NL8105468A

NL8105468A - 2-oxoazetidinederivaten, werkwijze ter bereiding hiervan en preparaten die deze derivaten bevatten.

2-oxoazetidinederivaten, werkwijze ter bereiding hiervan en preparaten die deze derivaten bevatten. Download PDF

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Publication number: NL8105468A
Authority: NL; Netherlands
Prior art keywords: group; oxoazetidine; formula; optionally substituted; added
Prior art date: 1980-12-05

Application number

NL8105468A

Other languages

English (en)

Dutch (nl)

Original Assignee

Takeda Chemical Industries Ltd

Priority date

1980-12-05

Filing date

1981-12-04

Publication date

1982-07-01

1980-12-05 Priority claimed from PCT/JP1980/000296 external-priority patent/WO1982001872A1/fr

1981-04-30 Priority claimed from PCT/JP1981/000102 external-priority patent/WO1982003858A1/fr

1981-08-25 Priority claimed from PCT/JP1981/000192 external-priority patent/WO1983000690A1/fr

1981-12-04 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1982-07-01 Publication of NL8105468A publication Critical patent/NL8105468A/nl

Links

238000000034 method Methods 0.000 title claims abstract description 177
238000002360 preparation method Methods 0.000 title claims description 171
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 70
125000003277 amino group Chemical group 0.000 claims abstract description 47
150000003839 salts Chemical class 0.000 claims abstract description 32
150000002148 esters Chemical class 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 13
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
108090000204 Dipeptidase 1 Proteins 0.000 claims abstract description 8
102000006635 beta-lactamase Human genes 0.000 claims abstract description 8
230000002401 inhibitory effect Effects 0.000 claims abstract description 6
230000000845 anti-microbial effect Effects 0.000 claims abstract description 4
-1 hydroxysulfonyloxy group Chemical group 0.000 claims description 533
239000000203 mixture Substances 0.000 claims description 189
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 98
229910052717 sulfur Inorganic materials 0.000 claims description 83
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 73
239000011593 sulfur Substances 0.000 claims description 73
125000000217 alkyl group Chemical group 0.000 claims description 72
125000000623 heterocyclic group Chemical group 0.000 claims description 63
125000004432 carbon atom Chemical group C* 0.000 claims description 58
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
125000006239 protecting group Chemical group 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 26
125000002252 acyl group Chemical group 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
125000004429 atom Chemical group 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
238000005917 acylation reaction Methods 0.000 claims description 7
125000004450 alkenylene group Chemical group 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
230000010933 acylation Effects 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 5
125000000539 amino acid group Chemical group 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
239000004599 antimicrobial Substances 0.000 claims description 3
125000005724 cycloalkenylene group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000005544 phthalimido group Chemical group 0.000 claims description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
BJBGFQIOZMZVFB-UHFFFAOYSA-N 3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-methylsulfanyl-4-oxoazetidine-1-sulfonic acid Chemical compound C=1SC(N)=NC=1C(=NOC)C(=O)NC1C(SC)N(S(O)(=O)=O)C1=O BJBGFQIOZMZVFB-UHFFFAOYSA-N 0.000 claims 1
GOFQXMKTAKIGQV-UHFFFAOYSA-N [3-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-4-oxo-1-sulfoazetidin-2-yl]-diazonioazanide Chemical compound C=1SC(N)=NC=1C(=NOC(C)(C)C(O)=O)C(=O)NC1C(N=[N+]=[N-])N(S(O)(=O)=O)C1=O GOFQXMKTAKIGQV-UHFFFAOYSA-N 0.000 claims 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 abstract description 20
150000002367 halogens Chemical class 0.000 abstract description 20
CDFGMYLBUSYTKQ-UHFFFAOYSA-N 2-oxoazetidine-1-sulfonic acid Chemical class OS(=O)(=O)N1CCC1=O CDFGMYLBUSYTKQ-UHFFFAOYSA-N 0.000 abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 427
239000000243 solution Substances 0.000 description 287
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 238
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 184
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 174
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 110
239000011734 sodium Substances 0.000 description 110
229910052708 sodium Inorganic materials 0.000 description 106
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 105
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 104
238000006243 chemical reaction Methods 0.000 description 90
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 86
239000011541 reaction mixture Substances 0.000 description 78
238000001816 cooling Methods 0.000 description 71
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
230000002829 reductive effect Effects 0.000 description 61
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
238000000746 purification Methods 0.000 description 47
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
238000003756 stirring Methods 0.000 description 45
239000000741 silica gel Substances 0.000 description 44
229910002027 silica gel Inorganic materials 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
239000000706 filtrate Substances 0.000 description 40
239000002904 solvent Substances 0.000 description 40
125000001424 substituent group Chemical group 0.000 description 39
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 37
229940086542 triethylamine Drugs 0.000 description 35
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
238000004587 chromatography analysis Methods 0.000 description 26
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 25
125000005518 carboxamido group Chemical group 0.000 description 23
229960005141 piperazine Drugs 0.000 description 23
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 20
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 18
239000002198 insoluble material Substances 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
238000001914 filtration Methods 0.000 description 17
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
125000004433 nitrogen atom Chemical group N* 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
239000003054 catalyst Substances 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 14
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
239000013078 crystal Substances 0.000 description 13
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 13
239000000725 suspension Substances 0.000 description 13
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
150000001539 azetidines Chemical class 0.000 description 11
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
229910052720 vanadium Inorganic materials 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
JVFVSVLCXCDOPD-UHFFFAOYSA-N 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC(=O)CCl)=N1 JVFVSVLCXCDOPD-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 9
125000004193 piperazinyl group Chemical group 0.000 description 9
239000000047 product Substances 0.000 description 9
125000004434 sulfur atom Chemical group 0.000 description 9
239000002585 base Substances 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000011347 resin Substances 0.000 description 8
229920005989 resin Polymers 0.000 description 8
125000001544 thienyl group Chemical group 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
125000004442 acylamino group Chemical group 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
150000007524 organic acids Chemical class 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
125000003831 tetrazolyl group Chemical group 0.000 description 7
125000000335 thiazolyl group Chemical group 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
125000000842 isoxazolyl group Chemical group 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
LSDJRBFOXKCGFY-UHFFFAOYSA-N 2-chloro-n-(1,3-thiazol-2-yl)acetamide Chemical compound ClCC(=O)NC1=NC=CS1 LSDJRBFOXKCGFY-UHFFFAOYSA-N 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 5
208000035473 Communicable disease Diseases 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
IJACXBZIXLEOPK-GGAORHGYSA-N [(2s,3s)-4-oxo-3-(tritylamino)azetidin-2-yl] acetate Chemical compound CC(=O)O[C@@H]1NC(=O)[C@H]1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IJACXBZIXLEOPK-GGAORHGYSA-N 0.000 description 5
125000003368 amide group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000003782 beta lactam antibiotic agent Substances 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 5
125000001786 isothiazolyl group Chemical group 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
125000006413 ring segment Chemical group 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
150000003871 sulfonates Chemical class 0.000 description 5
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
239000005051 trimethylchlorosilane Substances 0.000 description 5
239000002132 β-lactam antibiotic Substances 0.000 description 5
229940124586 β-lactam antibiotics Drugs 0.000 description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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229910052697 platinum Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
125000006410 propenylene group Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
OFOLIKLWAWXNKP-FYYLOGMGSA-N s-[(2r,3r)-4-oxo-3-(tritylamino)azetidin-2-yl] ethanethioate Chemical compound CC(=O)S[C@H]1NC(=O)[C@H]1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OFOLIKLWAWXNKP-FYYLOGMGSA-N 0.000 description 2
JHZPFFVDLSLXIE-SKDRFNHKSA-N s-[(2s,3r)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidin-2-yl] ethanethioate Chemical compound C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](SC(C)=O)NC1=O JHZPFFVDLSLXIE-SKDRFNHKSA-N 0.000 description 2
OFOLIKLWAWXNKP-GGAORHGYSA-N s-[(2s,3r)-4-oxo-3-(tritylamino)azetidin-2-yl] ethanethioate Chemical compound CC(=O)S[C@@H]1NC(=O)[C@H]1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OFOLIKLWAWXNKP-GGAORHGYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
QSBKJAXTFAUJLK-SOWVLMPRSA-M sodium;(2r,3r)-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-methylsulfanyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC)C(=O)N[C@H]1[C@@H](SC)N(S([O-])(=O)=O)C1=O QSBKJAXTFAUJLK-SOWVLMPRSA-M 0.000 description 2
BJGATCJANPGWPM-KATIXKQHSA-M sodium;(2s,3s)-2-acetyloxy-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](OC(C)=O)N(S([O-])(=O)=O)C1=O BJGATCJANPGWPM-KATIXKQHSA-M 0.000 description 2
QWFCHFVKSPSDST-GGMFNZDASA-M sodium;(3r,4s)-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-oxo-4-phenylsulfanylazetidine-1-sulfonate Chemical compound [Na+].S([C@H]1[C@@H](C(N1S([O-])(=O)=O)=O)NC(=O)C(=NOC)C=1N=C(N)SC=1)C1=CC=CC=C1 QWFCHFVKSPSDST-GGMFNZDASA-M 0.000 description 2
RJMGWIQBHGWLAP-CACIRBSMSA-M sodium;(3r,4s)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-2-oxo-4-phenylsulfanylazetidine-1-sulfonate Chemical compound [Na+].S([C@H]1[C@@H](C(N1S([O-])(=O)=O)=O)NC(=O)C(=NOC)C=1N=C(NC(=O)CCl)SC=1)C1=CC=CC=C1 RJMGWIQBHGWLAP-CACIRBSMSA-M 0.000 description 2
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VZPPRCBIZFWRNA-UHFFFAOYSA-N n-[tert-butyl(dimethyl)silyl]acetamide Chemical compound CC(=O)N[Si](C)(C)C(C)(C)C VZPPRCBIZFWRNA-UHFFFAOYSA-N 0.000 description 1
KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
125000004706 n-propylthio group Chemical group C(CC)S* 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
LHMRVAWTCGBZLK-UHFFFAOYSA-N n-trityl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)NC1=NC=CS1 LHMRVAWTCGBZLK-UHFFFAOYSA-N 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
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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
238000010534 nucleophilic substitution reaction Methods 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
210000000056 organ Anatomy 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=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
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
JHZPFFVDLSLXIE-BXKDBHETSA-N s-[(2r,3r)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidin-2-yl] ethanethioate Chemical compound C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@H]1[C@@H](SC(C)=O)NC1=O JHZPFFVDLSLXIE-BXKDBHETSA-N 0.000 description 1
QQYKTKGGSONTPM-DGCLKSJQSA-N s-[(2r,3r)-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-2-yl] ethanethioate Chemical compound CC(=O)S[C@H]1NC(=O)[C@H]1NC(=O)COC1=CC=CC=C1 QQYKTKGGSONTPM-DGCLKSJQSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002072 seryl group Chemical group 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
URUUZAKAOINDHO-KATIXKQHSA-M sodium (2S,3R)-3-[[2-methoxyimino-2-[2-(propanethioylamino)-1,3-thiazol-4-yl]acetyl]amino]-2-methylsulfanyl-4-oxoazetidine-1-sulfonate Chemical compound CS[C@H]1[C@@H](C(N1S(=O)(=O)[O-])=O)NC(C(=NOC)C=1N=C(SC1)NC(CC)=S)=O.[Na+] URUUZAKAOINDHO-KATIXKQHSA-M 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
DYIBOPLTEGTFOW-WYUVZMMLSA-M sodium;(2r,3r)-2-acetylsulfanyl-3-[[2-[2-[(2-aminoacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CN)=NC=1C(=NOC)C(=O)N[C@H]1[C@@H](SC(C)=O)N(S([O-])(=O)=O)C1=O DYIBOPLTEGTFOW-WYUVZMMLSA-M 0.000 description 1
DZQJCDDDRLYOQT-WYUVZMMLSA-M sodium;(2r,3r)-2-acetylsulfanyl-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@H]1[C@@H](SC(C)=O)N(S([O-])(=O)=O)C1=O DZQJCDDDRLYOQT-WYUVZMMLSA-M 0.000 description 1
NRCKDIXNUNHADR-FOKYBFFNSA-M sodium;(2r,3r)-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methoxy-2-methylsulfanyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC)C(=O)N[C@]1(OC)[C@@H](SC)N(S([O-])(=O)=O)C1=O NRCKDIXNUNHADR-FOKYBFFNSA-M 0.000 description 1
XVBGZSHDZSTBBM-JHQAJZDGSA-M sodium;(2r,3r)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-2-(1-methyltetrazol-5-yl)sulfanyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].S([C@@H]1[C@@H](C(N1S([O-])(=O)=O)=O)NC(=O)C(=NOC)C=1N=C(NC(=O)CCl)SC=1)C1=NN=NN1C XVBGZSHDZSTBBM-JHQAJZDGSA-M 0.000 description 1
MBDKFGLCBFGOFO-YLAFAASESA-M sodium;(2r,3s)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-3-methoxy-2-methylsulfanyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@@]1(OC)[C@@H](SC)N(S([O-])(=O)=O)C1=O MBDKFGLCBFGOFO-YLAFAASESA-M 0.000 description 1
OBCIYLNDANCOEV-QJVKKXMWSA-M sodium;(2s,3r)-2-acetylsulfanyl-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](SC(C)=O)N(S([O-])(=O)=O)C1=O OBCIYLNDANCOEV-QJVKKXMWSA-M 0.000 description 1
DZQJCDDDRLYOQT-KATIXKQHSA-M sodium;(2s,3r)-2-acetylsulfanyl-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](SC(C)=O)N(S([O-])(=O)=O)C1=O DZQJCDDDRLYOQT-KATIXKQHSA-M 0.000 description 1
QZECBQOSPGKQOT-NINOIYOQSA-M sodium;(2s,3r)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-2-methylsulfanyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](SC)N(S([O-])(=O)=O)C1=O QZECBQOSPGKQOT-NINOIYOQSA-M 0.000 description 1
FUFUKBTWLZAMNU-QJVKKXMWSA-M sodium;(2s,3s)-2-acetyloxy-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](OC(C)=O)N(S([O-])(=O)=O)C1=O FUFUKBTWLZAMNU-QJVKKXMWSA-M 0.000 description 1
OFQGDEQYNQPSRT-KATIXKQHSA-M sodium;(2s,3s)-2-acetyloxy-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-propan-2-yloxyiminoacetyl]amino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC(C)C)C(=O)N[C@H]1[C@H](OC(C)=O)N(S([O-])(=O)=O)C1=O OFQGDEQYNQPSRT-KATIXKQHSA-M 0.000 description 1
RVXCTCRRIIDFCS-YLAFAASESA-M sodium;(2s,3s)-2-acetyloxy-4-oxo-3-[(2-phenylacetyl)amino]azetidine-1-sulfonate Chemical compound [Na+].O=C1N(S([O-])(=O)=O)[C@@H](OC(=O)C)[C@@H]1NC(=O)CC1=CC=CC=C1 RVXCTCRRIIDFCS-YLAFAASESA-M 0.000 description 1
QTRSIVCYOFSXCH-OALZAMAHSA-M sodium;(3s,4r)-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-oxo-4-(2-phenylacetyl)oxyazetidine-1-sulfonate Chemical compound [Na+].O([C@@H]1[C@@H](C(N1S([O-])(=O)=O)=O)NC(=O)C(=NOC)C=1N=C(N)SC=1)C(=O)CC1=CC=CC=C1 QTRSIVCYOFSXCH-OALZAMAHSA-M 0.000 description 1
XSBVQRMSADUNFV-KQKCUOLZSA-M sodium;(3s,4r)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-2-oxo-4-(2-phenylacetyl)oxyazetidine-1-sulfonate Chemical compound [Na+].O([C@@H]1[C@@H](C(N1S([O-])(=O)=O)=O)NC(=O)C(=NOC)C=1N=C(NC(=O)CCl)SC=1)C(=O)CC1=CC=CC=C1 XSBVQRMSADUNFV-KQKCUOLZSA-M 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
GZBHDSXHZMBKRZ-UHFFFAOYSA-M sodium;methylsulfanylmethanethioate Chemical compound [Na+].CSC([S-])=O GZBHDSXHZMBKRZ-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
229960004932 sulbenicillin Drugs 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
FFIYCKGNJUHRHS-UHFFFAOYSA-N sulfurochloridic acid sulfur trioxide Chemical compound O=S(=O)=O.OS(Cl)(=O)=O FFIYCKGNJUHRHS-UHFFFAOYSA-N 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
FFXWYTYNILTGIL-UHFFFAOYSA-N tert-butyl(trimethyl)silane Chemical compound CC(C)(C)[Si](C)(C)C FFXWYTYNILTGIL-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000000464 thioxo group Chemical group S=* 0.000 description 1
125000001239 threonyl group Chemical group 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
125000002233 tyrosyl group Chemical group 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
125000002114 valyl group Chemical group 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1