DE2528609C3 - Desoxyvincaminsäureamide, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und Arzneimittel - Google Patents
Desoxyvincaminsäureamide, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und ArzneimittelInfo
- Publication number
- DE2528609C3 DE2528609C3 DE2528609A DE2528609A DE2528609C3 DE 2528609 C3 DE2528609 C3 DE 2528609C3 DE 2528609 A DE2528609 A DE 2528609A DE 2528609 A DE2528609 A DE 2528609A DE 2528609 C3 DE2528609 C3 DE 2528609C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- halide
- salts
- general formula
- deoxyvincamic
- 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
- 239000002253 acid Substances 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 150000007513 acids Chemical class 0.000 title claims 3
- 150000003839 salts Chemical class 0.000 title claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 206010021143 Hypoxia Diseases 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 2
- 229910052500 inorganic mineral Chemical class 0.000 claims 2
- 239000011707 mineral Chemical class 0.000 claims 2
- 239000012454 non-polar solvent Substances 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000007530 organic bases Chemical group 0.000 claims 1
- -1 oxalyl halide Chemical class 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- WXQJMUQRXNZZFY-POAQFYNOSA-N deoxyvincaminamide Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@H](C(N)=O)N5C2=C1 WXQJMUQRXNZZFY-POAQFYNOSA-N 0.000 description 2
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 229960002726 vincamine Drugs 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000863486 Vinca minor Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- ZFCQLDAGNBFMJQ-QUCCMNQESA-N apovincaminic acid Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(O)=O)N5C2=C1 ZFCQLDAGNBFMJQ-QUCCMNQESA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- NFAZOGXQOWEWBM-UHFFFAOYSA-N cyclobutanamine;hydrochloride Chemical compound Cl.NC1CCC1 NFAZOGXQOWEWBM-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 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
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7432095A FR2285880A1 (fr) | 1974-09-24 | 1974-09-24 | Nouvel amide, ses sels, sa preparation et les medicaments qui en contiennent |
| FR7516290A FR2312245A1 (fr) | 1975-05-26 | 1975-05-26 | Nouveaux apovincamides, leurs sels, leur preparation et les medicaments qui en contiennent |
| FR7517670A FR2313056A1 (fr) | 1975-06-06 | 1975-06-06 | Nouvel amide, ses sels, sa preparation et les medicaments qui en contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2528609A1 DE2528609A1 (de) | 1976-04-01 |
| DE2528609B2 DE2528609B2 (de) | 1977-10-13 |
| DE2528609C3 true DE2528609C3 (de) | 1978-06-01 |
Family
ID=27250361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2528609A Expired DE2528609C3 (de) | 1974-09-24 | 1975-06-26 | Desoxyvincaminsäureamide, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und Arzneimittel |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4011330A (en:Method) |
| JP (1) | JPS5139699A (en:Method) |
| CA (1) | CA1031344A (en:Method) |
| CH (1) | CH603651A5 (en:Method) |
| DE (1) | DE2528609C3 (en:Method) |
| DK (1) | DK138427B (en:Method) |
| ES (1) | ES438799A1 (en:Method) |
| FI (1) | FI751840A7 (en:Method) |
| GB (1) | GB1460235A (en:Method) |
| IE (1) | IE41260B1 (en:Method) |
| IL (1) | IL47590A (en:Method) |
| LU (1) | LU72792A1 (en:Method) |
| NL (1) | NL7508740A (en:Method) |
| NO (1) | NO752192L (en:Method) |
| SE (1) | SE7507088L (en:Method) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU171663B (hu) * | 1975-09-01 | 1978-02-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh 14-skobka-zamehhennogo metil-skobka zakryta-vinkana |
| GB1550496A (en) * | 1976-12-31 | 1979-08-15 | Logeais Labor Jacques | 1,2,3,3a4,5-hexahydro-canthine derivatives a process for their preparation and their therapeutic applications |
| FR2407931A1 (fr) * | 1977-11-02 | 1979-06-01 | Synthelabo | Derives de l'eburnamenine et leur application en therapeutique |
| HU187733B (en) * | 1982-06-30 | 1986-02-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing apovincaminic acid derivatives |
| HU191938B (en) * | 1984-07-11 | 1987-04-28 | Andras Vedres | Process for production of new derivatives of 9 and 11 nitro-apovincamin acid |
| JPH0349630Y2 (en:Method) * | 1985-09-12 | 1991-10-23 | ||
| FR2869034B1 (fr) * | 2004-04-14 | 2008-04-04 | Biocortech Soc Par Actions Sim | Derive du 14,15-dihydro 20,21-dinoreburnamenin 14-ol et leur utilisation pour le traitement des depressions |
| US9907786B2 (en) | 2014-10-21 | 2018-03-06 | Ions Pharmaceutical S.À R.L. | Therapeutic compositions containing harmine and isovanillin components, and methods of use thereof |
| US10092550B2 (en) | 2014-10-21 | 2018-10-09 | Ions Pharmaceutical S.À R.L. | Therapeutic compositions containing curcumin, harmine, and isovanillin components, and methods of use thereof |
| US12129265B2 (en) | 2020-07-21 | 2024-10-29 | Ankh Life Sciences Limited | Therapeutic agents and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2176516B1 (en:Method) * | 1972-03-22 | 1975-03-14 | Synthelabo |
-
1975
- 1975-05-19 FI FI751840*A patent/FI751840A7/fi not_active Application Discontinuation
- 1975-06-19 SE SE7507088A patent/SE7507088L/xx unknown
- 1975-06-19 NO NO752192A patent/NO752192L/no unknown
- 1975-06-19 DK DK277975AA patent/DK138427B/da unknown
- 1975-06-23 ES ES75438799A patent/ES438799A1/es not_active Expired
- 1975-06-23 IE IE1391/75A patent/IE41260B1/xx unknown
- 1975-06-23 US US05/589,088 patent/US4011330A/en not_active Expired - Lifetime
- 1975-06-24 LU LU72792A patent/LU72792A1/xx unknown
- 1975-06-24 CH CH818075A patent/CH603651A5/xx not_active IP Right Cessation
- 1975-06-26 CA CA230,244A patent/CA1031344A/en not_active Expired
- 1975-06-26 DE DE2528609A patent/DE2528609C3/de not_active Expired
- 1975-06-27 GB GB2736975A patent/GB1460235A/en not_active Expired
- 1975-06-27 IL IL47590A patent/IL47590A/xx unknown
- 1975-06-27 JP JP50079923A patent/JPS5139699A/ja active Pending
- 1975-07-22 NL NL7508740A patent/NL7508740A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| LU72792A1 (en:Method) | 1976-04-13 |
| FI751840A7 (en:Method) | 1976-03-25 |
| SE7507088L (sv) | 1976-03-25 |
| DK138427C (en:Method) | 1979-02-12 |
| DK277975A (en:Method) | 1976-03-25 |
| DE2528609A1 (de) | 1976-04-01 |
| DE2528609B2 (de) | 1977-10-13 |
| JPS5139699A (en) | 1976-04-02 |
| CA1031344A (en) | 1978-05-16 |
| NO752192L (en:Method) | 1976-03-25 |
| IL47590A0 (en) | 1975-08-31 |
| US4011330A (en) | 1977-03-08 |
| AU8257175A (en) | 1977-01-06 |
| NL7508740A (nl) | 1976-03-26 |
| IL47590A (en) | 1978-10-31 |
| IE41260L (en) | 1976-03-24 |
| IE41260B1 (en) | 1979-11-21 |
| CH603651A5 (en:Method) | 1978-08-31 |
| ES438799A1 (es) | 1977-03-16 |
| GB1460235A (en) | 1976-12-31 |
| DK138427B (da) | 1978-09-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2527914C3 (de) | Vincaminderivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel | |
| DE2904445A1 (de) | Alkylendiaminderivate, ihre herstellung und pharmazeutische mittel | |
| DE2558501A1 (de) | Verfahren zur herstellung von alpha, alpha, alpha-trisubstituierten acetamiden, acetonitrilen und methanen und diese verbindungen enthaltende pharmazeutische zubereitungen | |
| DE2528609C3 (de) | Desoxyvincaminsäureamide, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2504045B2 (de) | 16,17 dihydro-apovincaminsaeure-2- hydroxypropylester, deren salze, verfahren zu ihrer herstellung und arzneimittel | |
| DE2747369A1 (de) | N-substituierte lactame, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE4131584A1 (de) | Imidazolylmethyl-pyridine, ihre herstellung und anwendung als pharmazeutika | |
| DE2716172C2 (de) | Bis(6-[(hexahydro-1H-azepin-1-yl)-methylenamino]-penicillanoyloxy)-methan, seine Herstellung und dieses enthaltendes Arzneimittel | |
| CH619952A5 (en:Method) | ||
| DE2336670A1 (de) | Aminoaether von o-thymotinsaeureestern | |
| DE2029510C3 (de) | Dibenzofuranderivate und deren pharmazeutisch verträgliche Säureadditionssalze sowie Verfahren zu deren Herstellung und Arzneimittel mit einem Gehalt dieser Verbindungen | |
| CH635342A5 (de) | Verfahren zur herstellung von neuen octahydro-indolo(2,3-a)-chinolizinen. | |
| EP0003286B1 (de) | Ergopeptidalkaloid-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2450161C3 (de) | N-ß-(3',4'-Dihydroxyphenäthyl)- glutamin und dessen Alkylester sowie deren pharmakologisch verträgliche Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE3120913C2 (en:Method) | ||
| DE2559558C3 (de) | Apovincaminsäureamide, deren Salze mit Säuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE69705238T2 (de) | Derivate der asiatica-saeure mit einem modifizierten a-ring | |
| DE1941933C3 (de) | Basisch substituierte 10,11- Dihydro-5,10-endoxa-SH-dibenzo- [a,d] -cycloheptene und deren pharmakologisch verträgliche Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DD141927A5 (de) | Verfahren zur herstellung von 1,1-disubstituierten octahydroindolo eckige klammer auf 2,3-a eckige klammer zu chinolizinen | |
| CH624397A5 (en:Method) | ||
| DE3110376A1 (de) | Benzylalkoholderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten | |
| AT351540B (de) | Verfahren zur herstellung von neuen tetrahydro- isochinolinderivaten und deren salzen | |
| DE69013101T2 (de) | 2-(N-acyl)amino-6,7-dimethoxytetraline, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen mit antihypertensiver Wirkung, die diese enthalten. | |
| DE2710807C2 (de) | Benzylamino-alkancarboxamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2531108A1 (de) | Vincaminderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |