DE2245726B2 - -androstan-17 ß -yl)-acrylnitril-3",4"-carbonat, Verfahren zu seiner Herstellung und diese enthaltende Arzneimittel - Google Patents
-androstan-17 ß -yl)-acrylnitril-3",4"-carbonat, Verfahren zu seiner Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE2245726B2 DE2245726B2 DE2245726A DE2245726A DE2245726B2 DE 2245726 B2 DE2245726 B2 DE 2245726B2 DE 2245726 A DE2245726 A DE 2245726A DE 2245726 A DE2245726 A DE 2245726A DE 2245726 B2 DE2245726 B2 DE 2245726B2
- Authority
- DE
- Germany
- Prior art keywords
- androstan
- acrylonitril
- carbonat
- preparation
- medicaments containing
- 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.)
- Pending
Links
- 239000003814 drug Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000020094 liqueur Nutrition 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 229940075582 sorbic acid Drugs 0.000 description 2
- 235000010199 sorbic acid Nutrition 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 206010049993 Cardiac death Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010011906 Death Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2245726A DE2245726B2 (de) | 1972-09-18 | 1972-09-18 | -androstan-17 ß -yl)-acrylnitril-3",4"-carbonat, Verfahren zu seiner Herstellung und diese enthaltende Arzneimittel |
| ES418630A ES418630A1 (es) | 1972-09-18 | 1973-09-10 | Procedimiento para la preparacion de nuevos cardioglicosi- dos. |
| SU1962276A SU504494A3 (ru) | 1972-09-18 | 1973-09-14 | Способ получени сердечных гликозидов |
| DD173495A DD108081A5 (en, 2012) | 1972-09-18 | 1973-09-14 | |
| BG024549A BG21237A3 (bg) | 1972-09-18 | 1973-09-15 | Метод за получаване на нови сърдечни гликозиди |
| JP48104844A JPS4969652A (en, 2012) | 1972-09-18 | 1973-09-17 | |
| GB4359173A GB1438844A (en) | 1972-09-18 | 1973-09-17 | Steroid glycosides |
| ZA00737341A ZA737341B (en) | 1972-09-18 | 1973-09-17 | Improvements relating to cardiac glucosides |
| DK508073AA DK128776B (da) | 1972-09-18 | 1973-09-17 | Analogifremgangsmåde til fremstilling af 3-(3β-tridigitoxosyl-12β,14β-dihydroxy-5β-androstan-17β-yl)-acrylsyrederivater. |
| PL1973165268A PL84192B1 (en, 2012) | 1972-09-18 | 1973-09-17 | |
| CA181,161A CA1020540A (en) | 1972-09-18 | 1973-09-17 | Cardiac glucosides |
| AT799273A AT326280B (de) | 1972-09-18 | 1973-09-17 | Verfahren zur herstellung von neuen herzglykosiden |
| IL43244A IL43244A (en) | 1972-09-18 | 1973-09-17 | Digitoxosyl derivatives of 3beta,12beta,14beta-trihydroxyandrostanes,their preparation and pharmaceutical compositions containing them |
| IE1646/73A IE38249B1 (en) | 1972-09-18 | 1973-09-17 | Steroid glycosides |
| AU60364/73A AU476313B2 (en) | 1972-09-18 | 1973-09-17 | Steroid glycosides |
| PH15025A PH10559A (en) | 1972-09-18 | 1973-09-17 | Cardiac glycosides |
| BE135731A BE804949A (fr) | 1972-09-18 | 1973-09-17 | Nouveaux glycosides tonicardiaques |
| FI732881A FI52224C (fi) | 1972-09-18 | 1973-09-17 | Menetelmä 3-(-beta-tridigitoksosyyli-12beta-, 14beta-dihydroksi-5beta- androstan-17beta-yyli)-akryylinitriili-3''',4'''-karbonaatin valmistam iseksi, jolla on positiivinen inotrooppinen vaikutus sydämeen. |
| HUTO932A HU166033B (en, 2012) | 1972-09-18 | 1973-09-17 | |
| US397852A US3907776A (en) | 1972-09-18 | 1973-09-17 | Cardiac glycosides |
| CH1336473A CH581668A5 (en, 2012) | 1972-09-18 | 1973-09-18 | |
| FR7333415A FR2199987B1 (en, 2012) | 1972-09-18 | 1973-09-18 | |
| SE7312727A SE399897B (sv) | 1972-09-18 | 1973-09-18 | Forfarande for framstellning av nya hjertglykosider |
| CS7300006421A CS179429B2 (en) | 1972-09-18 | 1973-09-18 | Method for production of novel cardiac glycosides. |
| NL7312818A NL7312818A (en, 2012) | 1972-09-18 | 1973-09-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2245726A DE2245726B2 (de) | 1972-09-18 | 1972-09-18 | -androstan-17 ß -yl)-acrylnitril-3",4"-carbonat, Verfahren zu seiner Herstellung und diese enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2245726A1 DE2245726A1 (de) | 1974-04-04 |
| DE2245726B2 true DE2245726B2 (de) | 1979-01-18 |
Family
ID=5856646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2245726A Pending DE2245726B2 (de) | 1972-09-18 | 1972-09-18 | -androstan-17 ß -yl)-acrylnitril-3",4"-carbonat, Verfahren zu seiner Herstellung und diese enthaltende Arzneimittel |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3907776A (en, 2012) |
| JP (1) | JPS4969652A (en, 2012) |
| AT (1) | AT326280B (en, 2012) |
| AU (1) | AU476313B2 (en, 2012) |
| BE (1) | BE804949A (en, 2012) |
| BG (1) | BG21237A3 (en, 2012) |
| CA (1) | CA1020540A (en, 2012) |
| CH (1) | CH581668A5 (en, 2012) |
| CS (1) | CS179429B2 (en, 2012) |
| DD (1) | DD108081A5 (en, 2012) |
| DE (1) | DE2245726B2 (en, 2012) |
| DK (1) | DK128776B (en, 2012) |
| ES (1) | ES418630A1 (en, 2012) |
| FI (1) | FI52224C (en, 2012) |
| FR (1) | FR2199987B1 (en, 2012) |
| GB (1) | GB1438844A (en, 2012) |
| HU (1) | HU166033B (en, 2012) |
| IE (1) | IE38249B1 (en, 2012) |
| IL (1) | IL43244A (en, 2012) |
| NL (1) | NL7312818A (en, 2012) |
| PH (1) | PH10559A (en, 2012) |
| PL (1) | PL84192B1 (en, 2012) |
| SE (1) | SE399897B (en, 2012) |
| SU (1) | SU504494A3 (en, 2012) |
| ZA (1) | ZA737341B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5144017A (en) * | 1988-07-13 | 1992-09-01 | University Of Manitoba | Compounds that bind to digitalis receptor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3531462A (en) * | 1967-05-19 | 1970-09-29 | Shionogi Seiyaku Kk | Carbonates of cardenolide tridigitoxosides and ester derivatives thereof |
| DE2052634A1 (de) * | 1970-10-27 | 1972-05-04 | Dr Karl Thomae GmbH, 7950 Biberach | Neue durch einen Steroidrest substi tuierte Derivate der Acrylsäure und Ver fahren zu ihrer Herstellung |
| DE2122209A1 (de) * | 1971-05-05 | 1972-11-23 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue durch einen Steroidrest substituierte Derivate des Acrylnitrils und Verfahren zu ihrer Herstellung |
-
1972
- 1972-09-18 DE DE2245726A patent/DE2245726B2/de active Pending
-
1973
- 1973-09-10 ES ES418630A patent/ES418630A1/es not_active Expired
- 1973-09-14 DD DD173495A patent/DD108081A5/xx unknown
- 1973-09-14 SU SU1962276A patent/SU504494A3/ru active
- 1973-09-15 BG BG024549A patent/BG21237A3/bg unknown
- 1973-09-17 ZA ZA00737341A patent/ZA737341B/xx unknown
- 1973-09-17 US US397852A patent/US3907776A/en not_active Expired - Lifetime
- 1973-09-17 PH PH15025A patent/PH10559A/en unknown
- 1973-09-17 JP JP48104844A patent/JPS4969652A/ja active Pending
- 1973-09-17 GB GB4359173A patent/GB1438844A/en not_active Expired
- 1973-09-17 CA CA181,161A patent/CA1020540A/en not_active Expired
- 1973-09-17 HU HUTO932A patent/HU166033B/hu unknown
- 1973-09-17 FI FI732881A patent/FI52224C/fi active
- 1973-09-17 PL PL1973165268A patent/PL84192B1/pl unknown
- 1973-09-17 IL IL43244A patent/IL43244A/en unknown
- 1973-09-17 AU AU60364/73A patent/AU476313B2/en not_active Expired
- 1973-09-17 AT AT799273A patent/AT326280B/de not_active IP Right Cessation
- 1973-09-17 DK DK508073AA patent/DK128776B/da unknown
- 1973-09-17 BE BE135731A patent/BE804949A/xx unknown
- 1973-09-17 IE IE1646/73A patent/IE38249B1/xx unknown
- 1973-09-18 CH CH1336473A patent/CH581668A5/xx not_active IP Right Cessation
- 1973-09-18 SE SE7312727A patent/SE399897B/xx unknown
- 1973-09-18 NL NL7312818A patent/NL7312818A/xx not_active Application Discontinuation
- 1973-09-18 FR FR7333415A patent/FR2199987B1/fr not_active Expired
- 1973-09-18 CS CS7300006421A patent/CS179429B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK128776B (da) | 1974-07-01 |
| DE2245726A1 (de) | 1974-04-04 |
| CS179429B2 (en) | 1977-10-31 |
| CA1020540A (en) | 1977-11-08 |
| PH10559A (en) | 1977-06-08 |
| NL7312818A (en, 2012) | 1974-03-20 |
| SE399897B (sv) | 1978-03-06 |
| AT326280B (de) | 1975-12-10 |
| HU166033B (en, 2012) | 1974-12-28 |
| DD108081A5 (en, 2012) | 1974-09-05 |
| BG21237A3 (bg) | 1976-03-20 |
| IE38249L (en) | 1974-03-18 |
| FI52224C (fi) | 1977-07-11 |
| GB1438844A (en) | 1976-06-09 |
| BE804949A (fr) | 1974-03-18 |
| ZA737341B (en) | 1975-05-28 |
| FR2199987B1 (en, 2012) | 1977-01-28 |
| ES418630A1 (es) | 1976-02-16 |
| SU504494A3 (ru) | 1976-02-25 |
| FI52224B (en, 2012) | 1977-03-31 |
| FR2199987A1 (en, 2012) | 1974-04-19 |
| ATA799273A (de) | 1975-02-15 |
| IE38249B1 (en) | 1978-02-01 |
| PL84192B1 (en, 2012) | 1976-03-31 |
| US3907776A (en) | 1975-09-23 |
| IL43244A (en) | 1976-08-31 |
| CH581668A5 (en, 2012) | 1976-11-15 |
| AU476313B2 (en) | 1976-09-16 |
| JPS4969652A (en, 2012) | 1974-07-05 |
| AU6036473A (en) | 1975-03-20 |
| IL43244A0 (en) | 1973-11-28 |
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