FI67222C - Foerfarande foer rening av klavulansyra och saosom mellanprodukt anvaendbara aminsalt av klavulansyra samt foerfarande foer framstaellning av dessa - Google Patents
Foerfarande foer rening av klavulansyra och saosom mellanprodukt anvaendbara aminsalt av klavulansyra samt foerfarande foer framstaellning av dessa Download PDFInfo
- Publication number
- FI67222C FI67222C FI802590A FI802590A FI67222C FI 67222 C FI67222 C FI 67222C FI 802590 A FI802590 A FI 802590A FI 802590 A FI802590 A FI 802590A FI 67222 C FI67222 C FI 67222C
- Authority
- FI
- Finland
- Prior art keywords
- clavulanic acid
- tert
- acetone
- butylamine
- klavulansyra
- Prior art date
Links
- 101100148710 Clarkia breweri SAMT gene Proteins 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 88
- 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 claims description 60
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims description 58
- 229960003324 clavulanic acid Drugs 0.000 claims description 48
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000012453 solvate Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- -1 alkaline earth metal salt Chemical class 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 229940090805 clavulanate Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 230000009102 absorption Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical class CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- JMRXTGCDVQLAFM-JSYANWSFSA-M lithium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Li+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 JMRXTGCDVQLAFM-JSYANWSFSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000007614 solvation Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- NTZZEBUPDUXPKO-UHFFFAOYSA-N 2-methylpropan-2-amine Chemical compound CC(C)(C)N.CC(C)(C)N NTZZEBUPDUXPKO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000926 separation method Methods 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
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7929544 | 1979-08-24 | ||
| GB7929544 | 1979-08-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI802590A7 FI802590A7 (fi) | 1981-02-25 |
| FI67222B FI67222B (fi) | 1984-10-31 |
| FI67222C true FI67222C (fi) | 1985-02-11 |
Family
ID=10507413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802590A FI67222C (fi) | 1979-08-24 | 1980-08-18 | Foerfarande foer rening av klavulansyra och saosom mellanprodukt anvaendbara aminsalt av klavulansyra samt foerfarande foer framstaellning av dessa |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4647659A (index.php) |
| EP (1) | EP0026044B1 (index.php) |
| JP (2) | JPS5634685A (index.php) |
| KR (1) | KR860000343B1 (index.php) |
| AU (1) | AU535198B2 (index.php) |
| CA (1) | CA1157862A (index.php) |
| DE (1) | DE3063683D1 (index.php) |
| DK (1) | DK156069C (index.php) |
| ES (1) | ES494431A0 (index.php) |
| FI (1) | FI67222C (index.php) |
| GR (1) | GR69870B (index.php) |
| HK (1) | HK1086A (index.php) |
| HU (1) | HU185619B (index.php) |
| IE (1) | IE50047B1 (index.php) |
| IL (1) | IL60885A (index.php) |
| MY (1) | MY8500999A (index.php) |
| NO (1) | NO165241C (index.php) |
| NZ (1) | NZ194703A (index.php) |
| PL (1) | PL139811B1 (index.php) |
| ZA (1) | ZA805206B (index.php) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2200355B (en) | 1987-01-29 | 1990-08-01 | Beecham Group Plc | Potassium clavulanate |
| ES2010143A6 (es) † | 1989-03-01 | 1989-10-16 | Pharma Mar S A Pharmar | Un nuevo procedimiento de obtencion del acido z(2r,5r)-3-(2-hiadroxietiliden)-7- oxo-4-oxa-1-azabiciclo(3,2,0) -heptano-2-carboxilico y de sales estares farmaceutiacamente aceptables del mismo,a partir de caldos de fermentacion de streptomyces, sp. |
| JPH0457085U (index.php) * | 1990-09-14 | 1992-05-15 | ||
| JPH0569557U (ja) * | 1992-02-26 | 1993-09-21 | 東京電機工業株式會社 | 固体蓄熱装置 |
| AT400033B (de) * | 1992-03-10 | 1995-09-25 | Biochemie Gmbh | Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben |
| 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 |
| GB9222841D0 (en) * | 1992-10-31 | 1992-12-16 | Smithkline Beecham Plc | Novel process |
| GB2282810B (en) * | 1992-06-11 | 1997-02-26 | Smithkline Beecham Plc | Preparation or purification of clavulanic acid |
| AT1447U1 (de) * | 1992-06-11 | 1997-05-26 | Smithkline Beecham Plc | Neue salze von clavulansäure |
| AT475U1 (de) * | 1992-06-11 | 1995-11-27 | Smithkline Beecham Plc | Verfahren zur herstellung von clavulansaeure |
| SI9200139A (en) * | 1992-07-08 | 1994-03-31 | Lek Tovarna Farmacevtskih | New inclusion complex of clavulanic acid with hydrophylyc and hydropholyc beta-cyclodextrin derivates for production of them |
| KR100200239B1 (ko) * | 1992-10-21 | 1999-06-15 | 김충환 | 클라불란산 칼륨염의 제조방법 |
| AT1446U1 (de) * | 1992-10-31 | 1997-05-26 | Smithkline Beecham Plc | Verfahren zur herstellung und/oder reinigung von clavulansäure |
| GB9305565D0 (en) * | 1993-03-18 | 1993-05-05 | Smithkline Beecham Plc | Novel compounds and processes |
| US5760218A (en) * | 1993-03-26 | 1998-06-02 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| NZ263564A (en) * | 1993-03-26 | 1995-12-21 | Gist Brocades Nv | Tertiary, tertiary diamine mono and di salts of clavulanic acid; purification of clavulanic acid |
| US5821364A (en) * | 1993-03-26 | 1998-10-13 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| DE4318916A1 (de) * | 1993-06-07 | 1994-12-08 | Bayer Ag | Cyclobutylazole |
| EP0658558B1 (en) | 1993-11-17 | 2001-01-24 | Biochemie Gesellschaft M.B.H. | Separation of cephalosporin isomers |
| GB9401969D0 (en) * | 1994-02-02 | 1994-03-30 | Smithkline Beecham Plc | Process |
| GB9426261D0 (en) | 1994-12-24 | 1995-02-22 | Spurcourt Ltd | Clavulanic acid salts |
| GB9500977D0 (en) | 1995-01-19 | 1995-03-08 | Smithkline Beecham Plc | Novel process |
| AU691727B2 (en) * | 1995-02-25 | 1998-05-21 | Spurcourt Limited | Clavulanic acid salts |
| SI9500134B (sl) | 1995-04-20 | 2004-04-30 | Lek, | Postopek za pripravo čistih alkalijskih soli klavulanske kisline |
| KR100200242B1 (ko) * | 1995-05-16 | 1999-06-15 | 김충환 | 클라불란산염의 제조 방법 |
| GB9515809D0 (en) * | 1995-08-02 | 1995-10-04 | Smithkline Beecham Plc | Process |
| JPH09152148A (ja) * | 1995-09-29 | 1997-06-10 | Tokyo Denki Kogyo Kk | 蓄熱式空調装置 |
| ZA975198B (en) | 1996-06-13 | 1997-12-15 | Smithkline Beecham Corp | Improved process for preparing potassium clavulanate. |
| AT404728B (de) * | 1996-11-27 | 1999-02-25 | Biochemie Gmbh | Verfahren zur herstellung von clavulansäure-aminsalzen |
| CN1308682A (zh) * | 1998-07-03 | 2001-08-15 | Dsm公司 | 在低浓度游离氨基酸下生产棒酸的发酵工艺 |
| CN1198940C (zh) * | 1998-09-29 | 2005-04-27 | Dsm公司 | 在控制氨水平条件下的棒酸发酵 |
| GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| ES2177391B1 (es) * | 2000-04-19 | 2004-08-16 | Felipe Lopez Oliva Muñoz | Protesis de disco cervical. |
| KR100827898B1 (ko) | 2000-05-13 | 2008-05-07 | 스미스클라인비이참피이엘시이 | 클라불란산의 염의 정제 방법 |
| CN105384758B (zh) * | 2015-12-01 | 2018-05-01 | 国药集团威奇达药业有限公司 | 克拉维酸胺盐的制备方法 |
| 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 |
| CN108822134B (zh) * | 2018-04-25 | 2021-06-25 | 国药集团威奇达药业有限公司 | 克拉维酸叔丁胺盐的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1508977A (en) * | 1974-04-20 | 1978-04-26 | Beecham Group Ltd | Beta-lactam antibiotic from streptomyces clavuligerus |
| IE41109B1 (en) * | 1974-04-20 | 1979-10-24 | Beecham Group Ltd | Novel -lactam antibiotic from streptomyces clavuligerus |
| GB1543563A (en) * | 1975-02-07 | 1979-04-04 | Glaxo Lab Ltd | Beta-lactam antibiotic in purified form |
| FR2368276A1 (fr) * | 1975-02-07 | 1978-05-19 | Glaxo Lab Ltd | Nouvel antibiotique provenant de streptomyces clavuligerus et son procede de preparation |
| GB1578739A (en) * | 1976-07-23 | 1980-11-05 | Beecham Group Ltd | Amine salts of clavulanic acid methods for their preparation and compositions containing them |
| GB1572912A (en) * | 1977-01-19 | 1980-08-06 | Beecham Group Ltd | Clavulanic acid esters |
| US4255332A (en) * | 1977-09-01 | 1981-03-10 | Beecham Group Limited | Process for the preparation of potassium clavulanate from lithium clavulanate |
-
1980
- 1980-08-15 DE DE8080302814T patent/DE3063683D1/de not_active Expired
- 1980-08-15 EP EP80302814A patent/EP0026044B1/en not_active Expired
- 1980-08-18 FI FI802590A patent/FI67222C/fi not_active IP Right Cessation
- 1980-08-19 NZ NZ194703A patent/NZ194703A/xx unknown
- 1980-08-20 IL IL60885A patent/IL60885A/xx unknown
- 1980-08-21 AU AU61632/80A patent/AU535198B2/en not_active Expired
- 1980-08-21 GR GR62713A patent/GR69870B/el unknown
- 1980-08-22 ES ES494431A patent/ES494431A0/es active Granted
- 1980-08-22 IE IE1777/80A patent/IE50047B1/en not_active IP Right Cessation
- 1980-08-22 NO NO802498A patent/NO165241C/no unknown
- 1980-08-22 DK DK363080A patent/DK156069C/da not_active IP Right Cessation
- 1980-08-22 ZA ZA00805206A patent/ZA805206B/xx unknown
- 1980-08-22 CA CA000358979A patent/CA1157862A/en not_active Expired
- 1980-08-22 HU HU802090A patent/HU185619B/hu unknown
- 1980-08-25 PL PL1980226397A patent/PL139811B1/pl unknown
- 1980-08-25 KR KR1019800003345A patent/KR860000343B1/ko not_active Expired
- 1980-08-25 JP JP11764480A patent/JPS5634685A/ja active Granted
-
1985
- 1985-01-22 US US06/693,122 patent/US4647659A/en not_active Expired - Lifetime
- 1985-12-30 MY MY999/85A patent/MY8500999A/xx unknown
-
1986
- 1986-01-02 HK HK10/86A patent/HK1086A/en not_active IP Right Cessation
-
1989
- 1989-11-10 JP JP1293786A patent/JPH02167286A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: BEECHAM GROUP LIMITED |