WO1989006643A1 - ACIDE n-CHLOROPHENOXYISOBUTIRIQUE D'ETHER UNDECYLIQUE ET PREPARATION PHARMACEUTIQUE LE CONTENANT POUR TRAITER L'HYPERLIPEMIE - Google Patents

ACIDE n-CHLOROPHENOXYISOBUTIRIQUE D'ETHER UNDECYLIQUE ET PREPARATION PHARMACEUTIQUE LE CONTENANT POUR TRAITER L'HYPERLIPEMIE Download PDF

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Publication number
WO1989006643A1
WO1989006643A1 PCT/SU1988/000019 SU8800019W WO8906643A1 WO 1989006643 A1 WO1989006643 A1 WO 1989006643A1 SU 8800019 W SU8800019 W SU 8800019W WO 8906643 A1 WO8906643 A1 WO 8906643A1
Authority
WO
WIPO (PCT)
Prior art keywords
per
ether
acid
undecylic
pharmaceutical preparation
Prior art date
Application number
PCT/SU1988/000019
Other languages
English (en)
Russian (ru)
Inventor
Lev Natanovich Volovelsky
Valery Vladimirovich Natarov
Ivan Sergeevich Chekman
Viktor Andreevich Tumanov
Vitaly Ignatievich Zapadnjuk
Nadezhda Vasilievna Popova
Vera Nikolaevna Shneur
Sergei Alexandrovich Korotkov
Original Assignee
Kharkovsky Nauchno-Issledovatelsky Institut Endokr
Kievsky Meditsinsky Institut Imeni Akademika A.A.B
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 Kharkovsky Nauchno-Issledovatelsky Institut Endokr, Kievsky Meditsinsky Institut Imeni Akademika A.A.B filed Critical Kharkovsky Nauchno-Issledovatelsky Institut Endokr
Priority to JP63503721A priority Critical patent/JPH02502998A/ja
Priority to DE883891219T priority patent/DE3891219T1/de
Priority to GB8920466A priority patent/GB2221681A/en
Priority to PCT/SU1988/000019 priority patent/WO1989006643A1/fr
Priority to FR888805868A priority patent/FR2630736B1/fr
Publication of WO1989006643A1 publication Critical patent/WO1989006643A1/fr
Priority to SE8903047A priority patent/SE8903047L/xx

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07C69/708—Ethers
    • C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07C69/73—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 unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the growing invention is not available for organic chemistry, and more specifically, for the new substance and the treatment of non-chronic drug-related diseases.
  • the indicated product is sufficiently large, which makes its use limited.
  • v ⁇ ) - 0 of the indicated product is 1.0 g / kg of live weight. He takes possession of the undesirable harmful effects on the liver, kidneys.
  • heme which, according to the invention, a new compound, undecyl ether and a butyric acid, has the following formula:
  • the claimed medication may be used in various medicinal formulations. It is preferable to use the claimed product in the form of a tablet.
  • the claimed product in the form of a tablet contains an active substance
  • the drug is optionally available in the amount of 0.001-0.003 g per one tablet.
  • the claimed preparation is practically not toxic. It is easy to switch to 15 times less than the toxicity of a bulk appliance. He does not possess harmful actions. Otherwise, the dose of the claimed product is the same as the one given with the use of a therapeutic unit.
  • the inventive compound is undecyl ether ⁇ -malic acid, which supplies a dense, colorless liquid that boils 52 ° C to 5 ° C. This elemental analysis of the consortium computes.
  • the claimed compound is obtained by heating an undecyl syrup with ⁇ -hydroxybutyric acid or with halide anhydrous acid
  • the claimed compound is hyperactive and ideally active and is an active treatment for the treatment of hyperlipidemia.
  • the specific activity of the claimed compounds was studied using two species of living (krukliky, kryssy) using
  • the research methodology was as follows. For the first time, they entered the enterprise (closed or claimed connection) for 10 days. Then, one day inside , they entered the city of Sh-. ⁇ 339. The animals were taken away after 4 hours. They introduced a lively animal
  • hypolipidemic antivirality of the claimed compounds and the affection of hyperlipidemia was studied.
  • ⁇ win-80 ⁇ intramuscular 2.0 mg / kg body weight of live animals.
  • ⁇ win-80 after 12 hours after injection, it contributes to 1.5-2.5 times an increase in total lipids, cholesterol, beta-lipids, and glycerides.
  • Triton 300 mg / kg internal, single, single
  • the simple toxicity of the claimed compounds was studied on two species of live animals: white mice weighing 16–20 g, 5–5 saxes of 200–240 g, with both intrinsic and parenteral administration.
  • the simple toxicity of the claimed compounds in the form of a table was studied using white mice and bulk rats with the intrinsic introduction.
  • white mice a suspension of the claimed drug was injected into the stomach with a syringe. Surveillance of live 10 people took 12 days.
  • the inventive drug was administered at a conditionally therapeutic (164 mg per kg body weight) and conditionally toxic (820 mg per kg body weight) dose.
  • the studied indices were divided after I, 3, and 6 months. - When studying the toxicity of the claimed drug, the following results were obtained. There are no other differences in the mass of the body of non-living animals and have been reported for 6 months.
  • P ⁇ vedennye issled ⁇ vaniya ⁇ azali, ch ⁇ ⁇ e ⁇ a ⁇ a ⁇ claimed in ⁇ imenenny ⁇ d ⁇ za ⁇ not ⁇ azyvae ⁇ susches ⁇ venn ⁇ g ⁇ impact on ⁇ liches ⁇ v ⁇ e ⁇ i ⁇ tsi ⁇ v, ley ⁇ tsi ⁇ v, z ⁇ zin ⁇ - ⁇ il ⁇ v, apel ⁇ il ⁇ v, ney ⁇ il ⁇ v, lim ⁇ tsi ⁇ v, m ⁇ n ⁇ tsi ⁇ v, u ⁇ ven gem ⁇ gl ⁇ bina and s ⁇ s ⁇ ⁇ sedaniya e ⁇ i ⁇ tsi ⁇ v.
  • the claimed method does not change the amount of respiratory movement and does not change the level of arterial pressure in the population.
  • P ⁇ vedennye issled ⁇ vaniya ⁇ yzucheniyu mu ⁇ agenny ⁇ 5 sv ⁇ ys ⁇ v zayavlyaem ⁇ g ⁇ ⁇ e ⁇ a ⁇ a ⁇ a svide ⁇ els ⁇ v ⁇ vali, ch ⁇ ⁇ n not indutsi ⁇ ue ⁇ mu ⁇ atsii ⁇ an in s ⁇ ma ⁇ iches ⁇ i ⁇ ⁇ le ⁇ na ⁇ vz ⁇ s- ly ⁇ zhiv ⁇ ny ⁇ , ⁇ an and s ⁇ ma ⁇ iches ⁇ i ⁇ nle ⁇ na ⁇ za ⁇ dyshey, yavlyayuschi ⁇ sya b ⁇ lee chuvs ⁇ vi ⁇ elnymi ⁇ is ⁇ y ⁇ uem ⁇ mu agen ⁇ u. Carcinogenic Activity Tests
  • Tests of the claimed drug preparation for the immune system were carried out. The results of the tests showed that the claimed drug did not have an immuno-modulating effect on the body in respect to the immune system, and so on. When researching a locally disturbing
  • the product does not have any local irritating or allergenic properties.
  • the level at the time of the release is stated in the preparation and administration to the stomach at a dose of 164 mg per ng of body weight
  • the inventive lense preparation employs a variety of 5 personal medications, such as tablets, yellow capsules, even aerosols.
  • the claimed product is in a tablet of 0.05 g, and is mainly suitable for sublingual use.
  • the claimed product does not have any indications of change and does not have a harmful effect.
  • Za ⁇ em ⁇ i e ⁇ y same ⁇ em ⁇ e ⁇ a ⁇ u ⁇ e ⁇ e- a ⁇ tsi ⁇ nnuyu weight ⁇ e ⁇ emeshivayu ⁇ in Götschen 3 chas ⁇ v, ⁇ sle cheg ⁇ mixture ⁇ azbavlyayu ⁇ 500 ma and benz ⁇ la ⁇ as ⁇ v ⁇ ⁇ my- 5 vayu ⁇ 200 ml of 10% -n ⁇ g ⁇ ⁇ asgv ⁇ a s ⁇ lyan ⁇ y ⁇ isl ⁇ gy, 150 ml of 5-n ⁇ g ⁇ ⁇ as ⁇ v ⁇ a ed ⁇ g ⁇ na ⁇ a and v ⁇ d ⁇ y.
  • the claimed new compound is undecyl ether ⁇ -malic acid, it is hypersensitive and non-destructive.
  • the claimed 20 th drug is used in medicine for the treatment of hirplipidemia, including atherosclerosis and a number of clinical trials of diseases.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention se rapporte à une nouvelle substance appelée l'acide n-chlorophénoxyisobutirique d'éther undécylique et à une préparation pharmaceutique à base de ladite substance. L'acide n-chlorophénoxyisobutirique d'éther undécylique présente la formule (I). La combinaison revendiquée est un constituant actif d'une préparation pharmaceutique pour traiter l'hyperlipémie. La préparation revendiquée s'utilise médicalement pour traiter l'hyperlipémie, notamment l'artériosclérose et un certain nombre de maladies vasculaires.
PCT/SU1988/000019 1988-01-22 1988-01-22 ACIDE n-CHLOROPHENOXYISOBUTIRIQUE D'ETHER UNDECYLIQUE ET PREPARATION PHARMACEUTIQUE LE CONTENANT POUR TRAITER L'HYPERLIPEMIE WO1989006643A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP63503721A JPH02502998A (ja) 1988-01-22 1988-01-22 ｎ‐クロロフェノキシイソ酪酸ウンデシルエステルおよびそれを基剤とした高類脂血症の治療用医薬製剤
DE883891219T DE3891219T1 (de) 1988-01-22 1988-01-22 P-chlorphenoxysobuttersaeureundezylester und arzneimittel auf dessen grundlage zur behandlung der hyperlipidaemie
GB8920466A GB2221681A (en) 1988-01-22 1988-01-22 Undecylic ether n-chlorophenoxyisobutyric acid and a pharmaceutical preparation for treating hyperlipemia based on it
PCT/SU1988/000019 WO1989006643A1 (fr) 1988-01-22 1988-01-22 ACIDE n-CHLOROPHENOXYISOBUTIRIQUE D'ETHER UNDECYLIQUE ET PREPARATION PHARMACEUTIQUE LE CONTENANT POUR TRAITER L'HYPERLIPEMIE
FR888805868A FR2630736B1 (fr) 1988-01-22 1988-05-02 Ester undecylique de l'acide p-chlorophenoxyisobutyrique et medicament le contenant pour le traitement de l'hyperlipidemie
SE8903047A SE8903047L (sv) 1988-01-22 1989-09-15 Undecylester av n-klorofenoxiisosmoersyra och paa denna ester baserat laekemedelspreparat foer behandling av hyperlipidemi

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/SU1988/000019 WO1989006643A1 (fr) 1988-01-22 1988-01-22 ACIDE n-CHLOROPHENOXYISOBUTIRIQUE D'ETHER UNDECYLIQUE ET PREPARATION PHARMACEUTIQUE LE CONTENANT POUR TRAITER L'HYPERLIPEMIE

Publications (1)

Publication Number Publication Date
WO1989006643A1 true WO1989006643A1 (fr) 1989-07-27

Family

ID=21617183

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1988/000019 WO1989006643A1 (fr) 1988-01-22 1988-01-22 ACIDE n-CHLOROPHENOXYISOBUTIRIQUE D'ETHER UNDECYLIQUE ET PREPARATION PHARMACEUTIQUE LE CONTENANT POUR TRAITER L'HYPERLIPEMIE

Country Status (6)

Country Link
JP (1) JPH02502998A (fr)
DE (1) DE3891219T1 (fr)
FR (1) FR2630736B1 (fr)
GB (1) GB2221681A (fr)
SE (1) SE8903047L (fr)
WO (1) WO1989006643A1 (fr)

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2287215A1 (fr) * 1974-10-08 1976-05-07 Nippon Kayaku Kk Composition de comprimes
FR2318621A1 (fr) * 1975-07-24 1977-02-18 Takeda Chemical Industries Ltd Granules et comprimes d'acide l-ascorbique et procede pour les preparer
FR2442827A1 (fr) * 1978-12-01 1980-06-27 Kaken Chemical Co Nouveaux acides oxy-cyclohexylacetiques substitues, leur procede de preparation et leur application en therapeutique
US4248889A (en) * 1978-10-30 1981-02-03 Sankyo Company Limited 3,5-Dihydroxypentanoic ester derivatives having antihyperlipaemic activity
DE2461069C3 (de) * 1973-12-27 1981-07-23 Siegfried AG, Zofingen 2-(4-Benzylphenoxy)-alkancarbonsäureester, Verfahren zu ihrer Herstellung und diese Ester enthaltende Arzneimittel
DE2356655C3 (de) * 1972-11-16 1981-12-17 Funai Pharmaceutical Industries, Ltd., Osaka, fuphin Substituierte Phenoxy-α-methylpropionsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2934300C2 (de) * 1978-08-28 1982-06-09 PPG Industries, Inc., 15222 Pittsburgh, Pa. Verfahren zur Herstellung von 2,4,5-Trichlorphenoxyalkancarbonsäureestern oder -amiden bzw. der entsprechenden Säuren
CH644092A5 (de) * 1979-02-08 1984-07-13 Merz & Co Substituierte phenylester von nikotinsaeure und 2(p-chlorphenoxy)-isobuttersaeure.
GB2142822A (en) * 1983-06-29 1985-01-30 Alec Stanley Walter Shaw Nicotine lozenges
EP0142979A2 (fr) * 1983-11-15 1985-05-29 Sterwin Ag. Procédé de préparation d'acides phénoxyalcanoiques et d'esters substitués par des groupements halocyclopropyles
AT378952B (de) * 1981-12-14 1985-10-25 Arcana Chem Pharm Verfahren zur herstellung von phenoxyisobutters|ureestern
FR2598146A1 (fr) * 1986-04-30 1987-11-06 Rech Ind Nouveau procede de preparation de fibrates.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3717669A (en) * 1968-06-18 1973-02-20 American Home Prod 2-phenoxyalkanoic acid esters
FR2085634A1 (en) * 1970-04-14 1971-12-31 Synthelabo 2-(parachlorophenoxy)-2-methyl propionic esters - hypolipemics and hypocholesterolemics
EP0032631A3 (fr) * 1980-01-16 1981-11-11 Fbc Limited Dérivés de l'acide phénoxyalcanoique herbicides, leur préparation, compositions les contenant et leur utilisation

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2356655C3 (de) * 1972-11-16 1981-12-17 Funai Pharmaceutical Industries, Ltd., Osaka, fuphin Substituierte Phenoxy-α-methylpropionsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2461069C3 (de) * 1973-12-27 1981-07-23 Siegfried AG, Zofingen 2-(4-Benzylphenoxy)-alkancarbonsäureester, Verfahren zu ihrer Herstellung und diese Ester enthaltende Arzneimittel
FR2287215A1 (fr) * 1974-10-08 1976-05-07 Nippon Kayaku Kk Composition de comprimes
FR2318621A1 (fr) * 1975-07-24 1977-02-18 Takeda Chemical Industries Ltd Granules et comprimes d'acide l-ascorbique et procede pour les preparer
DE2934300C2 (de) * 1978-08-28 1982-06-09 PPG Industries, Inc., 15222 Pittsburgh, Pa. Verfahren zur Herstellung von 2,4,5-Trichlorphenoxyalkancarbonsäureestern oder -amiden bzw. der entsprechenden Säuren
US4248889A (en) * 1978-10-30 1981-02-03 Sankyo Company Limited 3,5-Dihydroxypentanoic ester derivatives having antihyperlipaemic activity
FR2442827A1 (fr) * 1978-12-01 1980-06-27 Kaken Chemical Co Nouveaux acides oxy-cyclohexylacetiques substitues, leur procede de preparation et leur application en therapeutique
CH644092A5 (de) * 1979-02-08 1984-07-13 Merz & Co Substituierte phenylester von nikotinsaeure und 2(p-chlorphenoxy)-isobuttersaeure.
AT378952B (de) * 1981-12-14 1985-10-25 Arcana Chem Pharm Verfahren zur herstellung von phenoxyisobutters|ureestern
GB2142822A (en) * 1983-06-29 1985-01-30 Alec Stanley Walter Shaw Nicotine lozenges
EP0142979A2 (fr) * 1983-11-15 1985-05-29 Sterwin Ag. Procédé de préparation d'acides phénoxyalcanoiques et d'esters substitués par des groupements halocyclopropyles
FR2598146A1 (fr) * 1986-04-30 1987-11-06 Rech Ind Nouveau procede de preparation de fibrates.

Also Published As

Publication number Publication date
GB8920466D0 (en) 1989-11-01
FR2630736A1 (fr) 1989-11-03
GB2221681A (en) 1990-02-14
FR2630736B1 (fr) 1990-08-24
JPH02502998A (ja) 1990-09-20
SE8903047D0 (sv) 1989-09-15
SE8903047L (sv) 1989-09-15
DE3891219T1 (de) 1990-02-01

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