US4973474A
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2,4-diaminopyrimidine 3-oxide derivatives and their use for the treatment and prevention of hair loss
Assignee: L'Oréal SA
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Filing: 1989-07-31
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Granted: 1990-11-27
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Expires: 2009-07-31
Abstract
Abstract New 2,4-diaminopyrimidine 3-oxide derivatives and their use for the treatment and the prevention of hair loss. The compounds correspond to the formula: <IMAGE> in which: R1 and R2 denote hydrogen or the groups of formula: <IMAGE> with R'3=H or R3, in which R3 denotes alkyl, alkenyl or cycloalkyl; R3 may also denote an aryl or aralkyl radical. R denotes alkyl, alkenyl or cycloalkyl capable of bearing an unsaturation or alkyl bearing an aromatic or heterocyclic nucleus.
Inventors
- 👤 Michel Hocquaux
- 👤 Jacqueline Dumats
- 👤 Quintino Gaetani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 03:51
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/48; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/494; A61K8/4953; A61P; A61P17/00; A61Q; A61Q7/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
196 words
Compound characterized in that it corresponds to the formula: ##STR20## in which: R 1 and R 2 denote, independently of each other, a hydrogen atom, a carbamoyl group of formula: ##STR21## with R' 3 =H or R 3 ; an alkoxycarbonyl group of formula: ##STR22## or an acyl group of formula: ##STR23## in which formulae R 3 denotes a linear or branched C 1 -C 18 alkyl radical, a C 2 -C 18 alkenyl group or a C 5 -C 8 cycloalkyl group; R 3 may also denote an aryl or aralkyl radical corresponding to the formula: ##STR24## in which: n is between 0 and 4l; R 4 and/or R 5 , independently of each other, denote hydrogen, a lower C 1 -C 6 alkyl group, a hydroxyl or alkoxy group or a halogen atom, at least one of the radicals R 1 or R 2 being different from hydrogen; R denotes a linear or branched C 1 -C 18 alkyl or C 2 -C 18 alkenyl radical, a C 4 -C 6 cycloalkyl radical capable of bearing an unsaturation or a C 1 -C 6 alkyl radical bearing a phenyl group or a pyridine ring.
Claim 2
Dependent Claim
196 words
Compound characterized in that it corresponds to the formula: ##STR20## in which: R 1 and R 2 denote, independently of each other, a hydrogen atom, a carbamoyl group of formula: ##STR21## with R' 3 =H or R 3 ; an alkoxycarbonyl group of formula: ##STR22## or an acyl group of formula: ##STR23## in which formulae R 3 denotes a linear or branched C 1 -C 18 alkyl radical, a C 2 -C 18 alkenyl group or a C 5 -C 8 cycloalkyl group; R 3 may also denote an aryl or aralkyl radical corresponding to the formula: ##STR24## in which: n is between 0 and 4l; R 4 and/or R 5 , independently of each other, denote hydrogen, a lower C 1 -C 6 alkyl group, a hydroxyl or alkoxy group or a halogen atom, at least one of the radicals R 1 or R 2 being different from hydrogen; R denotes a linear or branched C 1 -C 18 alkyl or C 2 -C 18 alkenyl radical, a C 4 -C 6 cycloalkyl radical capable of bearing an unsaturation or a C 1 -C 6 alkyl radical bearing a phenyl group or a pyridine ring.
Claim 3
Dependent Claim
30 words
Compound according to claim 1, characterized in that the radical R is chosen from methyl, ethyl, butyl, isobutyl, n-hexyl, n-octyl, n-decyl, lauryl, 2-ethylhexyl, 5-n-hexenyl, 10-undecenyl, cyclohexyl, phenethyl or benzyl groups.
Claim 4
Dependent Claim
19 words
Compound according to claim 1, characterized in that it is 2,4-diamino-6-(n-butyloxy)pyrimidine 3-oxide and its cosmetically or pharmaceutically acceptable salts.
Claim 5
Dependent Claim
19 words
Compound according to claim 1, characterized in that it is 2,4-diamino-6-ethyloxypyrimidine 3-oxide or its cosmetically or pharmaceutically acceptable salts.
Claim 6
Dependent Claim
28 words
Compound according to claim 1, characterized in that it is chosen from 2-amino-4-acetamido-6-butyloxypyrimidine 3-oxide, 2,4-diacetamido-6-butyloxypyrimidine3-oxide, 2,4-di(methoxycarbonylamino)-6-butyloxypyrimidine3-oxide, 2,4-di(benzyloxycarbonylamino)-6-butyloxypyrimidine 3-oxide and N-(2-amino-6-butyloxy-4-pyrimidinyl)-N'-dimethylurea 3-oxide and its cosmetically or pharmaceutically acceptable salts.
Claim 7
Dependent Claim
31 words
Compound of the group of 2,4-diaminopyrimidine 3-oxides, chosen from 2,4-diamino-6-methoxypyrimidine 3-oxide, 2,4-diamino-6-n-hexyloxypyrimidine 3-oxide, 2,4-diamino-6-n-octyloxypyrimidine 3-oxide, 2,4-diamino-6-n-dodecyloxypyrimidine 3-oxide, 2,4-diamino-6-(2-ethylhexyloxy)pyrimidine 3-oxide, 2,4-diamino-6-(5-n-hexenyloxy)pyrimidine 3-oxide, 2,4-diamino-6-(10-undecenyloxy)pyrimidine 3-oxide, 2,4-diamino-6-(2-phenylethyloxy)pyrimidine 3-oxide, or cosmetically or pharmaceutically acceptable salts.
Claim 8
Dependent Claim
31 words
Compound of the group of 2,4-diaminopyrimidine 3-oxides, chosen from 2,4-diamino-6-methoxypyrimidine 3-oxide, 2,4-diamino-6-n-hexyloxypyrimidine 3-oxide, 2,4-diamino-6-n-octyloxypyrimidine 3-oxide, 2,4-diamino-6-n-dodecyloxypyrimidine 3-oxide, 2,4-diamino-6-(2-ethylhexyloxy)pyrimidine 3-oxide, 2,4-diamino-6-(5-n-hexenyloxy)pyrimidine 3-oxide, 2,4-diamino-6-(10-undecenyloxy)pyrimidine 3-oxide, 2,4-diamino-6-(2-phenylethyloxy)pyrimidine 3-oxide, or cosmetically or pharmaceutically acceptable salts.
Claim 9
Dependent Claim
34 words
Composition intended to be employed in topical application, characterized in that it contains, in a physiologically acceptable medium, at least one compound as defined in claim 1, in an effective amount for topical application.
Claim 10
Dependent Claim
81 words
The compositions intended to be employed in therapeutic treatment of hair loss according to claim 7, characterized in that it is in the form of an ointment tincture, cream, pomade, powder, patch, impregnated pad, solution, emulsion, vesicular emulsion, lotion, gel, spray or anhydrous or aqueous, suspension, and that it contains in a pharmaceutically acceptable medium, at least one compound as defined in claim 1, in concentrations of between 0.1 and 10% by weight relative to the total weight of the composition.
Claim 11
Dependent Claim
59 words
Composition intended to be employed in cosmetics, such as defined in claim 7, characterized in that it is in the form of a lotion, gel, soap, shampoo, aerosol or foam and that it contains, in a cosmetically acceptable carrier, at least one compound such as defined in claim 1, in a concentration of between 0.01 and 7.5% by weight.
Claim 12
Dependent Claim
17 words
Composition according to claim 7, characterized in that, in addition to hydrating agents, it contains antiseborrhoeic agents.
Claim 13
Dependent Claim
105 words
Composition according to claim 7, characterized in that it also contains agents which further improve the activity of the compounds of formula (I) relating to the fresh growth and delaying the loss of hair, the said agents are selected from the group consisting of nicotinic acid esters, steroid or nonsteroid antiinflammatory agents, retinoids, antibacterial agents, calcium antagonist agents, hormones, antiandrogen agents or scavengers for OH radicals, diazoxide, spiroxazone, phospholipids, linolenic and linoleic acids, salicylic acid and its derivative, hydroxycarboxylic or ketocarboxylic acids, their esters, lactones and their corresponding salts, anthralin or 1,8,9-trihydroxyanthracene, carotenoids, 5,8,11,14-eicosatetraynoic and 5,8,11-eicosatriynoic acids and their esters and amides, and mixtures thereof.
Claim 14
Dependent Claim
41 words
Composition according to claim 7, characterized in that the physiologically acceptable medium consists of water, a mixture of water and of one or more organic solvent(s) or of a mixture of organic solvents, the organic solvents being pharmaceutically or cosmetically acceptable.
Claim 15
Dependent Claim
28 words
Composition according to claim 12, characterized in that the solvents are chosen from lower C 1 -C 4 alcohols, alkylene glycols and mono- and dialkylene glycol alkyl ethers.
Claim 16
Dependent Claim
37 words
Composition according to claim 7, characterized in that the physiologically acceptable medium is thickened by means of thickening or gelling agents and contains preservatives, stabilizers, pH regulators, osmotic pressure modifiers, emulsifiers, UVA and UVB filters and antioxidants.
Claim 17
Dependent Claim
20 words
Composition according to claim 14, characterized in that it also contains surface-active agents chosen from nonionic and amphoteric surface-active agents.
Claim 18
Dependent Claim
23 words
Process for cosmetic treatment of hair or of the scalp, characterized in that the composition such as defined in claim 9 is applied.
Claim 19
Dependent Claim
31 words
Method of use of a composition according to claim 7 in the therapeutic treatment of hair loss comprising applying an effective amount of said composition to the hair or the scalp.
Claim 20
Dependent Claim
30 words
Composition according to claim 8 in which the concentration of the compound of claim 1 is between 0.2 and 5% by weight relative to the total weight of the composition.
References Cited (Backward Citations)
WO1986000616A1
Cited
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