CH623591A5 - Process for the preparation of ergopeptide alkaloid derivatives - Google Patents

Process for the preparation of ergopeptide alkaloid derivatives Download PDF

Info

Publication number: CH623591A5
Authority: CH; Switzerland
Prior art keywords: formula; compounds; methyl; butyl; isopropyl
Prior art date: 1976-09-06

Application number

CH1128676A

Other languages

German (de)

English (en)

Inventor

Peter Dr Stuetz

Paul Dr Stadler

Original Assignee

Sandoz Ag

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.)

1976-09-06

Filing date

1976-09-06

Publication date

1981-06-15

1976-09-06 Application filed by Sandoz Ag filed Critical Sandoz Ag

1976-09-06 Priority to CH1128676A priority Critical patent/CH623591A5/de

1977-06-02 Priority to ES462080A priority patent/ES462080A1/es

1977-08-27 Priority to DE19772738730 priority patent/DE2738730A1/de

1977-08-29 Priority to FI772557A priority patent/FI64942C/fi

1977-08-29 Priority to DK382777A priority patent/DK147390C/da

1977-08-29 Priority to SE7709645A priority patent/SE435839B/xx

1977-08-30 Priority to US05/829,206 priority patent/US4124712A/en

1977-08-31 Priority to GB9862/80A priority patent/GB1590150A/en

1977-08-31 Priority to GB36338/77A priority patent/GB1590149A/en

1977-09-02 Priority to CA286,056A priority patent/CA1105007A/fr

1977-09-02 Priority to NL7709683A priority patent/NL7709683A/xx

1977-09-05 Priority to BE180675A priority patent/BE858405A/fr

1977-09-05 Priority to PT67003A priority patent/PT67003B/pt

1977-09-05 Priority to IL52896A priority patent/IL52896A/xx

1977-09-05 Priority to NZ185098A priority patent/NZ185098A/xx

1977-09-05 Priority to PH20199A priority patent/PH12202A/en

1977-09-05 Priority to AT0635377A priority patent/AT367767B/de

1977-09-05 Priority to FR7726893A priority patent/FR2363571A1/fr

1977-09-05 Priority to JP10596277A priority patent/JPS5331698A/ja

1977-09-05 Priority to IE1838/77A priority patent/IE46152B1/en

1977-09-06 Priority to ZA00775366A priority patent/ZA775366B/xx

1977-09-06 Priority to SU772518255A priority patent/SU741793A3/ru

1977-09-06 Priority to AU28572/77A priority patent/AU512027B2/en

1981-06-15 Publication of CH623591A5 publication Critical patent/CH623591A5/de

Links

150000003797 alkaloid derivatives Chemical class 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 33
239000002253 acid Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
229910000085 borane Inorganic materials 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
230000003285 pharmacodynamic effect Effects 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
230000035484 reaction time Effects 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims description 2
229930013930 alkaloid Natural products 0.000 claims description 2
230000003276 anti-hypertensive effect Effects 0.000 claims description 2
230000037396 body weight Effects 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims description 2
229960003133 ergot alkaloid Drugs 0.000 claims description 2
238000002474 experimental method Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims 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 claims description 2
230000000694 effects Effects 0.000 abstract description 4
208000001953 Hypotension Diseases 0.000 abstract 1
208000021822 hypotensive Diseases 0.000 abstract 1
230000001077 hypotensive effect Effects 0.000 abstract 1
125000004043 oxo group Chemical group O=* 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229960004318 dihydroergocristine Drugs 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229950001817 alpha-ergocryptine Drugs 0.000 description 3
239000000243 solution Substances 0.000 description 3
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229960004704 dihydroergotamine Drugs 0.000 description 2
229960004943 ergotamine Drugs 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
206010047095 Vascular pain Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000013016 damping Methods 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
229960004290 dihydroergocornine Drugs 0.000 description 1
SEALOBQTUQIVGU-QNIJNHAOSA-N dihydroergocornine Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1 SEALOBQTUQIVGU-QNIJNHAOSA-N 0.000 description 1
DEQITUUQPICUMR-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 DEQITUUQPICUMR-HJPBWRTMSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
OWEUDBYTKOYTAD-MKTPKCENSA-N ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C3=CC=CC4=NC=C([C]34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 OWEUDBYTKOYTAD-MKTPKCENSA-N 0.000 description 1
HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 0.000 description 1
OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CH1128676A 1976-09-06 1976-09-06 Process for the preparation of ergopeptide alkaloid derivatives CH623591A5 (en)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
CH1128676A CH623591A5 (en)	1976-09-06	1976-09-06	Process for the preparation of ergopeptide alkaloid derivatives
ES462080A ES462080A1 (es)	1976-09-06	1977-06-02	Procedimiento para la obtencion de derivados de alcaloides peptidicos del cornezuelo de centeno.
DE19772738730 DE2738730A1 (de)	1976-09-06	1977-08-27	Ergopeptidalkaloidderivate, ihre verwendung und herstellung
FI772557A FI64942C (fi)	1976-09-06	1977-08-29	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbar 6'-desoxo-9,10-dihydro-beta-ergocryptin och salter daerav
DK382777A DK147390C (da)	1976-09-06	1977-08-29	Analogifremgangsmaade til fremstilling af ergopeptidalkaloidderivater
SE7709645A SE435839B (sv)	1976-09-06	1977-08-29	Analogiforfarande for framstellning av ergopeptidalkaloidderivat
US05/829,206 US4124712A (en)	1976-09-06	1977-08-30	Ergot peptide alkaloid derivatives
GB9862/80A GB1590150A (en)	1976-09-06	1977-08-31	Ergot peptide alkaloid derivative
GB36338/77A GB1590149A (en)	1976-09-06	1977-08-31	Ergot alkaloid peptide derivatives
CA286,056A CA1105007A (fr)	1976-09-06	1977-09-02	Traduction non-disponible
NL7709683A NL7709683A (nl)	1976-09-06	1977-09-02	Werkwijzen voor het bereiden en toepassen van alkaloiden.
BE180675A BE858405A (fr)	1976-09-06	1977-09-05	Nouveaux derives d'alcaloides peptidiques de l'ergot de seigle
PT67003A PT67003B (en)	1976-09-06	1977-09-05	Process for preparing a pharmaceutical composition containing new organic compounds
IL52896A IL52896A (en)	1976-09-06	1977-09-05	2',6-dialkyl-12'-hydroxyergotaman-3',18-dione derivatives,their production and pharmaceutical compositions containing them
NZ185098A NZ185098A (en)	1976-09-06	1977-09-05	6'-desoxoergopeptides
PH20199A PH12202A (en)	1976-09-06	1977-09-05	Ergot derivative
AT0635377A AT367767B (de)	1976-09-06	1977-09-05	Verfahren zur herstellung neuer ergopeptidalkaloidderivate
FR7726893A FR2363571A1 (fr)	1976-09-06	1977-09-05	Nouveaux derives d'alcaloides peptidiques de l'ergot de seigle
JP10596277A JPS5331698A (en)	1976-09-06	1977-09-05	Improvement concerning about organic compound
IE1838/77A IE46152B1 (en)	1976-09-06	1977-09-05	Ergot peptide aklaloid derivatives
ZA00775366A ZA775366B (en)	1976-09-06	1977-09-06	Improvements in or relating to organic compounds
SU772518255A SU741793A3 (ru)	1976-09-06	1977-09-06	Способ получени эргопептидалкалоидов или их солей
AU28572/77A AU512027B2 (en)	1976-09-06	1977-09-06	6' desoxo derivatives of ergot peptide alkaloid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1128676A CH623591A5 (en)	1976-09-06	1976-09-06	Process for the preparation of ergopeptide alkaloid derivatives

Publications (1)

Publication Number	Publication Date
CH623591A5 true CH623591A5 (en)	1981-06-15

Family

ID=4371966

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1128676A CH623591A5 (en)	1976-09-06	1976-09-06	Process for the preparation of ergopeptide alkaloid derivatives

Country Status (5)

Country	Link
AT (1)	AT367767B (fr)
BE (1)	BE858405A (fr)
CH (1)	CH623591A5 (fr)
SU (1)	SU741793A3 (fr)
ZA (1)	ZA775366B (fr)

1976
- 1976-09-06 CH CH1128676A patent/CH623591A5/de not_active IP Right Cessation
1977
- 1977-09-05 AT AT0635377A patent/AT367767B/de not_active IP Right Cessation
- 1977-09-05 BE BE180675A patent/BE858405A/fr not_active IP Right Cessation
- 1977-09-06 SU SU772518255A patent/SU741793A3/ru active
- 1977-09-06 ZA ZA00775366A patent/ZA775366B/xx unknown

Also Published As

Publication number	Publication date
ZA775366B (en)	1979-04-25
BE858405A (fr)	1978-03-06
AT367767B (de)	1982-07-26
SU741793A3 (ru)	1980-06-15
ATA635377A (de)	1981-12-15

Legal Events

Date	Code	Title	Description
1985-05-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0148440B1 (fr)	1988-10-05	1,3,4,5-Tétrahydrobenzo(c,d)indoles, procédé de préparation et utilisation
CH631696A5 (de)	1982-08-31	Verfahren zur herstellung von olefinischen derivaten von aminosaeuren.
DE2305092C2 (fr)	1987-10-01
DE2824905A1 (de)	1979-01-04	Neue 1, 2, 3, 4, 6, 7-hexahydro-11 balphah-benzo(a)chinolizin-derivate und verfahren zur herstellung derselben
DE1795022C3 (de)	1981-06-19	Lysergsäurederivate
DE2802023A1 (de)	1978-08-03	Neue ergotderivate, ihre herstellung und verwendung
EP0155903B1 (fr)	1989-08-23	Indolophénanthridines, leur préparation et leur utilisation
DE4131584A1 (de)	1993-03-25	Imidazolylmethyl-pyridine, ihre herstellung und anwendung als pharmazeutika
DE2632118A1 (de)	1977-01-20	Apovincaminolester und verfahren zu deren herstellung
DE1931081A1 (de)	1970-01-15	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
CH649999A5 (de)	1985-06-28	10-brom-e-homo-eburnane.
EP0003286B1 (fr)	1982-03-24	Dérivés d'alcaloides ergopeptidiques, procédé pour leur préparation et compositions pharmaceutiques les contenant
DE69131353T2 (de)	1999-10-14	Indolderivate
EP0180833B1 (fr)	1989-07-19	Dérivés de la 4-oxopyrido[2,3-d]pyrimidine, procédé pour leur préparation et médicaments les contenant
CH623591A5 (en)	1981-06-15	Process for the preparation of ergopeptide alkaloid derivatives
EP0026899A1 (fr)	1981-04-15	Alcaloides peptidiques d'ergot, procédé pour leur préparation, compositions pharmaceutiques les contenant et leur application dans les traitements thérapeutiques
DE2520131A1 (de)	1975-11-27	Stickstoffhaltige polycyclische verbindungen und verfahren zu deren herstellung
DE2835987A1 (de)	1979-03-01	3-amino-17a-aza-d-homo-5 alpha -androstanderivate und quaternaere salze davon sowie verfahren zu ihrer herstellung
DE2656678C2 (de)	1986-12-04	4-Amino-trans-decahydrochinolin-Derivate und Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DE2627190A1 (de)	1977-01-20	Neue fuenfring-verbindungen, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
CH615181A5 (en)	1980-01-15	Process for the preparation of novel ergolene derivatives
WO1983002775A1 (fr)	1983-08-18	Alcaloides d'ergot de seigle, leur procede de fabrication et preparations pharmaceutiques les contenant
DE3020895A1 (de)	1980-12-18	Ergopeptinderivate, verfahren zu deren herstellung sowie diese ergopeptinderivate enthaltende pharmazeutischen zusammensetzungen
DD246299A5 (de)	1987-06-03	Verfahren zur herstellung n-substituierter anziridin-2-carbonsaeurederivaten
CH658656A5 (de)	1986-11-28	Neue eburnamenin-14-carbonsaeure-derivate, verfahren zu ihrer herstellung und die neuen verbindungen enthaltende arzneimittelpraeparate.