AU6669400A - Use of 1,1-dioxoperhydro-1,2,4-thiadiazines - Google Patents
Use of 1,1-dioxoperhydro-1,2,4-thiadiazines Download PDFInfo
- Publication number
- AU6669400A AU6669400A AU66694/00A AU6669400A AU6669400A AU 6669400 A AU6669400 A AU 6669400A AU 66694/00 A AU66694/00 A AU 66694/00A AU 6669400 A AU6669400 A AU 6669400A AU 6669400 A AU6669400 A AU 6669400A
- Authority
- AU
- Australia
- Prior art keywords
- dioxoperhydro
- thiadiazine
- radicals
- acne
- 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.)
- Abandoned
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Description
S&FRef: 528071
AUSTRALIA
PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT
ORIGINAL
Name and Address of Applicant: Actual Inventor(s): Address for Service: Invention Title: Goldschmidt AG Goldschmidtstrasse 100 D-45127 Essen Germany Thomas Dietz, Burghard Gruning, Peter Lersch and Christian Weitemeyer Spruson Ferguson St Martins Tower 31 Market Street Sydney NSW 2000 Use of 1,1-dioxoperhydro-1,2;4-thiadiazines The following statement is a full description of this invention, including the best method of performing it known to me/us:- 5845c Use of 1,1-dioxoperhydro-1,2,4-thiadiazines The invention relates to the use of 1,1-dioxoperhydro-1,2,4-thiadiazines for the preparation of cosmetic or pharmaceutical preparations which are effective against bad skin and forms of acne.
Bad skin is essentially caused by increased activity of the sebaceous glands and increased secretion of sebum associated therewith. Acne is a skin disease characterised by noninflammed and inflamed papules which can lead to the formation of pustules, abscesses and scars. Causes are the keratinisation and blocking of hair follicles (formation of comedones), increased sebum production and the production of tissue-damaging enzymes by bacteria (Propionibacterium acnes). Antibiotics, keratolytics and peroxides are used as therapy.
Thus, for example, EP 0 536 360 A describes the topical treatment of acne using the aminopenicillin and cephalosporin classes of antibiotics. However, antibiotics have the disadvantage that the controlled microorganisms, for example bacteria, can become resistant thereto. EP 0 639 068 A describes the treatment of acne using the keratolytics salicylic acid and pantothenic acid. Keratolytics soften or loosen keratinised layers of skin, but have no effect on microorganisms which cause inflammation. US 5 767 098 A describes the treatment of 15 acne by the topical application of a combination of an antibiotic and a peroxide. However, substances such as benzoyl peroxide are free-radical formers, which cause oxidative stress of the skin and can therefore lead to longterm damage. Although substances such as benzoyl peroxide or retinoic acid are effective in reducing pimples, Sthey also cause irritations, sensitisations and allergies, which manifest themselves as stinging, itching, buming, flaking or reddening of the skin.
20 Taurolidine is a 1,1-dioxoperhydro-1,2,4-thiadiazine derivative and a substance known for over years (see CH 482 713 A) and characterised by the general formula (I)
R'
02
R
S(I)
CH
2
(II)
It has hitherto been used exclusively in human medicine. Thus, for example, EP 0 253 662 A describes the use of taurolidine in the form of an aqueous solution for parenteral administration during surgical interventions against infections by bacteria or bacterial toxins. WO 92/00743 describes a method for the treatment or prophylaxis of tumours by administering an effective dose of taurolidine and/or taurultam. DE 35 33 612 A describes the use of taurolidine as an anticoagulant. WO 94/03174 describes a dental composition comprising taurolidine for the treatment of, for example, parodontitis.
The mode of action of taurolidine is presumably based on the transfer of methylol groups to the hydroxyl or amino groups positioned on toxins or on the murein of bacteria cell walls. In solution, taurolidine where R 1 H and R 2 radical having the formula (II) is in equilibrium with taurultam LibC/528071speci 2 where R 1 and R 2 H and N-methyloltaurultam where R 1 H and R 2
-CH
2 -OH. With the transference of the methylol groups to toxins or bacteria, methyloltaurultam is converted into taurultam which is in turn in equilibrium with methyloltaurinamide (III)
R
3
HN-CH
2 -CH2-S02-R 4
(III)
where R 3
-CH
2 0H and R 4
-NH
2 The transference of methylol groups results in the conversion of methyloltaurinamide to taurinamide (III') where R 3 H and R 4
-NH
2 Taurinamide (III') is transformed physiologically into taurine where R 3 H and R 4 OH, a naturally occurring aminosulfonic acid which is tolerated exceedingly well by the body.
It is known from the literature that 1,1-dioxo-perhydro-1,2,4-thiadiazines, in particular taurolidine and the abovementioned metabolites, are effective against various bacteria and fungi. For example, Arzneim.-Forschung, 42 1992, 1157 1159 describes the in-vitro activity of taurolidine against oral-pathogenic microorganisms. The investigation also considers the anaerobic Propionibacterium acnes which, apart from being found in inflamed areas in the gum, is also found in inflammation foci in acne patients. However, the appearance of Propionibacterium acnes in acne patients and the 15 inflammation caused as a result are a consequence of acne, not a cause. On the contrary, Propionibacterium acnes can also be found in subjects not suffering from acne. The literature reveals nothing about the use of taurolidine for topical application to the skin for the purpose of treating bad skin and acne.
The object of the present invention is therefore to provide an active ingredient which 20 counteracts the causes of bad skin and acne, namely hyperkeratosis, excessive sebum production and bacterial infection, but which does not have negative effects on the skin, such as, for example, skin irritations, skin flaking or resistance by bacteria.
Surprisingly, we have now found that 1,1-dioxoperhydro-1,2,4-thiadiazines of the general formula 1 N 02
(I)
in particular taurolidine where R H and R 2 radical having the formula (II)
,N
02
CH
2 Ill) or taurultam where R 1 and R 2 H are extremely effective against bad skin and forms of acne, but, being chemotherapeutics, do not have the disadvantages of antibiotics, for example the development of resistances, and, in addition, do not trigger irritations of any kind upon topical application to the skin. The high effectiveness against bad skin and acne which has been found cannot be explained by LibC/528071speci the in-vitro activity of taurolidine against Propionibacterium acnes alone, and was therefore not tf be expected.
In a first embodiment, the invention provides for the use of 1,1-dioxoperhydro-1,2,4-thiadiazines of the general formula 2 02
(I)
in which R 1 and R 2 which are identical or different, are hydrogen atoms, alkyl radicals having 1 to 18 carbon atoms, cycloalkyl radicals, aralkyl radicals or aromatic or heterocyclic radicals each having 3 to carbon atoms, where the radicals R 1 and R 2 are optionally substituted, for the preparation of cosmetic or pharmaceutical preparations for the treatment of bad skin and acne. Corresponding compounds, in particular compounds having substituted radicals, are known from CH 48 27 13 A, to the entire contents of which reference is made.
The invention further provides for the use of 1,1-dioxo-perhydro-1,2,4-thiadiazines in cosmetic or pharmaceutical preparations for the treatment of bad skin and acne, wherein, in the 1,1dioxoperhydro-1,2,4-thiadiazine R 1 and R 2 are hydrogen atoms (taurultam or R 1 is a hydrogen 15 atom and R 2 corresponds to a radical of the formula (II) (taurolidine The concentration of 1,1-dioxoperhydro-1,2,4-thiadiazine including metabolites in the cosmetic or pharmaceutical preparations is preferably 0.005 to 10.00% by weight, preferably 0.01 5.0% by weight, in each case based on the total weight of the preparations.
According to an advantageous embodiment of the present invention, 1,1-dioxoperhydro-1,2,4- 20 thiadiazines are used with other agents effective against bad skin and acne in cosmetic or pharmaceutical preparations. Particularly suitable is a combination of 1,1-dioxoperhydro-1,2,4thiadiazine with a keratolytic, in particular salicylic acid, lactic acid, glycolic acid, citric acid or malic acid.
The preparations can be used in the form of liquid compositions which can be applied using brushes or strips, or by means of roll-on devices, as sticks and in the form of W/O or O/W emulsions which can be applied from customary bottles and containers, for example creams or lotions.
Furthermore, the preparations can advantageously be in the form of face washes, tinctures or cleansing formulations.
Apart from water, customary carriers for the preparation of the preparations which may be used are ethanol and isopropanol, glycerol, propylene glycol, polyglycerol and polyethylene glycol, fats or fat-like substances which are beneficial to the skin, such as cetyl alcohol, cetearyl octanoate, decyl oleate and octyldodecanol, in the quantitative ratios customary for such preparations, and also thickeners, for example hydroxyethylcellulose or hydroxypropylcellulose, salts of polyacrylic acid, polyvinylpyrrolidone, as well as, also in small amounts, cyclic and chain-like silicone oils and organically modified silicones.
LibC/528071speci Emulsifiers which have proven suitable for the preparation of the preparations, which are advantageously to be applied as liquid preparations to the desired areas of skin, and which can be used in the preparations in a small amount, for example 1 to 5% by weight, based on the total composition, are nonionogenic types, such as polyoxyethylene fatty alcohol ethers, for example cetostearyl alcohol polyethylene glycol ethers having 10, 20 or added ethylene oxide units per molecule, cetostearyl alcohol and sorbitan esters and sorbitan ester ethylene oxide compounds (for example sorbitan monostearate and polyoxyethylene sorbitan monostearate), glycerol and polyglycerol esters, for example polyglycerol isostearate, sugar esters, for example methylglucose dioleate or cetearyl glucoside, polysiloxane-polyoxyethylene/oxypropylene and polysiloxane-polyoxyethylene/oxypropylenepolycetyl copolymers.
In addition to said constituents, the preparations according to the invention, the pH of which is preferably adjusted to 3.5 to 9.0, in particular 4.0 to 6.5 for example using customary buffer mixtures, can be admixed with perfume, dyes, antioxidants (for example ac-tocopherol and its derivatives or butylhydroxytoluene (BHT), 2,6-di-tert-butyl-4-methylphenol) in amounts of from 0.01 to 0.03%, based on the total composition), dispersion auxiliaries, buffer mixtures or other customary cosmetic raw o 15 materials.
The amounts of carriers to be used in each case can be readily determined by the person skilled in the art by simple exploratory experiments, depending on the type of product in question.
The preparations according to the invention, apart from specific preparations which are in each case noted separately in the examples, are prepared in the customary manner, in most cases by simply mixing with stirring, if necessary with slight warming. For emulsions, the fatty phase and the S. aqueous phase are, for example, prepared separately, if necessary with warming, and are then emulsified. Otherwise, the customary guidelines for preparing pharmaceutical formulations are to be observed, with which the person skilled in the art is familiar.
Advantageous working examples of the present invention are given below.
Examples: Example 1: SGel by weight Taurolidine Hydroxyethylcellulose Water 96.0 Taurolidine was dissolved in water, and the hydroxyethylcellulose was incorporated. The resulting gel was packed in aluminium tubes.
Example 2: Wax stick by weight Hydrogenated castor oil Beeswax Hard paraffin 30.0 C12 to C15 alkyl benzoate 17.0 Taurolidine 0.9 Octyldodecanol 141.1 LibC/528071speci The constituents were melted at about 75*C, mixed well and poured into suitable moulds.
Example 3: Face wash %by wei ht Ethanol Taurolidine Water 90.0 Example 4: OMW Face cream by weight A Polyglyceryl-3 methylglucose distearate Glyceryl stearate 2.8 Stearyl alcohol 1.2 Isocetyl palmitate ___Ethylhexyl palmitate ___Isopropyl palmitate B [Glycerol [Water 70.0 ___Taurolidine Phase A and phase B were heated separately to 70'C. Phase A was added with stirring to phase B and then homogenised. The mixture was cooled with gentle stirring.
Example W/O cream by weight A _Cetyldimethicone copolyol ___Polyglyceryl-4 isostearate ___Mineral oil 12.0 ___Ethylhexyl stearate ___Hydrogenated castor oil 10.8 Microcrystal line wax 11.2 B Sodium chloride ___Taurolidine ___Water 75.5 Phase A was heated to about 80*C, phase B was slowly stirred in and then briefly homogenised. The mixture was cooled to below 30 0 C with gentle stirring and homogenised again.
Example 6: WI0IW Emulsion f by weight 01_ Cetyldimethicone copolyol ___Capryl/capric triglycerides 16.0 ___ISalicylic acid 1W1 Glycerol 11.0 Taurolidine1.
___Water278 0.15 27.85 LibCI528O7 1 spedi W2 Water 39.0 Propylene glycol Caprylyl/capryl glucosides, 10% Sodium hydroxide, 10% q.s.
D Xanthan gum 0.1 Acrylate/C10-30 alkyl acrylate crosspolymer 0.2 Mineral oil 0.7 Phase W1 was added to phase O with stirring and then homogenised. The components of phase W2 were mixed. A dispersion was prepared from the components of phase D, added to W2 and briefly homogenised. The W1/0 emulsion was added to W2 in portions with stirring.
The surprisingly high effectiveness of 1,1-dioxoperhydro-1,2,4-thiadiazines, in particular taurolidine, in the treatment of bad skin and acne is demonstrated by way of example by the following case descriptions.
Case 1: Case 1 is an 18-year old girl with Acne simplex. For two years she has been treated with customary substances (benzoyl peroxide, aluminium oxide as peeling therapy), but without success.
10 She applied the gel from Example 1 twice daily over a period of 3 months. After just two weeks a positive development was found, evident from a reduction in inflamed areas and infected pustules.
After 3 months the condition had fundamentally improved. No further treatment with the taurolidine gel was necessary. No skin irritations were observed throughout the entire treatment period.
Case 2: S 15 Case 2 is a 34-year old man with severe acne and comedones on the back. He was treated with the gel from Example 1 for 8 days. After just one day it was possible to observe a decrease in infected areas. After three days the complaint had already significantly improved. After one week no further treatment was required.
LibC/528071speci
Claims (21)
1. The use of 1,1-dioxoperhydro-1,2,4-thiadiazines of the general formula 02 R (I) in which R 1 and R 2 which are identical or different, are hydrogen atoms, alkyl radicals having 1 to 18 carbon atoms, cycloalkyl radicals, aralkyl radicals or aromatic or heterocyclic radicals each having 3 to carbon atoms, where the radicals R 1 and R 2 are optionally substituted, for the preparation of cosmetic or pharmaceutical preparations for the treatment of bad skin and acne.
2. The use as claimed in claim 1, wherein, in the 1,1-dioxoperhydro-1,2,4-thiadiazine of the general formula R 1 and R 2 are in each case a hydrogen atom (taurultam).
3. The use as claimed in claim 1, wherein R 1 in the general formula is a hydrogen atom, and R 2 is a radical of the formula (II) CH2 H 2 (II) (taurolidine).
4. The use as claimed in any one of claims 1 to 3, wherein the concentration of 1,1- dioxoperhydro-1,2,4-thiadiazine including metabolites is 0.005 to 10.00% by weight, in each case based on the total weight of the preparations.
5. The use as claimed in any one of claims 1 to 4, wherein the concentration of 1,1- dioxoperhydro-1,2,4-thiadiazine including metabolites is 0.01 5.0% by weight, in each case based on the total weight of the preparations.
6. The use as claimed in any one of claims 1 to 5 in combination with further customary 20 agents known per se which are effective against bad skin and acne.
7. The use as claimed in claim 6, wherein the further agent is a keratolytic.
8. The use as claimed in claim 7, wherein the keratolytic is chosen from salicylic acid, lactic acid, glycolic acid, citric acid or malic acid.
9. A method for the treatment or prevention of bad skin and acne in a mammal requiring said treatment or prevention, which method includes or consists of administering to said mammal an effective amount of at least one 1,1-dioxoperhydro-1,2,4-thiadiazine of the general formula R 1 N, R, N 02 (I) LibC/528071speci in which R 1 and R 2 which are identical or different, are hydrogen atoms, alkyl radicals having 1 to 18 carbon atoms, cycloalkyl radicals, aralkyl radicals or aromatic or heterocyclic radicals each having 3 to carbon atoms, where the radicals R 1 and R 2 are optionally substituted. The method as claimed in claim 9, wherein, in the 1,1-dioxoperhydro-1,2,4-thiadiazine of the general formula R 1 and R 2 are in each case a hydrogen atom (taurultam).
11. The method as claimed in claim 9, wherein R 1 in the general formula is a hydrogen atom, and R 2 is a radical of the formula (II) N 02 CH 2 (II) (taurolidine).
12. The method as claimed in any one of claims 9 to 11, wherein the 1,1-dioxoperhydro- 1,2,4-thiadiazine is administered in a preparation at concentration of 0.005 to 10.00% by weight 1,1- dioxoperhydro-1,2,4-thiadiazine including metabolites, in each case based on the total weight of the preparation.
13. The method as claimed in any one of claims 9 to 12, wherein the 1,1-dioxoperhydro- 1,2,4-thiadiazine is administered in a preparation at concentration of 0.01 5.0% by weight 1,1- 15 dioxoperhydro-1,2,4-thiadiazine including metabolites, in each case based on the total weight of the preparations.
14. The method as claimed in any one of claims 9 to 13, wherein said 1,1-dioxoperhydro- **1,2,4-thiadiazine is administered in combination with further customary agents known per se which are effective against bad skin and acne.
15. The method as claimed in claim 14, wherein the further agent is a keratolytic.
16. The method as claimed in claim 15, wherein the keratolytic is chosen from salicylic acid, lactic acid, glycolic acid, citric acid or malic acid.
17. A 1,1-dioxoperhydro-1,2,4-thiadiazine of the general formula 1 N 02 (i) in which R 1 and R 2 which are identical or different, are hydrogen atoms, alkyl radicals having 1 to 18 carbon atoms, cycloalkyl radicals, aralkyl radicals or aromatic or heterocyclic radicals each having 3 to carbon atoms, where the radicals R 1 and R 2 are optionally substituted when used in the treatment or prevention of bad skin and acne.
18. The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in claim 17, wherein R 1 and R 2 are in each case a hydrogen atom (taurultam).
19. The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in claim 17, wherein R 1 is a hydrogen atom, and R 2 is a radical of the formula (II) LibC/528071speci R 02 N- 2" N c H 2 (II) (taurolidine). The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in any one of claims 17 to 19, when used in a preparation at a concentration of 0.005 to 10.00% by weight 1,1-dioxoperhydro-1,2,4- thiadiazine including metabolites, in each case based on the total weight of the preparation.
21. The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in any one of claims 17 to when used in a preparation at a concentration of 0.01 5.0% by weight 1,1-dioxoperhydro-1,2,4- thiadiazine including metabolites, in each case based on the total weight of the preparation.
22. The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in any one of claims 17 to 21, when used in combination with further customary agents known per se which are effective against bad skin and acne. i* 23. The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in claim 22, wherein the further agent is a keratolytic.
24. The 1,1-dioxoperhydro-1,2,4-thiadiazine as claimed in claim 23, wherein the keratolytic is chosen from salicylic acid, lactic acid, glycolic acid, citric acid or malic acid. 15 Dated 20 October 2000 GOLDSCHMIDT AG 4 Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON e.. 4* LibC/528071speci
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19957383 | 1999-11-29 | ||
DE19957383 | 1999-11-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
AU6669400A true AU6669400A (en) | 2001-05-31 |
Family
ID=7930711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU66694/00A Abandoned AU6669400A (en) | 1999-11-29 | 2000-10-24 | Use of 1,1-dioxoperhydro-1,2,4-thiadiazines |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1103251A1 (en) |
JP (1) | JP2001342136A (en) |
KR (1) | KR20010016065A (en) |
AU (1) | AU6669400A (en) |
CA (1) | CA2325778A1 (en) |
NO (1) | NO20005856L (en) |
PL (1) | PL344146A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60311958T2 (en) * | 2003-02-03 | 2007-11-08 | Polaschegg, Hans-Dietrich, Dr. | Composition for the prevention of infections by subcutaneous prostheses |
CN108430476A (en) * | 2015-10-07 | 2018-08-21 | 科医公司 | The Cutaneous permeation preparation of Taurolidine |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1124285A (en) * | 1964-10-06 | 1968-08-21 | Geistlich Soehne Ag | Novel perhydro-1,2,4-thiadiazine dioxides-(1,1), their preparation and compositionscontaining them |
GB1385318A (en) * | 1971-01-29 | 1975-02-26 | Mediline Ag | Toiletry preparation for their hair |
DE4137544C2 (en) * | 1991-11-12 | 1998-07-30 | Kramer Axel | Antimicrobial combination of active ingredients based on oxygen-releasing compounds |
FR2771928B1 (en) * | 1997-12-05 | 2001-04-13 | Jean Noel Thorel | COMPOSITION COMPRISING TAURIN DERIVATIVES; ITS USE AS A CONSERVATIVE AGENT FOR A FOOD, OR PHARMACEUTICAL, TOPICAL OR COSMETIC PRODUCT |
-
2000
- 2000-10-18 KR KR1020000062188A patent/KR20010016065A/en not_active Application Discontinuation
- 2000-10-24 AU AU66694/00A patent/AU6669400A/en not_active Abandoned
- 2000-11-08 JP JP2000340102A patent/JP2001342136A/en active Pending
- 2000-11-10 CA CA002325778A patent/CA2325778A1/en not_active Abandoned
- 2000-11-16 EP EP00124974A patent/EP1103251A1/en not_active Withdrawn
- 2000-11-20 NO NO20005856A patent/NO20005856L/en not_active Application Discontinuation
- 2000-11-28 PL PL00344146A patent/PL344146A1/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
PL344146A1 (en) | 2001-06-04 |
KR20010016065A (en) | 2001-03-05 |
EP1103251A1 (en) | 2001-05-30 |
CA2325778A1 (en) | 2001-05-29 |
JP2001342136A (en) | 2001-12-11 |
NO20005856D0 (en) | 2000-11-20 |
NO20005856L (en) | 2001-05-30 |
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Legal Events
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MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |