DK173547B1 - Salicylic acid-containing agent for the local treatment of skin diseases with dandruff in the human and veterinary medicine - Google Patents
Salicylic acid-containing agent for the local treatment of skin diseases with dandruff in the human and veterinary medicine Download PDFInfo
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- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
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- A—HUMAN NECESSITIES
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- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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Abstract
Description
i DK 173547 B1in DK 173547 B1
Salicylsyreholdigt middel til lokalbehandling af hudsygdomme med skæl Inden for den humane og den veterinære medicinSalicylic acid-containing agent for the local treatment of skin diseases with dandruff In the field of human and veterinary medicine
Den foreliggende opfindelse angår et salicylsyreholdigt middel til lokalterapi 5 af hudsygdomme med skæl inden for human- og veterinærmedicinen. Til disse hudsygdomme med skæl hører f. eks. psoriasis, tinea amiantacea og se-borrhoea sicca.The present invention relates to a salicylic acid containing agent for local therapy 5 of skin diseases with scales in the human and veterinary medicine. These skin diseases with dandruff include, for example, psoriasis, tinea amiantacea and se-borrhoea sicca.
F. eks. er det ffa E. Mutschler, "Arzneimittelwirkungen", Wissenschaftliche 10 Verlagsgeseilschaft, Stuttgart 1975, side 373 kendt, at salicylsyre bevirker en løsnen af skæl og blødgøring af hommaterialet og kommer til anvendelse i form af salicylvaseline, salicylspiritus og salicylkollodium. Endvidere anvendes til behandling af de førnævnte hudsygdomme blandt andet salicylsvinefedt, salicylleucerin og salicylgel.For example, it is known by E. Mutschler, "Arzneimittelwirkungen", Wissenschaftliche 10 Verlagsgeseilschaft, Stuttgart 1975, page 373, that salicylic acid causes a release of dandruff and softening of the home material and is used in the form of salicylvaseline, salicylspiridus and salicylclodium. Also used to treat the aforementioned skin diseases include salicylic pig fat, salicylleucerin and salicyl gel.
1515
Derudover er det også kendt, at opløsninger af salicylsyre i fede olier, såsom olivenolie, ricinusolie og andre, anvendes til behandling af førnævnte hudsygdomme.In addition, it is also known that salicylic acid solutions in fatty oils, such as olive oil, castor oil and others, are used to treat the aforementioned skin diseases.
20 Endvidere kendes fra EP-A-0 063 870 et betændeiseshæmmende salvepræparat til dermatologiske anvendelser, som i almindelighed indeholder et betændelseshæmmende middel i et salvegrundlag. Salvegrundlaget består af et triglycerid med middellang kæde, en carboxyvinylpolymer og vand i vægtforholdet (1-25): (0,3-3): (75 - 99).Furthermore, EP-A-0 063 870 discloses an anti-inflammatory ointment preparation for dermatological applications, which generally contains an anti-inflammatory agent in an ointment base. The ointment base consists of a medium chain triglyceride, a carboxyvinyl polymer and water in weight ratio (1-25): (0.3-3): (75 - 99).
2525
Fra DE-A-762 726 kendes opløsningsmidler eller opløsningsformidlere, ved hjælp af hvilke opløseligheden af salicylsyre kan forøges i fedtstoffer og olier med over 10%. Hertil hører højere molekylære alifatiske alkoholer og alkoholblandinger (Ce-Ci4) såsom fedtalkoholer og estere af sådanne alkoholer 30 med flervalente alkoholer, som indeholder mindst en fri hydroxylgruppe.DE-A-762 726 discloses solvents or solvents by which the solubility of salicylic acid can be increased in fats and oils by more than 10%. These include higher molecular aliphatic alcohols and alcohol mixtures (Ce-C14) such as fatty alcohols and esters of such alcohols with multivalent alcohols containing at least one free hydroxyl group.
Ifølge Veroffentlichung af U. Adams et al. (Pharm. Ind., bind 44, nr. 6,1982, side 625-629) optages salicylsyre i salver, der dannes som gele og som salvegrundlag indeholder triglycerider med middellange kæder, som geleres 2 DK 173547 B1 med et organisk modificeret magnesiumlagsiiicat. Sådanne salvegeler kan indeholde uldvoksalkoholer som emulgatorer og maksimalt optage 5,5 til 5,7% salicylsyre.According to Veroffentlichung by U. Adams et al. (Pharm. Ind., Vol. 44, No. 6,1982, pages 625-629), salicylic acid is absorbed into ointments formed as gels and as an ointment containing medium-chain triglycerides which are gelled with an organically modified magnesium layer. Such ointment gels may contain wool wax alcohols as emulsifiers and take up a maximum of 5.5 to 5.7% salicylic acid.
5 Det har ved brug af de kendte salicylsyreholdige midler vist sig, at disse kendte midler ved deres anvendelse af en række grunde, hvortil f. eks. hører en betydelig lugtbelastning på grund af harskning af de fede olier under behandlingen, som ikke eller kun i ringe grad kan accepteres af patienterne, og i praksis faktisk kun giver det ønskede resultat ved behandling på sygehus.5 It has been found by the use of the known salicylic acid-containing agents that these known agents, by their use for a number of reasons, for example, include a considerable odor load due to rancidity of the fatty oils during treatment, which do not or only in to a low degree can be accepted by the patients, and in practice only gives the desired result in hospital treatment.
10 Det er dog for de med midlerne behandlede patienter af særlig betydning, også af psykologiske grunde.10 However, it is of special importance for patients treated with the funds, also for psychological reasons.
Det tilsigtes med den foreliggende opfindelse at tilvejebringe et salicylsyre-holdigt middel af den tidligere nævnte art, som ved god tålelighed uden uhel-15 dige virkninger for patienten muliggør en behandling, som ikke foretages på sygehus.It is an object of the present invention to provide a salicylic acid-containing agent of the aforementioned kind which, with good tolerability, without adverse effects to the patient, enables treatment not to be performed in hospital.
Dette opnås ved hjælp af den foreliggende forbindelse med et middel, der indeholder4 til 10 vægt-% salicylsyre, 1-7 vægt-% afen alifatisk 1,2-diol og 20 83 til 95 vægt-% af en fed olie.This is achieved by the present compound with an agent containing 4 to 10% by weight of salicylic acid, 1-7% by weight of an aliphatic 1,2-diol, and 83 to 95% by weight of a fatty oil.
Mætningskoncentrationen af salicylsyre i fede olier eller blandinger deraf ligger i området 3 til højst 5%, hvilket er for lavt i mange anvendelsestilfælde.The saturation concentration of salicylic acid in fatty oils or mixtures thereof is in the range of 3 to at most 5%, which is too low in many applications.
Det har nu overraskende vist sig, at man kan opnå højere mætningskoncen-25 trationer, når der fremstilles en blanding af salicylsyre og fede olier, samt en 1,2-diol. Derved kan anvendes forskellige alifatisk 1,2-dioler, idet 1,2-propandiol og de forskellige butylenglycoler med nabostillede hydroxylgrup-per har vist sig særligt gunstige.Surprisingly, it has now been found that higher saturation concentrations can be obtained when preparing a mixture of salicylic acid and fatty oils, as well as a 1,2-diol. Thereby various aliphatic 1,2-diols can be used, since 1,2-propanediol and the various butylene glycols with neighboring hydroxyl groups have proved particularly favorable.
30 I midlet ifølge opfindelsen kan anvendes sædvanlige fede olier, foretrukkent fede olier af vegetabilsk oprindelse, som er triglycerider. Af triglycerider har de triglycerider eller blandinger deraf, hvori der indgår fede syrer, der har middellang kæde, vist sig særligt hensigtsmæssige, idet trigiycerideme af caprylsyre, caprinsyre eller blandinger deraf er særligt foretrukne. De fore 3 DK 173547 B1 trukne forbindelser har vist sig særligt gunstige; der kan i stedet for triglyceri-der eller blandinger deraf dog også anvendes andre estere, f. eks. sådanne af mono- eller divalente alkoholer og især fede syrer med middellang kæde.In the composition of the invention, conventional fatty oils, preferably vegetable oils of triglycerides, may be used. Of triglycerides, the triglycerides or mixtures thereof which include fatty acids having a medium chain have been found to be particularly suitable, the triglycerides of caprylic acid, capric acid or mixtures thereof being particularly preferred. The compounds drawn have proved particularly favorable; however, instead of triglycerides or mixtures thereof, other esters, such as those of mono or divalent alcohols and especially medium chain fatty acids, may also be used.
5 Midlet ifølge opfindelsen er godt tåleligt også ved langtidsanvendelse; hidtil er der ikke iagttaget nogen allergiske reaktioner ved langtidsanvendelse.The agent of the invention is well tolerable even in long-term use; So far no allergic reactions have been observed with long-term use.
Derved opnås en høj virkning; især opnås allerede efter forholdsvis kort anvendelsestid, alt efter sygdommens alvor, en fuldstændig skælfjernelse, dvs. symptomfrihed, som bibeholdes ved tilsvarende efterbehandling.Thereby a high effect is obtained; especially after a relatively short period of use, depending on the severity of the disease, a complete scaly removal, ie. freedom of symptom, which is maintained by corresponding post-treatment.
1010
Et særligt virkningsfuldt, foretrukkent middel ifølge opfindelsen indeholder 4 til 10 g salicylsyre, 1 -7 g 1,2-propandiol og 83 til 95 g triglycerid af caprylsyre, caprinsyre eller en blanding deraf.A particularly effective preferred agent according to the invention contains 4 to 10 g of salicylic acid, 1-7 g of 1,2-propanediol and 83 to 95 g of triglyceride of caprylic acid, capric acid or a mixture thereof.
15 En vigtig årsag til den høje virkning af midlet ifølge opfindelsen ligger muligvis deri, at den valgte opløsningsmiddelblanding indvirker terapeutisk særlig gunstigt på den syge hud og derved danner en meget virksom bærer, som bringer salicylsyren til virkestedet, 20 Endvidere er behandlingen med midlerne ifølge opfindelsen ikke forbundet med uønskede og uacceptable belastninger for patienten, fordi midlet ifølge opfindelsen hurtigt resorberes fuldstændigt i huden. Derfor kommer der ikke for patienten uacceptable lugtbelastninger på grund af harskning af fedtstofferne eller de fede olier samt uønsket tilsmudsning af klæder eller sengetøj.An important reason for the high efficacy of the agent of the invention may lie in the fact that the selected solvent mixture acts therapeutically particularly favorably on the diseased skin, thereby forming a highly effective carrier which brings the salicylic acid to the site of action. 20 Furthermore, the treatment with the agents of the invention is not associated with undesirable and unacceptable loads for the patient because the agent of the invention is rapidly completely resorbed in the skin. Therefore, unacceptable odor loads are not available to the patient due to rancidity of the fats or fatty oils and unwanted soiling of clothes or bedding.
25 En yderligere helt væsentlig fordel ved midlet ifølge opfindelsen består deri, at i de fleste tilfælde er et sygehusophold ikke længere nødvendigt. Derfor opnår man samlet en meget høj accept fra patienternes side.A further essential advantage of the agent according to the invention is that in most cases a hospital stay is no longer necessary. Therefore, a very high acceptance is obtained from the patients.
Foretrukne udførelseseksempler for opfindelsen forklares nærmere i det føl-30 gende i sammenhæng med fremgangsmåden til fremstilling deraf. De anvendte materialer opfyldte renhedskravene i D.A.B.Preferred exemplary embodiments of the invention will be explained in greater detail below in the context of the method of preparation thereof. The materials used met the purity requirements of D.A.B.
Salicylsyre rives i mængder på 4, 5, 7,5 og 10 g og i en mængde på 1, 2, 4,5 eller 7 g 1,2-propandiol på sædvanlig måde. Dernæst bliver der til de 5, 7,12 4 DK 173547 B1 eller 17 g 1,2-propanol-riveprodukt sat 95, 93, 88 eller 83 g af en fed olie af vegetabilsk oprindelse eller et triglycerid, og blandingen omrøres så længe, at der dannes en klar, olieagtig opløsning. Disse midler indeholder således i vægt-% og baseret på den samlede vægtmængde = 100, 5 _Salicylic acid is teared in amounts of 4, 5, 7.5 and 10 g and in an amount of 1, 2, 4.5 or 7 g of 1,2-propanediol in the usual manner. Next, to the 5, 7,12 4 B1 or 17 g of 1,2-propanol tear product is added 95, 93, 88 or 83 g of a vegetable oil or triglyceride fatty oil and the mixture is stirred for as long as possible. to form a clear, oily solution. Thus, these agents contain in% by weight and based on the total weight = 100, 5
Salicylsyre__4 5 7,5 10 1,2-propandiol__1 2 4,5 7_Salicylic Acid 5 7.5 7.5 1,2-Propanediol 4,5 2 4.5 7_
Triglycerid_95 93 88 83Triglyceride_95 93 88 83
Foretrukkent går man således frem, at man - idet man går ud fra mætningskoncentrationen for salicylsyre i triglycerid - anvender netop så meget 1,2-propandiol, at der opnås en mættet eller næsten mættet opløsning af den 10 ønskede salicylsyremængde i 1,2-propandiol/triglycerid-blahdiiigen. Det har i hvert tilfælde vist sig gunstigt for behandlingen, når man anvender mættede eller næsten mættede opløsninger af salicylsyren.Preferably, it is stated that - assuming the saturation concentration of salicylic acid in triglyceride - just as much 1,2-propanediol is used as to obtain a saturated or almost saturated solution of the desired salicylic acid amount in 1,2-propanediol. / triglyceride blahdiiigen. In each case, it has proved beneficial for the treatment when using saturated or nearly saturated solutions of the salicylic acid.
Disse midler anvendes på den i det følgende beskrevne måde til behandling 15 af hudsygdomme med skæl, såsom psoriasis, tinea amiantacea, seborrhoea sicca, hos mennesker og af sommersår og særlige sygdomme med skæl f. eks. hos ponyer. Alt i alt har det ved disse og andre lignende undersøgelser vist sig, at virksomheden og behandlingsvarigheden under hensyn til tålelighed indtil symptomfrihed af de midler, der indeholdt 4 til 7,5 vægt-% salicylsy-20 re, 1 til 4,5 vægt-% alifatisk 1,2-diol og 88 til 93 vægt-% fed olie, har den relativt bedste virkning.These agents are used in the manner described below for the treatment of skin diseases with dandruff, such as psoriasis, tinea amiantacea, seborrhoea sicca, in humans and of summer ulcers and special diseases with dandruff, for example, in ponies. All in all, in these and other similar studies, it has been found that, with respect to tolerability until symptom-free of the agents containing 4 to 7.5 wt.% Salicylic acid, 1 to 4.5 wt. % aliphatic 1,2-diol and 88 to 93% by weight of fatty oil have the relatively best effect.
Ved yderligere undersøgelser viste det sig, at i stedet for 1,2-propandiol kan man også anvende de forskellige butylenglycoler med nabostillede hydroxyl-25 grupper og eventuelt også andre alifatiske 1,2-dioler. Ligeledes kan man i stedet for fede olier af vegetabilsk oprindelse eller triglycerider eller blandinger deraf anvende triglycerider af fede syrer med middellange kæder, dvs.Further studies showed that instead of 1,2-propanediol, the various butylene glycols with adjacent hydroxyl groups and possibly other aliphatic 1,2-diols can also be used. Likewise, instead of fatty oils of vegetable origin or triglycerides or mixtures thereof, triglycerides of fatty acids of medium chains may be used, i.e.
Ca-til Ci2-syrer eller blandinger deraf.Ca - to C12 acids or mixtures thereof.
30 Den terapeutiske anvendelse forklares nærmere i det følgende ved hjælp af et udførelseseksempel, hvor man anvender 5 vægt-% salicylsyre, 2 vægt-% DK 173547 B1 r- 5 1,2-propandioi og 93 vægt-% triglycerider med middellang kæde (totalvægt for midlet = 100), på en patientgruppe på 150 mennesker, som hovedsageligt lider af psoriasis og for en lille dels vedkommende af andre skællende hud-og hovedbundssygdomme, f. eks. seborrhoeiske eksemer. Behandlingen 5 består deri, at (a) ved sygdomme i hovedbunden påføres midlet 2 til 3 gange om ugen på de pågældende steder i hovedbunden; behandlingen kan foregå natten over under anvendelse af en badehætte med sluttende gum- 1 o mikant og en i handelen tilgængelig operationshætte til fiksering nat ten over, og (b) ved sygdomme på legemshuden påføre midlet 1 til 2 gange dagligt på de pågældende steder, idet midlet fjernes fra huden efter 10 til 15 mi- 15 nutters indvirkningstid,The therapeutic use is explained in more detail below by means of an embodiment using 5 wt% salicylic acid, 2 wt% DK 173547 B1 r-1,2-propanediol and 93 wt% medium chain triglycerides (total weight) for the agent = 100), in a patient group of 150 people suffering mainly from psoriasis and, to a small extent, from other scaly skin and scalp diseases, such as seborrhoeic eczema. The treatment 5 consists in: (a) for diseases of the scalp applied to the agent 2 to 3 times a week at the relevant sites on the scalp; the treatment may take place overnight using a sealing rubber cap and a commercially available night-time operating cap, and (b) in case of diseases of the skin, apply the agent 1 to 2 times daily at the locations in question. the agent is removed from the skin after 10 to 15 minutes of action,
For 8 personers vedkommende blev behandlingen afbrudt for tidligt af grunde, som ikke havde noget at gøre med den egentlige behandling. For 50 personers vedkommende blev alt efter sværheden af den oprindelige sygdom 2 o opnået total skælfrihed og dermed det ønskede udseendes resultat efter en behandlingstid på • 1 måned ved let oprindelig sygdom, 25 · op til 3 måneder ved middelsvær oprindelig sygdom og • op til 4 måneder ved svær oprindelig sygdom, idet begyndende skælfrihed allerede kunne ses i de første uger.For 8 people, the treatment was interrupted prematurely for reasons that had nothing to do with the actual treatment. For 50 persons, depending on the severity of the original disease, 2 o total freedom of flushing was achieved and thus the desired appearance result after a treatment period of • 1 month for mild-onset illness, 25 · up to 3 months for moderate-onset illness and • up to 4 months of severe initial illness, with initial onset of dandruff already seen in the first weeks.
30 For størstedelen af de resterende 92% patienters vedkommende var skæl-fjernelsen efter op til 1 års behandling meget langt fremskreden, og man kunne dermed også her forvente en total skælfrihed og dermed det ønskede resultat. Allergiske reaktioner blev ikke iagttaget, og behandlingen blev accepteret fremragende af patienterne. Hertil bidrager, at midlet er neutralt i 6 DK 173547 B1 henseende til lugt og meget hurtigt trænger ind i huden, hvorved der ikke sker nogen tilsmudsning af klæder eller sengetøj, samt den kendsgerning, at kun ved særlige omstændigheder og meget svære sygdomstilfælde er et hospitals- eller klinikophold nødvendigt.For most of the remaining 92% of patients, the dandruff removal was very far advanced after up to 1 year of treatment, and one could thus expect total dandruff freedom and thus the desired result. Allergic reactions were not observed and treatment was well accepted by the patients. To this end, the agent is neutral in smell and penetrates the skin very quickly in 6 DK 173547 B1, thereby preventing any soiling of clothes or bedding, and the fact that only in special circumstances and very serious illness is a hospital - or clinic stay necessary.
55
Som meget fordelagtige sidevirkninger kunne der fastslås en meget tydelig forøget hårvækst, også inden for det veterinærmedicinske område.As very beneficial side effects, a very marked increase in hair growth could be observed, also in the veterinary field.
En gang opnået symptomfrihed kan også opretholdes efterfølgende. Dertil 10 anbefales en følgeterapi under anvendelse af i handelen tilgængelige skæl- dannelsesreducerende midler, såsom dithranol, på skift med det i det foregående beskrevne middel.Once achieved, symptom relief can also be maintained afterwards. In addition, a follow-up therapy using commercially available scalding reducing agents, such as dithranol, is recommended in alternation with the above-described agent.
Claims (9)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3724691A DE3724691C2 (en) | 1987-07-25 | 1987-07-25 | Pharmaceutical agent for the local therapy of flaking skin diseases |
| DE3724691 | 1987-07-25 | ||
| EP8800649 | 1988-07-19 | ||
| PCT/EP1988/000649 WO1989000853A1 (en) | 1987-07-25 | 1988-07-19 | Agent containing salicylic acid for treating lepidosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK137589D0 DK137589D0 (en) | 1989-03-21 |
| DK137589A DK137589A (en) | 1989-05-19 |
| DK173547B1 true DK173547B1 (en) | 2001-02-19 |
Family
ID=6332361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198901375A DK173547B1 (en) | 1987-07-25 | 1989-03-21 | Salicylic acid-containing agent for the local treatment of skin diseases with dandruff in the human and veterinary medicine |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0325628B1 (en) |
| JP (1) | JPH02500106A (en) |
| AT (1) | ATE69550T1 (en) |
| AU (1) | AU2072088A (en) |
| DE (2) | DE3724691C2 (en) |
| DK (1) | DK173547B1 (en) |
| FI (1) | FI94314C (en) |
| NO (1) | NO175885C (en) |
| WO (1) | WO1989000853A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR1001303B (en) * | 1989-01-23 | 1993-07-30 | Wolff Chem Pharm Gmbh | Method for preparation of a means that contains salicyloxyd against scaling sick |
| ATE91079T1 (en) * | 1989-01-25 | 1993-07-15 | Wolff Chem Pharm Gmbh | SALICYLIC ACID AGENT AGAINST SCALPING SKIN DISEASES. |
| GB9223034D0 (en) * | 1992-11-03 | 1992-12-16 | Surtech Int Ltd | Method and composition for prevention and/or treatment of dandruff and seborrhoeic dermatitis |
| SE9403541L (en) * | 1994-10-14 | 1996-04-15 | Sven Moberg | Antimicrobial composition |
| US5736580A (en) * | 1994-11-14 | 1998-04-07 | Alza Croporation | Composition, device, and method for electrotransport agent delivery |
| US5990179A (en) * | 1995-04-28 | 1999-11-23 | Alza Corporation | Composition and method of enhancing electrotransport agent delivery |
| US5985316A (en) * | 1995-04-28 | 1999-11-16 | Alza Corporation | Composition and method of enhancing electrotransport agent delivery |
| US6623724B2 (en) | 1996-09-18 | 2003-09-23 | Applied Genetics Incorporated Dermatics | Dermatological compositions and methods |
| US5990177A (en) * | 1996-09-18 | 1999-11-23 | Codon Pharmaceuticals, Inc. | Treatment of diseases mediated by the nitric oxide/cGMP/protein kinase G pathway |
| DE10205193A1 (en) * | 2002-02-08 | 2003-08-21 | Beiersdorf Ag | Cleaning preparations containing diol |
| DE10341179A1 (en) † | 2003-09-06 | 2005-03-31 | Beiersdorf Ag | Cosmetic or dermatological preparations containing synergistic combination of alpha- or beta-hydroxyacid and alkanediol, useful for combating acne and/or Propionibacterium acnes infection |
| CN104105472A (en) | 2011-12-20 | 2014-10-15 | 维奥姆生物科学有限公司 | Topical oil composition for the treatment of fungal infections |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE762726C (en) * | 1942-05-02 | 1952-09-15 | Hydrierwerke A G Deutsche | Solvent or solubilizer for salicylic acid |
| JPS57171912A (en) * | 1981-04-14 | 1982-10-22 | Sumitomo Chem Co Ltd | Cream |
| FR2585575B1 (en) * | 1985-08-01 | 1989-03-03 | Pf Medicament | PHARMACEUTICAL COMPOSITIONS WITH KERATOLYTIC ACTIVITY IN GEL FORM COMPRISING HYDROALCOHOLIC SALICYLIC ACID |
-
1987
- 1987-07-25 DE DE3724691A patent/DE3724691C2/en not_active Expired - Fee Related
-
1988
- 1988-07-19 AT AT88905833T patent/ATE69550T1/en not_active IP Right Cessation
- 1988-07-19 JP JP63505873A patent/JPH02500106A/en active Pending
- 1988-07-19 AU AU20720/88A patent/AU2072088A/en not_active Abandoned
- 1988-07-19 EP EP88905833A patent/EP0325628B1/en not_active Expired - Lifetime
- 1988-07-19 DE DE8888905833T patent/DE3866344D1/en not_active Expired - Lifetime
- 1988-07-19 WO PCT/EP1988/000649 patent/WO1989000853A1/en active IP Right Grant
-
1989
- 1989-03-20 NO NO891220A patent/NO175885C/en not_active IP Right Cessation
- 1989-03-21 DK DK198901375A patent/DK173547B1/en not_active IP Right Cessation
- 1989-03-22 FI FI891357A patent/FI94314C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI891357A0 (en) | 1989-03-22 |
| DE3724691A1 (en) | 1989-02-02 |
| JPH02500106A (en) | 1990-01-18 |
| EP0325628A1 (en) | 1989-08-02 |
| FI891357A (en) | 1989-03-22 |
| DE3724691C2 (en) | 1999-03-18 |
| NO891220D0 (en) | 1989-03-20 |
| DK137589A (en) | 1989-05-19 |
| DE3866344D1 (en) | 1992-01-02 |
| FI94314B (en) | 1995-05-15 |
| NO175885B (en) | 1994-09-19 |
| FI94314C (en) | 1995-08-25 |
| NO891220L (en) | 1989-03-20 |
| AU2072088A (en) | 1989-03-01 |
| EP0325628B1 (en) | 1991-11-21 |
| ATE69550T1 (en) | 1991-12-15 |
| NO175885C (en) | 1994-12-28 |
| WO1989000853A1 (en) | 1989-02-09 |
| DK137589D0 (en) | 1989-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |
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