FR2120150A1 - Anhydrous ampicillin prepn - without isolation of hydrated ampicillin - Google Patents
Anhydrous ampicillin prepn - without isolation of hydrated ampicillinInfo
- Publication number
- FR2120150A1 FR2120150A1 FR7147568A FR7147568A FR2120150A1 FR 2120150 A1 FR2120150 A1 FR 2120150A1 FR 7147568 A FR7147568 A FR 7147568A FR 7147568 A FR7147568 A FR 7147568A FR 2120150 A1 FR2120150 A1 FR 2120150A1
- Authority
- FR
- France
- Prior art keywords
- ampicillin
- hydrated
- anhydrous
- isolation
- prepn
- 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.)
- Granted
Links
- 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 title abstract 5
- 229960000723 ampicillin Drugs 0.000 title abstract 3
- 238000002955 isolation Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000004983 alkyl aryl ketones Chemical class 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The anhydrous form of ampicillin is produced by condensing 6-APA with a cpd. C6H5-CH(NH-R)-COR1 (where R is H or a gp. -C(CH3)=CH-COCH3 or -C(CH3)=CH-COOC2H5 and R1 is Cl or -O-CO-R11 in which R11 contains 1-7 C atoms, or R and R1 together form a -CO-O-) in an aqs. soln. of a 3-10C aliphatic, alicyclic or alkyl aryl ketone or in a 1-3C chlorinated solvent and, after completion of the reaction, evaporating the solvent at 20-100 degrees C. The new procedure gives anhydrous ampicillin (which is more stable and gives higher blood antibiotic levels than the hydrated form) directly, and the yield is better than that of procedures involving the isolation and separate dehydration of hydrated ampicillin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3376070A IT1043957B (en) | 1970-12-31 | 1970-12-31 | PROCESS FOR THE PREPARATION OF THE ANHYDROUS FORM OF ACID 6, D, LESS ALPINE AMINOPHENYLACETAMIDE PENICILLANIC |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2120150A1 true FR2120150A1 (en) | 1972-08-11 |
| FR2120150B1 FR2120150B1 (en) | 1975-06-20 |
Family
ID=11238092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7147568A Granted FR2120150A1 (en) | 1970-12-31 | 1971-12-30 | Anhydrous ampicillin prepn - without isolation of hydrated ampicillin |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2165200A1 (en) |
| FR (1) | FR2120150A1 (en) |
| IT (1) | IT1043957B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0439096A3 (en) * | 1990-01-22 | 1992-06-10 | Biochemie Gesellschaft M.B.H. | Improvements in or relating to beta lactam production |
| ES2050621A1 (en) * | 1992-11-06 | 1994-05-16 | Antibioticos Sa | An improved procedure for the preparation of 6-[alpha]- aminopenicillins |
| NL1013402C2 (en) * | 1999-10-27 | 2001-05-01 | Dsm Nv | Method for the preparation of a beta-lactam antibiotic. |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1053313B (en) * | 1976-01-15 | 1981-08-31 | Ankerfarm Spa | PROCEDURE FOR PRODUCING SEMI-SYNTHETIC ANTIBIOTICS |
| DE102007042653A1 (en) | 2007-09-10 | 2009-03-12 | HOSCH-FöRDERTECHNIK RECKLINGHAUSEN GMBH | Apparatus for stripping impurities from a belt of conveyor belts |
-
1970
- 1970-12-31 IT IT3376070A patent/IT1043957B/en active
-
1971
- 1971-12-29 DE DE19712165200 patent/DE2165200A1/en active Pending
- 1971-12-30 FR FR7147568A patent/FR2120150A1/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0439096A3 (en) * | 1990-01-22 | 1992-06-10 | Biochemie Gesellschaft M.B.H. | Improvements in or relating to beta lactam production |
| US5840885A (en) * | 1990-01-22 | 1998-11-24 | Biochemie Gesellschaft M.B.H. | Processes for the production of 6-α-aminoacyl-penicillin and 7-.alpha. |
| EP0976755A1 (en) * | 1990-01-22 | 2000-02-02 | BIOCHEMIE Gesellschaft m.b.H. | Improvements in or relating to beta lactam production |
| ES2050621A1 (en) * | 1992-11-06 | 1994-05-16 | Antibioticos Sa | An improved procedure for the preparation of 6-[alpha]- aminopenicillins |
| NL1013402C2 (en) * | 1999-10-27 | 2001-05-01 | Dsm Nv | Method for the preparation of a beta-lactam antibiotic. |
| WO2001030783A1 (en) * | 1999-10-27 | 2001-05-03 | Dsm N.V. | PROCESS FOR THE PREPARATION OF A β-LACTAM ANTIBIOTIC |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1043957B (en) | 1980-02-29 |
| DE2165200A1 (en) | 1972-07-13 |
| FR2120150B1 (en) | 1975-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |