WO1991001128A1 - Composition pour la peau permettant de reparer les effets du photovieillissement - Google Patents

Composition pour la peau permettant de reparer les effets du photovieillissement Download PDF

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Publication number
WO1991001128A1
WO1991001128A1 PCT/US1990/004052 US9004052W WO9101128A1 WO 1991001128 A1 WO1991001128 A1 WO 1991001128A1 US 9004052 W US9004052 W US 9004052W WO 9101128 A1 WO9101128 A1 WO 9101128A1
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WO
WIPO (PCT)
Prior art keywords
skin
forms
compound
moiety
carbon atoms
Prior art date
Application number
PCT/US1990/004052
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English (en)
Inventor
Neil Frederick Haley
Xina Nair
Gerard Joseph Gendimenico
F. Christopher Zusi
R. Thomas Swann
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Eastman Kodak Company
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Filing date
Publication date
Application filed by Eastman Kodak Company filed Critical Eastman Kodak Company
Priority to KR1019910700317A priority Critical patent/KR920700612A/ko
Publication of WO1991001128A1 publication Critical patent/WO1991001128A1/fr

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    • 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
    • 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
    • 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.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (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)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Les effets du photovieillissement ou déterioriation de la peau exposée au soleil, y compris la perte des fibres de collagène et la détérioration des petits vaisseaux sanguins dans le derme de la peau sont réparés en appliquant localement sur l'épiderme des quantités efficaces d'un composé ayant la structure (I) dans laquelle R1, R2, R3, R4 et R5 sont sélectionnés indépendamment dans le groupe comprenant H, Cl, OR6, un alkyl droit ou ramifié ayant de 1 à 10 atomes de carbone, NO2, COOR6, CN, OR6, NR6R7, NR6C(=S)NR7R8, NR6COR7, SO2NR6R7, CH(CH3)COOH, CONR6R7, COR6, OCONR6R7, NR6COONR7, R9OR6, NR6SO2R7, Si(CH3)3, et NR6CONR7R8, R3 forme avec R4 un cycle benzo ou, pris ensemble avec R2, forme un cycle benzo ou tétrahydrobenzo, ou ensemble avec R2 et R1 forme une moitié (1) ou, ensemble avec R2 une moitié (2), ou R2 forme avec R1 un cycle benzo, ou R2 forme avec R3 une moitié (3) ou (4) ou (5) ou (6), ou R1 est sélectionné indépendamment dans le groupe comprenant la fraction (7), (8); R6, R7 et R8 sont sélectionnés indépendamment dans le groupe comprenant un alkyl droit ou ramifié contenant de 1 à 10 atomes de carbone, un aryl contenant de 6 à 10 atomes de carbone et de l'hydrogène, et R9 représente un alkylène ayant de 1 à 6 atomes de carbone, et leurs complexes de carbonyle de fer, sur une région de la peau, en une quantité suffisante pour réparer les effets de l'élastose dans la peau. Ainsi, il est possible de prévenir et de réduire les lignes et rides de la peau dues au vieillissement.
PCT/US1990/004052 1989-07-25 1990-07-19 Composition pour la peau permettant de reparer les effets du photovieillissement WO1991001128A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019910700317A KR920700612A (ko) 1989-07-25 1990-07-19 광선에 의해 노화된 피부를 재생시키기 위한 치료 방법

Applications Claiming Priority (4)

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US38494989A 1989-07-25 1989-07-25
US384,949 1989-07-25
US55272790A 1990-07-16 1990-07-16
US552,727 1990-07-16

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WO1991001128A1 true WO1991001128A1 (fr) 1991-02-07

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EP (1) EP0436010A1 (fr)
JP (1) JPH04500824A (fr)
KR (1) KR920700612A (fr)
CA (1) CA2035459A1 (fr)
HU (1) HUT62193A (fr)
WO (1) WO1991001128A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR900100632A (en) * 1990-08-24 1992-08-31 Eastman Kodak Co Skin treatment and method for the restoration of the skin against sun effects
WO1995035105A1 (fr) * 1994-06-18 1995-12-28 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Systeme therapeutique transdermique a principes actifs constituant des sources de monoxyde de carbone
EP0734371A1 (fr) * 1993-12-15 1996-10-02 Avon Products, Inc. Nouveaux composes conjugues de retinoides et procedes de traitement du vieillissement de la peau
US6423854B1 (en) * 1997-08-27 2002-07-23 L'oreal Aminophenol derivatives and their use in cosmetics
WO2002092075A2 (fr) * 2001-05-15 2002-11-21 Northwick Park Institute For Medical Research Emission therapeutique de monoxyde de carbone
US7011854B2 (en) 2002-02-04 2006-03-14 Alfama-Investigacao e Desenvolvimento de Produtos Farmaceuticos Lda Method for treating a mammal by administration of a compound having the ability to release CO, compounds having the ability to release CO and pharmaceutical compositions thereof
US7166744B2 (en) * 2001-05-29 2007-01-23 Chebigen Co., Ltd. Retinoid derivatives and methods for producing said compounds and anti-cancer pharmaceutical composition comprising said compounds
WO2013019978A1 (fr) * 2011-08-03 2013-02-07 State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Portland State University Détection de fluorescence de cystéine et d'homocystéine
WO2013127380A1 (fr) 2012-02-29 2013-09-06 Friedrich-Schiller-Universität Jena Matériaux libérant du monoxyde de carbone et utilisation desdits matériaux
US9062089B2 (en) 2011-07-21 2015-06-23 Alfama, Inc. Ruthenium carbon monoxide releasing molecules and uses thereof
US9163044B2 (en) 2011-04-19 2015-10-20 Alfama, Inc. Carbon monoxide releasing molecules and uses thereof
US11020334B2 (en) * 2017-02-17 2021-06-01 Illustris Pharmaceuticals, Inc. Compounds, compositions and use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2938041A1 (de) * 1978-09-22 1980-04-03 Eugene J Van Scott Verfahren zur herstellung von retinoylhydroxysaeurederivaten und arzneimittel, das diese verbindungen enthaelt
JPS6163609A (ja) * 1984-09-04 1986-04-01 Takasago Corp チロシナ−ゼ活性阻害剤
US4595696A (en) * 1985-09-13 1986-06-17 Usv Pharmaceutical Corp. Polyene compounds useful in the treatment of allergic responses
EP0258481A1 (fr) * 1986-09-04 1988-03-09 Nisshin Flour Milling Co., Ltd. Compositions pharmaceutiques pour le traitement des maladies de la peau

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2938041A1 (de) * 1978-09-22 1980-04-03 Eugene J Van Scott Verfahren zur herstellung von retinoylhydroxysaeurederivaten und arzneimittel, das diese verbindungen enthaelt
JPS6163609A (ja) * 1984-09-04 1986-04-01 Takasago Corp チロシナ−ゼ活性阻害剤
US4595696A (en) * 1985-09-13 1986-06-17 Usv Pharmaceutical Corp. Polyene compounds useful in the treatment of allergic responses
EP0258481A1 (fr) * 1986-09-04 1988-03-09 Nisshin Flour Milling Co., Ltd. Compositions pharmaceutiques pour le traitement des maladies de la peau

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STN Filesupplier, Karlsruhe, DE, CHEMICAL ABSTRACTS, Volume 105, No. 8, 1990, American Chemical Society, see Abstract No. 66255e & JP, A, 61063609 (Showa) 1 April 1986 *

Cited By (22)

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GR900100632A (en) * 1990-08-24 1992-08-31 Eastman Kodak Co Skin treatment and method for the restoration of the skin against sun effects
EP0734371A1 (fr) * 1993-12-15 1996-10-02 Avon Products, Inc. Nouveaux composes conjugues de retinoides et procedes de traitement du vieillissement de la peau
EP0734371A4 (fr) * 1993-12-15 1997-03-05 Avon Prod Inc Nouveaux composes conjugues de retinoides et procedes de traitement du vieillissement de la peau
WO1995035105A1 (fr) * 1994-06-18 1995-12-28 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Systeme therapeutique transdermique a principes actifs constituant des sources de monoxyde de carbone
US5882674A (en) * 1994-06-18 1999-03-16 Lts Lohmann Therapie-Systeme Gmbh Transdermal therapeutic system comprising active substances representing carbon monoxide sources
US6423854B1 (en) * 1997-08-27 2002-07-23 L'oreal Aminophenol derivatives and their use in cosmetics
EP2135605A2 (fr) 2001-05-15 2009-12-23 Hemocorm Limited Emission thérapeutique de monoxyde de carbon
WO2002092075A2 (fr) * 2001-05-15 2002-11-21 Northwick Park Institute For Medical Research Emission therapeutique de monoxyde de carbone
WO2002092075A3 (fr) * 2001-05-15 2004-01-08 Northwick Park Inst For Medica Emission therapeutique de monoxyde de carbone
EP2135605A3 (fr) * 2001-05-15 2010-07-14 Hemocorm Limited Emission thérapeutique de monoxyde de carbon
US7045140B2 (en) 2001-05-15 2006-05-16 Hemocorm Limited Therapeutic delivery of carbon monoxide
US7166744B2 (en) * 2001-05-29 2007-01-23 Chebigen Co., Ltd. Retinoid derivatives and methods for producing said compounds and anti-cancer pharmaceutical composition comprising said compounds
US7011854B2 (en) 2002-02-04 2006-03-14 Alfama-Investigacao e Desenvolvimento de Produtos Farmaceuticos Lda Method for treating a mammal by administration of a compound having the ability to release CO, compounds having the ability to release CO and pharmaceutical compositions thereof
US9023402B2 (en) 2002-02-04 2015-05-05 ALFAMA—Investigação e Desenvolvimento de Produtos Farmacêuticos, Lda. Method for treating a mammal by administration of a compound having the ability to release CO
US9163044B2 (en) 2011-04-19 2015-10-20 Alfama, Inc. Carbon monoxide releasing molecules and uses thereof
US9062089B2 (en) 2011-07-21 2015-06-23 Alfama, Inc. Ruthenium carbon monoxide releasing molecules and uses thereof
US9611286B2 (en) 2011-07-21 2017-04-04 Alfama, Inc. Ruthenium carbon monoxide releasing molecules and uses thereof
WO2013019978A1 (fr) * 2011-08-03 2013-02-07 State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Portland State University Détection de fluorescence de cystéine et d'homocystéine
US9229007B2 (en) 2011-08-03 2016-01-05 Portland State University Fluorescence detection of cysteine and homocysteine
US9709572B2 (en) 2011-08-03 2017-07-18 Portland State University Fluorescence detection of cysteine and homocysteine
WO2013127380A1 (fr) 2012-02-29 2013-09-06 Friedrich-Schiller-Universität Jena Matériaux libérant du monoxyde de carbone et utilisation desdits matériaux
US11020334B2 (en) * 2017-02-17 2021-06-01 Illustris Pharmaceuticals, Inc. Compounds, compositions and use thereof

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HUT62193A (en) 1993-04-28
KR920700612A (ko) 1992-08-10
CA2035459A1 (fr) 1991-01-26
HU906129D0 (en) 1991-07-29
EP0436010A1 (fr) 1991-07-10
JPH04500824A (ja) 1992-02-13

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