NO750471L

NO750471L -

Info

Publication number: NO750471L
Authority: NO; Norway
Prior art keywords: methylene; methyl; carboxylate; penam; trichloroethyl
Prior art date: 1972-11-22

Application number

NO750471A

Other languages

English (en)

Norwegian (no)

Inventor

T Kamiya

T Teraji

M Hashimoto

O Nakaguti

T Oku

Original Assignee

Fujisawa Pharmaceutical Co

Priority date

1972-11-22

Filing date

1975-02-13

Publication date

1974-05-24

1972-11-22 Priority claimed from JP11738572A external-priority patent/JPS5727114B2/ja

1972-11-27 Priority claimed from JP11911372A external-priority patent/JPS5727115B2/ja

1972-12-15 Priority claimed from JP12663672A external-priority patent/JPS5535397B2/ja

1973-08-02 Priority claimed from JP8785573A external-priority patent/JPS5643472B2/ja

1973-08-02 Priority claimed from JP8785173A external-priority patent/JPS5641635B2/ja

1973-08-02 Priority claimed from JP8785473A external-priority patent/JPS5643471B2/ja

1974-05-24 Publication of NO750471L publication Critical patent/NO750471L/no

1975-02-13 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

Links

150000001875 compounds Chemical class 0.000 claims description 77
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
125000006239 protecting group Chemical group 0.000 claims description 38
125000003277 amino group Chemical group 0.000 claims description 32
238000003379 elimination reaction Methods 0.000 claims description 32
238000000034 method Methods 0.000 claims description 30
125000004442 acylamino group Chemical group 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
230000007062 hydrolysis Effects 0.000 claims description 16
238000006460 hydrolysis reaction Methods 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 5
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
230000008569 process Effects 0.000 claims description 2
-1 ethylidene, propylidene Chemical group 0.000 description 291
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 276
239000000243 solution Substances 0.000 description 235
238000002844 melting Methods 0.000 description 158
230000008018 melting Effects 0.000 description 158
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 150
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
238000006243 chemical reaction Methods 0.000 description 128
239000000203 mixture Substances 0.000 description 113
238000000354 decomposition reaction Methods 0.000 description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 95
125000002252 acyl group Chemical group 0.000 description 91
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 84
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 78
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 72
238000001816 cooling Methods 0.000 description 70
239000002904 solvent Substances 0.000 description 69
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 58
229920006395 saturated elastomer Polymers 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
239000011541 reaction mixture Substances 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
238000000862 absorption spectrum Methods 0.000 description 45
239000002253 acid Substances 0.000 description 44
229910052943 magnesium sulfate Inorganic materials 0.000 description 42
235000019341 magnesium sulphate Nutrition 0.000 description 42
230000002829 reductive effect Effects 0.000 description 41
235000017557 sodium bicarbonate Nutrition 0.000 description 39
229910000030 sodium bicarbonate Inorganic materials 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 31
239000013078 crystal Substances 0.000 description 31
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 29
239000000284 extract Substances 0.000 description 29
239000011780 sodium chloride Substances 0.000 description 29
239000003921 oil Substances 0.000 description 27
239000003795 chemical substances by application Substances 0.000 description 26
239000012071 phase Substances 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
238000003756 stirring Methods 0.000 description 24
239000005457 ice water Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 22
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 21
230000009467 reduction Effects 0.000 description 20
238000006722 reduction reaction Methods 0.000 description 20
125000005907 alkyl ester group Chemical group 0.000 description 18
125000000623 heterocyclic group Chemical group 0.000 description 18
229910052751 metal Inorganic materials 0.000 description 18
239000002184 metal Substances 0.000 description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
238000001035 drying Methods 0.000 description 17
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 16
239000002585 base Substances 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
244000063299 Bacillus subtilis Species 0.000 description 14
235000014469 Bacillus subtilis Nutrition 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
241000191967 Staphylococcus aureus Species 0.000 description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 description 14
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
239000007788 liquid Substances 0.000 description 14
239000003054 catalyst Substances 0.000 description 13
238000001914 filtration Methods 0.000 description 13
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 13
125000001931 aliphatic group Chemical group 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 11
239000000463 material Substances 0.000 description 11
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 11
229910052717 sulfur Inorganic materials 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
239000011734 sodium Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 9
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 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
150000008065 acid anhydrides Chemical class 0.000 description 8
229910000147 aluminium phosphate Inorganic materials 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
125000004433 nitrogen atom Chemical group N* 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
239000007858 starting material Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
LOHYNSSHBWYMIH-PDQHRLGMSA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)CC1=CC=CC=C1 LOHYNSSHBWYMIH-PDQHRLGMSA-N 0.000 description 7
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
238000005917 acylation reaction Methods 0.000 description 7
230000002411 adverse Effects 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 7
230000008030 elimination Effects 0.000 description 7
125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
239000000047 product Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
125000004434 sulfur atom Chemical group 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QZSUZHYGLFTLHK-FNBKZIALSA-N (6R)-7-(1-cyclopropylethoxycarbonylamino)-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound S([C@@H]12)C3(C)CC3(C(O)=O)N1C(=O)C2NC(=O)OC(C)C1CC1 QZSUZHYGLFTLHK-FNBKZIALSA-N 0.000 description 6
UYHUOKIBOUMWAL-CBDLJCAGSA-N (6R)-7-[(2-amino-2-phenylacetyl)amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)C(N)C1=CC=CC=C1 UYHUOKIBOUMWAL-CBDLJCAGSA-N 0.000 description 6
JNCDPEQOAIAQNO-LELDVITJSA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)CN1C=NN=N1 JNCDPEQOAIAQNO-LELDVITJSA-N 0.000 description 6
DQHVASBKHNNFGJ-PDQHRLGMSA-N 2,2,2-trichloroethyl (6R)-7-[[2-(5-chlorobenzotriazol-1-yl)acetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound N1=NC2=CC(Cl)=CC=C2N1CC(=O)NC(C1=O)[C@@H]2N1C1(C(=O)OCC(Cl)(Cl)Cl)CC1(C)S2 DQHVASBKHNNFGJ-PDQHRLGMSA-N 0.000 description 6
GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 6
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
230000000845 anti-microbial effect Effects 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
239000011575 calcium Substances 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
238000010531 catalytic reduction reaction Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000006260 foam Substances 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
125000003396 thiol group Chemical group [H]S* 0.000 description 6
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 6
230000007306 turnover Effects 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
239000011701 zinc Substances 0.000 description 6
VLLBEUGNWBHYGD-BEBNOVJQSA-N (6R)-4-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)CC1=CC=CC=C1 VLLBEUGNWBHYGD-BEBNOVJQSA-N 0.000 description 5
ZXKIKUPOZPIBDM-ROWWNQKBSA-N (6R)-4-methyl-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)CN1C=NN=N1 ZXKIKUPOZPIBDM-ROWWNQKBSA-N 0.000 description 5
UZLZGDVIORCTPD-WIHCSHQRSA-N (6R)-7-(1,3-dioxoisoindol-2-yl)-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C1=O)[C@@H]2N1C1(C(O)=O)CC1(C)S2 UZLZGDVIORCTPD-WIHCSHQRSA-N 0.000 description 5
CBPLNAPEDXBLIS-IGIWYVGQSA-N (6R)-7-[[2-(1-cyclopropylethoxycarbonylamino)-2-phenylacetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1CC1C(C)OC(=O)NC(C(=O)NC1C(N2C3(CC3(C)S[C@@H]21)C(O)=O)=O)C1=CC=CC=C1 CBPLNAPEDXBLIS-IGIWYVGQSA-N 0.000 description 5
IQOFOCKHFKQESX-IXUVCCNTSA-N (6R)-7-amino-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound S([C@H]1N2C(C1N)=O)C1(C)C2(C(O)=O)C1 IQOFOCKHFKQESX-IXUVCCNTSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
FYGTXLGMKMLZDN-LELDVITJSA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-(propanethioylamino)-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound CC12S[C@H]3N(C1(C(=O)OCC(Cl)(Cl)Cl)C2)C(C3NC(CC)=S)=O FYGTXLGMKMLZDN-LELDVITJSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
125000001118 alkylidene group Chemical group 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
125000004432 carbon atom Chemical group C* 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
230000004992 fission Effects 0.000 description 5
125000005059 halophenyl group Chemical group 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
238000005406 washing Methods 0.000 description 5
KTFLQUDSAGDLEX-QDSWYCPBSA-N (6R)-4-methyl-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)CC1=CC=CS1 KTFLQUDSAGDLEX-QDSWYCPBSA-N 0.000 description 4
ZQTKOYZSIONQIF-BEBNOVJQSA-N (6R)-7-[(4-acetamidophenyl)sulfonylamino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1C(=O)N2C3(C(O)=O)CC3(C)S[C@@H]21 ZQTKOYZSIONQIF-BEBNOVJQSA-N 0.000 description 4
YLTVROOFBFMRII-SZUSMBQYSA-N (6R)-7-[[2-(2-chlorophenoxy)-2-phenylacetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1Cl YLTVROOFBFMRII-SZUSMBQYSA-N 0.000 description 4
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 4
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
PTXYLSLTXMRVLP-NFUVDBBGSA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)CC1=CC=CS1 PTXYLSLTXMRVLP-NFUVDBBGSA-N 0.000 description 4
YCSFAOKUWXMVGV-LXMRASDZSA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-[[2-(1,3,4-thiadiazol-2-ylsulfanyl)acetyl]amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)CSC1=NN=CS1 YCSFAOKUWXMVGV-LXMRASDZSA-N 0.000 description 4
QLAJZLYQXPNVRA-VGSCRWOPSA-N 2,2,2-trichloroethyl (6R)-7-(1-cyclopropylethoxycarbonylamino)-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound S([C@@H]12)C3(C)CC3(C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C2NC(=O)OC(C)C1CC1 QLAJZLYQXPNVRA-VGSCRWOPSA-N 0.000 description 4
SSRZCSSHGXSSEP-PDQHRLGMSA-N 2,2,2-trichloroethyl (6R)-7-[(4-acetamidophenyl)sulfonylamino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1C(=O)N2C3(C(=O)OCC(Cl)(Cl)Cl)CC3(C)S[C@@H]21 SSRZCSSHGXSSEP-PDQHRLGMSA-N 0.000 description 4
BOROVWLJRAYIJM-CRXSXSLSSA-N 2,2,2-trichloroethyl (6R)-7-[[2-(2-chlorophenoxy)-2-phenylacetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1Cl BOROVWLJRAYIJM-CRXSXSLSSA-N 0.000 description 4
VMRRYLXYKUDIHK-GFRIJPEDSA-N C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)C(OC=O)C1=CC=CC=C1 Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)C(OC=O)C1=CC=CC=C1 VMRRYLXYKUDIHK-GFRIJPEDSA-N 0.000 description 4
SQFFDCMHIVWBIS-AYKRLLGKSA-N C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)C(OC=O)C1=CC=CC=C1 Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)C(OC=O)C1=CC=CC=C1 SQFFDCMHIVWBIS-AYKRLLGKSA-N 0.000 description 4
OEXQYEGNIBMUFF-VDECZMLJSA-N C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)SC1=CC=CC=C1 Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)SC1=CC=CC=C1 OEXQYEGNIBMUFF-VDECZMLJSA-N 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
125000000068 chlorophenyl group Chemical group 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000004464 hydroxyphenyl group Chemical group 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000012046 mixed solvent Substances 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
125000005270 trialkylamine group Chemical group 0.000 description 4
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
JNFHOVZVUQLBIC-VDECZMLJSA-N (6R)-4-methyl-8-oxo-7-(phenylcarbamoylamino)-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)NC1=CC=CC=C1 JNFHOVZVUQLBIC-VDECZMLJSA-N 0.000 description 3
LUWIHRPEQASMDD-AOUJSESGSA-N (6R)-7-[[2-(carbamoylhydrazinylidene)-2-phenylacetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound CC12CC1(N1[C@H](S2)C(NC(=O)C(=NNC(N)=O)c2ccccc2)C1=O)C(O)=O LUWIHRPEQASMDD-AOUJSESGSA-N 0.000 description 3
DSXGLMTUNGWCNS-SHBZDDKHSA-N (6R)-7-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound S([C@@H]12)C3(C)CC3(C(O)=O)N1C(=O)C2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl DSXGLMTUNGWCNS-SHBZDDKHSA-N 0.000 description 3
XIOOZFGKTBHELQ-FRGVBBCASA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-(phenylcarbamoylamino)-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)NC1=CC=CC=C1 XIOOZFGKTBHELQ-FRGVBBCASA-N 0.000 description 3
JGOBCXBVXNMTMA-PXAXEPKDSA-N 2,2,2-trichloroethyl (6R)-7-[[2-(carbamoylhydrazinylidene)-2-phenylacetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound CC12S[C@H]3N(C1(C(=O)OCC(Cl)(Cl)Cl)C2)C(C3NC(C(=NNC(=O)N)C1=CC=CC=C1)=O)=O JGOBCXBVXNMTMA-PXAXEPKDSA-N 0.000 description 3
XCQODHOBWUJHPM-NRSPIOJWSA-N 2,2,2-trichloroethyl (6R)-7-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound S([C@@H]12)C3(C)CC3(C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl XCQODHOBWUJHPM-NRSPIOJWSA-N 0.000 description 3
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
RMSSYWDDAUQMCU-FRGVBBCASA-N C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)SC1=CC=CC=C1 Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)SC1=CC=CC=C1 RMSSYWDDAUQMCU-FRGVBBCASA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000010933 acylation Effects 0.000 description 3
239000008272 agar Substances 0.000 description 3
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
MTRNNCLQPVCDLF-UHFFFAOYSA-N benzyl-[2-(benzylazaniumyl)ethyl]azanium;diacetate Chemical compound CC(O)=O.CC(O)=O.C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 MTRNNCLQPVCDLF-UHFFFAOYSA-N 0.000 description 3
125000004799 bromophenyl group Chemical group 0.000 description 3
125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000010949 copper Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
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 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
125000005493 quinolyl group Chemical group 0.000 description 3
239000001119 stannous chloride Substances 0.000 description 3
235000011150 stannous chloride Nutrition 0.000 description 3
125000003944 tolyl group Chemical group 0.000 description 3
ODHHDZSIPMXQKS-ROWWNQKBSA-N (6R)-4-methyl-8-oxo-7-(propanethioylamino)-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound CC12S[C@H]3N(C1(C(=O)O)C2)C(C3NC(CC)=S)=O ODHHDZSIPMXQKS-ROWWNQKBSA-N 0.000 description 2
GSGYFONMZUKITC-WEULUIGLSA-N (6R)-4-methyl-8-oxo-7-[[2-(1,3,4-thiadiazol-2-ylsulfanyl)acetyl]amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)CSC1=NN=CS1 GSGYFONMZUKITC-WEULUIGLSA-N 0.000 description 2
MMVZBKNYLVCNCQ-CBDLJCAGSA-N (6R)-7-[(2-hydroxy-2-phenylacetyl)amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(O)=O)NC(=O)C(O)C1=CC=CC=C1 MMVZBKNYLVCNCQ-CBDLJCAGSA-N 0.000 description 2
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 2
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 2
125000006017 1-propenyl group Chemical group 0.000 description 2
MAGGFBLIULYYPJ-UHFFFAOYSA-N 2,2,2-triphenylethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(CN)C1=CC=CC=C1 MAGGFBLIULYYPJ-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
AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
VGYPPWDSDUKKCF-PLDNPXBTSA-N S([C@@H]12)C3(C)CC3(C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C2N=C(SC(=O)C)NC1=CC=C(Cl)C=C1 Chemical compound S([C@@H]12)C3(C)CC3(C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C2N=C(SC(=O)C)NC1=CC=C(Cl)C=C1 VGYPPWDSDUKKCF-PLDNPXBTSA-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
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 2
125000006323 alkenyl amino group Chemical group 0.000 description 2
125000005108 alkenylthio group Chemical group 0.000 description 2
125000005037 alkyl phenyl group Chemical group 0.000 description 2
125000005103 alkyl silyl group Chemical group 0.000 description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
150000007860 aryl ester derivatives Chemical class 0.000 description 2
125000005110 aryl thio group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
125000003460 beta-lactamyl group Chemical group 0.000 description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
125000005366 cycloalkylthio group Chemical group 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
150000004966 inorganic peroxy acids Chemical class 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
125000006501 nitrophenyl group Chemical group 0.000 description 2
150000004967 organic peroxy acids Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000001205 polyphosphate Substances 0.000 description 2
235000011176 polyphosphates Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
KZRSXWWFMZJBKT-VFVZMGMDSA-M sodium (6R)-4-methyl-8-oxo-7-(propanethioylamino)-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound CC12S[C@H]3N(C1(C(=O)[O-])C2)C(C3NC(CC)=S)=O.[Na+] KZRSXWWFMZJBKT-VFVZMGMDSA-M 0.000 description 2
KSQGSKMBTRZMHK-GYDYRDMNSA-M sodium (6R)-7-[(2-hydroxy-2-phenylacetyl)amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound [Na+].C1([C@@H]2N(C1=O)C1(CC1(S2)C)C([O-])=O)NC(=O)C(O)C1=CC=CC=C1 KSQGSKMBTRZMHK-GYDYRDMNSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
125000001113 thiadiazolyl group Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
239000011135 tin Substances 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
125000005023 xylyl group Chemical group 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
VRDLSRFTXIXAAJ-WHBRWTHLSA-N (6S)-7-[C-acetylsulfanyl-N-(4-chlorophenyl)carbonimidoyl]-6-amino-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylic acid Chemical compound CC12S[C@]3(N(C1(C(=O)O)C2)C(C3C(SC(C)=O)=NC1=CC=C(C=C1)Cl)=O)N VRDLSRFTXIXAAJ-WHBRWTHLSA-N 0.000 description 1
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
JFQJADVATLPJRF-IHWYPQMZSA-N (z)-3-bromobut-2-enoic acid Chemical compound C\C(Br)=C\C(O)=O JFQJADVATLPJRF-IHWYPQMZSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 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
MZZVFXMTZTVUFO-UHFFFAOYSA-N 1-chloro-4-isothiocyanatobenzene Chemical compound ClC1=CC=C(N=C=S)C=C1 MZZVFXMTZTVUFO-UHFFFAOYSA-N 0.000 description 1
DKKVKJZXOBFLRY-UHFFFAOYSA-N 1-cyclopropylethanol Chemical compound CC(O)C1CC1 DKKVKJZXOBFLRY-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
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
JEYFETKUECMYQL-PDQHRLGMSA-N 2,2,2-trichloroethyl (6R)-4-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)COC1=CC=CC=C1 JEYFETKUECMYQL-PDQHRLGMSA-N 0.000 description 1
KTFLMEHPMGCFPA-PDQHRLGMSA-N 2,2,2-trichloroethyl (6R)-7-[[2-(3-chlorophenyl)acetyl]amino]-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C1(CC1(S2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)CC1=CC=CC(Cl)=C1 KTFLMEHPMGCFPA-PDQHRLGMSA-N 0.000 description 1
FFPDOLBWTSOVJW-NCJUMLFWSA-N 2,2,2-trichloroethyl (6R)-7-amino-4-methyl-8-oxo-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound CC12S[C@H]3N(C1(C(=O)OCC(Cl)(Cl)Cl)C2)C(C3N)=O FFPDOLBWTSOVJW-NCJUMLFWSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
OFAFMGYQEWCODE-UHFFFAOYSA-N 2-(1,2,5-thiadiazol-3-yl)acetyl chloride Chemical compound ClC(=O)CC=1C=NSN=1 OFAFMGYQEWCODE-UHFFFAOYSA-N 0.000 description 1
DZXGDEPWZLFUEA-UHFFFAOYSA-N 2-(1,3,4-thiadiazol-2-ylsulfanyl)acetic acid Chemical compound OC(=O)CSC1=NN=CS1 DZXGDEPWZLFUEA-UHFFFAOYSA-N 0.000 description 1
OXZPECBWYAWVKM-UHFFFAOYSA-N 2-(1-cyclohexylethoxycarbonylamino)-2-phenylacetic acid Chemical compound C1(CCCCC1)C(C)OC(=O)NC(C1=CC=CC=C1)C(=O)O OXZPECBWYAWVKM-UHFFFAOYSA-N 0.000 description 1
PYPMKORNJLTHGP-UHFFFAOYSA-N 2-(3-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=CC(Cl)=C1 PYPMKORNJLTHGP-UHFFFAOYSA-N 0.000 description 1
XILFGRBBNJBMAB-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-1-yl)acetic acid Chemical compound ClC1=CC=C2N(CC(=O)O)N=NC2=C1 XILFGRBBNJBMAB-UHFFFAOYSA-N 0.000 description 1
GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 description 1
OLLIBHISBNYDDK-UHFFFAOYSA-N 2-[2-oxo-2-[2-(2-sulfophenyl)acetyl]oxyethyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1CC(=O)OC(=O)CC1=CC=CC=C1S(O)(=O)=O OLLIBHISBNYDDK-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
JSQPGNJFQUOEPA-UHFFFAOYSA-N 2-chloroethaneperoxoic acid Chemical compound OOC(=O)CCl JSQPGNJFQUOEPA-UHFFFAOYSA-N 0.000 description 1
CRIRLBRCPMTHFY-UHFFFAOYSA-N 2-cyclopropylethyl carbonochloridate Chemical compound ClC(=O)OCCC1CC1 CRIRLBRCPMTHFY-UHFFFAOYSA-N 0.000 description 1
AVZBOAGCVKEESJ-UHFFFAOYSA-O 2-ethyl-1,2-benzoxazol-2-ium-7-ol Chemical class C1=CC(O)=C2O[N+](CC)=CC2=C1 AVZBOAGCVKEESJ-UHFFFAOYSA-O 0.000 description 1
VYSRZETUSAOIMP-UHFFFAOYSA-N 2-furanacetic acid Chemical compound OC(=O)CC1=CC=CO1 VYSRZETUSAOIMP-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
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
FQHYQCXMFZHLAE-UHFFFAOYSA-N 25405-85-0 Chemical compound CC1(C)C2(OC(=O)C=3C=CC=CC=3)C1C1C=C(CO)CC(C(C(C)=C3)=O)(O)C3C1(O)C(C)C2OC(=O)C1=CC=CC=C1 FQHYQCXMFZHLAE-UHFFFAOYSA-N 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
BPDBLWKFVXHGFT-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound ClC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl BPDBLWKFVXHGFT-UHFFFAOYSA-N 0.000 description 1
UVEPOHNXGXVOJE-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl UVEPOHNXGXVOJE-UHFFFAOYSA-N 0.000 description 1
NSHAOELVDPKZIC-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonic acid;hydroxide Chemical compound [OH-].O1[N+](CC)=CC=C1C1=CC=CC(S(O)(=O)=O)=C1 NSHAOELVDPKZIC-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
CKWJMSJDPJKJON-UHFFFAOYSA-N 3-chloropent-2-enoic acid Chemical compound CCC(Cl)=CC(O)=O CKWJMSJDPJKJON-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
GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
NJQHZENQKNIRSY-UHFFFAOYSA-N 5-ethyl-1h-imidazole Chemical compound CCC1=CNC=N1 NJQHZENQKNIRSY-UHFFFAOYSA-N 0.000 description 1
UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
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 1
229910000497 Amalgam Inorganic materials 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
229910021555 Chromium Chloride Inorganic materials 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
229920002261 Corn starch Polymers 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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-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
108010010803 Gelatin Proteins 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
229920000084 Gum arabic Polymers 0.000 description 1
108010076876 Keratins Proteins 0.000 description 1
102000011782 Keratins Human genes 0.000 description 1
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 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
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-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
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
KMHQFOPCFWNICG-JAONHZHISA-N S([C@@H]12)C3(C)CC3(C(O)=O)N1C(=O)C2N=C(SC(=O)C)NC1=CC=C(Cl)C=C1 Chemical compound S([C@@H]12)C3(C)CC3(C(O)=O)N1C(=O)C2N=C(SC(=O)C)NC1=CC=C(Cl)C=C1 KMHQFOPCFWNICG-JAONHZHISA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
ZJZKZASVKGROEI-LYGLHFEFSA-M [Na+].C1([C@@H]2N(C1=O)C1(CC1(S2)C)C([O-])=O)NC(=O)C(OC=O)C1=CC=CC=C1 Chemical compound [Na+].C1([C@@H]2N(C1=O)C1(CC1(S2)C)C([O-])=O)NC(=O)C(OC=O)C1=CC=CC=C1 ZJZKZASVKGROEI-LYGLHFEFSA-M 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
UDAMVKNOORCKBK-UHFFFAOYSA-N acetic acid;n',n'-dibenzylethane-1,2-diamine Chemical compound CC(O)=O.C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 UDAMVKNOORCKBK-UHFFFAOYSA-N 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000001769 aryl amino 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
239000000022 bacteriostatic agent Substances 0.000 description 1
MNUYNGXMQRGJSJ-UHFFFAOYSA-N benzenecarbothioyl chloride Chemical compound ClC(=S)C1=CC=CC=C1 MNUYNGXMQRGJSJ-UHFFFAOYSA-N 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
125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
SDYPLFGAELJKMI-HCSIYLKJSA-N benzyl (5r)-3-(acetyloxymethyl)-3-methyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound C1([C@H]2SC(C(N2C1=O)C(=O)OCC=1C=CC=CC=1)(C)COC(=O)C)NC(=O)COC1=CC=CC=C1 SDYPLFGAELJKMI-HCSIYLKJSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
230000003115 biocidal effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 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
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 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
238000004587 chromatography analysis Methods 0.000 description 1
229960000359 chromic chloride Drugs 0.000 description 1
WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
239000011636 chromium(III) chloride Substances 0.000 description 1
235000007831 chromium(III) chloride Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
125000001485 cycloalkadienyl group Chemical group 0.000 description 1
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005886 esterification reaction Methods 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
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
VRHAQNTWKSVEEC-UHFFFAOYSA-N ethyl 1,3-dioxoisoindole-2-carboxylate Chemical compound C1=CC=C2C(=O)N(C(=O)OCC)C(=O)C2=C1 VRHAQNTWKSVEEC-UHFFFAOYSA-N 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
FZYXTYKAZUNHMF-UHFFFAOYSA-N formyl 2-hydroxy-2-phenylacetate Chemical compound C(=O)OC(C(O)C1=CC=CC=C1)=O FZYXTYKAZUNHMF-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000008101 lactose Substances 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
239000011133 lead Substances 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229940099273 magnesium trisilicate Drugs 0.000 description 1
229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
235000019793 magnesium trisilicate Nutrition 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
150000004704 methoxides Chemical class 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
IQEGZVKHSGBNTM-IDWHDZOISA-N methyl (5r)-3-(acetyloxymethyl)-3-methyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(C(S2)(C)COC(C)=O)C(=O)OC)NC(=O)COC1=CC=CC=C1 IQEGZVKHSGBNTM-IDWHDZOISA-N 0.000 description 1
HPMGGJWTWOXWHK-PDQHRLGMSA-N methyl (6R)-4-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate Chemical compound C1([C@H]2SC3(C)CC3(N2C1=O)C(=O)OC)NC(=O)COC1=CC=CC=C1 HPMGGJWTWOXWHK-PDQHRLGMSA-N 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical class C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 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
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 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
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 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
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 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
239000006072 paste Substances 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 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
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 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
239000008363 phosphate buffer Substances 0.000 description 1
150000003015 phosphoric acid halides Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
QRKVRHZNLKTPGF-UHFFFAOYSA-N phosphorus pentabromide Chemical compound BrP(Br)(Br)(Br)Br QRKVRHZNLKTPGF-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material 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
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-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
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
239000001974 tryptic soy broth Substances 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
239000012000 urushibara nickel Substances 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
229920001567 vinyl ester resin Polymers 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