DD231567A5 - Verfahren zur herstellung von gamma-butyrolacton-derivaten, die als myocard-schutz eine antiarrhythmische wirkung aufweisen - Google Patents
Verfahren zur herstellung von gamma-butyrolacton-derivaten, die als myocard-schutz eine antiarrhythmische wirkung aufweisen Download PDFInfo
- Publication number
- DD231567A5 DD231567A5 DD83270122A DD27012283A DD231567A5 DD 231567 A5 DD231567 A5 DD 231567A5 DD 83270122 A DD83270122 A DD 83270122A DD 27012283 A DD27012283 A DD 27012283A DD 231567 A5 DD231567 A5 DD 231567A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- preparation
- protection
- formula
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- -1 methyl-substituted piperidino group Chemical group 0.000 claims description 4
- 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 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 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 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 4
- 210000004165 myocardium Anatomy 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ARFMDOABESEOHU-DTORHVGOSA-N (2s,6r)-1-(2-chloroethyl)-2,6-dimethylpiperidine Chemical compound C[C@H]1CCC[C@@H](C)N1CCCl ARFMDOABESEOHU-DTORHVGOSA-N 0.000 description 1
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8218705A FR2535722B1 (fr) | 1982-11-08 | 1982-11-08 | Derives de la g-butyrolactone protecteurs du myocarde presentant une activite antiarythmique, procede pour leur preparation et medicaments en contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD231567A5 true DD231567A5 (de) | 1986-01-02 |
Family
ID=9278999
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83256412A DD220313A5 (de) | 1982-11-08 | 1983-11-07 | Verfahren zur herstellung von x-butyrolacton-derivaten |
| DD83270122A DD231567A5 (de) | 1982-11-08 | 1983-11-07 | Verfahren zur herstellung von gamma-butyrolacton-derivaten, die als myocard-schutz eine antiarrhythmische wirkung aufweisen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83256412A DD220313A5 (de) | 1982-11-08 | 1983-11-07 | Verfahren zur herstellung von x-butyrolacton-derivaten |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4542134A (el) |
| EP (1) | EP0113600B1 (el) |
| JP (1) | JPS59161379A (el) |
| KR (1) | KR900006723B1 (el) |
| AT (1) | ATE28644T1 (el) |
| AU (1) | AU560032B2 (el) |
| CA (1) | CA1224467A (el) |
| CS (1) | CS244680B2 (el) |
| DD (2) | DD220313A5 (el) |
| DE (1) | DE3372767D1 (el) |
| DK (1) | DK503683A (el) |
| ES (1) | ES527092A0 (el) |
| FI (1) | FI79538C (el) |
| FR (1) | FR2535722B1 (el) |
| GR (1) | GR78746B (el) |
| HU (1) | HU192825B (el) |
| IE (1) | IE56208B1 (el) |
| IL (1) | IL70062A (el) |
| MA (1) | MA19947A1 (el) |
| NO (1) | NO159853C (el) |
| NZ (1) | NZ206176A (el) |
| OA (1) | OA07581A (el) |
| PH (1) | PH19547A (el) |
| PL (2) | PL142949B1 (el) |
| PT (1) | PT77606B (el) |
| SG (1) | SG2389G (el) |
| SU (1) | SU1279529A3 (el) |
| YU (2) | YU220483A (el) |
| ZA (1) | ZA837935B (el) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714173A (en) * | 1971-07-06 | 1973-01-30 | Smith Kline French Lab | Pyridyl ketipate lactones and derivatives |
| FR2467200A1 (fr) * | 1979-10-11 | 1981-04-17 | Clin Midy | Derives du pyrrole actifs sur les troubles du rythme cardiovasculaire |
-
1982
- 1982-11-08 FR FR8218705A patent/FR2535722B1/fr not_active Expired
-
1983
- 1983-10-20 US US06/543,898 patent/US4542134A/en not_active Expired - Fee Related
- 1983-10-25 ZA ZA837935A patent/ZA837935B/xx unknown
- 1983-10-26 IL IL70062A patent/IL70062A/xx unknown
- 1983-10-27 AU AU20639/83A patent/AU560032B2/en not_active Ceased
- 1983-11-03 DK DK503683A patent/DK503683A/da not_active Application Discontinuation
- 1983-11-04 EP EP83402141A patent/EP0113600B1/fr not_active Expired
- 1983-11-04 AT AT83402141T patent/ATE28644T1/de not_active IP Right Cessation
- 1983-11-04 PT PT77606A patent/PT77606B/pt not_active IP Right Cessation
- 1983-11-04 IE IE2580/83A patent/IE56208B1/xx unknown
- 1983-11-04 GR GR72873A patent/GR78746B/el unknown
- 1983-11-04 DE DE8383402141T patent/DE3372767D1/de not_active Expired
- 1983-11-05 SU SU3661802A patent/SU1279529A3/ru active
- 1983-11-07 YU YU02204/83A patent/YU220483A/xx unknown
- 1983-11-07 CA CA000440588A patent/CA1224467A/en not_active Expired
- 1983-11-07 DD DD83256412A patent/DD220313A5/de not_active IP Right Cessation
- 1983-11-07 KR KR1019830005270A patent/KR900006723B1/ko active IP Right Grant
- 1983-11-07 FI FI834069A patent/FI79538C/fi not_active IP Right Cessation
- 1983-11-07 DD DD83270122A patent/DD231567A5/de not_active IP Right Cessation
- 1983-11-07 NO NO834053A patent/NO159853C/no unknown
- 1983-11-07 MA MA20167A patent/MA19947A1/fr unknown
- 1983-11-07 NZ NZ206176A patent/NZ206176A/en unknown
- 1983-11-08 HU HU833826A patent/HU192825B/hu not_active IP Right Cessation
- 1983-11-08 ES ES527092A patent/ES527092A0/es active Granted
- 1983-11-08 PL PL1983249775A patent/PL142949B1/pl unknown
- 1983-11-08 CS CS838219A patent/CS244680B2/cs unknown
- 1983-11-08 PH PH29801A patent/PH19547A/en unknown
- 1983-11-08 JP JP58209771A patent/JPS59161379A/ja active Pending
- 1983-11-08 OA OA58152A patent/OA07581A/xx unknown
- 1983-11-08 PL PL1983244461A patent/PL139945B1/pl unknown
-
1985
- 1985-09-12 YU YU01435/85A patent/YU143585A/xx unknown
-
1989
- 1989-01-11 SG SG23/89A patent/SG2389G/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |