SU1287756A3 - Способ получени производных дипептидов - Google Patents
Способ получени производных дипептидов Download PDFInfo
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- SU1287756A3 SU1287756A3 SU792851802A SU2851802A SU1287756A3 SU 1287756 A3 SU1287756 A3 SU 1287756A3 SU 792851802 A SU792851802 A SU 792851802A SU 2851802 A SU2851802 A SU 2851802A SU 1287756 A3 SU1287756 A3 SU 1287756A3
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- USSR - Soviet Union
- Prior art keywords
- alkyl
- substituted
- alkoxy
- hydrogen
- acylamino
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- 108010016626 Dipeptides Proteins 0.000 title claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
- 239000012445 acidic reagent Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- -1 alkenoxy Chemical group 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000001475 halogen functional group Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000004442 acylamino group Chemical group 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000004475 heteroaralkyl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 abstract 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 abstract 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229960002429 proline Drugs 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- PPKAIMDMNWBOKN-UHFFFAOYSA-N 2-Oxo-4-phenylbutyric acid Chemical compound OC(=O)C(=O)CCC1=CC=CC=C1 PPKAIMDMNWBOKN-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- WPWUFUBLGADILS-WDSKDSINSA-N Ala-Pro Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O WPWUFUBLGADILS-WDSKDSINSA-N 0.000 description 2
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 108010087924 alanylproline Proteins 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/80—Antihypertensive peptides
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Изобретение касаетс производных пептидов, в частности соедин ен ий общей формулы CgHj - (СНр)2 - CH(COOR,) - NH-CHR,- С(О) N - СН(СООН)-(СЙ2)2-СН, где Н Н; Ra CHj; -(GHz)-, -NH , которые способны ингибировать ангиотензинконвертирующий эффект и могут быть использованы в экспериментальной биологии и медицине. Дл вы влени лучшей активности у соединений указанного класса были синтезированы новые 1 . Их получают из - (CHj)2-C(0)-COORi и (CH2),ij , где RZ СН(СООН)-N-C(0)-CHRjNH, СН,; CHj(CH2)-NH-C(0)0-C-(CH,) 3 в присутствии натрийцианбаргидрида: как восстановител споследующим удалением, при необходимости, защитных групп обработкой соответствующей кислотой. Получены: 1а) К-(1-кар- бокси-3-фенилпропил)-с.-аланил-5 -про- лин S, S, З конфигурации, т.пл. 148 - 15rC,dlp -67°; 1 б) N- - - (S) -этоксикарОонил-З-фенилпро- пионил)-с(-аланил- А-пролин, т.пл. 144 - 145°C,d.3f -43, 1 в) N-t1-(8)-карбокси-3-фенилпропил-
Description
. 11
Изобретение относитс к спосббу получени новых биологически активных соединений, а именно производных дипептидов обп;ей формулы
RlOOC-CH-MH-CH- CON
V
соон
где RI R.
водород,
СН, -СН СН2СН,СН2 NH,,
обладающих способностью ингйбиро вать ангиотенэинконвертирующий фермент, который может найти применение в экспериментальной биологии и медицине.
Цель изобретени - способ получени новых производных дипептидов, обладающих более высокой способностью ингибировать ангиотензинконвер- тирующий фермент.
П р и м е р 1. Получение N-(1- -карбокси-3-фенилпропил)-L-аланил- -L-пролина.
Смесь 1,49 г 4-фенил-2-оксомасл - ной кислоты и 0,31 г Ь-аланил-Ь-про- лина в воде при рН 7,5 обрабатывают 0,32 г натрийцианборгидрида в течение ночи. Затем реакционную смесь пропускают через колонку с сильнокислотной ионообменной смолой. Целевой продукт элюируют с помощью 2%- ного раствора пиридина в воде. В итоге получают 0,36 г сырого продукта , который дополнительно очищают
с помощью колоночной хроматографии на полистирольной смоле ХАД-2 (меш. 200-400), использу в качестве элю- ента 0,1 М раствор гидроокиси аммони в смеси вода - метанол, 95:5 (объем). Первый изомер выходит, из колонки после пропускани 375-400 мл элюента, а второй - с 440-480 мл элюента вместе с промежуточными фракци ми , содержащими смесь изомеров. Фракцию, содержащую первый изомер сушат лиофильно. В итоге получают 0,13 г белого твердого вещества,ко- . тор оеб перекристаллизовывают из 1 мл воды, подкисленной до рН 3,0. В итоге получают 0,094 г N- d-Kap бокси-3-фенилпропил)-1-аланил-Ь- -пролина, имеющего по данным рент- геноструктурного анализа S, S, 5-кон фигурацию, с т.пл. 148 - 151 С ; -67,0° (С 0,1; НС1).
JO
J5
20
25
ЗО -
877562
П р и м е р 2. Получение N-(1- -(S)-этoкcикapбoнил-3-фeнилпpoпиo- нил)-L-aлa fил-L-пpoлинa .
1,03 г этилового эфира 2-оксо-4- 5 -фенилмасл ной кислоты и 0,19 г . Ь-аланил-Ь-пролина раствор ют в 50% ном водном этаноле. К полученному раствору- по капл м добавл ют 0,19 г натрийцианборгидрида в водном этаноле в течение 2 ч. По окончании реакции раствор пропускают через колонку с сильнокислотной ионообменной смолой, элюиру целевой продукт 2%- ным раствором гТиридина в воде. Фракции , содержащие продукт, лиофилизу- ют. В итоге получают 0,25 г сырого продукта, из которого целевой изомер выдел ют с помощью колоночной хроматографии аналогично примеру 1. В итоге получают N-(1-(3)-этоксикарбонил- -3-фенилпропионил)-Ь-аланил-Ь-пролин , с т.пл. 144 - 145°С; 1 -43,5° (С 1; АсОН).
П р и м е р 3. Долучение N-(1- -(5)-карбокси-3-фенилпропил)-Ь-ли- зил-Ь-пролина.
2-оксо-4-фенилмасл ную кислоту конденсируют с N -трет-бутилоксикар- бонил-Ь-лизил-Ь-пролином в присутствии натрийцианборгидрида в услови х примера 1. Продукт конденсации адсорбируют на сильнокислотной ионообменной смоле, а затем элюируют 2%-ным раствором пиридина в воде. Фракции, содержащие продукт, упаривают , остаток обрабатывают 4 н. раствором НС1 в этилацетате, раствор упаривают . Полученный продукт адсорбируют на сильнокислотной ионообменной смоле, а затем элюируют 2%-ным раствором пиридина в воде. Фракции, содержащие целевой продукт, лиофили- зуют. В итоге получают Н-(1(5)-это- ксикарбонил-3-фенилпропионил)-Ь-аланил-Ь-пролин в виде белого порошка с т.пл. 150 (разл.) с содержанием основного вещества по данным НРЬ С 98, (С 1; АсОН).
Полученные в примерах 1 - 3 соединени в опытах in vivo и in vitro показали высокую ингибиторную активность в отношении ангиотензинкон- вертирующего фермента в сочетании с низкой токсичностью.
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Claims (1)
- Формула изобретениСпособ получени производных дипептидов общей формулыгде R. имеет указанные значени ,/-Iгде к. имеет указанные значени ,.H.CONv.конденсируют с дипептидом общей,,Л/формулыформулысоонH-iN-CH-CONrгде Rj - водород, -R - СН, -CHjCHg CHjCH -NHg,где , -СН(СН,)з-Ш-СООС(СН) отличающий с. тем, что . в присутствии натрийцианборгидрида всоединение общей формулыкачестве восстанавливающего аген.таг-Xс последующим удалением в случаеР,ООС С СН7СН. /необходимости защитных групп привзаимодействии с соответствующим.кислотным реагентом.1287756где R. имеет указанные значени ,где к. имеет указанные значени ,.конденсируют с дипептидом общейH-iN-CH-CONr-iL 1 vjvjlA
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LV920592A LV5276A3 (lv) | 1978-12-11 | 1992-12-30 | Dipeptidu atvasinajumu iegusanas metode |
LTRP617A LT2158B (lt) | 1978-12-11 | 1993-06-04 | Dipeptidu dariniu gavimo budas |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US96824978A | 1978-12-11 | 1978-12-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU1287756A3 true SU1287756A3 (ru) | 1987-01-30 |
Family
ID=25513965
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU792851802A SU1287756A3 (ru) | 1978-12-11 | 1979-12-10 | Способ получени производных дипептидов |
Country Status (33)
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---|---|
US (2) | US4374829A (ru) |
EP (1) | EP0012401B1 (ru) |
JP (3) | JPS5581845A (ru) |
KR (3) | KR850000847B1 (ru) |
AR (1) | AR231971A1 (ru) |
AU (1) | AU530380B2 (ru) |
BG (6) | BG39467A3 (ru) |
CA (4) | CA1302005C (ru) |
CS (1) | CS237311B2 (ru) |
DD (1) | DD148770A5 (ru) |
DE (2) | DE19375005I2 (ru) |
DK (1) | DK165455C (ru) |
EG (1) | EG14182A (ru) |
ES (2) | ES8101540A1 (ru) |
FI (1) | FI68405C (ru) |
GR (1) | GR72251B (ru) |
HK (1) | HK27487A (ru) |
HU (1) | HU182902B (ru) |
IE (1) | IE48922B1 (ru) |
IL (1) | IL58849A (ru) |
LU (1) | LU90173I2 (ru) |
MA (1) | MA18664A1 (ru) |
NL (4) | NL930008I2 (ru) |
NO (3) | NO151622C (ru) |
NZ (1) | NZ192312A (ru) |
PH (1) | PH24268A (ru) |
PL (2) | PL126126B1 (ru) |
PT (1) | PT70542A (ru) |
RO (4) | RO85072B (ru) |
SU (1) | SU1287756A3 (ru) |
YU (3) | YU42655B (ru) |
ZA (1) | ZA796688B (ru) |
ZW (1) | ZW24479A1 (ru) |
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Cited By (4)
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RU2166510C2 (ru) * | 1993-02-22 | 2001-05-10 | Экссимоль Сосьете Аноним Монегаск | Псевдодипептиды, способы их получения, фармацевтические композиции, способы лечения |
RU2125056C1 (ru) * | 1993-06-15 | 1999-01-20 | Бристоль-Мейерз Сквибб Компани | Соединения, содержащие конденсированное бициклическое ядро, промежуточные соединения, способы их получения и фармацевтическая композиция для ингибирования превращения фермента ангиотензина и нейтральной эндопептидазы |
RU2159775C2 (ru) * | 1993-11-05 | 2000-11-27 | Экссимоль Сосьете Аноним Монегаск | Псевдодипептидный продукт, содержащий имидазольную группу, и его применение |
RU2141483C1 (ru) * | 1997-07-04 | 1999-11-20 | Небольсин Владимир Евгеньевич | Производные пептидов или их фармацевтически приемлемые соли, способ их получения, применение и фармацевтическая композиция |
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