EP0831803A1 - Sorbinsäure haltige hydrogele - Google Patents
Sorbinsäure haltige hydrogeleInfo
- Publication number
- EP0831803A1 EP0831803A1 EP96917458A EP96917458A EP0831803A1 EP 0831803 A1 EP0831803 A1 EP 0831803A1 EP 96917458 A EP96917458 A EP 96917458A EP 96917458 A EP96917458 A EP 96917458A EP 0831803 A1 EP0831803 A1 EP 0831803A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- sorbic acid
- hydrogel
- pharmaceutical preparations
- weight
- acid
- 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- Withdrawn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
- 235000010199 sorbic acid Nutrition 0.000 title claims abstract description 15
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000000017 hydrogel Substances 0.000 title claims abstract description 14
- 229940075582 sorbic acid Drugs 0.000 title claims abstract description 14
- 239000004334 sorbic acid Substances 0.000 title claims abstract description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 208000002874 Acne Vulgaris Diseases 0.000 description 3
- 206010000496 acne Diseases 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical compound CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006253 efflorescence Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Definitions
- the invention relates to pharmaceutical preparations in the form of a hydrogel, which are characterized in that they contain sorbic acid, if appropriate in combination with a polyhydric alcohol and / or a polyhydric ether, as the sole active ingredients.
- these preparation forms can contain polyhydric alcohols and / or polyhydric ethers, such as, for example, ethylene glycol, propylene glycol, glycerol or a polyoxyalkylene, which serve to prevent the skin from drying out and to keep it supple (humefectant, emolliant and softening agents) (Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., VCH-Verlagsgesellschaft mbH, D-69451 Weinheim (DE), 1993, Volume AlO, p lOlff, Volume A21, p 579ff and Volume A22, p 163)
- these additives can also serve as agents for enhancing the penetration of the active ingredients (enhancers).
- Suitable polyvalent alcohols and / or polyvalent ethers for the pharmaceutical preparations according to the invention are preferably physiologically harmless, liquid substances of these classes of substances, as are usually used in such preparations.
- Such compounds are, for example, those of the general formula II
- n is a number from 1 to 12 (preferably 1 to 8) and
- R is a hydrogen atom, a methyl group or, if n is 1, also a
- Suitable alcohols or ethers of the general formula I are, for example, ethylene glycol, propylene glycol, glycerol, diethylene glycol, triethylene glycol, dipropylene glycol or tripropylene glycol. These are substances which are also used in pharmaceutical preparations intended for topical application as enhancers for the active ingredients used in the preparations (see, for example, EP-A 0 165 696, WO 88/01496 and DE-A 2 515 594).
- the pharmaceutical preparations according to the invention can also contain, for example, cyclic polyols or polyethers such as dimethyl isosorbide or glycol ethers such as diglycol dimethyl ether as polyhydric alcohols or polyhydric ethers.
- cyclic polyols or polyethers such as dimethyl isosorbide or glycol ethers such as diglycol dimethyl ether as polyhydric alcohols or polyhydric ethers.
- glycol ethers such as diglycol dimethyl ether as polyhydric alcohols or polyhydric ethers.
- propylene glycol has proven to be particularly suitable.
- the pharmaceutical preparations according to the invention in the form of a hydrogel can contain, for example, 0.05 to 2.5% by weight and preferably 0.1 to 1.0% by weight of sorbic acid and 0 to 30% by weight and preferably 5 to 20% by weight of a polyvalent Contain alcohol and / or a polyvalent ether.
- Suitable thickeners are, for example, gel-forming polysaccharides and proteins such as gelatin, agar-agar, pectins, and dextrins or in particular polyacrylates, such as those of the Carbopol® type (Goodrich Chem., Cleveland, USA).
- a suitable preparation in the form of a hydrogel can have, for example, the following composition:
- Carbopol® 980 0.5 2.0%
- sorbic acid 12.0 g of propylene glycol and 76.55 g of purified water are mixed, heated to 35 ° C. and the sorbic acid is dissolved with stirring. The solution is then cooled to 20 ° C., 1.0 g of Carbopol® are added and the mixture is homogenized. A solution of 10.0 g of sodium hydroxide in 10.25 g of purified water is then added to the mixture and the mixture is homogenized until the gel structure has completely formed.
- the developed hydrogel base with sorbic acid also shows a strong antimicrobial activity and a clear influence on the inflammation process in acne, which goes far beyond the expected vehicle effect of a preserved hydrogel base.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19520838 | 1995-05-31 | ||
| DE19520838 | 1995-05-31 | ||
| PCT/EP1996/002300 WO1996038135A1 (de) | 1995-05-31 | 1996-05-30 | Sorbinsäure haltige hydrogele |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0831803A1 true EP0831803A1 (de) | 1998-04-01 |
Family
ID=7763859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96917458A Withdrawn EP0831803A1 (de) | 1995-05-31 | 1996-05-30 | Sorbinsäure haltige hydrogele |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0831803A1 (cs) |
| JP (1) | JPH11506441A (cs) |
| KR (1) | KR19990022143A (cs) |
| CN (1) | CN1185735A (cs) |
| AU (1) | AU6002796A (cs) |
| CA (1) | CA2222566A1 (cs) |
| CZ (1) | CZ374797A3 (cs) |
| HU (1) | HUP9801745A3 (cs) |
| IS (1) | IS4606A (cs) |
| PL (1) | PL323598A1 (cs) |
| TR (1) | TR199701463T1 (cs) |
| WO (1) | WO1996038135A1 (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9826656D0 (en) | 1998-12-03 | 1999-01-27 | Novartis Ag | Organic compounds |
| BE1023757B1 (nl) * | 2016-06-30 | 2017-07-12 | Yun NV | Bewaring van micro-organismen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6333314A (ja) * | 1986-07-29 | 1988-02-13 | Sansho Seiyaku Kk | 外用剤 |
| US5013769A (en) * | 1988-08-22 | 1991-05-07 | Medipro Sciences Limited | Method of making a hydrogel-forming wound dressing or skin coating material |
-
1996
- 1996-05-30 JP JP8536180A patent/JPH11506441A/ja active Pending
- 1996-05-30 EP EP96917458A patent/EP0831803A1/de not_active Withdrawn
- 1996-05-30 CN CN96194272A patent/CN1185735A/zh active Pending
- 1996-05-30 HU HU9801745A patent/HUP9801745A3/hu unknown
- 1996-05-30 TR TR97/01463T patent/TR199701463T1/xx unknown
- 1996-05-30 KR KR1019970708622A patent/KR19990022143A/ko not_active Withdrawn
- 1996-05-30 CZ CZ973747A patent/CZ374797A3/cs unknown
- 1996-05-30 AU AU60027/96A patent/AU6002796A/en not_active Abandoned
- 1996-05-30 CA CA002222566A patent/CA2222566A1/en not_active Abandoned
- 1996-05-30 WO PCT/EP1996/002300 patent/WO1996038135A1/de not_active Ceased
- 1996-05-30 PL PL96323598A patent/PL323598A1/xx unknown
-
1997
- 1997-10-31 IS IS4606A patent/IS4606A/is unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9638135A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL323598A1 (en) | 1998-04-14 |
| IS4606A (is) | 1997-10-31 |
| JPH11506441A (ja) | 1999-06-08 |
| CA2222566A1 (en) | 1996-12-05 |
| KR19990022143A (ko) | 1999-03-25 |
| AU6002796A (en) | 1996-12-18 |
| CZ374797A3 (cs) | 1998-04-15 |
| TR199701463T1 (en) | 1998-02-21 |
| HUP9801745A2 (hu) | 1998-12-28 |
| HUP9801745A3 (en) | 2000-04-28 |
| CN1185735A (zh) | 1998-06-24 |
| WO1996038135A1 (de) | 1996-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19971001 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 19990730 |