CY1331A - Ergot peptide derivatives - Google Patents

Ergot peptide derivatives Download PDF

Info

Publication number: CY1331A
Authority: CY; Cyprus
Prior art keywords: compound; methyl; hydrogen; formula; ergot
Prior art date: 1979-06-12

Application number

CY1331A

Other languages

English (en)

Original Assignee

Sandoz Ltd

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.)

1979-06-12

Filing date

1980-06-09

Publication date

1986-06-27

1979-06-12 Priority claimed from CH547779A external-priority patent/CH643560A5/de

1979-06-12 Priority claimed from CH547679A external-priority patent/CH642082A5/de

1980-06-09 Application filed by Sandoz Ltd filed Critical Sandoz Ltd

1986-06-27 Publication of CY1331A publication Critical patent/CY1331A/en

Links

108090000765 processed proteins & peptides Proteins 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 100
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
229930015720 peptide alkaloid Natural products 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
150000003254 radicals Chemical class 0.000 claims description 14
229950001817 alpha-ergocryptine Drugs 0.000 claims description 13
229960004704 dihydroergotamine Drugs 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
ZCQPDHIMSLIIDW-MEBBXXQBSA-N (6ar,9r)-5,7-dimethyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=C(C)NC3=C1 ZCQPDHIMSLIIDW-MEBBXXQBSA-N 0.000 claims description 5
229960004943 ergotamine Drugs 0.000 claims description 5
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238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
229960003133 ergot alkaloid Drugs 0.000 description 1
239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000002513 implantation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001361 intraarterial administration Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
230000006651 lactation Effects 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000002746 orthostatic effect Effects 0.000 description 1
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
210000003523 substantia nigra Anatomy 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
ZVDMJHYRHCMIFM-MVCZASQCSA-N xi0xox1dt4 Chemical compound Cl.O=C1[C@H](CC(C)C)N2C(=O)[C@@](N)(C(C)C)O[C@@]2(O)[C@@H]2CCCN21 ZVDMJHYRHCMIFM-MVCZASQCSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Medicinal Preparation (AREA)
Steroid Compounds (AREA)

CY1331A 1979-06-12 1980-06-09 Ergot peptide derivatives CY1331A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH547779A CH643560A5 (en)	1979-06-12	1979-06-12	Ergopeptin derivatives, their preparation and use
CH547979		1979-06-12
CH547679A CH642082A5 (en)	1979-06-12	1979-06-12	Ergopeptin derivatives, their preparation and use
CH547879		1979-06-12

Publications (1)

Publication Number	Publication Date
CY1331A true CY1331A (en)	1986-06-27

Family

ID=27428898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY1331A CY1331A (en)	1979-06-12	1980-06-09	Ergot peptide derivatives

Country Status (24)

Country	Link
US (1)	US4547500A (fr)
AR (1)	AR231142A1 (fr)
AU (1)	AU545645B2 (fr)
CA (1)	CA1169856A (fr)
CY (1)	CY1331A (fr)
DE (1)	DE3020895A1 (fr)
DK (1)	DK250580A (fr)
ES (3)	ES492332A0 (fr)
FI (1)	FI70222C (fr)
FR (1)	FR2458552A1 (fr)
GB (2)	GB2053908B (fr)
HK (1)	HK40286A (fr)
HU (1)	HU184299B (fr)
IE (1)	IE49610B1 (fr)
IL (1)	IL60287A (fr)
IT (1)	IT1146938B (fr)
KE (1)	KE3622A (fr)
MA (1)	MA18872A1 (fr)
NL (1)	NL8003318A (fr)
NO (1)	NO154635C (fr)
NZ (1)	NZ193992A (fr)
PH (1)	PH19334A (fr)
PT (1)	PT71374B (fr)
SE (2)	SE445645B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU571927B2 (en) *	1979-06-12	1988-04-28	Sandoz Ltd.	A 2-methyl ergot peptide alkaloid
CH656533A5 (de) *	1982-12-10	1986-07-15	Sandoz Ag	Therapeutisches praeparat enthaltend hydrierte ergotalkaloide und niedermolekulares heparin.
GB8426922D0 (en) *	1984-10-24	1984-11-28	Sandoz Ltd	Galenic formulation
KR20140042868A (ko) *	2011-06-23	2014-04-07	맵 파마슈티컬스, 인코포레이티드	신규한 플루오로에르골린 유사체

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH507249A (de) *	1968-05-31	1971-05-15	Sandoz Ag	Verfahren zur Herstellung von 2-Brom-a-ergokryptin
CA990287A (en) *	1972-09-26	1976-06-01	Sandoz Patents Limited	13-bromo-lysergic acid compounds
CH588485A5 (en) *	1973-10-12	1977-06-15	Sandoz Ag	(17)-Ergolene derivs. prepn. - from lysergic acid (6)-(N)-oxide derivs.
CH587858A5 (fr) *	1973-11-28	1977-05-13	Sandoz Ag
CH610330A5 (en) *	1974-09-27	1979-04-12	Sandoz Ag	Process for the preparation of novel ergopeptins
CH601321A5 (fr) *	1975-01-06	1978-07-14	Sandoz Ag
AU526764B2 (en) *	1978-09-08	1983-01-27	Farmitalia Carlo Erba S.P.A.	Ergoline derivatives

1980
- 1980-06-02 DE DE19803020895 patent/DE3020895A1/de not_active Ceased
- 1980-06-05 FI FI801810A patent/FI70222C/fi not_active IP Right Cessation
- 1980-06-06 NL NL8003318A patent/NL8003318A/nl not_active Application Discontinuation
- 1980-06-09 CY CY1331A patent/CY1331A/en unknown
- 1980-06-09 MA MA19070A patent/MA18872A1/fr unknown
- 1980-06-09 GB GB8018827A patent/GB2053908B/en not_active Expired
- 1980-06-10 DK DK250580A patent/DK250580A/da not_active Application Discontinuation
- 1980-06-10 IT IT48924/80A patent/IT1146938B/it active
- 1980-06-10 NZ NZ193992A patent/NZ193992A/xx unknown
- 1980-06-10 CA CA000353712A patent/CA1169856A/fr not_active Expired
- 1980-06-10 IL IL60287A patent/IL60287A/xx unknown
- 1980-06-10 NO NO80801724A patent/NO154635C/no unknown
- 1980-06-10 SE SE8004306A patent/SE445645B/sv not_active IP Right Cessation
- 1980-06-11 AU AU59233/80A patent/AU545645B2/en not_active Ceased
- 1980-06-11 HU HU801473A patent/HU184299B/hu not_active IP Right Cessation
- 1980-06-11 FR FR8012931A patent/FR2458552A1/fr active Granted
- 1980-06-11 IE IE1206/80A patent/IE49610B1/en unknown
- 1980-06-11 ES ES492332A patent/ES492332A0/es active Granted
- 1980-06-11 PT PT71374A patent/PT71374B/pt unknown
- 1980-06-12 AR AR281379A patent/AR231142A1/es active
1981
- 1981-01-28 ES ES498871A patent/ES498871A0/es active Granted
- 1981-01-28 ES ES498872A patent/ES8205195A1/es not_active Expired
1982
- 1982-06-29 PH PH27511A patent/PH19334A/en unknown
- 1982-12-24 GB GB08236817A patent/GB2121030B/en not_active Expired
1983
- 1983-05-10 US US06/493,335 patent/US4547500A/en not_active Expired - Fee Related
1985
- 1985-02-04 SE SE8500490A patent/SE457260B/sv not_active IP Right Cessation
1986
- 1986-04-14 KE KE3622A patent/KE3622A/xx unknown
- 1986-05-29 HK HK402/86A patent/HK40286A/xx unknown

Also Published As

Publication number	Publication date
GB2053908A (en)	1981-02-11
PT71374B (en)	1981-06-25
KE3622A (en)	1986-05-16
DK250580A (da)	1980-12-13
AU5923380A (en)	1980-12-18
FR2458552B1 (fr)	1983-08-19
MA18872A1 (fr)	1980-12-31
IL60287A (en)	1986-03-31
HK40286A (en)	1986-06-06
US4547500A (en)	1985-10-15
ES498872A0 (es)	1982-06-01
HU184299B (en)	1984-07-30
ES8205195A1 (es)	1982-06-01
AR231142A1 (es)	1984-09-28
IT8048924A0 (it)	1980-06-10
AU545645B2 (en)	1985-07-25
ES8105331A1 (es)	1981-05-16
DE3020895A1 (de)	1980-12-18
FR2458552A1 (fr)	1981-01-02
SE445645B (sv)	1986-07-07
SE8004306L (sv)	1980-12-13
NZ193992A (en)	1982-12-21
IT1146938B (it)	1986-11-19
NL8003318A (nl)	1980-12-16
GB2053908B (en)	1983-11-30
IL60287A0 (en)	1980-09-16
ES492332A0 (es)	1981-05-16
SE457260B (sv)	1988-12-12
PT71374A (en)	1980-07-01
GB2121030A (en)	1983-12-14
FI70222C (fi)	1986-09-15
NO154635B (no)	1986-08-11
SE8500490L (sv)	1985-02-04
ES8205194A1 (es)	1982-06-01
IE49610B1 (en)	1985-10-30
PH19334A (en)	1986-03-21
FI70222B (fi)	1986-02-28
IE801206L (en)	1980-12-12
ES498871A0 (es)	1982-06-01
NO801724L (no)	1980-12-15
NO154635C (no)	1986-11-19
CA1169856A (fr)	1984-06-26
GB2121030B (en)	1984-05-23
FI801810A7 (fi)	1980-12-13
SE8500490D0 (sv)	1985-02-04

Publication	Publication Date	Title
IE53647B1 (en)	1989-01-04	Ergot peptide alkaloids their preparation and pharmaceutical compositions containing them
WO1992011262A1 (fr)	1992-07-09	Derives de 1-(4-acylaminophenyl)-7,8-methylenedioxy-5h-2,3-benzo-diazepine, leurs sels d'addition d'acides, compositions pharmaceutiques les contenant, et leur procede de preparation
US4950672A (en)	1990-08-21	2-substituted-8α-branched chain acylaminoergolines
GB2092144A (en)	1982-08-11	Novel indanyl derivaitves
GB1569251A (en)	1980-06-11	Pyridobenzodiazepines
US4547500A (en)	1985-10-15	Ergot peptide derivatives, their preparation and pharmaceutical compositions containing them
US4229451A (en)	1980-10-21	Ergopeptine derivatives
JPS5813542B2 (ja)	1983-03-14	シンキエルゴリンユウドウタイノセイホウ
US4299836A (en)	1981-11-10	Novel ergol-8-ene and ergolin compounds and process for preparing same
US3901891A (en)	1975-08-26	13-bromolysergic acid compounds
JPS5946235B2 (ja)	1984-11-10	シンキエルゴリンユウドウタイノセイホウ
CA1245641A (fr)	1988-11-29	Alcaloides de l'ergot de seigle
KR840000574B1 (ko)	1984-04-23	엘고트 펩타이드 유도체의 제조방법
US4004011A (en)	1977-01-18	3-Pyridylamine substituted ergolines
US4440772A (en)	1984-04-03	Acid addition salts of dextrorotatory ergot alkaloids, a process for the preparation thereof as well as their use as medicines
GB2125041A (en)	1984-02-29	Ergot alkaloids
IL34747A (en)	1973-07-30	Ergonorcornine,its 1-methyl derivative and their salts,their preparation and pharmaceutical compositions containing them
US4219556A (en)	1980-08-26	Substituted-8-phenylamino ergolines
WO2000008027A1 (fr)	2000-02-17	Antagonistes du recepteur opioide kappa (op2)
US4746666A (en)	1988-05-24	Ergoline compounds useful as antiparkinson agents
IL31437A (en)	1972-02-29	History of methylargolan and methylargoline, their preparation and pharmaceutical preparations containing them
IE49611B1 (en)	1985-10-30	A 2-methyl ergot peptide alkaloid
NO173542B (no)	1993-09-20	Analogifremgangsmaate ved fremstilling av terapeutisk aktive aminotetrahydronaftalenderivater
EP0411495A2 (fr)	1991-02-06	Dérivés de proline d'ergoline et composés apparentés à action dopaminergique
CA1192189A (fr)	1985-08-20	Derives e-homs-eburnanes et procede de preparation