RU2148056C1 - Замещенные азетидиноны, способ их получения, фармацевтическая композиция и способ лечения - Google Patents
Замещенные азетидиноны, способ их получения, фармацевтическая композиция и способ лечения Download PDFInfo
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- RU2148056C1 RU2148056C1 RU95109936A RU95109936A RU2148056C1 RU 2148056 C1 RU2148056 C1 RU 2148056C1 RU 95109936 A RU95109936 A RU 95109936A RU 95109936 A RU95109936 A RU 95109936A RU 2148056 C1 RU2148056 C1 RU 2148056C1
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- alkyl
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- hydrogen
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- oxo
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- 238000000034 method Methods 0.000 title claims abstract description 51
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 230000015572 biosynthetic process Effects 0.000 title abstract description 6
- 238000003786 synthesis reaction Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 190
- 230000000694 effects Effects 0.000 claims abstract description 16
- 239000003112 inhibitor Substances 0.000 claims abstract description 14
- 102100033174 Neutrophil elastase Human genes 0.000 claims abstract description 4
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 378
- -1 methylenedioxy group Chemical group 0.000 claims description 371
- 239000001257 hydrogen Substances 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 128
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 96
- 125000003277 amino group Chemical group 0.000 claims description 75
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000002950 monocyclic group Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000005518 carboxamido group Chemical group 0.000 claims description 19
- 125000003386 piperidinyl group Chemical group 0.000 claims description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 18
- 108010067372 Pancreatic elastase Proteins 0.000 claims description 17
- 102000016387 Pancreatic elastase Human genes 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000006177 alkyl benzyl group Chemical group 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 11
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002393 azetidinyl group Chemical group 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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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- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96680092A | 1992-10-27 | 1992-10-27 | |
| US966,800 | 1992-10-27 | ||
| US966.800 | 1992-10-27 | ||
| US99183892A | 1992-12-17 | 1992-12-17 | |
| US991.838 | 1992-12-17 | ||
| US991,838 | 1992-12-17 | ||
| PCT/US1993/010268 WO1994010142A1 (en) | 1992-10-27 | 1993-10-26 | New substituted azetidinones as anti-inflammatory and antidegenerative agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU95109936A RU95109936A (ru) | 1997-01-10 |
| RU2148056C1 true RU2148056C1 (ru) | 2000-04-27 |
Family
ID=27130493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU95109936A RU2148056C1 (ru) | 1992-10-27 | 1993-10-26 | Замещенные азетидиноны, способ их получения, фармацевтическая композиция и способ лечения |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0595557B1 (enExample) |
| JP (1) | JPH082868B2 (enExample) |
| KR (1) | KR950704250A (enExample) |
| CN (1) | CN1043884C (enExample) |
| AT (1) | ATE270273T1 (enExample) |
| AU (1) | AU663806B2 (enExample) |
| CA (1) | CA2108584C (enExample) |
| CY (1) | CY2529B1 (enExample) |
| CZ (1) | CZ106895A3 (enExample) |
| DE (1) | DE69333563T2 (enExample) |
| DK (1) | DK0595557T3 (enExample) |
| DZ (1) | DZ1724A1 (enExample) |
| ES (1) | ES2224095T3 (enExample) |
| FI (1) | FI951992A7 (enExample) |
| HR (1) | HRP931309A2 (enExample) |
| HU (2) | HUT72084A (enExample) |
| IL (1) | IL107321A (enExample) |
| LV (1) | LV13338B (enExample) |
| MX (1) | MX9306666A (enExample) |
| MY (1) | MY128261A (enExample) |
| NO (1) | NO305697B1 (enExample) |
| NZ (1) | NZ257755A (enExample) |
| PL (1) | PL308545A1 (enExample) |
| PT (1) | PT595557E (enExample) |
| RU (1) | RU2148056C1 (enExample) |
| SI (1) | SI9300566A (enExample) |
| SK (1) | SK53795A3 (enExample) |
| TW (1) | TW275621B (enExample) |
| WO (1) | WO1994010142A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2191570C1 (ru) * | 2001-04-25 | 2002-10-27 | Закрытое акционерное общество "ВЕРОФАРМ" | Твердая лекарственная форма антимикробного средства |
| RU2207115C1 (ru) * | 2001-12-27 | 2003-06-27 | Закрытое акционерное общество "Брынцалов-А" | Противомикробное средство тариферид |
| RU2217196C2 (ru) * | 2002-02-28 | 2003-11-27 | Небольсин Владимир Евгеньевич | Способ индукции дифференцировки клеток |
| RU2358725C2 (ru) * | 2003-11-07 | 2009-06-20 | Сантр Насьональ Де Ля Решерш Сьентифик | Применение ингибиторов глюкозидазы для терапии муковисцидоза |
| RU2496778C2 (ru) * | 2009-03-09 | 2013-10-27 | Тайхо Фармасьютикал Ко., Лтд. | Пиперазиновое соединение, ингибирующее простагландин-d-синтазу |
| RU2569886C2 (ru) * | 2008-11-04 | 2015-12-10 | Галдерма Ресерч Энд Девелопмент | Производные оксоазетидина, способ их получения и их применения в медицине и косметологии |
| RU2624011C2 (ru) * | 2011-06-30 | 2017-06-30 | Галдерма Ресерч Энд Девелопмент | Производные оксазетидина, способ для их получения и их применение в медицине и косметике |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420010A (en) * | 1993-07-30 | 1995-05-30 | Merck & Co., Inc. | Assay for evaluating inhibition of polymorphonuclear leukocyte elastase by N-substituted azetidinones |
| AU5014496A (en) * | 1995-03-23 | 1996-10-08 | Japan Tobacco Inc. | Diphenylmethyl-azetidinone compounds and elastase inhibitor |
| US5523233A (en) * | 1995-05-03 | 1996-06-04 | Merck & Co., Inc. | Enzymatic hydrolysis of 3,3-diethyl-4-[(4-carboxy)phenoxy]-2-azetidinone esters |
| CA2234640A1 (en) * | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Process for preparing substituted azetidinones |
| US5808056A (en) * | 1995-10-31 | 1998-09-15 | Merck & Co., Inc. | Process for preparing substituted azetidinones |
| JP2000502079A (ja) * | 1995-12-08 | 2000-02-22 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | アテローム性動脈硬化症の治療のための単環β―ラクタム誘導体 |
| JP2000509049A (ja) * | 1996-04-26 | 2000-07-18 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | アテローム性動脈硬化症の治療用アゼチジノン誘導体 |
| CN1202081C (zh) * | 1998-06-25 | 2005-05-18 | 布里斯托尔-迈尔斯斯奎布公司 | 脒基和胍基β－丙内酰胺类胰蛋白酶抑制剂 |
| AU4654199A (en) * | 1998-07-23 | 2000-02-14 | Shionogi & Co., Ltd. | Monocyclic beta-lactam compounds and chymase inhibitors containing the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ228600A (en) * | 1988-04-11 | 1992-02-25 | Merck & Co Inc | 1-(benzylaminocarbonyl)-4-phenoxy-azetidin-2-one derivatives |
| IL99658A0 (en) * | 1990-10-15 | 1992-08-18 | Merck & Co Inc | Substituted azetidinones and pharmaceutical compositions containing them |
| WO1993000332A1 (en) * | 1991-06-25 | 1993-01-07 | Merck & Co., Inc. | Substituted azetidinones as anti-inflammatory and antidegenerative agents |
-
1993
- 1993-10-18 MY MYPI93002128A patent/MY128261A/en unknown
- 1993-10-18 CA CA002108584A patent/CA2108584C/en not_active Expired - Lifetime
- 1993-10-18 TW TW082108642A patent/TW275621B/zh active
- 1993-10-19 HR HR07/991,838A patent/HRP931309A2/xx not_active Application Discontinuation
- 1993-10-19 IL IL10732193A patent/IL107321A/en not_active IP Right Cessation
- 1993-10-22 ES ES93308421T patent/ES2224095T3/es not_active Expired - Lifetime
- 1993-10-22 AT AT93308421T patent/ATE270273T1/de active
- 1993-10-22 PT PT93308421T patent/PT595557E/pt unknown
- 1993-10-22 DK DK93308421T patent/DK0595557T3/da active
- 1993-10-22 DE DE69333563T patent/DE69333563T2/de not_active Expired - Lifetime
- 1993-10-22 EP EP93308421A patent/EP0595557B1/en not_active Expired - Lifetime
- 1993-10-26 WO PCT/US1993/010268 patent/WO1994010142A1/en not_active Ceased
- 1993-10-26 CZ CZ951068A patent/CZ106895A3/cs unknown
- 1993-10-26 PL PL93308545A patent/PL308545A1/xx unknown
- 1993-10-26 NZ NZ257755A patent/NZ257755A/en unknown
- 1993-10-26 RU RU95109936A patent/RU2148056C1/ru active
- 1993-10-26 MX MX9306666A patent/MX9306666A/es not_active IP Right Cessation
- 1993-10-26 HU HU9501184A patent/HUT72084A/hu unknown
- 1993-10-26 CN CN93119648A patent/CN1043884C/zh not_active Expired - Fee Related
- 1993-10-26 SK SK537-95A patent/SK53795A3/sk unknown
- 1993-10-26 AU AU50283/93A patent/AU663806B2/en not_active Expired
- 1993-10-27 SI SI9300566A patent/SI9300566A/sl unknown
- 1993-10-27 DZ DZ930115A patent/DZ1724A1/fr active
- 1993-10-27 JP JP5292692A patent/JPH082868B2/ja not_active Expired - Lifetime
-
1995
- 1995-04-26 FI FI951992A patent/FI951992A7/fi unknown
- 1995-04-26 NO NO951593A patent/NO305697B1/no not_active IP Right Cessation
- 1995-04-27 KR KR1019950701629A patent/KR950704250A/ko not_active Ceased
- 1995-06-30 HU HU95P/P00639P patent/HU211619A9/hu unknown
-
2005
- 2005-06-08 LV LVP-05-69A patent/LV13338B/en unknown
- 2005-08-29 CY CY0500046A patent/CY2529B1/xx unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2191570C1 (ru) * | 2001-04-25 | 2002-10-27 | Закрытое акционерное общество "ВЕРОФАРМ" | Твердая лекарственная форма антимикробного средства |
| RU2207115C1 (ru) * | 2001-12-27 | 2003-06-27 | Закрытое акционерное общество "Брынцалов-А" | Противомикробное средство тариферид |
| RU2217196C2 (ru) * | 2002-02-28 | 2003-11-27 | Небольсин Владимир Евгеньевич | Способ индукции дифференцировки клеток |
| RU2358725C2 (ru) * | 2003-11-07 | 2009-06-20 | Сантр Насьональ Де Ля Решерш Сьентифик | Применение ингибиторов глюкозидазы для терапии муковисцидоза |
| RU2569886C2 (ru) * | 2008-11-04 | 2015-12-10 | Галдерма Ресерч Энд Девелопмент | Производные оксоазетидина, способ их получения и их применения в медицине и косметологии |
| RU2671189C1 (ru) * | 2008-11-04 | 2018-10-30 | Галдерма Ресерч Энд Девелопмент | Производные оксоазетидина, способ их получения и их применения в медицине и косметологии |
| RU2496778C2 (ru) * | 2009-03-09 | 2013-10-27 | Тайхо Фармасьютикал Ко., Лтд. | Пиперазиновое соединение, ингибирующее простагландин-d-синтазу |
| RU2624011C2 (ru) * | 2011-06-30 | 2017-06-30 | Галдерма Ресерч Энд Девелопмент | Производные оксазетидина, способ для их получения и их применение в медицине и косметике |
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