NO116085B - - Google Patents
Info
- Publication number
- NO116085B NO116085B NO15373664A NO15373664A NO116085B NO 116085 B NO116085 B NO 116085B NO 15373664 A NO15373664 A NO 15373664A NO 15373664 A NO15373664 A NO 15373664A NO 116085 B NO116085 B NO 116085B
- Authority
- NO
- Norway
- Prior art keywords
- penicillin
- infrared spectrum
- aminobenzylpenicillin
- hydrated
- temperature
- Prior art date
Links
- AVKUERGKIZMTKX-YXLKDIQASA-N (2s,5r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)NC(=O)C(N)C1=CC=CC=C1 AVKUERGKIZMTKX-YXLKDIQASA-N 0.000 claims description 25
- 238000010438 heat treatment Methods 0.000 claims description 13
- 230000018044 dehydration Effects 0.000 claims description 10
- 238000006297 dehydration reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 description 28
- 229930182555 Penicillin Natural products 0.000 description 24
- 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 23
- 229940049954 penicillin Drugs 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- 238000001228 spectrum Methods 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic nitro compound Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000001914 filtration Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2491963A GB1016875A (en) | 1963-06-22 | 1963-06-22 | ª‡-aminobenzyl penicillin |
| GB3505463 | 1963-09-05 | ||
| GB3562663 | 1963-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116085B true NO116085B (da) | 1969-01-27 |
Family
ID=27258379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15373664A NO116085B (da) | 1963-06-22 | 1964-06-19 |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT249867B (da) |
| BE (1) | BE649197A (da) |
| BR (1) | BR6459876D0 (da) |
| CH (1) | CH450430A (da) |
| DE (1) | DE1279021B (da) |
| DK (1) | DK106973C (da) |
| ES (1) | ES301096A1 (da) |
| FI (1) | FI44613C (da) |
| FR (1) | FR1406104A (da) |
| GB (1) | GB1016875A (da) |
| NL (2) | NL6406859A (da) |
| NO (1) | NO116085B (da) |
| SE (1) | SE313814B (da) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1207933B (de) * | 1962-12-26 | 1965-12-30 | American Home Prod | Verfahren zur Herstellung von kristallwasser-freiem D-alpha-Aminobenzylpenicillin |
-
0
- NL NL123293D patent/NL123293C/xx active
-
1963
- 1963-06-22 GB GB2491963A patent/GB1016875A/en not_active Expired
-
1964
- 1964-06-10 BR BR15987664A patent/BR6459876D0/pt unknown
- 1964-06-12 BE BE649197D patent/BE649197A/xx unknown
- 1964-06-13 FI FI129164A patent/FI44613C/fi active
- 1964-06-15 DE DEB77261A patent/DE1279021B/de active Pending
- 1964-06-15 CH CH776964A patent/CH450430A/de unknown
- 1964-06-16 SE SE733764A patent/SE313814B/xx unknown
- 1964-06-16 ES ES301096A patent/ES301096A1/es not_active Expired
- 1964-06-17 FR FR978598A patent/FR1406104A/fr not_active Expired
- 1964-06-17 NL NL6406859A patent/NL6406859A/xx unknown
- 1964-06-18 DK DK306664A patent/DK106973C/da active
- 1964-06-19 NO NO15373664A patent/NO116085B/no unknown
- 1964-06-19 AT AT526364A patent/AT249867B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1016875A (en) | 1966-01-12 |
| ES301096A1 (es) | 1964-12-01 |
| FI44613B (da) | 1971-08-31 |
| BR6459876D0 (pt) | 1973-08-14 |
| CH450430A (de) | 1968-01-31 |
| NL123293C (da) | |
| FR1406104A (fr) | 1965-07-16 |
| SE313814B (da) | 1969-08-25 |
| BE649197A (da) | 1964-10-01 |
| DE1279021B (de) | 1968-10-03 |
| FI44613C (fi) | 1974-05-13 |
| DK106973C (da) | 1967-04-10 |
| AT249867B (de) | 1966-10-10 |
| NL6406859A (da) | 1964-12-23 |
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