DE2557493A1 - Stabile salben mit breitem wirkungsspektrum und ihr herstellungsverfahren - Google Patents
Stabile salben mit breitem wirkungsspektrum und ihr herstellungsverfahrenInfo
- Publication number
- DE2557493A1 DE2557493A1 DE19752557493 DE2557493A DE2557493A1 DE 2557493 A1 DE2557493 A1 DE 2557493A1 DE 19752557493 DE19752557493 DE 19752557493 DE 2557493 A DE2557493 A DE 2557493A DE 2557493 A1 DE2557493 A1 DE 2557493A1
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- dichlorobenzyloxy
- deoxy
- imidazole
- emulsion
- 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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002674 ointment Substances 0.000 claims description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 229960005205 prednisolone Drugs 0.000 claims description 19
- -1 2,4-dichlorobenzyloxy Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000000839 emulsion Substances 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- 239000007900 aqueous suspension Substances 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000003246 corticosteroid Substances 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000005662 Paraffin oil Substances 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 201000004624 Dermatitis Diseases 0.000 description 5
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 229940121375 antifungal agent Drugs 0.000 description 5
- 229960005091 chloramphenicol Drugs 0.000 description 5
- 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 5
- 239000012071 phase Substances 0.000 description 5
- 239000002569 water oil cream Substances 0.000 description 5
- 229920001214 Polysorbate 60 Polymers 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940053050 neomycin sulfate Drugs 0.000 description 3
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 3
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 206010007134 Candida infections Diseases 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 241000130764 Tinea Species 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 229940082500 cetostearyl alcohol Drugs 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 2
- QSWSKDXFOIOXKW-UHFFFAOYSA-N 1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1=CNC=N1 QSWSKDXFOIOXKW-UHFFFAOYSA-N 0.000 description 1
- QUAFTMJUVQDZHE-UHFFFAOYSA-N 3-(4-chloroanilino)-6-hydroxy-9-methylcarbazole-1,4-dione Chemical compound ClC1=CC=C(C=C1)NC1=CC(C=2N(C3=CC=C(C=C3C=2C1=O)O)C)=O QUAFTMJUVQDZHE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- RIYITFZDKHVMRQ-UHFFFAOYSA-N 7-iodoquinoline Chemical compound C1=CC=NC2=CC(I)=CC=C21 RIYITFZDKHVMRQ-UHFFFAOYSA-N 0.000 description 1
- IBSXNLSAPHQZFZ-CLFAGFIQSA-N 9-[(Z)-octadec-9-enoyl]oxynonyl (Z)-octadec-9-enoate Chemical compound C(CCCCCCC\C=C/CCCCCCCC)(=O)OCCCCCCCCCOC(CCCCCCC\C=C/CCCCCCCC)=O IBSXNLSAPHQZFZ-CLFAGFIQSA-N 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- 206010014199 Eczema infected Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 208000010195 Onychomycosis Diseases 0.000 description 1
- 206010034016 Paronychia Diseases 0.000 description 1
- 241000029132 Paronychia Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 201000010618 Tinea cruris Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 208000007287 cheilitis Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 208000005005 intertrigo Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 206010033072 otitis externa Diseases 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 201000005882 tinea unguium Diseases 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI558A HU169761B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-12-20 | 1974-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2557493A1 true DE2557493A1 (de) | 1976-06-24 |
Family
ID=11000969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752557493 Withdrawn DE2557493A1 (de) | 1974-12-20 | 1975-12-19 | Stabile salben mit breitem wirkungsspektrum und ihr herstellungsverfahren |
Country Status (10)
-
1974
- 1974-12-20 HU HURI558A patent/HU169761B/hu unknown
-
1975
- 1975-12-17 NL NL7514722A patent/NL7514722A/xx not_active Application Discontinuation
- 1975-12-18 SE SE7514348A patent/SE418245B/xx unknown
- 1975-12-18 FR FR7538896A patent/FR2294688A1/fr active Granted
- 1975-12-19 DD DD190360A patent/DD122641A5/xx unknown
- 1975-12-19 DK DK582875A patent/DK582875A/da not_active Application Discontinuation
- 1975-12-19 AT AT967675A patent/AT339485B/de active
- 1975-12-19 DE DE19752557493 patent/DE2557493A1/de not_active Withdrawn
- 1975-12-19 BE BE162955A patent/BE836888A/xx not_active IP Right Cessation
- 1975-12-22 GB GB5231475A patent/GB1474510A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HU169761B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-28 |
| ATA967675A (de) | 1977-02-15 |
| GB1474510A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-25 |
| DD122641A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-20 |
| BE836888A (fr) | 1976-04-16 |
| SE7514348L (sv) | 1976-06-21 |
| NL7514722A (nl) | 1976-06-22 |
| FR2294688A1 (fr) | 1976-07-16 |
| AT339485B (de) | 1977-10-25 |
| SE418245B (sv) | 1981-05-18 |
| DK582875A (da) | 1976-06-21 |
| FR2294688B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |