EP0436010A1 - Zusammensetzung zur behandlung von sonnengeschädigter haut - Google Patents
Zusammensetzung zur behandlung von sonnengeschädigter hautInfo
- Publication number
- EP0436010A1 EP0436010A1 EP90911845A EP90911845A EP0436010A1 EP 0436010 A1 EP0436010 A1 EP 0436010A1 EP 90911845 A EP90911845 A EP 90911845A EP 90911845 A EP90911845 A EP 90911845A EP 0436010 A1 EP0436010 A1 EP 0436010A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- skin
- compound
- forms
- carbon atoms
- independently selected
- 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.)
- Ceased
Links
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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
- A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate
-
- 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
- A61Q19/004—Aftersun preparations
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- 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
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- 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
- A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
-
- 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
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/58—Metal complex; Coordination compounds
Definitions
- This invention relates to a method of repairing the effects of aging of the skin
- photoaging is most prominent in light skinned persons who brown easily and tan poorly. The effects of sunlight are cumulative. As a result, this sunlight-induced skin damage has been referred to as photoaging.
- sunscreen agents The majority of signs of photoaging can be prevented by judicious use of topically applied sunscreen agents. It is important to use sunscreens early in life, for example, as soon as a child begins to spend a significant amount of time outdoors.
- the present invention relates to the use of specific polyenes in repairing the aging changes of exposed areas of the skin, especially the face.
- the method of the invention comprises the repairing of sun-damaged skin comprising topically administering a compound having the structure:
- R 1 , R 2 , R 3 , R 4 and R 5 are
- R 3 together with R 4 forms a benzo ring or taken together with R 2 forms a benzo or
- R 2 together with R 1 forms a benzo ring or R 2 together with R 3 forms a
- R 1 is independently selected from the group consisting of
- R 6 , R 7 and R 8 are independently
- R 9 is alkylene of 1 to 6 carbon atoms, and iron carbonyl complexes thereof, to an area of the skin in an amount
- the polyenes may be applied to the skin in any non-toxic, dermatologically acceptable vehicle, preferably a non-volatile emollient or lubricating vehicle in varied concentrations which is more fully described hereinbelow.
- the treatment of skin with the polyenes of the present invention moderate and retard the aging changes in the skin to both the dermis and the epidermis. As age and exposure to sunlight
- the skin's cells divide at a slower rate.
- the thickness of the epidermis decreases and the horny layer which protects against water loss sheds cells in large groups, resulting in rough, dry and scaling skin.
- the cells which make up the fiber of the dermis become smaller with increasing age with a loss of collagen fibers. The degradation of these fibers contributes to wrinkling and loss of elasticity.
- polyene compounds useful in the present invention have the structure:
- R 1 , R 2 , R 3 , R 4 and R 5 are
- R 3 together with R 4 forms a benzo ring or taken together with R 2 forms a benzo or
- R 2 together with R 1 forms a benzo ring or R 2 together with R 3 forms a
- R 1 is independently selected from the group consisting of
- R 6 , R 7 and R 8 are independently
- R 9 is alkylene of 1 to 6 carbon atoms, such as methylene, propylene, butylene, trimethylene, etc.
- alkyl of 1 to 10 carbon atoms examples are methyl, butyl, pehtyl, octyl, ethyl, tertiary-butyl, benzyl,
- isopropyl, chloroethyl, chloropropyl, hydroxypropyl, carboxyethyl, carboxymethyl, phenynyl, cyanoethyl, and 2-ethylhexyl and aryl of 6 to 10 carbon atoms are exemplified by phenyl and napthyl.
- the compounds are formed by reaction of polyene acids with acetic anhydride, boron
- Useful polyenes within the scope of the present invention include those with the following structures:
- the therapeutic agents of this invention may be administered alone or in combination with
- pharmaceutically-acceptable carriers the proportion of which is determined by the solubility and chemical nature of the compound, chosen route of
- excipients as starch, milk, sugar, certain of clay and so forth. They may be administered orally in the form of solutions which may contain coloring or flavoring agents. When applied topically for
- any of the commonly employed extending agents can be used depending on the nature of the product as is well-known in the art.
- the physician will determine the dosage of the present theraputic agents which will be most suitable and it will vary with the form of
- the polyenes which are formulated in moisturi- zing bases such as creams or ointments are usually provided in low concentrations.
- Compound I may be used in concentrations of about 0.001 percent to 10 percent and preferably about 0.01 percent to 5 percent by weight of the base.
- Other non-toxic, dermatologically acceptable vehicles or carriers in which the polyenes are stable will be evident to those of ordinary skill in the art.
- emollient or lubricating vehicles such as oleaginous substances, which help hydrate the skin are preferred.
- “emollient” will be understood to refer to the non-irritating character of the composition as a whole. That is, the nature of the vehicle and amount of polyene therein should be selected so as to provide a sub-irritating dose for topical application. Volatile vehicles which dry or otherwise harm the skin, such as alcohol and acetone, should be avoided.
- An ointment base (without water) is preferred in the winter and in subjects with very dry skin.
- suitable ointment bases are petrolatum, petrolatum plus volatile silicones, lanolin, and water in oil emulsions, such as Eucerin (Beiersdorf).
- cream bases In warm weather and often for younger persons, oil in water emulsion (cream) bases, are preferred.
- suitable cream bases are Nivea Cream (Beiersdorf), cold cream (USP), Purpose Cream (Johnson &. Johnson), hydrophilic ointment
- the length of treatment of human skin can vary. Usually, there is little point in beginning the treatments of the present invention until young adult life or, more typically, in middle age, when the effects of aging begin to appear.
- the particular program of maintenance therapy according to the present invention will vary depending upon the individual and conditions being treated. Generally, depending upon the age and state of the skin when treatments begin, it has been found that once a day applications of polyenes for up to two months may be necessary to reduce and control the effects of aging which have already occurred. Once a stabilized skin control has been obtained, the frequency of application of the polyenes may be reduced, for example to two or three times a week, and in some cases only once a week for the rest of the person's life. That is, once the aging process has been controlled, a maintenance dose on the order of two applications per week is generally sufficient to maintain that state.
- compositions of this invention can, if desired, contain suitable sunscreen agents. Any conventional sunscreen agent can be utilized in formulating the polyenes formulations which can be utilized in accordance with this invention.
- topical compositions can contain any of the conventional excipients and additives commonly used in preparing topical compositions.
- the conventional additives or excipients which can be utilized in preparing these cosmetic compositions in accordance with this invention are preservatives, thickeners, perfumes and the like.
- the conventional antioxidants such as butylated hydroxyanisoles (BHA), ascorbyl palmitate, propyl gallate, citric acid butylated hydroxy toluene (BHT), ethoxyquin and the like can be incorporated into these compositions.
- BHA butylated hydroxyanisoles
- BHT citric acid butylated hydroxy toluene
- ethoxyquin ethoxyquin and the like
- compositions may contain thickening agents, humectants, emulsifying agents and viscosity stabilizers, such as those generally utilized.
- these compositions can contain flavoring agents, colorants, and perfume which are conventional in preparing cosmetic compositions. This invention is further illustrated by the following examples, which are illustrative only.
- Compound II was tested for its effect on the differentiation of epidermis and dermis in hairless mice and directly compared to all-trans retinoic acid.
- polyene compounds related to vitamin A including all-trans retinoic acid, are highly effective in reducing the size of horn-filled utricles in hairless rhino mouse skin.
- the number of interutricular epidermal cells layers increases, coneomitantly, as the size of the utricles diminish. Increased numbers of epidermal cell layers are also prominent in human photoaged skin treated with all-trans retinoic acid.
- Hairless rhino mice (hr rh hr rh ) from Temple University Skin and Cancer Hospital were treated with 0.05 ml of Compound II, all-trans retinoic acid or the ethanol : acetone (1:1) vehicle on the dorsolateral skin once daily on five consecutive days, for four weeks. Mice were sacrificed by CO 2 on the third day after the last treatments. A 7/8" punch biopsy of skin was removed and bisected in half. One of the halves was placed in 0.5 percent acetic acid overnight at 4°C so that horizontal epidermal sheets could be removed from each biopsy. The following day, epidermal sheets were removed from the dermis by peeling with a metal spatula.
- H&E hematoxylin and eosin
- Compound II has marked activity over a wide concentration range, identical to all-trans retinoic acid.
- Compound II was as effective as all-trans retinoic acid in increasing the interutricular epidermal thickness of rhino mice. This increase in epidermal thickness was due to an increase in the number of epidermal cell layers.
- Polyene compounds are also evaluated for their effects on epidermal differentiation when they are applied to a non-wrinkled strain of hairless mice (hrhr). These mice have fewer horn-filled utricles in their skin compared to rhino mice.
- a variety of polyene compounds induce an increase in the number of epidermal cell layers when a compound is applied once to dorsal skin.
- mice were sacrificed by CO 2 and a 7/8" punch biopsy from the treated skin was removed and placed into 10 percent buffered formalin. H&E-stained vertical sections were prepared and the epidermal thickness in the interfollicular areas was measured with an image analyzer.
- Compound II caused the same degree of epidermal hyperplasia as the three equivalent concentrations of all-trans retinoic acid.
- All-trans retinoic acid is known to affect the differentiation of cells in the dermis of hairless mouse skin, most effectively in the skin of mice that have been damaged by UV radiation.
- the formation of a new zone of connective tissue is accelerated in photoaged hairless mouse skin by topical treatment with all-trans retinoic acid. This is due to an increased number of fibroblasts and an increase in their metabolic activity. As a result, new
- mice Female hairless mice (Skh-HR1), six to eight weeks old, obtained from Temple University Skin and Cancer Hospital, had their dorsal skin irradiated with ultraviolet B (UVB) radiation on Monday, Wednesday and Friday each week for ten weeks, using a bank of eight Westinghouse FS-40 sunlamps placed 16 cm above the back of the mice. During the first three weeks, the radiation dose per day was progressively increased from one minimal erythemal dose (MED) to four MED's. The 4-MED dose per day was then continued for the last seven weeks.
- UVB ultraviolet B
- mice were sacrificed by cervical dislocation and dorsal skin was removed and placed in 10 percent buffered formalin. Parafin-embedded sections were cut at 10 ⁇ m
- the dermal repair zone was measured microscopically and is defined as the area from the epidermal-dermal border to the top of the compressed elastotic material.
- a rabbit model of skin irritation was used to assess the dermatitis produced by treatment with Compound II and all-trans retinoic acid.
- the rabbit is commonly used as a skin irritation model for predicting the potential local irritation of
- New Zealand albino rabbits from Beckens Farms, Sanborn, N.Y., were clipped closely at four sites on the back with an electric hair clipper to give 4 cm X 4 cm square sites. Each rabbit received 0.2 ml of Compound II and all-trans retinoic acid, once daily for fourteen consecutive days. Each day, the degree of erythema, scaling and edema was
- the results were expressed as average daily Draize score, which was derived by taking the cumulative score over fourteen days, for each parameter, and dividing by fourteen.
- Table 5 shows a comparison of three doses of Compound II (0.1, 0.01 and 0.001 percent) to 0.01 percent all-trans retinoic acid.
- Global Irritation score is defined as the sum of the
- Vitamin A-related polyene compounds cause multiple signs of toxicity, referred to as the
- hypervitaminosis A syndrome characterized by loss of body weight, skin scaling, hair loss and bone
- mice were graded daily during treatment for signs of hypervitaminosis A by the method of Bollag.
- An animal is defined as having hypervitaminosis A when addition of the grades for loss of body weight, skin scaling, hair loss and bone fractures totals at least three.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38494989A | 1989-07-25 | 1989-07-25 | |
US384949 | 1989-07-25 | ||
US55272790A | 1990-07-16 | 1990-07-16 | |
US552727 | 1995-11-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0436010A1 true EP0436010A1 (de) | 1991-07-10 |
Family
ID=27010824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90911845A Ceased EP0436010A1 (de) | 1989-07-25 | 1990-07-19 | Zusammensetzung zur behandlung von sonnengeschädigter haut |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0436010A1 (de) |
JP (1) | JPH04500824A (de) |
KR (1) | KR920700612A (de) |
CA (1) | CA2035459A1 (de) |
HU (1) | HUT62193A (de) |
WO (1) | WO1991001128A1 (de) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GR1000937B (el) * | 1990-08-24 | 1993-03-16 | Eastman Kodak Co | Μέ?οδος δια την αγωγή δέρματος προς αποκατάσταση των αποτελεσμάτων της φωτογηράνσεως. |
JPH09509403A (ja) * | 1993-12-15 | 1997-09-22 | エイボン プロダクツ インコーポレイテッド | 新規なレチノイド共役体化合物及び皮膚老化を処置するための方法 |
DE4421433C1 (de) * | 1994-06-18 | 1995-06-08 | Lohmann Therapie Syst Lts | Transdermales therapeutisches System mit Wirkstoffen, die Kohlenmonoxid-Quellen darstellen, Verfahren zu seiner Herstellung und seine Verwendung |
FR2767823B1 (fr) * | 1997-08-27 | 1999-10-15 | Oreal | Composes derives d'aminophenol et leur utilisation en cosmetique |
GB0111872D0 (en) | 2001-05-15 | 2001-07-04 | Northwick Park Inst For Medica | Therapeutic agents and methods |
DE60234024D1 (de) * | 2001-05-29 | 2009-11-26 | Chebigen Co Ltd | Neue retinoidderivate und eine pharmazeutische anti-krebs-zusammensetzung, die diese verbindungen enthält |
WO2003066067A2 (en) | 2002-02-04 | 2003-08-14 | Alfama - Investigaçao E Desenvolvimento De Produtos Farmaceuticos Lda. | Use of co-releasing compounds for the manufacture of a medicament for the treatment of inflammatory diseases |
US9163044B2 (en) | 2011-04-19 | 2015-10-20 | Alfama, Inc. | Carbon monoxide releasing molecules and uses thereof |
JP6134710B2 (ja) | 2011-07-21 | 2017-05-24 | アルファーマ インコーポレイテッドAlfama,Inc. | 一酸化ルテニウム放出分子およびその使用 |
US9229007B2 (en) | 2011-08-03 | 2016-01-05 | Portland State University | Fluorescence detection of cysteine and homocysteine |
DE102012004132A1 (de) | 2012-02-29 | 2013-08-29 | Friedrich-Schiller-Universität Jena | Kohlenstoffmonoxid freisetzende Materialien und deren Verwendung |
US11020334B2 (en) * | 2017-02-17 | 2021-06-01 | Illustris Pharmaceuticals, Inc. | Compounds, compositions and use thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4216224A (en) * | 1978-09-22 | 1980-08-05 | Scott Eugene J Van | Methods and compositions for treating psoriasis with retinoyl compounds |
JPS6163609A (ja) * | 1984-09-04 | 1986-04-01 | Takasago Corp | チロシナ−ゼ活性阻害剤 |
JPS61207332A (ja) * | 1985-03-12 | 1986-09-13 | Nisshin Kagaku Kk | 皮膚疾患治療剤 |
US4595696A (en) * | 1985-09-13 | 1986-06-17 | Usv Pharmaceutical Corp. | Polyene compounds useful in the treatment of allergic responses |
-
1990
- 1990-07-19 CA CA002035459A patent/CA2035459A1/en not_active Abandoned
- 1990-07-19 HU HU906129A patent/HUT62193A/hu unknown
- 1990-07-19 WO PCT/US1990/004052 patent/WO1991001128A1/en not_active Application Discontinuation
- 1990-07-19 JP JP2511067A patent/JPH04500824A/ja active Pending
- 1990-07-19 EP EP90911845A patent/EP0436010A1/de not_active Ceased
- 1990-07-19 KR KR1019910700317A patent/KR920700612A/ko not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO9101128A1 * |
Also Published As
Publication number | Publication date |
---|---|
JPH04500824A (ja) | 1992-02-13 |
CA2035459A1 (en) | 1991-01-26 |
HUT62193A (en) | 1993-04-28 |
HU906129D0 (en) | 1991-07-29 |
WO1991001128A1 (en) | 1991-02-07 |
KR920700612A (ko) | 1992-08-10 |
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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 |
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17P | Request for examination filed |
Effective date: 19910223 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB IT LI LU NL SE |
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RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: EASTMAN KODAK COMPANY |
|
17Q | First examination report despatched |
Effective date: 19920727 |
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