NO134219B - - Google Patents

Download PDF

Info

Publication number: NO134219B
Authority: NO; Norway
Prior art keywords: antibiotic; medium; growth; streptomyces; fermentation
Prior art date: 1970-03-13

Application number

NO932/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO134219C (nl

Inventor

E O Stapley

J M Mata

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.)

1970-03-13

Filing date

1971-03-12

Publication date

1976-05-24

1971-02-16 Priority claimed from US05/115,779 external-priority patent/US4302578A/en

1971-03-12 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1972-06-16 Priority to NO214572A priority Critical patent/NO134952C/no

1976-05-24 Publication of NO134219B publication Critical patent/NO134219B/no

1976-09-01 Publication of NO134219C publication Critical patent/NO134219C/no

Links

238000000034 method Methods 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 26
241000187390 Amycolatopsis lactamdurans Species 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 16
235000015097 nutrients Nutrition 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 12
244000005700 microbiome Species 0.000 claims description 12
241000187747 Streptomyces Species 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 11
239000002609 medium Substances 0.000 description 37
230000003115 biocidal effect Effects 0.000 description 32
238000000855 fermentation Methods 0.000 description 32
230000004151 fermentation Effects 0.000 description 32
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 28
230000012010 growth Effects 0.000 description 25
239000000047 product Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 23
229920001817 Agar Polymers 0.000 description 21
239000008272 agar Substances 0.000 description 21
239000000049 pigment Substances 0.000 description 21
230000009105 vegetative growth Effects 0.000 description 21
239000006071 cream Substances 0.000 description 19
230000000694 effects Effects 0.000 description 19
-1 D-5-amino-5-carboxyvaleramido group Chemical group 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
238000011534 incubation Methods 0.000 description 15
239000007788 liquid Substances 0.000 description 15
239000002054 inoculum Substances 0.000 description 14
238000012360 testing method Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
239000000203 mixture Substances 0.000 description 13
229940041514 candida albicans extract Drugs 0.000 description 12
239000012138 yeast extract Substances 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
241001453268 Comamonas terrigena Species 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
241000894007 species Species 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
230000002779 inactivation Effects 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
241000588772 Morganella morganii Species 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
238000001727 in vivo Methods 0.000 description 7
241000187438 Streptomyces fradiae Species 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
208000015181 infectious disease Diseases 0.000 description 6
239000006916 nutrient agar Substances 0.000 description 6
229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
230000008569 process Effects 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
238000001179 sorption measurement Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
241000186361 Actinobacteria <class> Species 0.000 description 5
241000588813 Alcaligenes faecalis Species 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
241000607142 Salmonella Species 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
229940088710 antibiotic agent Drugs 0.000 description 5
230000001580 bacterial effect Effects 0.000 description 5
229960000603 cefalotin Drugs 0.000 description 5
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 5
238000000338 in vitro Methods 0.000 description 5
239000013587 production medium Substances 0.000 description 5
239000006228 supernatant Substances 0.000 description 5
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
108010087702 Penicillinase Proteins 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
238000011835 investigation Methods 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229950009506 penicillinase Drugs 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
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 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
244000144730 Amygdalus persica Species 0.000 description 3
235000014469 Bacillus subtilis Nutrition 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
108020004256 Beta-lactamase Proteins 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000192125 Firmicutes Species 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000588770 Proteus mirabilis Species 0.000 description 3
241000588767 Proteus vulgaris Species 0.000 description 3
235000006040 Prunus persica var persica Nutrition 0.000 description 3
241000424942 Streptomyces clavuligerus ATCC 27064 Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229940005347 alcaligenes faecalis Drugs 0.000 description 3
150000003973 alkyl amines Chemical class 0.000 description 3
239000003957 anion exchange resin Substances 0.000 description 3
150000003974 aralkylamines Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
239000008121 dextrose Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
229940007042 proteus vulgaris Drugs 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
230000028070 sporulation Effects 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
241000588986 Alcaligenes Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
229920002307 Dextran Polymers 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
206010034133 Pathogen resistance Diseases 0.000 description 2
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 2
241000364057 Peoria Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
241000185992 Rhizobium viscosum Species 0.000 description 2
125000005263 alkylenediamine group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
230000035425 carbon utilization Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 2
229960003866 cefaloridine Drugs 0.000 description 2
210000002421 cell wall Anatomy 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
150000001470 diamides Chemical class 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
230000007515 enzymatic degradation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000005187 foaming Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Chemical class 0.000 description 2
235000013379 molasses Nutrition 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
230000000877 morphologic effect Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
238000012827 research and development Methods 0.000 description 2
235000020183 skimmed milk Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
230000001131 transforming effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
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 description 1
WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
240000002470 Amphicarpaea bracteata Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000588779 Bordetella bronchiseptica Species 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
244000132059 Carica parviflora Species 0.000 description 1
235000014653 Carica parviflora Nutrition 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-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
239000005909 Kieselgur Substances 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000191938 Micrococcus luteus Species 0.000 description 1
241000187708 Micromonospora Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
108010058846 Ovalbumin Proteins 0.000 description 1
241000606856 Pasteurella multocida Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
102000007327 Protamines Human genes 0.000 description 1
108010007568 Protamines Proteins 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
208000035193 Ring chromosome 10 syndrome Diseases 0.000 description 1
241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000192085 Staphylococcus gallinarum Species 0.000 description 1
241000193998 Streptococcus pneumoniae Species 0.000 description 1
241000187433 Streptomyces clavuligerus Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
241000203640 Thermomonospora Species 0.000 description 1
241000567019 Xanthomonas vesicatoria Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002156 adsorbate Substances 0.000 description 1
238000010564 aerobic fermentation Methods 0.000 description 1
238000012459 agar diffusion assay Methods 0.000 description 1
238000013019 agitation Methods 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
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 1
229960000723 ampicillin Drugs 0.000 description 1
239000012984 antibiotic solution Substances 0.000 description 1
238000011203 antimicrobial therapy Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
239000011324 bead Substances 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
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
238000004820 blood count Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
HDRTWMBOUSPQON-ODZAUARKSA-L calcium;(z)-but-2-enedioate Chemical compound [Ca+2].[O-]C(=O)\C=C/C([O-])=O HDRTWMBOUSPQON-ODZAUARKSA-L 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000001782 cephems Chemical group 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
229940097572 chloromycetin Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
239000006787 czapek-dox agar Substances 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000635 electron micrograph Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000012374 esterification agent Substances 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229940113083 morpholine Drugs 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
239000006877 oatmeal agar Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940051027 pasteurella multocida Drugs 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
239000003208 petroleum 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
229960005141 piperazine Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 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
229940048914 protamine Drugs 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
235000015113 tomato pastes and purées Nutrition 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
241001446247 uncultured actinomycete Species 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/08—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin disubstituted in the 7 position

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Health & Medical Sciences (AREA)
General Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

NO932/71A 1970-03-13 1971-03-12 NO134219C (nl)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO214572A NO134952C (nl)	1970-03-13	1972-06-16

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US1949670A	1970-03-13	1970-03-13
US5131970A	1970-06-30	1970-06-30
US9659470A	1970-12-09	1970-12-09
US05/115,779 US4302578A (en)	1970-12-09	1971-02-16	Cephalosporin antibiotics

Publications (2)

Publication Number	Publication Date
NO134219B true NO134219B (nl)	1976-05-24
NO134219C NO134219C (nl)	1976-09-01

Family

ID=27486855

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO932/71A NO134219C (nl)	1970-03-13	1971-03-12

Country Status (19)

Country	Link
JP (1)	JPS581919B1 (nl)
AR (3)	AR200370A1 (nl)
BE (1)	BE764160A (nl)
CA (1)	CA960169A (nl)
CH (5)	CH587856A5 (nl)
DD (3)	DD99166A5 (nl)
DE (3)	DE2109854C3 (nl)
DK (1)	DK131639C (nl)
FI (1)	FI51484C (nl)
FR (1)	FR2085702B1 (nl)
GB (1)	GB1321412A (nl)
IE (1)	IE35110B1 (nl)
IL (1)	IL36281A (nl)
IT (1)	IT1045524B (nl)
NL (1)	NL171285C (nl)
NO (1)	NO134219C (nl)
PH (1)	PH12292A (nl)
SE (1)	SE385713B (nl)
YU (1)	YU35164B (nl)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1040620A (en) *	1972-11-14	1978-10-17	Frank J. Urban	6-alkoxy-6-acylamidopenicillins 7-alkoxy-7-acylamido acetoxycephalosporins and process
US4065356A (en)	1976-02-12	1977-12-27	Merck & Co., Inc.	Production of antibiotic FR-02A (efrotomycin) by streptomyces lactamdurans
US4327093A (en)	1978-10-24	1982-04-27	Fujisawa Pharmaceutical Co., Ltd.	3,7-Disubstituted-2 or 3-cephem-4-carboxylic acid compounds
JPS5931517B2 (ja) *	1978-12-12	1984-08-02	山之内製薬株式会社	新規７↓−メトキシセファロスポリン誘導体
US4379920A (en) *	1979-10-31	1983-04-12	Glaxo Group Limited	Cephalosporins
EP0137365A3 (en) *	1983-09-06	1986-01-15	Takeda Chemical Industries, Ltd.	Cephalosporins and their production
EP0160745A3 (en) *	1984-05-07	1986-11-05	Takeda Chemical Industries, Ltd.	Cephem compounds and their production
ES2400562T3 (es)	2003-05-28	2013-04-10	Dsm Sinochem Pharmaceuticals Netherlands B.V.	Compuesto de cefem

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4945594A (nl) *	1972-09-08	1974-05-01

1971
- 1971-02-24 IL IL36281A patent/IL36281A/en unknown
- 1971-03-02 DE DE2109854A patent/DE2109854C3/de not_active Expired
- 1971-03-02 DE DE19712166462 patent/DE2166462B2/de active Granted
- 1971-03-02 DE DE19712166463 patent/DE2166463A1/de active Pending
- 1971-03-08 AR AR234333A patent/AR200370A1/es active
- 1971-03-08 CH CH1294175A patent/CH587856A5/de not_active IP Right Cessation
- 1971-03-08 CH CH1273075A patent/CH587911A5/xx not_active IP Right Cessation
- 1971-03-08 PH PH12269A patent/PH12292A/en unknown
- 1971-03-08 CH CH1273175A patent/CH586226A5/xx not_active IP Right Cessation
- 1971-03-08 CH CH333371A patent/CH579576A5/xx not_active IP Right Cessation
- 1971-03-08 CH CH1294275A patent/CH589655A5/xx not_active IP Right Cessation
- 1971-03-10 IE IE303/71A patent/IE35110B1/xx unknown
- 1971-03-11 SE SE7103119A patent/SE385713B/xx unknown
- 1971-03-11 FI FI710711A patent/FI51484C/fi active
- 1971-03-12 DD DD164639A patent/DD99166A5/xx unknown
- 1971-03-12 DD DD164638A patent/DD100002A5/xx unknown
- 1971-03-12 FR FR7108668A patent/FR2085702B1/fr not_active Expired
- 1971-03-12 NO NO932/71A patent/NO134219C/no unknown
- 1971-03-12 BE BE764160A patent/BE764160A/xx not_active IP Right Cessation
- 1971-03-12 NL NLAANVRAGE7103360,A patent/NL171285C/nl not_active IP Right Cessation
- 1971-03-12 DK DK118171A patent/DK131639C/da not_active IP Right Cessation
- 1971-03-12 DD DD153734A patent/DD96254A5/xx unknown
- 1971-03-12 CA CA107,642A patent/CA960169A/en not_active Expired
- 1971-03-12 IT IT49017/71A patent/IT1045524B/it active
- 1971-03-12 YU YU626/71A patent/YU35164B/xx unknown
- 1971-03-13 JP JP46013630A patent/JPS581919B1/ja active Pending
- 1971-04-19 GB GB2340771*A patent/GB1321412A/en not_active Expired
1972
- 1972-05-31 AR AR242279A patent/AR212149A1/es active
1974
- 1974-04-29 AR AR253505A patent/AR201142A1/es active

Also Published As

Publication number	Publication date
DE2166462B2 (de)	1977-01-20
FR2085702A1 (nl)	1971-12-31
SE385713B (sv)	1976-07-19
AR212149A1 (es)	1978-05-31
CH589655A5 (nl)	1977-07-15
CA960169A (en)	1974-12-31
IL36281A0 (en)	1971-04-28
DE2166462A1 (de)	1974-05-09
AR201142A1 (es)	1975-02-14
DE2109854B2 (de)	1974-09-26
DE2109854A1 (de)	1971-09-23
NL7103360A (nl)	1971-09-15
YU35164B (en)	1980-09-25
GB1321412A (en)	1973-06-27
CH587856A5 (nl)	1977-05-13
DD99166A5 (nl)	1973-07-20
NL171285B (nl)	1982-10-01
NL171285C (nl)	1983-03-01
CH587911A5 (nl)	1977-05-13
DK131639C (da)	1976-01-12
DK131639B (da)	1975-08-11
FR2085702B1 (nl)	1974-08-23
FI51484B (nl)	1976-09-30
YU62671A (en)	1979-12-31
BE764160A (fr)	1971-09-13
IE35110B1 (en)	1975-11-12
NO134219C (nl)	1976-09-01
CH586226A5 (nl)	1977-03-31
DD100002A5 (nl)	1973-09-05
CH579576A5 (nl)	1976-09-15
IL36281A (en)	1977-04-29
IE35110L (en)	1971-09-13
PH12292A (en)	1978-12-29
IT1045524B (it)	1980-05-10
FI51484C (fi)	1977-01-10
DE2166463A1 (de)	1974-05-02
JPS581919B1 (nl)	1983-01-13
DE2109854C3 (de)	1975-06-05
AR200370A1 (es)	1974-11-08
DD96254A5 (nl)	1973-03-12

Publication	Publication Date	Title
Su	1948	Micrococcin. An antibacterial substance formed by a strain of micrococcus
US4933180A (en)	1990-06-12	Novel antibiotic vermisporin, process for the production thereof and pharmaceutical composition comprising it as an active antibacterial agent
US4162323A (en)	1979-07-24	Antibiotic N-acetyl-dehydro-thienamycin
Burkholder et al.	1945	Further studies on the antibiotic activity of lichens
US4141986A (en)	1979-02-27	Antibiotics 890A2 and 890A5
NO134219B (nl)	1976-05-24
US4162324A (en)	1979-07-24	Antibiotics 890A1 and 890A3
US3914157A (en)	1975-10-21	Preparation of antibiotics by fermentation
US3985742A (en)	1976-10-12	Process for preparing 3-hydroxymethyl cephalosporins
US3049534A (en)	1962-08-14	Antibiotic and process of producing the same
Kim et al.	1974	STUDIES ON MIKAMYCIN B LACTONASE I. DEGRADATION OF MIKAMYCIN B BY STREPTOMYCES MITAKAENSIS
RU2077534C1 (ru)	1997-04-20	Тиомаринол, обладающий антибактериальными свойствами, штамм микроорганизма alteromonas rava sank-73390 - продуцент тиомаринола и способ получения антибиотика тиомаринола
US3832287A (en)	1974-08-27	Dipeptide antibiotic and method for the production thereof
SE412588B (sv)	1980-03-10	Forfarande for framstellning av acylderivat av antibiotikumet ws-4545
US4036696A (en)	1977-07-19	Preparation of antibiotics by fermentation
NO132242B (nl)	1975-06-30
US4302578A (en)	1981-11-24	Cephalosporin antibiotics
NO152451B (no)	1985-06-24	Fremgangsmaate for fremstilling av fosfonsyrederivater
NO127758B (nl)	1973-08-13
US4235967A (en)	1980-11-25	Process for producing antibiotics by cultivation of Streptomyces flavogriseus
CA1046965A (en)	1979-01-23	Naphthyridinomycin antibiotics from streptomyces
EP0001287B1 (en)	1982-03-17	Antibiotic no. 2-200, process for its production and pharmaceutical compositions containing antibiotic no. 2-200
US5192742A (en)	1993-03-09	Compounds and compositions for the treatment of bacterial infections in animals
US3598819A (en)	1971-08-10	Quinoxaline derivatives and process for producing the same
US3901880A (en)	1975-08-26	(s)-alanyl-3-(+60 -(s)-chloro-3-(s)-hydroxy-2-oxo-azetidinylmethyl)-(s)-alanine