JPS6145629B2 - - Google Patents
Info
- Publication number
- JPS6145629B2 JPS6145629B2 JP36376A JP36376A JPS6145629B2 JP S6145629 B2 JPS6145629 B2 JP S6145629B2 JP 36376 A JP36376 A JP 36376A JP 36376 A JP36376 A JP 36376A JP S6145629 B2 JPS6145629 B2 JP S6145629B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- absorption spectrum
- syn isomer
- hydroxyimino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 carbamoyloxy group Chemical group 0.000 claims description 173
- 150000003839 salts Chemical class 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000002252 acyl group Chemical group 0.000 claims description 29
- 125000003277 amino group Chemical group 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004149 thio group Chemical group *S* 0.000 claims description 8
- 238000003379 elimination reaction Methods 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000000862 absorption spectrum Methods 0.000 description 127
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
- 239000000243 solution Substances 0.000 description 107
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 87
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 238000003756 stirring Methods 0.000 description 52
- 238000005481 NMR spectroscopy Methods 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 238000001816 cooling Methods 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 26
- 239000000284 extract Substances 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 235000011054 acetic acid Nutrition 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- 239000010410 layer Substances 0.000 description 14
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 13
- 150000008064 anhydrides Chemical class 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000005917 acylation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 9
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- LZMKLGSLUKISQE-UHFFFAOYSA-N hydroxylamine;methanol Chemical compound OC.ON LZMKLGSLUKISQE-UHFFFAOYSA-N 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- YNTPIKSPJIQDTM-UHFFFAOYSA-N 2-hydroxyimino-2-(3-hydroxyphenyl)acetic acid Chemical compound ON=C(C(O)=O)C1=CC=CC(O)=C1 YNTPIKSPJIQDTM-UHFFFAOYSA-N 0.000 description 5
- 150000001243 acetic acids Chemical class 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- 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 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- AJDQQGNUNIRWTE-UHFFFAOYSA-N 2-hydroxyimino-2-(3-methoxyphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC(=CC=C1)OC AJDQQGNUNIRWTE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 3
- RMSHYQAVCSUECE-UHFFFAOYSA-N hexane-1-sulfonamide Chemical compound CCCCCCS(N)(=O)=O RMSHYQAVCSUECE-UHFFFAOYSA-N 0.000 description 3
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 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 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical class C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- NIGSPCOEBMYIBR-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(3-hydroxyphenyl)acetic acid Chemical compound ClC(Cl)C(=O)ON=C(C(=O)O)C1=CC=CC(O)=C1 NIGSPCOEBMYIBR-UHFFFAOYSA-N 0.000 description 2
- NIVQTMCOFWYSQN-UHFFFAOYSA-N 2-(2,2-dimethylpropanoyloxyimino)-2-(3-hydroxyphenyl)acetic acid Chemical compound CC(C)(C)C(=O)ON=C(C(O)=O)C1=CC=CC(O)=C1 NIVQTMCOFWYSQN-UHFFFAOYSA-N 0.000 description 2
- ZOUPGSMSNQLUNW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C(Cl)=C1 ZOUPGSMSNQLUNW-UHFFFAOYSA-N 0.000 description 2
- KCAQYACZOPLTNA-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-2-(2,2-dichloroacetyl)oxyiminoacetic acid Chemical compound ClC(Cl)C(=O)ON=C(C(=O)O)C1=CC=C(O)C(Cl)=C1 KCAQYACZOPLTNA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZBVBBDBIFKYALY-UHFFFAOYSA-N 2-(3-fluorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=CC(F)=C1 ZBVBBDBIFKYALY-UHFFFAOYSA-N 0.000 description 2
- NBDYDHVCTKPDRI-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=CC(O)=C1 NBDYDHVCTKPDRI-UHFFFAOYSA-N 0.000 description 2
- JOZCNWTTZMKMKP-UHFFFAOYSA-N 2-(3-nitro-4-phenylmethoxyphenyl)-2-oxoacetic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)C(=O)O)=CC=C1OCC1=CC=CC=C1 JOZCNWTTZMKMKP-UHFFFAOYSA-N 0.000 description 2
- YRGDGXWJSRZRAS-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(F)C=C1 YRGDGXWJSRZRAS-UHFFFAOYSA-N 0.000 description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- PWURXZPHZHSYPJ-UHFFFAOYSA-N 2-[3-(methanesulfonamido)-4-phenylmethoxyphenyl]-2-oxoacetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=O)C(O)=O)=CC=C1OCC1=CC=CC=C1 PWURXZPHZHSYPJ-UHFFFAOYSA-N 0.000 description 2
- FWTDSRYPEAXBRI-UHFFFAOYSA-N 2-[4-(methanesulfonamido)phenyl]-2-oxoacetic acid Chemical compound CS(=O)(=O)NC1=CC=C(C(=O)C(O)=O)C=C1 FWTDSRYPEAXBRI-UHFFFAOYSA-N 0.000 description 2
- ZFQADUSHPKPJTR-UHFFFAOYSA-N 2-hydroxyimino-2-(2-methoxyphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=C(C=CC=C1)OC ZFQADUSHPKPJTR-UHFFFAOYSA-N 0.000 description 2
- NQZKNSCIXDWCRQ-UHFFFAOYSA-N 2-hydroxyimino-2-(3-sulfamoylphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC(=CC=C1)S(N)(=O)=O NQZKNSCIXDWCRQ-UHFFFAOYSA-N 0.000 description 2
- CQXXFDXFOYSHGN-UHFFFAOYSA-N 2-hydroxyimino-2-(4-hydroxy-3-nitrophenyl)acetic acid Chemical compound ON=C(C(O)=O)C1=CC=C(O)C([N+]([O-])=O)=C1 CQXXFDXFOYSHGN-UHFFFAOYSA-N 0.000 description 2
- OVBGBEMEEJPJQV-UHFFFAOYSA-N 2-hydroxyimino-2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(C(=NO)C(O)=O)C=C1 OVBGBEMEEJPJQV-UHFFFAOYSA-N 0.000 description 2
- MEZKYYGDPRNGAG-UHFFFAOYSA-N 2-hydroxyimino-2-[4-(methanesulfonamido)phenyl]acetic acid Chemical compound ON=C(C(=O)O)C1=CC=C(C=C1)NS(=O)(=O)C MEZKYYGDPRNGAG-UHFFFAOYSA-N 0.000 description 2
- ULGNNGRBOQYCDH-UHFFFAOYSA-N 2-hydroxyimino-2-[4-hydroxy-3-(methanesulfonamido)phenyl]acetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=NO)C(O)=O)=CC=C1O ULGNNGRBOQYCDH-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- RREPYIWLDJQENS-UHFFFAOYSA-N 4-nitrophenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=C([N+]([O-])=O)C=C1 RREPYIWLDJQENS-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 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 2
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 125000005425 toluyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZJIANJKJAAXAOC-HWZXHQHMSA-N (6r)-7-amino-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)C(N)[C@H]21 ZJIANJKJAAXAOC-HWZXHQHMSA-N 0.000 description 1
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GMTSPBYBJKGPJF-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(O)C(Cl)=C1 GMTSPBYBJKGPJF-UHFFFAOYSA-N 0.000 description 1
- ABXGMGUHGLQMAW-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(F)(F)F)=C1 ABXGMGUHGLQMAW-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical compound ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 description 1
- OTTXCOAOKOEENK-UHFFFAOYSA-N 2,2-difluoroethenone Chemical group FC(F)=C=O OTTXCOAOKOEENK-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- LZOMVUKEFVQHEK-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(2-methoxyphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=C(C=CC=C1)OC)Cl LZOMVUKEFVQHEK-UHFFFAOYSA-N 0.000 description 1
- KWKNEXCHGJFOOP-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(3-methoxyphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC(=CC=C1)OC)Cl KWKNEXCHGJFOOP-UHFFFAOYSA-N 0.000 description 1
- YAXOKAWRCKNXDQ-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(3-methylphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C=1C=C(C=CC=1)C)Cl YAXOKAWRCKNXDQ-UHFFFAOYSA-N 0.000 description 1
- VNRMUMAGPAXDQZ-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-hydroxy-3-methoxyphenyl)acetic acid Chemical compound COC1=CC(C(=NOC(=O)C(Cl)Cl)C(O)=O)=CC=C1O VNRMUMAGPAXDQZ-UHFFFAOYSA-N 0.000 description 1
- REIGARMSUIDPOX-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-hydroxyphenyl)acetic acid Chemical compound ClC(Cl)C(=O)ON=C(C(=O)O)C1=CC=C(O)C=C1 REIGARMSUIDPOX-UHFFFAOYSA-N 0.000 description 1
- FTZIIZXNUCHEMY-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-methoxyphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC=C(C=C1)OC)Cl FTZIIZXNUCHEMY-UHFFFAOYSA-N 0.000 description 1
- GPLDXMYJJHWWNZ-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-methylphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC=C(C=C1)C)Cl GPLDXMYJJHWWNZ-UHFFFAOYSA-N 0.000 description 1
- CSYRYBHTQYCLAI-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-methylsulfanylphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC=C(C=C1)SC)Cl CSYRYBHTQYCLAI-UHFFFAOYSA-N 0.000 description 1
- CIYXBPYTRNIRMN-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-phenylmethoxyphenyl)acetic acid Chemical compound C1=CC(C(=NOC(=O)C(Cl)Cl)C(=O)O)=CC=C1OCC1=CC=CC=C1 CIYXBPYTRNIRMN-UHFFFAOYSA-N 0.000 description 1
- KMPVUUIJJHBKKO-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-propan-2-ylphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC=C(C=C1)C(C)C)Cl KMPVUUIJJHBKKO-UHFFFAOYSA-N 0.000 description 1
- JSKVZOZJKCPHKZ-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-(4-propoxyphenyl)acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC=C(C=C1)OCCC)Cl JSKVZOZJKCPHKZ-UHFFFAOYSA-N 0.000 description 1
- IKDLAZVCHUZNSK-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-[3-(methanesulfonamido)phenyl]acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC(=CC=C1)NS(=O)(=O)C)Cl IKDLAZVCHUZNSK-UHFFFAOYSA-N 0.000 description 1
- JAMLILHZUNFSSW-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC(=CC=C1)C(F)(F)F)Cl JAMLILHZUNFSSW-UHFFFAOYSA-N 0.000 description 1
- DQQVEHHYEJVWFX-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-[4-(methanesulfonamido)phenyl]acetic acid Chemical compound ClC(C(=O)ON=C(C(=O)O)C1=CC=C(C=C1)NS(=O)(=O)C)Cl DQQVEHHYEJVWFX-UHFFFAOYSA-N 0.000 description 1
- FTQGIKNITXCBAV-UHFFFAOYSA-N 2-(2,2-dichloroacetyl)oxyimino-2-[4-hydroxy-3-(methanesulfonamido)phenyl]acetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=NOC(=O)C(Cl)Cl)C(O)=O)=CC=C1O FTQGIKNITXCBAV-UHFFFAOYSA-N 0.000 description 1
- JTXYGIVWNOQIBB-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Cl)C=C1Cl JTXYGIVWNOQIBB-UHFFFAOYSA-N 0.000 description 1
- FECOOTOWJXGHGV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Cl)C(Cl)=C1 FECOOTOWJXGHGV-UHFFFAOYSA-N 0.000 description 1
- MMCOTMRRXSOFLF-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC(Cl)=CC(Cl)=C1 MMCOTMRRXSOFLF-UHFFFAOYSA-N 0.000 description 1
- HGZZXAIQRPGHLO-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(O)C(Cl)=C1 HGZZXAIQRPGHLO-UHFFFAOYSA-N 0.000 description 1
- MSKLUHOSYJHLTI-UHFFFAOYSA-N 2-(3-chloro-4-phenylmethoxyphenyl)-2-oxoacetic acid Chemical compound ClC1=CC(C(=O)C(=O)O)=CC=C1OCC1=CC=CC=C1 MSKLUHOSYJHLTI-UHFFFAOYSA-N 0.000 description 1
- JNZGKTPLNIBLEW-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-(2-thiophen-2-ylacetyl)oxyiminoacetic acid Chemical compound C=1C=CC(O)=CC=1C(C(=O)O)=NOC(=O)CC1=CC=CS1 JNZGKTPLNIBLEW-UHFFFAOYSA-N 0.000 description 1
- CGXXIWFTHWCOPO-UHFFFAOYSA-N 2-(3-methoxyphenyl)-2-oxoacetic acid Chemical compound COC1=CC=CC(C(=O)C(O)=O)=C1 CGXXIWFTHWCOPO-UHFFFAOYSA-N 0.000 description 1
- GZXVAVNQNKCFFN-UHFFFAOYSA-N 2-(3-methylphenyl)-2-oxoacetic acid Chemical compound CC1=CC=CC(C(=O)C(O)=O)=C1 GZXVAVNQNKCFFN-UHFFFAOYSA-N 0.000 description 1
- WFLZZURFYPMNDF-UHFFFAOYSA-N 2-(3-nitrophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=CC([N+]([O-])=O)=C1 WFLZZURFYPMNDF-UHFFFAOYSA-N 0.000 description 1
- WUKHOVCMWXMOOA-UHFFFAOYSA-N 2-(3-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC([N+]([O-])=O)=C1 WUKHOVCMWXMOOA-UHFFFAOYSA-N 0.000 description 1
- AVHCIYOWJGANLN-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-hydroxyiminoacetic acid Chemical compound ON=C(C(O)=O)C1=CC=C(F)C=C1 AVHCIYOWJGANLN-UHFFFAOYSA-N 0.000 description 1
- WGAHPPCMFJHWPP-UHFFFAOYSA-N 2-(4-hydroxy-3-nitrophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 WGAHPPCMFJHWPP-UHFFFAOYSA-N 0.000 description 1
- UIIIPQVTXBPHTI-UHFFFAOYSA-N 2-(4-methylphenyl)-2-oxoacetic acid Chemical compound CC1=CC=C(C(=O)C(O)=O)C=C1 UIIIPQVTXBPHTI-UHFFFAOYSA-N 0.000 description 1
- ABWSHWSJDKGYQN-UHFFFAOYSA-N 2-[3-(methanesulfonamido)phenyl]-2-oxoacetic acid Chemical compound CS(=O)(=O)NC1=CC=CC(C(=O)C(O)=O)=C1 ABWSHWSJDKGYQN-UHFFFAOYSA-N 0.000 description 1
- GEKBROMUFSODAO-UHFFFAOYSA-N 2-[4-(methylamino)phenyl]-2-oxoacetic acid Chemical compound N(C1=CC=C(C(=O)C(=O)O)C=C1)C GEKBROMUFSODAO-UHFFFAOYSA-N 0.000 description 1
- VVNFXLVZTCJWKX-UHFFFAOYSA-N 2-[4-hydroxy-3-(methanesulfonamido)phenyl]-2-oxoacetic acid Chemical compound CS(=O)(=O)NC1=CC(C(=O)C(O)=O)=CC=C1O VVNFXLVZTCJWKX-UHFFFAOYSA-N 0.000 description 1
- DWQONSPEUHUORD-UHFFFAOYSA-N 2-benzoyloxyimino-2-(3-hydroxyphenyl)acetic acid Chemical compound C=1C=CC(O)=CC=1C(C(=O)O)=NOC(=O)C1=CC=CC=C1 DWQONSPEUHUORD-UHFFFAOYSA-N 0.000 description 1
- PVMJVPDVPWEXTM-UHFFFAOYSA-N 2-benzoyloxyimino-2-(4-hydroxyphenyl)acetic acid Chemical compound C=1C=C(O)C=CC=1C(C(=O)O)=NOC(=O)C1=CC=CC=C1 PVMJVPDVPWEXTM-UHFFFAOYSA-N 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
- FOLKAHKIMFCEGX-UHFFFAOYSA-N 2-hydroxyimino-2-(3-methylphenyl)acetic acid Chemical compound ON=C(C(=O)O)C=1C=C(C=CC=1)C FOLKAHKIMFCEGX-UHFFFAOYSA-N 0.000 description 1
- KGHVUNZBISSSKM-UHFFFAOYSA-N 2-hydroxyimino-2-(4-hydroxyphenyl)acetic acid Chemical compound ON=C(C(O)=O)C1=CC=C(O)C=C1 KGHVUNZBISSSKM-UHFFFAOYSA-N 0.000 description 1
- SSWCBBFARUNCCR-UHFFFAOYSA-N 2-hydroxyimino-2-(4-methoxyphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC=C(C=C1)OC SSWCBBFARUNCCR-UHFFFAOYSA-N 0.000 description 1
- MTWMOXVOZINGCS-UHFFFAOYSA-N 2-hydroxyimino-2-(4-methylsulfanylphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC=C(C=C1)SC MTWMOXVOZINGCS-UHFFFAOYSA-N 0.000 description 1
- CJKPOFMKEAGKCQ-UHFFFAOYSA-N 2-hydroxyimino-2-(4-phenylmethoxyphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC=C(C=C1)OCC1=CC=CC=C1 CJKPOFMKEAGKCQ-UHFFFAOYSA-N 0.000 description 1
- PQKZTNVNVKANRC-UHFFFAOYSA-N 2-hydroxyimino-2-(4-propan-2-ylphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC=C(C=C1)C(C)C PQKZTNVNVKANRC-UHFFFAOYSA-N 0.000 description 1
- CLYYOVUTTDQWED-UHFFFAOYSA-N 2-hydroxyimino-2-(4-propoxyphenyl)acetic acid Chemical compound ON=C(C(=O)O)C1=CC=C(C=C1)OCCC CLYYOVUTTDQWED-UHFFFAOYSA-N 0.000 description 1
- IFIZGBTXHKTYDM-UHFFFAOYSA-N 2-hydroxyimino-2-[3-(methanesulfonamido)phenyl]acetic acid Chemical compound ON=C(C(=O)O)C1=CC(=CC=C1)NS(=O)(=O)C IFIZGBTXHKTYDM-UHFFFAOYSA-N 0.000 description 1
- UFVAOSVIVZFWFN-UHFFFAOYSA-N 2-hydroxyimino-2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound ON=C(C(O)=O)C1=CC=CC(C(F)(F)F)=C1 UFVAOSVIVZFWFN-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- UQQMNAKUWQWIMD-UHFFFAOYSA-N 2-naphthalen-2-yl-2-oxoacetic acid Chemical compound C1=CC=CC2=CC(C(=O)C(=O)O)=CC=C21 UQQMNAKUWQWIMD-UHFFFAOYSA-N 0.000 description 1
- IQCFXSPOUDTJGL-UHFFFAOYSA-N 2-oxo-2-(3-sulfamoylphenyl)acetic acid Chemical compound S(N)(=O)(=O)C=1C=C(C=CC=1)C(C(=O)O)=O IQCFXSPOUDTJGL-UHFFFAOYSA-N 0.000 description 1
- JNFOOEYPNCGZRV-UHFFFAOYSA-N 2-oxo-2-(4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(C(=O)C(O)=O)C=C1 JNFOOEYPNCGZRV-UHFFFAOYSA-N 0.000 description 1
- APJFBBHXNCTOGI-UHFFFAOYSA-N 2-oxo-2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)C(=O)C1=CC=CC(C(F)(F)F)=C1 APJFBBHXNCTOGI-UHFFFAOYSA-N 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
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- FVMDYYGIDFPZAX-UHFFFAOYSA-N 3-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=CC(O)=C1 FVMDYYGIDFPZAX-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
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- XXYNZSATHOXXBJ-UHFFFAOYSA-N 4-hydroxyisoindole-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)NC2=O XXYNZSATHOXXBJ-UHFFFAOYSA-N 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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZUWVTLVMLIVAAI-UHFFFAOYSA-N COC1=CC(C(=NO)C(O)=O)=CC=C1O Chemical compound COC1=CC(C(=NO)C(O)=O)=CC=C1O ZUWVTLVMLIVAAI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-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
- OFFJPZUUCPNHSX-UHFFFAOYSA-N ON=C(C(O)=O)C1=CC=C(O)C(Cl)=C1 Chemical compound ON=C(C(O)=O)C1=CC=C(O)C(Cl)=C1 OFFJPZUUCPNHSX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 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 1
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 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
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002170 ethers Chemical class 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
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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
- 238000002955 isolation Methods 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])[H] 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 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
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- PNTMGOUAICFJQK-UHFFFAOYSA-N phenyl pyruvic acid oxime Natural products ON=C(C(O)=O)CC1=CC=CC=C1 PNTMGOUAICFJQK-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 125000000405 phenylalanyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- PNTMGOUAICFJQK-NTMALXAHSA-N phenylpyruvic acid oxime Chemical compound O\N=C(C(O)=O)\CC1=CC=CC=C1 PNTMGOUAICFJQK-NTMALXAHSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-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
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000011593 sulfur Substances 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
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36376A JPS5283784A (en) | 1976-01-01 | 1976-01-01 | 7-substituted alkaneamide-3-substituted-3-cephem-4-carboxylic acid, it s derivative and salt |
| BE164026A BE838190A (fr) | 1975-02-04 | 1976-02-02 | Procede de preparation d'acides (7-acetamido,2-disubstitue)-3-substitue-3-cephem-4-carboxyliques et nouveaux produits ainsi obtenus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36376A JPS5283784A (en) | 1976-01-01 | 1976-01-01 | 7-substituted alkaneamide-3-substituted-3-cephem-4-carboxylic acid, it s derivative and salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5283784A JPS5283784A (en) | 1977-07-12 |
| JPS6145629B2 true JPS6145629B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-10-08 |
Family
ID=11471705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP36376A Granted JPS5283784A (en) | 1975-02-04 | 1976-01-01 | 7-substituted alkaneamide-3-substituted-3-cephem-4-carboxylic acid, it s derivative and salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5283784A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5616490A (en) * | 1979-07-18 | 1981-02-17 | Hoechst Ag | Cephem compound manufacture |
-
1976
- 1976-01-01 JP JP36376A patent/JPS5283784A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5283784A (en) | 1977-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5110921A (en) | 7-acylamino-3-vinylcephalosporanic acid derivatives | |
| US4680390A (en) | Esters of 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methyl-ceph-3-em-4-carboxylic acid | |
| US4166115A (en) | Syn 7-oxoimino substituted derivatives of cephalosporanic acid | |
| JPS5941995B2 (ja) | ３，７−ジ置換−３−セフエム−４−カルボン酸化合物およびその塩類およびそれらの製造方法 | |
| JPS6337114B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4596869A (en) | Pyridinyl and pyrimidinyl derivatives | |
| JPS6320435B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0177940A2 (en) | Hydrazine derivatives and their use | |
| US4039536A (en) | 7-(α-SUBSTITUTED GLYCINAMIDO)-3-SUBSTITUTED METHYL-3-CEPHEM-4-CARBOXYLIC ACIDS AND THEIR DERIVATIVES | |
| JPH0144715B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CA1251443A (fr) | Procede de preparation de derives de l'acide 1-dethia 2-thia cephalosporanique | |
| FR2496106A1 (fr) | Derives d'acide 7-acylaminocephalosporanique et procede pour leur preparation | |
| US4143166A (en) | 7[(2-Hydroxyamino-2-disubstituted phenyl-acetamido)-]3-heterocyclicthio-3-cephem-4-carboxylic acids | |
| US4350692A (en) | 3,7-Disubstituted-3-cephem-4-carboxylic acids | |
| JPS6145629B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4731443A (en) | 7-acylamino-3-vinylcephalosporanic acid derivatives | |
| JP2529093B2 (ja) | セファロスポリン中間体の製造方法 | |
| US5252731A (en) | Cephalosporin intermediates | |
| US4254117A (en) | 7-(α,α-Disubstituted-acetemido)-3-substituted-3-cephem-4-carboxylic acids | |
| US4473566A (en) | 7-(α, α-Disubstituted-acetamido)-3-substituted-3-cephem-4-carboxylic acids | |
| US4871860A (en) | Syn-isomer of 3,7-disubstituted-3-cephem-4-caroxylic acid compounds and processes for the preparation thereof | |
| JPH0316358B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS6145630B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4085277A (en) | 7(2-Phenyl or thienyl-2-isonicotinoyloxyacetamido)-3-(1-methyl-1-H tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid | |
| JPS6145628B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |