CH672423A5 - - Google Patents
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- CH672423A5 CH672423A5 CH4508/87A CH450887A CH672423A5 CH 672423 A5 CH672423 A5 CH 672423A5 CH 4508/87 A CH4508/87 A CH 4508/87A CH 450887 A CH450887 A CH 450887A CH 672423 A5 CH672423 A5 CH 672423A5
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- Switzerland
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- composition according
- hair
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- 239000000203 mixture Substances 0.000 claims description 49
- 210000004209 hair Anatomy 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 19
- 201000004384 Alopecia Diseases 0.000 claims description 18
- 230000003779 hair growth Effects 0.000 claims description 15
- 230000003676 hair loss Effects 0.000 claims description 15
- 208000024963 hair loss Diseases 0.000 claims description 14
- 239000002562 thickening agent Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 210000004761 scalp Anatomy 0.000 claims description 7
- 230000004936 stimulating effect Effects 0.000 claims description 7
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 150000004492 retinoid derivatives Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 230000003659 hair regrowth Effects 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 125000005238 alkylenediamino group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003349 gelling agent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 229920006317 cationic polymer Polymers 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 229960005280 isotretinoin Drugs 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229930002330 retinoic acid Natural products 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229960003632 minoxidil Drugs 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 229960001727 tretinoin Drugs 0.000 claims description 2
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 230000003698 anagen phase Effects 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 5
- 230000003797 telogen phase Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 4
- 230000031774 hair cycle Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- -1 alkylene glycols Chemical class 0.000 description 3
- 231100000360 alopecia Toxicity 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 230000003778 catagen phase Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000003803 hair density Effects 0.000 description 2
- 230000003681 hair reduction Effects 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920002305 Schizophyllan Polymers 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 239000002610 basifying agent Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000007321 biological mechanism Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical class C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- SHGAZHPCJJPHSC-XFYACQKRSA-N isotretinoin Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-XFYACQKRSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- DGXNWWJYEMQHED-UHFFFAOYSA-N trimethyl-(4-methyl-3-oxopent-4-enyl)azanium Chemical class CC(=C)C(=O)CC[N+](C)(C)C DGXNWWJYEMQHED-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
Description
L'invention est relative à de nouvelles compositions pour induire et stimuler la croissance des cheveux et diminuer la chute à base de dérivés d'alkylène diamino quinazoline. The invention relates to new compositions for inducing and stimulating hair growth and reducing hair loss based on alkylene diamino quinazoline derivatives.
50 L'homme a un capital de 100 000 à 150 000 cheveux et il est normal de perdre quotidiennement 50 à 100 cheveux. La maintenance de ce capital résulte essentiellement du fait que la vie d'un cheveu est soumise à un cycle dit cycle pilaire au cours duquel le cheveu se forme, croît et tombe avant d'être remplacé par un nouvel 55 élément qui apparaît dans le même follicule. 50 The man has a capital of 100,000 to 150,000 hairs and it is normal to lose 50 to 100 hairs daily. The maintenance of this capital results essentially from the fact that the life of a hair is subjected to a cycle known as the hair cycle during which the hair is formed, grows and falls before being replaced by a new 55 element which appears in the same follicle.
On observe au cours d'un cycle pilaire successivement trois phases: à savoir la phase anagène, la phase catagène et la phase télo-gène. Three phases are observed successively during a hair cycle: namely the anagen phase, the catagen phase and the telogen phase.
Au cours de la première phase dite anagène, le cheveu passe par 60 une période de croissance active associée avec une intense activité métabolique au niveau du bulbe. During the first so-called anagen phase, the hair goes through an active growth period associated with intense metabolic activity at the level of the bulb.
La deuxième phase dite catagène est transitoire et elle est marquée par un ralentissement des activités mitotiques. Au cours de cette phase, le cheveu subit une involution, le follicule s'atrophie et 65 son implantation dermique apparaît de plus en plus haute. The second phase, called catagen, is transient and is marked by a slowdown in mitotic activities. During this phase, the hair undergoes an involution, the follicle atrophies and its dermal implantation appears higher and higher.
La phase terminale dite télogène correspond à une période de repos du follicule et le cheveu finit par tomber, poussé par un cheveu anagène naissant. The so-called telogen terminal phase corresponds to a period of rest of the follicle and the hair ends up falling, pushed by an incipient anagen hair.
672 423 672,423
Ce processus de renouvellement physique permanent subit une évolution naturelle au cours du vieillissement, les cheveux deviennent plus fins et leurs cycles plus courts. This permanent physical renewal process undergoes a natural evolution during aging, the hair becomes thinner and their cycles shorter.
L'alopécie survient lorsque ce processus de renouvellement physique est accéléré ou perturbé, c'est-à-dire que les phases de croissance sont raccourcies, le passage des cheveux en phase télogène est plus précoce et les cheveux tombent en plus grand nombre; les cycles de croissance successifs aboutissent à des cheveux de plus en plus fins et.de plus en plus courts, se transforment peu à peu en un duvet non pigmenté. Ce phénomène peut conduire à la calvitie. Alopecia occurs when this process of physical renewal is accelerated or disturbed, that is to say that the growth phases are shortened, the passage of the hair into the telogen phase is earlier and the hair falls in greater numbers; successive growth cycles result in increasingly fine and shorter hair, gradually transforming into a non-pigmented down. This phenomenon can lead to baldness.
Le cycle pilaire est tributaire de nombreux facteurs pouvant entraîner une alopécie plus ou moins prononcée. Parmi ces facteurs, on peut citer les facteurs alimentaires, endocriniens, nerveux, etc. Les variations des différentes catégories de cheveux peuvent être déterminées grâce au trichogramme. The hair cycle is dependent on many factors that can lead to more or less pronounced alopecia. Among these factors, we can cite food, endocrine, nervous factors, etc. The variations of the different hair categories can be determined using the trichogram.
On recherche depuis de nombreuses années dans l'industrie cosmétique ou pharmaceutique des compositions permettant de supprimer ou de réduire l'effet de l'alopécie et notamment d'induire ou de stimuler la croissance des cheveux. We have been looking for many years in the cosmetic or pharmaceutical industry for compositions which make it possible to suppress or reduce the effect of alopecia and in particular to induce or stimulate hair growth.
Dans cette optique, on a déjà proposé des composés tels que l'amino-6 dihydro-1,2 hydroxy-1 imino-2 pipéridino-4 pyrimidine et ses dérivés. De tels composés sont décrits notamment dans le brevet US-A-4 139 619. With this in mind, compounds have already been proposed such as 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidino-pyrimidine and its derivatives. Such compounds are described in particular in US-A-4,139,619.
On a également proposé dans le brevet WO-A-83 02 558 d'associer des rétinoïdes aux composés susnommés. It has also been proposed in patent WO-A-83 02 558 to associate retinoids with the above-mentioned compounds.
La titulaire a découvert que certains dérivés d'alkylène diamino quinazoline pouvaient, de façon surprenante, induire et stimuler la croissance des cheveux et diminuer leur chute. The licensee discovered that certain alkylene diamino quinazoline derivatives could, surprisingly, induce and stimulate hair growth and reduce hair loss.
Ces composés sont connus en eux-mêmes et ont été décrits en particulier dans les demandes de certificat d'addition français Nos 2 466 462 et 2 468 595, These compounds are known in themselves and have been described in particular in the applications for French certificate of addition Nos 2 466 462 and 2 468 595,
Ces composés sont en particulier connus pour leurs propriétés thérapeutiques, notamment dans le domaine cardiovasculaire comme antihypertenseurs. These compounds are in particular known for their therapeutic properties, in particular in the cardiovascular field as antihypertensives.
La titulaire a constaté que ces composés, utilisés en application topique, avaient une activité sur la repousse des cheveux et permettaient d'induire ou stimuler la croissance de ceux-ci sans diminuer leur chute. The licensee noted that these compounds, used in topical application, had an activity on hair regrowth and made it possible to induce or stimulate their growth without reducing their fall.
Un objet de l'invention est donc constitué par une composition pour induire et stimuler la croissance des cheveux et diminuer leur chute à base de dérivés d'alkylène diamino quinazoline. An object of the invention therefore consists of a composition for inducing and stimulating hair growth and reducing hair loss based on alkylene diamino quinazoline derivatives.
Un autre objet de l'invention est constitué par l'utilisation de ces composés dans la préparation d'une composition à effet thérapeutique au niveau de l'induction et de la stimulation de la croissance des cheveux. Another object of the invention is constituted by the use of these compounds in the preparation of a composition with a therapeutic effect at the level of the induction and the stimulation of hair growth.
D'autres objets de l'invention apparaîtront à la lecture de la description et des exemples qui suivent. Other objects of the invention will appear on reading the description and the examples which follow.
La composition conforme à l'invention est essentiellement caractérisée par le fait qu'elle contient dans un milieu physiologiquement acceptable au moins un composé répondant à la formule: The composition in accordance with the invention is essentially characterized in that it contains, in a physiologically acceptable medium, at least one compound corresponding to the formula:
CH3O CH3O
CH3O CH3O
%s^,|-CnH2n-N-COR- % s ^, | -CnH2n-N-COR-
K2 K2
Ri Ri
(I) (I)
dans laquelle: in which:
Ri et R2 représentent, indépendamment l'un de l'autre, un atome d'hydrogène, un groupement alkyle ayant 1 à 4 atomes de carbone ou un groupement benzyle, R 1 and R 2 represent, independently of one another, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a benzyl group,
n est un nombre entier égal à 2, 3 ou 4, n is an integer equal to 2, 3 or 4,
R représente un groupement cycloalkyle en C3-C6, un groupement de formule: R represents a C3-C6 cycloalkyl group, a group of formula:
J J
(CH2)< (CH2) <
un groupement de formules: a grouping of formulas:
ï-'X ï-'X
ou ou bien un groupement de formule: or or a group of formula:
(CH2)r (CH2) r
(V) (V)
où m = 0,1,2 P = 0, 1,2 where m = 0.1.2 P = 0, 1.2
(II) (II)
où q = 0, 1, 2 where q = 0, 1, 2
ainsi que leurs sels d'addition avec des acides pharmaceutiquement ou cosmétiquement acceptables. as well as their addition salts with pharmaceutically or cosmetically acceptable acids.
Les composés particulièrement préférés, utilisables conformément à l'invention, sont ceux répondant à la formule (I) dans la-20 quelle n est égal à 3, R! représente un atome d'hydrogène ou un groupement méthyle, R2 représente un groupement méthyle ou benzyle, R représente un groupement tétrahydrofuryle, cyclopentyle, cyclopropyle, dihydrobenzofuryle ou benzofuryle. The particularly preferred compounds which can be used in accordance with the invention are those corresponding to formula (I) in which n is equal to 3, R! represents a hydrogen atom or a methyl group, R2 represents a methyl or benzyl group, R represents a tetrahydrofuryl, cyclopentyl, cyclopropyl, dihydrobenzofuryl or benzofuryl group.
Le composé particulièrement préféré est constitué par un 25 composé de formule (I) dans laquelle n est égal à 3, R2 représente un groupement méthyle, Rj représente l'hydrogène et R le groupement tétrahydrofuryle. The particularly preferred compound consists of a compound of formula (I) in which n is equal to 3, R2 represents a methyl group, Rj represents hydrogen and R represents the tetrahydrofuryl group.
Les compositions topiques conformes à l'invention contiennent le composé de formule (I) dans des proportions comprises entre 0,01 30 et 10% en poids par rapport au poids total de la composition, et de préférence entre 0,1 et 5% en poids. The topical compositions in accordance with the invention contain the compound of formula (I) in proportions of between 0.01 and 10% by weight relative to the total weight of the composition, and preferably between 0.1 and 5% by weight. weight.
Une composition particulièrement préférée est celle renfermant le Nt-Camino-^ diméthoxy-6,7 quinazolyl-2) Nt-méthyl N2(tétrahy-drofuroyl-2)propylène diamine, monochlorhydrate, dans des pro-35 portions comprises entre 0,1 et 5% en poids par rapport au poids total de la composition. A particularly preferred composition is that containing Nt-Camino-^ dimethoxy-6,7 quinazolyl-2) Nt-methyl N2 (tetrahy-drofuroyl-2) propylene diamine, monohydrochloride, in pro-35 portions of between 0.1 and 5% by weight relative to the total weight of the composition.
Selon une forme de réalisation avantageuse de l'invention, le composé de formule (I) peut être associé à un dérivé de pyrimidine ayant un effet sur la repousse des cheveux et plus particulièrement 40 l'amino-6 dihydro-1,2 hydroxy-1 imino-2 pipéridino-4 pyrimidine encore connu sous le nom de «Minoxidil», ou bien un rétinoïde tel que ceux décrits dans la demande WO-82 02 833 ou une association des deux. According to an advantageous embodiment of the invention, the compound of formula (I) can be combined with a pyrimidine derivative having an effect on hair regrowth and more particularly 40 amino-6 dihydro-1,2 hydroxy- 1 imino-2 piperidino-4 pyrimidine still known under the name of "Minoxidil", or a retinoid such as those described in the application WO-82 02 833 or a combination of the two.
Parmi les rétinoïdes particulièrement préférés, on peut citer 45 l'acide all-trans rétinoïque et l'acide 13-cis rétinoïque ainsi que leurs sels ou esters physiologiquement (pharmaceutiquement ou cosmétiquement) acceptables. Among the particularly preferred retinoids, mention may be made of all-trans retinoic acid and 13-cis retinoic acid as well as their physiologically (pharmaceutically or cosmetically) acceptable salts or esters.
Ces composés, lorsqu'ils sont présents, sont utilisés dans des proportions pouvant varier entre 0,01 et 10% en poids pour les dérivés 50 de pyrimidine et entre 0,001 et 2% en poids pour les rétinoïdes. These compounds, when they are present, are used in proportions which can vary between 0.01 and 10% by weight for the pyrimidine derivatives and between 0.001 and 2% by weight for the retinoids.
Ces composés peuvent être utilisés dans la même composition que le composé de formule (I), ou être appliqués séparément, soit simultanément ou de façon décalée dans le temps, avant ou après la composition contenant le composé de formule (I). 55 Les compositions conformes à l'invention peuvent se présenter sous forme de lotions, d'émulsions, de crèmes, de gels, et éventuellement être pressurisées en aérosol. Elles peuvent être appliquées notamment dans les traitements mettant en œuvre une composition telle que définie ci-dessus, dont l'application est ou non suivie d'un 60 rinçage, ou encore sous forme de shampooing. These compounds can be used in the same composition as the compound of formula (I), or can be applied separately, either simultaneously or in a time-shifted manner, before or after the composition containing the compound of formula (I). The compositions in accordance with the invention may be in the form of lotions, emulsions, creams, gels, and optionally be pressurized in an aerosol. They can be applied in particular in treatments using a composition as defined above, the application of which is or is not followed by rinsing, or also in the form of shampoo.
Le milieu cosmétiquement ou pharmaceutiquement acceptable peut être constitué par un milieu alcoolique ou encore par un milieu aqueux épaissi ou non, pouvant contenir un ou plusieurs solvants cosmétiquement ou pharmaceutiquement acceptables. 65 Les solvants sont choisis de préférence parmi les alcools inférieurs en Cj-Q tels que l'alcool éthylique, l'alcool isopropylique et l'alcool tertio-butylique; des alkylèneglycols comme le propylènegly-col et les alkyléthers de mono- et de dialkylèneglycols tels que le mo- The cosmetically or pharmaceutically acceptable medium may consist of an alcoholic medium or alternatively of an aqueous medium, thickened or not, which may contain one or more cosmetically or pharmaceutically acceptable solvents. The solvents are preferably chosen from lower Cj-Q alcohols such as ethyl alcohol, isopropyl alcohol and tert-butyl alcohol; alkylene glycols such as propylene glycol and the alkyl ethers of mono- and dialkylene glycols such as mo-
672 423 672,423
4 4
noéthyléther d'éthylèneglycol, le monométhyléther de propylènegly-col et le monoéthyléther de diéthylèneglycol. ethylene glycol noethyl ether, propylene glycol monomethyl ether and diethylene glycol monoethyl ether.
Ces compositions peuvent contenir d'autres adjuvants habituellement utilisés dans le domaine cosmétique ou pharmaceutique, en-vue de réaliser des compositions topiques, tels que plus particulièrement des agents tensio-actifs, des agents épaississants, des agents conservateurs, des agents alcalinisants ou acidifiants. Le pH de ces compositions peut varier entre 3 et 9 et de préférence entre 5 et 8. These compositions may contain other adjuvants usually used in the cosmetic or pharmaceutical field, with a view to producing topical compositions, such as more particularly surface-active agents, thickening agents, preserving agents, basifying or acidifying agents. The pH of these compositions can vary between 3 and 9 and preferably between 5 and 8.
Les agents épaississants ou gélifiants peuvent être choisis plus particulièrement parmi les hétérobiopolysaccharides, tels que par exemple ceux comportant des unités mannose, glucose, acide glucu-ronique ou galacturonique dans leurs chaînes, et plus particulièrement les gommes de xanthanne ou les scléroglucanes. The thickening or gelling agents can be chosen more particularly from heterobiopolysaccharides, such as for example those comprising mannose, glucose, glucuronic or galacturonic acid in their chains, and more particularly xanthan gums or scleroglucans.
On peut citer parmi ces produits ceux commercialisés sous la dénomination de KELTROL T ou TF, KELZAN S, KELZAN K9C57, KELZAN K8B12, KELZAN K3B130, commercialisés par la société Kelco; les produits vendus sous la dénomination de RHO-DOPOL 23 et 23SC ou bien RHODIGEL 23 par la société Rhône-Poulenc; le produit commercialisé sous la dénomination de DEUTERON XG par la société Schoner GmbH; les produits commercialisés sous la dénomination d'ACTIGUM CX9, CS 11 et C56 par la société Ceca/Satia; d'autres hétérobiopolysaccharides pouvant être utilisés sont décrits à titre illustratif dans les demandes ou brevets EP-A-23 397, UK-A-2 058 106, UK-A-2 058 107, US-A-4 454 316, EP-A-64 354, DE-A-3 224 547. These products include those sold under the name of KELTROL T or TF, KELZAN S, KELZAN K9C57, KELZAN K8B12, KELZAN K3B130, marketed by the company Kelco; the products sold under the name RHO-DOPOL 23 and 23SC or RHODIGEL 23 by the company Rhône-Poulenc; the product marketed under the name of DEUTERON XG by the company Schoner GmbH; the products marketed under the name of ACTIGUM CX9, CS 11 and C56 by the company Ceca / Satia; other heterobiopolysaccharides which can be used are described by way of illustration in patent applications or patents EP-A-23,397, UK-A-2,058,106, UK-A-2,058,107, US-A-4,454,316, EP- A-64 354, DE-A-3 224 547.
D'autres agents gélifiants peuvent être choisis parmi les dérivés de la cellulose tels que la méthylcellulose, l'hydroxyméthylcellulose, la carboxyméthylcellulose, l'hydroxybutylcellulose, l'hydroxyéthyl-cellulose, l'hydroxypropylcellulose, la méthylhydroxyéthylcellulose, la méthylhydroxypropylcellulose. Ces agents épaississants ou gélifiants sont de préférence utilisés dans des proportions de 0,5 à 5% et en particulier de 1 à 3% en poids par rapport au poids total de la composition. Other gelling agents can be chosen from cellulose derivatives such as methylcellulose, hydroxymethylcellulose, carboxymethylcellulose, hydroxybutylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, methylhydroxyethylcellulose, methylhydroxypropylcellulose. These thickening or gelling agents are preferably used in proportions of 0.5 to 5% and in particular from 1 to 3% by weight relative to the total weight of the composition.
Des agents épaississants utilisables peuvent cependant être choisis parmi les acides polyacryliques réticulés par un agent poly-fonctionnel tel que les produits vendus sous la dénomination de CARBOPOL par la société Goodrich ou les épaississants résultant de l'interaction ionique d'un polymère cationique constitué par un copolymère de cellulose ou d'un dérivé de cellulose greffés avec un sel de monomère hydrosoluble d'ammonium quaternaire et d'un polymère anionique carboxylique. Parmi ces derniers produits, on peut plus particulièrement citer les épaississants résultant de l'interaction d'un copolymère d'hydroxyalkylcellulose greffé par voie radicalaire par un sel de méthacryloyléthyl triméthylammonium, de méthacryl-amidopropyl triméthylammonium ou de diméthyl diallylammonium et d'un polymère anionique carboxylique choisi parmi les homopo-lymères de l'acide méthacrylique, les copolymères de l'acide méth-acrylique avec un monomère choisi parmi les acrylates ou méthacry-lates d'alkyle en Cj-Q, les dérivés d'acrylamide, l'acide maléique, les monomalêates d'alkyle en C1-C4, la vinylpyrrolidone et les copolymères d'éthylène et d'anhydride maléique. Le rapport pondéral entre le polymère cationique et le polymère anionique carboxylique est compris entre 1/5 et 5/1. Thickening agents which can be used can however be chosen from polyacrylic acids crosslinked with a polyfunctional agent such as the products sold under the name CARBOPOL by the company Goodrich or the thickeners resulting from the ionic interaction of a cationic polymer constituted by a copolymer of cellulose or of a cellulose derivative grafted with a salt of water-soluble quaternary ammonium monomer and of an anionic carboxylic polymer. Among these latter products, mention may more particularly be made of thickeners resulting from the interaction of a hydroxyalkylcellulose copolymer grafted by the radical route with a methacryloylethyl trimethylammonium salt, methacryl-amidopropyl trimethylammonium or dimethyl diallylammonium salt and an anionic polymer. carboxylic chosen from homopolymers of methacrylic acid, copolymers of methacrylic acid with a monomer chosen from Cj-Q alkyl acrylates or methacrylates, acrylamide derivatives, acid maleic, C1-C4 alkyl monomaleates, vinylpyrrolidone and copolymers of ethylene and maleic anhydride. The weight ratio between the cationic polymer and the anionic carboxylic polymer is between 1/5 and 5/1.
Les agents épaississants sont utilisés dans des proportions comprises entre 0,5 et 2% et de préférence entre 0,7 et 1,5% en poids. The thickening agents are used in proportions of between 0.5 and 2% and preferably between 0.7 and 1.5% by weight.
Le traitement pour lutter contre la chute des cheveux consiste principalement à appliquer, sur les zones alopéciques du cuir chevelu et les cheveux de l'individu, une composition telle que définie ci-dessus, par exemple après lavage du cuir chevelu et des cheveux à l'aide d'un shampooing ou peu de temps après un shampooing. Le mode d'application préféré consiste à appliquer 1 à 2 g de la composition selon l'invention sur la zone alopécique ayant une surface de 200 à 300 cm2 du cuir chevelu, à une fréquence de une ou deux applications par jour pendant 1 à 7 jours par semaine. The treatment for combating hair loss mainly consists in applying, to the alopecic areas of the scalp and the individual's hair, a composition as defined above, for example after washing the scalp and using a shampoo or shortly after shampooing. The preferred mode of application consists in applying 1 to 2 g of the composition according to the invention to the alopecic area having an area of 200 to 300 cm 2 of the scalp, at a frequency of one or two applications per day for 1 to 7 days a week.
L'efficacité du traitement est contrôlée une fois par mois au pho-totrichogramme. The effectiveness of the treatment is checked once a month on the pho-totrichogram.
La titulaire a constaté un accroissement significatif de la densité totale des cheveux avec une augmentation des cheveux en phase anagène et une diminution des cheveux en phase télogène après 2 mois de traitement. The licensee noted a significant increase in total hair density with an increase in hair in the anagen phase and a decrease in hair in the telogen phase after 2 months of treatment.
L'invention a également pour objet l'utilisation des composés de formule (I) pour la préparation d'une composition ayant pour effet d'induire et de stimuler la croissance des cheveux et freiner leur chute. A subject of the invention is also the use of the compounds of formula (I) for the preparation of a composition having the effect of inducing and stimulating the growth of the hair and curbing its fall.
Le procédé de traitement présente les caractéristiques d'un procédé cosmétique dans la mesure où il permet de soigner les cheveux et le cuir chevelu au sens cosmétique du terme, c'est-à-dire leur apporter les substances qui leur manquent et les embellir. The treatment process has the characteristics of a cosmetic process insofar as it makes it possible to treat the hair and the scalp in the cosmetic sense of the term, that is to say to provide them with the substances which they lack and to beautify them.
Le procédé présente par ailleurs les caractéristiques d'un traitement thérapeutique dans la mesure où la substance active a une activité thérapeutique au niveau des mécanismes biologiques du cycle pilaire. The method also has the characteristics of a therapeutic treatment insofar as the active substance has a therapeutic activity at the level of the biological mechanisms of the hair cycle.
Les exemples suivants sont destinés à illustrer l'invention sans pour autant présenter un caractère limitatif. The following examples are intended to illustrate the invention without, however, being limiting in nature.
Exemple 1 : Example 1:
On prépare la lotion active sur la croissance des cheveux et la diminution de leur chute, de composition suivante: The active lotion on hair growth and reduction of hair loss, of the following composition, is prepared:
— Monochlorhydrate de N,-(amino-4 diméthoxy-6,7 quinazolyl-2) Nj-méthyl N2-(tétrahydrofuroyl-2) - N monohydrochloride - (4-amino-dimethoxy-6,7 quinazolyl-2) Nj-methyl N2- (tetrahydrofuroyl-2)
propylène diamine 1 propylene diamine 1
— Conservateur, parfum q.s. - Preservative, perfume q.s.
— Eauq.s.p. 100 - Eauq.s.p. 100
On évalue l'activité de la composition pour stimuler la repousse des cheveux par rapport à un placebo, en appliquant 1 ml de cette composition à raison d'une application par jour sur une zone alopécique du cuir chevelu de cinq individus d'un âge moyen de 40 ans. En quelques mois de traitement, la composition améliore efficacement l'état de la chevelure. The activity of the composition for stimulating hair regrowth is evaluated compared to a placebo, by applying 1 ml of this composition at the rate of one application per day to an alopecic area of the scalp of five individuals of average age. 40 years old. In a few months of treatment, the composition effectively improves the condition of the hair.
Exemple 2: Example 2:
On prépare la lotion active sur la croissance des cheveux et la diminution de leur chute, de composition suivante: The active lotion on hair growth and reduction of hair loss, of the following composition, is prepared:
— Monochlorhydrate de Nr(amino-4 diméthoxy-6,7 quinazolyl-2) N^méthyl N2-(cyclopentylcarbonyl) - Nr monohydrochloride (4-amino-6,7-dimethoxy-2-quinazolyl) N ^ methyl N2- (cyclopentylcarbonyl)
propylène diamine 2 propylene diamine 2
— Conservateur, parfum q.s. - Preservative, perfume q.s.
— Eauq.s.p. 100 Exemple 3: - Eauq.s.p. 100 Example 3:
On prépare un gel actif pour stimuler la croissance des cheveux et freiner leur chute, de composition suivante: An active gel is prepared to stimulate hair growth and stop hair loss, of the following composition:
— Monochlorhydrate de Nj-Camino-4 diméthoxy-6,7 quinazolyl-2) Nj-méthyl N2-(tétrahydrofuroyl-2) - Nj-Camino-4-dimethoxy-6,7-quinazolyl-2) monohydrochloride Nj-methyl N2- (tetrahydrofuroyl-2)
propylène diamine 3 propylene diamine 3
— Hétéropolysaccharide vendu par la société Kelco sous la dénomination KELTROL T 1 - Heteropolysaccharide sold by the company Kelco under the name KELTROL T 1
— Alcool isopropylique 30 - Isopropyl alcohol 30
— Eauq.s.p. 100 - Eauq.s.p. 100
Exemple 4: Example 4:
On prépare un gel actif pour stimuler la croissance des cheveux et freiner leur chute, de composition suivante: An active gel is prepared to stimulate hair growth and stop hair loss, of the following composition:
— Monochlorhydrate de N1-(amino-4 diméthoxy-6,7 quinazolyl-2) Nj-méthyl N2-(tétrahydrofuroyl-2) - N1- (4-amino-dimethoxy-6,7 quinazolyl-2) monohydrochloride Nj-methyl N2- (tetrahydrofuroyl-2)
propylène diamine 2 propylene diamine 2
— Hydroxypropylcellulose vendue par la société Hercules sous la dénomination KLUCEL G 3 - Hydroxypropylcellulose sold by Hercules under the name KLUCEL G 3
— Alcool isopropylique q.s.p. 100 - Isopropyl alcohol q.s.p. 100
Exemple 5: Example 5:
On prépare une lotion active pour stimuler la croissance des cheveux et freiner leur chute, de composition suivante: An active lotion is prepared to stimulate hair growth and stop hair loss, of the following composition:
5 5
10 10
15 15
20 20
25 25
30 30
35 35
40 40
45 45
50 50
55 55
60 60
65 65
5 5
672 423 672,423
— Monochlorhydrate de N1-(amino-4 diméthoxy-6,7 quinazolyl-2) Nj-méthyl N2-(tétrahydrofuroyl-2) - N1- (4-amino-dimethoxy-6,7 quinazolyl-2) monohydrochloride Nj-methyl N2- (tetrahydrofuroyl-2)
propylène diamine 3 g propylene diamine 3 g
— Propylène glycol 20 g - Propylene glycol 20 g
— Alcool éthylique 50 g - Ethyl alcohol 50 g
— Eau q.s.p. 100 g - Water q.s.p. 100g
Appliquée pendant 2 mois à raison d'une application par jour sur le cuir chevelu, on constate une augmentation de l'ordre de 15% de la densité des cheveux, accompagnée par un accroissement significatif des cheveux en phase anagène et une diminution des cheveux en phase télogène. Applied for 2 months at the rate of one application per day to the scalp, there is an increase of about 15% in hair density, accompanied by a significant increase in hair in the anagen phase and a decrease in hair in telogen phase.
Exemple 6: Example 6:
On prépare une lotion active pour stimuler la croissance des 15 cheveux et freiner leur chute, de composition suivante: An active lotion is prepared to stimulate the growth of the hair and curb its fall, of the following composition:
— Monochlorhydrate de Nj-(amino-4 diméthoxy-6,7 quinazolyl-2) Nj-méthyl N2-(tétrahydrofuroyl-2) - Nj- monohydrochloride (4-amino-dimethoxy-6,7 quinazolyl-2) Nj-methyl N2- (tetrahydrofuroyl-2)
propylène diamine 1,5 g 20 propylene diamine 1.5 g 20
— Amino-6 dihydro-1,2 hydroxy-1 imino-2 pipéridino-4 pyrimidine 1,5 g - Amino-6 dihydro-1,2 hydroxy-1 imino-2 pipéridino-4 pyrimidine 1,5 g
— Propylène glycol 20 g - Propylene glycol 20 g
— Alcool éthylique 50 g - Ethyl alcohol 50 g
— Eauq.s.p. 100 - Eauq.s.p. 100
Exemple 7: Example 7:
On prépare une lotion active pour stimuler la croissance des cheveux et freiner leur chute, de composition suivante: An active lotion is prepared to stimulate hair growth and stop hair loss, of the following composition:
— Monochlorhydrate de N1-(amino-4 diméthoxy-6,7 quinazolyl-2) Nj-méthyl N2-(tétrahydrofuroyl-2) - N1- (4-amino-dimethoxy-6,7 quinazolyl-2) monohydrochloride Nj-methyl N2- (tetrahydrofuroyl-2)
propylène diamine 0,3 g propylene diamine 0.3 g
— Acide 13-cis rétinoïque 0,025 g - 13-cis retinoic acid 0.025 g
— Alcool éthylique 95 g - Ethyl alcohol 95 g
— Propylène glycol q.s.p. 100 g - Propylene glycol q.s.p. 100g
Exemple 8: Example 8:
On prépare un gel actif pour stimuler la croissance des cheveux et freiner leur chute, de composition suivante: An active gel is prepared to stimulate hair growth and stop hair loss, of the following composition:
— Monochlorhydrate de N1-(amino-4 diméthoxy-6,7 quinazolyl-2) Nx-méthyl N2-(tétrahydrofuroyl-2) - N1- hydrochloride (4-amino-6,7-dimethoxy-2-quinazolyl) Nx-methyl N2- (tetrahydrofuroyl-2)
propylène diamine propylene diamine
— Acide trans rétinoïque Alcool éthylique - Trans retinoic acid Ethyl alcohol
Acide polyacrylique vendu par la société Goodrich sous le nom de CARBOPOL 940 Polyacrylic acid sold by the company Goodrich under the name of CARBOPOL 940
— Eau - Water
— Conservateur q.s. - Curator q.s.
— Triéthanolamine q.s. pH 5 25 — Propylène glycol q.s.p. - Triethanolamine q.s. pH 5 25 - Propylene glycol q.s.p.
0,75 g 0,0125 g 50 g 0.75 g 0.0125 g 50 g
1 g 13 g 1 g 13 g
100 I 100 I
R R
Claims (13)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86672A LU86672A1 (en) | 1986-11-19 | 1986-11-19 | COMPOSITION FOR INDUCING AND STIMULATING HAIR GROWTH AND REDUCING FALL BASED ON ALKYLENE DIAMINO QUINAZOLINE DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH672423A5 true CH672423A5 (en) | 1989-11-30 |
Family
ID=19730816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4508/87A CH672423A5 (en) | 1986-11-19 | 1987-11-19 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS63135316A (en) |
| BE (1) | BE1000621A3 (en) |
| CA (1) | CA1297411C (en) |
| CH (1) | CH672423A5 (en) |
| DE (1) | DE3739207A1 (en) |
| ES (1) | ES2009222A6 (en) |
| FR (1) | FR2606635B1 (en) |
| GB (1) | GB2197589B (en) |
| IT (1) | IT1211544B (en) |
| LU (1) | LU86672A1 (en) |
| NL (1) | NL8702772A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2814090B2 (en) * | 1988-12-14 | 1998-10-22 | 株式会社資生堂 | Hair restoration |
| KR930001805B1 (en) * | 1989-10-02 | 1993-03-13 | 브리스톨-마이어즈 스퀴브 컴페니 | Tretinoin emulsified cream formulations of improved stability |
| FR2694495B1 (en) * | 1992-08-05 | 1994-09-23 | Synthelabo | Transdermal pharmaceutical preparation containing alfuzosin. |
| FR2717381B1 (en) * | 1994-03-15 | 1996-04-19 | Oreal | Compositions based on alpha-pyrones to induce and stimulate hair growth and / or slow down hair loss and use. |
| DE69842109D1 (en) * | 1997-08-21 | 2011-03-10 | Shiseido Co Ltd | Quinazolin-4-one derivatives, their preparation and their use as hair restorers or in topical skin care products |
| FR2826262B1 (en) * | 2001-06-26 | 2005-02-25 | Oreal | COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING AN ASSOCIATION BETWEEN A COMPOUND OF THE FAMILY OF N-ACYLAMINOAMIDES AND AT LEAST ONE COMPOUND ACTING ON THE FALL OR REPROSE OF HAIR |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421888A1 (en) * | 1978-02-06 | 1979-11-02 | Synthelabo | ALKYLENE DIAMINE AMIDES AND THEIR APPLICATION IN THERAPEUTICS |
| FR2466462A2 (en) * | 1978-02-06 | 1981-04-10 | Synthelabo | Antihypertensive quinazoline derivs. - substd. by 2-acylamino: alkylamino group |
| FR2468595B2 (en) * | 1979-10-30 | 1986-03-14 | Synthelabo | ALKYLENE DIAMINE AMIDES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| DE3280344D1 (en) * | 1981-11-09 | 1991-07-25 | Gail S Bazzano | USE OF RETINOIDES AND MINOXIDIL (2,4-DIAMINO-6-PIPERIDINO-PYRIMIDINE-3-OXIDE) TO IMPROVE THE GROWTH OF HUMAN HEAD HAIR AND TO TREAT CERTAIN TYPES OF ALOPECIA. |
| NZ214397A (en) * | 1984-12-21 | 1989-04-26 | Richardson Vicks Inc | Minoxidil and acrylate polymer topical compositions |
-
1986
- 1986-11-19 LU LU86672A patent/LU86672A1/en unknown
-
1987
- 1987-11-18 ES ES8703289A patent/ES2009222A6/en not_active Expired
- 1987-11-18 JP JP62289651A patent/JPS63135316A/en active Pending
- 1987-11-18 FR FR878715952A patent/FR2606635B1/en not_active Expired - Fee Related
- 1987-11-19 DE DE19873739207 patent/DE3739207A1/en not_active Withdrawn
- 1987-11-19 IT IT8767993A patent/IT1211544B/en active
- 1987-11-19 BE BE8701315A patent/BE1000621A3/en not_active IP Right Cessation
- 1987-11-19 NL NL8702772A patent/NL8702772A/en not_active Application Discontinuation
- 1987-11-19 CH CH4508/87A patent/CH672423A5/fr not_active IP Right Cessation
- 1987-11-19 CA CA000552191A patent/CA1297411C/en not_active Expired - Fee Related
- 1987-11-19 GB GB8727113A patent/GB2197589B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA1297411C (en) | 1992-03-17 |
| FR2606635B1 (en) | 1991-06-14 |
| GB2197589B (en) | 1991-01-23 |
| IT1211544B (en) | 1989-11-03 |
| NL8702772A (en) | 1988-06-16 |
| DE3739207A1 (en) | 1988-07-28 |
| GB8727113D0 (en) | 1987-12-23 |
| LU86672A1 (en) | 1988-06-13 |
| JPS63135316A (en) | 1988-06-07 |
| BE1000621A3 (en) | 1989-02-21 |
| ES2009222A6 (en) | 1989-09-16 |
| FR2606635A1 (en) | 1988-05-20 |
| IT8767993A0 (en) | 1987-11-19 |
| GB2197589A (en) | 1988-05-25 |
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