CA1049432A - Procede pour la preparation d'agents bactericides - Google Patents

Procede pour la preparation d'agents bactericides

Info

Publication number: CA1049432A
Authority: CA; Canada
Prior art keywords: alpha; amino; acid; esterase; process according
Prior art date: 1974-06-05
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

CA304,618A

Other languages

English (en)

Inventor

Abraham Weber

Daniel Bouzard

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.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

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.)

1974-06-05

Filing date

1978-06-01

Publication date

1979-02-27

1974-06-05 Priority claimed from GB2484874A external-priority patent/GB1476981A/en

1975-05-09 Priority claimed from CA226,671A external-priority patent/CA1049505A/fr

1978-06-01 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1978-06-01 Priority to CA304,618A priority Critical patent/CA1049432A/fr

1979-02-27 Application granted granted Critical

1979-02-27 Publication of CA1049432A publication Critical patent/CA1049432A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 43
238000002360 preparation method Methods 0.000 title abstract description 13
239000003242 anti bacterial agent Substances 0.000 title abstract description 5
239000002253 acid Substances 0.000 claims abstract description 37
238000004519 manufacturing process Methods 0.000 claims abstract description 7
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 27
108090000371 Esterases Proteins 0.000 claims description 24
239000000243 solution Substances 0.000 claims description 19
239000007864 aqueous solution Substances 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
210000002966 serum Anatomy 0.000 claims description 9
239000000872 buffer Substances 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 7
235000015099 wheat brans Nutrition 0.000 claims description 7
241000207199 Citrus Species 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 6
235000020971 citrus fruits Nutrition 0.000 claims description 6
241000209140 Triticum Species 0.000 claims description 4
235000021307 Triticum Nutrition 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
150000004684 trihydrates Chemical class 0.000 claims description 3
244000063299 Bacillus subtilis Species 0.000 claims description 2
235000014469 Bacillus subtilis Nutrition 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
238000002955 isolation Methods 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000008057 potassium phosphate buffer Substances 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 30
150000001875 compounds Chemical class 0.000 abstract description 25
-1 silyl ester Chemical class 0.000 abstract description 25
239000003795 chemical substances by application Substances 0.000 abstract description 10
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 abstract description 9
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 abstract description 9
229960003022 amoxicillin Drugs 0.000 abstract description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229960000723 ampicillin Drugs 0.000 description 9
238000005917 acylation reaction Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
239000012346 acetyl chloride Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 5
230000010933 acylation Effects 0.000 description 5
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 5
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000036765 blood level Effects 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
150000002960 penicillins Chemical class 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
244000144977 poultry Species 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
241000212342 Sium Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229910000160 potassium phosphate Inorganic materials 0.000 description 2
235000011009 potassium phosphates Nutrition 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
QVJWBJWRAPJXNM-UHFFFAOYSA-N (4-aminophenyl) acetate Chemical compound CC(=O)OC1=CC=C(N)C=C1 QVJWBJWRAPJXNM-UHFFFAOYSA-N 0.000 description 1
CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
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
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
RCEFMOGVOYEGJN-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one Chemical compound OC1=CC=CC=C1N1C(=O)NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CC1 RCEFMOGVOYEGJN-UHFFFAOYSA-N 0.000 description 1
LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
208000004232 Enteritis Diseases 0.000 description 1
VLVIJCDFVOHWCY-UHFFFAOYSA-N FC(C(=O)O)(F)F.[Sn] Chemical compound FC(C(=O)O)(F)F.[Sn] VLVIJCDFVOHWCY-UHFFFAOYSA-N 0.000 description 1
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 1
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
241001024304 Mino Species 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA304,618A 1974-06-05 1978-06-01 Procede pour la preparation d'agents bactericides Expired CA1049432A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA304,618A CA1049432A (fr)	1974-06-05	1978-06-01	Procede pour la preparation d'agents bactericides

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB2484874A GB1476981A (en)	1974-06-05	1974-06-05	Substituted penicillanic acids
GB5001674		1974-11-19
CA226,671A CA1049505A (fr)	1974-06-05	1975-05-09	Procede de preparation d'agents antibacteriens
CA304,618A CA1049432A (fr)	1974-06-05	1978-06-01	Procede pour la preparation d'agents bactericides

Publications (1)

Publication Number	Publication Date
CA1049432A true CA1049432A (fr)	1979-02-27

Family

ID=27425839

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA304,618A Expired CA1049432A (fr)	1974-06-05	1978-06-01	Procede pour la preparation d'agents bactericides

Country Status (1)

Country	Link
CA (1)	CA1049432A (fr)

1978
- 1978-06-01 CA CA304,618A patent/CA1049432A/fr not_active Expired

Publication	Publication Date	Title
US4012382A (en)	1977-03-15	α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives
US3687949A (en)	1972-08-29	Synthetic cephalosporins
JPS5858354B2 (ja)	1983-12-24	セフェム誘導体
JPH0257072B2 (fr)	1990-12-03
EP0399094A2 (fr)	1990-11-28	Procédé pour la préparation de ceftriaxone
US5574154A (en)	1996-11-12	Process for the preparation of cephalosporanic compounds
DK150201B (da)	1987-01-05	Alfa-azido-n-acyl-6-aminopenicillansyreester til anvendelse ved fremstilling af den tilsvarende alfa-aminoforbindelse
US4053360A (en)	1977-10-11	Enzymatic preparation of 6-D-(-)-α-amino-α-(p-hydroxyphenylacetamino)penicillin acid
JPS6226222A (ja)	1987-02-04	細菌性感染症治療剤
US3813388A (en)	1974-05-28	7-(d-(alpha-amino-alpha-phenyl-,2-thienyl-and 3-thienyl-acetamido))-3-(s-(2-methyl-1,2,3-triazole-4-yl)thiomethyl)-3-cephem-4-carboxylic acids
US3579506A (en)	1971-05-18	Alpha-aminoisothiazolylacetic acids and their penicillin and cephalosporin derivatives
RU2201933C2 (ru)	2003-04-10	Антибактериальные замещенные 7-ациламино-3-(метилгидразоно)метилцефалоспорины, способ их получения, фармацевтические композиции на их основе, промежуточные соединения и способ лечения заболеваний, вызванных микроорганизмами
US3850916A (en)	1974-11-26	7-amino-3-(s-(1,2,3-triazole-5-yl)-thiomethyl)-3-cephem-4-carboxylic acid and salts thereof
US3720664A (en)	1973-03-13	Alpha-ureidocyclohexadienylalkylene-penicillins
US4091215A (en)	1978-05-23	7-D-α-Amino-.alpha.-(p-acetoxyphenyl)acetamido-3-methyl-3-cephem-4-carboxylic acid
CA1056814A (fr)	1979-06-19	Derives de l'acide formyl-(p-acyloxyphenyl) acetamidocephalosporanique
EP0068403B1 (fr)	1986-08-13	Dérivé de céphalosporine
KR800001188B1 (ko)	1980-10-22	α-아미노벤질 페니실린 유도체의 제조방법
NZ566790A (en)	2011-03-31	Crystalline sodium salt of cephalosporin antibiotic
CA1056813A (fr)	1979-06-19	DERIVES DE L'ACIDE .alpha.-AMINO- (P-ACYLOXYPHENYL) ACETAMIDOCEPHALOSPORANIQUE
US3780088A (en)	1973-12-18	Alpha-ureidocyclohexadienylalkylene carboxylic acids
US3687948A (en)	1972-08-29	7-{8 D-(a-AMINO-a-PHENYLACETAMIDO){9 -3-(4-METHYL-1,3-OXAZOL-2-YLTHIOMETHYL-3-CEPHEM-4-CARBOXYLIC ACID AND SALTS THEREOF
US4180658A (en)	1979-12-25	7[-2-Alkoxyamino(acetamido)]cephalosporin derivatives
JPH0251435B2 (fr)	1990-11-07
US3342677A (en)	1967-09-19	Antibacterial compositions comprising alpha-aminothenylpenicillins