DE2623835C2 - Verfahren zur Herstellung von Natriumampicillin - Google Patents
Verfahren zur Herstellung von NatriumampicillinInfo
- Publication number
- DE2623835C2 DE2623835C2 DE2623835A DE2623835A DE2623835C2 DE 2623835 C2 DE2623835 C2 DE 2623835C2 DE 2623835 A DE2623835 A DE 2623835A DE 2623835 A DE2623835 A DE 2623835A DE 2623835 C2 DE2623835 C2 DE 2623835C2
- Authority
- DE
- Germany
- Prior art keywords
- ampicillin
- sodium
- amphicillin
- solution
- manufacture
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims description 12
- 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 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000011734 sodium Substances 0.000 title claims description 5
- 229910052708 sodium Inorganic materials 0.000 title claims description 5
- 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 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 229960000723 ampicillin Drugs 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 15
- 238000004108 freeze drying Methods 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 230000007812 deficiency Effects 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].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 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 3
- 229960003311 ampicillin trihydrate Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012792 lyophilization process Methods 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 238000012009 microbiological test Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RZWWGOCLMSGROE-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl RZWWGOCLMSGROE-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and 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
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623835A DE2623835C2 (de) | 1976-05-28 | 1976-05-28 | Verfahren zur Herstellung von Natriumampicillin |
| US05/797,928 US4130558A (en) | 1976-05-28 | 1977-05-18 | Process for preparation of alkali metal salts of ampicillin |
| GB22550/77A GB1522470A (en) | 1976-05-28 | 1977-05-27 | Process for the preparation of alkali metal salts of ampicillin |
| FR7716406A FR2352819A1 (fr) | 1976-05-28 | 1977-05-27 | Procede de preparation de sels alcalins de l'ampicilline, notamment du sel de sodium |
| JP6126577A JPS52151714A (en) | 1976-05-28 | 1977-05-27 | Preparation of alkaline salt of ampicillin |
| ES459223A ES459223A1 (es) | 1976-05-28 | 1977-05-27 | Procedimiento para la preparacion de sales alcalinos de am- picilina, especialmente de ampicilina sodica. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623835A DE2623835C2 (de) | 1976-05-28 | 1976-05-28 | Verfahren zur Herstellung von Natriumampicillin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2623835B1 DE2623835B1 (de) | 1977-06-16 |
| DE2623835C2 true DE2623835C2 (de) | 1978-03-02 |
Family
ID=5979158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2623835A Expired DE2623835C2 (de) | 1976-05-28 | 1976-05-28 | Verfahren zur Herstellung von Natriumampicillin |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4130558A (enExample) |
| JP (1) | JPS52151714A (enExample) |
| DE (1) | DE2623835C2 (enExample) |
| ES (1) | ES459223A1 (enExample) |
| FR (1) | FR2352819A1 (enExample) |
| GB (1) | GB1522470A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1209477A (en) * | 1981-03-26 | 1986-08-12 | Bruce E. Haeger | Composition of matter comprising a lyophilized preparation of a penicillin derivative |
| AT380258B (de) * | 1982-08-06 | 1986-05-12 | Biochemie Gmbh | Verfahren zur herstellung von natrium-ampicillin |
| JPS63174927A (ja) * | 1987-01-14 | 1988-07-19 | Tanabe Seiyaku Co Ltd | 抗菌性凍結乾燥製剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5119016B2 (enExample) * | 1972-03-10 | 1976-06-14 | ||
| GB1463563A (en) * | 1974-10-10 | 1977-02-02 | Beecham Group Ltd | Pharmaceutical compositions |
-
1976
- 1976-05-28 DE DE2623835A patent/DE2623835C2/de not_active Expired
-
1977
- 1977-05-18 US US05/797,928 patent/US4130558A/en not_active Expired - Lifetime
- 1977-05-27 ES ES459223A patent/ES459223A1/es not_active Expired
- 1977-05-27 GB GB22550/77A patent/GB1522470A/en not_active Expired
- 1977-05-27 JP JP6126577A patent/JPS52151714A/ja active Pending
- 1977-05-27 FR FR7716406A patent/FR2352819A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2352819B1 (enExample) | 1980-02-08 |
| ES459223A1 (es) | 1978-03-01 |
| GB1522470A (en) | 1978-08-23 |
| US4130558A (en) | 1978-12-19 |
| FR2352819A1 (fr) | 1977-12-23 |
| JPS52151714A (en) | 1977-12-16 |
| DE2623835B1 (de) | 1977-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |