DE2708046A1 - Verfahren zur herstellung von kristallinem calcium-di-clavulanat-dihydrat und diese verbindung enthaltende arzneimittel - Google Patents
Verfahren zur herstellung von kristallinem calcium-di-clavulanat-dihydrat und diese verbindung enthaltende arzneimittelInfo
- Publication number
- DE2708046A1 DE2708046A1 DE19772708046 DE2708046A DE2708046A1 DE 2708046 A1 DE2708046 A1 DE 2708046A1 DE 19772708046 DE19772708046 DE 19772708046 DE 2708046 A DE2708046 A DE 2708046A DE 2708046 A1 DE2708046 A1 DE 2708046A1
- Authority
- DE
- Germany
- Prior art keywords
- calcium
- salt
- clavulanate
- solution
- dihydrate
- 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.)
- Withdrawn
Links
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims description 24
- 239000011575 calcium Substances 0.000 title claims description 24
- 229910052791 calcium Inorganic materials 0.000 title claims description 24
- 229940090805 clavulanate Drugs 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 20
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 CLAVULANATE DIHYDRATE Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 26
- 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 19
- 239000003729 cation exchange resin Substances 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 159000000007 calcium salts Chemical class 0.000 claims description 15
- 229960003324 clavulanic acid Drugs 0.000 claims description 14
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000013078 crystal Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 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
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 229930182555 Penicillin Natural products 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 2
- 229960003022 amoxicillin Drugs 0.000 claims description 2
- 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 claims description 2
- 229960000723 ampicillin Drugs 0.000 claims description 2
- 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 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 229940124587 cephalosporin Drugs 0.000 claims description 2
- 150000001780 cephalosporins Chemical class 0.000 claims description 2
- 150000004683 dihydrates Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 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 claims description 2
- 229940049954 penicillin Drugs 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 description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 7
- 229940023913 cation exchange resins Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000011001 backwashing Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229960003669 carbenicillin Drugs 0.000 description 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 1
- RTYJTGSCYUUYAL-YCAHSCEMSA-L carbenicillin disodium Chemical compound [Na+].[Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)C(C([O-])=O)C1=CC=CC=C1 RTYJTGSCYUUYAL-YCAHSCEMSA-L 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 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 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960004659 ticarcillin Drugs 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
- ZBBCUBMBMZNEME-QBGWIPKPSA-L ticarcillin disodium Chemical compound [Na+].[Na+].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 ZBBCUBMBMZNEME-QBGWIPKPSA-L 0.000 description 1
- 150000004684 trihydrates Chemical class 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
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7544/76A GB1561395A (en) | 1976-02-26 | 1976-02-26 | -lactam antibiotic |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2708046A1 true DE2708046A1 (de) | 1977-09-01 |
Family
ID=9835161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772708046 Withdrawn DE2708046A1 (de) | 1976-02-26 | 1977-02-24 | Verfahren zur herstellung von kristallinem calcium-di-clavulanat-dihydrat und diese verbindung enthaltende arzneimittel |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS52105193A (enExample) |
| AU (1) | AU504721B2 (enExample) |
| BE (1) | BE851872A (enExample) |
| CA (1) | CA1079736A (enExample) |
| CH (1) | CH624957A5 (enExample) |
| DE (1) | DE2708046A1 (enExample) |
| DK (1) | DK86177A (enExample) |
| FR (1) | FR2342289A1 (enExample) |
| GB (1) | GB1561395A (enExample) |
| IE (1) | IE44704B1 (enExample) |
| NL (1) | NL7702036A (enExample) |
| SE (1) | SE7702078L (enExample) |
| ZA (1) | ZA771089B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0562583A1 (de) * | 1992-03-26 | 1993-09-29 | LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d. | Neue Alkylendiammonium-diclavulanat-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR245221A1 (es) * | 1984-10-27 | 1993-12-30 | Beecham Group Plc | Un metodo para la produccion de acido clavulanico por fermentacion de s. clavuligerus |
| 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 |
| EP3236940B1 (en) | 2014-12-23 | 2020-02-05 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
| US9549947B2 (en) | 2014-12-23 | 2017-01-24 | Ardelyx, Inc. | Pharmaceutical compositions for treating hyperkalemia |
-
1976
- 1976-02-26 GB GB7544/76A patent/GB1561395A/en not_active Expired
-
1977
- 1977-02-23 ZA ZA00771089A patent/ZA771089B/xx unknown
- 1977-02-23 FR FR7705257A patent/FR2342289A1/fr active Granted
- 1977-02-24 DE DE19772708046 patent/DE2708046A1/de not_active Withdrawn
- 1977-02-24 SE SE7702078A patent/SE7702078L/xx not_active Application Discontinuation
- 1977-02-24 AU AU22643/77A patent/AU504721B2/en not_active Expired
- 1977-02-25 IE IE415/77A patent/IE44704B1/en unknown
- 1977-02-25 NL NL7702036A patent/NL7702036A/xx not_active Application Discontinuation
- 1977-02-25 CH CH242177A patent/CH624957A5/de not_active IP Right Cessation
- 1977-02-25 DK DK86177A patent/DK86177A/da not_active Application Discontinuation
- 1977-02-25 BE BE175302A patent/BE851872A/xx unknown
- 1977-02-25 CA CA272,740A patent/CA1079736A/en not_active Expired
- 1977-02-26 JP JP2076577A patent/JPS52105193A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0562583A1 (de) * | 1992-03-26 | 1993-09-29 | LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d. | Neue Alkylendiammonium-diclavulanat-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52105193A (en) | 1977-09-03 |
| AU504721B2 (en) | 1979-10-25 |
| SE7702078L (sv) | 1977-08-27 |
| GB1561395A (en) | 1980-02-20 |
| ZA771089B (en) | 1978-01-25 |
| DK86177A (da) | 1977-08-27 |
| IE44704B1 (en) | 1982-02-24 |
| AU2264377A (en) | 1978-08-31 |
| NL7702036A (nl) | 1977-08-30 |
| BE851872A (fr) | 1977-08-25 |
| IE44704L (en) | 1977-08-26 |
| FR2342289A1 (fr) | 1977-09-23 |
| CA1079736A (en) | 1980-06-17 |
| CH624957A5 (en) | 1981-08-31 |
| FR2342289B1 (enExample) | 1980-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |