FR2678614A1 - Compose presentant une activite en tant qu'inhibiteur de la collagenase et medicament le contenant. - Google Patents
Compose presentant une activite en tant qu'inhibiteur de la collagenase et medicament le contenant. Download PDFInfo
- Publication number
- 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
- Authority
- FR
- France
- Prior art keywords
- compounds
- furanyl
- formula
- oil
- compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 239000003814 drug Substances 0.000 title claims abstract description 7
- 239000002442 collagenase inhibitor Substances 0.000 title abstract description 4
- 101000645291 Bos taurus Metalloproteinase inhibitor 2 Proteins 0.000 title abstract description 3
- 229940122097 Collagenase inhibitor Drugs 0.000 title abstract description 3
- 101000669513 Homo sapiens Metalloproteinase inhibitor 1 Proteins 0.000 title abstract description 3
- 102100039364 Metalloproteinase inhibitor 1 Human genes 0.000 title abstract description 3
- 230000000694 effects Effects 0.000 title description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 235000013399 edible fruits Nutrition 0.000 claims description 2
- 238000000199 molecular distillation Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- FHTSIFHJYGMMMD-UHFFFAOYSA-N [C]1=CC=CO1 Chemical compound [C]1=CC=CO1 FHTSIFHJYGMMMD-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000002243 precursor Substances 0.000 description 6
- 244000025272 Persea americana Species 0.000 description 4
- 235000008673 Persea americana Nutrition 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 235000021302 avocado oil Nutrition 0.000 description 3
- 239000008163 avocado oil Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 102000055008 Matrilin Proteins Human genes 0.000 description 2
- 108010072582 Matrilin Proteins Proteins 0.000 description 2
- 102000016611 Proteoglycans Human genes 0.000 description 2
- 108010067787 Proteoglycans Proteins 0.000 description 2
- 210000001612 chondrocyte Anatomy 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 210000002808 connective tissue Anatomy 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 235000021022 fresh fruits Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 101710107427 Extracellular metalloprotease Proteins 0.000 description 1
- 101710200557 Extracellular small neutral protease Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000001188 articular cartilage Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 108010054626 proteoglycan-degrading metalloendopeptidases Proteins 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- -1 terpene alcohols Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9108303A FR2678614A1 (fr) | 1991-07-03 | 1991-07-03 | Compose presentant une activite en tant qu'inhibiteur de la collagenase et medicament le contenant. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9108303A FR2678614A1 (fr) | 1991-07-03 | 1991-07-03 | Compose presentant une activite en tant qu'inhibiteur de la collagenase et medicament le contenant. |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2678614A1 true FR2678614A1 (fr) | 1993-01-08 |
FR2678614B1 FR2678614B1 (enrdf_load_stackoverflow) | 1995-03-03 |
Family
ID=9414656
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR9108303A Granted FR2678614A1 (fr) | 1991-07-03 | 1991-07-03 | Compose presentant une activite en tant qu'inhibiteur de la collagenase et medicament le contenant. |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2678614A1 (enrdf_load_stackoverflow) |
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 (fr) * | 1998-04-29 | 1999-11-04 | Laboratoires Pharmascience | Nouveaux composes extraits d'huile vegetale utilisables dans l'industrie pharmaceutique et cosmetique, notamment pour l'inhibition de la croissance cellulaire |
FR2798667A1 (fr) * | 1999-09-22 | 2001-03-23 | Pharmascience Lab | Procede d'extraction des composes furaniques et alcools gras polyhydroxyles de l'avocat, composition a base de et utilisation de ces composes en therapeutique, cosmetique et alimentaire |
WO2004016106A1 (fr) * | 2002-07-29 | 2004-02-26 | Laboratoires Expanscience | Procede d'obtention d'un insaponifiable d'avocat riche en lipides furaniques |
FR2870742A1 (fr) * | 2004-05-28 | 2005-12-02 | Expanscience Laboratoires Sa | Utilisation d'alkyle furannes pour la preparation d'un medicament destine au traitement du diabete, de l'obesite et pour le traitement cosmetique de la cellulite et de la surcharge ponderale |
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 (ja) * | 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 | 癌、神経障害及び線維性障害の治療のための、脂質フラン、ピロール及びチオフェン化合物 |
US10905673B2 (en) | 2016-04-27 | 2021-02-02 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for use in the treatment of atrophic vaginitis |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1425343A (en) * | 1972-02-14 | 1976-02-18 | Unilever Ltd | Phthalic acid derivatives |
-
1991
- 1991-07-03 FR FR9108303A patent/FR2678614A1/fr 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)
Title |
---|
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 (24)
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 (fr) * | 1998-04-29 | 1999-11-04 | Laboratoires Pharmascience | Nouveaux composes extraits d'huile vegetale utilisables dans l'industrie pharmaceutique et cosmetique, notamment pour l'inhibition de la croissance cellulaire |
FR2778181A1 (fr) * | 1998-04-29 | 1999-11-05 | Pharmascience Lab | Nouveaux composes extraits d'huile vegetale utilisables dans l'industrie pharmaceutique et cosmetique,notamment pour l'inhibition de la croissance cellulaire |
FR2798667A1 (fr) * | 1999-09-22 | 2001-03-23 | Pharmascience Lab | Procede d'extraction des composes furaniques et alcools gras polyhydroxyles de l'avocat, composition a base de et utilisation de ces composes en therapeutique, cosmetique et alimentaire |
WO2001021605A3 (fr) * | 1999-09-22 | 2001-10-25 | Pharmascience Lab | Procede d'extraction des composes lipides furaniques et alcools gras polyhydroxyles de l'avocat, composition a base de ces composes et leur utilisation en therapeutique, cosmetique et alimentaire |
JP2003509506A (ja) * | 1999-09-22 | 2003-03-11 | ラボラトワール ファルマシアンス | アボガドのフラン脂質化合物およびポリヒドロキシル化された脂肪族アルコールを抽出する方法、該化合物に基く組成物および治療、美容並びに食品における該化合物の使用 |
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 (ja) * | 1999-09-22 | 2012-09-12 | ラボラトワール エクスパンシアンス | アボガドのフラン脂質化合物およびポリヒドロキシル化された脂肪族アルコールを抽出する方法、該化合物に基く組成物および治療、美容並びに食品における該化合物の使用 |
US7371420B2 (en) | 2002-07-29 | 2008-05-13 | Laboratoires Expanscience | Method for producing an avocado unsaponifiable rich in furan lipids |
WO2004016106A1 (fr) * | 2002-07-29 | 2004-02-26 | Laboratoires Expanscience | Procede d'obtention d'un insaponifiable d'avocat riche en lipides furaniques |
WO2004012496A3 (fr) * | 2002-07-29 | 2004-04-08 | Expanscience Lab | Procede d'obtention d'un insaponifiable d'avocat riche en lipides furaniques |
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 |
WO2005117856A1 (fr) * | 2004-05-28 | 2005-12-15 | Laboratoires Expanscience | Utilisation d’alkyle furannes pour la preparation d’un medicament destine au traitement du diabete |
CN1960722B (zh) * | 2004-05-28 | 2010-09-08 | 科学发展实验室 | 烷基呋喃在制备抗糖尿病药物中的用途 |
US7872043B2 (en) | 2004-05-28 | 2011-01-18 | Laboratories Expanscience | Use of furan alkyls for a cellulite cosmetic treatment |
FR2870742A1 (fr) * | 2004-05-28 | 2005-12-02 | Expanscience Laboratoires Sa | Utilisation d'alkyle furannes pour la preparation d'un medicament destine au traitement du diabete, de l'obesite et pour le traitement cosmetique de la cellulite et de la surcharge ponderale |
US8859617B2 (en) | 2004-05-28 | 2014-10-14 | Laboratoires Expanscience | Use of furan alkyl for preparing an antidiabetic drug |
JP2016515585A (ja) * | 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 | 癌、神経障害及び線維性障害の治療のための、脂質フラン、ピロール及びチオフェン化合物 |
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 |
Also Published As
Publication number | Publication date |
---|---|
FR2678614B1 (enrdf_load_stackoverflow) | 1995-03-03 |
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