RU2004117874A - Производные соединения карбоновой кислоты и средства, содержащие соединения в качестве активных ингредиентов - Google Patents
Производные соединения карбоновой кислоты и средства, содержащие соединения в качестве активных ингредиентов Download PDFInfo
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- RU2004117874A RU2004117874A RU2004117874/04A RU2004117874A RU2004117874A RU 2004117874 A RU2004117874 A RU 2004117874A RU 2004117874/04 A RU2004117874/04 A RU 2004117874/04A RU 2004117874 A RU2004117874 A RU 2004117874A RU 2004117874 A RU2004117874 A RU 2004117874A
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- Prior art keywords
- allyl
- ethoxy
- benzyl
- amino
- acetic acid
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- 150000001875 compounds Chemical class 0.000 title claims 17
- 239000004480 active ingredient Substances 0.000 title claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 26
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 231100000252 nontoxic Toxicity 0.000 claims 4
- 230000003000 nontoxic effect Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- -1 carboxylic acid compound Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010020710 Hyperphagia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 235000020830 overeating Nutrition 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61K31/433—Thidiazoles
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings 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, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
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- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Claims (16)
1. Производное соединения карбоновой кислоты, представленное формулой (I)
где X и Y, каждый независимо, представляет собой C1-4 алкилен;
Z означает -O- или -S-;
R1, R2, R3 и R4, каждый независимо, означает атом водорода, или C1-8 алкил;
R5 означает C2-8 алкенил;
A означает -O- или -S-;
D является D1, D2, D3, D4 или D5;
D1 означает C1-8 алкил;
кольцо 1 является насыщенным 3-7-членным моногетероарилом, содержащим один атом азота и, необязательно, другой один гетероатом, выбранный из атома кислорода, серы и азота;
кольцо 2 является
(1) необязательно, частично или полностью насыщенным С3-10 моно- или бикарбоциклическим арилом, или
(2) необязательно, частично или полностью насыщенным 3-10-членным моно- или бигетероарилом, содержащим 1-4 гетероатома, выбранного из атомов кислорода, азота и серы;
R6 представляет собой (1) атом водорода, (2) C1-8 алкил, (3) C1-8 алкокси, (4) CF3, (5) OCF3, (6) атом галогена, (7) нитро или (8) NR7R8;
R7 или R8 представляют собой атом водорода или C1-8 алкил, или
R7 и R8, взятые вместе с атомом азота, к которому они присоединены, образуют насыщенный 3-7-членный моногетероарил, содержащий один атом азота и, необязательно, другой один гетероатом, выбранный из атомов кислорода, серы и азота, и насыщенный гетероарил, необязательно, является замещенным С1-8 алкилом;
E означает CH или атом азота; и
m равно целому числу 1-3, или
его нетоксичная соль.
2. Соединение по п.1, где Z является -S-.
3. Соединение по п.1, где Z является -O- и D является D1, D2 D3 или D4.
4. Соединение по п.1, где D является D1.
5. Соединение по п.1, где D является D2.
6. Соединение по п.1, где D является D3.
7. Соединение по п.1, где D является D4.
8. Соединение по п.1, где D является D5.
9. Соединение по п.4, которое представляет собой
(1) этиловый эфир 2-(N-аллил-N-(3-(2-(2-изопропил-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты, или
(2) 2-(N-аллил-N-(3-(2-(2-изопропил-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту.
10. Соединение по п.5, которое представляет собой
(1) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(4-метилпиперазин-1-ил)-5-метилтиазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(2) этиловый эфир 2-(N-аллил-N-(3-(2-(5-метил-2-пиперидинотиазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(3) трет-бутиловый эфир 2-(N-аллил-N-(3-(2-(2-морфолино-5-метилтиазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(4) 2-(N-аллил-N-(3-(2-(2-(4-метилпиперазин-1-ил)-5-метилтиазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(5) 2-(N-аллил-N-(3-(2-(5-метил-2-пиперидинотиазол-4-ил)этокси)бензил)амино)уксусную кислоту или
(6) 2-(N-аллил-N-(3-(2-(5-метил-2-морфолинотиазол-4-ил)этокси)бензил)амино)уксусную кислоту.
11. Соединение по п.6, которое представляет собой
(1) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(4-(1,2,3-тиадиазол-4-ил)фенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(2) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(4-циклогексилфенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(3) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(4-(тетрагидропиран-4-ил)фенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(4) 2-(N-аллил-N-(3-(2-(2-(4-(1,2,3-тиадиазол-4-ил)фенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(5) 2-(N-аллил-N-(3-(2-(2-(4-циклогексилфенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту, или
(6) 2-(N-аллил-N-(3-(2-(2-(4-(тетрагидропиран-4-ил)фенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту.
12. Соединение по п.7, которое представляет собой
(1) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(6-(пергидроазепин-1-ил)пиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты, или
(2) 2-(N-аллил-N-(3-(2-(2-(6-(пергидроазепин-1-ил)пиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту.
13 Соединение по п.8, которое представляет собой
(1) этиловый эфир 2-(N-аллил-N-(3-(2-(2-фенил-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(2) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(6-диметиламинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(3) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(4-диметиламинофенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(4) метиловый эфир 2-(N-аллил-N-(3-(2-(5-метил-2-фенилоксазол-4-ил)этокси)бензил)амино)-2-метилпропионовой кислоты,
(5) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(6-морфолинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(6) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(6-пиперидинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(7) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(6-диэтиламинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(8) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(6-пирролидинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(9) этиловый эфир 2-(N-аллил-N-(3-(2-(2-(4-морфолинофенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(10) этиловый эфир 2-(N-аллил-N-(4-(2-(5-метил-2-фенилоксазол-4-ил)этокси)бензил)амино)уксусной кислоты,
(11) 2-(N-аллил-N-(3-(2-(5-метил-2-фенилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(12) 2-(N-аллил-N-(3-(2-(2-(6-диметиламинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(13) 2-(N-аллил-N-(3-(2-(2-(4-диметиламинофенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(14) 2-(N-аллил-N-(3-(2-(2-фенил-5-метилоксазол-4-ил)этокси)бензил)амино)-2-метилпропионовую кислоту,
(15) 2-(N-аллил-N-(3-(2-(2-(6-морфолинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(16) 2-(N-аллил-N-(3-(2-(2-(6-пиперидинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(17) 2-(N-аллил-N-(3-(2-(2-(6-диэтиламинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(18) 2-(N-аллил-N-(3-(2-(2-(6-пирролидинопиридин-3-ил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту,
(19) 2-(N-аллил-N-(3-(2-(2-(4-морфолинофенил)-5-метилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту, или
(20) 2-(N-аллил-N-(4-(2-(5-метил-2-фенилоксазол-4-ил)этокси)бензил)амино)уксусную кислоту.
14. Регулятор активируемого пероксисомным пролифератором рецептора, включающий в себя, в качестве активного ингредиента, соединение, представленное формулой (I) согласно п.1, или его нетоксичную соль.
15. Средство для профилактики и/или лечения заболеваний, связанных с нарушениями метаболизма, таких как диабет, ожирение, синдром Х, гиперхолестеринемия или гиперлипопротеинемия, гиперлипидемия, атеросклероз, гипертензия, болезни, протекающие с расстройством кровообращения, переедание или ишемическая болезнь сердца, которое содержит, в качестве активного ингредиента, соединение, представленное формулой (I) согласно п.1, или его нетоксичную соль.
16. Средство, которое повышает уровень холестерина, связанного с HDL, снижает уровень холестерина, связанного с LDL и/или VLDL, устраняет фактор риска появления диабета и/или синдрома Х, содержащее, в качестве активного ингредиента, соединение, представленное формулой (I) согласно п.1, или его нетоксичную соль.
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