CH652720A5 - Ergoline derivatives, their preparation and use - Google Patents

Ergoline derivatives, their preparation and use Download PDF

Info

Publication number: CH652720A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; acid addition; addition salts; compounds
Prior art date: 1983-02-16

Application number

CH86383A

Other languages

German (de)

English (en)

Inventor

Paul Dr Pfaeffli

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.)

1983-02-16

Filing date

1983-02-16

Publication date

1985-11-29

1983-02-16 Application filed by Sandoz Ag filed Critical Sandoz Ag

1983-02-16 Priority to CH86383A priority Critical patent/CH652720A5/de

1984-02-03 Priority to NL8400333A priority patent/NL8400333A/nl

1984-02-03 Priority to HU84463A priority patent/HU196399B/hu

1984-02-08 Priority to DE19843404400 priority patent/DE3404400A1/de

1984-02-09 Priority to FR8402128A priority patent/FR2540874B1/fr

1984-02-10 Priority to BE1/10956A priority patent/BE898873A/fr

1984-02-13 Priority to GB08403723A priority patent/GB2135307B/en

1984-02-13 Priority to PL24623084A priority patent/PL246230A1/xx

1984-02-14 Priority to DK67284A priority patent/DK67284A/da

1984-02-14 Priority to SE8400782A priority patent/SE459970B/sv

1984-02-14 Priority to CA000447409A priority patent/CA1208630A/fr

1984-02-14 Priority to GR73799A priority patent/GR81770B/el

1984-02-14 Priority to IL70954A priority patent/IL70954A/xx

1984-02-14 Priority to NZ207145A priority patent/NZ207145A/en

1984-02-14 Priority to PT78101A priority patent/PT78101B/pt

1984-02-14 Priority to PH30239A priority patent/PH24707A/en

1984-02-14 Priority to IT47681/84A priority patent/IT1199062B/it

1984-02-14 Priority to FI840587A priority patent/FI80034C/fi

1984-02-15 Priority to ES529759A priority patent/ES8505252A1/es

1984-02-15 Priority to AU24625/84A priority patent/AU572822B2/en

1984-02-15 Priority to LU85212A priority patent/LU85212A1/fr

1984-02-15 Priority to AT0047984A priority patent/AT386410B/de

1984-02-15 Priority to IE353/84A priority patent/IE56871B1/xx

1985-11-29 Publication of CH652720A5 publication Critical patent/CH652720A5/de

1986-12-01 Priority to US06/936,204 priority patent/US4791116A/en

1987-12-30 Priority to MY270/87A priority patent/MY8700270A/xx

Links

238000002360 preparation method Methods 0.000 title claims abstract description 4
AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 33
102000015554 Dopamine receptor Human genes 0.000 claims abstract description 3
108050004812 Dopamine receptor Proteins 0.000 claims abstract description 3
230000004936 stimulating effect Effects 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 8
241000700159 Rattus Species 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
230000028327 secretion Effects 0.000 claims description 6
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 6
230000003291 dopaminomimetic effect Effects 0.000 claims description 5
108010057464 Prolactin Proteins 0.000 claims description 4
102000003946 Prolactin Human genes 0.000 claims description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
229940097325 prolactin Drugs 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
238000007920 subcutaneous administration Methods 0.000 claims description 4
238000002513 implantation Methods 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 2
208000027089 Parkinsonian disease Diseases 0.000 claims description 2
206010034010 Parkinsonism Diseases 0.000 claims description 2
101000687509 Rattus norvegicus Prolactin Proteins 0.000 claims description 2
230000004913 activation Effects 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 claims description 2
239000002585 base Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
229960003638 dopamine Drugs 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
238000002474 experimental method Methods 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
208000031424 hyperprolactinemia Diseases 0.000 claims description 2
238000002347 injection Methods 0.000 claims description 2
239000007924 injection Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 claims description 2
230000000144 pharmacologic effect Effects 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
210000003523 substantia nigra Anatomy 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
ARTRTLXKTHJPRW-ILZDJORESA-N (6ar,9s,10ar)-9-(diethylsulfamoylamino)-4-ethyl-7-methyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(CC)CC)=C3C2=CN(CC)C3=C1 ARTRTLXKTHJPRW-ILZDJORESA-N 0.000 abstract 1
238000007126 N-alkylation reaction Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH86383A 1983-02-16 1983-02-16 Ergoline derivatives, their preparation and use CH652720A5 (en)

Priority Applications (25)

Application Number	Priority Date	Filing Date	Title
CH86383A CH652720A5 (en)	1983-02-16	1983-02-16	Ergoline derivatives, their preparation and use
NL8400333A NL8400333A (nl)	1983-02-16	1984-02-03	Moederkoornalkaloiden, hun bereiding en hun toepassing.
HU84463A HU196399B (en)	1983-02-16	1984-02-03	Process for producing ergoline derivatives and pharmaceutical compositions comprising such compounds
DE19843404400 DE3404400A1 (de)	1983-02-16	1984-02-08	Mutterkornalkoloide, ihre herstellung und verwendung
FR8402128A FR2540874B1 (fr)	1983-02-16	1984-02-09	Nouveaux derives de l'acide lysergique, leur preparation et leur utilisation comme medicaments
BE1/10956A BE898873A (fr)	1983-02-16	1984-02-10	Nouveaux derives de l'acide lysergique, leur preparation et leur utilisation comme medicaments
GB08403723A GB2135307B (en)	1983-02-16	1984-02-13	Ergot derivatives
PL24623084A PL246230A1 (en)	1983-02-16	1984-02-13	Process for preparing ergot alkaloids
GR73799A GR81770B (fr)	1983-02-16	1984-02-14
FI840587A FI80034C (fi)	1983-02-16	1984-02-14	Foerfarande foer framstaellning av terapeutiskt anvaendbara mjoeldrygaalkaloider.
CA000447409A CA1208630A (fr)	1983-02-16	1984-02-14	Derives d'ergot
DK67284A DK67284A (da)	1983-02-16	1984-02-14	Meldroejealkaloider
IL70954A IL70954A (en)	1983-02-16	1984-02-14	N,n-diethyl-n'-((8 alpha)-1-ethyl(or isopropyl)-6-methylergolin-8-yl)sulfamide,their production and pharmaceutical compositions containing them
NZ207145A NZ207145A (en)	1983-02-16	1984-02-14	Ergot derivatives and pharmaceutical compositions
PT78101A PT78101B (en)	1983-02-16	1984-02-14	Process for the preparation of ergot derivatives
PH30239A PH24707A (en)	1983-02-16	1984-02-14	Ergot derivatives
IT47681/84A IT1199062B (it)	1983-02-16	1984-02-14	Derivati della segale cornuta,loro preparazione e loro impiego come medicamenti
SE8400782A SE459970B (sv)	1983-02-16	1984-02-14	Ergolin-8-yl-sulfamid, saett att framstaella denna och en farmaceutisk komposition
ES529759A ES8505252A1 (es)	1983-02-16	1984-02-15	Procedimiento para preparar derivados del cornezuelo del centeno
AU24625/84A AU572822B2 (en)	1983-02-16	1984-02-15	N,n-diethyl-ergolin-8-yl-sulphamide
LU85212A LU85212A1 (fr)	1983-02-16	1984-02-15	Nouveaux derives de l'acide lysergique,leur preparation et leur utilisation comme medicaments
AT0047984A AT386410B (de)	1983-02-16	1984-02-15	Verfahren zur herstellung von neuen ergolinderivaten
IE353/84A IE56871B1 (en)	1983-02-16	1984-02-15	Ergot derivatives
US06/936,204 US4791116A (en)	1983-02-16	1986-12-01	N,N-diethyl-N'-[(8α)-1-ethyl-6-methyl-ergolin-8-yl]-sulfamide useful as prolactin secretion inhibitor, anti-parkinson agents and anti-depressant agents
MY270/87A MY8700270A (en)	1983-02-16	1987-12-30	Ergot derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH86383A CH652720A5 (en)	1983-02-16	1983-02-16	Ergoline derivatives, their preparation and use

Publications (1)

Publication Number	Publication Date
CH652720A5 true CH652720A5 (en)	1985-11-29

Family

ID=4196935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH86383A CH652720A5 (en)	1983-02-16	1983-02-16	Ergoline derivatives, their preparation and use

Country Status (3)

Country	Link
BE (1)	BE898873A (fr)
CH (1)	CH652720A5 (fr)
LU (1)	LU85212A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1617856A4 (fr) *	2003-04-11	2010-05-26	Ipsen Pharma	Analogues chimeres de la somatostatine-dopamine
US8952128B2 (en)	2012-11-01	2015-02-10	Ipsen Pharma S.A.S.	Somatostatin-dopamine chimeric analogs
US9777039B2 (en)	2012-11-01	2017-10-03	Ipsen Pharma S.A.S.	Somatostatin analogs and dimers thereof

1983
- 1983-02-16 CH CH86383A patent/CH652720A5/de not_active IP Right Cessation
1984
- 1984-02-10 BE BE1/10956A patent/BE898873A/fr unknown
- 1984-02-15 LU LU85212A patent/LU85212A1/fr unknown

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1617856A4 (fr) *	2003-04-11	2010-05-26	Ipsen Pharma	Analogues chimeres de la somatostatine-dopamine
US8952128B2 (en)	2012-11-01	2015-02-10	Ipsen Pharma S.A.S.	Somatostatin-dopamine chimeric analogs
US9603942B2 (en)	2012-11-01	2017-03-28	Ipsen Pharma S.A.S.	Somatostatin-dopamine chimeric analogs
US9731027B2 (en)	2012-11-01	2017-08-15	Ipsen Pharma S.A.S.	Somatostatin-dopamine chimeric analogs
US9777039B2 (en)	2012-11-01	2017-10-03	Ipsen Pharma S.A.S.	Somatostatin analogs and dimers thereof

Also Published As

Publication number	Publication date
BE898873A (fr)	1984-08-10
LU85212A1 (fr)	1984-11-08

Legal Events

Date	Code	Title	Description
1991-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2500110C2 (fr)	1987-06-11
DE2203373A1 (de)	1972-08-17	Neue Imidazolinderivate,Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Praeparate
DE2722162A1 (de)	1977-12-01	Verfahren zur herstellung von phosphonigen saeuren
DE1242596B (de)	1967-06-22	Verfahren zur Herstellung des 1-Isopropylamino-2-hydroxy-3-(o-allyloxy-phenoxy)-propans
DE2362754C2 (de)	1985-11-21	Cyclopropylalkylaminoreste enthaltende Oxazolinverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
CH652720A5 (en)	1985-11-29	Ergoline derivatives, their preparation and use
CH652719A5 (en)	1985-11-29	Ergoline derivatives, their preparation and use
DE1934392C3 (de)	1974-05-30	Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung
DD139842A5 (de)	1980-01-23	Verfahren zur herstellung quaternaerer ammoniumsalze von phenylpropylaminen und phenylbutylaminen
CH649998A5 (de)	1985-06-28	Ergolinderivate, ein verfahren zu ihrer herstellung und heilmittel, enthaltend diese ergolinderivate als wirkstoff.
DE2711149C3 (de)	1980-12-11	N-Substituierte[4-Chlor-6-(23-xylidino)-2· pyrimidinyl- thio] essigsäureamide sowie Verfahren zu deren Herstellung
DE3404400A1 (de)	1984-08-16	Mutterkornalkoloide, ihre herstellung und verwendung
DE2508251C2 (de)	1983-12-29	Derivate des Indols, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel
DE2035419A1 (de)	1971-01-28	Neue Arzneimittel mit antineoplasüscher Wirksamkeit
DE2610864A1 (de)	1976-09-30	Carbamate von 2-halogenergolinen und 2-halogenergolenen und verfahren zu ihrer herstellung
CH642082A5 (en)	1984-03-30	Ergopeptin derivatives, their preparation and use
DE3107599C2 (de)	1982-12-16	N-Cyan-N'-methyl-N"-{2-[(5-methylthio-imidazol-4-yl)-methylthio]-äthyl}-guanidin, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel
CH643560A5 (en)	1984-06-15	Ergopeptin derivatives, their preparation and use
DE1147946B (de)	1963-05-02	Verfahren zur Herstellung von Phenthiazinderivaten und ihren Saeureadditionssalzen
CH511841A (de)	1971-08-31	Verfahren zur Herstellung von neuen Indolderivaten
DE1445817C (de)	1973-05-24	Azepindenvate und Verfahren zu ihrer Herstellung
WO1982000463A1 (fr)	1982-02-18	Derives de l'ergoline, procede de leur preparation, compositions pharmaceutiques les contenant et leur application en therapie
DE2251154B2 (de)	1980-10-16	2-Aminoalkylthio-4-(p-thiophenyl)-3H-l,5-benzodiazepinderivate, solche enthaltende Arzneimittel und Desinfektionsmittel und Verfahren zu ihrer Herstellung
AT221495B (de)	1962-05-25	Verfahren zur Herstellung von neuen Dibenzocycloheptanderivaten und deren Salzen bzw. quaternären Ammoniumverbindungen
DE2200204A1 (de)	1972-07-27	Verfahren zur Herstellung neuer heterozyklischer Verbindungen