FI56015C - Foerfarande foer foerbaettrad framstaellning av alkalimetallsalt av 7-(2'-tienylacetamido)cefalosporansyra fraon en vattenloesning daerav - Google Patents
Foerfarande foer foerbaettrad framstaellning av alkalimetallsalt av 7-(2'-tienylacetamido)cefalosporansyra fraon en vattenloesning daerav Download PDFInfo
- Publication number
- FI56015C FI56015C FI3653/71A FI365371A FI56015C FI 56015 C FI56015 C FI 56015C FI 3653/71 A FI3653/71 A FI 3653/71A FI 365371 A FI365371 A FI 365371A FI 56015 C FI56015 C FI 56015C
- Authority
- FI
- Finland
- Prior art keywords
- cephalothin
- salt
- sodium
- solution
- aqueous solution
- Prior art date
Links
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 40
- 239000012535 impurity Substances 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229910052783 alkali metal Inorganic materials 0.000 description 16
- -1 alkali metal salt Chemical class 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229960000603 cefalotin Drugs 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229940083555 sodium cephalothin Drugs 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 102000007327 Protamines Human genes 0.000 description 4
- 108010007568 Protamines Proteins 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229940001447 lactate Drugs 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229940048914 protamine Drugs 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 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 description 2
- 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 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 description 2
- 239000001521 potassium lactate Substances 0.000 description 2
- 235000011085 potassium lactate Nutrition 0.000 description 2
- 229960001304 potassium lactate Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001540 sodium lactate Substances 0.000 description 2
- 235000011088 sodium lactate Nutrition 0.000 description 2
- 229940005581 sodium lactate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical class NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical class CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical group O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10138370A | 1970-12-24 | 1970-12-24 | |
| US10138370 | 1970-12-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56015B FI56015B (fi) | 1979-07-31 |
| FI56015C true FI56015C (fi) | 1981-01-05 |
Family
ID=22284373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3653/71A FI56015C (fi) | 1970-12-24 | 1971-12-22 | Foerfarande foer foerbaettrad framstaellning av alkalimetallsalt av 7-(2'-tienylacetamido)cefalosporansyra fraon en vattenloesning daerav |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3714154A (de) |
| JP (1) | JPS5246238B1 (de) |
| AT (1) | AT310947B (de) |
| BE (1) | BE776842A (de) |
| BG (1) | BG24674A3 (de) |
| CA (1) | CA925864A (de) |
| CS (1) | CS190362B2 (de) |
| CY (1) | CY872A (de) |
| DK (1) | DK142287B (de) |
| ES (1) | ES398305A1 (de) |
| FI (1) | FI56015C (de) |
| FR (1) | FR2119747A5 (de) |
| GB (1) | GB1318690A (de) |
| HK (1) | HK78376A (de) |
| HU (1) | HU162401B (de) |
| IE (1) | IE35922B1 (de) |
| IL (1) | IL38478A (de) |
| LU (1) | LU64519A1 (de) |
| MY (1) | MY7700002A (de) |
| NL (1) | NL163790C (de) |
| NO (1) | NO139223C (de) |
| OA (1) | OA03935A (de) |
| RO (1) | RO58634A (de) |
| SE (1) | SE376920B (de) |
| YU (1) | YU39895B (de) |
| ZA (1) | ZA718355B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012380A (en) * | 1974-12-10 | 1977-03-15 | Eli Lilly And Company | 7-Acylamino-3-acyl-2(or 3)cephems |
| FR2414509A1 (fr) * | 1978-01-17 | 1979-08-10 | Glaxo Group Ltd | Procede de cristallisation de cefuroxime sodique |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218318A (en) * | 1962-08-31 | 1965-11-16 | Lilly Co Eli | 7-heterocyclic-substituted-acylamido cephalosporins |
| US3351597A (en) * | 1966-11-23 | 1967-11-07 | Lilly Co Eli | Process for acylating 7-amino cephalosporanic acid |
-
1970
- 1970-12-24 US US00101383A patent/US3714154A/en not_active Expired - Lifetime
-
1971
- 1971-06-24 YU YU3251/71A patent/YU39895B/xx unknown
- 1971-12-14 ZA ZA718355A patent/ZA718355B/xx unknown
- 1971-12-16 SE SE7116121A patent/SE376920B/xx unknown
- 1971-12-17 BE BE776842A patent/BE776842A/xx not_active IP Right Cessation
- 1971-12-17 NL NL7117414.A patent/NL163790C/xx not_active IP Right Cessation
- 1971-12-20 GB GB5906871A patent/GB1318690A/en not_active Expired
- 1971-12-20 CY CY872A patent/CY872A/xx unknown
- 1971-12-21 HU HUEI397A patent/HU162401B/hu unknown
- 1971-12-22 BG BG019299A patent/BG24674A3/xx unknown
- 1971-12-22 OA OA54446A patent/OA03935A/xx unknown
- 1971-12-22 FI FI3653/71A patent/FI56015C/fi active
- 1971-12-23 AT AT1107371A patent/AT310947B/de not_active IP Right Cessation
- 1971-12-23 NO NO4825/71A patent/NO139223C/no unknown
- 1971-12-23 IE IE1641/71A patent/IE35922B1/xx unknown
- 1971-12-23 CS CS718964A patent/CS190362B2/cs unknown
- 1971-12-23 ES ES398305A patent/ES398305A1/es not_active Expired
- 1971-12-23 DK DK631671AA patent/DK142287B/da unknown
- 1971-12-23 CA CA130994A patent/CA925864A/en not_active Expired
- 1971-12-24 FR FR7146605A patent/FR2119747A5/fr not_active Expired
- 1971-12-24 LU LU64519D patent/LU64519A1/xx unknown
- 1971-12-24 JP JP47004066A patent/JPS5246238B1/ja active Pending
- 1971-12-24 RO RO69184A patent/RO58634A/ro unknown
- 1971-12-29 IL IL38478A patent/IL38478A/xx unknown
-
1976
- 1976-12-09 HK HK783/76*UA patent/HK78376A/xx unknown
-
1977
- 1977-12-30 MY MY2/77A patent/MY7700002A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100211915B1 (ko) | 5-메틸테트라히드로폴산의 에난티오머 분할방법 | |
| GB2213819A (en) | Salts of 7 - [alpha-(2 aminothiazol-4-yl)-alpha-(Z)-methoxyimino-acetamido]-3-[(1-methyl-1-pyrrolidino) methyl]-3-cephem-4-carboxylate | |
| US3280118A (en) | N-(7-2'-thienylacetamidoceph-3-em-3-ylmethyl)-pyridinium-4-carboxylate salts and process | |
| JP5771152B2 (ja) | セフジニル酸式複塩化合物を含む経口投与製剤およびその調製方法 | |
| FI56015C (fi) | Foerfarande foer foerbaettrad framstaellning av alkalimetallsalt av 7-(2'-tienylacetamido)cefalosporansyra fraon en vattenloesning daerav | |
| JP2012513957A5 (de) | ||
| CN105440054B (zh) | 一种制备头孢硫脒的工艺 | |
| DE1445835B2 (de) | Verfahren zur herstellung von cephalosporinderivaten | |
| KR930007809B1 (ko) | 항생물질유도체의 정제방법 | |
| NO151748B (no) | Fremgangsmaate for fremstilling av en farmasoeytisk akseptabel, ikke-solvatert, vannfri, gamma-krystallinsk form av natriim-7-(d-alfa-formyloksy-alfa-fenylacetamido)-3-(1-metyl-1h-tetrazol-5-yltiometyl-3-cefem-4-karboksylat | |
| IL46650A (en) | Antibiotic compositions containing sodium 7-(d-2 formyloxy-2-phenyl-acetamido)-3-(1 methyl-1h-tetrazole-5-ylthiomethyl)-3-cephem-4 carboxylate | |
| CN106008554A (zh) | 一种头孢曲松钠无菌粉的制备方法及产品 | |
| NO167098B (no) | Modulaer beskyttelsesstruktur for undervannsinstallasjoner. | |
| US4390694A (en) | Method for preparing stable crystals of salt of Ceftizoxime | |
| FI62311C (fi) | Foerfarande foer framstaellning av kristallint natrium- och kaiumcefalexinmonohydrat | |
| SU565628A3 (ru) | Способ очистки сорбиновой кислоты | |
| US3830809A (en) | Bis-dicyclohexylamine n-carbisobutoxycephalosporin c | |
| CA1282407C (en) | Crystalline cephem carboxylic acid addition salt | |
| CN111233894B (zh) | 一种头孢妥仑匹酯δ3异构体的制备方法 | |
| Jacobs et al. | Syntheses in the Cinchona Series. II. Quaternary Salts. | |
| CN109134331A (zh) | 阿奇霉素基因毒性杂质的合成方法 | |
| US4458070A (en) | Process for the manufacture of crystalline sodium cefoperazone | |
| RU2382790C2 (ru) | Способ получения динатриевой соли гемигептагидрата 7-{[2-аминотиазол-4-ил)-2-син-метоксиимино]ацетамидо}-3-{[(2,5-дигидро-6-гидрокси-2-метил-5-оксо-1,2,4-триазин-3-ил)тио]метил}-3-цефем-4-карбоновой кислоты | |
| ITMI20060422A1 (it) | Procedimento diretto per la produzione del dicloridrato di un amminoacido | |
| SU439989A1 (ru) | Способ выделени щелочно-металлических солей 7-/2"-тиенилацетамидо/-цефалоспорановой кислоты |