FR2678614A1 - Compound having activity as a collagenase inhibitor and medicament containing it - Google Patents
Compound having activity as a collagenase inhibitor and medicament containing it Download PDFInfo
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- FR2678614A1 FR2678614A1 FR9108303A FR9108303A FR2678614A1 FR 2678614 A1 FR2678614 A1 FR 2678614A1 FR 9108303 A FR9108303 A FR 9108303A FR 9108303 A FR9108303 A FR 9108303A FR 2678614 A1 FR2678614 A1 FR 2678614A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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Abstract
Description
L'invention a pour objet des composés présentant une activité en tant qu'inhibiteur de la collagénase. The subject of the invention is compounds having activity as a collagenase inhibitor.
Elle a également pour objet l'utilisation de ces composés pour la préparation de médicaments permettant de réparer certains désordres du tissu conjonctif notamment prévention des parodontopathies et de l'arthrose. It also relates to the use of these compounds for the preparation of medicaments making it possible to repair certain disorders of the connective tissue in particular prevention of periodontopathies and osteoarthritis.
On sait que la dégradation de la matrice du cartilage est due à l'action de métalloprotéase extra-cellulaire active à pH neutre. It is known that the degradation of the cartilage matrix is due to the action of active extracellular metalloprotease at neutral pH.
I1 s'agit de protéoglycanases qui fragmentent les protéoglycanes et de collagénases qui attaquent les fibres de collagène. Dans le même temps, les cellules chondrocytaires sont soumises à des stimuli visant à provoquer un processus de réparation, les chondrocytes arthrosiques synthétisant plus de protéoglycanes et de collagène. These are proteoglycanases which fragment the proteoglycans and collagenases which attack the collagen fibers. At the same time, the chondrocyte cells are subjected to stimuli aimed at inducing a repair process, the arthritic chondrocytes synthesizing more proteoglycans and collagen.
Les produits qui inhibent la synthèse et l'activation des enzymes de dégradation du cartilage sont peu nombreux et mal connus. There are few products that inhibit the synthesis and activation of cartilage-degrading enzymes.
Cependant, divers travaux expérimentaux ont pu montrer que les polysaccharides, la vitamine C, les corticoldes et peut être certains anti-inflammatoires non stéroîdiens pouvaient avoir un tel effet. However, various experimental studies have been able to show that polysaccharides, vitamin C, corticosteroids and perhaps some non-steroidal anti-inflammatory drugs could have such an effect.
Le déposant a trouvé que d'autres composés pouvaient être utilisés pour entretenir le fonctionnement du cartilage articulaire. The applicant has found that other compounds could be used to maintain the functioning of articular cartilage.
Selon l'invention, les composés répondent à la formule
R-A I dans laquelle A est une chaîne linéaire hydrocarbonée en C1 1-C19, de préférence C13-Cl7 saturée ou comprenant une ou plusieurs insaturations éthyléniques ou acétyléniques, R est choisi parmi les groupes 2-furanyle ou
X-O-CH2-CHOH-CH2-C(=O)- où X est l'atome d'hydrogène ou un groupe acétyle.According to the invention, the compounds correspond to the formula
RA I in which A is a linear C1 1-C19 hydrocarbon chain, preferably C13-Cl7 saturated or comprising one or more ethylenic or acetylenic unsaturations, R is chosen from the 2-furanyl groups or
XO-CH2-CHOH-CH2-C (= O) - where X is the hydrogen atom or an acetyl group.
Ces composés peuvent être obtenus par des procédés divers, notamment à partir d'insaponifiable ou d'huile d'avocat par des méthodes d'extraction ou d'hémisynthèse décrites ci-après. These compounds can be obtained by various methods, in particular from unsaponifiable matter or avocado oil by extraction or hemisynthesis methods described below.
L'insaponifiable est la fraction d'un corps gras qui après action prolongée d'une base alcaline, reste insoluble dans l'eau et peut être extraite par un solvant organique. Cinq grands groupes de substances sont présents dans la plupart des insaponifiables végétaux : hydrocarbures saturés ou insaturés, alcools aliphatiques ou terpèniques, stérols, tocophérols, les pigments caroténoîdes et xantophiles. The unsaponifiable is the fraction of a fatty substance which after prolonged action of an alkaline base, remains insoluble in water and can be extracted by an organic solvent. Five main groups of substances are present in most plant unsaponifiables: saturated or unsaturated hydrocarbons, aliphatic or terpene alcohols, sterols, tocopherols, carotenoid and xantophilic pigments.
Néanmoins, la comparaison des teneurs en insaponifiables de différentes huiles végétales : soja, coton, noix de coco, olive et avocat a révélé le taux important d'insaponifiable de l'huile d'avocat obtenue par divers procédés. Typiquement, les teneurs obtenues s'échelonnent de 2 à 7 % contre 0,5 % dans l'huile de coco, 1 % dans l'huile de soja, 1 % dans l'huile d'olive. Cette différence importante s'explique par la présence, dans l'insaponifiable d'avocat, de produits que l'on ne retrouve généralement pas dans l'insaponifiable de nombreuses autres huiles végétales et qui apparaissent majoritairement sur le chromatogramme obtenu après chromatographie gazeuse sur colonne capillaire de verre. A eux seuls, ces produits représentent plus de 50 % de l'insaponifiable. However, a comparison of the unsaponifiable levels of different vegetable oils: soybean, cotton, coconut, olive and avocado revealed the significant unsaponifiable level of avocado oil obtained by various processes. Typically, the contents obtained range from 2 to 7% against 0.5% in coconut oil, 1% in soybean oil, 1% in olive oil. This important difference is explained by the presence, in the unsaponifiable of avocado, of products which are generally not found in the unsaponifiable of many other vegetable oils and which appear mainly on the chromatogram obtained after gas chromatography on a column. glass capillary. These products alone represent more than 50% of the unsaponifiable matter.
Les produits propres à cet insaponifiable peuvent être répartis en deux fractions chimiques qu'on appellera "fraction I" et "fraction H". Les composés selon l'invention se trouvent présents dans la fraction H et ses précurseurs. La fraction H apparaît en premier lieu sur un chromatogramme en phase gazeuse de l'insaponifiable. Les conditions de préparation de l'huile président à l'apparition de la fraction H ou de ses précurseurs, qui eux sont détruits par la saponification. The products specific to this unsaponifiable matter can be divided into two chemical fractions which will be called "fraction I" and "fraction H". The compounds according to the invention are found in fraction H and its precursors. Fraction H appears first on a gas chromatogram of the unsaponifiable matter. The conditions for preparing the oil preside over the appearance of the fraction H or of its precursors, which are destroyed by saponification.
Une méthode de séparation des constituants des insaponifiables consiste à les éluer au travers d'une colonne remplie d'un gel de silice dont les particules sont de taille appropriée (entre 20 et 50 tjm de préférence) avec un solvant organique dont la polarité augmente après chaque fraction récupérée par exemple par mélange d'hexane et de chloroforme. Les composés comportant le cycle furanique font partie des premières fractions passant par élution avec un solvant peu polaire. One method of separating the constituents of the unsaponifiables consists in eluting them through a column filled with silica gel, the particles of which are of appropriate size (preferably between 20 and 50 μm) with an organic solvent whose polarity increases after each fraction recovered, for example by mixing hexane and chloroform. The compounds comprising the furan cycle are part of the first fractions passing by elution with a slightly polar solvent.
I1 est également possible de séparer les composés directement à partir de l'huile d'avocat extraite par le mélange chloroforme-méthanol, en utilisant les mêmes méthodes d'élution. Dans ce cas, les triglycérides présents dans ladite huile sont récupérés dans les fractions situées entre celles contenant les composés à cycles furanique et celles contenant les composés linéaires qui sont leurs précurseurs. It is also possible to separate the compounds directly from the avocado oil extracted by the chloroform-methanol mixture, using the same elution methods. In this case, the triglycerides present in said oil are recovered in the fractions located between those containing the compounds with furan rings and those containing the linear compounds which are their precursors.
Les composés selon l'invention de formule I dans laquelle R est le groupe 2-furanyle ne sont pas présents dans l'huile provenant de l'extraction directe d'avocat frais. Néanmoins, l'avocat contient les éléments précurseurs de cette fraction. Ces éléments précurseurs répondent à la formule I dans laquelle R est le groupe X-O-CH2-CHOH-CH2-C(=O)-,
X ayant la même signification que précédemment.The compounds according to the invention of formula I in which R is the 2-furanyl group are not present in the oil originating from the direct extraction of fresh avocado. However, avocado contains the precursors of this fraction. These precursor elements correspond to formula I in which R is the group XO-CH2-CHOH-CH2-C (= O) -,
X having the same meaning as before.
Un moyen d'obtenir les composés de formule I où R est le groupe 2-furanyle consiste à traiter thermiquement le fruit frais pendant au moins quatre heures avantageusement au moins 10 heures, de préférence entre 24 et 48 heures et à une température comprise entre 80 et 1200C puis à extraire lesdits composés de l'huile ou de l'insaponifiable. One way of obtaining the compounds of formula I where R is the 2-furanyl group consists in heat treating the fresh fruit for at least four hours, advantageously at least 10 hours, preferably between 24 and 48 hours and at a temperature between 80 and 1200C then extracting said compounds from the oil or from the unsaponifiable matter.
Un procédé pour obtenir les précurseurs de formule I consiste, à partir de fruit frais
a) à extraire l'huile de manière connue,
b) à purifier les différentes fractions notamment par chromatographie.A process for obtaining the precursors of formula I consists, from fresh fruit
a) extracting the oil in a known manner,
b) purifying the various fractions, in particular by chromatography.
Plus particulièrement, un procédé pour obtenir les composés de formule I où R est le groupe 2-furanyle consiste à traiter thermiquement le fruit avant extraction selon les conditions indiquées précédemment, soit 800 à 1200 durant 24-48 heures, de préférence. More particularly, a process for obtaining the compounds of formula I where R is the 2-furanyl group consists in heat treating the fruit before extraction according to the conditions indicated above, that is to say 800 to 1200 for 24-48 hours, preferably.
Avant sa saponification, l'huile peut être préalablement enrichie par distillation moléculaire centrifuge qui permet de séparer une majorité des constituants de l'insaponifiable que l'on récupère dans un concentrat. Before its saponification, the oil can be enriched beforehand by centrifugal molecular distillation which makes it possible to separate a majority of the constituents of the unsaponifiable matter which is recovered in a concentrate.
La saponification est ensuite effectuée de manière connue, en phase hydroalcoolique, la concentration préalable de l'huile en insaponifiable permettant de diminuer la consommation d'huile pendant la saponification. La solution d'insaponifiable est lavé à l'eau afin d'éliminer toute trace résiduelle d'alcalinité, puis on évapore le solvant d'extraction pour récupérer l'insaponifiable. The saponification is then carried out in a known manner, in the hydroalcoholic phase, the prior concentration of the oil in unsaponifiable making it possible to reduce the consumption of oil during the saponification. The unsaponifiable solution is washed with water in order to remove any residual alkalinity, then the extraction solvent is evaporated to recover the unsaponifiable matter.
Selon une variante préférée, les composés répondent aux formules
dans lesquelles R est choisi parmi les groupes 2-furanyle ou
X-O-CH2-CHOH-CH2-C(=O)- où X est l'atome d'hydrogène ou un groupe acétyle.According to a preferred variant, the compounds correspond to the formulas
in which R is chosen from the 2-furanyl groups or
XO-CH2-CHOH-CH2-C (= O) - where X is the hydrogen atom or an acetyl group.
De préférence encore, ils répondent aux formules Ib, If ou Ig dans lesquelles R est le groupe 2-furanyle. More preferably, they correspond to the formulas Ib, If or Ig in which R is the 2-furanyl group.
Il a été trouvé que ces composés étaient des inhibiteurs de la collagénase permettant de formuler des médicaments pour la prévention des dégradations du tissu conjonctif : par odontophaties, arthrose. These compounds have been found to be collagenase inhibitors which make it possible to formulate drugs for the prevention of damage to the connective tissue: by odontophaties, arthritis.
L'arthrose correspond à une destruction de la matrice du cartilage provoquée par les enzymes citées ci-dessus. Osteoarthritis is a destruction of the cartilage matrix caused by the enzymes mentioned above.
L'invention concerne en conséquence un médicament constitué d'un de ces composés et les compositions pharmaceutiques contenant au moins un médicament et un support acceptable. The invention therefore relates to a drug consisting of one of these compounds and to pharmaceutical compositions containing at least one drug and an acceptable carrier.
Les exemples ci-après illustrent l'invention sans la limiter
EXEMPLE 1
Composé de formule
EXAMPLE 1
Compound of formula
Ha # = 7,281 Ja,b = i,7Hz Hb # = 6,264 Ja,b = 0,9Hz Hc # = 5,959 Jb,c = 2,7Hz
Hia # = 4,924 J1a,1b = 2,0Hz
Hib # = 4,986 J1b,2= 17,1Hz
H2 # = 5,810 J1a,2= 10,3Hz
H3 # = 2,037 J2,3 = 6,8 Hz
H12 # = 1,626 J12,13 = 7,6Hz
H13 # = 2,606
H4a11 # = 1,3
EXEMPLE 2
Composé de formule
Hia # = 4,924 J1a, 1b = 2,0Hz
Hib # = 4,986 J1b, 2 = 17.1Hz
H2 # = 5.810 J1a, 2 = 10.3Hz
H3 # = 2,037 J2.3 = 6.8 Hz
H12 # = 1.626 J12.13 = 7.6Hz
H13 # = 2.606
H4a11 # = 1.3
EXAMPLE 2
Compound of formula
Ha # = 7,280 Ja,b = 2,0Hz
Hb # = 6,261 Ja,c = 0,9Hz
Hc # = 5,956 Jb,c = 2,7Hz H13 # = 2,603 J12,13 = 7,6Hz
H12 # = 1,623 H3 # = 2,172 J3,1= 2,9 Hz
H4 # = i,509
H1 # = i,925 J3,4 = 7,1Hz
EXEMPLE 3
Composé de formule :
Hb # = 6.261 Ja, c = 0.9Hz
Hc # = 5.956 Jb, c = 2.7Hz H13 # = 2.603 J12.13 = 7.6Hz
H12 # = 1.623 H3 # = 2.172 J3.1 = 2.9 Hz
H4 # = i, 509
H1 # = i, 925 J3.4 = 7.1Hz
EXAMPLE 3
Composed of formula:
Ha # = 7,295 Ja,b = 1,9Hz
Hb # = 6,328 Ja,b = 0,9Hz
Hc # = 6,112 Jb,c = 3,iHz
H13 # = 6,189 J1a,1b = 15,3Hz H12 # = 6,162
H11 # = 2,169 J10,11= 7,0Hz
H10 # = 1,432
(CH3)1 # = 1,925 J1,2=6,7Hz
EXEMPLE 4
Composé de formule
Hb # = 6.328 Ja, b = 0.9Hz
Hc # = 6.112 Jb, c = 3, iHz
H13 # = 6.189 J1a, 1b = 15.3Hz H12 # = 6.162
H11 # = 2.169 J10.11 = 7.0Hz
H10 # = 1,432
(CH3) 1 # = 1.925 J1.2 = 6.7Hz
EXAMPLE 4
Compound of formula
Ha # = 7,271 Ja,b = i,9Hz
Hb # = 6,264 Ja,c = 0,8Hz
Hc # = 5,958 Jb,c = 2,9Hz
H17 # = 2,608 J16,17 = 7,6Hz
H16 # = 1,630 J16,15= 7,1Hz
(CH2)III # = 2,771 J=,2Hz
(CH2) # = 2,048 JH, CHZ= 6,7Hz
Hb # = 6.264 Ja, c = 0.8Hz
Hc # = 5.958 Jb, c = 2.9Hz
H17 # = 2.608 J16.17 = 7.6Hz
H16 # = 1,630 J16.15 = 7.1Hz
(CH2) III # = 2,771 J =, 2Hz
(CH2) # = 2,048 JH, CHZ = 6.7Hz
JOH2, CH2 = 6,6Hz
CH3 =0,888 J=6,8Hz
Hethyleniques (I, II, IV, V)=5,3-5,4 J=11Hz cis JOH2, CH2 = 6.6Hz
CH3 = 0.888 J = 6.8Hz
Hethylenics (I, II, IV, V) = 5.3-5.4 J = 11Hz cis
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9108303A FR2678614A1 (en) | 1991-07-03 | 1991-07-03 | Compound having activity as a collagenase inhibitor and medicament containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9108303A FR2678614A1 (en) | 1991-07-03 | 1991-07-03 | Compound having activity as a collagenase inhibitor and medicament containing it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2678614A1 true FR2678614A1 (en) | 1993-01-08 |
| FR2678614B1 FR2678614B1 (en) | 1995-03-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9108303A Granted FR2678614A1 (en) | 1991-07-03 | 1991-07-03 | Compound having activity as a collagenase inhibitor and medicament containing it |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2678614A1 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0775480A1 (en) * | 1993-10-25 | 1997-05-28 | S. Richard Huber | Novel lipidic furans useful for skin therapeutics |
| WO1999055657A1 (en) * | 1998-04-29 | 1999-11-04 | Laboratoires Pharmascience | Novel compounds extracted from vegetable oil useful in pharmaceutics and cosmetics, in particular for inhibiting cell growth |
| FR2798667A1 (en) * | 1999-09-22 | 2001-03-23 | Pharmascience Lab | PROCESS FOR EXTRACTING POLYHYDROXYL FATTY COMPOUNDS AND POLYHYDROXYL FATTY ALCOHOLS, COMPOSITION THEREOF AND USE THEREOF IN THERAPEUTICS, COSMETICS AND FOOD |
| WO2004012496A2 (en) * | 2002-07-29 | 2004-02-12 | Laboratoires Expanscience | Method for producing an avocado unsaponifiable rich in furan lipids |
| FR2870742A1 (en) * | 2004-05-28 | 2005-12-02 | Expanscience Laboratoires Sa | USE OF ALKYL FURANS FOR THE PREPARATION OF A MEDICAMENT FOR THE TREATMENT OF DIABETES, OBESITY AND FOR THE COSMETIC TREATMENT OF CELLULITE AND OVERLOAD |
| US7589121B2 (en) | 2004-05-28 | 2009-09-15 | Laboratoires Expanscience | Use of furan alkyls for preparing a drug for treating obesity and cosmetically treating overweight |
| US7872043B2 (en) | 2004-05-28 | 2011-01-18 | Laboratories Expanscience | Use of furan alkyls for a cellulite cosmetic treatment |
| JP2016515585A (en) * | 2013-03-29 | 2016-05-30 | アボサイエンス、リミテッド、ライアビリティー、カンパニーＡｖｏｓｃｉｅｎｃｅ， Ｌｌｃ | Lipid furan, pyrrole and thiophene compounds for the treatment of cancer, neurological disorders and fibrotic disorders |
| US10905673B2 (en) | 2016-04-27 | 2021-02-02 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for use in the treatment of atrophic vaginitis |
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|---|---|---|---|---|
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-
1991
- 1991-07-03 FR FR9108303A patent/FR2678614A1/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1425343A (en) * | 1972-02-14 | 1976-02-18 | Unilever Ltd | Phthalic acid derivatives |
Non-Patent Citations (5)
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|---|
| CHEMICAL ABSTRACTS, vol. 103, no. 19, 11 Novembre 1985, Columbus, Ohio, US; abstract no. 157333D, L. PREVITERA ET AL.: 'Acetogenins from the aquatic plant Elodea canadensis' page 411 ;colonne 2 ; * |
| CHEMICAL ABSTRACTS, vol. 105, no. 21, 24 Novembre 1986, Columbus, Ohio, US; abstract no. 187627M, D. MEROLA: 'Elodea canadensis metabolites' page 421 ;colonne 1 ; * |
| CHEMICAL ABSTRACTS, vol. 115, no. 21, 25 Novembre 1991, Columbus, Ohio, US; abstract no. 232007D, ULKU OYMAN: 'Dehydration of some 1-(2-furyl) and 1-(2-thienyl)-1-alkanols using cobalt(II) sulfate as catalyst' page 924 ;colonne 2 ; * |
| CHEMICAL ABSTRACTS, vol. 72, no. 25, 22 Juin 1970, Columbus, Ohio, US; abstract no. 129380Q, L. NEEMAN ET AL.: 'New antibacterial agent isolated from the avocado pear' page 75 ;colonne 1 ; * |
| CHEMICAL ABSTRACTS, vol. 75, no. 19, 8 Novembre 1971, Columbus, Ohio, US; abstract no. 115910N, H. M. ALVES ET AL.: 'Avocatins. New class of natural products' page 27 ;colonne 2 ; * |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0775480A1 (en) * | 1993-10-25 | 1997-05-28 | S. Richard Huber | Novel lipidic furans useful for skin therapeutics |
| WO1999055657A1 (en) * | 1998-04-29 | 1999-11-04 | Laboratoires Pharmascience | Novel compounds extracted from vegetable oil useful in pharmaceutics and cosmetics, in particular for inhibiting cell growth |
| FR2778181A1 (en) * | 1998-04-29 | 1999-11-05 | Pharmascience Lab | NEW VEGETABLE OIL COMPOUNDS FOR USE IN THE PHARMACEUTICAL AND COSMETIC INDUSTRY, PARTICULARLY FOR THE INHIBITION OF CELL GROWTH |
| JP2003509506A (en) * | 1999-09-22 | 2003-03-11 | ラボラトワール ファルマシアンス | Method for extracting avocado furan lipid compounds and polyhydroxylated fatty alcohols, compositions based on the compounds and their use in therapy, beauty and food |
| WO2001021605A2 (en) * | 1999-09-22 | 2001-03-29 | Laboratoires Pharmascience | Method for extracting compounds of furan lipids and polyhydroxylated fatty alcohols of avocado, composition based on said compounds and use of said compounds in therapy, cosmetics and food |
| WO2001021605A3 (en) * | 1999-09-22 | 2001-10-25 | Pharmascience Lab | Method for extracting compounds of furan lipids and polyhydroxylated fatty alcohols of avocado, composition based on said compounds and use of said compounds in therapy, cosmetics and food |
| US6582688B1 (en) | 1999-09-22 | 2003-06-24 | Pharmascience | Method for extracting compounds of furan lipids and polyhydroxylated fatty alcohols of avocado, composition based on said compounds, and therapeutic, cosmetical or food use of said compounds |
| JP5021879B2 (en) * | 1999-09-22 | 2012-09-12 | ラボラトワール エクスパンシアンス | Methods for extracting avocado furan lipid compounds and polyhydroxylated fatty alcohols, compositions and treatments based on the compounds, use of the compounds in beauty and food |
| FR2798667A1 (en) * | 1999-09-22 | 2001-03-23 | Pharmascience Lab | PROCESS FOR EXTRACTING POLYHYDROXYL FATTY COMPOUNDS AND POLYHYDROXYL FATTY ALCOHOLS, COMPOSITION THEREOF AND USE THEREOF IN THERAPEUTICS, COSMETICS AND FOOD |
| US7371420B2 (en) | 2002-07-29 | 2008-05-13 | Laboratoires Expanscience | Method for producing an avocado unsaponifiable rich in furan lipids |
| WO2004012496A2 (en) * | 2002-07-29 | 2004-02-12 | Laboratoires Expanscience | Method for producing an avocado unsaponifiable rich in furan lipids |
| WO2004016106A1 (en) * | 2002-07-29 | 2004-02-26 | Laboratoires Expanscience | Method for producing an unsaponifiable matter of avocado rich in furan lipids |
| WO2004012496A3 (en) * | 2002-07-29 | 2004-04-08 | Expanscience Lab | Method for producing an avocado unsaponifiable rich in furan lipids |
| WO2005117856A1 (en) * | 2004-05-28 | 2005-12-15 | Laboratoires Expanscience | Use of furan alkyl for preparing an antidiabetic drug |
| US7589121B2 (en) | 2004-05-28 | 2009-09-15 | Laboratoires Expanscience | Use of furan alkyls for preparing a drug for treating obesity and cosmetically treating overweight |
| CN1960722B (en) * | 2004-05-28 | 2010-09-08 | 科学发展实验室 | Use of furan alkyl for preparing an antidiabetic drug |
| US7872043B2 (en) | 2004-05-28 | 2011-01-18 | Laboratories Expanscience | Use of furan alkyls for a cellulite cosmetic treatment |
| FR2870742A1 (en) * | 2004-05-28 | 2005-12-02 | Expanscience Laboratoires Sa | USE OF ALKYL FURANS FOR THE PREPARATION OF A MEDICAMENT FOR THE TREATMENT OF DIABETES, OBESITY AND FOR THE COSMETIC TREATMENT OF CELLULITE AND OVERLOAD |
| US8859617B2 (en) | 2004-05-28 | 2014-10-14 | Laboratoires Expanscience | Use of furan alkyl for preparing an antidiabetic drug |
| JP2016515585A (en) * | 2013-03-29 | 2016-05-30 | アボサイエンス、リミテッド、ライアビリティー、カンパニーＡｖｏｓｃｉｅｎｃｅ， Ｌｌｃ | Lipid furan, pyrrole and thiophene compounds for the treatment of cancer, neurological disorders and fibrotic disorders |
| US10085962B2 (en) | 2013-03-29 | 2018-10-02 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for treatment of cancer, neurological disorders, and fibrotic disorders |
| US10525031B2 (en) | 2013-03-29 | 2020-01-07 | Avoscience, Llc | Lipid furan, pyrrole, and thiophene compounds for treatment of cancer, neurological disorders, and fibrotic disorders |
| US11058663B2 (en) | 2013-03-29 | 2021-07-13 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for treatment of cancer, neurological disorders, and fibrotic disorders |
| US11833129B2 (en) | 2013-03-29 | 2023-12-05 | Avoscience, Llc | Thiophene compound for treatment of exfoliating glaucoma |
| US10905673B2 (en) | 2016-04-27 | 2021-02-02 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for use in the treatment of atrophic vaginitis |
| US11602518B2 (en) | 2016-04-27 | 2023-03-14 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for use in the treatment of atrophic vaginitis |
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|---|---|
| FR2678614B1 (en) | 1995-03-03 |
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