CA1044627A - Antibiotique du type de la cephalosporine produit par des micro-organismes - Google Patents

Antibiotique du type de la cephalosporine produit par des micro-organismes

Info

Publication number: CA1044627A
Authority: CA; Canada
Prior art keywords: alpha; amino; cephem; triazol; process according
Prior art date: 1974-12-04
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

CA220,354A

Other languages

English (en)

Other versions

CA220354S (en

Inventor

Leonard B. Crast (Jr.)

David Willner

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.)

1974-12-04

Filing date

1975-02-18

Publication date

1978-12-19

1974-12-04 Priority claimed from US05/529,508 external-priority patent/US4009361A/en

1975-02-18 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1978-12-19 Application granted granted Critical

1978-12-19 Publication of CA1044627A publication Critical patent/CA1044627A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
229930186147 Cephalosporin Natural products 0.000 title description 9
229940124587 cephalosporin Drugs 0.000 title description 9
150000001780 cephalosporins Chemical class 0.000 title description 9
230000000813 microbial effect Effects 0.000 title description 8
230000003115 biocidal effect Effects 0.000 title 1
108090000790 Enzymes Proteins 0.000 claims abstract description 24
102000004190 Enzymes Human genes 0.000 claims abstract description 24
244000005700 microbiome Species 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
MLOZJRLUNNFSGD-IOJJLOCKSA-N (6r)-7-amino-8-oxo-3-(2h-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC=1C=NNN=1 MLOZJRLUNNFSGD-IOJJLOCKSA-N 0.000 claims abstract description 4
239000007864 aqueous solution Substances 0.000 claims abstract description 4
241000589212 Acetobacter pasteurianus Species 0.000 claims abstract description 3
241000589516 Pseudomonas Species 0.000 claims abstract description 3
241000589655 Xanthomonas citri Species 0.000 claims abstract description 3
241000965481 Darksidea alpha Species 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 24
239000003242 anti bacterial agent Substances 0.000 abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract description 2
241000894006 Bacteria Species 0.000 abstract 1
208000035473 Communicable disease Diseases 0.000 abstract 1
241001465754 Metazoa Species 0.000 abstract 1
230000036765 blood level Effects 0.000 abstract 1
231100000252 nontoxic Toxicity 0.000 abstract 1
230000003000 nontoxic effect Effects 0.000 abstract 1
230000003389 potentiating effect Effects 0.000 abstract 1
230000002035 prolonged effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
229940088598 enzyme Drugs 0.000 description 22
239000000047 product Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000001914 filtration Methods 0.000 description 9
230000010933 acylation Effects 0.000 description 7
238000005917 acylation reaction Methods 0.000 description 7
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
230000002255 enzymatic effect Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000008363 phosphate buffer Substances 0.000 description 4
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
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 3
239000003610 charcoal Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical compound SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000589634 Xanthomonas Species 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000008272 agar Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000013592 cell lysate Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000012552 review Methods 0.000 description 2
239000007790 solid phase Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
YWAVLHZJMWEYTA-YDALLXLXSA-N ATEE Chemical compound O.CCOC(=O)[C@@H](NC(C)=O)CC1=CC=C(O)C=C1 YWAVLHZJMWEYTA-YDALLXLXSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
108010023063 Bacto-peptone Proteins 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
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 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
229930006000 Sucrose Natural products 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
238000010521 absorption reaction Methods 0.000 description 1
VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 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
238000004458 analytical method Methods 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
238000012474 bioautography Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
229940041514 candida albicans extract Drugs 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
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound 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 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
229940106164 cephalexin Drugs 0.000 description 1
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
229960001927 cetylpyridinium chloride Drugs 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
229940079919 digestives enzyme preparation Drugs 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052588 hydroxylapatite Inorganic materials 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
235000013923 monosodium glutamate Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
-1 p-hydroxycephalexin Chemical compound 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229940073490 sodium glutamate Drugs 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA220,354A 1974-12-04 1975-02-18 Antibiotique du type de la cephalosporine produit par des micro-organismes Expired CA1044627A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/529,508 US4009361A (en)	1973-12-04	1974-12-04	Electrical discharge machining apparatus with monitoring circuit and means to check the operability of the monitoring circuit

Publications (1)

Publication Number	Publication Date
CA1044627A true CA1044627A (fr)	1978-12-19

Family

ID=24110198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA220,354A Expired CA1044627A (fr)	1974-12-04	1975-02-18	Antibiotique du type de la cephalosporine produit par des micro-organismes

Country Status (1)

Country	Link
CA (1)	CA1044627A (fr)

1975
- 1975-02-18 CA CA220,354A patent/CA1044627A/fr not_active Expired

Publication	Publication Date	Title
US4525352A (en)	1985-06-25	Antibiotics
US4110165A (en)	1978-08-29	Process for the production of clavulanic acid
MATSUKUMA et al.	1989	Synthesis and biological evaluation of 3-chloro-1-carbacephem compounds
US4529720A (en)	1985-07-16	Antibiotic from Streptomyces clavulicerus
US6048977A (en)	2000-04-11	Clavulanic acid and salts thereof
EP0014476B1 (fr)	1983-08-10	Analogues acylés optiquement actifs de céphalosporines, procédés pour leur préparation et compositions pharmaceutiques les contenant
US4335211A (en)	1982-06-15	Process for producing optically active cephalosporin analogs
US3899394A (en)	1975-08-12	Production of antibacterial agents
JPS589680B2 (ja)	1983-02-22	アミノカゴウブツノセイホウ
CA1044627A (fr)	1978-12-19	Antibiotique du type de la cephalosporine produit par des micro-organismes
US4525353A (en)	1985-06-25	Antibiotics
US4656288A (en)	1987-04-07	Antibiotics, their production and use
EP0025602B1 (fr)	1984-12-19	Analogues acylés de céphalosporine, procédé pour leur préparation et compositions pharmaceutiques les contenant
GORDON et al.	1982	Cephamycin antibiotics
GB2042532A (en)	1980-09-24	Antibiotics c-19393 s2 and 'i
EP0014475B1 (fr)	1984-02-15	Analogues de céphalosporine optiquement actifs, procédé pour leur préparation et leur utilisation dans la preparation des compositions pharmaceutiques
CA1109860A (fr)	1981-09-29	Procede de production de cephalosporines du type lactol
CA1238594A (fr)	1988-06-28	Antibiotiques tan-558, production et application
US4061649A (en)	1977-12-06	Clavulanic acid sulphates
US3522250A (en)	1970-07-28	Derivatives of 7-aminocephalosporanic acid
US4302540A (en)	1981-11-24	Process of producing optically active cephalosporin analogs by enzyme selective deacylation
US4755596A (en)	1988-07-05	Optically active carbacephems
US4316958A (en)	1982-02-23	Process for producing optically active cephalosporin analogs
US4008227A (en)	1977-02-15	Cephalosporins
US4242449A (en)	1980-12-30	7-Methoxy cephalosporins and process of producing them