ZA200006946B - Process for preparing crystalline salts of amoxycillin. - Google Patents
Process for preparing crystalline salts of amoxycillin. Download PDFInfo
- Publication number
- ZA200006946B ZA200006946B ZA200006946A ZA200006946A ZA200006946B ZA 200006946 B ZA200006946 B ZA 200006946B ZA 200006946 A ZA200006946 A ZA 200006946A ZA 200006946 A ZA200006946 A ZA 200006946A ZA 200006946 B ZA200006946 B ZA 200006946B
- Authority
- ZA
- South Africa
- Prior art keywords
- amoxycillin
- process according
- salt
- solution
- sodium
- Prior art date
Links
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical class 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 title claims description 65
- 229960003022 amoxicillin Drugs 0.000 title claims description 55
- 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 title claims description 55
- 150000003839 salts Chemical class 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- -1 alkali metal salt Chemical class 0.000 claims description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 24
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 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 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 19
- 239000011734 sodium Substances 0.000 claims description 19
- 239000000725 suspension Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 238000004090 dissolution Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ROFDDOQLDAQFRA-UHFFFAOYSA-N 2,2-diethyl-3-oxobutanedioic acid Chemical compound CCC(CC)(C(O)=O)C(=O)C(O)=O ROFDDOQLDAQFRA-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 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 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 239000003781 beta lactamase inhibitor Substances 0.000 description 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- 229960003324 clavulanic acid Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical class CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8755498P | 1998-06-01 | 1998-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006946B true ZA200006946B (en) | 2002-01-28 |
Family
ID=22205864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006946A ZA200006946B (en) | 1998-06-01 | 2000-11-27 | Process for preparing crystalline salts of amoxycillin. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1086109A4 (no) |
| JP (1) | JP2002517398A (no) |
| KR (1) | KR20010043942A (no) |
| CN (1) | CN1182138C (no) |
| AU (1) | AU760934B2 (no) |
| BR (1) | BR9910804A (no) |
| CA (1) | CA2333943A1 (no) |
| HU (1) | HUP0102008A3 (no) |
| IL (1) | IL139736A (no) |
| NO (1) | NO20006073L (no) |
| NZ (1) | NZ508179A (no) |
| PL (1) | PL344348A1 (no) |
| TR (1) | TR200003517T2 (no) |
| WO (1) | WO1999062910A1 (no) |
| ZA (1) | ZA200006946B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6294199B1 (en) | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
| US6878386B1 (en) | 1999-04-13 | 2005-04-12 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate |
| WO2006072577A1 (en) * | 2005-01-07 | 2006-07-13 | Sandoz Ag | Process for preparing granulates comprising amoxicillin |
| CN101633663B (zh) * | 2009-08-28 | 2011-12-21 | 沈阳顺旺动物药业有限公司 | 一种青霉素类钠、钾盐的合成方法 |
| WO2011158133A1 (en) * | 2010-06-16 | 2011-12-22 | Vardhman Chemtech Limited | Improved process for preparing amoxicillin sodium |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8606871A1 (es) * | 1985-10-21 | 1986-06-01 | Antibioticos Sa | Un procedimiento de preparacion de amoxicilina sodica |
| IT1255716B (it) * | 1992-10-05 | 1995-11-10 | Procedimento per la preparazione di antibiotici beta-lattamici sterili | |
| TW347383B (en) * | 1995-10-26 | 1998-12-11 | Biochemie Gmbh | A process for the production of a crystalline sodium salt of amoxicillin in ethanol as solvent |
-
1999
- 1999-06-01 AU AU43216/99A patent/AU760934B2/en not_active Ceased
- 1999-06-01 CA CA002333943A patent/CA2333943A1/en not_active Abandoned
- 1999-06-01 PL PL99344348A patent/PL344348A1/xx not_active Application Discontinuation
- 1999-06-01 KR KR1020007013513A patent/KR20010043942A/ko not_active Application Discontinuation
- 1999-06-01 JP JP2000552121A patent/JP2002517398A/ja not_active Withdrawn
- 1999-06-01 HU HU0102008A patent/HUP0102008A3/hu unknown
- 1999-06-01 CN CNB998069272A patent/CN1182138C/zh not_active Expired - Fee Related
- 1999-06-01 EP EP99955267A patent/EP1086109A4/en not_active Withdrawn
- 1999-06-01 IL IL13973699A patent/IL139736A/en not_active IP Right Cessation
- 1999-06-01 WO PCT/US1999/011991 patent/WO1999062910A1/en not_active Application Discontinuation
- 1999-06-01 BR BR9910804-6A patent/BR9910804A/pt not_active IP Right Cessation
- 1999-06-01 NZ NZ508179A patent/NZ508179A/xx unknown
- 1999-06-01 TR TR2000/03517T patent/TR200003517T2/xx unknown
-
2000
- 2000-11-27 ZA ZA200006946A patent/ZA200006946B/en unknown
- 2000-11-30 NO NO20006073A patent/NO20006073L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ508179A (en) | 2002-10-25 |
| KR20010043942A (ko) | 2001-05-25 |
| NO20006073D0 (no) | 2000-11-30 |
| EP1086109A1 (en) | 2001-03-28 |
| EP1086109A4 (en) | 2001-12-19 |
| IL139736A0 (en) | 2002-02-10 |
| PL344348A1 (en) | 2001-11-05 |
| AU760934B2 (en) | 2003-05-22 |
| CN1304412A (zh) | 2001-07-18 |
| TR200003517T2 (tr) | 2001-06-21 |
| WO1999062910A1 (en) | 1999-12-09 |
| HUP0102008A3 (en) | 2002-07-29 |
| AU4321699A (en) | 1999-12-20 |
| BR9910804A (pt) | 2001-02-13 |
| NO20006073L (no) | 2000-11-30 |
| CN1182138C (zh) | 2004-12-29 |
| JP2002517398A (ja) | 2002-06-18 |
| IL139736A (en) | 2004-02-19 |
| CA2333943A1 (en) | 1999-12-09 |
| HUP0102008A2 (hu) | 2001-12-28 |
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