SU1660578A3 - Способ получени N-[3-(N-циклопентакарбонил-D-аланилтио)-2-D-метилпропаноил]-L-пролина - Google Patents
Способ получени N-[3-(N-циклопентакарбонил-D-аланилтио)-2-D-метилпропаноил]-L-пролина Download PDFInfo
- Publication number
- SU1660578A3 SU1660578A3 SU813263400A SU3263400A SU1660578A3 SU 1660578 A3 SU1660578 A3 SU 1660578A3 SU 813263400 A SU813263400 A SU 813263400A SU 3263400 A SU3263400 A SU 3263400A SU 1660578 A3 SU1660578 A3 SU 1660578A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- cyclopentacarbonyl
- proline
- alanylthio
- methylpropanoyl
- alanine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims abstract description 12
- 229960000830 captopril Drugs 0.000 claims abstract description 12
- 229960002429 proline Drugs 0.000 claims abstract description 11
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims abstract description 3
- 229930182821 L-proline Natural products 0.000 claims abstract description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims abstract 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims abstract 3
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims abstract 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims abstract 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 241000272814 Anser sp. Species 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 2
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 231100001231 less toxic Toxicity 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 abstract 1
- 229960002317 succinimide Drugs 0.000 abstract 1
- 231100000167 toxic agent Toxicity 0.000 abstract 1
- 239000003440 toxic substance Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- -1 Carbonyl-O-alanylthio Chemical group 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
- VXDSLUMUNWTSDB-UHFFFAOYSA-N acetic acid;chloroform;methanol Chemical compound OC.CC(O)=O.ClC(Cl)Cl VXDSLUMUNWTSDB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012134 supernatant fraction Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Landscapes
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12895380A | 1980-03-10 | 1980-03-10 | |
| AU73631/81A AU7363181A (en) | 1980-03-10 | 1981-07-31 | Anti-ace peptide preparative methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1660578A3 true SU1660578A3 (ru) | 1991-06-30 |
Family
ID=25637364
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813263400A SU1660578A3 (ru) | 1980-03-10 | 1981-03-09 | Способ получени N-[3-(N-циклопентакарбонил-D-аланилтио)-2-D-метилпропаноил]-L-пролина |
| SU864015511A SU1609455A3 (ru) | 1980-03-10 | 1986-01-28 | Способ получени пептидов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864015511A SU1609455A3 (ru) | 1980-03-10 | 1986-01-28 | Способ получени пептидов |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS56164154A (enExample) |
| SU (2) | SU1660578A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692458A (en) * | 1980-03-05 | 1987-09-08 | University Of Miami | Anti-hypertensive agents |
-
1981
- 1981-03-09 SU SU813263400A patent/SU1660578A3/ru active
- 1981-03-10 JP JP3445781A patent/JPS56164154A/ja active Granted
-
1986
- 1986-01-28 SU SU864015511A patent/SU1609455A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Шредер Э. и Любке К. Пептиды. М.: Мир, 1967,4. I.e. 116. * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56164154A (en) | 1981-12-17 |
| SU1609455A3 (ru) | 1990-11-23 |
| JPH0419228B2 (enExample) | 1992-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0489032B1 (en) | Hydroxamic acid based collagenase inhibitors | |
| US4918105A (en) | Novel compounds with collagenase-inhibiting activity, a process for their preparation and pharmaceutical compositions in which these compounds are present | |
| US4235885A (en) | Inhibitors of mammalian collagenase | |
| DE3789371T2 (de) | Aryloxy- und Arylacyloxymethyl-Ketone als Thiolprotease-Hemmungsstoffe. | |
| EP0038758B1 (fr) | Dérivés d'acides aminés et leur application thérapeutique | |
| RU2127723C1 (ru) | Нитроэфиры, обладающие фармакологической активностью, и способы их получения | |
| CA1322076C (en) | Phosphorus containing peptides | |
| EP0232849B1 (en) | Pyrrolidineamide derivative of acylamino acid, pharmaceutical composition and use | |
| EP0082088A1 (fr) | Nouveaux dérivés d'aminoacides, et leur application thérapeutique | |
| EP0273689B1 (en) | Derivatives of n-(2-alkyl-3-mercapto-glutaryl) alpha-amino acids and their use as collagenase inhibitors | |
| US5455262A (en) | Mercaptosulfide metalloproteinase inhibitors | |
| US4297275A (en) | Inhibitors of mammalian collagenase | |
| EP0067429A1 (en) | Inhibitors of mammalian collagenase | |
| EP0275482A2 (en) | Proline derivatives | |
| KR19980086989A (ko) | 치환된 6- 및 7- 아미노-테트라하이드로이소퀴놀린 카복실산 | |
| US4639451A (en) | Pyridazinone derivatives | |
| US6339160B1 (en) | Metalloproteinase inhibitors, their therapeutic use and process for the production of the starting compound in the synthesis thereof | |
| SU1272982A3 (ru) | Способ получени производных пролина или их фармацевтически приемлемых солей | |
| EP0262053A2 (fr) | Nouveaux dérivés d'amino-acides, leur procédé de préparation et compositions pharmaceutiques les contenant | |
| SU1660578A3 (ru) | Способ получени N-[3-(N-циклопентакарбонил-D-аланилтио)-2-D-метилпропаноил]-L-пролина | |
| EP0828851A2 (fr) | Inhibiteurs de tripeptidylpeptidases | |
| PT97782A (pt) | Processo para a preparacao de peptideos inibidores da protease do hiv | |
| EP0210896B1 (fr) | Dérivés d'acides amino-4 hydroxy-3 carboxyliques optiquement purs et procédé de synthèse stéréospécifique | |
| FI62066C (fi) | Foerfarande foer framstaellning av antitrombotiska cyklohexylfenylderivat | |
| US4734420A (en) | Anti-hypertensive agents |