CA1090354A - Carboxymethylesters d'acides mercaptopropanoiques - Google Patents

Carboxymethylesters d'acides mercaptopropanoiques

Info

Publication number: CA1090354A
Authority: CA; Canada
Prior art keywords: hydrogen; acid; lower alkyl; compound; whenever prepared
Prior art date: 1977-07-14
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

Application number

CA306,339A

Other languages

English (en)

Inventor

Miguel A. Ondetti

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

Priority date (The priority date 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 date listed.)

1977-07-14

Filing date

1978-06-27

Publication date

1980-11-25

1978-06-27 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1980-11-25 Application granted granted Critical

1980-11-25 Publication of CA1090354A publication Critical patent/CA1090354A/fr

Status Expired legal-status Critical Current

Links

125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 title abstract description 3
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical class CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 title description 3
239000001257 hydrogen Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
125000000217 alkyl group Chemical group 0.000 claims abstract description 37
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 15
125000001589 carboacyl group Chemical group 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 25
150000002431 hydrogen Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
-1 3-indolylmethyl Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000006301 indolyl methyl group Chemical group 0.000 claims 2
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims 2
229940061720 alpha hydroxy acid Drugs 0.000 claims 1
150000001280 alpha hydroxy acids Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract 1
239000002220 antihypertensive agent Substances 0.000 abstract 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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 12
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 11
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
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
239000000908 ammonium hydroxide Substances 0.000 description 6
239000004310 lactic acid Substances 0.000 description 5
235000014655 lactic acid Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
229960002510 mandelic acid Drugs 0.000 description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 3
XGILAAMKEQUXLS-UHFFFAOYSA-N DL-3-indolelactic acid Natural products C1=CC=C2C(CC(O)C(O)=O)=CNC2=C1 XGILAAMKEQUXLS-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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
229910000343 potassium bisulfate Inorganic materials 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
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
102000015427 Angiotensins Human genes 0.000 description 2
108010064733 Angiotensins Proteins 0.000 description 2
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical group C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 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
229910021529 ammonia Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
SNZIFNXFAFKRKT-NSHDSACASA-N (2s)-2-azaniumyl-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoate Chemical compound CC(C)(C)OC1=CC=C(C[C@H]([NH3+])C([O-])=O)C=C1 SNZIFNXFAFKRKT-NSHDSACASA-N 0.000 description 1
VOXXWSYKYCBWHO-QMMMGPOBSA-N (S)-3-phenyllactic acid Chemical compound OC(=O)[C@@H](O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-QMMMGPOBSA-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
FVGFJAVRCMJGGQ-UHFFFAOYSA-N 2-hydroxy-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid Chemical group CC(C)(C)OC1=CC=C(CC(O)C(O)=O)C=C1 FVGFJAVRCMJGGQ-UHFFFAOYSA-N 0.000 description 1
XGILAAMKEQUXLS-JTQLQIEISA-N 3-(indol-3-yl) lactate Chemical group C1=CC=C2C(C[C@H](O)C(O)=O)=CNC2=C1 XGILAAMKEQUXLS-JTQLQIEISA-N 0.000 description 1
239000005541 ACE inhibitor Substances 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
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
102000004881 Angiotensinogen Human genes 0.000 description 1
108090001067 Angiotensinogen Proteins 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
239000004215 Carbon black (E152) Substances 0.000 description 1
VOXXWSYKYCBWHO-UHFFFAOYSA-N HO-Phe-OH Natural products OC(=O)C(O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical group C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-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
241000124008 Mammalia Species 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 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
230000003213 activating effect Effects 0.000 description 1
239000013543 active substance Substances 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
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 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 compound 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
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound 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
229930195733 hydrocarbon Natural products 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 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
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
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)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Indole Compounds (AREA)
Medical Treatment And Welfare Office Work (AREA)

CA306,339A 1977-07-14 1978-06-27 Carboxymethylesters d'acides mercaptopropanoiques Expired CA1090354A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81547277A	1977-07-14	1977-07-14
US815,472		1977-07-14

Publications (1)

Publication Number	Publication Date
CA1090354A true CA1090354A (fr)	1980-11-25

Family

ID=25217891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA306,339A Expired CA1090354A (fr)	1977-07-14	1978-06-27	Carboxymethylesters d'acides mercaptopropanoiques

Country Status (15)

Country	Link
JP (1)	JPS5419914A (fr)
AU (1)	AU522452B2 (fr)
BE (1)	BE869014A (fr)
CA (1)	CA1090354A (fr)
CH (1)	CH632490A5 (fr)
DE (1)	DE2830635A1 (fr)
DK (1)	DK149770C (fr)
FR (1)	FR2397401A1 (fr)
GB (1)	GB2001963B (fr)
HU (1)	HU177904B (fr)
IE (1)	IE47423B1 (fr)
IT (1)	IT1105098B (fr)
NL (1)	NL7807492A (fr)
NO (1)	NO146024C (fr)
SE (1)	SE7807821L (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1992000276A2 (fr) *	1990-06-22	1992-01-09	Fisons Plc	Inhibiteurs d'enzyme de conversion d'angotensine
WO2006016517A1 (fr) *	2004-08-13	2006-02-16	Kaneka Corporation	Procédé de production d’arylalcanoïque 2-substituant-oxy-3-(4-substituant-oxyphénil) optiquement actif

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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/fr 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 DE DE19782830635 patent/DE2830635A1/de active Granted
- 1978-07-12 HU HU78SU980A patent/HU177904B/hu unknown
- 1978-07-12 NL NL7807492A patent/NL7807492A/xx not_active Application Discontinuation
- 1978-07-13 FR FR7821086A patent/FR2397401A1/fr active Granted
- 1978-07-13 DK DK315378A patent/DK149770C/da not_active IP Right Cessation
- 1978-07-13 SE SE7807821A patent/SE7807821L/xx unknown
- 1978-07-13 NO NO782429A patent/NO146024C/no unknown
- 1978-07-14 JP JP8668378A patent/JPS5419914A/ja active Granted
- 1978-07-14 BE BE189300A patent/BE869014A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK315378A (da)	1979-01-15
IE781296L (en)	1979-01-14
NO146024C (no)	1982-07-14
DE2830635A1 (de)	1979-02-01
GB2001963A (en)	1979-02-14
SE7807821L (sv)	1979-01-15
DE2830635C2 (fr)	1988-06-23
NO146024B (no)	1982-04-05
IT1105098B (it)	1985-10-28
AU522452B2 (en)	1982-06-10
JPS6216943B2 (fr)	1987-04-15
FR2397401A1 (fr)	1979-02-09
DK149770C (da)	1987-03-09
DK149770B (da)	1986-09-29
HU177904B (en)	1982-01-28
GB2001963B (en)	1982-02-24
IT7850235A0 (it)	1978-07-10
JPS5419914A (en)	1979-02-15
AU3758878A (en)	1980-01-03
CH632490A5 (fr)	1982-10-15
BE869014A (fr)	1979-01-15
NO782429L (no)	1979-01-16
FR2397401B1 (fr)	1983-06-17
IE47423B1 (en)	1984-03-07
NL7807492A (nl)	1979-01-16

Publication	Publication Date	Title
US4108886A (en)	1978-08-22	Thiopropanoylamino acid derivatives
US4154935A (en)	1979-05-15	Halogen substituted mercaptoacylamino acids
US4070361A (en)	1978-01-24	Mercaptoalkylsulfonyl proline and pipecolic acid and esters thereof
CA1144931A (fr)	1983-04-19	Derives de l'acide pyroglutanique, et analogues
HU176021B (en)	1980-11-28	Process for producing substituted acylthio-derivatives of proline
JPS6121226B2 (fr)	1986-05-26
JPS6059226B2 (ja)	1985-12-24	プロリン誘導体および関連化合物
US4154934A (en)	1979-05-15	Mercaptoacylamino derivatives of heterocyclic carboxylic acids
JPS604815B2 (ja)	1985-02-06	プロリン誘導体
DE2904823A1 (de)	1979-08-16	Aminosaeurederivate und ihre salze sowie verfahren zu ihrer herstellung
WO1998018803A1 (fr)	1998-05-07	NOUVEAUX DERIVES D'(α-AMINOPHOSPHINO)PEPTIDES, LEUR PROCEDE DE PREPARATION ET LEURS APPLICATIONS THERAPEUTIQUES
CA1090354A (fr)	1980-11-25	Carboxymethylesters d'acides mercaptopropanoiques
EP0254354B1 (fr)	1993-03-31	Dérivés d'acide de thiazolidine-4-carboxylique à usage pharmaceutique
CA1124723A (fr)	1982-06-01	Mercaptoacylaminoprolines et acides pipecoliques a substitution par des halogenes
US4325886A (en)	1982-04-20	Optical resolution of acylthiopropionic acid
US4242265A (en)	1980-12-30	Indolylalkyl esters of mercaptoalkanoic acids
US4206122A (en)	1980-06-03	Derivatives of pyrrolidinecarboxaldehyde and piperidinecarboxaldehyde and intermediates therefor
DE69624365T2 (de)	2003-06-26	Penizillaminamid-derivate
US4611002A (en)	1986-09-09	Carboxymethyl esters of mercaptopropanoic acids as enkephalinase inhibitors
US4198509A (en)	1980-04-15	Mercaptoacylpiperazine carboxylic acid compounds
CA1109475A (fr)	1981-09-22	Derives d'acide thiopropanoylamine
FR2777780A1 (fr)	1999-10-29	Derives d'(alpha-aminophosphino) peptides, leur procede de preparation et les compositions qui les contiennent
US5166361A (en)	1992-11-24	Methods for preparing captopril and its analogues
CA1102812A (fr)	1981-06-09	Traduction non-disponible
KR800001133B1 (ko)	1980-10-12	복소환 치환기를 가진 5-설파모일벤조산 유도체의 제조방법

Legal Events

Date	Code	Title	Description
1997-11-25	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 19971125