JPS6216943B2 - - Google Patents
Info
- Publication number
- JPS6216943B2 JPS6216943B2 JP53086683A JP8668378A JPS6216943B2 JP S6216943 B2 JPS6216943 B2 JP S6216943B2 JP 53086683 A JP53086683 A JP 53086683A JP 8668378 A JP8668378 A JP 8668378A JP S6216943 B2 JPS6216943 B2 JP S6216943B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydrogen
- compound according
- compound
- formula
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- -1 3-indolylmethyl Chemical group 0.000 claims description 15
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000006301 indolyl methyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- 239000002253 acid Substances 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XGILAAMKEQUXLS-UHFFFAOYSA-N 3-(indol-3-yl)lactic acid Chemical compound C1=CC=C2C(CC(O)C(O)=O)=CNC2=C1 XGILAAMKEQUXLS-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- UZEGMBFBQIDPHQ-UHFFFAOYSA-N (2-hydroxyacetyl) 3-acetylsulfanyl-2-methylpropanoate Chemical compound CC(=O)SCC(C)C(=O)OC(=O)CO UZEGMBFBQIDPHQ-UHFFFAOYSA-N 0.000 description 3
- PEOGPKAGXDGMIK-UHFFFAOYSA-N (2-hydroxyacetyl) 3-sulfanylpropanoate Chemical compound OCC(=O)OC(=O)CCS PEOGPKAGXDGMIK-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229940061720 alpha hydroxy acid Drugs 0.000 description 3
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VOXXWSYKYCBWHO-QMMMGPOBSA-N (S)-3-phenyllactic acid Chemical compound OC(=O)[C@@H](O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-QMMMGPOBSA-N 0.000 description 2
- VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 2
- AYQXANXXZYKTDL-UHFFFAOYSA-N 3-acetylsulfanylpropanoic acid Chemical compound CC(=O)SCCC(O)=O AYQXANXXZYKTDL-UHFFFAOYSA-N 0.000 description 2
- VOXXWSYKYCBWHO-UHFFFAOYSA-N 3-phenyllactic acid Chemical compound OC(=O)C(O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-UHFFFAOYSA-N 0.000 description 2
- 239000005541 ACE inhibitor Substances 0.000 description 2
- 102000015427 Angiotensins Human genes 0.000 description 2
- 108010064733 Angiotensins Proteins 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NWCHELUCVWSRRS-SECBINFHSA-N (2r)-2-hydroxy-2-phenylpropanoic acid Chemical compound OC(=O)[C@@](O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-SECBINFHSA-N 0.000 description 1
- 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 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 1
- XGILAAMKEQUXLS-JTQLQIEISA-N 3-(indol-3-yl) lactate Chemical compound C1=CC=C2C(C[C@H](O)C(O)=O)=CNC2=C1 XGILAAMKEQUXLS-JTQLQIEISA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 1
- 102000004881 Angiotensinogen Human genes 0.000 description 1
- 108090001067 Angiotensinogen Proteins 0.000 description 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 1
- SZAWPEWXKVAYDZ-UHFFFAOYSA-N C(C)(=O)CCC(=S)OC(CO)=O Chemical compound C(C)(=O)CCC(=S)OC(CO)=O SZAWPEWXKVAYDZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medical Treatment And Welfare Office Work (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81547277A | 1977-07-14 | 1977-07-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5419914A JPS5419914A (en) | 1979-02-15 |
| JPS6216943B2 true JPS6216943B2 (ko) | 1987-04-15 |
Family
ID=25217891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8668378A Granted JPS5419914A (en) | 1977-07-14 | 1978-07-14 | Mercaptopropanate carboxymethylesters and process for preparing same |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5419914A (ko) |
| AU (1) | AU522452B2 (ko) |
| BE (1) | BE869014A (ko) |
| CA (1) | CA1090354A (ko) |
| CH (1) | CH632490A5 (ko) |
| DE (1) | DE2830635A1 (ko) |
| DK (1) | DK149770C (ko) |
| FR (1) | FR2397401A1 (ko) |
| GB (1) | GB2001963B (ko) |
| HU (1) | HU177904B (ko) |
| IE (1) | IE47423B1 (ko) |
| IT (1) | IT1105098B (ko) |
| NL (1) | NL7807492A (ko) |
| NO (1) | NO146024C (ko) |
| SE (1) | SE7807821L (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0535042B1 (en) * | 1990-06-22 | 1995-03-29 | FISONS plc | Angiotensis converting enzyme inhibitors |
| US20090029429A1 (en) * | 2004-08-13 | 2009-01-29 | Kaneka Corporation | Process for Producing Optically Active 2-Substituent-Oxy-3-(4-Substituent-Oxyphenyl) Propionic Acid Derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1527919A (fr) * | 1967-03-23 | 1968-06-07 | Nouveaux dérivés de l'acide salicylique | |
| BE793887A (fr) * | 1972-01-12 | 1973-07-11 | Hoffmann La Roche | Derives acyles |
-
1978
- 1978-06-27 CA CA306,339A patent/CA1090354A/en not_active Expired
- 1978-06-28 IE IE1296/78A patent/IE47423B1/en not_active IP Right Cessation
- 1978-06-29 AU AU37588/78A patent/AU522452B2/en not_active Expired
- 1978-07-05 GB GB7828882A patent/GB2001963B/en not_active Expired
- 1978-07-10 IT IT50235/78A patent/IT1105098B/it active
- 1978-07-11 CH CH753578A patent/CH632490A5/fr not_active IP Right Cessation
- 1978-07-12 HU HU78SU980A patent/HU177904B/hu unknown
- 1978-07-12 NL NL7807492A patent/NL7807492A/xx not_active Application Discontinuation
- 1978-07-12 DE DE19782830635 patent/DE2830635A1/de active Granted
- 1978-07-13 NO NO782429A patent/NO146024C/no unknown
- 1978-07-13 DK DK315378A patent/DK149770C/da not_active IP Right Cessation
- 1978-07-13 FR FR7821086A patent/FR2397401A1/fr active Granted
- 1978-07-13 SE SE7807821A patent/SE7807821L/xx unknown
- 1978-07-14 BE BE189300A patent/BE869014A/xx not_active IP Right Cessation
- 1978-07-14 JP JP8668378A patent/JPS5419914A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK149770C (da) | 1987-03-09 |
| DK149770B (da) | 1986-09-29 |
| AU3758878A (en) | 1980-01-03 |
| DK315378A (da) | 1979-01-15 |
| GB2001963A (en) | 1979-02-14 |
| IT7850235A0 (it) | 1978-07-10 |
| NO782429L (no) | 1979-01-16 |
| JPS5419914A (en) | 1979-02-15 |
| AU522452B2 (en) | 1982-06-10 |
| IT1105098B (it) | 1985-10-28 |
| FR2397401B1 (ko) | 1983-06-17 |
| IE781296L (en) | 1979-01-14 |
| HU177904B (en) | 1982-01-28 |
| SE7807821L (sv) | 1979-01-15 |
| NO146024C (no) | 1982-07-14 |
| NL7807492A (nl) | 1979-01-16 |
| NO146024B (no) | 1982-04-05 |
| GB2001963B (en) | 1982-02-24 |
| FR2397401A1 (fr) | 1979-02-09 |
| CA1090354A (en) | 1980-11-25 |
| DE2830635A1 (de) | 1979-02-01 |
| IE47423B1 (en) | 1984-03-07 |
| DE2830635C2 (ko) | 1988-06-23 |
| CH632490A5 (fr) | 1982-10-15 |
| BE869014A (fr) | 1979-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4108886A (en) | Thiopropanoylamino acid derivatives | |
| HU176021B (en) | Process for producing substituted acylthio-derivatives of proline | |
| JPS6121226B2 (ko) | ||
| FR2517302A1 (fr) | Esters et amides de 13 14-bisdehydroprostaglandines | |
| EP1009750A1 (fr) | NOUVEAUX DERIVES D'($g(a)-AMINOPHOSPHINO)PEPTIDES, LEUR PROCEDE DE PREPARATION ET LEURS APPLICATIONS THERAPEUTIQUES | |
| EP2326616B1 (en) | Process for the synthesis of ezetimibe and intermediates useful therefore | |
| Alcaraz et al. | Asymmetric syntheses of 1-amino-2-phenyl (alkyl) cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines | |
| EP1272454B1 (fr) | Procede de synthese des esters de la n-[(s)-1-carboxybutyl]-(s)-alanine et application a la synthese du perindopril | |
| JPS6216943B2 (ko) | ||
| FR2551063A1 (fr) | Nouveaux dimethyl-2,5 pyrroles, leur procede de preparation et leur application en therapeutique | |
| JPH06184069A (ja) | α−ヒドロキシ−β−アミノカルボン酸の製造方法 | |
| US4242265A (en) | Indolylalkyl esters of mercaptoalkanoic acids | |
| JPH1087633A (ja) | キラルなコハク酸誘導体の製造方法 | |
| WO2004083237A1 (fr) | NOUVEAU PROCEDE DE SYNTHESE DE L’ACIDE (2S, 3aS, 7aS)-PERHYDROINDOLE-2-CARBOXYLIQUE ET DE SES ESTERS, ET APPLICATION A LA SYNTHESE DU PERINDOPRIL | |
| FR2777780A1 (fr) | Derives d'(alpha-aminophosphino) peptides, leur procede de preparation et les compositions qui les contiennent | |
| JPH0128019B2 (ko) | ||
| CA1109475A (en) | Thiopropanoylamino acid derivatives | |
| US4385062A (en) | 1-[(-2-Mercaptocycloalkyl)carbonyl]-L-proline derivatives, the process for their manufacture, the intermediates for their synthesis and their use as anti-hypertensive agents | |
| EP0599732B1 (fr) | Dérivés de 1-phénylbicyclo[2.2.2]octane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| US4766127A (en) | 2-(3-pyridylmethyl)naphthalene-6-carboxylic acid as a thromboxane synthetase inhibitor | |
| LU82115A1 (fr) | Nouvelles quinazolines anti-hypertensives,leur procede de production et composition pharmaceutique les contenant | |
| JP2741441B2 (ja) | Ｎ−アルキル−チアゾリジン誘導体 | |
| HU207711B (en) | Process for producing glutaric acid derivatives | |
| US4496743A (en) | 1-[(Acylthiocycloalkyl)carbonyl]-L-proline derivatives | |
| JPH05501561A (ja) | 新規３，３，５―トリメチルシクロヘキシル ２―メチルプロピオン酸誘導体、その製造方法及びそれらを内包する治療用組成物 |