NO325523B1 - Fremgangsmate for fremstilling av et kaliumsalt av clavulansyre. - Google Patents
Fremgangsmate for fremstilling av et kaliumsalt av clavulansyre. Download PDFInfo
- Publication number
- NO325523B1 NO325523B1 NO19994793A NO994793A NO325523B1 NO 325523 B1 NO325523 B1 NO 325523B1 NO 19994793 A NO19994793 A NO 19994793A NO 994793 A NO994793 A NO 994793A NO 325523 B1 NO325523 B1 NO 325523B1
- Authority
- NO
- Norway
- Prior art keywords
- liquid
- fluorinated hydrocarbon
- clavulanic acid
- potassium
- salt
- Prior art date
Links
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title claims description 40
- 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 title claims description 40
- 229960003324 clavulanic acid Drugs 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 27
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- -1 amine salt Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 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 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical group [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 3
- GAHCNYHAKKGGHF-UHFFFAOYSA-N 5,5-dimethylhexan-1-amine Chemical compound CC(C)(C)CCCCN GAHCNYHAKKGGHF-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229940090805 clavulanate Drugs 0.000 description 3
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108090000204 Dipeptidase 1 Proteins 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 102000006635 beta-lactamase Human genes 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical class CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000424942 Streptomyces clavuligerus ATCC 27064 Species 0.000 description 1
- 241000187180 Streptomyces sp. Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 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 1
- 229960003022 amoxicillin Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 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
- 230000003749 cleanliness Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 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 1
- 239000002245 particle Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960004659 ticarcillin Drugs 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
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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
-
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9706846.4A GB9706846D0 (en) | 1997-04-04 | 1997-04-04 | Process |
| GBGB9713887.9A GB9713887D0 (en) | 1997-07-02 | 1997-07-02 | Process |
| PCT/EP1998/002137 WO1998045300A1 (en) | 1997-04-04 | 1998-04-02 | A process for the preparation of a metal salt of clavulanic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994793L NO994793L (no) | 1999-10-01 |
| NO994793D0 NO994793D0 (no) | 1999-10-01 |
| NO325523B1 true NO325523B1 (no) | 2008-06-02 |
Family
ID=26311317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994793A NO325523B1 (no) | 1997-04-04 | 1999-10-01 | Fremgangsmate for fremstilling av et kaliumsalt av clavulansyre. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6300495B1 (cs) |
| EP (1) | EP0970087B1 (cs) |
| JP (1) | JP2001521509A (cs) |
| KR (1) | KR100540955B1 (cs) |
| CN (1) | CN1258535C (cs) |
| AR (1) | AR012307A1 (cs) |
| AU (1) | AU736305B2 (cs) |
| BR (1) | BR9808467A (cs) |
| CA (1) | CA2286369C (cs) |
| CO (1) | CO4940460A1 (cs) |
| CZ (1) | CZ298785B6 (cs) |
| DE (1) | DE69838747T2 (cs) |
| DZ (1) | DZ2456A1 (cs) |
| ES (1) | ES2294815T3 (cs) |
| HU (1) | HUP0003621A3 (cs) |
| IL (1) | IL132160A (cs) |
| MA (1) | MA24519A1 (cs) |
| MY (1) | MY120732A (cs) |
| NO (1) | NO325523B1 (cs) |
| NZ (1) | NZ337998A (cs) |
| PE (1) | PE62499A1 (cs) |
| PL (1) | PL190943B1 (cs) |
| TR (1) | TR199902447T2 (cs) |
| TW (1) | TW444016B (cs) |
| WO (1) | WO1998045300A1 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100069635A1 (en) * | 2006-11-29 | 2010-03-18 | Dr. Reddy's Laboratories Ltd. | Rosuvastatin dehydroabietylamine salt |
| CN103833774A (zh) * | 2014-03-21 | 2014-06-04 | 山东新时代药业有限公司 | 一种从克拉维酸钾混粉中回收有效成分的方法 |
| CN109305978A (zh) * | 2017-07-26 | 2019-02-05 | 山东睿鹰先锋制药有限公司 | 一种制备克拉维酸盐的新方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT399155B (de) * | 1992-03-26 | 1995-03-27 | Lek Tovarna Farmacevtskih | Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung |
| SI9300296B (sl) | 1992-06-11 | 1998-06-30 | Smithkline Beecham P.L.C. | Postopek in intermedianti za pripravo klavulanske kisline |
| KR100200239B1 (ko) * | 1992-10-21 | 1999-06-15 | 김충환 | 클라불란산 칼륨염의 제조방법 |
| GB9305565D0 (en) | 1993-03-18 | 1993-05-05 | Smithkline Beecham Plc | Novel compounds and processes |
| US5821364A (en) * | 1993-03-26 | 1998-10-13 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| GB9401969D0 (en) | 1994-02-02 | 1994-03-30 | Smithkline Beecham Plc | Process |
| SI9400107A (en) * | 1994-03-02 | 1995-10-31 | Lek Tovarna Farmacevtskih | New process of the isolation of clavulanic acid and its pharmaceutical salts from fermented broth of streptomyces sp.p 6621 ferm p 2804. |
| JPH11501023A (ja) * | 1995-02-25 | 1999-01-26 | スパーコート リミテッド | クラブラン酸塩 |
| SI9500074A (en) * | 1995-03-10 | 1996-10-31 | Lek Tovarna Farmacevtskih | Process for preparation of alkani salts of clavulanic acid. |
| KR100200242B1 (ko) * | 1995-05-16 | 1999-06-15 | 김충환 | 클라불란산염의 제조 방법 |
| GB9515809D0 (en) * | 1995-08-02 | 1995-10-04 | Smithkline Beecham Plc | Process |
-
1998
- 1998-03-31 DZ DZ980066A patent/DZ2456A1/xx active
- 1998-04-02 CZ CZ0350099A patent/CZ298785B6/cs not_active IP Right Cessation
- 1998-04-02 WO PCT/EP1998/002137 patent/WO1998045300A1/en active IP Right Grant
- 1998-04-02 TR TR1999/02447T patent/TR199902447T2/xx unknown
- 1998-04-02 PL PL336040A patent/PL190943B1/pl unknown
- 1998-04-02 DE DE69838747T patent/DE69838747T2/de not_active Expired - Fee Related
- 1998-04-02 AU AU75242/98A patent/AU736305B2/en not_active Ceased
- 1998-04-02 MY MYPI98001467A patent/MY120732A/en unknown
- 1998-04-02 JP JP54240798A patent/JP2001521509A/ja not_active Ceased
- 1998-04-02 ES ES98922693T patent/ES2294815T3/es not_active Expired - Lifetime
- 1998-04-02 US US09/402,231 patent/US6300495B1/en not_active Expired - Fee Related
- 1998-04-02 BR BR9808467-4A patent/BR9808467A/pt active Search and Examination
- 1998-04-02 HU HU0003621A patent/HUP0003621A3/hu unknown
- 1998-04-02 AR ARP980101494A patent/AR012307A1/es active IP Right Grant
- 1998-04-02 PE PE1998000240A patent/PE62499A1/es not_active Application Discontinuation
- 1998-04-02 MA MA25026A patent/MA24519A1/fr unknown
- 1998-04-02 NZ NZ337998A patent/NZ337998A/en unknown
- 1998-04-02 EP EP98922693A patent/EP0970087B1/en not_active Expired - Lifetime
- 1998-04-02 CN CNB988055074A patent/CN1258535C/zh not_active Expired - Fee Related
- 1998-04-02 KR KR1019997009044A patent/KR100540955B1/ko not_active Expired - Fee Related
- 1998-04-02 CA CA002286369A patent/CA2286369C/en not_active Expired - Fee Related
- 1998-04-02 IL IL13216098A patent/IL132160A/xx not_active IP Right Cessation
- 1998-04-03 TW TW087105104A patent/TW444016B/zh not_active IP Right Cessation
- 1998-04-03 CO CO98018885A patent/CO4940460A1/es unknown
-
1999
- 1999-10-01 NO NO19994793A patent/NO325523B1/no unknown
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