NL8001675A - Mercaptoacyldipeptiden. - Google Patents
Mercaptoacyldipeptiden. Download PDFInfo
- Publication number
- NL8001675A NL8001675A NL8001675A NL8001675A NL8001675A NL 8001675 A NL8001675 A NL 8001675A NL 8001675 A NL8001675 A NL 8001675A NL 8001675 A NL8001675 A NL 8001675A NL 8001675 A NL8001675 A NL 8001675A
- Authority
- NL
- Netherlands
- Prior art keywords
- proline
- alanyl
- methyl
- formula
- oxopropyl
- Prior art date
Links
- 108010016626 Dipeptides Proteins 0.000 title claims description 5
- -1 N- (Acetylthioacetyl) glycyl Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 37
- 229960002429 proline Drugs 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 229960003767 alanine Drugs 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229960002591 hydroxyproline Drugs 0.000 claims description 7
- 239000004471 Glycine Substances 0.000 claims description 5
- 229960002449 glycine Drugs 0.000 claims description 5
- 229910003002 lithium salt Inorganic materials 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- 229930182821 L-proline Natural products 0.000 claims description 4
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229960004799 tryptophan Drugs 0.000 claims description 3
- RNXKXUOGQKYKTH-AKGZTFGVSA-N (2s)-4-methoxypyrrolidine-2-carboxylic acid Chemical compound COC1CN[C@H](C(O)=O)C1 RNXKXUOGQKYKTH-AKGZTFGVSA-N 0.000 claims description 2
- WRHPVRWALQQWHH-YFKPBYRVSA-N (8s)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylic acid Chemical compound C1N[C@H](C(=O)O)CC21OCCO2 WRHPVRWALQQWHH-YFKPBYRVSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 2
- 229950001139 timonacic Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960003136 leucine Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229960004295 valine Drugs 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
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- 239000000243 solution Substances 0.000 description 49
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 35
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- 239000000203 mixture Substances 0.000 description 26
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 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 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- QPLPMPAMOJIAMN-UHFFFAOYSA-N 3-oxobutanethioic s-acid Chemical compound CC(=O)CC(O)=S QPLPMPAMOJIAMN-UHFFFAOYSA-N 0.000 description 12
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 230000010933 acylation Effects 0.000 description 9
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- 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 4
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- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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- 238000001665 trituration Methods 0.000 description 2
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
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- KZNQNBZMBZJQJO-YFKPBYRVSA-N glyclproline Chemical compound NCC(=O)N1CCC[C@H]1C(O)=O KZNQNBZMBZJQJO-YFKPBYRVSA-N 0.000 description 1
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- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
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- 159000000002 lithium salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- KQTYXKRCHXEGPS-ZANVPECISA-N methyl (2s)-2-[[(2s)-2-aminopropanoyl]amino]-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@@H](C(=O)OC)NC(=O)[C@H](C)N)=CNC2=C1 KQTYXKRCHXEGPS-ZANVPECISA-N 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
- 230000007935 neutral effect Effects 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
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- 239000003981 vehicle 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
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
-
- 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
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- 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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2570179A | 1979-04-02 | 1979-04-02 | |
| US2570179 | 1979-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8001675A true NL8001675A (nl) | 1980-10-06 |
Family
ID=21827594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001675A NL8001675A (nl) | 1979-04-02 | 1980-03-21 | Mercaptoacyldipeptiden. |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS55133345A (forum.php) |
| AT (1) | AT373577B (forum.php) |
| AU (1) | AU537592B2 (forum.php) |
| BE (1) | BE882601A (forum.php) |
| CH (1) | CH645092A5 (forum.php) |
| DE (1) | DE3012140A1 (forum.php) |
| DK (1) | DK140480A (forum.php) |
| ES (1) | ES8104200A1 (forum.php) |
| FR (1) | FR2453135A1 (forum.php) |
| GB (1) | GB2045771B (forum.php) |
| GR (1) | GR67752B (forum.php) |
| HU (1) | HU181087B (forum.php) |
| IE (1) | IE49653B1 (forum.php) |
| IT (1) | IT1147332B (forum.php) |
| LU (1) | LU82316A1 (forum.php) |
| NL (1) | NL8001675A (forum.php) |
| NO (1) | NO150360C (forum.php) |
| NZ (1) | NZ193142A (forum.php) |
| PH (1) | PH22024A (forum.php) |
| PT (1) | PT71044A (forum.php) |
| SE (1) | SE8002512L (forum.php) |
| ZA (1) | ZA801527B (forum.php) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5692848A (en) * | 1979-12-27 | 1981-07-27 | Dainippon Pharmaceut Co Ltd | Preparation of 1- 3-lower alaknoylthio-2-methylpropanoyl prolylphenylalanine |
| JPS56139455A (en) | 1980-04-02 | 1981-10-30 | Santen Pharmaceut Co Ltd | Sulfur-containing acylaminoacid |
| US4336950A (en) * | 1980-09-08 | 1982-06-29 | John Zepkowski | Sled |
| US4462943A (en) * | 1980-11-24 | 1984-07-31 | E. R. Squibb & Sons, Inc. | Carboxyalkyl amino acid derivatives of various substituted prolines |
| JPS57142967A (en) * | 1981-02-27 | 1982-09-03 | Dainippon Pharmaceut Co Ltd | N-(acylthioalkanoyloxy)succinimide and its use |
| US4512979A (en) * | 1981-03-23 | 1985-04-23 | Merck & Co., Inc. | Dipeptides containing thialysine and related amino acids as antihypertensives |
| US4382081A (en) * | 1981-06-12 | 1983-05-03 | E. R. Squibb & Sons, Inc. | Inhibitors of mammalian collagenase |
| IT1195287B (it) * | 1981-11-05 | 1988-10-12 | Ausonia Farma Srl | Derivato tiazolico,procedimento per la sua preparazione e relative composizioni farmaceutiche |
| US4434151A (en) * | 1982-11-08 | 1984-02-28 | Medi-Physics, Inc. | Bifunctional chelating agents |
| DE3243369A1 (de) * | 1982-11-24 | 1984-05-24 | Basf Ag, 6700 Ludwigshafen | Bis-(benzoylthio)-carbonsaeuren, ihre herstellung und verwendung zur herstellung von wirkstoffen |
| US4642355A (en) * | 1984-02-24 | 1987-02-10 | Otsuka Pharmaceutical Factory, Inc. | Proline derivatives |
| US4560506A (en) * | 1984-05-25 | 1985-12-24 | E. R. Squibb & Sons, Inc. | Mercaptocycloalkylcarbonyl and mercaptoarylcarbonyl dipeptides |
| DE3432307A1 (de) * | 1984-09-03 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Aminosaeurederivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| DE3436569A1 (de) * | 1984-10-05 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Aminosaeurederivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| US4894437A (en) * | 1985-11-15 | 1990-01-16 | The Upjohn Company | Novel renin inhibiting polypeptide analogs containing S-aryl-D- or L- or DL-cysteinyl, 3-(arylthio)lactic acid or 3-(arylthio)alkyl moieties |
| EP0245361A1 (en) * | 1985-11-15 | 1987-11-19 | The Upjohn Company | Novel renin inhibiting polypeptide analogs containing s-aryl-d- or l- or dl-cysteinyl, 3-(arylthio)lactic acid or 3-(arylthio)alkyl moieties |
| JPH0662671B2 (ja) * | 1986-01-17 | 1994-08-17 | 株式会社大塚製薬工場 | プロリン誘導体 |
| EP0500989B1 (en) * | 1991-02-27 | 1998-12-09 | Lacer, S.A. | N-(alpha-substituted-pyridinyl) carbonyl dipeptide antihypertensive agents |
| FR2679564A1 (fr) * | 1991-07-23 | 1993-01-29 | Inst Nat Sante Rech Med | Nouveaux acylmercaptoalcanoldipeptides, leur preparation et les compositions qui les contiennent. |
| US5504080A (en) * | 1992-10-28 | 1996-04-02 | Bristol-Myers Squibb Co. | Benzo-fused lactams |
| GB9310075D0 (en) * | 1993-05-17 | 1993-06-30 | Fujisawa Pharmaceutical Co | New mercapto-amide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| US7390789B2 (en) * | 2005-09-13 | 2008-06-24 | William H Simmons | Thio-containing inhibitors of aminopeptidase P, and compositions thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS559058A (en) * | 1978-07-06 | 1980-01-22 | Dainippon Pharmaceut Co Ltd | 1-(3-mercapto-2-methylpropanoyl)prolyl amino acid derivative |
-
1980
- 1980-03-12 AU AU56380/80A patent/AU537592B2/en not_active Ceased
- 1980-03-14 ZA ZA00801527A patent/ZA801527B/xx unknown
- 1980-03-14 GB GB8008696A patent/GB2045771B/en not_active Expired
- 1980-03-17 NZ NZ193142A patent/NZ193142A/en unknown
- 1980-03-17 PH PH23775A patent/PH22024A/en unknown
- 1980-03-18 GR GR61475A patent/GR67752B/el unknown
- 1980-03-21 NL NL8001675A patent/NL8001675A/nl not_active Application Discontinuation
- 1980-03-26 FR FR8006711A patent/FR2453135A1/fr active Granted
- 1980-03-28 DE DE19803012140 patent/DE3012140A1/de not_active Withdrawn
- 1980-03-28 IE IE638/80A patent/IE49653B1/en not_active IP Right Cessation
- 1980-03-31 NO NO800931A patent/NO150360C/no unknown
- 1980-04-01 PT PT71044A patent/PT71044A/pt not_active IP Right Cessation
- 1980-04-01 CH CH257180A patent/CH645092A5/de not_active IP Right Cessation
- 1980-04-01 SE SE8002512A patent/SE8002512L/xx not_active Application Discontinuation
- 1980-04-01 ES ES490166A patent/ES8104200A1/es not_active Expired
- 1980-04-01 DK DK140480A patent/DK140480A/da not_active IP Right Cessation
- 1980-04-01 LU LU82316A patent/LU82316A1/fr unknown
- 1980-04-01 IT IT21110/80A patent/IT1147332B/it active
- 1980-04-01 HU HU8080774A patent/HU181087B/hu not_active IP Right Cessation
- 1980-04-02 JP JP4402080A patent/JPS55133345A/ja active Pending
- 1980-04-02 BE BE0/200091A patent/BE882601A/fr not_active IP Right Cessation
- 1980-04-02 AT AT0179480A patent/AT373577B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE882601A (fr) | 1980-10-02 |
| PH22024A (en) | 1988-05-13 |
| IT8021110A0 (it) | 1980-04-01 |
| AU537592B2 (en) | 1984-07-05 |
| SE8002512L (sv) | 1980-10-03 |
| ES490166A0 (es) | 1981-04-01 |
| AT373577B (de) | 1984-02-10 |
| GB2045771A (en) | 1980-11-05 |
| IE800638L (en) | 1980-10-02 |
| ES8104200A1 (es) | 1981-04-01 |
| HU181087B (en) | 1983-05-30 |
| LU82316A1 (fr) | 1980-12-16 |
| IT1147332B (it) | 1986-11-19 |
| ATA179480A (de) | 1983-06-15 |
| ZA801527B (en) | 1981-03-25 |
| AU5638080A (en) | 1980-10-09 |
| JPS55133345A (en) | 1980-10-17 |
| NO150360C (no) | 1984-10-03 |
| CH645092A5 (de) | 1984-09-14 |
| IE49653B1 (en) | 1985-11-13 |
| DE3012140A1 (de) | 1980-10-23 |
| FR2453135B1 (forum.php) | 1983-06-17 |
| NZ193142A (en) | 1984-08-24 |
| PT71044A (en) | 1980-05-01 |
| NO800931L (no) | 1980-10-03 |
| DK140480A (da) | 1980-10-03 |
| GB2045771B (en) | 1983-01-26 |
| FR2453135A1 (fr) | 1980-10-31 |
| GR67752B (forum.php) | 1981-09-18 |
| NO150360B (no) | 1984-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |