CA1048016A - Antibiotiques - Google Patents

Antibiotiques

Info

Publication number: CA1048016A
Authority: CA; Canada
Prior art keywords: group; compound; formula; acid; solvates
Prior art date: 1973-08-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA293,802A

Other languages

English (en)

Inventor

Martin C. Cook

Gordon I. Gregory

Janice Bradshaw

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

Glaxo Laboratories Ltd

Original Assignee

Glaxo Laboratories Ltd

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

1973-08-21

Filing date

1977-12-23

Publication date

1979-02-06

1973-08-21 Priority claimed from GB3964573A external-priority patent/GB1453049A/en

1977-12-23 Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd

1979-02-06 Application granted granted Critical

1979-02-06 Publication of CA1048016A publication Critical patent/CA1048016A/fr

Status Expired legal-status Critical Current

Links

239000003242 anti bacterial agent Substances 0.000 title claims abstract description 16
229940088710 antibiotic agent Drugs 0.000 title abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 93
-1 carbamoyloxymethyl group Chemical group 0.000 claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 31
150000003839 salts Chemical class 0.000 claims abstract description 29
229930186147 Cephalosporin Natural products 0.000 claims abstract description 25
229940124587 cephalosporin Drugs 0.000 claims abstract description 25
231100000252 nontoxic Toxicity 0.000 claims abstract description 20
230000003000 nontoxic effect Effects 0.000 claims abstract description 20
150000002148 esters Chemical class 0.000 claims abstract description 19
239000012453 solvate Substances 0.000 claims abstract description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000002541 furyl group Chemical group 0.000 claims abstract description 7
125000001544 thienyl group Chemical group 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 5
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
230000003115 biocidal effect Effects 0.000 claims description 8
230000002252 carbamoylating effect Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
230000000903 blocking effect Effects 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 4
150000002513 isocyanates Chemical class 0.000 claims description 4
GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims description 3
TVPVPCIFAVVLAU-UHFFFAOYSA-N 2,2-dichloroacetyl isocyanate Chemical compound ClC(Cl)C(=O)N=C=O TVPVPCIFAVVLAU-UHFFFAOYSA-N 0.000 claims description 2
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
150000001718 carbodiimides Chemical class 0.000 claims description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 2
125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims 9
159000000000 sodium salts Chemical class 0.000 claims 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
238000009833 condensation Methods 0.000 claims 2
230000005494 condensation Effects 0.000 claims 2
ZYNJUSCNUGHTGU-MLGOLLRUSA-N (6R,7R)-3-(carbamoyloxymethyl)-7-[(2-methoxyimino-2-phenylacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(N)(=O)OCC=1CS[C@H]2N(C=1C(=O)O)C([C@H]2NC(C(C1=CC=CC=C1)=NOC)=O)=O ZYNJUSCNUGHTGU-MLGOLLRUSA-N 0.000 claims 1
IHTIDABULNQFAD-CXAGYDPISA-N (6r,7r)-3-(carbamoyloxymethyl)-7-[(2-ethoxyimino-2-phenylacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)C(=NOCC)C1=CC=CC=C1 IHTIDABULNQFAD-CXAGYDPISA-N 0.000 claims 1
VPDRXFZILNIZGZ-MLGOLLRUSA-N (6r,7r)-3-(carbamoyloxymethyl)-7-[[2-[(2-methylpropan-2-yl)oxyimino]-2-thiophen-2-ylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)C(=NOC(C)(C)C)C1=CC=CS1 VPDRXFZILNIZGZ-MLGOLLRUSA-N 0.000 claims 1
RNLMHQYFFBMMJW-DYESRHJHSA-N (6r,7r)-3-(carbamoyloxymethyl)-8-oxo-7-[(2-phenoxyimino-2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(O)=O)C(=O)C(C=1C=CC=CC=1)=NOC1=CC=CC=C1 RNLMHQYFFBMMJW-DYESRHJHSA-N 0.000 claims 1
150000001780 cephalosporins Chemical class 0.000 abstract description 21
238000005917 acylation reaction Methods 0.000 abstract description 7
230000010933 acylation Effects 0.000 abstract description 6
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
230000021235 carbamoylation Effects 0.000 abstract description 3
238000001727 in vivo Methods 0.000 abstract description 3
230000001747 exhibiting effect Effects 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
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 10
239000000047 product Substances 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000008064 anhydrides Chemical group 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 5
241000282414 Homo sapiens Species 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
ISFFCSPHFNWPST-UHFFFAOYSA-N 2-methoxyimino-2-phenylacetic acid Chemical compound CON=C(C(O)=O)C1=CC=CC=C1 ISFFCSPHFNWPST-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000012043 crude product Substances 0.000 description 4
XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical group OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
LWKSTSKGZABZPC-OXQOHEQNSA-N benzhydryl (6r,7r)-7-amino-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1[C@@H](C(N11)=O)N)CC(COC(N)=O)=C1C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 LWKSTSKGZABZPC-OXQOHEQNSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
244000005700 microbiome Species 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000002960 penicillins Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
OBSLWIKITOYASJ-YDEIVXIUSA-N (3r,4r,5s,6r)-6-(hydroxymethyl)-3-(methylamino)oxane-2,4,5-triol Chemical class CN[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OBSLWIKITOYASJ-YDEIVXIUSA-N 0.000 description 1
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 1
ZJIANJKJAAXAOC-CLZZGJSISA-N (6r,7r)-7-amino-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 ZJIANJKJAAXAOC-CLZZGJSISA-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
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
OBXGEEWBDPQYBP-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxyimino]-2-thiophen-2-ylacetic acid Chemical compound CC(C)(C)ON=C(C(O)=O)C1=CC=CS1 OBXGEEWBDPQYBP-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
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MALMHIVBMJBNGS-UHFFFAOYSA-N n,n'-dipropylmethanediimine Chemical group CCCN=C=NCCC MALMHIVBMJBNGS-UHFFFAOYSA-N 0.000 description 1
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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
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OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
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MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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125000006239 protecting group Chemical group 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000007017 scission Effects 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
HYOSZTGFBAAVSA-UHFFFAOYSA-M sodium 2-methoxyimino-2-thiophen-2-ylacetate Chemical compound [Na+].CON=C(C([O-])=O)C1=CC=CS1 HYOSZTGFBAAVSA-UHFFFAOYSA-M 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
AAMCVENDCXWDPJ-UHFFFAOYSA-N sulfanyl acetate Chemical class CC(=O)OS AAMCVENDCXWDPJ-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA293,802A 1973-08-21 1977-12-23 Antibiotiques Expired CA1048016A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3964573A GB1453049A (en)	1973-08-21	1973-08-21	Cephalosporing antibiotics
CA207,441A CA1057283A (fr)	1973-08-21	1974-08-20	Acide 3-carbamoyloxymethyl-7-(2-(fur-2-yl)-2-methoxyiminoacetamido) ceph-3-em-4-carboxylique

Publications (1)

Publication Number	Publication Date
CA1048016A true CA1048016A (fr)	1979-02-06

Family

ID=25667666

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,802A Expired CA1048016A (fr)	1973-08-21	1977-12-23	Antibiotiques

Country Status (1)

Country	Link
CA (1)	CA1048016A (fr)

1977
- 1977-12-23 CA CA293,802A patent/CA1048016A/fr not_active Expired

Publication	Publication Date	Title
US3974153A (en)	1976-08-10	7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids
US4464367A (en)	1984-08-07	Cephalosporin derivatives, process for preparation thereof and drugs containing said derivatives usable as antibiotics
US4168309A (en)	1979-09-18	Cephalosporins having a 7-(carboxy substituted α-etherified oximinoarylacetamido) group
CA1055016A (fr)	1979-05-22	ACIDES 7.alpha.-(ALCANE A CHAINE COURTE - OXY)-7.beta.-(2-ARYL-2-HYDROIMINOACETAMIDO) CEPH-3-EM-4-CARBOXYLIQUES
CA1057283A (fr)	1979-06-26	Acide 3-carbamoyloxymethyl-7-(2-(fur-2-yl)-2-methoxyiminoacetamido) ceph-3-em-4-carboxylique
US3966717A (en)	1976-06-29	7-β-Acylamido-3-carbamoyloxymethylceph-3-em-4-carboxylic acids and salts thereof
US3925368A (en)	1975-12-09	Acylureido substituted cephalosporins
US4138555A (en)	1979-02-06	(6R,7R)-7-[2-aryl-2-(etherified oximino)acetamido]-3-carbamoyloxymethylceph-3-em-4-carboxylic acid 1-oxides
US3719673A (en)	1973-03-06	Derivatives of 7-aminocephalosporanic acid
US4132789A (en)	1979-01-02	7-[2-(2-Imino-4-thiazolin-4-yl)-2-sulfoacetamido]cephalosporins and antibacterial compositions containing them
US4122259A (en)	1978-10-24	7β-[2-Aryl-2-(etherified oximino)acetamido]-3-N-substituted carbamoyloxymethylceph-3-em-4-carboxylic acids
CA1048016A (fr)	1979-02-06	Antibiotiques
CA1074297A (fr)	1980-03-25	Cephalosporines
US4060686A (en)	1977-11-29	Cephalosporins having a 7-(carboxy substituted α-etherified oximinoarylacetamido) group
US4018921A (en)	1977-04-19	Substituted phenylglycylcephalosporins
US4011215A (en)	1977-03-08	3-Chloroalkylcarbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acids and physiologically acceptable salts or oxides thereof
US4560683A (en)	1985-12-24	Cephalosporin antibiotics
US4162360A (en)	1979-07-24	3-Carbamoyloxymethyl-7-substituted oximino acetamido cephalosporanic acid derivatives
US4200746A (en)	1980-04-29	Cephalosporins
JPS5934715B2 (ja)	1984-08-24	７−置換アシルアミノ−３−置換−３−セフエム−４−カルボン酸類の製造法
CA1067067A (fr)	1979-11-27	L'acide 2-carbamoyloxymethyl-7-(2-carboxymethoxy-imino-2-(fur-2-yl) acetamido) ceph-3-em-4-carboxylique
US4067979A (en)	1978-01-10	Cephalosporins having an α-acyloxyacetic acid side chain
CA1070673A (fr)	1980-01-29	ACIDES 7.beta.-(2-ARYL-2-(OXIMINO ETHERIFIE) ACETAMIDO) CARBAMOYLOXYMETHYLCEPH (SUBSTITUE EN 3-N)-3-EM-4-CARBOXYLIQUES
GB1604724A (en)	1981-12-16	7-(2-aminothiazol-4-yl)-2-oxymino-acedamido)-cephem derivatives
CA1237427A (fr)	1988-05-31	Compose de cepheline