CH629500A5 - Processes for preparing novel cephalosporins. - Google Patents

Processes for preparing novel cephalosporins. Download PDF

Info

Publication number: CH629500A5
Authority: CH; Switzerland
Prior art keywords: sodium; formula; potassium; acid; solution
Prior art date: 1975-10-06

Application number

CH1259376A

Other languages

German (de)

English (en)

Inventor

Murray Arthur Kaplan

William J Gottstein

Alphonse Peter Granatek

Original Assignee

Bristol Myers 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.)

1975-10-06

Filing date

1976-10-05

Publication date

1982-04-30

1976-01-30 Priority claimed from US05/653,999 external-priority patent/US4026888A/en

1976-02-02 Priority claimed from US05/654,314 external-priority patent/US4061862A/en

1976-10-05 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1982-04-30 Publication of CH629500A5 publication Critical patent/CH629500A5/de

Links

238000000034 method Methods 0.000 title claims description 59
150000001780 cephalosporins Chemical class 0.000 title claims description 57
229940124587 cephalosporin Drugs 0.000 title claims description 55
229930186147 Cephalosporin Natural products 0.000 title claims description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 107
-1 5-sulfo-2-furyl Chemical group 0.000 claims description 72
150000001875 compounds Chemical class 0.000 claims description 72
229910001868 water Inorganic materials 0.000 claims description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 54
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 50
239000011734 sodium Chemical group 0.000 claims description 43
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 38
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 36
229910052708 sodium Inorganic materials 0.000 claims description 35
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 34
150000001299 aldehydes Chemical class 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 31
239000012453 solvate Substances 0.000 claims description 25
OKTJSMMVPCPJKN-UHFFFAOYSA-N activated carbon Substances [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
229910052783 alkali metal Inorganic materials 0.000 claims description 21
239000002585 base Substances 0.000 claims description 21
239000007795 chemical reaction product Substances 0.000 claims description 21
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 21
239000000047 product Substances 0.000 claims description 21
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052700 potassium Chemical group 0.000 claims description 19
239000011591 potassium Chemical group 0.000 claims description 19
239000003960 organic solvent Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
239000000725 suspension Substances 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 11
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 10
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 9
238000001556 precipitation Methods 0.000 claims description 9
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
230000002378 acidificating effect Effects 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
238000001914 filtration Methods 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 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 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
NASRDENTZCCAPN-UHFFFAOYSA-N OC([Na])=O Chemical compound OC([Na])=O NASRDENTZCCAPN-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 1
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 81
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239000007787 solid Substances 0.000 description 22
238000003756 stirring Methods 0.000 description 18
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239000007858 starting material Substances 0.000 description 17
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230000036765 blood level Effects 0.000 description 15
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239000000706 filtrate Substances 0.000 description 12
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
125000004122 cyclic group Chemical group 0.000 description 10
239000008363 phosphate buffer Substances 0.000 description 10
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
URIMPWMBVPNFDM-UHFFFAOYSA-N 5-formylfuran-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)O1 URIMPWMBVPNFDM-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
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239000002244 precipitate Substances 0.000 description 8
SBUCDZYLTRYMFG-PBFPGSCMSA-N (6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](N)C=3C=CC(O)=CC=3)[C@H]2SC1 SBUCDZYLTRYMFG-PBFPGSCMSA-N 0.000 description 7
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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235000002918 Fraxinus excelsior Nutrition 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000004811 liquid chromatography Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
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DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
241000219470 Mirabilis Species 0.000 description 5
238000004166 bioassay Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
150000004683 dihydrates Chemical class 0.000 description 5
238000010790 dilution Methods 0.000 description 5
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125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
239000002207 metabolite Substances 0.000 description 5
OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
239000002002 slurry Substances 0.000 description 5
ANWMNLAAFDCKMT-UHFFFAOYSA-N 2-(2-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC=C1C=O ANWMNLAAFDCKMT-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
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239000007859 condensation product Substances 0.000 description 4
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230000000694 effects Effects 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
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159000000001 potassium salts Chemical class 0.000 description 4
125000003396 thiol group Chemical class [H]S* 0.000 description 4
150000003952 β-lactams Chemical class 0.000 description 4
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241000283690 Bos taurus Species 0.000 description 3
241000282412 Homo Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
244000038458 Nepenthes mirabilis Species 0.000 description 3
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150000007513 acids Chemical class 0.000 description 3
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229940106164 cephalexin Drugs 0.000 description 3
AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 3
239000000356 contaminant Substances 0.000 description 3
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ZTJAVDOZUQPVAV-UHFFFAOYSA-M sodium;5-formylfuran-2-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=O)O1 ZTJAVDOZUQPVAV-UHFFFAOYSA-M 0.000 description 3
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206010037660 Pyrexia Diseases 0.000 description 2
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YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 2
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FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
125000003460 beta-lactamyl group Chemical group 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 1
229950004030 cefaloglycin Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000008957 cocaer Nutrition 0.000 description 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
MKYNHKOAYQRSBD-UHFFFAOYSA-N dioxouranium;nitric acid Chemical compound O=[U]=O.O[N+]([O-])=O.O[N+]([O-])=O MKYNHKOAYQRSBD-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940095399 enema Drugs 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006052 feed supplement Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
OKSYMZKKVJYKKJ-UHFFFAOYSA-N furan-2-sulfonic acid Chemical group OS(=O)(=O)C1=CC=CO1 OKSYMZKKVJYKKJ-UHFFFAOYSA-N 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960001269 glycine hydrochloride Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
238000001139 pH measurement Methods 0.000 description 1
ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
238000011002 quantification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/58—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with a nitrogen atom, which is a member of a hetero ring, attached in position 7

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1259376A 1975-10-06 1976-10-05 Processes for preparing novel cephalosporins. CH629500A5 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US62000575A	1975-10-06	1975-10-06
US62230675A	1975-10-10	1975-10-10
US64031775A	1975-12-12	1975-12-12
US05/653,999 US4026888A (en)	1975-10-10	1976-01-30	Certain derivatives of particular 3-thiolated cephalosporins
US05/654,314 US4061862A (en)	1975-10-06	1976-02-02	Derivatives of 7-(cyclized)phenylglycyl-3-triazolo-thio methyl cephalosporin

Publications (1)

Publication Number	Publication Date
CH629500A5 true CH629500A5 (en)	1982-04-30

Family

ID=27542000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1259376A CH629500A5 (en)	1975-10-06	1976-10-05	Processes for preparing novel cephalosporins.

Country Status (17)

Country	Link
JP (1)	JPS6052718B2 (da)
AU (1)	AU511344B2 (da)
BE (1)	BE846890A (da)
CA (1)	CA1113927A (da)
CH (1)	CH629500A5 (da)
CY (1)	CY1121A (da)
DE (1)	DE2645144C2 (da)
DK (2)	DK158673C (da)
FR (1)	FR2326926A1 (da)
GB (1)	GB1521419A (da)
HK (1)	HK41281A (da)
IE (1)	IE43666B1 (da)
KE (1)	KE3154A (da)
LU (1)	LU75935A1 (da)
NL (1)	NL189670C (da)
SE (1)	SE434952B (da)
YU (1)	YU40287B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54112892A (en) *	1978-02-23	1979-09-04	Shionogi & Co Ltd	Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acid
JPS54115354A (en) *	1978-02-27	1979-09-07	Chugai Pharmaceut Co Ltd	Biphenylylglycine derivative
WO2019168164A1 (ja) *	2018-03-02	2019-09-06	国立大学法人大阪大学	タンパク質及び／又はペプチド修飾用分子

1976
- 1976-09-30 AU AU18245/76A patent/AU511344B2/en not_active Expired
- 1976-10-01 BE BE171201A patent/BE846890A/xx not_active IP Right Cessation
- 1976-10-04 YU YU2431/76A patent/YU40287B/xx unknown
- 1976-10-04 DK DK446576A patent/DK158673C/da not_active IP Right Cessation
- 1976-10-04 LU LU75935A patent/LU75935A1/xx unknown
- 1976-10-04 SE SE7610989A patent/SE434952B/xx not_active IP Right Cessation
- 1976-10-04 FR FR7629825A patent/FR2326926A1/fr active Granted
- 1976-10-05 CY CY1121A patent/CY1121A/xx unknown
- 1976-10-05 IE IE2192/76A patent/IE43666B1/en not_active IP Right Cessation
- 1976-10-05 GB GB41293/76A patent/GB1521419A/en not_active Expired
- 1976-10-05 CH CH1259376A patent/CH629500A5/de not_active IP Right Cessation
- 1976-10-05 CA CA262,753A patent/CA1113927A/en not_active Expired
- 1976-10-06 JP JP51119513A patent/JPS6052718B2/ja not_active Expired
- 1976-10-06 NL NLAANVRAGE7611026,A patent/NL189670C/xx not_active IP Right Cessation
- 1976-10-06 DE DE2645144A patent/DE2645144C2/de not_active Expired
1981
- 1981-08-20 HK HK412/81A patent/HK41281A/xx unknown
- 1981-08-25 KE KE3154A patent/KE3154A/xx unknown
1988
- 1988-04-12 DK DK200488A patent/DK164225C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
KE3154A (en)	1981-09-18
DK158673C (da)	1991-01-14
YU243176A (en)	1982-06-30
IE43666B1 (en)	1981-04-22
SE7610989L (sv)	1977-04-07
AU511344B2 (en)	1980-08-14
DE2645144A1 (de)	1977-04-14
JPS6052718B2 (ja)	1985-11-20
AU1824576A (en)	1978-04-06
SE434952B (sv)	1984-08-27
DK446576A (da)	1977-04-07
DE2645144C2 (de)	1986-11-27
GB1521419A (en)	1978-08-16
FR2326926A1 (fr)	1977-05-06
CY1121A (en)	1981-12-04
DK200488A (da)	1988-04-12
FR2326926B1 (da)	1980-07-11
NL189670B (nl)	1993-01-18
IE43666L (en)	1977-04-06
DK200488D0 (da)	1988-04-12
DK158673B (da)	1990-07-02
HK41281A (en)	1981-08-28
JPS5246094A (en)	1977-04-12
NL7611026A (nl)	1977-04-12
DK164225B (da)	1992-05-25
LU75935A1 (da)	1977-05-25
BE846890A (fr)	1977-04-01
CA1113927A (en)	1981-12-08
YU40287B (en)	1985-12-31
NL189670C (nl)	1993-06-16
DK164225C (da)	1992-10-19

Legal Events

Date	Code	Title	Description
1994-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2760123C2 (de)	1986-04-30	7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE2332878C2 (de)	1983-07-28	Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen
DE2018600B2 (de)	1975-01-02	3-Thiadiazolylmercaptomethyl- und -Tetrazolylmercaptomethylcephalosporine und Verfahren zu ihrer Herstellung
DE1670625B2 (de)	1974-10-24	7-alpha-Aminobenzyl-3-methylcephalosporinanaloge und ihre Herstellung
DE2052962A1 (da)	1971-05-06
DE2700552C2 (de)	1985-02-28	Derivate der 7-Aminocephalosporansäure, ihre Herstellung und pharmazeutische Mittel
EP0280157B1 (de)	1995-09-27	Kristallisierte Cephem-Säureadditionssalze und Verfahren zu ihrer Herstellung
CH657857A5 (de)	1986-09-30	In 7-stellung substituierte 3-vinyl-3-cephemverbindungen und verfahren zur herstellung derselben.
CH629500A5 (en)	1982-04-30	Processes for preparing novel cephalosporins.
DE2738711A1 (de)	1978-03-02	Cephalosporinderivate
DE1795151C3 (de)	1975-04-24	7- eckige Klammer auf D-alpha-Amino-(3-actamidophenylacetamido) eckige Klammer zu -cephalosporansäure
DE3887691T2 (de)	1994-06-09	Cephalosporin-antibiotika.
DE3035259C2 (de)	1986-03-13	Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DD261163A5 (de)	1988-10-19	Verfahren zur reinigung von cephalosporin-antibiotika
DE2806226A1 (de)	1978-08-24	Oximderivate der 3-thiadiazolylthiomethyl-7-aminothiazolyl-acetamido- cephalosporansaeure, ihr herstellungsverfahren sowie pharmazeutische zusammensetzungen
DE2318986A1 (de)	1973-12-06	Neue penicilline
DE2234280B2 (de)	1979-03-29	Cephalosporinverbindungen und Verfahren zu deren Herstellung
US4091213A (en)	1978-05-23	7-Cyclizedamino-3-heterothiomethyl cephalosporin derivatives
DE2403512C2 (de)	1983-01-13	6-[D-2-Phenyl-2-(4-pyridoimidoylaminoacetamido) acetamido]-penicillansäure und deren pharmazeutisch verträgliche Salze sowie Verfahren zu deren Herstellung
DE2454109A1 (de)	1975-05-15	Neue cephalosporinderivate, deren herstellung und diese enthaltende zusammensetzungen
DE1670788C3 (de)	1979-03-29	3-Dithiocarbamat-Derivate von Cephalosporinen und Verfahren zu ihrer Herstellung
DE2927683A1 (de)	1980-01-31	Neue cephalosporinderivate, verfahren zu ihrer herstellung sowie arzneimittel
DE2632924C2 (de)	1983-05-26	1-Hydroxy-1-methyl-1,3-dihydrofuro[3,4-b]chinoxalin-4,9-dioxid
US4035381A (en)	1977-07-12	Antibacterial agents
DE1445701A1 (de)	1969-08-28	Verfahren zur Herstellung von Cephalosporin-Verbindungen