DE2430752A1 - Verfahren zum stabilisieren von alphakristallen hoeherer fettsaeureester des thiamphenicols - Google Patents
Verfahren zum stabilisieren von alphakristallen hoeherer fettsaeureester des thiamphenicolsInfo
- Publication number
- DE2430752A1 DE2430752A1 DE2430752A DE2430752A DE2430752A1 DE 2430752 A1 DE2430752 A1 DE 2430752A1 DE 2430752 A DE2430752 A DE 2430752A DE 2430752 A DE2430752 A DE 2430752A DE 2430752 A1 DE2430752 A1 DE 2430752A1
- Authority
- DE
- Germany
- Prior art keywords
- crystals
- thiamphenicol
- fatty acid
- acid ester
- higher fatty
- 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- Withdrawn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
- 239000013078 crystal Substances 0.000 title claims description 81
- 229960003053 thiamphenicol Drugs 0.000 title claims description 39
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 title claims description 31
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 28
- 239000000194 fatty acid Substances 0.000 title claims description 28
- 229930195729 fatty acid Natural products 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 18
- 230000000087 stabilizing effect Effects 0.000 title claims description 6
- 150000004665 fatty acids Chemical class 0.000 title description 4
- -1 fatty acid esters Chemical class 0.000 claims description 29
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical group CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 7
- 229940070765 laurate Drugs 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 4
- 229930016911 cinnamic acid Natural products 0.000 claims description 4
- 235000013985 cinnamic acid Nutrition 0.000 claims description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 4
- 229940105132 myristate Drugs 0.000 claims description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- ROGLXKYZAOFGQO-AOYPEHQESA-N [(1r,2r)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-methylsulfonylphenyl)propyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)O[C@@H]([C@@H](CO)NC(=O)C(Cl)Cl)C1=CC=C(S(C)(=O)=O)C=C1 ROGLXKYZAOFGQO-AOYPEHQESA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960001805 chloramphenicol palmitate Drugs 0.000 description 1
- PXKHGMGELZGJQE-ILBGXUMGSA-N chloramphenicol palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 PXKHGMGELZGJQE-ILBGXUMGSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 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
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007712 rapid solidification Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000010792 warming 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7441273A JPS5024248A (nl) | 1973-07-03 | 1973-07-03 | |
| JP7441373A JPS5024249A (nl) | 1973-07-03 | 1973-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2430752A1 true DE2430752A1 (de) | 1975-01-23 |
Family
ID=26415559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2430752A Withdrawn DE2430752A1 (de) | 1973-07-03 | 1974-06-26 | Verfahren zum stabilisieren von alphakristallen hoeherer fettsaeureester des thiamphenicols |
Country Status (6)
| Country | Link |
|---|---|
| DE (1) | DE2430752A1 (nl) |
| ES (1) | ES427894A1 (nl) |
| FR (1) | FR2235920B1 (nl) |
| GB (1) | GB1475419A (nl) |
| NL (1) | NL178872C (nl) |
| SE (1) | SE7408730L (nl) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787842A (fr) * | 1971-08-25 | 1972-12-18 | Sumito Chemical Cy Ltd | Procede de preparation d'une suspension aqueuse de cristaux stables du type non beta d'esters d'acides gras superieurs du chloramphenicol |
-
1974
- 1974-06-26 DE DE2430752A patent/DE2430752A1/de not_active Withdrawn
- 1974-07-02 GB GB2921174A patent/GB1475419A/en not_active Expired
- 1974-07-02 SE SE7408730A patent/SE7408730L/xx unknown
- 1974-07-02 FR FR7423028A patent/FR2235920B1/fr not_active Expired
- 1974-07-02 ES ES427894A patent/ES427894A1/es not_active Expired
- 1974-07-03 NL NLAANVRAGE7409020,A patent/NL178872C/nl not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES427894A1 (es) | 1976-12-16 |
| NL178872C (nl) | 1986-06-02 |
| FR2235920B1 (nl) | 1978-01-27 |
| NL178872B (nl) | 1986-01-02 |
| GB1475419A (en) | 1977-06-01 |
| FR2235920A1 (nl) | 1975-01-31 |
| SE7408730L (nl) | 1975-01-07 |
| NL7409020A (nl) | 1975-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |