKSASA-N 0.000 description 2
NNULBSISHYWZJU-JHKIXPBQSA-N (6r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]12)CC=C(C(O)=O)N1C(=O)C2NC(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-JHKIXPBQSA-N 0.000 description 2
VYMQVMHQTNMGLR-JLOHTSLTSA-N (6r)-7-amino-3-(4-methylphenyl)sulfonyloxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 VYMQVMHQTNMGLR-JLOHTSLTSA-N 0.000 description 2
125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 2
MZXRHHRUCKPYDE-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-propan-2-yloxyiminoacetic acid Chemical compound CC(C)ON=C(C(O)=O)C1=CSC(N)=N1 MZXRHHRUCKPYDE-UHFFFAOYSA-N 0.000 description 2
MXEBBKNMRBMCSW-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetic acid Chemical compound CCCON=C(C(O)=O)C1=CSC(N)=N1 MXEBBKNMRBMCSW-UHFFFAOYSA-N 0.000 description 2
VGOYZRAMGMTTOP-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetic acid Chemical compound CC(C)(C)OC(=O)CON=C(C(O)=O)C1=CSC(NC=O)=N1 VGOYZRAMGMTTOP-UHFFFAOYSA-N 0.000 description 2
CCSBTUBILLOLHE-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl chloride Chemical compound CON=C(C(Cl)=O)C1=CSC(NC=O)=N1 CCSBTUBILLOLHE-UHFFFAOYSA-N 0.000 description 2
WZPOBANFTJLEHD-UHFFFAOYSA-N 2-ethoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid Chemical compound CCON=C(C(O)=O)C1=CSC(NC=O)=N1 WZPOBANFTJLEHD-UHFFFAOYSA-N 0.000 description 2
MDEKEOFWAHRGNU-UHFFFAOYSA-N 2-methoxyimino-2-[2-[(2,2,2-trifluoroacetyl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC(=O)C(F)(F)F)=N1 MDEKEOFWAHRGNU-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
BGLAMXJBTZOWLK-UHFFFAOYSA-N 3-[[4-acetyl-2,3,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-4-hydroxy-5,6-dimethylpyran-2-one Chemical compound OC1=C(C(C)=O)C(CC=C(C)C)=C(O)C(CC=2C(OC(C)=C(C)C=2O)=O)=C1O BGLAMXJBTZOWLK-UHFFFAOYSA-N 0.000 description 2
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 2
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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 2
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
241000589565 Flavobacterium Species 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000588748 Klebsiella Species 0.000 description 2
241000191953 Kocuria varians Species 0.000 description 2
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 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001467578 Microbacterium Species 0.000 description 2
241000219470 Mirabilis Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
230000006181 N-acylation Effects 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
241000586779 Protaminobacter Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
241000589180 Rhizobium Species 0.000 description 2
241000158504 Rhodococcus hoagii Species 0.000 description 2
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
241000607720 Serratia Species 0.000 description 2
241000191940 Staphylococcus Species 0.000 description 2
241000191963 Staphylococcus epidermidis Species 0.000 description 2
241000607598 Vibrio Species 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000001118 alkylidene group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000001483 arginine derivatives Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
229940077388 benzenesulfonate Drugs 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000001311 chemical methods and process Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
150000002085 enols Chemical class 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
MYCKHVUASDZSES-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-butoxyiminoacetate Chemical compound CCCCON=C(C(=O)OCC)C1=CSC(N)=N1 MYCKHVUASDZSES-UHFFFAOYSA-N 0.000 description 2
BOIAXGZMWDGXGJ-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-cyclohexyloxyiminoacetate Chemical compound C=1SC(N)=NC=1C(C(=O)OCC)=NOC1CCCCC1 BOIAXGZMWDGXGJ-UHFFFAOYSA-N 0.000 description 2
PBTDPDPSMUNSNY-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-octoxyiminoacetate Chemical compound CCCCCCCCON=C(C(=O)OCC)C1=CSC(N)=N1 PBTDPDPSMUNSNY-UHFFFAOYSA-N 0.000 description 2
WEDOYODBYFGEFJ-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-pentoxyiminoacetate Chemical compound CCCCCON=C(C(=O)OCC)C1=CSC(N)=N1 WEDOYODBYFGEFJ-UHFFFAOYSA-N 0.000 description 2
PUZXQANZDPQRRJ-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-prop-2-enoxyiminoacetate Chemical compound C=CCON=C(C(=O)OCC)C1=CSC(N)=N1 PUZXQANZDPQRRJ-UHFFFAOYSA-N 0.000 description 2
IBBFCLMPRISSNU-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetate Chemical compound C#CCON=C(C(=O)OCC)C1=CSC(N)=N1 IBBFCLMPRISSNU-UHFFFAOYSA-N 0.000 description 2
HAMGKLYOJWNGII-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetate Chemical compound CCCON=C(C(=O)OCC)C1=CSC(N)=N1 HAMGKLYOJWNGII-UHFFFAOYSA-N 0.000 description 2
PJWCIBFNPRMDNP-UHFFFAOYSA-N ethyl 2-(2-chloroethoxyimino)-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOCCCl PJWCIBFNPRMDNP-UHFFFAOYSA-N 0.000 description 2
JUGFLYSTUIIKNZ-UHFFFAOYSA-N ethyl 2-butoxyimino-3-oxobutanoate Chemical compound CCCCON=C(C(C)=O)C(=O)OCC JUGFLYSTUIIKNZ-UHFFFAOYSA-N 0.000 description 2
LVUXYNYWXQROJH-UHFFFAOYSA-N ethyl 2-butoxyimino-4-chloro-3-oxobutanoate Chemical compound CCCCON=C(C(=O)CCl)C(=O)OCC LVUXYNYWXQROJH-UHFFFAOYSA-N 0.000 description 2
UGHBGWAJKLJSLP-UHFFFAOYSA-N ethyl 2-cyclohexyloxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOC1CCCCC1 UGHBGWAJKLJSLP-UHFFFAOYSA-N 0.000 description 2
HWGBFHADJQHTOG-UHFFFAOYSA-N ethyl 2-methoxyimino-2-(thiadiazol-4-yl)acetate Chemical compound CCOC(=O)C(=NOC)C1=CSN=N1 HWGBFHADJQHTOG-UHFFFAOYSA-N 0.000 description 2
ZWDVSWNQKQHHMT-UHFFFAOYSA-N ethyl 2-methoxyimino-3-[(2-methylpropan-2-yl)oxycarbonylhydrazinylidene]butanoate Chemical compound CCOC(=O)C(=NOC)C(C)=NNC(=O)OC(C)(C)C ZWDVSWNQKQHHMT-UHFFFAOYSA-N 0.000 description 2
HASOOENYFDJEAK-UHFFFAOYSA-N ethyl 2-methoxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOC HASOOENYFDJEAK-UHFFFAOYSA-N 0.000 description 2
YTCSCPYCWAGPGA-UHFFFAOYSA-N ethyl 2-prop-2-enoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate Chemical compound C=CCON=C(C(=O)OCC)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 YTCSCPYCWAGPGA-UHFFFAOYSA-N 0.000 description 2
NPXGGKSJMGCVLL-UHFFFAOYSA-N ethyl 2-prop-2-ynoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate Chemical compound C#CCON=C(C(=O)OCC)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 NPXGGKSJMGCVLL-UHFFFAOYSA-N 0.000 description 2
BRLUUTKDSNDBBZ-UHFFFAOYSA-N ethyl 3-oxo-2-pentoxyiminobutanoate Chemical compound CCCCCON=C(C(C)=O)C(=O)OCC BRLUUTKDSNDBBZ-UHFFFAOYSA-N 0.000 description 2
XWFABJJRNZCSPV-UHFFFAOYSA-N ethyl 3-oxo-2-propoxyiminobutanoate Chemical compound CCCON=C(C(C)=O)C(=O)OCC XWFABJJRNZCSPV-UHFFFAOYSA-N 0.000 description 2
OTVKRRYPMMESRP-UHFFFAOYSA-N ethyl 4-chloro-2-(2-chloroethoxyimino)-3-oxobutanoate Chemical compound CCOC(=O)C(C(=O)CCl)=NOCCCl OTVKRRYPMMESRP-UHFFFAOYSA-N 0.000 description 2
OTCCCOMISIFTHS-UHFFFAOYSA-N ethyl 4-chloro-2-(2-methylpropoxyimino)-3-oxobutanoate Chemical compound CCOC(=O)C(C(=O)CCl)=NOCC(C)C OTCCCOMISIFTHS-UHFFFAOYSA-N 0.000 description 2
DRXTXKHMCOSBBS-UHFFFAOYSA-N ethyl 4-chloro-2-cyclohexyloxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(C(=O)CCl)=NOC1CCCCC1 DRXTXKHMCOSBBS-UHFFFAOYSA-N 0.000 description 2
QQTHNMBPRSXIHX-UHFFFAOYSA-N ethyl 4-chloro-2-methoxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NOC)C(=O)CCl QQTHNMBPRSXIHX-UHFFFAOYSA-N 0.000 description 2
WCOFSVDTINLPQP-UHFFFAOYSA-N ethyl 4-chloro-2-octoxyimino-3-oxobutanoate Chemical compound CCCCCCCCON=C(C(=O)CCl)C(=O)OCC WCOFSVDTINLPQP-UHFFFAOYSA-N 0.000 description 2
KFZUIHBXFDORAU-UHFFFAOYSA-N ethyl 4-chloro-3-oxo-2-pentoxyiminobutanoate Chemical compound CCCCCON=C(C(=O)CCl)C(=O)OCC KFZUIHBXFDORAU-UHFFFAOYSA-N 0.000 description 2
IWXNQTNNPFDHKR-UHFFFAOYSA-N ethyl 4-chloro-3-oxo-2-prop-2-ynoxyiminobutanoate Chemical compound CCOC(=O)C(C(=O)CCl)=NOCC#C IWXNQTNNPFDHKR-UHFFFAOYSA-N 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
239000001095 magnesium carbonate Substances 0.000 description 2
229910000021 magnesium carbonate Inorganic materials 0.000 description 2
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
239000000347 magnesium hydroxide Substances 0.000 description 2
229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229940091250 magnesium supplement Drugs 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910000000 metal hydroxide Inorganic materials 0.000 description 2
150000004692 metal hydroxides Chemical class 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
238000007034 nitrosation reaction Methods 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 2
239000001205 polyphosphate Substances 0.000 description 2
235000011176 polyphosphates Nutrition 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
238000011084 recovery Methods 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
IFHUYJAXVZEGRA-WAHCDEBTSA-M sodium (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate dihydrate Chemical compound O.O.[Na+].CON=C(C(=O)NC1[C@H]2SCC=C(N2C1=O)C([O-])=O)c1csc(N)n1 IFHUYJAXVZEGRA-WAHCDEBTSA-M 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000002769 thiazolinyl group Chemical group 0.000 description 2
230000001131 transforming effect Effects 0.000 description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
229940086542 triethylamine Drugs 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
108010050327 trypticase-soy broth Proteins 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
229920001567 vinyl ester resin Polymers 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 1
YWIGTPFREAKXAR-PIFIWZBESA-N (4-nitrophenyl)methyl (6R)-3-chloro-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-hexoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCCCCC YWIGTPFREAKXAR-PIFIWZBESA-N 0.000 description 1
DLWFYAFPFDKVEH-FBLFFUNLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetyl]amino]-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCC(C)C DLWFYAFPFDKVEH-FBLFFUNLSA-N 0.000 description 1
BUQNACFZUGMTKL-XCWJXAQQSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOC BUQNACFZUGMTKL-XCWJXAQQSA-N 0.000 description 1
WGJWTDKQDYAQPQ-CSDJQUKGSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate Chemical compound S([C@@H]1C(C(N11)=O)NC(=O)C(=NOC)C=2N=C(NC=O)SC=2)CC(O)C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 WGJWTDKQDYAQPQ-CSDJQUKGSA-N 0.000 description 1
ZHHYAFRQMPQKLD-GWQXNCQPSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-pentoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCCCC ZHHYAFRQMPQKLD-GWQXNCQPSA-N 0.000 description 1
ZRJBXWLHTJDUKO-FBLFFUNLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetyl]amino]-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCC#C ZRJBXWLHTJDUKO-FBLFFUNLSA-N 0.000 description 1
YNYPJXLJBVDHCY-FBLFFUNLSA-N (4-nitrophenyl)methyl (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-propoxyiminoacetyl]amino]-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCC YNYPJXLJBVDHCY-FBLFFUNLSA-N 0.000 description 1
OWFFXXLQLZYNFE-LEQGEALCSA-N (4-nitrophenyl)methyl (6R)-7-[[2-butoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)OC)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCCC OWFFXXLQLZYNFE-LEQGEALCSA-N 0.000 description 1
KHEUIFIYOIUSQL-AVKWCDSFSA-N (4-nitrophenyl)methyl (6R)-7-[[2-butoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NOCCCC KHEUIFIYOIUSQL-AVKWCDSFSA-N 0.000 description 1
AJAYYHYWTPEASL-BDPMCISCSA-N (4-nitrophenyl)methyl (6r)-3-hydroxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)O)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)CC1=CC=CC=C1 AJAYYHYWTPEASL-BDPMCISCSA-N 0.000 description 1
NJIRVDUDJYFGCB-OMOCHNIRSA-N (4-nitrophenyl)methyl (6r)-7-[(4-bromo-3-oxobutanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1=CCS[C@H]2N1C(=O)C2NC(=O)CC(=O)CBr NJIRVDUDJYFGCB-OMOCHNIRSA-N 0.000 description 1
UIVDEOFIOHEVLM-RVFDVJBWSA-N (4-nitrophenyl)methyl (6r)-7-amino-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.S([C@H]1N2C(C1N)=O)CC(OC)=C2C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 UIVDEOFIOHEVLM-RVFDVJBWSA-N 0.000 description 1
RNKOFZXWWQEQJY-VGAJERRHSA-N (4-nitrophenyl)methyl (6r)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1=CCS[C@H]2N1C(=O)C2NC(=O)CC1=CC=CC=C1 RNKOFZXWWQEQJY-VGAJERRHSA-N 0.000 description 1
YLIOIMWNSIRKDG-ZWNOBZJWSA-N (4-nitrophenyl)methyl (6r,7r)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1[C@@H](C(N11)=O)N)CC(Cl)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 YLIOIMWNSIRKDG-ZWNOBZJWSA-N 0.000 description 1
QUSLYJRJAKKYQP-HTMVYDOJSA-N (4-nitrophenyl)methyl (6r,7r)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.S([C@@H]1[C@@H](C(N11)=O)N)CC(Cl)=C1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QUSLYJRJAKKYQP-HTMVYDOJSA-N 0.000 description 1
UMVFZVVLGJMLQT-QHDYGNBISA-N (6R)-7-[(4-bromo-2-methoxyimino-3-oxobutanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)C(CBr)=O UMVFZVVLGJMLQT-QHDYGNBISA-N 0.000 description 1
LBXLDJXMTZZRKA-PLNQYNMKSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOCC(F)(F)F LBXLDJXMTZZRKA-PLNQYNMKSA-N 0.000 description 1
BRBSPXLDZLWNHO-QHDYGNBISA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(F)(F)F BRBSPXLDZLWNHO-QHDYGNBISA-N 0.000 description 1
IUTZHLZTHRLPMX-WCRCJTMVSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2,3,3-trifluoroprop-2-enoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(=C(F)F)F IUTZHLZTHRLPMX-WCRCJTMVSA-N 0.000 description 1
CGPLYMUYBCGVDU-SBXXRYSUSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2-ethoxy-2-oxoethoxy)iminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(=O)OCC CGPLYMUYBCGVDU-SBXXRYSUSA-N 0.000 description 1
KBJBTSQABNHGIP-SBXXRYSUSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(C)C KBJBTSQABNHGIP-SBXXRYSUSA-N 0.000 description 1
MSCHWTRLKGAEQT-FFFFSGIJSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(=O)O MSCHWTRLKGAEQT-FFFFSGIJSA-N 0.000 description 1
DCZZTKNUTOESDR-JOPIAHFSSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-butoxyiminoacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)OC)C(=O)O)C1=O)=NOCCCC DCZZTKNUTOESDR-JOPIAHFSSA-N 0.000 description 1
UAEALFDEWLJRBM-FQNRMIAFSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-cyclohexyloxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOC1CCCCC1 UAEALFDEWLJRBM-FQNRMIAFSA-N 0.000 description 1
NIMUQMXPKREWER-LESKNEHBSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOCC NIMUQMXPKREWER-LESKNEHBSA-N 0.000 description 1
QRGJJTYSPCXVCW-OMNKOJBGSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NO QRGJJTYSPCXVCW-OMNKOJBGSA-N 0.000 description 1
YRIZWEOUOCHLOT-BUDIUTNSSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3,4-dimethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(C(S2)C)C)C(=O)O)C1=O)=NOC YRIZWEOUOCHLOT-BUDIUTNSSA-N 0.000 description 1
OIBNNEXVUACCKV-HYEBNMQDSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride Chemical compound Cl.CON=C(C(=O)NC1[C@H]2SCC(Cl)=C(N2C1=O)C(O)=O)c1csc(N)n1 OIBNNEXVUACCKV-HYEBNMQDSA-N 0.000 description 1
JETIJFQWDMHVOR-LESKNEHBSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)OC)C(=O)O)C1=O)=NOC JETIJFQWDMHVOR-LESKNEHBSA-N 0.000 description 1
NPOCYCRIDGSDDG-WCRCJTMVSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOCC#C NPOCYCRIDGSDDG-WCRCJTMVSA-N 0.000 description 1
WOWORTQLYPRIFP-LNUXAPHWSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)OC)C(=O)O)C1=O)=NOCC#C WOWORTQLYPRIFP-LNUXAPHWSA-N 0.000 description 1
JVPITNRCLMGFOM-JLOHTSLTSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC#C JVPITNRCLMGFOM-JLOHTSLTSA-N 0.000 description 1
YGPSPDMXNBPOQU-JLOHTSLTSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-propan-2-yloxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOC(C)C YGPSPDMXNBPOQU-JLOHTSLTSA-N 0.000 description 1
REWCDMVQQUOGNE-WCRCJTMVSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O)=NOCCC REWCDMVQQUOGNE-WCRCJTMVSA-N 0.000 description 1
QMDBRAXQDPPHFM-JLOHTSLTSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCCC QMDBRAXQDPPHFM-JLOHTSLTSA-N 0.000 description 1
QBOYGKXIKXTULV-JLOHTSLTSA-N (6R)-7-[[2-(2-chloroethoxyimino)-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCCCl QBOYGKXIKXTULV-JLOHTSLTSA-N 0.000 description 1
BTYBYONWHHNTCH-FFFFSGIJSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(F)(F)F BTYBYONWHHNTCH-FFFFSGIJSA-N 0.000 description 1
BBGMLGLPHJMCJX-WPZCJLIBSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(C)C BBGMLGLPHJMCJX-WPZCJLIBSA-N 0.000 description 1
DXINFRJYVWAVKS-FQNRMIAFSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCC(=O)OC(C)(C)C DXINFRJYVWAVKS-FQNRMIAFSA-N 0.000 description 1
CAXRMRCVLDIJMD-KASCWWPPSA-N (6R)-7-[[2-[2-(2-formamido-1,3-thiazol-4-yl)octan-4-yloxyimino]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C)CC(CCCC)ON=CC(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O CAXRMRCVLDIJMD-KASCWWPPSA-N 0.000 description 1
MXYDRCOUCXEGFK-WPZCJLIBSA-N (6R)-7-[[2-butoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOCCCC MXYDRCOUCXEGFK-WPZCJLIBSA-N 0.000 description 1
VOZXYFWLFGQTDB-QHDYGNBISA-N (6R)-7-[[2-methoxyimino-2-(thiadiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1N=NC(=C1)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)O)C1=O)=NOC VOZXYFWLFGQTDB-QHDYGNBISA-N 0.000 description 1
YURSOQRGSZKXCK-BDPMCISCSA-N (6r)-3-(4-methylphenyl)sulfonyloxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=C(C(O)=O)N2C(=O)C(NC(=O)CC=3C=CC=CC=3)[C@H]2SC1 YURSOQRGSZKXCK-BDPMCISCSA-N 0.000 description 1
HSBGNRBPSORKFQ-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]octane-3,8-dione Chemical compound S1CC(=O)CN2C(=O)C[C@H]21 HSBGNRBPSORKFQ-ZCFIWIBFSA-N 0.000 description 1
NPYXGSRSTRAOBT-LHIURRSHSA-N (6r)-7-[(4-bromo-3-oxobutanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2C(NC(=O)CC(=O)CBr)C(=O)N12 NPYXGSRSTRAOBT-LHIURRSHSA-N 0.000 description 1
ASLZBQCVFWAXTG-MPKXYMLHSA-N (6r)-7-amino-3,4-dimethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(C)C(C)S[C@@H]2C(N)C(=O)N21 ASLZBQCVFWAXTG-MPKXYMLHSA-N 0.000 description 1
OQSAFIZCBAZPMY-PUOGSPQQSA-N (6r)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(Cl)=C(C(O)=O)N2C(=O)C(N)[C@H]21 OQSAFIZCBAZPMY-PUOGSPQQSA-N 0.000 description 1
WAQKVEYMZFUOAH-FHJBIJLDSA-N (6r)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride Chemical compound Cl.S1CC(Cl)=C(C(O)=O)N2C(=O)C(N)[C@H]21 WAQKVEYMZFUOAH-FHJBIJLDSA-N 0.000 description 1
FHJRYYNOYUHGNP-GUNDQUCTSA-N (6r)-7-amino-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride Chemical compound Cl.S1CC(OC)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 FHJRYYNOYUHGNP-GUNDQUCTSA-N 0.000 description 1
QITDACOZCQXYQY-BAFYGKSASA-N (6r)-7-amino-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C(N)[C@H]21 QITDACOZCQXYQY-BAFYGKSASA-N 0.000 description 1
XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 1
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
MLAFRLBDNVSLPE-UHFFFAOYSA-N 1-hydroxyethyl acetate Chemical compound CC(O)OC(C)=O MLAFRLBDNVSLPE-UHFFFAOYSA-N 0.000 description 1
VRTBBGYZDDZSCW-UHFFFAOYSA-N 1-hydroxyethyl butanoate Chemical compound CCCC(=O)OC(C)O VRTBBGYZDDZSCW-UHFFFAOYSA-N 0.000 description 1
KGZREBGSQBOEQE-UHFFFAOYSA-N 1-hydroxyethyl propanoate Chemical compound CCC(=O)OC(C)O KGZREBGSQBOEQE-UHFFFAOYSA-N 0.000 description 1
BVABBPZOMBGJEV-UHFFFAOYSA-N 1-hydroxyhexyl hexanoate Chemical compound CCCCCC(O)OC(=O)CCCCC BVABBPZOMBGJEV-UHFFFAOYSA-N 0.000 description 1
VEGXEWGKYMMJKP-UHFFFAOYSA-N 1-hydroxypropyl acetate Chemical compound CCC(O)OC(C)=O VEGXEWGKYMMJKP-UHFFFAOYSA-N 0.000 description 1
AUCNXTXSMQPPMK-UHFFFAOYSA-N 1-hydroxypropyl hexanoate Chemical compound CCCCCC(=O)OC(O)CC AUCNXTXSMQPPMK-UHFFFAOYSA-N 0.000 description 1
UTJLIFNVEXVSDN-UHFFFAOYSA-N 1-hydroxypropyl propanoate Chemical compound CCC(O)OC(=O)CC UTJLIFNVEXVSDN-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
CGFUMGTXPMJLCJ-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-prop-2-ynoxyiminoacetic acid Chemical compound C#CCON=C(C(=O)O)C1=CSC(NC=O)=N1 CGFUMGTXPMJLCJ-UHFFFAOYSA-N 0.000 description 1
JEZNNIFNTWWAPU-UHFFFAOYSA-N 2-(2-methylpropoxyimino)-3-oxobutanoic acid Chemical compound CC(C)CON=C(C(C)=O)C(O)=O JEZNNIFNTWWAPU-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
ODXCMWLJDMOSSL-UHFFFAOYSA-N 2-ethyl-1,2-benzoxazol-2-ium Chemical class C1=CC=C2O[N+](CC)=CC2=C1 ODXCMWLJDMOSSL-UHFFFAOYSA-N 0.000 description 1
NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
UDFHIMFWMIISIQ-UHFFFAOYSA-N 2-methoxyimino-2-(thiadiazol-4-yl)acetic acid Chemical compound CON=C(C(O)=O)C1=CSN=N1 UDFHIMFWMIISIQ-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
MWOOKDULMBMMPN-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonate Chemical compound O1[N+](CC)=CC=C1C1=CC=CC(S([O-])(=O)=O)=C1 MWOOKDULMBMMPN-UHFFFAOYSA-N 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 1
XBOVFBSAQBPGDG-UHFFFAOYSA-N 3-oxo-2-propoxyiminobutanoic acid Chemical compound CCCON=C(C(C)=O)C(O)=O XBOVFBSAQBPGDG-UHFFFAOYSA-N 0.000 description 1
IGIJSFNBEUBMGB-UHFFFAOYSA-N 4-(cyclohexyliminomethylideneamino)-n,n-diethylcyclohexan-1-amine Chemical compound C1CC(N(CC)CC)CCC1N=C=NC1CCCCC1 IGIJSFNBEUBMGB-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 1
TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000588986 Alcaligenes Species 0.000 description 1
241000588813 Alcaligenes faecalis Species 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000186063 Arthrobacter Species 0.000 description 1
241000589151 Azotobacter Species 0.000 description 1
241000589149 Azotobacter vinelandii Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000920701 Batillus Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
YDUPGCJUWJBTJS-FBMWCMRBSA-N BrCC(=O)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NO Chemical compound BrCC(=O)C(C(=O)NC1[C@@H]2N(C(=CCS2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O)=NO YDUPGCJUWJBTJS-FBMWCMRBSA-N 0.000 description 1
241000186146 Brevibacterium Species 0.000 description 1
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000861718 Chloris <Aves> Species 0.000 description 1
241001453268 Comamonas terrigena Species 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
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 1
108010068370 Glutens Proteins 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
241000588752 Kluyvera Species 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241000193386 Lysinibacillus sphaericus Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241001006344 Microbacterium flavum Species 0.000 description 1
241000192041 Micrococcus Species 0.000 description 1
241000191938 Micrococcus luteus Species 0.000 description 1
241001024304 Mino Species 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
239000004157 Nitrosyl chloride Substances 0.000 description 1
230000006179 O-acylation Effects 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
241000203720 Pimelobacter simplex Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000192023 Sarcina Species 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241000589634 Xanthomonas Species 0.000 description 1
AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
CDZHZLQKNAKKEC-UHFFFAOYSA-N [bis(hydroxymethylamino)methylamino]methanol Chemical class OCNC(NCO)NCO CDZHZLQKNAKKEC-UHFFFAOYSA-N 0.000 description 1
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229940005347 alcaligenes faecalis Drugs 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
150000001509 aspartic acid derivatives Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical class C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
IBETYBCRVYRTLY-UHFFFAOYSA-N bis(2-methoxyphenyl)methanol Chemical compound COC1=CC=CC=C1C(O)C1=CC=CC=C1OC IBETYBCRVYRTLY-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
SEANWWIVRHMMMF-UHFFFAOYSA-N butoxy(dichloro)borane Chemical compound CCCCOB(Cl)Cl SEANWWIVRHMMMF-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UYNJLEZQNMHIBB-VTELYTRQSA-L calcium (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Ca++].CON=C(C(=O)NC1[C@H]2SCC=C(N2C1=O)C([O-])=O)c1csc(N)n1.CON=C(C(=O)NC1[C@H]2SCC=C(N2C1=O)C([O-])=O)c1csc(N)n1 UYNJLEZQNMHIBB-VTELYTRQSA-L 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
108010079058 casein hydrolysate Proteins 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000012258 culturing Methods 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
TVMUHOAONWHJBV-UHFFFAOYSA-N dehydroglycine Chemical compound OC(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-N 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
SDJKREQSNPYHJT-UHFFFAOYSA-N dibromo(phenyl)phosphane Chemical compound BrP(Br)C1=CC=CC=C1 SDJKREQSNPYHJT-UHFFFAOYSA-N 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
KLGVOTHZQJDISA-JYRVWZFOSA-N ethyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-propan-2-yloxyiminoacetate Chemical compound CCOC(=O)C(=N/OC(C)C)\C1=CSC(N)=N1 KLGVOTHZQJDISA-JYRVWZFOSA-N 0.000 description 1
AMNKNFSQSCSJND-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-(2-chloroethoxyimino)acetate Chemical compound ClCCON=C(C(=O)OCC)C1=CSC(N)=N1 AMNKNFSQSCSJND-UHFFFAOYSA-N 0.000 description 1
FPMTWGVYYTUCDK-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-(2-methylpropoxyimino)acetate Chemical compound CC(C)CON=C(C(=O)OCC)C1=CSC(N)=N1 FPMTWGVYYTUCDK-UHFFFAOYSA-N 0.000 description 1
IXMJTVHPVCGNHC-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-hexoxyiminoacetate Chemical compound CCCCCCON=C(C(=O)OCC)C1=CSC(N)=N1 IXMJTVHPVCGNHC-UHFFFAOYSA-N 0.000 description 1
POBMBNPEUPDXRS-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOC(=O)C(=NOC)C1=CSC(N)=N1 POBMBNPEUPDXRS-UHFFFAOYSA-N 0.000 description 1
KLGVOTHZQJDISA-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-propan-2-yloxyiminoacetate Chemical compound CCOC(=O)C(=NOC(C)C)C1=CSC(N)=N1 KLGVOTHZQJDISA-UHFFFAOYSA-N 0.000 description 1
BSPASHUWADVGCC-UHFFFAOYSA-N ethyl 2-(2-methylpropoxyimino)-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOCC(C)C BSPASHUWADVGCC-UHFFFAOYSA-N 0.000 description 1
IKCYQNSSQXAQHC-UHFFFAOYSA-N ethyl 2-aminooxyacetate;hydrochloride Chemical compound Cl.CCOC(=O)CON IKCYQNSSQXAQHC-UHFFFAOYSA-N 0.000 description 1
KKFBLNMRJSAFAA-UHFFFAOYSA-N ethyl 2-hydroxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=NO)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 KKFBLNMRJSAFAA-UHFFFAOYSA-N 0.000 description 1
XRZGGOYAXUFFBW-UHFFFAOYSA-N ethyl 2-octoxyimino-3-oxobutanoate Chemical compound CCCCCCCCON=C(C(C)=O)C(=O)OCC XRZGGOYAXUFFBW-UHFFFAOYSA-N 0.000 description 1
JNVCJNNZBBWSSZ-UHFFFAOYSA-N ethyl 3-oxo-2-prop-2-ynoxyiminobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOCC#C JNVCJNNZBBWSSZ-UHFFFAOYSA-N 0.000 description 1
JQZYTHDHNWNPHI-UHFFFAOYSA-N ethyl 3-oxo-2-propan-2-yloxyiminobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOC(C)C JQZYTHDHNWNPHI-UHFFFAOYSA-N 0.000 description 1
HHHLOEDVDMEWKH-UHFFFAOYSA-N ethyl 4-chloro-2-ethoxyimino-3-oxobutanoate Chemical compound CCON=C(C(=O)CCl)C(=O)OCC HHHLOEDVDMEWKH-UHFFFAOYSA-N 0.000 description 1
ZXXWBULXKDPYBM-UHFFFAOYSA-N ethyl 4-chloro-3-oxo-2-propan-2-yloxyiminobutanoate Chemical compound CCOC(=O)C(C(=O)CCl)=NOC(C)C ZXXWBULXKDPYBM-UHFFFAOYSA-N 0.000 description 1
IMEHCGJFYQOSAS-UHFFFAOYSA-N ethyl 4-chloro-3-oxo-2-propoxyiminobutanoate Chemical compound CCCON=C(C(=O)CCl)C(=O)OCC IMEHCGJFYQOSAS-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
MFFXVVHUKRKXCI-UHFFFAOYSA-N ethyl iodoacetate Chemical compound CCOC(=O)CI MFFXVVHUKRKXCI-UHFFFAOYSA-N 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000021312 gluten Nutrition 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
CORAYEWGXZHKJP-WKGHQIHJSA-N hexanoyloxymethyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-chloro-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2=O)Cl)C(=O)OCOC(CCCCC)=O)C1=O)=NOC CORAYEWGXZHKJP-WKGHQIHJSA-N 0.000 description 1
UGIHYCYQGSCCAL-XPKAQORNSA-N hexanoyloxymethyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)OCOC(CCCCC)=O)C1=O)=NOC UGIHYCYQGSCCAL-XPKAQORNSA-N 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
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 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
JYVNDCLJHKQUHE-UHFFFAOYSA-N hydroxymethyl acetate Chemical compound CC(=O)OCO JYVNDCLJHKQUHE-UHFFFAOYSA-N 0.000 description 1
ZFAVADMJZHASIM-UHFFFAOYSA-N hydroxymethyl butanoate Chemical compound CCCC(=O)OCO ZFAVADMJZHASIM-UHFFFAOYSA-N 0.000 description 1
DJNFBEQKSSQEQF-UHFFFAOYSA-N hydroxymethyl hexanoate Chemical compound CCCCCC(=O)OCO DJNFBEQKSSQEQF-UHFFFAOYSA-N 0.000 description 1
XBVIHALCIHIXRI-UHFFFAOYSA-N hydroxymethyl pentanoate Chemical compound CCCCC(=O)OCO XBVIHALCIHIXRI-UHFFFAOYSA-N 0.000 description 1
NRXWLSVRXIGSKH-UHFFFAOYSA-N hydroxymethyl propanoate Chemical compound CCC(=O)OCO NRXWLSVRXIGSKH-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000001965 increasing effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
IFZADQLLMDQVOK-UHFFFAOYSA-N iodomethyl hexanoate Chemical compound CCCCCC(=O)OCI IFZADQLLMDQVOK-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229960005337 lysine hydrochloride Drugs 0.000 description 1
RAPZNDIXKANUFT-VTELYTRQSA-L magnesium (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Mg++].CON=C(C(=O)NC1[C@H]2SCC=C(N2C1=O)C([O-])=O)c1csc(N)n1.CON=C(C(=O)NC1[C@H]2SCC=C(N2C1=O)C([O-])=O)c1csc(N)n1 RAPZNDIXKANUFT-VTELYTRQSA-L 0.000 description 1
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
239000004137 magnesium phosphate Substances 0.000 description 1
229910000157 magnesium phosphate Inorganic materials 0.000 description 1
229960002261 magnesium phosphate Drugs 0.000 description 1
235000010994 magnesium phosphates Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
BHQIGUWUNPQBJY-UHFFFAOYSA-N n-diazomethanesulfonamide Chemical compound CS(=O)(=O)N=[N+]=[N-] BHQIGUWUNPQBJY-UHFFFAOYSA-N 0.000 description 1
KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
BMNDJWSIKZECMH-UHFFFAOYSA-N nitrosyl bromide Chemical compound BrN=O BMNDJWSIKZECMH-UHFFFAOYSA-N 0.000 description 1
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
235000019392 nitrosyl chloride Nutrition 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
MIQJCHKNVAHUGJ-UHFFFAOYSA-N o-(2,2,2-trifluoroethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC(F)(F)F MIQJCHKNVAHUGJ-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002674 ointment Substances 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
229940100595 phenylacetaldehyde Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
108700029318 rat female Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical class OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
AZMGUEFIPPXHET-QFBOXNNLSA-M sodium (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)[O-])C1=O)=NOCC.[Na+] AZMGUEFIPPXHET-QFBOXNNLSA-M 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
ADLFUPFRVXCDMO-PWXKCYLJSA-M sodium;(6r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]12)CC=C(C([O-])=O)N1C(=O)C2NC(=O)\C(=N/OC)C1=CSC(N)=N1 ADLFUPFRVXCDMO-PWXKCYLJSA-M 0.000 description 1
CBUBVNGXIHQZSI-YXWLHULHSA-M sodium;(6r)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate Chemical compound [Na+].S([C@@H]12)CC(O)C(C([O-])=O)N1C(=O)C2NC(=O)C(=NOC)C1=CSC(NC=O)=N1 CBUBVNGXIHQZSI-YXWLHULHSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
MXJGKTHZWIGRJG-UHFFFAOYSA-N tert-butyl 2-aminooxyacetate Chemical compound CC(C)(C)OC(=O)CON MXJGKTHZWIGRJG-UHFFFAOYSA-N 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000001974 tryptic soy broth Substances 0.000 description 1
239000006150 trypticase soy agar Substances 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA000616635A 1977-03-14 1993-03-31 Derives thiazolylique, utiles come intermediaires pour la preparation decepheme et de cephemes Expired - Lifetime CA1340499C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB10699/77		1977-03-14
GB29245/77		1977-07-12
GB42315/77		1977-10-11
GB75/78		1978-01-03
CA000298883A CA1321580C (fr)	1977-03-14	1978-03-14	Composes de cephem et de cepham et mode de preparation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000298883A Division CA1321580C (fr)	1977-03-14	1978-03-14	Composes de cephem et de cepham et mode de preparation

Publications (1)

Publication Number	Publication Date
CA1340499C true CA1340499C (fr)	1999-04-13

Family

ID=4110986

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616635A Expired - Lifetime CA1340499C (fr)	1977-03-14	1993-03-31	Derives thiazolylique, utiles come intermediaires pour la preparation decepheme et de cephemes

Country Status (1)

Country	Link
CA (1)	CA1340499C (fr)

1993
- 1993-03-31 CA CA000616635A patent/CA1340499C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2016-06-15	MKEX	Expiry	Effective date: 20160413

Publication	Publication Date	Title
US4604456A (en)	1986-08-05	Cephem and cepham compounds
US4370326A (en)	1983-01-25	Cephem compounds and composition
EP0007633B1 (fr)	1984-04-18	Céphalosporines, procédés pour leur préparation et compositions pharmaceutiques les contenant
US4341775A (en)	1982-07-27	Cephem compounds
CA1152062A (fr)	1983-08-16	Acides 3-cephem-4-carboxyliques disubstitues en 3 et 7, et procedes pour les fabriquer
US4729991A (en)	1988-03-08	Cephem compounds
GB2025933A (en)	1980-01-30	>Cephem and cepham compounds
US4698337A (en)	1987-10-06	Cephem compounds and processes for preparation thereof
US4427674A (en)	1984-01-24	Cephem compounds
US4923998A (en)	1990-05-08	Cephem and cepham compounds and processes for preparation thereof
CA1340499C (fr)	1999-04-13	Derives thiazolylique, utiles come intermediaires pour la preparation decepheme et de cephemes
US4399133A (en)	1983-08-16	Cephem compounds
US4400379A (en)	1983-08-23	Cephem compounds
US4393059A (en)	1983-07-12	Cephem compounds
US4841062A (en)	1989-06-20	New cephem and cepham compounds and processes for preparation thereof
IE46674B1 (en)	1983-08-24	New cephem and cepham compounds and processes for preparation thereof
GB2033377A (en)	1980-05-21	New Cephem Compounds and Processes for Preparation Thereof
GB2039890A (en)	1980-08-20	New cephem compounds
JPH0354953B2 (fr)	1991-08-21
CA1176240A (fr)	1984-10-16	Composes de cephem, procedes de preparation et composes pharmaceutique les contenant
GB2034692A (en)	1980-06-11	New cephem compounds and processes for preparation thereof
CA1112237A (fr)	1981-11-10	Composes cephem et procedes de fabrication
KR820000928B1 (ko)	1982-05-26	신규의 세펨 및 세팜 화합물의 제조방법
CA1112238A (fr)	1981-11-10	Composes cephem et procedes de fabrication
KR820000905B1 (ko)	1982-05-24	신규의 세펨 및 세팜 화합물의 제조방법