CH625803A5 - Process for the preparation of thienamycin and its isomers deacetyl-890 A1 and 890 A3 - Google Patents
Process for the preparation of thienamycin and its isomers deacetyl-890 A1 and 890 A3 Download PDFInfo
- Publication number
- CH625803A5 CH625803A5 CH1459976A CH1459976A CH625803A5 CH 625803 A5 CH625803 A5 CH 625803A5 CH 1459976 A CH1459976 A CH 1459976A CH 1459976 A CH1459976 A CH 1459976A CH 625803 A5 CH625803 A5 CH 625803A5
- Authority
- CH
- Switzerland
- Prior art keywords
- amidohydrolase
- acetylthienamycin
- solution
- antibiotics
- antibiotic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 title claims description 13
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 12
- VUDXUIMGYZQRKK-GTNGPMTGSA-N N-Acetylthienamycin Chemical compound C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 VUDXUIMGYZQRKK-GTNGPMTGSA-N 0.000 claims description 33
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- 230000005540 biological transmission Effects 0.000 description 1
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- 239000001506 calcium phosphate Substances 0.000 description 1
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- 235000021240 caseins Nutrition 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 230000000850 deacetylating effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- HYPPXZBJBPSRLK-UHFFFAOYSA-N diphenoxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 HYPPXZBJBPSRLK-UHFFFAOYSA-N 0.000 description 1
- 229960004192 diphenoxylate Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
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- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
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- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
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- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- 235000010603 pastilles Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
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- 229940035049 sorbitan monooleate Drugs 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
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- 239000002511 suppository base Substances 0.000 description 1
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- 238000002834 transmittance Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63456075A | 1975-11-24 | 1975-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625803A5 true CH625803A5 (en) | 1981-10-15 |
Family
ID=24544292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1459976A CH625803A5 (en) | 1975-11-24 | 1976-11-19 | Process for the preparation of thienamycin and its isomers deacetyl-890 A1 and 890 A3 |
Country Status (16)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7800979L (sv) * | 1977-02-11 | 1978-08-12 | Merck & Co Inc | Antibiotikum |
| SE7800978L (sv) * | 1977-02-11 | 1978-08-12 | Merck & Co Inc | Antibiotikum |
| US4162193A (en) * | 1977-08-19 | 1979-07-24 | Merck & Co., Inc. | Enzymatic cleavage of N-acyl-thienamycins |
| NZ190994A (en) | 1978-07-24 | 1981-10-19 | Merck & Co Inc | Z-2-acylamino-3-monosubstituted propenoates |
| EP0024447B1 (en) * | 1979-08-28 | 1983-07-20 | Merck & Co. Inc. | Process for purifying thienamycin |
| DE3146190A1 (de) * | 1981-11-21 | 1983-06-16 | Hoechst Ag, 6230 Frankfurt | Isolierung von chemisch instabilen antibiotika aus fermentationsloesungen |
| US10695322B2 (en) | 2016-01-29 | 2020-06-30 | The Johns Hopkins University | Inhibitors of bacterial growth |
-
1976
- 1976-11-03 DK DK497476A patent/DK497476A/da not_active Application Discontinuation
- 1976-11-04 SE SE7612295A patent/SE7612295L/xx not_active Application Discontinuation
- 1976-11-15 AU AU19645/76A patent/AU510252B2/en not_active Expired
- 1976-11-16 BE BE172363A patent/BE848349A/xx not_active IP Right Cessation
- 1976-11-16 AR AR265526A patent/AR224224A1/es active
- 1976-11-16 PT PT65845A patent/PT65845B/pt unknown
- 1976-11-18 HU HUME002031 patent/HU175266B/hu unknown
- 1976-11-19 DE DE19762652678 patent/DE2652678A1/de not_active Withdrawn
- 1976-11-19 NL NL7612932A patent/NL7612932A/xx not_active Application Discontinuation
- 1976-11-19 FR FR7634889A patent/FR2351979A1/fr active Granted
- 1976-11-19 GB GB48233/76A patent/GB1561108A/en not_active Expired
- 1976-11-19 CH CH1459976A patent/CH625803A5/de not_active IP Right Cessation
- 1976-11-19 ES ES453508A patent/ES453508A1/es not_active Expired
- 1976-11-20 GR GR52224A patent/GR61407B/el unknown
- 1976-11-22 JP JP51139656A patent/JPS5265295A/ja active Pending
- 1976-11-23 ZA ZA00766986A patent/ZA766986B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE848349A (fr) | 1977-05-16 |
| PT65845B (en) | 1978-10-10 |
| GR61407B (en) | 1978-11-11 |
| FR2351979A1 (fr) | 1977-12-16 |
| ZA766986B (en) | 1978-06-28 |
| FR2351979B1 (enrdf_load_stackoverflow) | 1982-08-13 |
| NL7612932A (nl) | 1977-05-26 |
| DK497476A (da) | 1977-05-25 |
| HU175266B (hu) | 1980-06-28 |
| AU1964576A (en) | 1978-05-25 |
| PT65845A (en) | 1976-12-01 |
| SE7612295L (sv) | 1977-05-25 |
| GB1561108A (en) | 1980-02-13 |
| ES453508A1 (es) | 1978-03-01 |
| AU510252B2 (en) | 1980-06-19 |
| JPS5265295A (en) | 1977-05-30 |
| AR224224A1 (es) | 1981-11-13 |
| DE2652678A1 (de) | 1977-06-02 |
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