CH658455A5 - Peptidderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel. - Google Patents

Peptidderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel. Download PDF

Info

Publication number: CH658455A5
Authority: CH; Switzerland
Prior art keywords: carboxylic acid; tetrahydroisoquinoline; alanyl; carboethoxy; mmol
Prior art date: 1981-03-19

Application number

CH1691/82A

Other languages

German (de)

English (en)

Inventor

John T Suh

Jeffrey N Barton

John R Regan

Original Assignee

Usv Pharma 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.)

1981-03-19

Filing date

1982-03-18

Publication date

1986-11-14

1982-03-18 Application filed by Usv Pharma Corp filed Critical Usv Pharma Corp

1986-11-14 Publication of CH658455A5 publication Critical patent/CH658455A5/de

Links

238000000034 method Methods 0.000 title description 13
108090000765 processed proteins & peptides Proteins 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 2
239000003814 drug Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 description 34
239000000243 solution Substances 0.000 description 29
-1 phenylmercapto Chemical group 0.000 description 26
239000000047 product Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
125000000217 alkyl group Chemical group 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 17
239000002253 acid Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
108010016626 Dipeptides Proteins 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
229910052736 halogen Inorganic materials 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
150000002367 halogens Chemical group 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000004108 freeze drying Methods 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 7
125000003282 alkyl amino group Chemical group 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
FVZLXIARAAOVCZ-UHFFFAOYSA-N 1h-azepine-3-carboxylic acid Chemical compound OC(=O)C1=CNC=CC=C1 FVZLXIARAAOVCZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
125000004103 aminoalkyl group Chemical group 0.000 description 6
125000001188 haloalkyl group Chemical group 0.000 description 6
125000002768 hydroxyalkyl group Chemical group 0.000 description 6
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 6
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 5
125000000304 alkynyl group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
238000004255 ion exchange chromatography Methods 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
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 3
206010020772 Hypertension Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000001980 alanyl group Chemical group 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
238000000262 chemical ionisation mass spectrometry Methods 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000005358 mercaptoalkyl group Chemical group 0.000 description 3
239000003921 oil Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000005932 reductive alkylation reaction Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical group C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
ZNGKQGXJBGWXGJ-ARTQYDKTSA-N 1-[(2s)-2-aminopropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)[C@@H](N)C)NC(C(O)=O)CC2=C1 ZNGKQGXJBGWXGJ-ARTQYDKTSA-N 0.000 description 2
CMFCCYFQTHPJKO-UHFFFAOYSA-N 3-benzyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)C(CC)CC1=CC=CC=C1 CMFCCYFQTHPJKO-UHFFFAOYSA-N 0.000 description 2
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
YYTAYINRPUJPNH-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1NCCC2=CC(OC)=CC=C21 YYTAYINRPUJPNH-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001266 acyl halides Chemical class 0.000 description 2
229960003767 alanine Drugs 0.000 description 2
235000004279 alanine Nutrition 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000004350 aryl cycloalkyl group Chemical group 0.000 description 2
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
RKJMHZBROOPSPU-UHFFFAOYSA-N methyl 1h-azepine-3-carboxylate Chemical compound COC(=O)C1=CNC=CC=C1 RKJMHZBROOPSPU-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
JSHXJPFZKBRLFU-JQWIXIFHSA-N (2s,3s)-3-methyl-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 JSHXJPFZKBRLFU-JQWIXIFHSA-N 0.000 description 1
BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 description 1
KQGLRUWMEAYUAU-PNORIONUSA-N 1-[(2S)-2-[(1-carboxy-2,3-dihydro-1H-inden-2-yl)methylamino]propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C(=O)(O)C1C(CC2=CC=CC=C12)CN[C@@H](C)C(=O)C1NC(CC2=CC=CC=C12)C(=O)O KQGLRUWMEAYUAU-PNORIONUSA-N 0.000 description 1
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 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
GGHNMLNTPITMPF-UHFFFAOYSA-N 2-oxo-4-phenylbutanoic acid hydrate Chemical compound O.C(C1=CC=CC=C1)CC(C(=O)O)=O GGHNMLNTPITMPF-UHFFFAOYSA-N 0.000 description 1
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 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
BKAJNAXTPSGJCU-UHFFFAOYSA-N 4-methyl-2-oxopentanoic acid Chemical compound CC(C)CC(=O)C(O)=O BKAJNAXTPSGJCU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
108010064733 Angiotensins Proteins 0.000 description 1
102000015427 Angiotensins Human genes 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ILBMALMWUZCCRW-CYWKSYIRSA-N C(=O)(O)C(C)N1C(C2=CC=CC=C2CC1)(C(=O)O)C([C@@H](N)C)=O Chemical compound C(=O)(O)C(C)N1C(C2=CC=CC=C2CC1)(C(=O)O)C([C@@H](N)C)=O ILBMALMWUZCCRW-CYWKSYIRSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000003978 alpha-halocarboxylic acids Chemical class 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229940064734 aminobenzoate Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 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
239000012223 aqueous fraction Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
YMXDJQBRIWOQOB-UHFFFAOYSA-N benzyl 2,3-dihydro-1h-indole-2-carboxylate Chemical compound C1C2=CC=CC=C2NC1C(=O)OCC1=CC=CC=C1 YMXDJQBRIWOQOB-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
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical class C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000004985 dialkyl amino alkyl 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
LRLJUGFKJBKGTR-UHFFFAOYSA-N ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)OCC)NCCC2=C1 LRLJUGFKJBKGTR-UHFFFAOYSA-N 0.000 description 1
STPXIOGYOLJXMZ-UHFFFAOYSA-N ethyl 2-oxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CCC1=CC=CC=C1 STPXIOGYOLJXMZ-UHFFFAOYSA-N 0.000 description 1
229940117360 ethyl pyruvate Drugs 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
VMIWDXLESKKQTR-UHFFFAOYSA-N methyl 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline-7-carboxylate Chemical compound COC(=O)C1NCC2=CC3=C(C=C2C1)OCO3 VMIWDXLESKKQTR-UHFFFAOYSA-N 0.000 description 1
XAVYTZMVMTXAEC-UHFFFAOYSA-N methyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate Chemical compound COC1=C(OC)C=C2CNC(C(=O)OC)CC2=C1 XAVYTZMVMTXAEC-UHFFFAOYSA-N 0.000 description 1
ZIYVJULFKDQUMF-UHFFFAOYSA-N methyl 6-chloro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate Chemical compound COC(=O)C1NCC2=CC=C(C=C2C1)Cl ZIYVJULFKDQUMF-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
230000007935 neutral effect Effects 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
238000005121 nitriding Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical group C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- 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
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- 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
- 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)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Pyridine Compounds (AREA)

CH1691/82A 1981-03-19 1982-03-18 Peptidderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel. CH658455A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US24540781A	1981-03-19	1981-03-19

Publications (1)

Publication Number	Publication Date
CH658455A5 true CH658455A5 (de)	1986-11-14

Family

ID=22926526

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1691/82A CH658455A5 (de)	1981-03-19	1982-03-18	Peptidderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel.

Country Status (21)

Country	Link
JP (1)	JPS57165355A (el)
KR (1)	KR890001146B1 (el)
AU (1)	AU558451B2 (el)
BE (1)	BE892552A (el)
CH (1)	CH658455A5 (el)
DE (1)	DE3209708A1 (el)
DK (1)	DK120982A (el)
ES (3)	ES8307718A1 (el)
FI (1)	FI820974L (el)
FR (1)	FR2502149A1 (el)
GB (1)	GB2095252B (el)
IE (1)	IE53076B1 (el)
IL (1)	IL65247A (el)
IN (1)	IN156096B (el)
IT (1)	IT1150697B (el)
NL (1)	NL8201066A (el)
NO (1)	NO820903L (el)
NZ (1)	NZ200047A (el)
PH (1)	PH18657A (el)
SE (1)	SE8201654L (el)
ZA (1)	ZA821833B (el)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3242599A1 (de) *	1982-11-18	1984-05-24	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel
US4410520A (en) *	1981-11-09	1983-10-18	Ciba-Geigy Corporation	3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
US4555502A (en) *	1982-09-30	1985-11-26	Merck & Co., Inc.	Aminoacyl-containing dipeptide derivatives useful as antihypertensives
US4410807A (en) *	1982-03-26	1983-10-18	Kay Industries, Inc.	Regulating device for polyphase electrical circuits
US4473575A (en) *	1982-07-19	1984-09-25	Ciba-Geigy Corporation	3-Amino-(1)-benzazepin-2-one-1-alkanoic acids
US4520025A (en) *	1982-07-21	1985-05-28	William H. Rorer, Inc.	Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses
DE3302125A1 (de) *	1983-01-22	1984-07-26	Boehringer Ingelheim KG, 6507 Ingelheim	Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung
FI841052A (fi) *	1983-03-16	1984-09-17	Usv Pharma Corp	Foereningar foer behandling av blodtryckssjukdomar.
DE3333454A1 (de) *	1983-09-16	1985-04-11	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von n-alkylierten dipeptiden und deren estern
DE3622297A1 (de) *	1986-07-03	1988-01-07	Basf Ag	Disazothiophenfarbstoffe
US5246943A (en) *	1992-05-19	1993-09-21	Warner-Lambert Company	Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties
ES2122941B1 (es) *	1997-05-29	1999-07-01	Esteve Quimica Sa	Procedimiento para la obtencion de quinapril clorhidrato y solvatos utiles para el aislamiento y purificacion de quinapril clorhidrato.
ES2289060T3 (es)	2002-01-30	2008-02-01	Les Laboratoires Servier	Proceso para la preparacion de perindopril de alta pureza y de intermedios utiles en su sintesis.
ATE360616T1 (de)	2002-12-16	2007-05-15	Lupin Ltd	Kristalline form von quinapril hydrochlorid und verfahren zu dessen herstellung
US7521566B2 (en) *	2003-02-28	2009-04-21	Les Laboratoires Servier	Process for preparation of perindopril and salts thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2503155A2 (fr) *	1980-10-02	1982-10-08	Science Union & Cie	Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme
EP0046953B1 (de) *	1980-08-30	1989-12-06	Hoechst Aktiengesellschaft	Aminosäurederivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung
US4344949A (en) *	1980-10-03	1982-08-17	Warner-Lambert Company	Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids
GB2086390B (en) *	1980-11-03	1984-06-06	Ciba Geigy Ag	1-carboxy-azaalkanoylindoline-2-carboxylic acids process for their manufacture pharmaceutical preparations containing these compounds and their therapeutic application

1982
- 1982-03-08 IN IN265/CAL/82A patent/IN156096B/en unknown
- 1982-03-15 NL NL8201066A patent/NL8201066A/nl not_active Application Discontinuation
- 1982-03-15 PH PH26998A patent/PH18657A/en unknown
- 1982-03-15 IL IL65247A patent/IL65247A/xx unknown
- 1982-03-16 SE SE8201654A patent/SE8201654L/xx not_active Application Discontinuation
- 1982-03-16 AU AU81584/82A patent/AU558451B2/en not_active Ceased
- 1982-03-17 GB GB8207770A patent/GB2095252B/en not_active Expired
- 1982-03-17 DE DE19823209708 patent/DE3209708A1/de not_active Withdrawn
- 1982-03-17 ES ES510498A patent/ES8307718A1/es not_active Expired
- 1982-03-18 KR KR8201157A patent/KR890001146B1/ko active
- 1982-03-18 NO NO820903A patent/NO820903L/no unknown
- 1982-03-18 IT IT20259/82A patent/IT1150697B/it active
- 1982-03-18 DK DK120982A patent/DK120982A/da not_active Application Discontinuation
- 1982-03-18 BE BE0/207610A patent/BE892552A/fr not_active IP Right Cessation
- 1982-03-18 CH CH1691/82A patent/CH658455A5/de not_active IP Right Cessation
- 1982-03-18 ZA ZA821833A patent/ZA821833B/xx unknown
- 1982-03-18 NZ NZ200047A patent/NZ200047A/en unknown
- 1982-03-18 JP JP57041801A patent/JPS57165355A/ja active Pending
- 1982-03-19 FI FI820974A patent/FI820974L/fi not_active Application Discontinuation
- 1982-03-19 FR FR8204738A patent/FR2502149A1/fr active Granted
- 1982-03-19 IE IE635/82A patent/IE53076B1/en unknown
1983
- 1983-03-16 ES ES521030A patent/ES521030A0/es active Granted
- 1983-03-16 ES ES521031A patent/ES521031A0/es active Granted

Also Published As

Publication number	Publication date
IE53076B1 (en)	1988-06-08
AU558451B2 (en)	1987-01-29
KR830009065A (ko)	1983-12-17
IT1150697B (it)	1986-12-17
IE820635L (en)	1982-09-19
ES8501363A1 (es)	1984-12-01
ES8404317A1 (es)	1984-05-16
NZ200047A (en)	1985-07-12
IT8220259A0 (it)	1982-03-18
IL65247A0 (en)	1982-05-31
FR2502149A1 (fr)	1982-09-24
ES510498A0 (es)	1983-08-01
FR2502149B1 (el)	1985-01-18
DE3209708A1 (de)	1982-10-21
KR890001146B1 (ko)	1989-04-25
FI820974L (fi)	1982-09-20
NL8201066A (nl)	1982-10-18
BE892552A (fr)	1982-09-20
PH18657A (en)	1985-08-29
GB2095252B (en)	1985-04-17
GB2095252A (en)	1982-09-29
DK120982A (da)	1982-09-20
IL65247A (en)	1987-07-31
NO820903L (no)	1982-09-20
SE8201654L (sv)	1982-09-20
IN156096B (el)	1985-05-11
AU8158482A (en)	1982-09-23
ES521030A0 (es)	1984-05-16
ES8307718A1 (es)	1983-08-01
ES521031A0 (es)	1984-12-01
JPS57165355A (en)	1982-10-12
ZA821833B (en)	1983-01-26

Legal Events

Date	Code	Title	Description
1989-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0072352B1 (de)	1986-03-05	Benzazepin-2-one, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese Verbindungen enthalten, sowie die Verbindungen zur therapeutischen Verwendung
US4128653A (en)	1978-12-05	Reduction of blood pressure with carboxyalkylacyl-pipecolic acid derivatives
KR890000662B1 (ko)	1989-03-22	1-카복시 알카노일 인돌린-2-카복실산 유도체의 제조방법
EP0119954B1 (de)	1990-03-14	Gewisse 3-Amino-1-benzazepin-2-on-1-alkansäuren, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung
DE69310475T2 (de)	1997-09-04	Benzokondensierte Lactame
KR100504449B1 (ko)	2005-07-29	세포 유착 억제제
EP0236872B1 (de)	1992-11-25	Hydroxylaminderivate, deren Herstellung und Verwendung für Heilmittel
EP0100200B1 (en)	1987-05-06	2-substituted 4-amino-6,7-dimethoxyquinolines
US5576313A (en)	1996-11-19	Inhibitors of farnesyl-protein transferase
DE69416629T2 (de)	1999-07-22	2-Piperazinon-Verbindungen und deren Verwendung
EP0119161B1 (de)	1989-06-28	Gewisse Benzazocinon- und Benzazoninon-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung
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