WO1985004577A1 - Compositions used for hair growth - Google Patents
Compositions used for hair growth Download PDFInfo
- Publication number
- WO1985004577A1 WO1985004577A1 PCT/US1985/000556 US8500556W WO8504577A1 WO 1985004577 A1 WO1985004577 A1 WO 1985004577A1 US 8500556 W US8500556 W US 8500556W WO 8504577 A1 WO8504577 A1 WO 8504577A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- dihydro
- pyrimidine
- butyl
- pyridyl
- Prior art date
Links
- 0 C1CC*CC1 Chemical compound C1CC*CC1 0.000 description 2
Classifications
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
Definitions
- the present invention relates to topical application of Compounds A, B, C, D, series and methyl 5- ⁇ 3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H- ⁇ 1, 2, 4> oxadiazolo 2,3,- ⁇ > pyrimidine-7-carbamate and their active analogs and derivatives for improving the rate of hair growth on mammalian skins and for the treatment of alopecia, as well as the use of the forementioned compounds and their analogs with retinoids.
- a normal characteristic of hair growth in mammals, including human, is that in most cases the rate of hair growth and the length of its growth cycle are reduced with age. These phenomena are common to all mammals with rare exceptions and they must be differentiated from true male pattern alopecia.
- United States Patent No. 4,139,619 issued to Charles A. Chidsey on February 13, 1979 discloses a process for stimulating the growth of mammalian hair by topical application of certain preparations containing, as the active ingredient, 6-amino-4 (substituted amino)-1,2-dehydro-1-hydroxy-2-iminopyrimidine.
- This patent further states that the active compounds and the methods of their preparations are disclosed in United States Patent No. 3,461,461, which was issued on August 12, 1969.
- Most examples in the patent to Chidsey describe various preparations such as topical cream, topical ointment, solution, aerosol and dusting powder, and state that these preparations can be applied to the bald human scalp to stimulate the rate of growth of terminal hair.
- compositions for topical applications to mammalian skin, in combination with retinoids, in order to stimulate or improve the rate of hair growth thereon and to prolong the anagen phase of the hair cycle.
- the subject compounds when applied to a mammalian skin, in an effective amount, stimulate or improve the rate of hair growth and prolong the anagen phase of the hair cycle. Moreover, these compounds have also been found to be effective in treatment of alopecia. Typically, these compounds constitute the active ingredients of different types of preparations such as lotions, solutions, ointments, creams, sprays and the like.
- the compounds of the present invention which form the active ingredients in the hair treatment preparations include Compounds A, B, C, D, series and methyl 5- ⁇ 3, 6-dihydro-1(2H)-pyridyl-2-oxo-2H— ⁇ 1 , 2, 4>oxadiaolo ⁇ 2, 3- ⁇ >pyrimidine-7-carbamate or their active derivatives or analogs. Furthermore, combinations of these compounds with retinoids as described in PCT U.S./00338 and PCT U.S. 82/01593 exhibit synergism in that they improve or stimulate the rate of hair growth to a greater extent than the individual active ingredients of the combination alone.
- Suitable retinoid active ingredients for use in this invention include derivatives of retinoic acid which have been described in PCT applications: U.S. 81/00338 and U.S. 82/01593.
- Preparations such as lotions, creams, conditioners, and the like, including the aforementioned compounds as the active ingredients, can be applied topically to the skin for stimulating or improving the rate of hair growth. It has surprisingly been discovered that the compounds of the present invention, in comparison with minoxidil, when applied topically to the skin have excellent penetration and a long lasting effect, in producing hair growth in an animal model for androgenetic alopecia. Furthermore, retinoids in combination with the subject compounds of this application exhibit synergism in the animal model studied.
- retinoid denotes retinol, retinal, retinyl esters as well as retinoic acid and its esters, amides, derivatives, analogs and metabolites.
- the terminal groups may be oxidized, reduced, esterifled, etc.
- the alkali metal (sodium, potassium, etc.) and alkaline earth metals (magnesium, zinc, calcium, etc.) salts of these compounds are also included herein.
- the pharmaceutical, cosmetic or veterinary preparations of the present invention can be prepared by conventional techniques for the preparation of lotions, creams, conditioners or shampoos for the scalp or veterinary preparations for pelis. Included also are preparations which can be administered orally and compounds which can be added to animal foods.
- the various preparations can contain any conventional pharmaceutically acceptable or cosmetically acceptable inert or pharmacodynamically active additives or carriers.
- the lotions may be prepared using various forms of alcohols or other solubilizers such as glycols, or esters.
- the conditioners may contain the normally acceptable commercially produced compounds such as cetyl alcohol, ceteareth-5, -20 hydrantoins, hydrolyzed animal protein, blycol stearate, amodimethicone, paraffin, mineral oil, etc.
- the topical compounds may also contain various oils including essential fatty acids and phospholipids and other polyunsaturated fatty acids and their derivatives and.
- the topically applied lotions, creams, and conditioners, etc. will vary according to the standard art with regard to the amounts of other hydrophilic and hydrophobic containing ingredients, including emulsifiers, so that either an oily, semi-oily or oil-free product may be obtained.
- the shampoos may contain any of the conventionally used detergents or soaps and any other compounds used by those familiar with the art. Oil-based shampoos are included in these formulations.
- the topical treatments may consist of lotions, creams, conditioners, shampoos, oil treatments, etc., with from 0.001 to 5% by weight of the active ingredients, Compounds A, B, C, D, series and all-trans retinoic acid or derivatives, or other retinoids, as the preferred dosages in these compositions.
- R can be equal to : R can be equal to
- R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl, e) methoxy ethyl or f) allyl
- R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl, e) benzyl, or f) 2-methoxy ethyl
- Components Weight % Active Ingredient Compound A methyl-5-[3,6-dihydro-1(2H)-pyridyl] 1.0 -2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate
- the water washable cream ointment thus prepared consists of 0.1% retinoic acid ingredient and 3% of Compound A (methyl-5-[3,6-dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate).
- Cream Conditioner for Topical Administration Weight %
Abstract
The use of substituted pyrimidines designated as compounds A, B, C, D, series and methyl 5-<3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H-<1, 2, 4>oxadiazolo<2, 3, -alpha>pyrimidine-7-carbamate and their active derivatives and analogs and combinations of these with retinoids to increase the rate of hair growth and to prolong the anagen phase of the hair cycle and to treat certain types of alopecia.
Description
COMPOSITIONS USED FOR HAIR GROWTH Description
Brief Summary of the Invention:
Methyl 5-<3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H-<1, 2, 4> oxadiazolo<2, 3, -α> pyrimidine-7-carbamate and Compounds A, B, C, D, E, F, series and their active derivatives and analogs, when applied topically to the skin of mammals, or administered orally, stimulate or improve the rate of hair growth and they exhibit effectiveness in the treatment of alopecia. Furthermore, retinoids and analogs, and mixtures of .these compounds with Compounds A, B, C, D, series and methyl 5-<3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H-<1, 2, 4>oxadiazolo<2, 3, -α>pyrimidine-7-carbamate and their active derivatives and analogs, when applied topically to the skin of mammals, or administered orally, stimulate or improve the rate of hair growth and they exhibit effectiveness in the treatment of alopecia.
Related Applications:
This application is related in part to application serial U.S. 235,169, filed February 17, 1981; application serial U.S. 318,607, filed November 9, 1981; application serial U.S. 386,730 filed June 9, 1982, and application serial U.S. 414,854 filed September 3, 1982. The compounds claimed in this application are disclosed in applications and patents listed as follows: German Offen. 2,804,518, filed August 17, 1978; U.S. Patents 4,220,772 and 4,256,886; German Offen. 2,804,519, filed August 10, 1978; Swiss Applic. 78/7,910, filed July 21, 1978: Helvetica Chimica Acta Vol. 65 Fasc. 5 (1982), pp. 1445-1467, Helvetica Chimica Acta Vol. 66 Fasc. 2 (1983), pp. 669-672: U.S. Patents 4,150,131 and 4,360,521, and Belgium patent No. 893,833, filed January 14, 1983 and CH. application 81/4,640, filed July 15, 1981.
Background of the Invention:
The present invention relates to topical application of Compounds A, B, C, D, series and methyl 5-<3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H-<1, 2, 4> oxadiazolo 2,3,-α> pyrimidine-7-carbamate and their active analogs and derivatives for improving the rate of hair growth on mammalian skins and for the treatment of alopecia, as well as the use of the forementioned compounds and their analogs with retinoids.
A normal characteristic of hair growth in mammals, including human, is that in most cases the rate of hair growth and the length of its growth cycle are reduced with age. These phenomena are common to all mammals with rare exceptions and they must be differentiated from true male pattern alopecia.
United States Patent No. 4,139,619 issued to Charles A. Chidsey on February 13, 1979 discloses a process for stimulating the growth of mammalian hair by topical application of certain preparations containing, as the active ingredient, 6-amino-4 (substituted amino)-1,2-dehydro-1-hydroxy-2-iminopyrimidine. This patent further states that the active compounds and the methods of their preparations are disclosed in United States Patent No. 3,461,461, which was issued on August 12, 1969. Most examples in the patent to Chidsey describe various preparations such as topical cream, topical ointment, solution, aerosol and dusting powder, and state that these preparations can be applied to the bald human scalp to stimulate the rate of growth of terminal hair.
International Application Numbers PCT/US81/00338 and PCT/US82/01593 by applicant Gail Bazzanσ disclose chemical compositions containing retinoids and retinoids and minoxidil which can be used to increase the rate of growth of hair and to treat alopecias.
It is the object of the present invention to provide additional compositions or preparations which are effective in improving the rate of hair growth on mammalian skin, as described and listed on Pages 9,10,11 of this patent application.
It is also the object of this invention to provide such compositions for topical applications to mammalian skin, in combination with retinoids, in order to stimulate or improve the rate of hair growth thereon and to prolong the anagen phase of the hair cycle.
The foregoing and other objects and advantageous features of this invention will be more clearly comprehended from the following detailed description.
Detailed Description of the Invention:
It has been unexpectedly discovered that the subject compounds, when applied to a mammalian skin, in an effective amount, stimulate or improve the rate of hair growth and prolong the anagen phase of the hair cycle. Moreover, these compounds have also been found to be effective in treatment of alopecia. Typically, these compounds constitute the active
ingredients of different types of preparations such as lotions, solutions, ointments, creams, sprays and the like.
The compounds of the present invention which form the active ingredients in the hair treatment preparations include Compounds A, B, C, D, series and methyl 5-<3, 6-dihydro-1(2H)-pyridyl-2-oxo-2H—<1 , 2, 4>oxadiaolo<2, 3-α>pyrimidine-7-carbamate or their active derivatives or analogs. Furthermore, combinations of these compounds with retinoids as described in PCT U.S./00338 and PCT U.S. 82/01593 exhibit synergism in that they improve or stimulate the rate of hair growth to a greater extent than the individual active ingredients of the combination alone.
Suitable retinoid active ingredients for use in this invention include derivatives of retinoic acid which have been described in PCT applications: U.S. 81/00338 and U.S. 82/01593.
Preparations such as lotions, creams, conditioners, and the like, including the aforementioned compounds as the active ingredients, can be applied topically to the skin for stimulating or improving the rate of hair growth. It has surprisingly been discovered that the compounds of the present invention, in comparison with minoxidil, when applied topically to the skin have excellent penetration and a long lasting effect, in producing hair growth in an animal model for androgenetic alopecia. Furthermore, retinoids in combination with the subject compounds of this application exhibit synergism in the animal model studied.
As used herein, the term retinoid denotes retinol, retinal, retinyl esters as well as retinoic acid and its esters, amides, derivatives, analogs and metabolites. As described in PCT U.S. 82/01593, the terminal groups may be oxidized, reduced, esterifled, etc. The alkali metal (sodium, potassium, etc.) and alkaline earth metals (magnesium, zinc, calcium, etc.) salts of these compounds are also included herein.
The pharmaceutical, cosmetic or veterinary preparations of the present invention can be prepared by conventional techniques for the preparation of lotions, creams, conditioners or shampoos for the scalp or veterinary preparations for pelis. Included also are preparations which can be administered orally and compounds which can be added to animal foods.
In addition to the active compounds of this invention, the various preparations can contain any conventional pharmaceutically acceptable or cosmetically acceptable inert or pharmacodynamically active additives or carriers. For example, the lotions may be prepared using various forms of alcohols or other solubilizers such as glycols, or esters. The conditioners may contain the normally acceptable commercially produced compounds such as cetyl alcohol, ceteareth-5, -20 hydrantoins, hydrolyzed animal protein, blycol stearate, amodimethicone, paraffin, mineral oil, etc. The topical compounds may also contain various oils including essential fatty acids and phospholipids and other polyunsaturated fatty acids and their derivatives and. prostaglandins and prostacyclins and their derivatives and analogs and other compounds which can be vasodilators, vitamins or hormones. The topically applied lotions, creams, and conditioners, etc., will vary according to the standard art with regard to the amounts of other hydrophilic and hydrophobic containing ingredients, including emulsifiers, so that either an oily, semi-oily or oil-free product may be obtained. The shampoos may contain any of the conventionally used detergents or soaps and any other compounds used by those familiar with the art. Oil-based shampoos are included in these formulations.
The topical treatments may consist of lotions, creams, conditioners, shampoos, oil treatments, etc., with from 0.001 to 5% by weight of the active ingredients, Compounds A, B, C, D, series and all-trans retinoic acid or derivatives, or other retinoids, as the preferred dosages in these compositions.
methyl-5-[3,6-dihydro-1(2H)-pyridyl] methyl 2-amino-6-[3,6-dilιydro-1
-2-oxo-2H-[1,2,4]-cxadiazolo[2,3-a] (2H)-pyridyl]-4-pyrimidlne carpyrimidine-7-carbamate bamate-3-oxide
R=methyl R=methyl
R can be equal to : R can be equal to
a methyl a methyl b ethyl b ethyl c butyl c butyl d i-butyl d i-butyl e benzyl e benzyl f 2-methoxy-ethyl f 2-methoxy-ethyl
R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl, e) methoxy ethyl or f) allyl
R Mp. (dec.) Molecular
[°C] formula
a methyl 215 C12H13N5O4 291.27 b ethyl 202-204 C13H15N5O4 305.30
c butyl 197-198 C15H19N5O4
333.35
d i-butyl 197-198 C1 5H19N5O4
333.35 e methoxy- 203-204 C14H17N5O5 ethyl 335.32 f allyl 207-209 C14H15N5O4
317.31
dimethyl-6-[3,6-dihydro-1(2H)-pyridyl]-2,4- pyrimidine dicarbamute- 3-oxide
R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl, e) benzyl, or f) 2-methoxy ethyl
4 R Mp. Molecular
[°C] formula
a methyl 202-206 C13H17N5O5
323.309 b ethyl 154-155 C15H21N5O5
351.363 c butyl 131-132 C19H29N5O5
401.471 d i-butyl 137-139 C19H29N5O5
401.471
e benzyl 172 C25H25N5O5
475.505
f 2-meth-126-128 C17H25N5O7 oxy- ethryl 411.415
Example 1
Topical Lotion
Components Weight % Active Ingredient: Compound A methyl-5-[3,6-dihydro-1(2H)-pyridyl] 1.0 -2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate
Active ingredient : All-trans retinoic acid 0. 1
Ethanol q.s. to 100.0
Propylene glycol 5.0 Butylated hydroxytoluene 0.1 Saf flower oil 1.0 2-tocopherol acetate 0.5
Example II
Topical Cream Conditioner
Components Weight %
Active Ingredient:
Compound B methyl 2-amino-6-[3,6-dihydro-1 5.0
(2H)-pyridyl]-4-pyrimidine carbamate-3-oxide
Active ingredient: Retinoic Acid 0.1
Distilled Water q.s. to 100.0
Cetrimonium Chloride 5.0
Cetyl alcohol 4.0
Ethanol 84.0
Butylated hydroxytoluene 1.0
Hydrolyzed animal protein 0.5
Methylparaben, propylparaben 0.1
Example III
3.0 grams of Compound A (methyl-5-[3,6-dihydro-1(2H)-pyridyl]-2-oxo-2H-[1, 2, 4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate) and 0.1 grams of 13-cis retinoic acid is dissolved in 10 ml. of acetone, and the solution admixed with 90 grams of USP grade hydrophilic ointment to a uniform consistency, one gram of butylated hydroxytoluene is then added to this mixture. The water washable cream ointment thus prepared consists of 0.1% retinoic acid ingredient and 3% of Compound A (methyl-5-[3,6-dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate).
Example IV
Lotion Formulation for the Topical Administration Weight %
Active Ingredient:
Compound DDImethyl-5-[3,6-dihydro-1(2H)-pyridyl] 1. 0 -2-oxo-2H-[1,2,4]-oxadiazolo[2,3-1] pyrimidine-7-carbamate Active ingredients: Retinoic Acid 0.1 Ethanol q. s. to 100.0
Propylene glycol 5.0 Butylated hydroxytoluene 0. 1 Safflower oil 1 .0 α-tocopherol acetate 0.5 Stabilizer 0.1
Example V
Cream Conditioner for Topical Administration Weight %
Active Ingredient:
Compound D dimethyl-6-[3,6-dihydro-1(2H)- pyridyl[-2,4-pyrimidine dicarbamate- 5.0 to 1. 0 3-oxide
Active ingredients: Retinoic Acid 0. 1
Distilled Water q. s. to 100 .0
Cetrimonium Chloride 5.0
Cetyl alcohol 4.0
Ethanol 84.0
Butylated hydroxytoluene 1.0
Hydrolized animal protein 0.5
Methylparaben, propylparaben 0. 1
Stabilizer 0.1
The aforementioned examples are only examples and are not meant to be limiting.
Claims
1. A composition useful for increasing the rate of hair growth on mammalian skins, prolonging the anagen phase of the hair cycle and for treating various types of alopecias, comprising an effective amount of a compound selected from the series consisting of Compound A: methyl-5-[3,6-dihydro-1(2H)pyridy1]-2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a]pyrimidine-7-carbamate and its active analogues, as described below.
methyl-5-[3,6-dihydro-1(2H)-pyridyl] -2-oxo-2H-[1,2,4]-cxadiazolo[2,3-a] pyrimidine-7-carbamate
R=methyl
R can be equal to :
a methyl b ethyl c butyl d i-butyl e benzyl f 2-methoxy-ethyl
2. A composition useful for increasing the rate of hair growth on mammalian skins, prolonging the anagen phase of the hair cycle and for treating various types of alopecias, comprising an effective amount of a compound selected from the series consisting of Compound B: methyl-2-amino-6-[3,6-dihydro-1(2H)-pyridyl]-4-pyrimidine carbamate-3-oxide and its active analogues, as described below.
methyl 2-amino-6-[3,6-dihydro-1 (2H)-pyridyl]-4-pyrimidine carbamate-3-oxide
R=methyl
R can be equal to
a methyl b ethyl c butyl d i-butyl e benzyl f 2-methoxy-ethyl
3. A composition useful for increasing the rate of hair growth and mammalian skins, prolonging the anagen phase of the hair cycle and for treating various types of alopecias, comprising an effective amount of a compound selected from the series consisting of Compound C: methyl-5-[3, 6-dihydro-1(2H)-pyridyl-2-oxo-2H-[1,2,4]-oxadiazolo[2,3-1]pyrimidine-7-carbamate, as described below.
R can be equal to: a) methyl, b) ethyl, c) butyl, d) i-butyl, e) methoxy ethyl f) allyl
4. A composition useful for increasing the rate of hair growth on mammalian skins, prolonging the anagen phase of the hair cycle and for treating various types of alopecias, comprising an effective amount of a compound selected from the series consisting of Compound D: dimethyl-6-[3,6-dihydro-1(2H)-pyridyl]-2,4-pyrimidine dicarbamate-3-oxide and its active analogues, as described below.
dimethyl-6-[3,6-dihydro-1(2H)-pyrldyl]-2,4- pyrimidine dicarbamate- 3-oxide
R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl e) benzyl or f) 2-methoxy ethyl
5. A composition useful for improving the rate of hair growth on mammalian skins which comprises topically applying to the skin an effective amount of a compound selected from the group consisting of retinoid, analogs and Compounds A, B, C, or D series or methyl 5-<3, - α>6-dihydro-1(2H)-pyridyl >-2-oxo-2H-<1, 2, 4>oxadiazolo 2, 3, -α> pyrimidine-7-carbamate.
6. A composition of Claim 5 wherein the retinoid is selected from the group consisting of stereoisomers of vitamin A acid as well as the aldehydes, alcohols, esters, amides, ethers and salts of said compounds, or a retinoid analog, such as those listed in PCT U.S. 82/01593.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59725284A | 1984-04-06 | 1984-04-06 | |
| US597,252 | 1984-04-06 | ||
| US62475884A | 1984-06-26 | 1984-06-26 | |
| US624,758 | 1984-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1985004577A1 true WO1985004577A1 (en) | 1985-10-24 |
Family
ID=27082777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1985/000556 WO1985004577A1 (en) | 1984-04-06 | 1985-04-02 | Compositions used for hair growth |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0177581A4 (en) |
| WO (1) | WO1985004577A1 (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0187854A1 (en) * | 1984-07-13 | 1986-07-23 | BAZZANO, Gail S | Substituted pyrimidine oxides useful for hair growth promotion |
| WO1988001502A1 (en) * | 1986-09-05 | 1988-03-10 | The Upjohn Company | Sebum-dissolving nonaqueous minoxidil formulation |
| WO1989000996A1 (en) * | 1987-07-31 | 1989-02-09 | L'oreal | New oxadiazolo pyrimidimones, their preparation and their use in cosmetics and dermopharmacy |
| US4832946A (en) * | 1986-12-23 | 1989-05-23 | Green Martin R | Cosmetic composition |
| EP0319027A1 (en) * | 1987-12-04 | 1989-06-07 | L'oreal | Composition to induce and stimulate the hair growth and/or to reduce the hair loss containing a non-ionic surfactant and a pyrimidine derivative |
| WO1989006530A1 (en) * | 1988-01-21 | 1989-07-27 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis | New topical preparation for treatment of alopecia |
| US4871839A (en) * | 1986-03-14 | 1989-10-03 | Lever Brothers Company | Skin treatment composition |
| US4975441A (en) * | 1988-03-23 | 1990-12-04 | Unilever Patent Holdings B.V. | Lactams, their synthesis and use in cosmetic compositions |
| EP0403238A2 (en) * | 1989-06-14 | 1990-12-19 | Unilever Plc | Cosmetic composition |
| US5015470A (en) * | 1986-12-23 | 1991-05-14 | Gibson Walter T | Cosmetic composition |
| US5026691A (en) * | 1987-03-30 | 1991-06-25 | The Upjohn Company | Combination of minoxidil and an antiinflammatory agent for treating patterned alopecia |
| US5037643A (en) * | 1988-03-23 | 1991-08-06 | Unilever Patent Holdings, B.V. | Cosmetic composition |
| EP0459890A1 (en) * | 1990-05-30 | 1991-12-04 | L'oreal | Composition for use in preventing loss of hair and for inducing and stimulating its growth, containing derivatives of 2-alkyl-4-amino(or -2,4-dialkyl)-pyrimidin-3-oxide and the new derivatives of 2-alkyl-4-amino-pyrimidin-3-oxide |
| US5358714A (en) * | 1988-03-23 | 1994-10-25 | Unilever Patent Holdings B.V. | Cosmetic composition |
| AT400516B (en) * | 1987-08-12 | 1996-01-25 | Oreal | AGENT FOR INDUCTION AND STIMULATION OF HAIR GROWTH AND FOR REDUCING HAIR LOSS BASED ON A RETINOID AND A PYRIMID DERIVATIVE |
| US5772990A (en) * | 1991-06-20 | 1998-06-30 | L'oreal | Composition for slowing down the loss of hair based on pyrimidine N-oxides triaminosubstituted or their sulfoconjugated |
| WO1999062484A1 (en) * | 1998-06-03 | 1999-12-09 | Gpi Nil Holdings, Inc. | Small molecule carbamate or urea hair growth compositions and uses |
| US6331537B1 (en) | 1998-06-03 | 2001-12-18 | Gpi Nil Holdings, Inc. | Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds |
| US7078424B2 (en) | 1998-06-03 | 2006-07-18 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4129662A (en) * | 1975-11-03 | 1978-12-12 | Johnson & Johnson | Retinoic acid derivatives for the treatment of acne |
| US4190594A (en) * | 1975-11-03 | 1980-02-26 | Johnson & Johnson | Retinoic acid derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093770B1 (en) * | 1981-11-09 | 1991-06-19 | BAZZANO, Gail S | The use of retinoids and minoxidil (2,4-diamino-6-piperidino-pyrimidine-3-oxide) to increase the rate of growth of human scalp hair and to treat certain types of alopecias |
-
1985
- 1985-04-02 EP EP19850901870 patent/EP0177581A4/en not_active Withdrawn
- 1985-04-02 WO PCT/US1985/000556 patent/WO1985004577A1/en not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4129662A (en) * | 1975-11-03 | 1978-12-12 | Johnson & Johnson | Retinoic acid derivatives for the treatment of acne |
| US4190594A (en) * | 1975-11-03 | 1980-02-26 | Johnson & Johnson | Retinoic acid derivatives |
Non-Patent Citations (2)
| Title |
|---|
| FDA Consumer, February, 1981, Vol. 15, No. 1, see pages 10 and 12 * |
| See also references of EP0177581A4 * |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0187854A4 (en) * | 1984-07-13 | 1987-01-22 | Gail S Bazzano | Substituted pyrimidine oxides useful for hair growth promotion. |
| EP0187854A1 (en) * | 1984-07-13 | 1986-07-23 | BAZZANO, Gail S | Substituted pyrimidine oxides useful for hair growth promotion |
| US4871839A (en) * | 1986-03-14 | 1989-10-03 | Lever Brothers Company | Skin treatment composition |
| WO1988001502A1 (en) * | 1986-09-05 | 1988-03-10 | The Upjohn Company | Sebum-dissolving nonaqueous minoxidil formulation |
| US5015470A (en) * | 1986-12-23 | 1991-05-14 | Gibson Walter T | Cosmetic composition |
| US4832946A (en) * | 1986-12-23 | 1989-05-23 | Green Martin R | Cosmetic composition |
| US5026691A (en) * | 1987-03-30 | 1991-06-25 | The Upjohn Company | Combination of minoxidil and an antiinflammatory agent for treating patterned alopecia |
| WO1989000996A1 (en) * | 1987-07-31 | 1989-02-09 | L'oreal | New oxadiazolo pyrimidimones, their preparation and their use in cosmetics and dermopharmacy |
| EP0303871A1 (en) * | 1987-07-31 | 1989-02-22 | L'oreal | Oxadiazolopyrimidinones, their preparation and their cosmetic and dermopharmaceutical use |
| AT400516B (en) * | 1987-08-12 | 1996-01-25 | Oreal | AGENT FOR INDUCTION AND STIMULATION OF HAIR GROWTH AND FOR REDUCING HAIR LOSS BASED ON A RETINOID AND A PYRIMID DERIVATIVE |
| EP0319027A1 (en) * | 1987-12-04 | 1989-06-07 | L'oreal | Composition to induce and stimulate the hair growth and/or to reduce the hair loss containing a non-ionic surfactant and a pyrimidine derivative |
| WO1989006530A1 (en) * | 1988-01-21 | 1989-07-27 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis | New topical preparation for treatment of alopecia |
| US5358714A (en) * | 1988-03-23 | 1994-10-25 | Unilever Patent Holdings B.V. | Cosmetic composition |
| US4975441A (en) * | 1988-03-23 | 1990-12-04 | Unilever Patent Holdings B.V. | Lactams, their synthesis and use in cosmetic compositions |
| US5037643A (en) * | 1988-03-23 | 1991-08-06 | Unilever Patent Holdings, B.V. | Cosmetic composition |
| EP0403238A2 (en) * | 1989-06-14 | 1990-12-19 | Unilever Plc | Cosmetic composition |
| EP0403238A3 (en) * | 1989-06-14 | 1992-03-04 | Unilever Plc | Cosmetic composition |
| EP0459890A1 (en) * | 1990-05-30 | 1991-12-04 | L'oreal | Composition for use in preventing loss of hair and for inducing and stimulating its growth, containing derivatives of 2-alkyl-4-amino(or -2,4-dialkyl)-pyrimidin-3-oxide and the new derivatives of 2-alkyl-4-amino-pyrimidin-3-oxide |
| US5438058A (en) * | 1990-05-30 | 1995-08-01 | L'oreal | Composition intended to be used for retarding hair loss and for inducing and stimulating hair growth, containing 2-alkyl-4-aminopyrimidine (or 2,4-dialkylpyrimidine) 3-oxide derivatives and new compounds derived from 2-alkyl-4-aminopyrimidine 3-oxide |
| FR2662607A1 (en) * | 1990-05-30 | 1991-12-06 | Oreal | COMPOSITION FOR USE IN BRAKING THE FALL OF HAIR AND IN INDUCING AND STIMULATING THEIR GROWTH, CONTAINING ALKYL-2 AMINO-4 (OR DIALKYL-2-4) PYRIMIDINE OXIDE-3 DERIVATIVES. |
| US5772990A (en) * | 1991-06-20 | 1998-06-30 | L'oreal | Composition for slowing down the loss of hair based on pyrimidine N-oxides triaminosubstituted or their sulfoconjugated |
| WO1999062484A1 (en) * | 1998-06-03 | 1999-12-09 | Gpi Nil Holdings, Inc. | Small molecule carbamate or urea hair growth compositions and uses |
| US6331537B1 (en) | 1998-06-03 | 2001-12-18 | Gpi Nil Holdings, Inc. | Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds |
| AU764032B2 (en) * | 1998-06-03 | 2003-08-07 | Gpi Nil Holdings, Inc. | Small molecule carbamate or urea hair growth compositions and uses |
| US7078424B2 (en) | 1998-06-03 | 2006-07-18 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres |
| US7153883B2 (en) | 1998-06-03 | 2006-12-26 | Gpi Nil Holdings Inc. | Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0177581A4 (en) | 1987-08-10 |
| EP0177581A1 (en) | 1986-04-16 |
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