DE1568519B1 - Herstellung von Laurylsulfaten von Tetracyclinen - Google Patents
Herstellung von Laurylsulfaten von TetracyclinenInfo
- Publication number
- DE1568519B1 DE1568519B1 DE1966F0049063 DEF0049063A DE1568519B1 DE 1568519 B1 DE1568519 B1 DE 1568519B1 DE 1966F0049063 DE1966F0049063 DE 1966F0049063 DE F0049063 A DEF0049063 A DE F0049063A DE 1568519 B1 DE1568519 B1 DE 1568519B1
- Authority
- DE
- Germany
- Prior art keywords
- lauryl sulfate
- water
- tetracyclines
- soluble
- tetracycline
- 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- Withdrawn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
- 239000004098 Tetracycline Substances 0.000 title claims description 18
- 235000019364 tetracycline Nutrition 0.000 title claims description 18
- 150000003522 tetracyclines Chemical class 0.000 title claims description 14
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 title claims description 13
- 229940040944 tetracyclines Drugs 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 229960002180 tetracycline Drugs 0.000 claims description 10
- 229930101283 tetracycline Natural products 0.000 claims description 10
- -1 tetracycline compound Chemical class 0.000 claims description 9
- 229940043264 dodecyl sulfate Drugs 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- JFLUGFNRBXKWMW-UHFFFAOYSA-M sodium;dodecyl hydrogen sulfate;dodecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOS(O)(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O JFLUGFNRBXKWMW-UHFFFAOYSA-M 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZPNGGFGGDUNMSP-FMZCEJRJSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O.C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O ZPNGGFGGDUNMSP-FMZCEJRJSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 208000000412 Avitaminosis Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010021135 Hypovitaminosis Diseases 0.000 description 1
- 239000004100 Oxytetracycline Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 235000002201 avitaminosis Nutrition 0.000 description 1
- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 1
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 229960000625 oxytetracycline Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HMEYVGGHISAPJR-IAHYZSEUSA-N rolitetracycline Chemical compound O=C([C@@]1(O)C(O)=C2[C@@H]([C@](C3=CC=CC(O)=C3C2=O)(C)O)C[C@H]1[C@@H](C=1O)N(C)C)C=1C(=O)NCN1CCCC1 HMEYVGGHISAPJR-IAHYZSEUSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 208000030401 vitamin deficiency disease Diseases 0.000 description 1
- 230000008673 vomiting Effects 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES0315101A ES315101A1 (es) | 1965-07-08 | 1965-07-08 | Procedimiento de preparaciën de nuevos derivados de tetraciclina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1568519B1 true DE1568519B1 (de) | 1970-05-21 |
Family
ID=8442667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966F0049063 Withdrawn DE1568519B1 (de) | 1965-07-08 | 1966-04-29 | Herstellung von Laurylsulfaten von Tetracyclinen |
Country Status (5)
| Country | Link |
|---|---|
| BR (1) | BR6680566D0 (enExample) |
| DE (1) | DE1568519B1 (enExample) |
| ES (1) | ES315101A1 (enExample) |
| GB (1) | GB1155037A (enExample) |
| NL (1) | NL6609490A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2144737A (en) * | 1983-08-02 | 1985-03-13 | American Cyanamid Co | Novel alkyl suphate of antibiotics of the tetracycline series |
| DE10114244A1 (de) | 2001-03-22 | 2002-10-02 | Heraeus Kulzer Gmbh & Co Kg | Antibiotikum-/Antibiotika-Zubereitung mit retardierender Wirkstofffreisetzung |
| DE10114364A1 (de) * | 2001-03-22 | 2002-10-02 | Heraeus Kulzer Gmbh & Co Kg | Verfahren zur Herstellung von antibiotischen Kompositen |
| DE10114245A1 (de) * | 2001-03-22 | 2002-10-02 | Heraeus Kulzer Gmbh & Co Kg | Herstellung und Verwendung einer Antibiotikum-/Antibiotika-Zubereitung |
| IS6389A (is) | 2001-08-31 | 2003-03-03 | Heraeus Kulzer Gmbh & Co. Kg | Reynsla af sýklalyfjahúðun skrokka, sem í eru örholrými, og einnig af þannig húðuðum skrokkum og notkun þeirra |
| CN109069423A (zh) * | 2016-03-07 | 2018-12-21 | 双键医药品股份公司 | 亲水性药物的肺部靶向递送 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1098974A (fr) * | 1954-01-08 | 1955-08-29 | Rhone Poulenc Sa | Nouveaux esters de la tétracycline et leur procédé de préparation |
| DE1076682B (de) * | 1958-05-10 | 1960-03-03 | Amalie Schoog Geb Luetzenkirch | Verfahren zur Herstellung von schwerloeslichen Tetracyclinsalzen |
| FR1356997A (fr) * | 1963-02-11 | 1964-04-03 | Soc Ind Fab Antibiotiques Sifa | Nouveaux dérivés de la tétracycline et procédé de préparation |
| BE650353A (enExample) * | 1964-04-16 | 1965-01-11 |
-
1965
- 1965-07-08 ES ES0315101A patent/ES315101A1/es not_active Expired
-
1966
- 1966-04-29 DE DE1966F0049063 patent/DE1568519B1/de not_active Withdrawn
- 1966-06-20 BR BR180566/66A patent/BR6680566D0/pt unknown
- 1966-07-06 NL NL6609490A patent/NL6609490A/xx unknown
- 1966-07-08 GB GB30878/66A patent/GB1155037A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1098974A (fr) * | 1954-01-08 | 1955-08-29 | Rhone Poulenc Sa | Nouveaux esters de la tétracycline et leur procédé de préparation |
| DE1076682B (de) * | 1958-05-10 | 1960-03-03 | Amalie Schoog Geb Luetzenkirch | Verfahren zur Herstellung von schwerloeslichen Tetracyclinsalzen |
| FR1356997A (fr) * | 1963-02-11 | 1964-04-03 | Soc Ind Fab Antibiotiques Sifa | Nouveaux dérivés de la tétracycline et procédé de préparation |
| BE650353A (enExample) * | 1964-04-16 | 1965-01-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6680566D0 (pt) | 1973-12-26 |
| NL6609490A (enExample) | 1967-01-09 |
| ES315101A1 (es) | 1966-01-01 |
| GB1155037A (en) | 1969-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |