CH638218A5 - Kristallisationsverfahren zur gewinnung von natriumcefuroxim. - Google Patents
Kristallisationsverfahren zur gewinnung von natriumcefuroxim. Download PDFInfo
- Publication number
- CH638218A5 CH638218A5 CH40679A CH40679A CH638218A5 CH 638218 A5 CH638218 A5 CH 638218A5 CH 40679 A CH40679 A CH 40679A CH 40679 A CH40679 A CH 40679A CH 638218 A5 CH638218 A5 CH 638218A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sodium
- cefuroxime
- aqueous solution
- crystallization medium
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 title description 6
- 229960001668 cefuroxime Drugs 0.000 title description 6
- 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
- 229910052708 sodium Inorganic materials 0.000 title description 2
- 239000011734 sodium Substances 0.000 title description 2
- URDOHUPGIOGTKV-JTBFTWTJSA-M Cefuroxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 URDOHUPGIOGTKV-JTBFTWTJSA-M 0.000 claims description 50
- 238000002425 crystallisation Methods 0.000 claims description 28
- 230000008025 crystallization Effects 0.000 claims description 28
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 229910001415 sodium ion Inorganic materials 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 15
- 159000000000 sodium salts Chemical class 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000011081 inoculation Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 239000001540 sodium lactate Substances 0.000 claims description 2
- 229940005581 sodium lactate Drugs 0.000 claims description 2
- 235000011088 sodium lactate Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000008156 Ringer's lactate solution Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- JFPVXVDWJQMJEE-SWWZKJRFSA-N 55268-75-2 Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-SWWZKJRFSA-N 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 alkyl ketone Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB188178 | 1978-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH638218A5 true CH638218A5 (de) | 1983-09-15 |
Family
ID=9729694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH40679A CH638218A5 (de) | 1978-01-17 | 1979-01-16 | Kristallisationsverfahren zur gewinnung von natriumcefuroxim. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4298732A (en, 2012) |
| JP (1) | JPS54117492A (en, 2012) |
| CH (1) | CH638218A5 (en, 2012) |
| DE (1) | DE2901730A1 (en, 2012) |
| FR (1) | FR2414509A1 (en, 2012) |
| IT (1) | IT1162442B (en, 2012) |
| NL (1) | NL189762C (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4341777A (en) * | 1979-09-10 | 1982-07-27 | Glaxo Group Limited | Cephalosporin antibiotic |
| JPS6011491A (ja) * | 1983-03-04 | 1985-01-21 | Shionogi & Co Ltd | セフアロチンナトリウムの結晶性凍結乾燥粉末の製造法 |
| GB8320520D0 (en) * | 1983-07-29 | 1983-09-01 | Glaxo Group Ltd | Chemical process |
| JPH0288824U (en, 2012) * | 1988-12-27 | 1990-07-13 | ||
| AU1234999A (en) * | 1997-11-10 | 1999-05-31 | Gist-Brocades B.V. | Crystallization of beta-lactam compounds |
| KR100396464B1 (ko) * | 2000-12-14 | 2003-09-02 | 씨제이 주식회사 | 세푸록심의 나트륨염을 함유하는 약학적 조성물의 안정화방법 |
| US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
| CN100384853C (zh) * | 2004-05-10 | 2008-04-30 | 河北张药股份有限公司 | 替卡西林钠的合成方法 |
| CN101475579B (zh) * | 2009-01-20 | 2011-02-09 | 广州白云山天心制药股份有限公司 | 一种稳定的头孢呋辛钠及其制备方法 |
| CN102295653A (zh) * | 2010-06-28 | 2011-12-28 | 广州白云山制药股份有限公司广州白云山化学制药厂 | 头孢呋辛钠的一步法回收制备方法 |
| CN102617604A (zh) * | 2012-02-24 | 2012-08-01 | 天津大学 | 一种耦合反应结晶制备头孢呋辛钠的方法 |
| CN103374019B (zh) * | 2012-04-12 | 2016-08-03 | 珠海保税区丽珠合成制药有限公司 | 一种头孢呋肟钠的制备方法 |
| CN103102357B (zh) * | 2013-02-21 | 2016-01-13 | 广东立国制药有限公司 | 一种头孢呋辛钠的合成方法 |
| CN112979082B (zh) * | 2021-03-01 | 2023-01-03 | 安徽金轩科技有限公司 | 一种呋喃铵盐生产废水回收再利用工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714154A (en) * | 1970-12-24 | 1973-01-30 | Lilly Co Eli | Recovery of cephalothin salts |
| US3974153A (en) * | 1971-05-14 | 1976-08-10 | Glaxo Laboratories Limited | 7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids |
| GB1453049A (en) * | 1973-08-21 | 1976-10-20 | Glaxo Lab Ltd | Cephalosporing antibiotics |
-
1979
- 1979-01-15 FR FR7900886A patent/FR2414509A1/fr active Granted
- 1979-01-15 IT IT47641/79A patent/IT1162442B/it active
- 1979-01-16 CH CH40679A patent/CH638218A5/de not_active IP Right Cessation
- 1979-01-17 NL NLAANVRAGE7900356,A patent/NL189762C/xx not_active IP Right Cessation
- 1979-01-17 JP JP306979A patent/JPS54117492A/ja active Granted
- 1979-01-17 DE DE19792901730 patent/DE2901730A1/de active Granted
-
1980
- 1980-03-03 US US06/126,523 patent/US4298732A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7900356A (nl) | 1979-07-19 |
| FR2414509B1 (en, 2012) | 1983-07-08 |
| DE2901730A1 (de) | 1979-07-19 |
| IT1162442B (it) | 1987-04-01 |
| NL189762C (nl) | 1993-07-16 |
| JPS638115B2 (en, 2012) | 1988-02-19 |
| IT7947641A0 (it) | 1979-01-15 |
| JPS54117492A (en) | 1979-09-12 |
| US4298732A (en) | 1981-11-03 |
| FR2414509A1 (fr) | 1979-08-10 |
| NL189762B (nl) | 1993-02-16 |
| DE2901730C2 (en, 2012) | 1992-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |