JPH0521092B2 - - Google Patents
Info
- Publication number
- JPH0521092B2 JPH0521092B2 JP61115674A JP11567486A JPH0521092B2 JP H0521092 B2 JPH0521092 B2 JP H0521092B2 JP 61115674 A JP61115674 A JP 61115674A JP 11567486 A JP11567486 A JP 11567486A JP H0521092 B2 JPH0521092 B2 JP H0521092B2
- Authority
- JP
- Japan
- Prior art keywords
- phe
- cei
- pro
- column
- val
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 235000013305 food Nutrition 0.000 claims description 18
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 18
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 14
- GIQZFLZPSASIEJ-UHFFFAOYSA-N Ala-Val-Pro-Tyr-Pro-Gln-Arg Natural products CC(N)C(=O)NC(C(C)C)C(=O)N1CCCC1C(=O)NC(C(=O)N1C(CCC1)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(O)=O)CC1=CC=C(O)C=C1 GIQZFLZPSASIEJ-UHFFFAOYSA-N 0.000 claims description 4
- ILZZTQYNTRWQSJ-UHFFFAOYSA-N Phe-Phe-Val-Ala-Pro-Phe-Pro-Glu-Val-Phe-Gly-Lys Natural products CC(C)C(NC(=O)C(Cc1ccccc1)NC(=O)C(N)Cc2ccccc2)C(=O)NC(C)C(=O)N3CCCC3C(=O)NC(Cc4ccccc4)C(=O)N5CCCC5C(=O)NC(CCC(=O)O)C(=O)NC(C(C)C)C(=O)NC(Cc6ccccc6)C(=O)NCC(=O)NC(CCCCN)C(=O)O ILZZTQYNTRWQSJ-UHFFFAOYSA-N 0.000 claims description 4
- LQZZPNDMYNZPFT-KKUMJFAQSA-N Pro-Gln-Phe Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O LQZZPNDMYNZPFT-KKUMJFAQSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 25
- 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 23
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 23
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 13
- 230000002401 inhibitory effect Effects 0.000 description 13
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000010828 elution Methods 0.000 description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 102000004142 Trypsin Human genes 0.000 description 6
- 108090000631 Trypsin Proteins 0.000 description 6
- 239000005018 casein Substances 0.000 description 6
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 6
- 235000021240 caseins Nutrition 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
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- 108090000790 Enzymes Proteins 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
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- 241000283690 Bos taurus Species 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VFERDGRYIBXYRG-REVLRCOSSA-N (2s)-1-[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]propanoyl]pyrrolidine-2-carboxylic acid Chemical compound C([C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 VFERDGRYIBXYRG-REVLRCOSSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 241000725101 Clea Species 0.000 description 2
- 206010060891 General symptom Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 244000246386 Mentha pulegium Species 0.000 description 2
- 235000016257 Mentha pulegium Nutrition 0.000 description 2
- 235000004357 Mentha x piperita Nutrition 0.000 description 2
- 108010038807 Oligopeptides Proteins 0.000 description 2
- 102000015636 Oligopeptides Human genes 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
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- 235000013402 health food Nutrition 0.000 description 2
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 230000003308 immunostimulating effect Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 210000002751 lymph Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 101000984728 Chiropsoides quadrigatus Angiotensin-converting enzyme inhibitory peptide Proteins 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 241000589566 Elizabethkingia meningoseptica Species 0.000 description 1
- 102000005593 Endopeptidases Human genes 0.000 description 1
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- 239000004471 Glycine Substances 0.000 description 1
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- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- GRVMHFCZUIYNKQ-UFYCRDLUSA-N Phe-Phe-Val Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(O)=O GRVMHFCZUIYNKQ-UFYCRDLUSA-N 0.000 description 1
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- 102000056251 Prolyl Oligopeptidases Human genes 0.000 description 1
- 101710178372 Prolyl endopeptidase Proteins 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
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- 239000013543 active substance Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
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- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
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- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
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- 230000031891 intestinal absorption Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 230000007108 local immune response Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000005371 pilomotor reflex Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 150000003147 proline derivatives Chemical class 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
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Landscapes
- Non-Alcoholic Beverages (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61115674A JPS62270533A (ja) | 1986-05-20 | 1986-05-20 | 経口摂食物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61115674A JPS62270533A (ja) | 1986-05-20 | 1986-05-20 | 経口摂食物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62270533A JPS62270533A (ja) | 1987-11-24 |
| JPH0521092B2 true JPH0521092B2 (de) | 1993-03-23 |
Family
ID=14668483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61115674A Granted JPS62270533A (ja) | 1986-05-20 | 1986-05-20 | 経口摂食物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62270533A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001084948A1 (fr) | 2000-05-11 | 2001-11-15 | Kanebo, Limited | Compositions renfermant un peptide et un promoteur d'excretion electrolytique, et produits alimentaires contenant lesdites compositions |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2650955B1 (fr) * | 1989-08-16 | 1992-01-10 | Agronomique Inst Nat Rech | Procede d'obtention, a partir de la caseine beta, de fractions enrichies en peptides a activite biologique et les fractions peptidiques obtenues |
| JP3090950B2 (ja) * | 1994-04-19 | 2000-09-25 | 鐘紡株式会社 | 循環器系疾患予防剤 |
| KR0156678B1 (ko) | 1996-01-11 | 1998-10-15 | 이상윤 | 안지오텐신 전환효소 저해제 |
| JP2007529206A (ja) * | 2004-03-19 | 2007-10-25 | カンピーナ ネーダーランド ホールディング ビー．ブイ． | アンジオテンシン−ｉ−変換酵素阻害特性を有する食品成分及び食品の調製方法、並びにその方法により得られる製品 |
| WO2009033781A2 (en) * | 2007-09-11 | 2009-03-19 | Mondobiotech Laboratories Ag | Use of a peptide as a therapeutic agent |
| US20100204144A1 (en) * | 2007-09-11 | 2010-08-12 | Dorian Bevec | Use of the peptides maippkknqdk (cow kappa casein 106-116) and/or ygfqna (serorphin) as therapeutic agents |
| WO2009043524A2 (en) * | 2007-09-11 | 2009-04-09 | Mondobiotech Laboratories Ag | Use of a peptide as therapeutic agent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58109425A (ja) * | 1981-12-23 | 1983-06-29 | Agency Of Ind Science & Technol | アンジオテンシン転換酵素阻害剤 |
| JPS5944323A (ja) * | 1982-09-04 | 1984-03-12 | Agency Of Ind Science & Technol | アンジオテンシン転換酵素阻害剤 |
| JPS6117522A (ja) * | 1984-06-19 | 1986-01-25 | ローン‐プーラン・サント | 新規な生物学的に活性な物質及びそれを含有する組成物 |
| JPS6136226A (ja) * | 1984-07-28 | 1986-02-20 | Agency Of Ind Science & Technol | アンジオテンシン転換酵素阻害剤 |
-
1986
- 1986-05-20 JP JP61115674A patent/JPS62270533A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58109425A (ja) * | 1981-12-23 | 1983-06-29 | Agency Of Ind Science & Technol | アンジオテンシン転換酵素阻害剤 |
| JPS5944323A (ja) * | 1982-09-04 | 1984-03-12 | Agency Of Ind Science & Technol | アンジオテンシン転換酵素阻害剤 |
| JPS6117522A (ja) * | 1984-06-19 | 1986-01-25 | ローン‐プーラン・サント | 新規な生物学的に活性な物質及びそれを含有する組成物 |
| JPS6136226A (ja) * | 1984-07-28 | 1986-02-20 | Agency Of Ind Science & Technol | アンジオテンシン転換酵素阻害剤 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001084948A1 (fr) | 2000-05-11 | 2001-11-15 | Kanebo, Limited | Compositions renfermant un peptide et un promoteur d'excretion electrolytique, et produits alimentaires contenant lesdites compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62270533A (ja) | 1987-11-24 |
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