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 (cs) |
| JP (1) | JPS5246238B1 (cs) |
| AT (1) | AT310947B (cs) |
| BE (1) | BE776842A (cs) |
| BG (1) | BG24674A3 (cs) |
| CA (1) | CA925864A (cs) |
| CS (1) | CS190362B2 (cs) |
| CY (1) | CY872A (cs) |
| DK (1) | DK142287B (cs) |
| ES (1) | ES398305A1 (cs) |
| FI (1) | FI56015C (cs) |
| FR (1) | FR2119747A5 (cs) |
| GB (1) | GB1318690A (cs) |
| HK (1) | HK78376A (cs) |
| HU (1) | HU162401B (cs) |
| IE (1) | IE35922B1 (cs) |
| IL (1) | IL38478A (cs) |
| LU (1) | LU64519A1 (cs) |
| MY (1) | MY7700002A (cs) |
| NL (1) | NL163790C (cs) |
| NO (1) | NO139223C (cs) |
| OA (1) | OA03935A (cs) |
| RO (1) | RO58634A (cs) |
| SE (1) | SE376920B (cs) |
| YU (1) | YU39895B (cs) |
| ZA (1) | ZA718355B (cs) |
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 NL NL7117414.A patent/NL163790C/xx not_active IP Right Cessation
- 1971-12-17 BE BE776842A patent/BE776842A/xx not_active IP Right Cessation
- 1971-12-20 CY CY872A patent/CY872A/xx unknown
- 1971-12-20 GB GB5906871A patent/GB1318690A/en not_active Expired
- 1971-12-21 HU HUEI397A patent/HU162401B/hu unknown
- 1971-12-22 OA OA54446A patent/OA03935A/xx unknown
- 1971-12-22 BG BG019299A patent/BG24674A3/xx unknown
- 1971-12-22 FI FI3653/71A patent/FI56015C/fi active
- 1971-12-23 CA CA130994A patent/CA925864A/en not_active Expired
- 1971-12-23 DK DK631671AA patent/DK142287B/da unknown
- 1971-12-23 CS CS718964A patent/CS190362B2/cs unknown
- 1971-12-23 AT AT1107371A patent/AT310947B/de not_active IP Right Cessation
- 1971-12-23 ES ES398305A patent/ES398305A1/es not_active Expired
- 1971-12-23 IE IE1641/71A patent/IE35922B1/xx unknown
- 1971-12-23 NO NO4825/71A patent/NO139223C/no unknown
- 1971-12-24 JP JP47004066A patent/JPS5246238B1/ja active Pending
- 1971-12-24 RO RO69184A patent/RO58634A/ro unknown
- 1971-12-24 FR FR7146605A patent/FR2119747A5/fr not_active Expired
- 1971-12-24 LU LU64519D patent/LU64519A1/xx 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
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