US5373006A — Combination of derivatives of 1,8-hydroxy and/or …

Claim 1

Independent Claim 224 words

A composition comprising a combination intended to induce and to stimulate hair growth and to reduce its loss, comprising: (a) an effective amount of a component (A) containing at least one derivative of 1,8-dihydroxy-, 1,8-diacyloxy- or 1-hydroxy-8-acyloxyanthracene or anthrone, in a physiologically acceptable medium, (b) an effective amount of a component (B) containing, in a physiologically acceptable medium, at least one pyrimidine derivative corresponding to the formula: ##STR21## in which R 1 denotes a group ##STR22## in which R 30 and R 31 may, independently of each other, denote hydrogen or an alkyl, alkenyl, alkylaryl or cycloalkyl group; R 30 and R 31 can also conjointly, with the nitrogen atom to which they are bonded form a heterocyclic ring selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidyl, hexahydroazepinyl, heptamethyleneimine, octamethyleneimine, morpholinyl, and 4-(lower)alkylpiperazdinyl groups, it being possible for the heterocyclic groups to be substituted on the carbon atoms by 1 to 3 lower alkyl, hydroxyl or alkoxy groups; the group R 29 denoting a hydrogen atom or an alkyl, alkenyl, alkylalkoxy, cycloalkyl, aryl, alkylaryl, arylalkyl, alkylarylalkyl, alkoxyarylalkyl or haloarylalkyl group, as well as the salts of addition to physiologically acceptable acids, the components (A) and (B) being present in a sole composition or being intended for separate applications, either simultaneous or successive or spaced in time, to hair and to the scalp.

Claim 2

Dependent Claim 224 words

A composition comprising a combination intended to induce and to stimulate hair growth and to reduce its loss, comprising: (a) an effective amount of a component (A) containing at least one derivative of 1,8-dihydroxy-, 1,8-diacyloxy- or 1-hydroxy-8-acyloxyanthracene or anthrone, in a physiologically acceptable medium, (b) an effective amount of a component (B) containing, in a physiologically acceptable medium, at least one pyrimidine derivative corresponding to the formula: ##STR21## in which R 1 denotes a group ##STR22## in which R 30 and R 31 may, independently of each other, denote hydrogen or an alkyl, alkenyl, alkylaryl or cycloalkyl group; R 30 and R 31 can also conjointly, with the nitrogen atom to which they are bonded form a heterocyclic ring selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidyl, hexahydroazepinyl, heptamethyleneimine, octamethyleneimine, morpholinyl, and 4-(lower)alkylpiperazdinyl groups, it being possible for the heterocyclic groups to be substituted on the carbon atoms by 1 to 3 lower alkyl, hydroxyl or alkoxy groups; the group R 29 denoting a hydrogen atom or an alkyl, alkenyl, alkylalkoxy, cycloalkyl, aryl, alkylaryl, arylalkyl, alkylarylalkyl, alkoxyarylalkyl or haloarylalkyl group, as well as the salts of addition to physiologically acceptable acids, the components (A) and (B) being present in a sole composition or being intended for separate applications, either simultaneous or successive or spaced in time, to hair and to the scalp.

Claim 3

Dependent Claim 280 words

The composition according to claim 1, wherein the derivative of 1,8-hydroxy and/or acyloxy anthracene or anthrone is selected from the group consisting of: --1,8,9-trihydroxyanthracene or 1,8-dihydroxy-9-anthrone and its dimer, --1,8,1',8'-tetrahydroxydianthrone, --1,8-dihydroxy-9-anthrones substituted in position 10 by groups of formulae: ##STR23## in which R 2 denotes a hydrogen atom, a linear or branched alkyl radical containing from 1 to 8 carbon atoms, a linear or branched mono- or polyhydroxyalkyl radical containing from 1 to 3 carbon atoms, a carbamoyl radical or a phenyl radical, Y and Z denote simultaneously a --CONR 3 R 4 group or else denote, independently of each other, either a --CONR 3 R 4 group or else a CO 2 R 5 group, with R 3 , R 4 and R 5 denoting a hydrogen atom, an alkyl radical containing from 1 to 8 carbon atoms, a mono- or polyhydroxyalkyl radical, optionally interrupted by an oxygen atom, containing from 3 to 8 carbon atoms, a cycloalkyl radical containing from 3 to 6 carbon atoms, or else R 3 and R 4 taken together form a divalent radical selected from the group consisting of --(CH 2 ) n -- where n is equal to 4 or 5 --(CH 2 ) 2 --O--(CH 2 ) 2 --, ##STR24## wherein R 9 denotes a hydrogen atom or a methyl or 2-hydroxyethyl radical, R 6 denotes a CO 2 R 5 , CN, CHO or CONH 2 group or else CONH--CH 2 OH, in which R 5 has the same meaning as that indicated above, and R 7 and R 8 denote, independently of each other, a hydrogen atom or a methyl radical, as well as their salts and optical isomers,

Claim 4

Dependent Claim 145 words

--1. 8-dihydroxy-9-anthrone adducts comprising the following divalent radicals in positions 9 and 10: ##STR25## in which R 10 , R 11 and R' 11 denote a hydrogen atom, a linear or branched lower alkyl radical containing from 1 to 8 carbon atoms, a monohydroxy alkyl radical optionally interrupted by one or more oxygen atoms, containing from 2 to 8 carbon atoms, a cycloalkyl radical containing from 4 to 6 carbon atoms, a phenyl radical or a benzyl radical, R 12 and R' 12 , which are identical or different, denote a hydrogen atom, a linear or branched lower alkyl radical containing from 1 to 8 carbon atoms except for R 12 =R' 12 =CH 3 , a monohydroxyalkyl radical, optionally interrupted by one or more oxygen atoms, containing from 2 to 8 carbon atoms, a phenyl or benzyl radical and the salts of these compounds:

Claim 5

Dependent Claim 145 words

--1. 8-dihydroxy-9-anthrone adducts comprising the following divalent radicals in positions 9 and 10: ##STR25## in which R 10 , R 11 and R' 11 denote a hydrogen atom, a linear or branched lower alkyl radical containing from 1 to 8 carbon atoms, a monohydroxy alkyl radical optionally interrupted by one or more oxygen atoms, containing from 2 to 8 carbon atoms, a cycloalkyl radical containing from 4 to 6 carbon atoms, a phenyl radical or a benzyl radical, R 12 and R' 12 , which are identical or different, denote a hydrogen atom, a linear or branched lower alkyl radical containing from 1 to 8 carbon atoms except for R 12 =R' 12 =CH 3 , a monohydroxyalkyl radical, optionally interrupted by one or more oxygen atoms, containing from 2 to 8 carbon atoms, a phenyl or benzyl radical and the salts of these compounds:

Claim 6

Dependent Claim 243 words

--1. 8-dihydroxy-9-anthrones substituted in position 10 by the groups: ##STR26## in which R 13 and R' 13 , which are identical or different, denote a hydrogen atom or a methyl or ethyl radical, or their isomers, or by the group of formula: ##STR27## in which R 14 denotes a hydrogen atom or the radical COR' 15 , with R 15 and R' 15 , which are identical or different, denoting a hydrogen atom, a linear or branched alkyl radical containing from 1 to 6 carbon atoms, a cycloalkyl radical containing from 4 to 6 carbon atoms or a benzyl radical, or else R 14 and R 15 , taken together, form a radical ##STR28## and n is equal to 0 or 1, as well as their isomers. --the 10-aryl-1,8-dihydroxy anthrones in which the aryl group corresponds to the following formula: ##STR29## in which R 16 , R 17 , R 18 , R 19 and R 20 which are identical or different, denote a hydrogen atom, a halogen atom, the CF 3 radical, a hydroxyl group, a lower alkyl or cycloalkyl radical, a lower hydroxyalkyl radical, a lower alkoxy radical, a nitrile group, a radical ##STR30## r' and r", which are identical or different, denote a hydrogen atom or a lower alkyl radical, n is 0 or an integer from 1 to 3 inclusive, and R' and R" denote a hydrogen atom, a linear or branched lower alkyl radical or an aryl radical,

Claim 7

Dependent Claim 243 words

--1. 8-dihydroxy-9-anthrones substituted in position 10 by the groups: ##STR26## in which R 13 and R' 13 , which are identical or different, denote a hydrogen atom or a methyl or ethyl radical, or their isomers, or by the group of formula: ##STR27## in which R 14 denotes a hydrogen atom or the radical COR' 15 , with R 15 and R' 15 , which are identical or different, denoting a hydrogen atom, a linear or branched alkyl radical containing from 1 to 6 carbon atoms, a cycloalkyl radical containing from 4 to 6 carbon atoms or a benzyl radical, or else R 14 and R 15 , taken together, form a radical ##STR28## and n is equal to 0 or 1, as well as their isomers. --the 10-aryl-1,8-dihydroxy anthrones in which the aryl group corresponds to the following formula: ##STR29## in which R 16 , R 17 , R 18 , R 19 and R 20 which are identical or different, denote a hydrogen atom, a halogen atom, the CF 3 radical, a hydroxyl group, a lower alkyl or cycloalkyl radical, a lower hydroxyalkyl radical, a lower alkoxy radical, a nitrile group, a radical ##STR30## r' and r", which are identical or different, denote a hydrogen atom or a lower alkyl radical, n is 0 or an integer from 1 to 3 inclusive, and R' and R" denote a hydrogen atom, a linear or branched lower alkyl radical or an aryl radical,

Claim 8

Dependent Claim 277 words

--1. 8-diacyloxy-10-acylanthrones of general formula: ##STR31## in which: R 21 and R 22 , which are identical or different, denote a linear or branched alkyl radical containing from 1 to 15 carbon atoms, a cycloalkyl radical with 3 to 6 carbon atoms, a 2- or 3-furyl radical, a 3- or 4-pyridyl radical, a 2-thienyl radical or an aromatic radical of formula: ##STR32## in which X, Y and Z, which are identical or different, denote a hydrogen atom, a lower alkyl radical, a trifluoromethyl radical, a lower alkoxy radical, a halogen atom or a nitro or hydroxyl group; --10-acetyl-1,8,9-triacetoxyanthracene of formula: ##STR33## --1-hydroxy-8-acyloxy-10-acyl anthrones of general formula: ##STR34## in which: R 23 denotes a hydrogen atom or a linear lower alkyl radical; R 24 denotes a hydrogen atom, a linear or branched alkyl radical containing from 1 to 17 carbon atoms, a linear or branched alkenyl radical containing from 2 to 17 carbon atoms, or R 23 and R 24 taken together form, together with the carbon atom to which they are attached, a cycloalkyl radical containing from 3 to 6 carbon atoms; R 25 denotes a linear or branched alkyl radical containing from 1 to 18 carbon atoms, a linear or branched alkenyl radical containing from 2 to 18 carbon atoms, a cycloalkyl radical containing from 3 to 6 carbon atoms, a 2- or 3-furyl radical, a 3- or 4-pyridyl radical, a 2-thienyl radical or an aromatic radical of formula: ##STR35## in which X, Y and Z, which are identical or different denote a hydrogen atom, a lower alkyl radical, a trifluoromethyl radical, a lower alkoxy radical, a halogen atom, a nitro group or a hydroxyl group;

Claim 9

Dependent Claim 277 words

--1. 8-diacyloxy-10-acylanthrones of general formula: ##STR31## in which: R 21 and R 22 , which are identical or different, denote a linear or branched alkyl radical containing from 1 to 15 carbon atoms, a cycloalkyl radical with 3 to 6 carbon atoms, a 2- or 3-furyl radical, a 3- or 4-pyridyl radical, a 2-thienyl radical or an aromatic radical of formula: ##STR32## in which X, Y and Z, which are identical or different, denote a hydrogen atom, a lower alkyl radical, a trifluoromethyl radical, a lower alkoxy radical, a halogen atom or a nitro or hydroxyl group; --10-acetyl-1,8,9-triacetoxyanthracene of formula: ##STR33## --1-hydroxy-8-acyloxy-10-acyl anthrones of general formula: ##STR34## in which: R 23 denotes a hydrogen atom or a linear lower alkyl radical; R 24 denotes a hydrogen atom, a linear or branched alkyl radical containing from 1 to 17 carbon atoms, a linear or branched alkenyl radical containing from 2 to 17 carbon atoms, or R 23 and R 24 taken together form, together with the carbon atom to which they are attached, a cycloalkyl radical containing from 3 to 6 carbon atoms; R 25 denotes a linear or branched alkyl radical containing from 1 to 18 carbon atoms, a linear or branched alkenyl radical containing from 2 to 18 carbon atoms, a cycloalkyl radical containing from 3 to 6 carbon atoms, a 2- or 3-furyl radical, a 3- or 4-pyridyl radical, a 2-thienyl radical or an aromatic radical of formula: ##STR35## in which X, Y and Z, which are identical or different denote a hydrogen atom, a lower alkyl radical, a trifluoromethyl radical, a lower alkoxy radical, a halogen atom, a nitro group or a hydroxyl group;

Claim 10

Dependent Claim 113 words

--1. 8,9-triacetoxyanthracene of formula: ##STR36## --mono-, di- and triesters of 1,8-dihydroxy-10-phenyl-9-anthrone or 9-anthranol of the following general formula: ##STR37## in which: p is 0 or 1; when p=0, t=1 and R 27 denotes a hydrogen atom or --COR 3 ; when p=1, t=0 and R 26 and R 27 denote, independently of each other, a hydrogen atom or --COR 28 ; R 28 denoting a linear or branched alkyl radical containing from 1 to 17 carbon atoms, a cycloalkyl radical, or a phenyl radical optionally substituted by a lower alkyl, a lower alkoxy, a halogen atom, a nitro group, a --CF 3 radical or by a hydroxyl group, and mixtures of said esters.

Claim 11

Dependent Claim 113 words

--1. 8,9-triacetoxyanthracene of formula: ##STR36## --mono-, di- and triesters of 1,8-dihydroxy-10-phenyl-9-anthrone or 9-anthranol of the following general formula: ##STR37## in which: p is 0 or 1; when p=0, t=1 and R 27 denotes a hydrogen atom or --COR 3 ; when p=1, t=0 and R 26 and R 27 denote, independently of each other, a hydrogen atom or --COR 28 ; R 28 denoting a linear or branched alkyl radical containing from 1 to 17 carbon atoms, a cycloalkyl radical, or a phenyl radical optionally substituted by a lower alkyl, a lower alkoxy, a halogen atom, a nitro group, a --CF 3 radical or by a hydroxyl group, and mixtures of said esters.

Claim 12

Dependent Claim 40 words

The composition according to claim 1, wherein the pyrimidine derivative is a component of formula (I) in which R 29 denotes hydrogen and R 1 denotes a group ##STR38## in which R 30 and R 31 form a piperidyl ring.

Claim 13

Dependent Claim 17 words

The composition according to claim 1, wherein the compound of formula (I) consists of 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine or minoxidil.

Claim 14

Dependent Claim 23 words

The composition according to claim 1, wherein the derivative of 1,8-hydroxy and/or acyloxy anthracene or anthrone consists of 1,8,9-trihydroxyanthracene or 1,8-dihydroxy-9-anthrone or anthralin.

Claim 15

Dependent Claim 42 words

The composition according to claim 1, wherein the component (A) contains the derivative of 1,8-hydroxy and/or acyloxy anthracene or anthrone in proportions of between 0.01 and 10% by weight relative to the weight of component (A), and preferably between 0.1 and 1%.

Claim 16

Dependent Claim 33 words

The composition according to claim 1, wherein the component (B) contains the compound of formula (I) in proportions of between 0.05 and 10% by weight relative to the total weight of the composition.

Claim 17

Dependent Claim 30 words

The composition according to claim 1, wherein the weight ratio of the pyrimidine derivative of formula (I) to the 1,8-hydroxy and/or acyloxy anthracene or anthrone is between 2/1 and 10/1.

Claim 18

Dependent Claim 75 words

The composition according to claim 1, under the form of a single composition containing the components (A) and (B) in which the derivative of 1,8-hydroxy and/or acyloxy anthracene or anthrone is present in proportions between 0.01 and 5% by weight relative to the total weight of the composition and that the pyrimidine derivative of formula (I) is present in proportions of between 0.05 and 6% by weight relative to the total weight of the composition.

Claim 19

Dependent Claim 50 words

The composition according to claim 1, wherein the physiologically acceptable media consist of one or more anhydrous solvents or a mixture of water and of one or more solvent(s), the solvents are selected from the group consisting of lower alcohols, alkylene glycols or alkylene glycol and dialkylene glycol alkyl ethers.

Claim 20

Dependent Claim 24 words

The composition according to claim 1, wherein at least one of the physiologically acceptable media is thickened by means of thickening and/or gelling agents.

Claim 21

Dependent Claim 61 words

Combination according to claim 1, wherein at least one of the components (A) and (B) also contains a cosmetically or pharmaceutically acceptable adjuvant selected from the group consisting of preserving agents, complexing agents, colorants, alkalizing agents, acidifying agents, anionic surface-active agents, cationic surface-active agents, nonionic surface-active agents, amphoteric surface-active agents, anionic polymers, cationic polymers, nonionic polymers, amphoteric polymers and mixtures thereof.

Claim 22

Dependent Claim 34 words

Process for cosmetic treatment of hair or of the scalp, wherein the components (A) and (B) of the combination defined in claim 1 are applied separately, either simultaneously or successively or spaced in time.

Claim 23

Dependent Claim 57 words

Device with a number of compartments or a kit, comprising in a first compartment, a component (A) containing a derivative of 1,8-hydroxy and/or acyloxy anthracene or anthrone defined in claim 1, in a physiologically acceptable medium, and a second compartment containing a component (B) containing a pyrimidine derivative corresponding to formula (I), in a physiologically acceptable medium.

Claim 24

Dependent Claim 57 words

The composition comprising a pharmaceutically effective combination for the treatment of hair loss, comprising an effective amount of each the components of the combination of claim 1, wherein said effective amount is effective in inducing and stimulating hair growth and reducing its loss when each of said components is applied to the scalp successively, intermittently, or simultaneously.

Claim 25

Dependent Claim 29 words

A method for inducing and stimulating hair growth and reducing its loss comprising applying the pharmaceutical combination of claim 15 to the scalp of an individual afflicted with alopecia.

Claim 26

Dependent Claim 74 words

A composition comprising a combination intended to induce and to stimulate hair growth and to reduce its loss, comprising: (a) an effective amount of a component (A) containing anthralin, in a physiologically acceptable medium, and (b) an effective amount of a component (B) containing in a physiologically acceptable medium, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine or minoxidil, components (A) and (B) being intended for separate applications, either simultaneous or successive or spaced in time, to hair and to scalp.

Claim 27

Dependent Claim 74 words

A composition comprising a combination intended to induce and to stimulate hair growth and to reduce its loss, comprising: (a) an effective amount of a component (A) containing anthralin, in a physiologically acceptable medium, and (b) an effective amount of a component (B) containing in a physiologically acceptable medium, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine or minoxidil, components (A) and (B) being intended for separate applications, either simultaneous or successive or spaced in time, to hair and to scalp.

Claim 28

Dependent Claim 29 words

The composition according to claim 17, wherein the component (A) contains anthralin in the proportion of between 0.01 and 10% by weight relative to the weight of component (A).

Claim 29

Dependent Claim 29 words

The composition according to claim 17, wherein the component (A) contains anthralin in the proportion of between 0.1 and 1% by weight relative to the weight of component (A).

Claim 30

Dependent Claim 30 words

The composition according to claim 17, wherein the component (B) contains minoxidil in the proportion of between 0.05 and 10% by weight relative to the total weight of the composition.

Claim 31

Dependent Claim 19 words

The composition according to claim 17, wherein the weight ratio of minoxidil to anthralin is between 2/1 and 10/1.

Claim 32

Dependent Claim 32 words

Process for cosmetic treatment of hair or scalp, wherein the components (A) and (B) of the combination defined in claim 17 are applied separately, either simultaneously or successively or spaced in time.

Claim 33

Dependent Claim 41 words

Device with a number of compartments or a kit, comprising in a first compartment a component (A) containing anthralin in a physiologically acceptable medium, and in a second compartment, a component (B) containing 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyridimide or minoxidil in a physiologically acceptable medium.

Claim 34

Dependent Claim 41 words

Device with a number of compartments or a kit, comprising in a first compartment a component (A) containing anthralin in a physiologically acceptable medium, and in a second compartment, a component (B) containing 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyridimide or minoxidil in a physiologically acceptable medium.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1997-12-12	1998-06-13	1998-12-13	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2001-12-12	2002-06-13	2002-12-13	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2005-12-12	2006-06-13	2006-12-13	$7700.00	Window Closed / Lapsed

Combination of derivatives of 1,8-hydroxy and/or acyloxy anthracene or anthrone and of pyrimidine derivatives for inducing and stimulating hair growth and reducing loss thereof

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