NO821174L - PROCEDURE FOR THE PREPARATION OF SODIUM AMOXILLIN - Google Patents
PROCEDURE FOR THE PREPARATION OF SODIUM AMOXILLINInfo
- Publication number
- NO821174L NO821174L NO821174A NO821174A NO821174L NO 821174 L NO821174 L NO 821174L NO 821174 A NO821174 A NO 821174A NO 821174 A NO821174 A NO 821174A NO 821174 L NO821174 L NO 821174L
- Authority
- NO
- Norway
- Prior art keywords
- sodium
- solution
- procedure
- preparation
- amoxillin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 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 description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 229910052708 sodium Inorganic materials 0.000 title description 2
- 239000011734 sodium Substances 0.000 title description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
- BYHDFCISJXIVBV-YWUHCJSESA-M amoxicillin 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=C(O)C=C1 BYHDFCISJXIVBV-YWUHCJSESA-M 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960003022 amoxicillin Drugs 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 239000000539 dimer Substances 0.000 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 description 3
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 2
- 238000012503 pharmacopoeial method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C07D499/04—Preparation
- C07D499/14—Preparation of salts
- C07D499/16—Preparation of salts of alkali or alkaline earth metals
-
- 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
Description
1 Foreliggende oppfinnelse vedrører fremstilling av fast natrium amoxicilian ved å sprøyte-tørke en løsning av natrium lam-' oxicillån i en blanding av vann og t-butanol. 1 The present invention relates to the production of solid sodium amoxicillin by spray-drying a solution of sodium lamoxicillan in a mixture of water and t-butanol.
Fast natrium amoxicillin har vært fremstilt ved utfellingSolid sodium amoxicillin has been prepared by precipitation
(som i UK 1,241.844 og UK 1. 286 .199) , men fra et kommersielt! . synspunkt er produktet funnet utilfredsstillende p.g.a. urenheter forårsaket av rester så som trietylamin eller natrium 2-etylhexanoat eller overskudd av løsningsmidler. (as in UK 1,241,844 and UK 1,286,199) , but from a commercial! . point of view, the product has been found unsatisfactory due to impurities caused by residues such as triethylamine or sodium 2-ethylhexanoate or excess solvents.
Fast natrium amoxicillin har også vært fremstilt ved fryse-tørking (UK 1.527,557.og UK 1.543.317), men dette forutsetter særdeles kostbart utstyr for å produsere tilstrekkelige mengder for salg; i tillegg kreves det meget lang produksjons-tid på grunn av de meget lave temperaturer som er nødvendige og som igjen reduserer produksjonsutstyrets effekt. Solid sodium amoxicillin has also been produced by freeze-drying (UK 1,527,557 and UK 1,543,317), but this requires extremely expensive equipment to produce sufficient quantities for sale; in addition, a very long production time is required due to the very low temperatures which are necessary and which in turn reduce the efficiency of the production equipment.
Ved fremgangsmåten ifølge foreliggende oppfinnelse benyttetIn the method according to the present invention used
man en sluttet syklussprøytetørker; hovedbestanddelere av dette apparat er tørkekammer, produkt-syklon, . avløpsvifte, kon-denser/renseanordning (støtplate, glykolavkjølt) nitrogenvifte, varmeveksler (Dowtherm) og matepumpe. Apparatet var konstruert for samvirkeoperasjon med syklonprodukt-avløpet. Enheten ble først spylet med nitrogen for å redusere oksygennivåst. til et sikkert nivå, slik at løsningsblandingen kunne føres til kon-denseren (dette muliggjør at konstante tørkebetingelser raskt oppnås.) Enheten fikk deretter den ønskede ^-innløpstemperatur, gasstrøm, kondensertemperatur etc. Matingen (natrium amoxicillin i vandig t-butanolløsning) ble pumpet gjennom en sprøyte-dyse på top-pen av tørkekammeret.. Tørketproduktet og gass ble ført gjennom bunnen for å bli separert i en syklon. one a closed cycle spray dryer; main components of this device are drying chamber, product cyclone, . drain fan, condenser/cleaning device (bumper plate, glycol-cooled) nitrogen fan, heat exchanger (Dowtherm) and feed pump. The device was designed for cooperative operation with the cyclone product drain. The unit was first flushed with nitrogen to reduce oxygen levels. to a safe level, so that the solution mixture could be fed to the condenser (this enables constant drying conditions to be quickly achieved.) The unit was then given the desired ^-inlet temperature, gas flow, condenser temperature, etc. The feed (sodium amoxicillin in aqueous t-butanol solution) was pumped through a spray nozzle on the top of the drying chamber. The dried product and gas were passed through the bottom to be separated in a cyclone.
Produkt data Product data
Bestemt på en vannfri løsningsfri basis ved anvendelse av British Pharmacopeia-fremgangsmåten for å måle forurensing av'penicillinsyre og dimere e.l. Determined on an anhydrous solution-free basis using the British Pharmacopeia method for measuring contamination by penicillinic acid and dimers, etc.
Renheten og de fysiske egenskapene til de fire produkteneThe purity and physical properties of the four products
av fast sprøytetørket natrium amoxicillin gjorde dem egnet for kommersielt bruk etter sterilisering med etylenoksyd. of solid spray-dried sodium amoxicillin made them suitable for commercial use after sterilization with ethylene oxide.
Under forberedelsen av innmatingen til tørkeren (oppløsnings-trinhet over) ble mikropulverisert amoxicillintrihydrat (aktivitet 845/ag/mg ) blandet i t-butanolløsning bestående av 2,4 1 vann og 1,5 1 t-butanol pr. kg amoxicillin trihydrat ved 25°C. Til denne suspensjon ble tilsatt 1,97N vandig natrium-hydroksyd kontinuerlig til et overskudd på -,:a. 2% (1,23 l/kg) . During the preparation of the feed to the dryer (solution step above), micropulverized amoxicillin trihydrate (activity 845/ag/mg) was mixed in t-butanol solution consisting of 2.4 1 water and 1.5 1 t-butanol per kg amoxicillin trihydrate at 25°C. To this suspension was added 1.97N aqueous sodium hydroxide continuously to an excess of -,:a. 2% (1.23 l/kg) .
Tørke; trinn Produktresultater ^ Bestemt på en vannfri oppløsningsfri bas. ved anvendelse av British Pharmacopeia for å måle forurensning av penicillinsyre og dimere e.l. Tørketrinn -Produkt re sul ta ter Drought; step Product results ^ Determined on an anhydrous solvent-free basis using the British Pharmacopeia to measure contamination of penicillin acid and dimers etc. Drying step - Product results
Bestemt på en vannfri løsningsfri basis ved anvendelse av British Pharmacopeia-fremgangsmåten for å måle forurensning av penicillinsyrebg dimere e.l. Determined on an anhydrous solution-free basis using the British Pharmacopeia method for measuring contamination by penicillin acid bg dimers, etc.
Ved sprøytetørke-trinnet blir trykket variert for å oppnå den ønskede partikkelstørrelse. In the spray drying step, the pressure is varied to achieve the desired particle size.
Anvendelse av sprøytetørke-fremgangsmåten under sterile forhold ved å benytte " trykkdyse .. for å produsere steriltfast natrium amoxicillin gjør at man kan.fylle stoffet direkte i ampuller under sterile forhold.. Application of the spray-drying method under sterile conditions by using a "pressure nozzle .. to produce sterile solid sodium amoxicillin allows one to fill the substance directly into ampoules under sterile conditions..
De antibakterielle egenskaper og kliniske metoder ved bruk av amoxicillin er velkjente i medisinsk litteratur når det gjelder den orale anvendelse av. dets trihydrat. Ved parenteral admini-strering er det ofte foretrukket å injisere en vandig løsning som krever omdannelse av det uoppløslige trihydrat til et meget oppløselig •■ natriumsalt ifølge fremgangsmåten ved foreliggende oppfinnelse. Resultatene av den parenterale aministrering av vandig natrium amoxicillin er beskrevet f.eks. av D. A. Spyker et al., Pharmacokinetics of amoxycillin: "Dose dependence after intravenous, oral and intramuscular admini-stration"; Antimicrobial Agents and Chemotherapy, . 11, 132 The antibacterial properties and clinical methods of using amoxicillin are well known in the medical literature when it comes to the oral application of. its trihydrate. For parenteral administration, it is often preferred to inject an aqueous solution which requires conversion of the insoluble trihydrate into a highly soluble sodium salt according to the method of the present invention. The results of the parenteral administration of aqueous sodium amoxicillin are described e.g. by D. A. Spyker et al., Pharmacokinetics of amoxycillin: "Dose dependence after intravenous, oral and intramuscular administration"; Antimicrobial Agents and Chemotherapy, . 11, 132
(1977) and by-S.A. Hill et al., "Pharmacokinetics of parenter-ally administered amoxycillin", Journal of Infection 2, 320-332 (1980). (1977) and by-S.A. Hill et al., "Pharmacokinetics of parenterally administered amoxycillin", Journal of Infection 2, 320-332 (1980).
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8107247A FR2503710B1 (en) | 1981-04-10 | 1981-04-10 | PROCESS FOR PRODUCING SODIUM SALT OF AMOXICILLIN |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO821174L true NO821174L (en) | 1982-10-11 |
Family
ID=9257255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821174A NO821174L (en) | 1981-04-10 | 1982-04-06 | PROCEDURE FOR THE PREPARATION OF SODIUM AMOXILLIN |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS57179191A (en) |
| KR (1) | KR880001410B1 (en) |
| AU (1) | AU559766B2 (en) |
| BE (1) | BE892451A (en) |
| CA (1) | CA1182108A (en) |
| CH (1) | CH651836A5 (en) |
| DE (1) | DE3213308A1 (en) |
| DK (1) | DK157382A (en) |
| ES (1) | ES511295A0 (en) |
| FI (1) | FI821247L (en) |
| FR (1) | FR2503710B1 (en) |
| GB (1) | GB2096599B (en) |
| GR (1) | GR76106B (en) |
| IE (1) | IE52939B1 (en) |
| IT (1) | IT1148165B (en) |
| LU (1) | LU84007A1 (en) |
| NL (1) | NL8201467A (en) |
| NO (1) | NO821174L (en) |
| NZ (1) | NZ200281A (en) |
| PT (1) | PT74727B (en) |
| SE (1) | SE8202269L (en) |
| YU (1) | YU43132B (en) |
| ZA (1) | ZA822400B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0131147B2 (en) * | 1983-06-10 | 1996-12-04 | Beecham Group p.l.c. | Crystalline amoxycillin salt |
| IT1255716B (en) * | 1992-10-05 | 1995-11-10 | PROCEDURE FOR THE PREPARATION OF STERILE BETA-LACTAMIC ANTIBIOTICS | |
| AT412213B (en) * | 2000-05-30 | 2004-11-25 | Sandoz Ag | METHOD FOR DRYING AMOXICILLIN OR AMOXICILLIN-CONTAINING, ORAL, SOLID PHARMACEUTICAL COMPOSITIONS USING A GAS WITH A DEFINED GAS HUMIDITY |
| CN105055169B (en) * | 2015-07-11 | 2019-01-22 | 鲁南制药集团股份有限公司 | A method of preparing Imipenem and Cilasatin Sodium aseptic powdery |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1471235A (en) * | 1974-09-18 | 1977-04-21 | Beecham Group Ltd | Amoxycillin derivatives |
| GB1527557A (en) * | 1976-07-07 | 1978-10-04 | Beecham Group Ltd | Process for preparing solid sodium amoxycillin |
| GB1576731A (en) * | 1976-08-10 | 1980-10-15 | Beecham Group Ltd | Process for the preparation of sodium amoxycillin |
| EP0012496B1 (en) * | 1978-12-08 | 1983-07-20 | Beecham Group Plc | A process for the preparation of a solid sodium amoxycillin and aqueous solutions thereof |
-
1981
- 1981-04-10 FR FR8107247A patent/FR2503710B1/en not_active Expired
-
1982
- 1982-02-12 AU AU80455/82A patent/AU559766B2/en not_active Expired
- 1982-02-16 GR GR67339A patent/GR76106B/el unknown
- 1982-02-26 YU YU432/82A patent/YU43132B/en unknown
- 1982-03-02 GB GB8206075A patent/GB2096599B/en not_active Expired
- 1982-03-10 BE BE0/207536A patent/BE892451A/en not_active IP Right Cessation
- 1982-03-12 LU LU84007A patent/LU84007A1/en unknown
- 1982-04-06 NO NO821174A patent/NO821174L/en unknown
- 1982-04-06 KR KR8201511A patent/KR880001410B1/en active
- 1982-04-06 DK DK157382A patent/DK157382A/en not_active IP Right Cessation
- 1982-04-06 NL NL8201467A patent/NL8201467A/en not_active Application Discontinuation
- 1982-04-07 ZA ZA822400A patent/ZA822400B/en unknown
- 1982-04-07 FI FI821247A patent/FI821247L/en not_active Application Discontinuation
- 1982-04-07 ES ES511295A patent/ES511295A0/en active Granted
- 1982-04-07 IT IT48188/82A patent/IT1148165B/en active
- 1982-04-08 PT PT74727A patent/PT74727B/en unknown
- 1982-04-08 CA CA000400753A patent/CA1182108A/en not_active Expired
- 1982-04-08 NZ NZ200281A patent/NZ200281A/en unknown
- 1982-04-08 JP JP57057416A patent/JPS57179191A/en active Granted
- 1982-04-08 SE SE8202269A patent/SE8202269L/en not_active Application Discontinuation
- 1982-04-08 CH CH2211/82A patent/CH651836A5/en not_active IP Right Cessation
- 1982-04-08 DE DE19823213308 patent/DE3213308A1/en not_active Withdrawn
- 1982-04-08 IE IE844/82A patent/IE52939B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR880001410B1 (en) | 1988-08-01 |
| YU43132B (en) | 1989-04-30 |
| IT8248188A0 (en) | 1982-04-07 |
| IT1148165B (en) | 1986-11-26 |
| GB2096599A (en) | 1982-10-20 |
| PT74727A (en) | 1982-05-01 |
| NZ200281A (en) | 1984-12-14 |
| DE3213308A1 (en) | 1982-11-11 |
| IE820844L (en) | 1983-10-10 |
| ES8304138A1 (en) | 1983-02-16 |
| DK157382A (en) | 1982-10-11 |
| SE8202269L (en) | 1982-10-11 |
| FR2503710A1 (en) | 1982-10-15 |
| GB2096599B (en) | 1985-01-23 |
| FR2503710B1 (en) | 1985-07-05 |
| PT74727B (en) | 1985-01-08 |
| FI821247L (en) | 1982-10-11 |
| LU84007A1 (en) | 1983-02-22 |
| NL8201467A (en) | 1982-11-01 |
| ZA822400B (en) | 1983-02-23 |
| FI821247A0 (en) | 1982-04-07 |
| JPS57179191A (en) | 1982-11-04 |
| AU559766B2 (en) | 1987-03-19 |
| YU43282A (en) | 1985-06-30 |
| AU8045582A (en) | 1982-10-14 |
| IE52939B1 (en) | 1988-04-13 |
| CH651836A5 (en) | 1985-10-15 |
| ES511295A0 (en) | 1983-02-16 |
| CA1182108A (en) | 1985-02-05 |
| GR76106B (en) | 1984-08-03 |
| BE892451A (en) | 1982-09-10 |
| JPH0219119B2 (en) | 1990-04-27 |
| KR830010116A (en) | 1983-12-26 |
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