HU180161B - Process for preparing crystalline,stable prostaglandin f down 2alpha with a melting point over 35 c from contaminated prostaglandin f down 2alpha containing 50-98% prostaglandin f down 2alpha - Google Patents
Process for preparing crystalline,stable prostaglandin f down 2alpha with a melting point over 35 c from contaminated prostaglandin f down 2alpha containing 50-98% prostaglandin f down 2alpha Download PDFInfo
- Publication number
- HU180161B HU180161B HU192080A HU192080A HU180161B HU 180161 B HU180161 B HU 180161B HU 192080 A HU192080 A HU 192080A HU 192080 A HU192080 A HU 192080A HU 180161 B HU180161 B HU 180161B
- Authority
- HU
- Hungary
- Prior art keywords
- prostaglandin
- solution
- water
- alpha
- acid
- Prior art date
Links
- 238000002844 melting Methods 0.000 title claims abstract description 16
- 230000008018 melting Effects 0.000 title claims abstract description 16
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000243 solution Substances 0.000 claims abstract description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000012535 impurity Substances 0.000 claims abstract description 9
- 239000000284 extract Substances 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000011780 sodium chloride Substances 0.000 claims abstract description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 4
- 150000007519 polyprotic acids Polymers 0.000 claims abstract description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000003180 prostaglandins Chemical class 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- IYGXEHDCSOYNKY-RZHHZEQLSA-N Dinoprost tromethamine Chemical compound OCC(N)(CO)CO.CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O IYGXEHDCSOYNKY-RZHHZEQLSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229960001342 dinoprost Drugs 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 230000004048 modification Effects 0.000 abstract description 9
- 238000012986 modification Methods 0.000 abstract description 9
- 239000013078 crystal Substances 0.000 abstract description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 5
- PXGPLTODNUVGFL-UHFFFAOYSA-N prostaglandin F2alpha Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CC=CCCCC(O)=O PXGPLTODNUVGFL-UHFFFAOYSA-N 0.000 abstract 4
- 150000008043 acidic salts Chemical class 0.000 abstract 2
- 239000013543 active substance Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012445 acidic reagent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 238000005169 Debye-Scherrer Methods 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- KLFJWYRWDZQUFQ-UHFFFAOYSA-N bromo dihydrogen phosphate Chemical class OP(O)(=O)OBr KLFJWYRWDZQUFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU192080A HU180161B (en) | 1980-08-01 | 1980-08-01 | Process for preparing crystalline,stable prostaglandin f down 2alpha with a melting point over 35 c from contaminated prostaglandin f down 2alpha containing 50-98% prostaglandin f down 2alpha |
| DE19813129637 DE3129637A1 (de) | 1980-08-01 | 1981-07-28 | Kristallines, stabiles prostaglandin f 2(alpha) mit eiem schmelzpunkt oberhalb von 35(grad)c, dessen herstellung sowie diese kristallmodifikation enthaltende praeparate |
| FR8114832A FR2487828A1 (fr) | 1980-08-01 | 1981-07-30 | Procede de preparation de prostaglandine f2a stable, cristalline, fondant au-dessus de 35 oc a partir de prostaglandine f2a impure contenant de 50 a 98 % de prostaglandine f2a |
| ES504993A ES8204419A1 (es) | 1980-08-01 | 1981-07-31 | Procedimiento de preparar prostaglandina cristalina y esta- ble |
| JP11943681A JPS5764664A (en) | 1980-08-01 | 1981-07-31 | Purification of prostaglandin f2 alpha |
| AT337681A AT378767B (de) | 1980-08-01 | 1981-07-31 | Verfahren zur herstellung von kristallinem, stabilem prostaglandin f 2alpha |
| GR65683A GR74277B (enrdf_load_stackoverflow) | 1980-08-01 | 1981-07-31 | |
| CH497381A CH648826A5 (de) | 1980-08-01 | 1981-07-31 | Verfahren zur herstellung von kristallinem prostaglandin f2alpha von einem schmelzpunkt ueber 35 c. |
| DK344081A DK156829C (da) | 1980-08-01 | 1981-07-31 | Fremgangsmaade til fremstilling af krystallinsk, stabilt prostaglandin f2alfa |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU192080A HU180161B (en) | 1980-08-01 | 1980-08-01 | Process for preparing crystalline,stable prostaglandin f down 2alpha with a melting point over 35 c from contaminated prostaglandin f down 2alpha containing 50-98% prostaglandin f down 2alpha |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180161B true HU180161B (en) | 1983-02-28 |
Family
ID=10956846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU192080A HU180161B (en) | 1980-08-01 | 1980-08-01 | Process for preparing crystalline,stable prostaglandin f down 2alpha with a melting point over 35 c from contaminated prostaglandin f down 2alpha containing 50-98% prostaglandin f down 2alpha |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5764664A (enrdf_load_stackoverflow) |
| AT (1) | AT378767B (enrdf_load_stackoverflow) |
| CH (1) | CH648826A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3129637A1 (enrdf_load_stackoverflow) |
| DK (1) | DK156829C (enrdf_load_stackoverflow) |
| ES (1) | ES8204419A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2487828A1 (enrdf_load_stackoverflow) |
| GR (1) | GR74277B (enrdf_load_stackoverflow) |
| HU (1) | HU180161B (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49100059A (enrdf_load_stackoverflow) * | 1973-02-03 | 1974-09-20 | ||
| US3941886A (en) * | 1973-09-21 | 1976-03-02 | Alza Corporation | Pharmaceutical compositions containing crystalline racemic 9α, 11α, 15(S)-trihydroxy-5-cis, 13-trans-prostadienoic acid |
-
1980
- 1980-08-01 HU HU192080A patent/HU180161B/hu unknown
-
1981
- 1981-07-28 DE DE19813129637 patent/DE3129637A1/de active Granted
- 1981-07-30 FR FR8114832A patent/FR2487828A1/fr active Granted
- 1981-07-31 GR GR65683A patent/GR74277B/el unknown
- 1981-07-31 ES ES504993A patent/ES8204419A1/es not_active Expired
- 1981-07-31 CH CH497381A patent/CH648826A5/de not_active IP Right Cessation
- 1981-07-31 AT AT337681A patent/AT378767B/de not_active IP Right Cessation
- 1981-07-31 DK DK344081A patent/DK156829C/da not_active IP Right Cessation
- 1981-07-31 JP JP11943681A patent/JPS5764664A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES504993A0 (es) | 1982-05-16 |
| DK156829C (da) | 1990-02-19 |
| DE3129637C2 (enrdf_load_stackoverflow) | 1991-05-29 |
| GR74277B (enrdf_load_stackoverflow) | 1984-06-21 |
| ES8204419A1 (es) | 1982-05-16 |
| DK344081A (da) | 1982-02-02 |
| DE3129637A1 (de) | 1982-05-13 |
| ATA337681A (de) | 1985-02-15 |
| DK156829B (da) | 1989-10-09 |
| CH648826A5 (de) | 1985-04-15 |
| FR2487828A1 (fr) | 1982-02-05 |
| FR2487828B1 (enrdf_load_stackoverflow) | 1984-01-06 |
| JPS5764664A (en) | 1982-04-19 |
| AT378767B (de) | 1985-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI103973B (fi) | Menetelmä epäpuhtaan klavulaanihapon puhdistamiseksi | |
| NO171556B (no) | Fremgangsmaate for fremstilling av azitromycin dihydrat | |
| US4775751A (en) | Process for cephalexin hydrochloride alcoholates | |
| IE56488B1 (en) | Crystalline cephem-acid addition salts and process for their preparation | |
| US4456753A (en) | Process for the manufacture of highly crystalline sodium cefoperazone | |
| US2520098A (en) | Process for preparing pure, crystalline penicillin salts | |
| HU180161B (en) | Process for preparing crystalline,stable prostaglandin f down 2alpha with a melting point over 35 c from contaminated prostaglandin f down 2alpha containing 50-98% prostaglandin f down 2alpha | |
| CN110114333B (zh) | 赖氨酸乙酰水杨酸盐·甘氨酸颗粒的改进合成 | |
| HU202536B (en) | Process for producing 7-imidazolidinone derivative of cefem derivative antibiotics | |
| US3061515A (en) | Methane sulfonates of telomycins | |
| Cornforth et al. | 330. A synthesis of acylamidomalondialdehydes | |
| US3405165A (en) | Sulfonic acid compound | |
| SU925251A3 (ru) | Способ получени кристаллической формы D-конфигурации полуторной натриевой соли 7 @ -/ @ -карбокси- @ -(п-оксифенил) ацетамидо/-7 @ -метокси-3-(1-метилтетразол-5-ил)-тиометил-1-оксадетиа-3-цефем-4-карбоновой кислоты | |
| Dudley et al. | Preparation and Properties of Gallium Lactate1 | |
| US4656309A (en) | Preparation of alpha-pivaloyl-substituted acetic acid esters | |
| SU860705A3 (ru) | Способ получени кристаллической формы D-конфигурации диаммониевой соли 7 - -карбокси- -( -оксифенил)ацетамидо/-7 -метокси-3-(1-метилтетразол-5-ил)-тиометил-1-оксадетиа-3-цефем-4-карбоновой кислоты | |
| JPS606958B2 (ja) | 抗生物質の精製法 | |
| US2969357A (en) | Penicillin salts of amino salicylates | |
| FI69297C (fi) | Dikaliumpentapropionat och foerfarande foer dess framstaellning | |
| US2875227A (en) | Ephedrine salts of 7-carboethoxy-3-acetylthioheptanoic acid | |
| US2538081A (en) | Penicillin-diisopropylether complex and preparation thereof | |
| Clutterbuck et al. | Studies in the Biochemistry of Micro-organisms. Part XVI—On the production from Glucose by Penicillium Spiculisporum Lehman of a new polybasic fatty acid, C17 H28 O6 (the lactone of γ-hydroxy-βδ-dicarboxypentadecoic acid) | |
| EP0018813B1 (en) | Crystalline germaazaspirodiones,their preparation and their use in the preparation of germaazaspiranes | |
| US4263454A (en) | Lithium ribonate, lithium arabonate and the preparation and purification of these salts | |
| IL37224A (en) | Pharmaceutical preparations containing 3 - acyloxypropyl - 2 - trimethyl ammonium (noble phosphates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |