WO1993003005A1 - Compose d'alcanamidoammonium - Google Patents

Compose d'alcanamidoammonium Download PDF

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Publication number
WO1993003005A1
WO1993003005A1 PCT/JP1992/001014 JP9201014W WO9303005A1 WO 1993003005 A1 WO1993003005 A1 WO 1993003005A1 JP 9201014 W JP9201014 W JP 9201014W WO 9303005 A1 WO9303005 A1 WO 9303005A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
group
compound
solvent
carbon atoms
Prior art date
Application number
PCT/JP1992/001014
Other languages
English (en)
Japanese (ja)
Inventor
Sadakazu Yokomori
Yuki Takahashi
Yoko Misawa
Taro Matsumoto
Katsuo Hatayama
Original Assignee
Taisho Pharmaceutical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Taisho Pharmaceutical Co., Ltd. filed Critical Taisho Pharmaceutical Co., Ltd.
Priority to AU24027/92A priority Critical patent/AU656625B2/en
Priority to CN93101376A priority patent/CN1082534A/zh
Publication of WO1993003005A1 publication Critical patent/WO1993003005A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to an alkane ammonium compound having a hair growth action.
  • the purpose of the present invention is to provide a compound having a new type of hair growth action.
  • the invention relates to the formula
  • R 1 represents an alkyl group having 1 to 22 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms
  • R 2 represents an alkylene group having 1 to 15 carbon atoms
  • R e represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • R represents an alkylene group having 2 to 10 carbon atoms
  • R 6 and R 6 are the same or different and have 1 to 5 carbon atoms.
  • R 7 represents an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an ⁇ alkyl group having 1 to 5 carbon atoms substituted with a phenyl group ''
  • A is an oxygen atom or a formula
  • n represents a group represented by.> Represents an integer of 0 to 2
  • X m _ is shown an anion
  • m represents an integer corresponding to the number of charges of the anion in X.
  • an alkyl group having 1 to 22 carbon atoms means a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, isohexyl, n-hexyl, n-octyl, n-nonyl, n-decyl, n —Pindecyl group, n-decyl group, n-tridecyl group, n-tetradecyl group, n — ⁇ antadecyl group, n-hexadecyl group, n-hexadecyl group, n-octade
  • the cycloalkyl group having 3 to 8 carbon atoms includes a cyclobutyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cyclooctyl group, and the like.
  • C1-C5 alkylene group means a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an octamethylene group, a nonamethylene group, a decamethylene group, a pendecamethylene group, or a dodecamethylene group.
  • Linear groups such as styrene, tridecamethylene, pentadecamethylene, propylene, 1-methyl-trimethylene, 2,2-dimethyl-trimethylene, 1-methyl-hexamethylene, ethylidene, propylidene, and butylidene Or branched.
  • An alkyl group having 1 to 5 carbon atoms means a linear or branched chain such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group and n-pentyl group. Refers to an alkyl group.
  • An alkylene group having 2 to 10 atoms means an alkylene group having 1 to 1 carbon atoms and an alkylene group having 1 to 5 carbon atoms having 2 to 10 carbon atoms.
  • the alkenyl group having 2 to 10 carbon atoms includes a vinyl group, an aryl group, a 1-butynyl group, a brenyl group, a geranyl group and the like.
  • An alkyl group having 1 to 5 carbon atoms substituted with a phenyl group is a benzyl group, It is a linear or branched alkyl group substituted with a phenyl group such as a phenylethyl group or a phenylbrobyl group.
  • X represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, sulfuric acid, nitric acid, nitrous acid, methyl sulfate, methyl sulfate, dimethyl phosphate, methanesulfonic acid, benzenesulfonic acid, p-toluene
  • examples thereof include anions such as sulfonic acid, formic acid, acetic acid, brobionic acid, glycolic acid, lactic acid, oxalic acid, benzoic acid, and salicylic acid.
  • the compound of the present invention can be produced, for example, according to the following method (hereinafter, R 1 , R 2 , R s , R 4 , RS, Re , R 7 , A and n are particularly Unless otherwise specified, it is used as defined above.)
  • the compound represented by R can be obtained.
  • amide-forming reaction ordinary amide-forming reaction conditions can be applied.
  • a method of dehydration by heating (b) an acid halide method, (c) a mixed acid anhydride method, (d) an active ester method, and (e) a carpoimide method can be used. It is preferable to use the method a> or (b).
  • the method (b) is a method in which an acid halide obtained by reacting a compound of the formula ( ⁇ ) with a halogenating agent and a compound of the formula (F) are reacted with the compound of the formula ( ⁇ ) in an equimolar amount.
  • a halogenating agent e.g., thionyl chloride, phosphorus pentachloride, oxychlorine, oxalyl chloride, thionyl bromide, phosphorus tribromide, etc.
  • a solvent-free or inert solvent e.g., benzene, In toluene, tetrahydrofuran, salted methylene, chloroform, etc.
  • the compound of B is used without solvent or in a solvent (e.g., halogenated hydrocarbons such as methylene chloride, ⁇ -form, carbon tetrachloride, ethers such as ethyl ether, tetrahydrofuran, dioxane, benzene,In the presence of aromatic hydrocarbons such as benzene and xylene, esters such as methyl acetate and ethyl acetate, and non-brotonic polar solvents such as N, N-dimethylformamide and dimethyl sulfoxide).
  • a solvent e.g., halogenated hydrocarbons such as methylene chloride, ⁇ -form, carbon tetrachloride, ethers such as ethyl ether, tetrahydrofuran, dioxane, benzene,In the presence of aromatic hydrocarbons such as benzene and xylene, esters such as methyl acetate and
  • the reaction is carried out at about L 0 ° C (preferably 0 to 50.C)
  • the first half reaction does not necessarily require a catalyst, but pyridine, triethylamine, N, N
  • the reaction can be promoted by adding dimethylformamide or the like to the catalyst in an amount of from 1 to equimolar.
  • a compound of the present invention can be obtained by a quaternization reaction in which an acid ester having R 7 is reacted with or without a solvent. it can.
  • the halogen atom is a chlorine atom, a bromine atom or an iodine atom.
  • the above acid ester refers to a mineral acid ester (eg, dimethyl sulfate, methyl sulfate, trimethyl phosphate, etc.) or an organic acid ester (eg, methyl methanesulfonate, methyl benzenesulfonate, ⁇ -toluenesulfonic acid) Methyl, pentyl ⁇ -toluenesulfonate, etc.
  • x °-represents a carboxylic acid for example, formic acid, dicarboxylic acid, Bionic acid, glycolic acid, lactic acid, oxalic acid, benzoic acid, salicylic acid, etc.> can also be produced by the following method.
  • the compound of the present invention produced by the method described above is dissolved in a solvent, and various forms thereof (for example, formic acid form, acetic acid form, brobionic acid form, glycolic acid form, lactic acid form, oxalic acid form, benzoic acid) And salicylic acid form) by ion exchange with an ion exchange resin.
  • solvent water, alcohols (eg, methanol, ethanol, and the like), a mixed solvent thereof and the like can be used.
  • ⁇ is a group of the formula (II), and n is 1 or 2.
  • the compound of the formula (V) obtained by the above method (where A is a group of the formula>) And then reacting it with a 1 to 3 molar amount of acid reagent in a solvent, followed by a reaction in the same manner as in jlfi.
  • oxidizing agent hydrogen peroxide, organic peracid (for example, peracetic acid, trifluoroperacetic acid, perbenzoic acid, perphthalic acid, m-chloroperbenzoic acid, etc.) can be used.
  • organic peracid for example, peracetic acid, trifluoroperacetic acid, perbenzoic acid, perphthalic acid, m-chloroperbenzoic acid, etc.
  • solvent water, methylene chloride, chloroform, dichloroethane, benzene, toluene, ethyl acetate, acetic acid, and the like can be used.
  • Anti ⁇ degree one 3 0 an I 5 0 e C.
  • X B _ fluorine atoms in the formula (I>, a chlorine atom, a bromine atom, sulfuric, nitric acid, compounds nitrite anions Ru can be produced even cowpea the next 3 ⁇ 4 method.
  • a silver salt that ion-exchanges with iodine ions (silver fluoride, silver chloride, Silver bromide, silver sulfate, silver nitrate or silver nitrite) in a solvent at room temperature to the boiling point of the solvent, whereby in formula (1), X "-is a fluorine atom, a chlorine atom, a bromine atom, a sulfuric acid, a nitric acid, Compounds that are anions of nitrous acid can be obtained.
  • solvent water, alcohols (eg, methanol, ethanol, and the like), a mixed solvent thereof and the like can be used.
  • the compound of the formula (m) as a starting material can be produced from a known compound by the following method. '
  • Z 1 represents a halogen atom.
  • a compound of the formula (BI), which is a group of I) and wherein n is 0, can be obtained.
  • the halogen atom is a chlorine atom, a bromine atom or an iodine atom.
  • sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine and the like can be used.
  • the solvent include water, alcohols (eg, methanol, ethanol, etc.), acetone, N'N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran and the like.
  • a reaction accelerator such as potassium iodide can be added.
  • oxidizing agents include hydrogen peroxide and organic peracids (eg, peracetic acid, trifluoroacetic acid). Oral peracetic acid, perbenzoic acid, perphthalic acid, m-chloroperbenzoic acid, etc.) can be used.
  • organic peracids eg, peracetic acid, trifluoroacetic acid.
  • solvent water, methylene chloride, chloroform, dichloroethane, benzene, toluene, ethyl acetate, acetic acid, and the like can be used. Reaction temperature is 30 ⁇ : L50. C.
  • Z 2 represents a halogen atom.
  • the mixture is stirred at 0 to the boiling point of the solvent for 1 to 48 hours to obtain a compound represented by the formula (I) wherein A is an oxygen atom. ) Can be obtained.
  • the halogen atom is a chlorine atom, a bromine atom or an iodine atom.
  • the base include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, sodium amide, triethylamine, barium oxide, silver oxide and the like.
  • the solvent water, acetone, ether, tetrahydrofuran, N, N-dimethylformamide, dimethylsulfoxide, 1,2-dimethyloxetane, acetonitrile, dioxane and the like can be used. Further, a reaction accelerator such as potassium iodide may be added.
  • Z 8 and Z 4 are the same or different and represent a halogen atom.
  • a compound for example, water, acetone, ether, tetrahydrofuran, N, N-dimethyl
  • solvent ether, as tetrahydrofuran etc.
  • the compound of formula (BO) in which A is an oxygen atom can also be obtained by reacting with medium and magnesium to form a Grignard reagent and then reacting with carbon dioxide.
  • the halogen atom is a chlorine atom, a bromine atom or an iodine atom.
  • the bases include sodium hydroxide, sodium hydroxide, sodium carbonate, and carbonic acid.
  • lithium, sodium hydrogen hydride, sodium amide, triethylamine, barium oxide, silver sulfide, and the like can be used.
  • Z 6 represents a halogen atom.
  • a compound represented by the formula for example, sodium hydroxide, sodium hydroxide, sodium carbonate, carbonic acid, sodium hydrogenamide, sodium hydroxide, sodium amide) , Triethylamine, barium oxide, silver oxide, etc.
  • a solvent eg, water, acetone, ether, tetrahydrofuran, N, N-dimethylformamide, dimethylsulfoxide, 1,2-dimethyloxetane.
  • the halogen atom is a chlorine atom, a bromine atom or an iodine atom.
  • the hydrolysis is carried out by stirring in a solvent at room temperature to the boiling point of the solvent for 1 to 12 hours in the presence of an acid or a base.
  • hydrochloric acid, sulfuric acid, acetic acid, formic acid and the like can be used as the acid
  • sodium hydroxide, hydrating hydroxide, barium hydroxide and the like can be used as the base.
  • water and hydrous alcohols eg, aqueous methanol solution, aqueous ethanol solution, etc.
  • the dosage and administration method of the compound of the formula (I) are as follows.
  • One or more of the compounds of the formula (I) can be prepared by using, for example, a conventional base in lotions, emulsions, creams, gels, aerosols and the like.
  • An external preparation is applied several times a day to the scalp in an appropriate amount. Further, other medicinal substances can be added to this preparation.
  • the usual bases and other medicinal substances in the above include, for example, solvents (ethyl alcohol, isobutyl propyl alcohol, 1,3-butylene glycol, 1,4-butylene glycol, propylene glycol, dibrovirene glycol, glycerin, Diglycerin, polyethylene glycol, purified water, etc.)
  • solvents ethyl alcohol, isobutyl propyl alcohol, 1,3-butylene glycol, 1,4-butylene glycol, propylene glycol, dibrovirene glycol, glycerin, Diglycerin, polyethylene glycol, purified water, etc.
  • Mucopolysaccharides hyaluronic acid, chondroitin-mono-sulfate, chondroitin-6-sulfate, dermatan sulfate, keratan sulfate, heparan sulfate, polysulfonate of chondroitin sulfate, etc.
  • vitamin E acetate>, oil (liquid paraffin, white color petrolatum, solid paraffin, Ceresin, microcrystalline wax, cholesterol, squalane, olive oil, rosehip oil, mink oil, jojoba oil, hydrogenated castor oil, hydrogenated coconut oil, isoprovir myristate, ethyl carbylate, ethyl ethyl brurilate, 'Lumithreic acid, ethyl palmitoleate, ethyl linoleate, ethyl linolenate, oleic acid, stearic acid, linoleic acid, linolenic acid, palmitic acid, behenic acid, lauric acid, stearyl alcohol., Cety
  • Non-ionic surfactants polyoxyethylene fatty acid ester ⁇ ⁇ polyoxyethylene sorbitan fatty acid ester ⁇ sorbitan fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester , Polyglycerin alkyl phenyl ether, polyoxyethylene hydrogenated castor oil, copolymer of polyoxyethylene and poly (propylene glycol)>, anionic surfactant (N-A Silamino acid salt, N-acyl sarcosine salt, alkyl phosphate ester salt, acyl methyl taurine salt, etc.), and cationic surfactants (alkyl trimethyl ammonium, alkyl mono N, N-dialkylamino acetate, etc.) ), Amphoteric surfactants (imidazoline, aminoxide, etc.), polymeric surfactants (casein
  • Anti-inflammatory drugs such as camphor
  • anti-inflammatory drugs such as glycyrrhetinic acid, dipotassium glycyrrhizinate, chlorodine berberine, shikonin, guaiazulene, allantoin, S-aminocabronic acid, etc.
  • Minoxidil diazoxide, capsicum extract, capsaicin, salted carpronium, etc.
  • corticosteroids such as hydrocortisone acetate, betamethasone valerate, etc.
  • antihistamines such as diphenhydramine hydrochloride, isothibenzyl hydrochloride
  • local anesthetics Dibuforce hydrochloride, lidocaine hydrochloride, etc.
  • keratolytic agent urine, salicylic acid, etc.
  • keratinizing agent [Vitamin A acid and its derivatives (eg, 13
  • the test for the scalpel effect of alkanamide compounds was carried out using five C3H mice (male, 7 weeks old) as a group, the back hair of which was shaved with clippers once a day, and shown in Table 1 once a day. Then, 0.2 ml of the obtained sample was applied for 10 days, and the degree of hair growth thereafter was visually evaluated in the following seven stages.
  • Table 2 shows the results 42 days after the start of sample application as the average value of the evaluation points.
  • Table 1 Sample No. Compound name
  • the compound of the present invention has an excellent hair growth action, it is useful as a hair growth agent,

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

L'invention se rapporte à un composé d'alcanamidoammonium, représenté par la formule générale (I), qui possède d'excellentes propriétés trichogéniques. Dans la formule (I), R1 représente alkyle ou cycloalkyle; R2 représente alkylène; R3 représente hydrogène ou alkyle; R4 représente alkylène; R5 et R6, qui peuvent être identiques ou différents entre eux, représentent chacun alkyle; R7 représente alkyle, alcényle ou phénylalkyle; A représente oxygène ou -S(O)¿n?- où n représente un nombre entier compris entre 0 et 2; X?m-¿ représente un anion; et m représente un nombre entier correspondant au nombre de charges se trouvant sur l'anion de X.
PCT/JP1992/001014 1991-08-10 1992-08-07 Compose d'alcanamidoammonium WO1993003005A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU24027/92A AU656625B2 (en) 1991-08-10 1992-08-07 Alkanamidoammonium compound
CN93101376A CN1082534A (zh) 1991-08-10 1993-02-10 烷酰氨基铵化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP3/287374 1991-08-10
JP3287374A JPH0543529A (ja) 1991-08-10 1991-08-10 アルカンアミドアンモニウム化合物

Publications (1)

Publication Number Publication Date
WO1993003005A1 true WO1993003005A1 (fr) 1993-02-18

Family

ID=17716536

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1992/001014 WO1993003005A1 (fr) 1991-08-10 1992-08-07 Compose d'alcanamidoammonium

Country Status (5)

Country Link
JP (1) JPH0543529A (fr)
CN (1) CN1082534A (fr)
AU (1) AU656625B2 (fr)
CA (1) CA2115345A1 (fr)
WO (1) WO1993003005A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5610198A (en) * 1994-03-18 1997-03-11 The United States Of America As Represented By The Department Of Health And Human Services Anti-mycobacterial compositions and their use for the treatment of tuberculosis and related diseases
WO1999056722A1 (fr) * 1998-05-07 1999-11-11 Ceca S.A. Derives d'acides alpha carboxyliques (aha)
EP0965583A1 (fr) * 1998-06-15 1999-12-22 Transgene S.A. Composés de polyamine et compositions les contenant, utiles pour le transfert de substances actives dans des cellules
EP0965584A3 (fr) * 1998-06-15 2003-12-17 Transgene S.A. Composés de polyamine et compositions les contenant, utiles pour le transfert de substances actives dans des cellules

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8741966B2 (en) 2007-11-09 2014-06-03 Pronova Biopharma Norge As Lipid compounds for use in cosmetic products, as food supplement or as a medicament
EP2147910A1 (fr) * 2008-07-15 2010-01-27 Pronova BioPharma Norge AS Nouveaux composés lipidiques
AR078507A1 (es) 2009-05-08 2011-11-16 Pronova Biopharma Norge As Compuestos lipidicos, composiciones farmaceuticas, usos y metodo de preparacion
SG10201509127YA (en) 2010-11-05 2015-12-30 Pronova Biopharma Norge As Methods of treatment using lipid compounds
AR094941A1 (es) 2013-02-28 2015-09-09 Olaf Hustvedt Svein Una composición que comprende un compuesto lipídico, un triglicérido y un tensioactivo, y métodos para usarla
CN107530306A (zh) 2015-04-28 2018-01-02 普罗诺瓦生物医药挪威公司 结构增强的含硫脂肪酸在预防和/或治疗非酒精性脂肪性肝炎中的用途
AU2018381124B2 (en) 2017-12-06 2024-06-27 Basf As Fatty acid derivatives for treating non-alcoholic steatohepatitis

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5019719A (fr) * 1973-06-27 1975-03-01
JPS54130509A (en) * 1977-06-29 1979-10-09 Procter & Gamble Organism decomposing cationic surfactant

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5019719A (fr) * 1973-06-27 1975-03-01
JPS54130509A (en) * 1977-06-29 1979-10-09 Procter & Gamble Organism decomposing cationic surfactant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5610198A (en) * 1994-03-18 1997-03-11 The United States Of America As Represented By The Department Of Health And Human Services Anti-mycobacterial compositions and their use for the treatment of tuberculosis and related diseases
WO1999056722A1 (fr) * 1998-05-07 1999-11-11 Ceca S.A. Derives d'acides alpha carboxyliques (aha)
FR2778405A1 (fr) * 1998-05-07 1999-11-12 Ceca Sa N-(dialkylamino) alkyl alpha carboxamides, compositions les contenant, procedes de preparation et utilisations
EP0965583A1 (fr) * 1998-06-15 1999-12-22 Transgene S.A. Composés de polyamine et compositions les contenant, utiles pour le transfert de substances actives dans des cellules
EP0965584A3 (fr) * 1998-06-15 2003-12-17 Transgene S.A. Composés de polyamine et compositions les contenant, utiles pour le transfert de substances actives dans des cellules

Also Published As

Publication number Publication date
JPH0543529A (ja) 1993-02-23
AU2402792A (en) 1993-03-02
CN1082534A (zh) 1994-02-23
AU656625B2 (en) 1995-02-09
CA2115345A1 (fr) 1993-02-18

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