DE2059923C3 - l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel - Google Patents
l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende ArzneimittelInfo
- Publication number
- DE2059923C3 DE2059923C3 DE19702059923 DE2059923A DE2059923C3 DE 2059923 C3 DE2059923 C3 DE 2059923C3 DE 19702059923 DE19702059923 DE 19702059923 DE 2059923 A DE2059923 A DE 2059923A DE 2059923 C3 DE2059923 C3 DE 2059923C3
- Authority
- DE
- Germany
- Prior art keywords
- isopropyl
- acid
- methyl
- aminopropyl
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 11
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 229960001722 verapamil Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- -1 acrylic ester Chemical class 0.000 description 4
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UKIFGNQFSBXGCF-UHFFFAOYSA-N 1-(3-chloropropoxy)-2-methoxybenzene Chemical compound COC1=CC=CC=C1OCCCCl UKIFGNQFSBXGCF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- ZJQKISPTWPQBSR-UHFFFAOYSA-N methanamine;toluene Chemical class NC.CC1=CC=CC=C1 ZJQKISPTWPQBSR-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702059923 DE2059923C3 (de) | 1970-12-05 | 1970-12-05 | l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
| GB5472171A GB1367677A (en) | 1970-12-05 | 1971-11-25 | Optically active basically substituted phenylacetonitriles |
| CH1728771A CH565748A5 (enExample) | 1970-12-05 | 1971-11-26 | |
| YU302371A YU35346B (en) | 1970-12-05 | 1971-12-01 | Process for obtaining laevogyric optically active, base-substituted phenylacetonitriles |
| AT1035371A AT305262B (de) | 1970-12-05 | 1971-12-01 | Verfahren zur Herstellung neuer, linksdrehender, basisch substituierter Phenylacetonitrile sowie deren Salze |
| NL7116577A NL172744C (nl) | 1970-12-05 | 1971-12-02 | Werkwijze voor het bereiden van basisch gesubstitueerde fenylacetonitrile-verbindingen en deze verbindingen bevattende geneesmiddelen met een de coronaire doorstroming bevorderende activiteit. |
| BE776218A BE776218A (fr) | 1970-12-05 | 1971-12-03 | Phenyl-acetonitriles a substitution basique, optiquement actifs |
| CA129,295A CA981693A (en) | 1970-12-05 | 1971-12-03 | Optically active, basically substituted phenylacetonitriles |
| FR7143744A FR2116564B1 (enExample) | 1970-12-05 | 1971-12-06 | |
| YU21879A YU35348B (en) | 1970-12-05 | 1979-02-01 | Tprocess for obtaining laevogyric optically active, base-substituted phenylacetonitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702059923 DE2059923C3 (de) | 1970-12-05 | 1970-12-05 | l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2059923A1 DE2059923A1 (de) | 1972-06-15 |
| DE2059923B2 DE2059923B2 (de) | 1978-05-18 |
| DE2059923C3 true DE2059923C3 (de) | 1979-01-25 |
Family
ID=5790091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702059923 Expired DE2059923C3 (de) | 1970-12-05 | 1970-12-05 | l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT305262B (enExample) |
| BE (1) | BE776218A (enExample) |
| CH (1) | CH565748A5 (enExample) |
| DE (1) | DE2059923C3 (enExample) |
| FR (1) | FR2116564B1 (enExample) |
| GB (1) | GB1367677A (enExample) |
| NL (1) | NL172744C (enExample) |
| YU (2) | YU35346B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4305887A (en) | 1979-11-11 | 1981-12-15 | Basf Aktiengesellschaft | Process for obtaining the enantiomeric forms of 4-cyano-1-[N-methyl-N-(2'-{3",4"-dimethoxyphenyl}-ethyl)-amino]-5-methyl-4-(3',4',5'-trimethoxyphenyl)-hexane and of salts thereof |
| US4350636A (en) | 1980-09-11 | 1982-09-21 | Basf Aktiengesellschaft | Preparation of phenylacetonitriles carrying basic substituents |
| DE3603660A1 (de) * | 1986-02-06 | 1987-09-03 | Basf Ag | Fluessigkeit zur peritonealdialyse |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3144150A1 (de) | 1981-04-10 | 1982-12-09 | Basf Ag, 6700 Ludwigshafen | (omega)-cyan-1,(omega)-diphenyl-azaalkan-derivate, ihre herstellung und diese enthaltende arzneimittel |
| DE3138488A1 (de) * | 1981-09-28 | 1983-04-14 | Knoll Ag, 6700 Ludwigshafen | Verwendung von basisch substituierten phenylacetonritrilen bei der vorbeugenden bekaempfung von krankheiten und mittel dafuer |
| DE3344755A1 (de) * | 1983-12-10 | 1985-06-20 | Basf Ag, 6700 Ludwigshafen | 1,7-diphenyl-3-methylaza-7-cyan-8-methyl-nonan zur verwendung bei der bekaempfung von krankheiten |
| DE3635930A1 (de) * | 1986-10-22 | 1988-04-28 | Basf Ag | Wirkstoffe zur anwendung bei der behandlung von tumoren |
| DE4203547A1 (de) * | 1992-02-07 | 1993-08-12 | Knoll Ag | Verfahren zur racemattrennung von verapamil |
| GB9319918D0 (en) * | 1993-09-27 | 1993-11-10 | Chiros Ltd | Chiral compounds and their preparation |
| US5910601A (en) * | 1994-09-26 | 1999-06-08 | Darwin Discovery Limited | Chiral nitriles, their preparation and their use for the manufacture of verapamil and analogues |
| US5892093A (en) * | 1996-02-08 | 1999-04-06 | Darwin Discovery Limited | Resolution |
| JP2000504683A (ja) * | 1996-02-08 | 2000-04-18 | ダーウィン・ディスカバリー・リミテッド | ４―シアノ―４―（３，４―ジメトキシフェニル）―５―メチルヘキサン酸の分割 |
| WO1997044025A1 (en) * | 1996-05-23 | 1997-11-27 | G.D. Searle & Co. | Pharmaceutical compositions containing non-racemic verapamil and process for optimizing the pharmaceutical activity of r- and s-verapamil |
| US5859279A (en) * | 1996-09-10 | 1999-01-12 | Darwin Discovery Limited | Compound and process |
| GB9618835D0 (en) * | 1996-09-10 | 1996-10-23 | Chiroscience Ltd | Process |
| EP1167348A4 (en) * | 1999-03-16 | 2002-11-13 | Eisai Co Ltd | nitrile |
| ES2250150T3 (es) | 1999-07-06 | 2006-04-16 | Methylgene, Inc. | Inhibidores de sulfonamidometilfosfonato de la beta-lactamasa. |
| US6884791B2 (en) | 1999-07-06 | 2005-04-26 | Methylgene, Inc. | Inhibitors of β-lactamase |
| WO2008156820A1 (en) | 2007-06-20 | 2008-12-24 | Milestone Pharmaceuticals Inc. | Short acting phenylalkylamine calcium channel blockers and uses thereof |
| EP3294703A4 (en) | 2015-05-12 | 2019-01-02 | Piramal Enterprises Limited | A process for the preparation of verapamil hydrochloride |
-
1970
- 1970-12-05 DE DE19702059923 patent/DE2059923C3/de not_active Expired
-
1971
- 1971-11-25 GB GB5472171A patent/GB1367677A/en not_active Expired
- 1971-11-26 CH CH1728771A patent/CH565748A5/xx not_active IP Right Cessation
- 1971-12-01 AT AT1035371A patent/AT305262B/de not_active IP Right Cessation
- 1971-12-01 YU YU302371A patent/YU35346B/xx unknown
- 1971-12-02 NL NL7116577A patent/NL172744C/xx not_active IP Right Cessation
- 1971-12-03 BE BE776218A patent/BE776218A/xx not_active IP Right Cessation
- 1971-12-06 FR FR7143744A patent/FR2116564B1/fr not_active Expired
-
1979
- 1979-02-01 YU YU21879A patent/YU35348B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4305887A (en) | 1979-11-11 | 1981-12-15 | Basf Aktiengesellschaft | Process for obtaining the enantiomeric forms of 4-cyano-1-[N-methyl-N-(2'-{3",4"-dimethoxyphenyl}-ethyl)-amino]-5-methyl-4-(3',4',5'-trimethoxyphenyl)-hexane and of salts thereof |
| US4350636A (en) | 1980-09-11 | 1982-09-21 | Basf Aktiengesellschaft | Preparation of phenylacetonitriles carrying basic substituents |
| DE3603660A1 (de) * | 1986-02-06 | 1987-09-03 | Basf Ag | Fluessigkeit zur peritonealdialyse |
Also Published As
| Publication number | Publication date |
|---|---|
| YU35346B (en) | 1980-12-31 |
| NL172744B (nl) | 1983-05-16 |
| YU21879A (en) | 1980-06-30 |
| CH565748A5 (enExample) | 1975-08-29 |
| NL172744C (nl) | 1983-10-17 |
| BE776218A (fr) | 1972-06-05 |
| AT305262B (de) | 1973-02-26 |
| FR2116564B1 (enExample) | 1975-03-14 |
| YU302371A (en) | 1980-06-30 |
| FR2116564A1 (enExample) | 1972-07-13 |
| YU35348B (en) | 1980-12-31 |
| DE2059923A1 (de) | 1972-06-15 |
| GB1367677A (en) | 1974-09-18 |
| NL7116577A (enExample) | 1972-06-07 |
| DE2059923B2 (de) | 1978-05-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2059923C3 (de) | l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel | |
| AT363096B (de) | Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen | |
| DE2059985C3 (de) | Rechtsdrehende, basisch substituierte Phenylacetonitrile, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1770408A1 (de) | Links-1-n-Butyl-2',6'-Pipecoloxylidid und Verfahren zu seiner Herstellung | |
| DE1001261C2 (de) | Verfahren zur Herstellung von basischen Estern endocyclisch substituierter Mandelsaeuren und ihren Salzen | |
| DD205682A5 (de) | Verfahren zur herstellung von (-)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3-diazacyclopent-2-en und seinen salzen | |
| DE2004301A1 (de) | Phenylserinderivate | |
| DE716579C (de) | Verfahren zur Herstellung von Esteramiden der Mandelsaeure | |
| AT217025B (de) | Verfahren zur Herstellung von neuen α-Aminoisobutyrophenonverbindungen und deren Säureadditionssalzen | |
| AT238181B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| AT318557B (de) | Verfahren zur Herstellung von neuen 2-exo-Aminobornanen und von deren Säureadditionssalzen | |
| AT203004B (de) | Verfahren zur Herstellung von neuen Estern des Piperidyl-(2)-phenylcarbinols und von deren Salzen | |
| DE750481C (de) | Verfahren zur Herstellung von in waessrigen Loesungen bestaendigen Abkoemmlingen des2-Methyl-4-amino-naphthols-(1) | |
| DE1695580C (de) | Quaternare Verbindungen des Benzil saure beta piperidino athylesters und ein Verfahren zu ihrer Herstellung | |
| DE2710807C2 (de) | Benzylamino-alkancarboxamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE3420387A1 (de) | 2-(4-biphenylyl)-4-hexenonsaeure und ihre derivate mit entzuendungshemmender wirksamkeit | |
| AT260911B (de) | Verfahren zur Herstellung der optisch aktiven Formen des α-Methyl-β-(3,4-dihydroxyphenyl)-alanins und deren N,O,O-Triacetylderivate | |
| DE2031360A1 (de) | Neue cyclische Verbindungen und Ver fahren zu ihrer Herstellung | |
| DE2264663C3 (de) | Ungesättigte Sulfoxyde und Verfahren zu ihrer Herstellung | |
| DE965405C (de) | Verfahren zur Herstellung von Arzneimitteln oxytocischer und sympatholytischer Wirkung durch Umsetzung des Diaethylamids der Diaethylamino-Essigsaeure mit physiologisch vertraeglichen Saeuren | |
| DE1236524C2 (de) | Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin | |
| AT265530B (de) | Verfahren zur Herstellung von neuen Isochinolinderivaten | |
| DE1593782C3 (de) | 1-Nitrilophenoxy- 2- hydroxy -3- tertbutylaminopropane, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate | |
| AT238180B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| DE1279685B (de) | Verfahren zur Herstellung von L-(-)-ª‡-Methyl-ª‰-(3, 4-dihydroxy-phenyl)-alanin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |