CH626624A5 - - Google Patents

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Info

Publication number: CH626624A5
Authority: CH; Switzerland
Prior art keywords: group; glycine; formula; amino; radical
Prior art date: 1973-10-12

Application number

CH1357774A

Other languages

German (de)

English (en)

Inventor

Burton Grant Christensen

Raymond Armond Firestone

Ronald William Ratcliffe

Original Assignee

Merck & Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-10-12

Filing date

1974-10-09

Publication date

1981-11-30

1974-10-09 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1981-11-30 Publication of CH626624A5 publication Critical patent/CH626624A5/de

Links

-1 amino, guanidino, protected phosphono Chemical group 0.000 claims description 370
238000000034 method Methods 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 39
229940124587 cephalosporin Drugs 0.000 claims description 37
229930186147 Cephalosporin Natural products 0.000 claims description 36
150000001780 cephalosporins Chemical class 0.000 claims description 32
150000003254 radicals Chemical group 0.000 claims description 28
230000008569 process Effects 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
150000004897 thiazines Chemical class 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
230000010933 acylation Effects 0.000 claims description 11
238000005917 acylation reaction Methods 0.000 claims description 11
230000000903 blocking effect Effects 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 9
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
150000002332 glycine derivatives Chemical class 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000005840 aryl radicals Chemical class 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000004149 thio group Chemical group *S* 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000005333 aroyloxy group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
238000006352 cycloaddition reaction Methods 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 144
238000006243 chemical reaction Methods 0.000 description 89
239000004471 Glycine Substances 0.000 description 78
239000002253 acid Substances 0.000 description 49
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
150000002148 esters Chemical class 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 19
125000001424 substituent group Chemical group 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
239000000543 intermediate Substances 0.000 description 18
239000000243 solution Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000002252 acyl group Chemical group 0.000 description 14
238000007796 conventional method Methods 0.000 description 14
150000004820 halides Chemical class 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 12
125000003277 amino group Chemical group 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 9
239000012346 acetyl chloride Substances 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
239000003242 anti bacterial agent Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
230000009467 reduction Effects 0.000 description 7
239000007858 starting material Substances 0.000 description 7
239000011701 zinc Substances 0.000 description 7
ZBLVJIXAKLJYGD-UHFFFAOYSA-N 2-diazenylacetic acid Chemical class OC(=O)CN=N ZBLVJIXAKLJYGD-UHFFFAOYSA-N 0.000 description 6
AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
229940088710 antibiotic agent Drugs 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
230000000269 nucleophilic effect Effects 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
125000004185 ester group Chemical group 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
230000007017 scission Effects 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 4
230000003213 activating effect Effects 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000005907 alkyl ester group Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 4
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 4
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 3
HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 3
VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 3
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
150000003934 aromatic aldehydes Chemical class 0.000 description 3
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
150000007522 mineralic 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
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000006257 total synthesis reaction Methods 0.000 description 3
125000006000 trichloroethyl group Chemical group 0.000 description 3
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
TUOCRSUVAZPVQU-UHFFFAOYSA-N 2-(1,2-thiazol-3-yl)acetyl chloride Chemical compound ClC(=O)CC=1C=CSN=1 TUOCRSUVAZPVQU-UHFFFAOYSA-N 0.000 description 2
QPMLAWSFAZDNFG-UHFFFAOYSA-N 2-(1,2-thiazol-4-yl)acetyl chloride Chemical compound ClC(=O)CC=1C=NSC=1 QPMLAWSFAZDNFG-UHFFFAOYSA-N 0.000 description 2
IQMWIJHCHHCTSS-UHFFFAOYSA-N 2-(1,2-thiazol-5-yl)acetyl chloride Chemical compound ClC(=O)CC1=CC=NS1 IQMWIJHCHHCTSS-UHFFFAOYSA-N 0.000 description 2
DFKQZCVLSJIRES-UHFFFAOYSA-N 2-(3-bromophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=CC(Br)=C1 DFKQZCVLSJIRES-UHFFFAOYSA-N 0.000 description 2
WVBOMHXZSITEAX-UHFFFAOYSA-N 2-(3-methyl-1,2-thiazol-4-yl)acetyl chloride Chemical compound CC1=NSC=C1CC(Cl)=O WVBOMHXZSITEAX-UHFFFAOYSA-N 0.000 description 2
ZYWBPOYXCATUHB-UHFFFAOYSA-N 2-(4-methoxy-1,2-thiazol-3-yl)acetyl chloride Chemical compound COC1=CSN=C1CC(Cl)=O ZYWBPOYXCATUHB-UHFFFAOYSA-N 0.000 description 2
RMCPATRJLNBKEZ-UHFFFAOYSA-N 2-(4-methylthiophen-2-yl)acetyl chloride Chemical compound CC1=CSC(CC(Cl)=O)=C1 RMCPATRJLNBKEZ-UHFFFAOYSA-N 0.000 description 2
VRBZTHJEGQLBPJ-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)S1 VRBZTHJEGQLBPJ-UHFFFAOYSA-N 0.000 description 2
XMIKOOVFAIOIHP-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)acetyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CC(Cl)=O)O1 XMIKOOVFAIOIHP-UHFFFAOYSA-N 0.000 description 2
KZDHMONYYLJPFO-UHFFFAOYSA-N 2-(furan-3-yl)acetyl chloride Chemical compound ClC(=O)CC=1C=COC=1 KZDHMONYYLJPFO-UHFFFAOYSA-N 0.000 description 2
LISBBJOOWFTPHE-UHFFFAOYSA-N 2-(thiophen-2-ylamino)acetyl chloride Chemical compound ClC(=O)CNC1=CC=CS1 LISBBJOOWFTPHE-UHFFFAOYSA-N 0.000 description 2
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
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241000607142 Salmonella Species 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000005035 acylthio group Chemical group 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
MMCPOSDMTGQNKG-UJZMCJRSSA-N aniline;hydrochloride Chemical compound Cl.N[14C]1=[14CH][14CH]=[14CH][14CH]=[14CH]1 MMCPOSDMTGQNKG-UJZMCJRSSA-N 0.000 description 1
235000019730 animal feed additive Nutrition 0.000 description 1
229940124350 antibacterial drug Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000002102 aryl alkyloxo group Chemical group 0.000 description 1
125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical group [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 1
239000003899 bactericide agent Substances 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
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
235000010633 broth Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
150000001781 cephams Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
TVMUHOAONWHJBV-UHFFFAOYSA-N dehydroglycine Chemical compound OC(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-N 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005868 electrolysis reaction Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
230000004720 fertilization Effects 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000009920 food preservation Methods 0.000 description 1
150000002333 glycines Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
KJNZDMKPARNMTH-UHFFFAOYSA-N methyl phenyl sulfate Chemical compound COS(=O)(=O)OC1=CC=CC=C1 KJNZDMKPARNMTH-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical group COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
RXYWJVBHDBOSNT-UHFFFAOYSA-N n-(hydroxymethyl)pyridine-4-carboxamide Chemical compound OCNC(=O)C1=CC=NC=C1 RXYWJVBHDBOSNT-UHFFFAOYSA-N 0.000 description 1
BIAGWQYHUNVQCD-UHFFFAOYSA-N n-cyanopyridine-4-carboxamide Chemical compound N#CNC(=O)C1=CC=NC=C1 BIAGWQYHUNVQCD-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004002 naphthaldehydes Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 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
239000003973 paint Substances 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical group Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000002989 phenols Chemical class 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
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
JHXPCSYIECUNMQ-UHFFFAOYSA-M potassium methanedithioate Chemical compound [K+].[S-]C=S JHXPCSYIECUNMQ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000039 preparative column chromatography Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
VFQXVTODMYMSMJ-UHFFFAOYSA-O pyridin-1-ium-4-carboxamide Chemical compound NC(=O)C1=CC=[NH+]C=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-O 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
150000004819 silanols Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 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
QZNVHCWSDFYKTO-UHFFFAOYSA-M sodium;methanedithioate Chemical compound [Na+].[S-]C=S QZNVHCWSDFYKTO-UHFFFAOYSA-M 0.000 description 1
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
IBNGNCXRTRDHCK-UHFFFAOYSA-N sulfuric acid trifluoroborane Chemical compound FB(F)F.OS(O)(=O)=O IBNGNCXRTRDHCK-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
YIHJHCFUGYYAKW-UHFFFAOYSA-O triethylazanium;azide Chemical compound [N-]=[N+]=[N-].CC[NH+](CC)CC YIHJHCFUGYYAKW-UHFFFAOYSA-O 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

CH1357774A 1973-10-12 1974-10-09 CH626624A5 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US40600073A	1973-10-12	1973-10-12

Publications (1)

Publication Number	Publication Date
CH626624A5 true CH626624A5 (pl)	1981-11-30

Family

ID=23606116

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1357774A CH626624A5 (pl)	1973-10-12	1974-10-09

Country Status (9)

Country	Link
US (1)	US4086423A (pl)
JP (1)	JPS5064293A (pl)
CH (1)	CH626624A5 (pl)
DE (1)	DE2448582A1 (pl)
DK (1)	DK503774A (pl)
FR (1)	FR2247466B1 (pl)
GB (1)	GB1457144A (pl)
NL (1)	NL7412541A (pl)
SE (1)	SE7411978L (pl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1583543A (en) *	1976-06-26	1981-01-28	Beecham Group Ltd	7-ketenimino-cephalosporins and their use as intermediates
US4165429A (en) *	1976-06-28	1979-08-21	Yamanouchi Pharmaceutical Co., Ltd.	7α-METHOXY-CEPHALOSPORANIC ACID DERIVATIVES
US4973456A (en) *	1988-10-24	1990-11-27	Air Products And Chemicals, Inc.	Use of salt hydrates as reversible absorbents of acid gases
IL99898A (en) *	1990-11-09	1996-10-31	Eisai Co Ltd	7-Acyl-3-substituted carbamoyloxy cephem compounds their preparation and antibacterial compositions containing them
US6045770A (en) *	1993-03-12	2000-04-04	Wilhelm Environmental Technologies	Sulfur dioxide generation using granulated or emulsoid sulfur feedstock
EP2218243B1 (en) *	2007-12-04	2018-08-01	Telefonaktiebolaget LM Ericsson (publ)	A method of reducing size of presence messages

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6515209A (pl) *	1965-11-24	1967-05-25
US3987040A (en) *	1971-11-22	1976-10-19	Merck & Co., Inc.	3-substituted methyl-7-acylamino-7-methoxy-2-cephem-4-carboxylic acid and its esters
US3962224A (en) *	1972-10-10	1976-06-08	Merck & Co., Inc.	Cephalosporin compounds

1974
- 1974-09-23 NL NL7412541A patent/NL7412541A/xx not_active Application Discontinuation
- 1974-09-24 SE SE7411978A patent/SE7411978L/xx unknown
- 1974-09-25 DK DK503774A patent/DK503774A/da unknown
- 1974-10-03 GB GB4295874A patent/GB1457144A/en not_active Expired
- 1974-10-09 CH CH1357774A patent/CH626624A5/de not_active IP Right Cessation
- 1974-10-10 FR FR7434094A patent/FR2247466B1/fr not_active Expired
- 1974-10-11 DE DE19742448582 patent/DE2448582A1/de not_active Withdrawn
- 1974-10-12 JP JP49117605A patent/JPS5064293A/ja active Pending
1975
- 1975-10-21 US US05/624,369 patent/US4086423A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE2448582A1 (de)	1975-06-19
SE7411978L (sv)	1975-05-07
JPS5064293A (pl)	1975-05-31
NL7412541A (nl)	1975-04-15
FR2247466A1 (pl)	1975-05-09
GB1457144A (en)	1976-12-01
DK503774A (pl)	1975-06-09
US4086423A (en)	1978-04-25
FR2247466B1 (pl)	1979-02-16

Publication	Publication Date	Title
CH624119A5 (pl)	1981-07-15
DE2355209A1 (de)	1974-05-16	Neue antibiotica
DE2129675A1 (de)	1971-12-23	Antibiotika und Verfahren zu deren Herstellung
DE2356388A1 (de)	1974-05-22	Cephalosporine und verfahren zu ihrer herstellung
DE2151567C2 (de)	1982-11-04	7-Amino-ceph-3-em-4-carbonsäure-Verbindungen und Verfahren zu ihrer Herstellung
EP0009008A2 (de)	1980-03-19	Cephalosporinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
EP0002765A1 (de)	1979-07-11	Cephalosporinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Präparate sowie deren Herstellung
DE3512225A1 (de)	1985-10-17	Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel
DE69132580T2 (de)	2001-10-25	7-Acyl-3-(substituierte carbamoyloxy) Cephem Verbindungen, Verfahren zu ihrer Herstellung und Anwendung
CH626624A5 (pl)	1981-11-30
CH645116A5 (de)	1984-09-14	Cephem-verbindungen, verfahren zu ihrer herstellung und sie enthaltende antibakterielle pharmazeutische mittel.
DE2223667C2 (de)	1984-02-23	Verfahren zur Herstellung von 8-Oxo-5-thia-1-azabicyclo-[4,2,0]oct-2-en- oder -3-en-Verbindungen
DE2364192A1 (de)	1974-06-27	Verfahren zur herstellung antibakterieller mittel
DE2636962C2 (pl)	1987-07-02
DE2700271A1 (de)	1977-07-14	Thienopyridinderivate
DE2633005A1 (de)	1977-02-10	Cephem- und penamverbindungen und verfahren zu ihrer herstellung
DE3851449T2 (de)	1995-03-16	Cephalosporinderivate, Verfahren zu ihrer Herstellung und antibakterielle Mittel.
CH625525A5 (pl)	1981-09-30
DE2451492A1 (de)	1975-05-15	2-oxo-1-pyridinyl-penicillin- und -cephalosporin-derivate
DE2600880A1 (de)	1977-07-21	Neue cephalosporine, verfahren zur herstellung derselben und mittel mit einem gehalt derselben
DE2702552A1 (de)	1977-07-28	7alpha-methoxy-cephalosporine und verfahren zur herstellung derselben
DE2559932C2 (de)	1983-04-21	Cephalosporine, Verfahren zur Herstellung derselben und Mittel mit einem Gehalt derselben
EP0015240A1 (de)	1980-09-03	Azacyclyl (thio) ureidoacetyl-Verbindungen und Verfahren zu ihrer Herstellung
DE2818025A1 (de)	1978-11-09	Verfahren zur herstellung von cephemverbindungen
CH605999A5 (en)	1978-10-13	3-Thio-7-amino-3- and-2-cephem-4-carboxylic acids

Legal Events

Date	Code	Title	Description
1985-06-28	PL	Patent ceased
2024-10-31	PL	Patent ceased