CA2285886A1 - Compounds containing oxadiazolopyrimidines destined to be used for slowing down hair loss and for inducing and stimulating their growth - Google Patents
Compounds containing oxadiazolopyrimidines destined to be used for slowing down hair loss and for inducing and stimulating their growth Download PDFInfo
- Publication number
- CA2285886A1 CA2285886A1 CA002285886A CA2285886A CA2285886A1 CA 2285886 A1 CA2285886 A1 CA 2285886A1 CA 002285886 A CA002285886 A CA 002285886A CA 2285886 A CA2285886 A CA 2285886A CA 2285886 A1 CA2285886 A1 CA 2285886A1
- Authority
- CA
- Canada
- Prior art keywords
- radical
- group
- linear
- formula
- saturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 201000004384 Alopecia Diseases 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 208000024963 hair loss Diseases 0.000 title abstract 2
- 230000003676 hair loss Effects 0.000 title abstract 2
- 230000001939 inductive effect Effects 0.000 title 1
- POSWMWNNGRNENE-UHFFFAOYSA-N oxadiazolo[5,4-d]pyrimidine Chemical class C1=NC=C2N=NOC2=N1 POSWMWNNGRNENE-UHFFFAOYSA-N 0.000 title 1
- 230000004936 stimulating effect Effects 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 8
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000005505 thiomorpholino group Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Landscapes
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne une composition pharmaceutique ou cosmétique, destinée à être utilisée en application topique pour freiner la chute des cheveux et pour induire et stimuler leur croissance. La composition selon l'invention est caractérisée par le fait qu'elle contient dans un milieu physiologiquement acceptable, au moins un composé répondant à la formule générale: (voir formule III) dans laquelle: R désigne un atome d'hydrogène, un radical alkyle, saturé et linéaire, en C1-C8 ou forme avec le cycle pyrimidine, un cycle hydrocarboné de formule: (voir formule ci-haut) 63 où n est égal à 1, 2 ou 3; X désigne (i) un atome d'hydrogène; (ii)un groupement de formule: <IMG> dans laquelle R1 et R2, identiques ou différents, désignent un atome d'hydrogène, un groupe alkyle saturé en C1-C12, linéaire ou ramifié, non substitué ou substitué par un atome d'halogène ou un radical trifluorométhyle, un groupe alcényle linéaire en C2-C12, un groupe cycloalkyle en C3-C10, un groupe aralkyle en C7-C12 ou un groupement aryle répondant à la formule: <IMG> dans laquelle R9 et R10, identiques ou différents, désignent un atome d'hydrogène ou d'halogène, ou un groupe alkyle en C1-C4, hydroxyle ou alcoxy en C1-C4; ou bien R1 et R2 forment avec l'atome d'azote auquel ils sont reliés, un hétérocycle saturé ou insaturé, choisi parmi les groupe aziridino, azétidino, pyrrolidino, pipéridino, hexaméthylèneimino, heptaméthylèneimino octaméthylèneimino, tétrahydropyridino, dihydropyridino, pyrrole, pyrrazole, imidazole et thiomorpholino; (iii) un groupement -OR3, dans lequel R3 désigne un radical alkyle saturé en C1-C12, linéaire ou ramifié, non substitué ou substitué par un atome d'halogène ou un radical trifluorométhyle, un radical alcényle linéaire en C2-C12, un radical cycloalkyle en 64 C3-C10, un radical aralkyle en C7-C12, un radical phényle éventuellement substitué par un ou deux groupement, qui, indépendamment l'un de l'autre, désignent un atome d'halogène, un radical alkyle en C1-C6, un radical alcoxy en C1-C6, ou un radical trifluorométhyle; ou (iv) un groupement -SR4, dans lequel R4 a la même signification que R3; ou l'un de ses sels d'addition d'acides physiologiquement acceptables.The invention relates to a pharmaceutical or cosmetic composition, intended to be used in topical application to slow down hair loss and to induce and stimulate their growth. The composition according to the invention is characterized in that it contains, in a physiologically acceptable medium, at least one compound corresponding to the general formula: (see formula III) in which: R denotes a hydrogen atom, an alkyl radical , saturated and linear, in C1-C8 or form with the pyrimidine ring, a hydrocarbon ring of formula: (see formula above) 63 where n is equal to 1, 2 or 3; X denotes (i) a hydrogen atom; (ii) a group of formula: <IMG> in which R1 and R2, identical or different, denote a hydrogen atom, a saturated C1-C12 alkyl group, linear or branched, unsubstituted or substituted by an atom halogen or a trifluoromethyl radical, a linear C2-C12 alkenyl group, a C3-C10 cycloalkyl group, a C7-C12 aralkyl group or an aryl group corresponding to the formula: <IMG> in which R9 and R10, identical or different, denote a hydrogen or halogen atom, or a C1-C4 alkyl, hydroxyl or C1-C4 alkoxy group; or R1 and R2 form, with the nitrogen atom to which they are linked, a saturated or unsaturated heterocycle, chosen from the groups aziridino, azétidino, pyrrolidino, pipéridino, hexamethyleneimino, heptamethyleneimino octamethyleneimino, tetrahydropyridino, dihydropyridino, pyrrole, pyrrazole and thiomorpholino; (iii) a group -OR3, in which R3 denotes a saturated C1-C12 alkyl radical, linear or branched, unsubstituted or substituted by a halogen atom or a trifluoromethyl radical, a linear C2-C12 alkenyl radical, a C3-C10 cycloalkyl radical, a C7-C12 aralkyl radical, a phenyl radical optionally substituted by one or two groups, which, independently of one another, denote a halogen atom, a C1-alkyl radical -C6, a C1-C6 alkoxy radical, or a trifluoromethyl radical; or (iv) a group -SR4, in which R4 has the same meaning as R3; or one of its physiologically acceptable acid addition salts.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8911352A FR2651122B1 (en) | 1989-08-29 | 1989-08-29 | COMPOSITIONS FOR USE IN BRAKING HAIR LOSS AND INDUCING AND STIMULATING THEIR GROWTH, CONTAINING 2-AMINO PYRIMIDINE OXIDE-3 DERIVATIVES AND NEW AMINO-2 PYRIMIDINE OXIDE-3 DERIVATIVES. |
| FR8911352 | 1989-08-29 | ||
| CA002024156A CA2024156C (en) | 1989-08-29 | 1990-08-28 | Compositions for use in controling the shedding of hair and in the induction and stimulation of its growth, such compositions containing 2-amino pyrimidine 3-oxide derivatives andnovel 2-amino pyrimidine 3-oxide derivative compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002024156A Division CA2024156C (en) | 1989-08-29 | 1990-08-28 | Compositions for use in controling the shedding of hair and in the induction and stimulation of its growth, such compositions containing 2-amino pyrimidine 3-oxide derivatives andnovel 2-amino pyrimidine 3-oxide derivative compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285886A1 true CA2285886A1 (en) | 1991-03-01 |
| CA2285886C CA2285886C (en) | 2002-01-01 |
Family
ID=25674282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285886A Expired - Fee Related CA2285886C (en) | 1989-08-29 | 1990-08-28 | Compounds containing oxadiazolopyrimidines destined to be used for slowing down hair loss and for inducing and stimulating their growth |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2285886C (en) |
-
1990
- 1990-08-28 CA CA002285886A patent/CA2285886C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2285886C (en) | 2002-01-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |