CA1264500A - Derives de substitution en n d'amido-amino-acides - Google Patents

Derives de substitution en n d'amido-amino-acides

Info

Publication number: CA1264500A
Authority: CA; Canada
Prior art keywords: hydroxy; pharmaceutically acceptable; lower alkyl; alkyl; compound
Prior art date: 1981-03-30
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

Application number

CA000398031A

Other languages

English (en)

Other versions

CA1264500C (fr

Inventor

Jerry W. Skiles

Raymond D. Youssefyeh

John T. Suh

Howard Jones

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.)

USV Pharmaceutical Corp

Original Assignee

USV Pharmaceutical Corp

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.)

1981-03-30

Filing date

1982-03-10

Publication date

1990-01-16

1982-03-10 Application filed by USV Pharmaceutical Corp filed Critical USV Pharmaceutical Corp

1982-03-10 Priority to CA398031A priority Critical patent/CA1264500C/fr

1983-03-07 Priority to US06/472,551 priority patent/US4686295A/en

1990-01-16 Application granted granted Critical

1990-01-16 Publication of CA1264500A publication Critical patent/CA1264500A/fr

1990-01-16 Publication of CA1264500C publication Critical patent/CA1264500C/fr

Status Expired legal-status Critical Current

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 57
150000001875 compounds Chemical class 0.000 claims abstract description 57
150000003839 salts Chemical class 0.000 claims abstract description 34
125000003545 alkoxy group Chemical group 0.000 claims abstract description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
239000002253 acid Substances 0.000 claims abstract description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 16
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
206010020772 Hypertension Diseases 0.000 claims abstract description 11
230000002401 inhibitory effect Effects 0.000 claims abstract description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
230000001631 hypertensive effect Effects 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000005343 heterocyclic alkyl group Chemical group 0.000 claims abstract description 6
150000007513 acids Chemical class 0.000 claims abstract description 5
125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims abstract description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 3
-1 amino compound Chemical class 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
108010064733 Angiotensins Proteins 0.000 claims description 10
102000015427 Angiotensins Human genes 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 6
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
150000002466 imines Chemical class 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 3
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Chemical group C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 3
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 3
150000003573 thiols Chemical class 0.000 claims description 3
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 7
239000003937 drug carrier Substances 0.000 claims 7
239000008194 pharmaceutical composition Substances 0.000 claims 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 6
MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical group C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 2
125000000168 pyrrolyl group Chemical group 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
BXHJDQQMDNHJEJ-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;imidazolidine Chemical group C1CNCN1.C1CN=CN1 BXHJDQQMDNHJEJ-UHFFFAOYSA-N 0.000 claims 1
102000004190 Enzymes Human genes 0.000 abstract description 2
108090000790 Enzymes Proteins 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
239000004471 Glycine Substances 0.000 description 23
239000000047 product Substances 0.000 description 22
239000000243 solution Substances 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
239000012043 crude product Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
229960001866 silicon dioxide Drugs 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
229960003767 alanine Drugs 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
229910000039 hydrogen halide Inorganic materials 0.000 description 5
239000012433 hydrogen halide Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
229960000583 acetic acid Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
235000004279 alanine Nutrition 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
CANZBRDGRHNSGZ-NSHDSACASA-N (2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-NSHDSACASA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ILILFZXBRLXRAR-LURJTMIESA-N 2-[[(2s)-2-aminopropanoyl]-thiophen-3-ylamino]acetic acid Chemical compound C[C@H](N)C(=O)N(CC(O)=O)C=1C=CSC=1 ILILFZXBRLXRAR-LURJTMIESA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001024304 Mino Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001266 acyl halides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229950003188 isovaleryl diethylamide Drugs 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
PPKAIMDMNWBOKN-UHFFFAOYSA-N 2-Oxo-4-phenylbutyric acid Chemical compound OC(=O)C(=O)CCC1=CC=CC=C1 PPKAIMDMNWBOKN-UHFFFAOYSA-N 0.000 description 1
JZYTZBLAQBRLIM-LOACHALJSA-N 2-[[(2s)-1-[carboxymethyl(2,3-dihydro-1,4-benzodioxin-6-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]pentanedioic acid Chemical compound O1CCOC2=CC(N(CC(O)=O)C(=O)[C@@H](NC(CCC(O)=O)C(O)=O)CC(C)C)=CC=C21 JZYTZBLAQBRLIM-LOACHALJSA-N 0.000 description 1
SUQOLLHJECOHJX-CABZTGNLSA-N 2-[[(2s,3s)-2-amino-3-methylpentanoyl]-pyridin-3-ylamino]acetic acid Chemical compound CC[C@H](C)[C@H](N)C(=O)N(CC(O)=O)C1=CC=CN=C1 SUQOLLHJECOHJX-CABZTGNLSA-N 0.000 description 1
VQGGYDRIOOWRIF-UHFFFAOYSA-N 2-aminoacetic acid;dihydrochloride Chemical compound Cl.Cl.NCC(O)=O VQGGYDRIOOWRIF-UHFFFAOYSA-N 0.000 description 1
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000009581 Balanites aegyptiaca Nutrition 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101100134929 Gallus gallus COR9 gene Proteins 0.000 description 1
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
101100537948 Mus musculus Trir gene Proteins 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
USPFMEKVPDBMCG-LBPRGKRZSA-N N-benzyloxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 USPFMEKVPDBMCG-LBPRGKRZSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000428533 Rhis Species 0.000 description 1
241000231739 Rutilus rutilus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
YHXLLDYZEJLHGZ-CABZTGNLSA-N [2-(pyridin-3-ylamino)acetyl] (2s,3s)-2-amino-3-methylpentanoate Chemical compound CC[C@H](C)[C@H](N)C(=O)OC(=O)CNC1=CC=CN=C1 YHXLLDYZEJLHGZ-CABZTGNLSA-N 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
PWUBONDMIMDOQY-UHFFFAOYSA-N acetonitrile;hydrochloride Chemical compound Cl.CC#N PWUBONDMIMDOQY-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
230000004075 alteration Effects 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
XVHSJXQEAPULNL-UHFFFAOYSA-N benzyl 2-(pyrimidin-2-ylamino)acetate Chemical compound C=1C=CC=CC=1COC(=O)CNC1=NC=CC=N1 XVHSJXQEAPULNL-UHFFFAOYSA-N 0.000 description 1
IZZIPPQWYVRGRS-UHFFFAOYSA-N benzyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OCC1=CC=CC=C1 IZZIPPQWYVRGRS-UHFFFAOYSA-N 0.000 description 1
GRSTVVGJSKHCCS-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanone Chemical class N=1C=CNC=1C(=O)C1=NC=CN1 GRSTVVGJSKHCCS-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
CMDKPGRTAQVGFQ-RMKNXTFCSA-N cinoxate Chemical compound CCOCCOC(=O)\C=C\C1=CC=C(OC)C=C1 CMDKPGRTAQVGFQ-RMKNXTFCSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
MMTCTSLQNOZPGL-UHFFFAOYSA-N ethyl 2-(pyridin-3-ylamino)acetate Chemical compound CCOC(=O)CNC1=CC=CN=C1 MMTCTSLQNOZPGL-UHFFFAOYSA-N 0.000 description 1
MGSWAHQQBHNCEI-UHFFFAOYSA-N ethyl 4-methyl-2-oxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)C MGSWAHQQBHNCEI-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
KDFBGNBTTMPNIG-UHFFFAOYSA-N hydron;2-(1h-indol-3-yl)ethanamine;chloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1 KDFBGNBTTMPNIG-UHFFFAOYSA-N 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000002114 valyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Peptides Or Proteins (AREA)

CA398031A 1981-03-30 1982-03-10 Derives de substitution en n d'amido-amino-acides Expired CA1264500C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA398031A CA1264500C (fr)	1981-03-30	1982-03-10	Derives de substitution en n d'amido-amino-acides
US06/472,551 US4686295A (en)	1982-03-10	1983-03-07	N-carboxy anhydride intermediates

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US24905381A	1981-03-30	1981-03-30
CA398031A CA1264500C (fr)	1981-03-30	1982-03-10	Derives de substitution en n d'amido-amino-acides
US249,053		1988-09-26

Publications (2)

Publication Number	Publication Date
CA1264500A true CA1264500A (fr)	1990-01-16
CA1264500C CA1264500C (fr)	1990-01-16

Family

ID=86548567

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA398031A Expired CA1264500C (fr)	1981-03-30	1982-03-10	Derives de substitution en n d'amido-amino-acides

Country Status (1)

Country	Link
CA (1)	CA1264500C (fr)

1982
- 1982-03-10 CA CA398031A patent/CA1264500C/fr not_active Expired

Also Published As

Publication number	Publication date
CA1264500C (fr)	1990-01-16

Legal Events

Date	Code	Title	Description
1998-01-20	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 19980120

Publication	Publication Date	Title
CA1302005C (fr)	1992-05-26	Derives d'acides amines utilises comme antihypertenseurs
US4820729A (en)	1989-04-11	N-substituted-amido-amino acids
US4350704A (en)	1982-09-21	Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids
US4496542A (en)	1985-01-29	N-substituted-amido-amino acids
CA1060435A (fr)	1979-08-14	Reptides
KR850001269B1 (ko)	1985-09-04	아미노산 유도체의 제조방범
CA1288547C (fr)	1991-09-03	Derives de l'acide amine 1-(3-mercapto-2-methylpropanol) prolyl et leurs sels, procedes pour leur preparation et compositions pharmaceutiques en contenant
CA1205476A (fr)	1986-06-03	Derives de substitution acyles d'acides actahydro-1h-indole-2-carboxyliques
US4668797A (en)	1987-05-26	Bicyclic aminoacids as intermediates and processes for their preparation
NZ333904A (en)	2000-06-23	VLA-4 and IIb/IIIa cell adhesion inhibitors
JPWO1995009864A1 (ja)	1996-02-27	新規なペプチド誘導体
KR100694528B1 (ko)	2007-03-13	2,5-디옥소-옥사졸리딘 중간체 화합물을 사용한, 페린도프릴 및 이의 염의 제조방법
KR890001146B1 (ko)	1989-04-25	아미도-아미노산 및 그의 제조 방법
HU181087B (en)	1983-05-30	Process for producing mercapto-acyl-dipeptides
US4425355A (en)	1984-01-10	Substituted acyl derivatives of chair form of octahydro-1H-indole-2-carboxylic acids
EP0061768B1 (fr)	1986-05-14	Dipeptides N-amido substitués
EP0103077B1 (fr)	1988-05-18	Dipeptides substitués, leurs procédés de préparation, compositions pharmaceutiques les contenant et méthode de préparation de ces compositions pharmaceutiques
FR2585709A1 (fr)	1987-02-06	Nouveaux derives peptidiques a structure lactonique ou cycloamidique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA1264500A (fr)	1990-01-16	Derives de substitution en n d'amido-amino-acides
US4490386A (en)	1984-12-25	Phosphate salts of 1-[2-[(1-alkoxycarbonyl-3-aralkyl)-amino]-1-oxoalkyl]octahydro-1H-indole-2-carboxylic acids, preparation of, and medical compositions thereof
NZ233811A (en)	1992-10-28	Amino-substituted heterocycles having renin inhibitory action
US4558038A (en)	1985-12-10	N-Substituted-amindo-amino acids
US4503043A (en)	1985-03-05	Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids
CA2015827A1 (fr)	1990-11-02	Derives d'acides amines inhibiteurs de la renine
US4595675A (en)	1986-06-17	Bicyclic α-iminocarboxylic acid compounds having hypotensive activity