CH626628A5 - Process for the preparation of an antibiotic - Google Patents
Process for the preparation of an antibiotic Download PDFInfo
- Publication number
- CH626628A5 CH626628A5 CH400175A CH400175A CH626628A5 CH 626628 A5 CH626628 A5 CH 626628A5 CH 400175 A CH400175 A CH 400175A CH 400175 A CH400175 A CH 400175A CH 626628 A5 CH626628 A5 CH 626628A5
- Authority
- CH
- Switzerland
- Prior art keywords
- salt
- salts
- complex
- water
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 44
- 238000002360 preparation method Methods 0.000 title claims description 23
- 230000003115 biocidal effect Effects 0.000 title claims description 15
- 230000008569 process Effects 0.000 title claims description 14
- 239000003242 anti bacterial agent Substances 0.000 title claims description 8
- FQQFFZPBGYGDSX-NJFHWYBASA-N epithienamycin E Chemical compound C1C(S\C=C\NC(C)=O)=C(C(O)=O)N2C(=O)[C@@H]([C@@H](OS(O)(=O)=O)C)[C@H]21 FQQFFZPBGYGDSX-NJFHWYBASA-N 0.000 claims description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 54
- 241000218589 Streptomyces olivaceus Species 0.000 claims description 47
- 239000000243 solution Substances 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 241000588724 Escherichia coli Species 0.000 claims description 19
- 102000006635 beta-lactamase Human genes 0.000 claims description 19
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 18
- 230000000844 anti-bacterial effect Effects 0.000 claims description 18
- 235000010980 cellulose Nutrition 0.000 claims description 18
- 229920002678 cellulose Polymers 0.000 claims description 18
- 241000894007 species Species 0.000 claims description 18
- 239000001913 cellulose Substances 0.000 claims description 17
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 17
- 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 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 108090000204 Dipeptidase 1 Proteins 0.000 claims description 15
- 238000000855 fermentation Methods 0.000 claims description 15
- 230000004151 fermentation Effects 0.000 claims description 15
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 14
- 229960000723 ampicillin Drugs 0.000 claims description 14
- 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 claims description 14
- 241000187747 Streptomyces Species 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 241000588770 Proteus mirabilis Species 0.000 claims description 10
- 241000191967 Staphylococcus aureus Species 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 10
- -1 ammonium ions Chemical class 0.000 claims description 9
- 239000003086 colorant Substances 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 7
- 229940056360 penicillin g Drugs 0.000 claims description 7
- 239000008363 phosphate buffer Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 238000004809 thin layer chromatography Methods 0.000 claims description 7
- 244000063299 Bacillus subtilis Species 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000002195 synergetic effect Effects 0.000 claims description 6
- 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 claims description 5
- 229920005654 Sephadex Polymers 0.000 claims description 5
- 239000012507 Sephadex™ Substances 0.000 claims description 5
- 239000003781 beta lactamase inhibitor Substances 0.000 claims description 5
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 5
- 108020004256 Beta-lactamase Proteins 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 229930182555 Penicillin Natural products 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000005342 ion exchange Methods 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 4
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 4
- 241000588772 Morganella morganii Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229960003022 amoxicillin Drugs 0.000 claims description 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 3
- 229920001429 chelating resin Polymers 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000019371 penicillin G benzathine Nutrition 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000011343 solid material Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 2
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 238000002523 gelfiltration Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 4
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims 4
- 239000012876 carrier material Substances 0.000 claims 4
- 239000002132 β-lactam antibiotic Substances 0.000 claims 4
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 4
- 229930186147 Cephalosporin Natural products 0.000 claims 2
- 229920002307 Dextran Polymers 0.000 claims 2
- 241001522878 Escherichia coli B Species 0.000 claims 2
- 238000000862 absorption spectrum Methods 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 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 claims 2
- 229960003866 cefaloridine Drugs 0.000 claims 2
- 229940124587 cephalosporin Drugs 0.000 claims 2
- 150000001780 cephalosporins Chemical class 0.000 claims 2
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002960 penicillins Chemical class 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical class C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 claims 1
- 238000007445 Chromatographic isolation Methods 0.000 claims 1
- 206010018612 Gonorrhoea Diseases 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 206010033078 Otitis media Diseases 0.000 claims 1
- 229930195708 Penicillin V Natural products 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims 1
- 229960003669 carbenicillin Drugs 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 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 claims 1
- 229950004030 cefaloglycin Drugs 0.000 claims 1
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- 229960002682 cefoxitin Drugs 0.000 claims 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 claims 1
- 229940106164 cephalexin Drugs 0.000 claims 1
- 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 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
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- 208000001786 gonorrhea Diseases 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
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- 230000007935 neutral effect Effects 0.000 claims 1
- 229940056367 penicillin v Drugs 0.000 claims 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims 1
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- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical compound CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims 1
- HOCWPKXKMNXINF-XQERAMJGSA-N propicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(CC)OC1=CC=CC=C1 HOCWPKXKMNXINF-XQERAMJGSA-N 0.000 claims 1
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- 229940124597 therapeutic agent Drugs 0.000 claims 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
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- 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
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G11/00—Antibiotics
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
- C12P17/184—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system containing a beta-lactam ring, e.g. thienamycin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB13856/74A GB1489235A (en) | 1974-03-28 | 1974-03-28 | Antibiotics |
AU45499/79A AU530414B2 (en) | 1974-03-28 | 1979-03-29 | Antibiotic mm13902 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH626628A5 true CH626628A5 (en) | 1981-11-30 |
Family
ID=25627229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH400175A CH626628A5 (en) | 1974-03-28 | 1975-03-27 | Process for the preparation of an antibiotic |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS582675B2 (ja) |
AT (1) | AT345454B (ja) |
AU (2) | AU499459B2 (ja) |
BE (1) | BE827332A (ja) |
CA (1) | CA1050460A (ja) |
CH (1) | CH626628A5 (ja) |
DE (1) | DE2513854C2 (ja) |
FR (1) | FR2265399B1 (ja) |
GB (1) | GB1489235A (ja) |
LU (1) | LU72155A1 (ja) |
NL (1) | NL7503672A (ja) |
OA (1) | OA05204A (ja) |
SE (1) | SE7503536L (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK145504C (da) * | 1976-04-28 | 1983-04-25 | Merck & Co Inc | Fremgangsmaade til fremstilling af det antibiotiske stof 890a2og/eller det antibiotiske stof 890a5 og farmaceutisk acceptable salte deraf |
NL7712091A (nl) * | 1976-11-17 | 1978-05-19 | Merck & Co Inc | Werkwijze ter bereiding van een nieuw antibiotisch middel. |
US4446146A (en) * | 1978-07-26 | 1984-05-01 | Beecham Group Limited | β-Lactam containing compounds, their preparation and use |
EP0008885B1 (en) * | 1978-09-09 | 1983-11-30 | Beecham Group Plc | Beta-lactam compounds, their preparation and use |
US4530791A (en) * | 1979-04-16 | 1985-07-23 | Kowa Co., Ltd. | β-Lactam antibiotics |
JPS6029668A (ja) * | 1983-07-28 | 1985-02-15 | Hino Motors Ltd | 経済運転ガイド装置 |
CN1976747A (zh) * | 2004-06-30 | 2007-06-06 | 帝斯曼知识产权资产管理有限公司 | 包含beta-内酰胺抗生素的产品 |
-
1974
- 1974-03-28 GB GB13856/74A patent/GB1489235A/en not_active Expired
-
1975
- 1975-03-25 AT AT228475A patent/AT345454B/de not_active IP Right Cessation
- 1975-03-26 SE SE7503536*1A patent/SE7503536L/xx unknown
- 1975-03-27 NL NL7503672A patent/NL7503672A/xx not_active Application Discontinuation
- 1975-03-27 LU LU72155A patent/LU72155A1/xx unknown
- 1975-03-27 CH CH400175A patent/CH626628A5/de not_active IP Right Cessation
- 1975-03-27 AU AU79599/75A patent/AU499459B2/en not_active Ceased
- 1975-03-27 FR FR7509611A patent/FR2265399B1/fr not_active Expired
- 1975-03-27 DE DE2513854A patent/DE2513854C2/de not_active Expired
- 1975-03-27 CA CA223,313A patent/CA1050460A/en not_active Expired
- 1975-03-28 BE BE154898A patent/BE827332A/xx not_active IP Right Cessation
- 1975-03-28 JP JP50038464A patent/JPS582675B2/ja not_active Expired
- 1975-04-29 OA OA55487A patent/OA05204A/xx unknown
-
1979
- 1979-03-29 AU AU45499/79A patent/AU530414B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
DE2513854C2 (de) | 1984-04-19 |
LU72155A1 (ja) | 1975-08-20 |
AT345454B (de) | 1978-09-25 |
AU7959975A (en) | 1976-09-30 |
JPS582675B2 (ja) | 1983-01-18 |
BE827332A (fr) | 1975-09-29 |
FR2265399B1 (ja) | 1978-08-04 |
DE2513854A1 (de) | 1975-10-02 |
AU530414B2 (en) | 1983-07-14 |
FR2265399A1 (ja) | 1975-10-24 |
GB1489235A (en) | 1977-10-19 |
CA1050460A (en) | 1979-03-13 |
ATA228475A (de) | 1978-01-15 |
NL7503672A (nl) | 1975-09-30 |
OA05204A (fr) | 1981-02-28 |
SE7503536L (sv) | 1975-09-29 |
AU499459B2 (en) | 1979-04-26 |
AU4549979A (en) | 1981-05-14 |
JPS50140692A (ja) | 1975-11-11 |
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Legal Events
Date | Code | Title | Description |
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PL | Patent ceased |